A photosensitive resin composition containing a dispersion aid, a photosensitive resin film manufactured using the said composition, and a color filter.

Abstract

To provide a composition that combines superior pattern characteristics with high pigment dispersibility and dispersion stability, while providing high coloring power, contrast ratio, and residue characteristics.SOLUTION: A photosensitive resin composition comprises (A) a colorant, (B) a photopolymerizable compound, (C) a photopolymerization initiator, (D) a binder resin, and (E) a solvent, the colorant comprising a pigment, a dispersant, and a phthalocyanine-based dispersion aid represented by a specific formula.SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] A liquid crystal display device, which is one type of display device, has advantages such as being lightweight, thin, low-cost, low power consumption, and having excellent affinity with integrated circuits. Its scope of use has been expanded to notebook computers, monitors, and TVs.

[0003] Such a liquid crystal display device includes a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed, a liquid crystal layer, an active circuit portion composed of a thin film transistor and a storage capacitor layer, and an upper substrate on which an ITO pixel electrode is formed.

[0004] A color filter has a structure in which a black matrix layer formed in a pattern defined on a transparent substrate to block light at the boundary between pixels, and pixel portions in which a plurality of colors (usually the three primary colors of red (R), green (G), and blue (B)) are arranged in a defined order to form respective pixels are sequentially laminated.

[0005] One method for realizing a color filter, the pigment dispersion method, is a method in which a photopolymerizable composition containing a colorant is coated on a transparent substrate provided with a black matrix, the pattern to be formed is exposed, and then a non-exposed portion is removed with a solvent and thermally cured by repeating a series of processes to form a colored thin film.

[0006] The colored photosensitive resin composition used for manufacturing a color filter by the pigment dispersion method generally consists of an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives.

[0007] Pigment dispersion methods possessing the above characteristics are actively applied to the manufacture of LCDs for mobile phones, laptops, monitors, TVs, and other devices.

[0008] However, recently, even in photosensitive resin compositions for color filters using pigment dispersion methods, which have various advantages, there is a demand for not only excellent pattern characteristics but also further improved performance. In particular, there is an urgent need for high color reproducibility along with high brightness and high contrast ratio characteristics.

[0009] On the other hand, an image sensor refers to an image sensor component that generates images in mobile phone cameras and DSCs (Digital Still Cameras), and can be broadly classified into charge-coupled device (CCD) image sensors and complementary metal oxide semiconductor (CMOS) image sensors depending on their manufacturing process and application method.

[0010] In color image sensors used in solid-state image sensors or complementary metal oxide semiconductors, it is common practice to install color filters on the light-receiving element, each containing a filter segment for the additive mixing primary colors of red, green, and blue, to perform color separation.

[0011] Recently, the pattern size of color filters attached to such color image sensors is less than 2 μm, which is 1 / 100 to 1 / 200 times smaller than existing LCD color filter patterns. Therefore, increasing resolution and reducing residual image are important factors that affect the performance of the sensor.

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

[0013] One embodiment provides a photosensitive resin composition that has high dispersibility and dispersion stability, while also exhibiting excellent coloring power and contrast ratio when used in the realization of a color filter.

[0014] Another embodiment provides a photosensitive resin film manufactured using the above-described photosensitive resin composition.

[0015] Another embodiment provides a color filter including the above-mentioned photosensitive resin film. [Means for solving the problem]

[0016] One embodiment of the present invention provides a photosensitive resin composition 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 pigment, a dispersant, and a dispersion aid represented by the following chemical formula 1.

[0017] [ka]

[0018] In chemical formula 1, M is either Cu or Zn. R 11 ~R 14 , R 21 ~R 24 , and R 31 ~R 34is independently a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, R 41 ~R 44 is independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, R 41 ~R 44 at least one of which has a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms as a linking group and has an alkoxy group having 1 to 20 carbon atoms with an amino group as a substituent at the terminal or an aryloxy group having 6 to 20 carbon atoms with an amino group as a substituent at the terminal.

[0019] R 11 ~R 14 may all be hydrogen atoms or may all be halogen atoms.

[0020] R 21 ~R 24 one or two of which are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and the rest may all be hydrogen atoms.

[0021] R 31 ~R 34 may all be hydrogen atoms.

[0022] R 41 ~R 44 any one of which is represented by the following Chemical Formula L-1 or Chemical Formula L-2.

[0023]

Chemical Formula

[0024] In Chemical Formula L-1 or Chemical Formula L-2, L 1 and L 2Each of these is independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms. R 51 These are substituted or unsubstituted amino groups, n is an integer between 0 and 10.

[0025] R 51 It is represented by the following chemical formula N.

[0026] [ka]

[0027] In the chemical formula N, R 61 and R 62 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group, R 61 and R 62 These elements either exist independently or combine with each other to form a fused ring.

[0028] R 51 It can be represented by one of the following chemical formulas N-1 to N-6.

[0029] [ka]

[0030] [ka]

[0031] In chemical formula N-4 to chemical formula N-6, X 1 ~X 3 Each is independently either N or CH, R 71 ~R 77Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group. m is an integer between 0 and 4.

[0032] The dispersion aid represented by chemical formula 1 is represented by one of the following chemical formulas 1-1 to 1-13.

[0033] [ka]

[0034] [ka]

[0035] [ka]

[0036] [ka]

[0037] [ka]

[0038] The dispersion aid represented by chemical formula 1 may have a maximum absorption wavelength of 450 nm to 495 nm.

[0039] The dispersion aid represented by chemical formula 1 may be included in an amount of 0.01% to 1% by weight relative to the total amount of the photosensitive resin composition.

[0040] The weight ratio of the dispersion aid represented by chemical formula 1 to the pigment may be 1:20 to 1:70.

[0041] The pigments may include green pigments, yellow pigments, or combinations thereof.

[0042] The photosensitive resin composition may contain, based on the total amount of the photosensitive resin composition, (A) 15% to 50% by weight of a colorant, (B) 0.1% to 10% by weight of a photopolymerizable compound, (C) 0.1% to 5% by weight of a photopolymerization initiator, (D) 0.5% to 10% by weight of a binder resin, and the remainder of (E) a solvent.

[0043] Another embodiment provides a photosensitive resin film manufactured using a photosensitive resin composition.

[0044] The photosensitive resin film may be a negative photoresist.

[0045] Another embodiment provides a color filter including a photosensitive resin film.

[0046] Another embodiment provides a display device including a color filter.

[0047] Other specific aspects of the present invention are included in the detailed description below. [Effects of the Invention]

[0048] The photosensitive resin composition according to one embodiment possesses high dispersibility and dispersion stability, while also exhibiting excellent coloring power and contrast ratio when used in the realization of a color filter. Therefore, by using the photosensitive resin composition according to one embodiment, excellent color filters and display devices can be realized. [Modes for carrying out the invention]

[0049] 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 below.

[0050] 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 nitro group, a cyano group, an amino 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, a phosphoric acid or its salt, or a carbon This means that the substituent is a substituent of an alkyl group with 1 to 20 prime numbers, an alkenyl group with 2 to 20 carbon atoms, an alkynyl group with 2 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, a cycloalkenyl group with 3 to 20 carbon atoms, a cycloalkynyl group with 3 to 20 carbon atoms, a heterocycloalkyl group with 2 to 20 carbon atoms, a heterocycloalkenyl group with 2 to 20 carbon atoms, a heterocycloalkynyl group with 2 to 20 carbon atoms, or a combination thereof.

[0051] 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.

[0052] Unless otherwise specified herein, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible.

[0053] Unless otherwise defined herein, “combination” means mixing or copolymerization. “Copolymerization” means block copolymerization or random copolymerization, and “copolymer” means block copolymerization or random copolymerization.

[0054] Unless otherwise defined, if a chemical bond is not depicted in a chemical formula within this specification where one should be depicted, it means that a hydrogen atom is bonded to that position.

[0055] Unless otherwise defined herein, "*" means a portion linked to the same or different atoms or chemical formulas.

[0056] Unless otherwise defined herein, “particle size” may mean the diameter of a particle, which may be the Z-mean value of the particle diameter measured by dynamic light scattering.

[0057] (Photosensitive resin composition)

[0058] One embodiment provides a photosensitive resin composition 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 pigment, a dispersant, and a dispersion aid represented by the following chemical formula 1.

[0059] [ka]

[0060] In chemical formula 1, M is either Cu or Zn. R 11 ~R 14 , R 21 ~R 24 , and R 31 ~R 34 Each of these is independently a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. R 41 ~R 44 Each of these is independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, or a substituted or unsubstituted C6-C20 aryloxy group. R 41 ~R 44At least one of these is a C1-C20 alkoxy group having a substituted or unsubstituted C1-C20 oxyalkylene group as a linking group and an amino group as a substituent at its terminus, or a C6-C20 aryloxy group having an amino group as a substituent at its terminus.

[0061] (A) Coloring agent One embodiment of the photosensitive resin composition is a pigment-type photosensitive resin composition, and the colorant contains a pigment. In a color filter manufactured from a pigment-type photosensitive resin composition, there are limitations in brightness and contrast ratio due to the size of the pigment particles.

[0062] Furthermore, for applications in image sensors, resin compositions consisting of even smaller particles are required for the formation of fine patterns. To achieve this, it is necessary to develop compounds that promote pigment dispersion and suppress re-aggregation, as well as compositions using these compounds.

[0063] The dispersion aid represented by chemical formula 1 has a phthalocyanine core, but also has an amino group asymmetrically substituted with respect to the phthalocyanine core.

[0064] The phthalocyanine core interacts with the pigment, while the amino groups asymmetrically substituted on the phthalocyanine core interact with the dispersant or dispersion resin. Therefore, the dispersion aid represented by chemical formula 1 assists the dispersant in the photosensitive resin composition, enhancing the dispersibility and dispersion stability of the pigment.

[0065] Furthermore, the phthalocyanine-based nucleus exhibits blue coloration. Therefore, the dispersion aid represented by chemical formula 1 plays a role in enhancing the coloring power by assisting the colorant within the photosensitive resin composition.

[0066] Overall, the dispersion aid represented by chemical formula 1 is a dispersion aid that enhances the dispersibility and dispersion stability of pigments by assisting the dispersant, while also functioning to enhance the coloring power by assisting the colorant. Therefore, by using a photosensitive resin composition containing the dispersion aid represented by chemical formula 1 in color filters and display devices, further improved coloring power (color reproduction rate) and contrast ratio can be achieved.

[0067] For example, R 11 ~R 14 Each of these may independently be a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0068] For example, R 11 ~R 14 These atoms may all be hydrogen atoms, or they may all be halogen atoms. Here, the halogen atoms may also be chlorine atoms.

[0069] For example, R 21 ~R 24 Each of these may independently be a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0070] Specifically, R 21 ~R 24 All of them may be hydrogen atoms. Or, R 21 ~R 24 One of them may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and the rest may all be hydrogen atoms. For example, R 21 ~R 24 One or two of these may be branched C4 alkyl groups (tert-butyl groups), and the rest may all be hydrogen atoms.

[0071] R 21 ~R 24 Compared to the case where all are hydrogen atoms, R 21 ~R 24If one or two of these are branched C4 alkyl groups (tert-butyl groups), the solubility of the dispersion aid represented by chemical formula 1 in the solvent is improved.

[0072] R 21 ~R 24 The number of branched C4 alkyl groups (tert-butyl groups) among them may depend on the number of N-containing substituents (A) in the dispersion aid represented by chemical formula 1. If there is one N-containing substituent (A) in the dispersion aid represented by chemical formula 1, R 21 ~R 24 Among them, there may be just one branched C4 alkyl group (tert-butyl group). Also, if there are two substituents (A) containing N in the dispersion aid represented by chemical formula 1, R 21 ~R 24 There may also be two branched C4 alkyl groups (tert-butyl groups) among them. However, R 21 ~R 24 If there are three or more branched C4 alkyl groups (tert-butyl groups) in the compound, the chemical resistance of the dispersion aid represented by chemical formula 1 may actually decrease.

[0073] For example, R 31 ~R 34 Each of these may independently be a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0074] For example, R 31 ~R 34 These may all be hydrogen atoms.

[0075] For example, R 41 ~R 44 One of these is represented by either chemical formula L-1 or chemical formula L-2 below.

[0076] [ka]

[0077] In chemical formula L-1 or chemical formula L-2, L1 and L 2 Each of these is independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms. R 51 These are substituted or unsubstituted amino groups, n is an integer between 0 and 10.

[0078] The amino group asymmetrically substituted to the phthalocyanine core is R in the chemical formulas L-1 and L-2. 51 It is represented as follows. Furthermore, there is one or more amino groups asymmetrically substituted with the phthalocyanine core. This will be explained in detail below.

[0079] For example, R 51 It is represented by the following chemical formula N.

[0080] [ka]

[0081] In the chemical formula N, R 61 and R 62 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group, R 61 and R 62 These elements can exist independently or combine with each other to form a fused ring.

[0082] More specifically, R 51 It can be represented by one of the following chemical formulas N-1 to N-6, but is not necessarily limited to these.

[0083] [ka]

[0084] [ka]

[0085] In chemical formula N-4 to chemical formula N-6, X 1 ~X 3 Each is independently either N or CH, R 71 ~R 77 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group. m is an integer between 0 and 4.

[0086] The dispersion aid represented by chemical formula 1 has an amino group as a substituent in the above structure and is further linked to the phthalocyanine core by a linking group containing an "ester group and an oxyalkylene group" or an "ether group and an oxyalkylene group" (see structures of chemical formulas L-1 and L-2). Therefore, it has excellent dispersibility and dispersion stability, and can improve its coloring power and contrast ratio.

[0087] For example, a dispersion aid represented by chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-13, but is not necessarily limited to these.

[0088] [ka]

[0089] [ka]

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] As described above, the dispersion aid represented by chemical formula 1 has a phthalocyanine-based core that exhibits blue color, and therefore can further improve the coloring power and contrast ratio of the photosensitive resin composition.

[0094] Specifically, the dispersion aid represented by chemical formula 1 has a maximum absorption wavelength (λ max ) may be 450nm to 495nm.

[0095] The dispersion aid represented by chemical formula 1 may be included in the photosensitive resin composition in an amount of 0.01% to 1% by weight, specifically 0.05% to 0.5% by weight, for example, 0.1% to 0.3% by weight, relative to the total amount of the photosensitive resin composition.

[0096] Furthermore, the weight ratio of the dispersion aid and pigment represented by chemical formula 1 may be 1:10 to 1:70, more specifically 1:20 to 1:70, more specifically 1:20 to 1:60, or for example, 1:20 to 1:50.

[0097] By adopting the above ranges, it is possible to improve the dispersibility and dispersion stability of the photosensitive resin composition according to one embodiment, while also improving the coloring power and contrast ratio.

[0098] The coloring agent may contain pigments, and examples of pigments that can be used include green pigments, blue pigments, red pigments, purple pigments, yellow pigments, and black pigments.

[0099] Red pigments can be used within the Color Index, including 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. These can be used individually or in combination of two or more, but are not necessarily limited to these.

[0100] Purple pigments can include 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, and can be used individually or in mixtures of two or more, but are not necessarily limited to these.

[0101] Green pigments can be used within the Color Index, such as CI Green Pigment 7, CI Green Pigment 36, CI Green Pigment 58, and CI Green Pigment 59. These can be used individually or in combination of two or more, but are not necessarily limited to these.

[0102] Blue pigments can be 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 within the Color Index. These can be used alone or in mixtures of two or more, but are not necessarily limited to these.

[0103] Yellow pigments can include 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.

[0104] Black pigments can include aniline black, perylene black, titanium black, and carbon black within the Color Index, and these can be used individually or in mixtures of two or more, but are not necessarily limited to these.

[0105] Pigments can be used individually or in mixtures of two or more. For example, green pigments, yellow pigments, or mixtures thereof can be used as pigments.

[0106] The dispersant promotes the uniform dispersion of the pigment in the dispersion liquid, and nonionic, anionic, or cationic dispersants can be used. Specifically, polyalkylene glycol or its esters, polyoxyalkylene, 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.

[0107] The pigment may be included in the photosensitive resin composition for color filters in the form of a dispersion. Such a pigment dispersion may further contain a dispersion solvent, a dispersion resin, and the like, in addition to the pigment, dispersant, and dispersion aid. The solid pigment portion, excluding the solvent, may be included 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.

[0108] As the 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 is preferred.

[0109] As the dispersion resin, an acrylic resin containing carboxyl groups can be used, which not only improves the stability of the pigment dispersion but also improves the patternability of the pixels.

[0110] The colorant may contain a pigment and a dye, in which case the resin composition of one embodiment is a hybrid composition. The dye is not particularly limited, but may include metal complex dyes.

[0111] As metal complex dyes, compounds having maximum absorbance in the wavelength range of 200 nm to 650 nm can be used. Any metal complex dye of any color that is soluble in organic solvents can be used, as long as it has absorbance within the above range to match the color coordinates of the dye combination.

[0112] Specifically, as metal complex dyes, 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 can be used.

[0113] Metal complex dyes that can be used include 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.

[0114] 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.

[0115] Examples of 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 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, and other CI acid greens. CI Direct Dyes, such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, CI Basic Dyes, such as CI Basic Green 1, CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 4 A complex of the above-mentioned metal ion can be used with at least one selected from the group consisting of CI mordant dyes such as 1, 43, 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.

[0116] The dye containing the metal complex 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 dye containing the metal complex 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.

[0117] 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.

[0118] Having the specific range described above, it can be usefully used in color filters for LCDs, LEDs, and other devices to achieve high brightness and high contrast ratios in the desired color coordinates.

[0119] The dye containing the metal complex may be included in the photosensitive resin composition in an amount of 0.01% to 1% by weight, for example, 0.01% to 0.5% by weight, relative to the total amount. When the dye containing the metal complex is used within the above range, high brightness and contrast ratio can be achieved at the desired color coordinates.

[0120] When mixing dyes and pigments, they can be used in a weight ratio of 0.1:99.9 to 99.9:0.1, specifically 1:9 to 9:1. Mixing within this weight ratio range allows for appropriate control of chemical resistance and maximum absorption wavelength, resulting in high brightness and contrast ratios at the desired color coordinates.

[0121] The coloring agent may be included in an amount of 15% to 50% by weight, specifically 20% to 45% by weight, for example 30% to 40% 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 50% by weight, specifically 6% to 40% by weight, for example 7% to 30% by weight, based on the solid content, relative to the total amount of the photosensitive resin composition. When the coloring agent is included within the above ranges, the coloring effect and developability are excellent.

[0122] (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.

[0123] Because the photopolymerizable compound has an ethylenically unsaturated double bond, sufficient polymerization can be brought about by exposure during the pattern formation process, thereby forming a pattern with excellent heat resistance, light resistance, and chemical resistance.

[0124] 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.

[0125] Examples of commercially available photopolymerizable compounds include the following: Examples of monofunctional esters of (meth)acrylic acid include Arronix® M-101, M-111, and M-114 from Toagosei Chemical Industry Co., Ltd., KAYARAD® TC-110S and TC-120S from Nippon Kayaku Co., Ltd., and V-158 and V-2311 from Osaka Organic Chemical Industry Co., Ltd. Examples of difunctional esters of (meth)acrylic acid include Arronix® M-210, M-240, and M-6200 from Toagosei Chemical Industry Co., Ltd., KAYARAD® HDDA, HX-220, and R-604 from Nippon Kayaku Co., Ltd., and V-260, V-312, and V-335 HP from Osaka Organic Chemical Industry Co., Ltd. Examples of trifunctional esters of (meth)acrylic acid include Aronix® M-309, M-400, M-405, M-450, M-710, M-8030, and M-8060 from Toagosei Chemical Industry Co., Ltd., KAYARAD® TMPTA, DPCA-20, -30, -60, and -120 from Nippon Kayaku Co., Ltd., and V-295, -300, -360, -GPT, -3PA, and -400 from Osaka Organic Chemical Industry Co., Ltd. These products can be used individually or in combination of two or more.

[0126] Photopolymerizable compounds can also be treated with acid anhydrides before use to impart better developability.

[0127] 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 7% by weight, relative to the total amount of the photosensitive resin composition. When the photopolymerizable compound is included within the above range, a photosensitive resin composition can be obtained in which curing occurs sufficiently during exposure in the pattern formation process, is highly reliable, and has excellent developability in alkaline developers.

[0128] (C) Photopolymerization initiator The photopolymerization initiator is an initiator commonly used in photosensitive resin compositions, and for example, acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds, triazine compounds, oxime compounds, or combinations thereof can be used.

[0129] 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.

[0130] 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.

[0131] Examples of thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and 2-chlorothioxanthone.

[0132] Examples of benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

[0133] 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.

[0134] 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 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)-octane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-one oxime-O-acetate, and 1-(4-phenylsulfanylphenyl)-butan-1-one oxime-O-acetate.

[0135] 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.

[0136] 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.

[0137] Examples of photosensitizers include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, and dipentaerythritol tetrakis-3-mercaptopropionate.

[0138] 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 when exposed during the pattern formation process, and as a result, the photosensitive resin film can have excellent reliability, excellent heat resistance, light resistance, and chemical resistance of the pattern, excellent resolution and adhesion, and a reduction in transmittance due to unreacted initiator can be prevented.

[0139] (D) Binder resin The binder resin may include acrylic resins.

[0140] 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.

[0141] 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.

[0142] The first ethylenically unsaturated monomer may be present 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.

[0143] 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.

[0144] 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.

[0145] The binder resin may further contain epoxy-based binder resin.

[0146] The heat resistance of the binder resin can be improved by further including an epoxy-based binder resin. Examples of epoxy-based binder resins include, but are not limited to, phenol novolac epoxy resins, tetramethyl biphenyl epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, alicyclic epoxy resins, or combinations thereof.

[0147] Furthermore, the binder resin containing the epoxy-based binder resin ensures the dispersion stability of colorants such as pigments, as described later, while simultaneously promoting the formation of pixels with the desired resolution during the development process.

[0148] 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.

[0149] 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.

[0150] 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 binder resin in solid form may be about 0.1% to 30% by weight, for example, 20% to 30% by weight, relative to the total amount of the binder resin solution dissolved in the solvent.

[0151] Furthermore, the binder resin may be included in an amount of 0.1% to 20% by weight, specifically 0.5% to 15% by weight, for example, 1% to 10% by weight, relative to the total amount of the photosensitive resin composition. When the binder resin is included within the above range, excellent developability, good crosslinking properties, and excellent surface smoothness can be obtained during the manufacture of the color filter.

[0152] (E) Solvent The solvent can be a substance that is compatible with but does not react with colorants, binder resins, photopolymerizable compounds, and photopolymerization initiators.

[0153] 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-methyl-2-pentanone, and methyl-n-propyl ketone. Ketones such as methyl-n-butyl ketone, methyl-n-amyl ketone, 2-heptanone, saturated aliphatic monocarboxylate alkyl esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, lactic acid esters such as methyl lactate, ethyl lactate, alkyl oxyacetates such as methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, alkyl alkoxyacetates such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-hydroxypropionate, 3- 3-hydroxypropionate alkyl esters such as ethyl oxypropionate, 3-methoxypropionate methyl, 3-methoxypropionate ethyl, 3-ethoxypropionate ethyl, 3-ethoxypropionate methyl and other 3-alkoxypropionate alkyl esters, 2-hydroxypropionate methyl, 2-oxypropionate ethyl, 2-oxypropionate propyl and other 2-hydroxypropionate alkyl esters, 2-methoxypropionate methyl, 2-methoxypropionate ethyl, 2-ethoxypropionate ethyl,Alkyl 2-alkoxypropionates such as methyl 2-ethoxypropionate, 2-oxy-2-methylpropionates such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate, alkyl monooxymonocarboxylates of alkyl 2-alkoxy-2-methylpropionates such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate, esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyethyl acetate, and methyl 2-hydroxy-3-methylbutanoate, Examples include ketonic acid esters such as ethyl pyruvate, as well as 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.

[0154] Of these, considering compatibility and reactivity, propylene glycol monomethyl ether acetate (PGMEA), n-butyl acetate (n-BA), ethylene glycol dimethyl ether, or a combination thereof can be used as solvents.

[0155] The solvent may be included in the remainder of 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, the photosensitive resin composition can produce a coating film with excellent coatability and flatness.

[0156] (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.

[0157] The additives can be easily adjusted according to the desired physical properties.

[0158] The coupling agent may be a silane-based coupling agent. Examples of silane-based coupling agents include trimethoxysilylbenzoic acid, γ-methacrylateoxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatetopropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, and β-epoxycyclohexylethyltrimethoxysilane, which can be used individually or in combination of two or more.

[0159] Specifically, the silane coupling agent can be used in an amount of 0.01 to 1 part by weight per 100 parts by weight of the photosensitive resin composition.

[0160] Furthermore, the photosensitive resin composition for color filters may further contain a surfactant, such as a fluorinated surfactant, as needed.

[0161] Examples of fluorinated surfactants include, but are not limited to, DIC's F-482, F-484, and F-478.

[0162] The surfactant is preferably present in an amount of 0.01% to 5% by weight, and more preferably in an amount of 0.01% to 2% by weight, relative to the total amount of the photosensitive resin composition. Deviating from this range is undesirable because it can lead to problems such as the formation of foreign matter after development.

[0163] 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.

[0164] (Photosensitive resin film, color filter, and display device) According to another embodiment, a photosensitive resin film is provided that is manufactured using the photosensitive resin composition according to one embodiment.

[0165] The photosensitive resin film of one embodiment can be broadly classified into positive photoresist compositions and negative photoresist compositions.

[0166] The photosensitive resin film in one embodiment may be a negative photoresist. This has the advantage of not causing discoloration due to the photoresist and having relatively higher light sensitivity than a positive photoresist.

[0167] In yet another embodiment, a color filter manufactured using the above-described photosensitive resin composition is provided.

[0168] A method for manufacturing a color filter according to one embodiment is as follows.

[0169] 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.

[0170] 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 light irradiation process can also be carried out using a photomask. 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 unexposed areas of the photosensitive resin composition layer are 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, by curing the image pattern obtained by development in the above process by heating again or by chemical beam irradiation, crack resistance, solvent resistance, etc., can be improved.

[0171] In yet another embodiment, an electronic device including the color filter described above is provided.

[0172] The electronic device may be a display device such as a liquid crystal display device or a CMOS image sensor. [Examples]

[0173] 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.

[0174] (Example of combination) Synthesis Example 1: Compound represented by chemical formula 1-1 (1) Production of intermediate 1-1-1

[0175] [ka]

[0176] Methyl salicylate (10 g), 3,4,5,6-tetrachlorophthalonitrile (17.5 g), K2CO3 (10.9 g), and N,N-dimethylformamide (DMF) (100 mL) were placed in a 250 mL flask and stirred while heating to 70°C. After the reaction was complete, the mixture was extracted with ethyl acetate (EA). After extraction, the organic layer was concentrated, and the residue was purified by column chromatography. After purification, the residue was vacuum-dried to obtain intermediate 1-1-1.

[0177] (2) Production of intermediate 1-1-2

[0178] [ka]

[0179] In a 100 mL flask, intermediate 1-1-1 (4 g), phthalonitrile (1.34 g), 4-tert-butylphthalonitrile (1.93 g), 1,8-diazabicyclo[5.4.0]-7-undecene (3.19 g), and 1-pentanol (20 g) were placed and heated to 90°C. After dissolving the solid components, zinc acetate (1.93 g) was added and the mixture was stirred while heating to 140°C. After the reaction was complete, methanol was added to form a precipitate. The resulting solid was filtered and then vacuum-dried. The dried solid was purified by column chromatography. After purification, the obtained solid was dissolved in methylene chloride (MC), and then methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain intermediate 1-1-2.

[0180] (3) Preparation of the compound represented by chemical formula 1-1 Intermediate 1-1-2 (1.0 g), 2-[2-(dimethylamino)ethoxy]ethanol (0.30 g), and N,N-dimethylformamide (DMF) (10 mL) were placed in a 100 mL flask, and a condenser was connected to create a nitrogen atmosphere inside the flask. The reaction mixture was heated to 100 °C while stirring. After the reaction was complete, deionized water (DIW) was added and the mixture was extracted by microvoltmeter (MC). The extracted organic layer was concentrated by removing water with MgSO4. The resulting solid was dissolved in MC, and then methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain the compound represented by the following chemical formula 1-1. Maldi-tof MS: 986 m / z.

[0181] [ka]

[0182] Synthesis Example 2: Compound represented by chemical formulas 1-2 (1) Production of intermediate 1-2-1

[0183] [ka]

[0184] 10 g of methyl 3-hydroxybenzoate, 17.5 g of 3,4,5,6-tetrachlorophthalonitrile, 10.9 g of K2CO3, and 100 mL of N,N-dimethylformamide (DMF) were placed in a 250 mL flask and stirred while heating to 70°C. After the reaction was complete, the mixture was extracted with EA. After extraction, the concentrated residue was purified by column chromatography. The resulting solid was vacuum-dried to obtain intermediate 1-2-1.

[0185] (2) Production of intermediate 1-2-2

[0186] [ka]

[0187] In a 100 mL flask, intermediate 1-2-1 (4 g), phthalonitrile (1.34 g), 4-tert-butylphthalonitrile (1.93 g), 1,8-diazabicyclo[5.4.0]-7-undecene (3.19 g), and 1-pentanol (20 g) were added and heated to 90°C to dissolve the solid components. Then, zinc acetate (1.93 g) was added and the mixture was stirred while heating to 140°C. After the reaction was complete, methanol was added to form a precipitate, and the resulting solid was filtered and vacuum-dried. The dried solid was purified by column chromatography. After purification, the obtained solid was dissolved in MC, and methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain intermediate 1-2-2.

[0188] (3) Preparation of compounds represented by chemical formulas 1-2 Intermediate 1-2-2 (1.0 g), 2-[2-(dimethylamino(ethoxy)ethanol (0.30 g), and N,N-dimethylformamide (DMF) (10 mL) were placed in a 100 mL flask, and a condenser was connected to create a nitrogen atmosphere inside the flask. The reaction mixture was heated to 100 °C while stirring. After the reaction was complete, DIW was added and extracted with MC. The extracted organic layer was concentrated by removing water with MgSO4. The obtained solid was dissolved with MC, and then methanol was added to crystallize it. The crystallized solid was filtered and vacuum dried to obtain the compound represented by the following chemical formulas 1-2. Maldi-tof MS: 986 m / z.

[0189] [ka]

[0190] Synthesis Example 3: Compounds represented by chemical formulas 1-3 (1) Production of intermediate 1-3-1

[0191] [ka]

[0192] 10 g of methyl 4-hydroxybenzoate, 17.5 g of 3,4,5,6-tetrachlorophthalonitrile, 10.9 g of K2CO3, and 100 mL of N,N-dimethylformamide (DMF) were placed in a 250 mL flask and stirred while heating to 70°C. After the reaction was complete, the mixture was extracted with EA. After extraction, the concentrated residue was purified by column chromatography. The solid obtained by purification was vacuum-dried to obtain intermediate 1-3-1.

[0193] (2) Production of intermediate 1-3-2

[0194] [ka]

[0195] In a 100 mL flask, intermediate 1-3-1 (4 g), phthalonitrile (1.34 g), 4-tert-butylphthalonitrile (1.93 g), 1,8-diazabicyclo[5.4.0]-7-undecene (3.19 g), and 1-pentanol (20 g) were added and heated to 90°C to dissolve the solid components. Then, zinc acetate (1.93 g) was added and the mixture was stirred while heating to 140°C. After the reaction was complete, methanol was added to form a precipitate, and the resulting solid was filtered and vacuum-dried. The dried solid was purified by column chromatography. After purification, the obtained solid was dissolved in MC, and methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain intermediate 1-3-2.

[0196] (3) Preparation of compounds represented by chemical formulas 1-3 Intermediate 1-3-2 (1.0 g), 2-[2-(dimethylamino(ethoxy)ethanol (0.30 g), and N,N-dimethylformamide (DMF) (10 mL) were placed in a 100 mL flask, and a condenser was connected to create a nitrogen atmosphere inside the flask. The reaction mixture was heated to 100 °C while stirring. After the reaction was complete, DIW was added and extracted with MC. The extracted organic layer was concentrated by removing water with MgSO4. The obtained solid was dissolved with MC, and then methanol was added to crystallize it. The crystallized solid was filtered and vacuum dried to obtain the compound represented by the following chemical formulas 1-3. Maldi-tof MS: 986 m / z.

[0197] [ka]

[0198] Synthesis Example 4: Compounds represented by chemical formulas 1-4 (1) Production of intermediate 1-4-1

[0199] [ka]

[0200] Methyl salicylate (10 g), 4-nitrophthalonitrile (11.4 g), K2CO3 (10.9 g), and N,N-dimethylformamide (DMF) (100 mL) were placed in a 250 mL flask and stirred while heating to 70°C. After the reaction was complete, the mixture was extracted with EA. After extraction, the concentrated residue was purified by column chromatography. After purification, the resulting solid was vacuum-dried to obtain intermediate 1-4-1.

[0201] (2) Production of intermediate 1-4-2

[0202] [ka]

[0203] In a 100 mL flask, intermediate 1-4-1 (4 g), phthalonitrile (3.68 g), 4-tert-butylphthalonitrile (2.65 g), 1,8-diazabicyclo[5.4.0]-7-undecene (3.19 g), and 1-pentanol (20 g) were added and heated to 90°C to dissolve the solid components. Then, zinc acetate (2.64 g) was added and the mixture was stirred while heating to 140°C. After the reaction was complete, methanol was added to form a precipitate, and the resulting solid was filtered and vacuum-dried. The dried solid was purified by column chromatography. After purification, the obtained solid was dissolved in MC, and methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain intermediate 1-4-2.

[0204] (3) Preparation of compounds represented by chemical formulas 1-4 Intermediate 1-4-2 (1.0 g), 2-[2-(dimethylamino(ethoxy)ethanol (0.34 g), and N,N-dimethylformamide (DMF) (10 mL) were placed in a 100 mL flask, and a condenser was connected to create a nitrogen atmosphere. The reaction mixture was heated to 100 °C while stirring. After the reaction was complete, DIW was added and extracted with MC. The extracted organic layer was concentrated by removing water with MgSO4. The resulting solid was dissolved with MC, and then methanol was added to crystallize it. The crystallized solid was filtered and vacuum dried to obtain the compound represented by the following chemical formulas 1-4. Maldi-tof MS: 884 m / z.

[0205] [ka]

[0206] Synthesis Example 5: Compounds represented by chemical formulas 1-5 (1) Production of intermediate 1-5-1

[0207] [ka]

[0208] Methyl salicylate (10 g), 3-nitrophthalonitrile (11.4 g), K2CO3 (10.9 g), and N,N-dimethylformamide (DMF) (100 mL) were placed in a 250 mL flask and stirred while heating to 70 °C. After the reaction was completed, extraction was performed with EA. After extraction, the residue obtained by concentration was purified by column chromatography. After purification, the obtained solid was vacuum dried to obtain Intermediate 1-5-1.

[0209] (2) Preparation of Intermediate 1-5-2

[0210]

Chem.

[0211] Intermediate 1-5-1 (4 g), phthalonitrile (3.68 g), 4-tert-butylphthalonitrile (2.65 g), 1,8-diazabicyclo[5.4.0]-7-undecene (3.19 g), and 1-pentanol (20 g) were placed in a 100 mL flask. After heating to 90 °C to dissolve the solid components, zinc acetate (2.64 g) was added and stirred while heating to 140 °C. After the reaction was completed, methanol was added to form a precipitate, and the formed solid was filtered and then vacuum dried. The dried solid was purified by column chromatography. After purification, the obtained solid was dissolved in MC, and then methanol was added for crystallization. The crystallized solid was filtered and vacuum dried to obtain Intermediate 1-5-2.

[0212] (3) Preparation of the compound represented by Chemical Formula 1-5

[0213] Intermediate 1-5-2 (1.0 g), 2-[2-(dimethylamino(ethoxy)ethanol (0.34 g), and N,N-dimethylformamide (DMF) (10 mL) were placed in a 100 mL flask, and a condenser was connected to create a nitrogen atmosphere inside the flask. The reaction mixture was heated to 100 °C while stirring. After the reaction was complete, DIW was added and extracted with MC. The extracted organic layer was concentrated by removing water with MgSO4. The obtained solid was dissolved with MC, and then methanol was added to crystallize it. The crystallized solid was filtered and vacuum dried to obtain the compound represented by the following chemical formulas 1-5. Maldi-tof MS: 884 m / z.

[0214] [ka]

[0215] Synthesis Example 6: Compounds represented by chemical formulas 1-6 Intermediate 1-5-2 (1.0 g), 2-[2-(dimethylamino(ethoxy)ethanol (0.41 g), and N,N-dimethylformamide (DMF) (10 mL) were placed in a 100 mL flask, and a condenser was connected to create a nitrogen atmosphere inside the flask. The reaction mixture was heated to 100 °C while stirring. After the reaction was complete, DIW was added and extracted with MC. The extracted organic layer was concentrated by removing water with MgSO4. The obtained solid was dissolved with MC, and then methanol was added to crystallize it. The crystallized solid was filtered and vacuum dried to obtain the compound represented by the following chemical formulas 1-6. Maldi-tof MS: 912 m / z.

[0216] [ka]

[0217] Synthesis Example 7: Compounds represented by chemical formulas 1-7 (1) Production of intermediate 1-7-1

[0218] [ka]

[0219] In a 250 mL flask, 10.0 g of 4-nitrophthalonitrile, 14.80 g of phthalonitrile, 10.64 g of 4-tert-butylphthalonitrile, 8.79 g of 1,8-diazabicyclo[5.4.0]-7-undecene, and 100 g of 1-pentanol were added and heated to 90°C to dissolve the solid components. Then, 10.60 g of zinc acetate was added and the mixture was stirred while heating to 140°C. After the reaction was complete, methanol was added to form a precipitate, and the resulting solid was filtered and vacuum-dried. The dried solid was purified by column chromatography. After purification, the obtained solid was dissolved in MC, and methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain intermediate 1-7-1.

[0220] (2) Preparation of compounds represented by chemical formulas 1-7 In a 100 mL flask, intermediate 1-7-1 (5.0 g), 2-[2-(dimethylamino(ethoxy)ethanol (1.96 g), K2CO3 (3.05 g), and N,N-dimethylformamide (DMF) (50 mL) were added and heated to 70°C while stirring. After the reaction was complete, methanol was added to form a precipitate. The resulting solid was filtered, vacuum-dried, and then purified by column chromatography. After purification, the solid was vacuum-dried and dissolved in MC. Methanol was then added to crystallize the precipitate. The crystallized solid was filtered and vacuum-dried to obtain the compound represented by the following chemical formulas 1-7. Maldi-tof MS: 764 m / z.

[0221] [ka]

[0222] Synthesis Example 8: Compounds represented by chemical formulas 1-8 (1) Preparation of compounds represented by chemical formulas 1-8

[0223] 100 mL flask was charged with intermediate 1-7-1 (5.0 g), 2-[2-(dimethylamino)ethoxy]ethanol (2.37 g), K2CO3 (3.05 g), and N,N-dimethylformamide (DMF) (50 mL), and stirred while heating to 70 °C. After completion of the reaction, methanol was added to form a precipitate. The resulting solid was filtered, vacuum dried, and then purified by column chromatography. After purification, the dried solid was dissolved in MC, and then methanol was added for crystallization. The crystallized solid was filtered and vacuum dried to obtain a compound represented by the following Chemical Formula 1-8. Maldi-tof MS: 792 m / z.

[0224]

Chemical Formula

[0225] Synthesis Example 9: Compound Represented by 1-9 (1) Production of the Compound Represented by Chemical Formula 1-9 100 mL flask was charged with intermediate 1-7-1 (5.0 g), 2-[2-[2-(dimethylamino)ethoxy]ethoxy]ethanol (2.61 g), K2CO3 (3.05 g), and N,N-dimethylformamide (DMF) (50 mL), and stirred while heating to 70 °C. After completion of the reaction, methanol was added to form a precipitate. It was filtered, vacuum dried, and then purified by column chromatography. After purification, the dried solid was dissolved in MC, and then methanol was added for crystallization. The crystallized solid was filtered and vacuum dried to obtain a compound represented by the following Chemical Formula 1-9. Maldi-tof MS: 808 m / z.

[0226]

Chemical Formula

[0227] Synthesis Example 10: Compound Represented by 1-10 (1) Production of Intermediate 1-10-1 In a 100 mL flask, intermediate 1-7-1 (5.0 g), 2-[2-[2-(dimethylamino)ethoxy]ethoxy]ethanol (3.02 g), K2CO3 (3.05 g), and N,N-dimethylformamide (DMF) (50 mL) were added and stirred while heating to 70°C. After the reaction was complete, methanol was added to form a precipitate. The resulting solid was filtered, vacuum-dried, and then purified by column chromatography. After purification, the vacuum-dried solid was dissolved in MC, and methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain the compound represented by the following chemical formulas 1-10. Maldi-tof MS: 836 m / z.

[0228] [ka]

[0229] Synthesis Example 11: Compounds represented in 1-11 (1) Preparation of intermediate 1-11-1

[0230] [ka]

[0231] In a 250 mL flask, 10.0 g of 3-nitrophthalonitrile, 14.80 g of phthalonitrile, 10.64 g of 4-tert-butylphthalonitrile, 8.79 g of 1,8-diazabicyclo[5.4.0]-7-undecene, and 100 g of 1-pentanol were added and heated to 90°C to dissolve the solid components. Then, 10.60 g of zinc acetate was added and the mixture was stirred while heating to 140°C. After the reaction was complete, methanol was added to form a precipitate, and the resulting solid was filtered and vacuum-dried. The dried solid was purified by column chromatography. After purification, the obtained solid was dissolved in MC, and methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain intermediate 1-11-1.

[0232] (2) Preparation of compounds represented by chemical formulas 1 and 11 In a 100 mL flask, intermediate 1-11-1 (5.0 g), 2-[2-(dimethylamino(ethoxy)ethanol (1.96 g), K2CO3 (3.05 g), and N,N-dimethylformamide (DMF) (50 mL) were added and heated to 70°C while stirring. After the reaction was complete, methanol was added to form a precipitate. The resulting solid was filtered, vacuum-dried, and then purified by column chromatography. After purification, the dried solid was vacuum-dried and dissolved in MC. Methanol was then added to crystallize the solid. The crystallized solid was filtered and vacuum-dried to obtain the compound represented by the following chemical formula 1-11. Maldi-tof MS: 764 m / z.

[0233] [ka]

[0234] Synthesis Example 12: Compounds represented by 1-12 (1) Production of intermediate 1-12-1

[0235] [ka]

[0236] Cyanuric acid chloride (10 g) was dissolved in 100 mL of THF in a 250 mL flask and then cooled in an ice bath. Diethylamine (8.13 g) and triethylamine (24.1 g) were slowly added to this solution over 1 hour. After the addition was complete, the mixture was reacted at room temperature for 1 day, and then the solid components were removed by filtration. The filtrate was concentrated in a vacuum evaporator and then purified by column chromatography. After purification, the obtained solid was vacuum dried to obtain intermediate 1-12-1.

[0237] (2) Production of intermediate 1-12-2

[0238] [ka]

[0239] Intermediate 1-12-1 (10 g) was dissolved in 100 mL of acetone in a 250 mL flask and then cooled in an ice bath. 2-(2-aminoethoxy)ethanol (4.89 g) was slowly added to this solution, followed by the slow addition of sodium bicarbonate (6.60 g) dissolved in 60 mL of distilled water. After the addition was complete, the reaction was carried out under reflux conditions for 1 day, then concentrated in a vacuum evaporator and extracted with EA. After extraction, the concentrated residue was purified by column chromatography. After purification, the mixture was vacuum dried to obtain intermediate 1-12-2.

[0240] (3) Preparation of compounds represented by chemical formulas 1 and 12 Intermediate 1-7-1 (5.0 g), intermediate 1-12-2 (4.81 g), K2CO3 (3.05 g), and N,N-dimethylformamide (DMF) (50 mL) were placed in a 100 mL flask and stirred while heating to 70°C. After the reaction was complete, methanol was added to form a precipitate. The resulting solid was filtered, vacuum-dried, and then purified by column chromatography. After purification, the vacuum-dried solid was dissolved in MC, and methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain the compound represented by the following chemical formula 1-12. Maldi-tof MS: 957 m / z.

[0241] [ka]

[0242] Synthesis Example 13: Compounds represented by 1-13 Intermediate 1-11-1 (5.0 g), intermediate 1-12-2 (4.81 g), K2CO3 (3.05 g), and N,N-dimethylformamide (DMF) (50 mL) were placed in a 100 mL flask and stirred while heating to 70°C. After the reaction was complete, methanol was added to form a precipitate. The resulting solid was filtered, vacuum-dried, and then purified by column chromatography. After purification, the vacuum-dried solid was dissolved in MC, and methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain the compound represented by the following chemical formula 1-13. Maldi-tof MS: 957 m / z.

[0243] [ka]

[0244] Comparative Synthesis Example 1 (1) Production of intermediate C-1

[0245] [ka]

[0246] 4-propylphenol (5g), 4-nitrophthalonitrile (6.35g), K2CO3 (6.08g), and N,N-dimethylformamide (DMF) (25mL) were placed in a 100mL flask and stirred while heating to 70°C. After the reaction was complete, the mixture was extracted with EA. After extraction, the solution was concentrated and purified by column chromatography. After purification, the solution was vacuum-dried to obtain intermediate C-1.

[0247] (2) Preparation of the compound represented by chemical formula C [ka]

[0248] In a 100 mL flask, intermediate C-1 (3 g), phthalonitrile (4.40 g), 1,8-diazabicyclo[5.4.0]-7-undecene (2.08 g), and 1-pentanol (30 g) were placed and heated to 90°C to dissolve the solid components. Then, zinc acetate (2.10 g) was added and the mixture was stirred while heating to 140°C. After the reaction was complete, methanol was added to form a precipitate, and the resulting solid was filtered and vacuum-dried. The dried solid was purified by column chromatography. After purification, the obtained solid was filtered by microclaving, and methanol was added to crystallize it. The crystallized solid was filtered and vacuum-dried to obtain the compound represented by the following chemical formula C. Maldi-tof MS: 711 m / z.

[0249] [ka]

[0250] Production of green pigment dispersion The green pigment dispersions of Production Examples 1-13 and Production Comparative Examples 1 and 2 were prepared by mixing the materials according to the compositions shown in Tables 1-4 below.

[0251] Specifically, a green pigment, a dispersant, a dispersion aid, and a solvent were mixed. 300 parts of zirconia beads (diameter: 0.4 μm) were added to 100 parts by weight of this mixture, and the mixture was shaken and dispersed for 3 hours using a paint shaker. The zirconia beads were then removed by filtration to obtain a green pigment dispersion.

[0252] [Table 1]

[0253] [Table 2]

[0254] The substances used in Tables 1 and 2 above are as follows: Green pigment: CIPIGMENT Green 58 (G58) Dispersant: BYK-LPN6919 (Manufacturer: BYK) Dispersion aids: Compounds from Synthesis Examples 1-13 and Comparative Synthesis Example 1 Solvent: Propylene glycol monomethyl ether acetate (PGMEA)

[0255] 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 and dispersed for 3 hours using a paint shaker. The zirconia beads were then removed by filter.

[0256] Manufacturing of photosensitive resin compositions The photosensitive resin compositions of Examples 1 to 13, Comparative Example 1, and Comparative Example 2 were prepared by mixing the materials according to the compositions shown in Tables 3 and 4 below.

[0257] Specifically, a photosensitive colored resin composition was prepared by mixing a green pigment dispersion, a yellow pigment dispersion, a photopolymerizable monomer, a photopolymerization initiator, a binder resin, and a solvent.

[0258] [Table 3]

[0259] [Table 4]

[0260] The substances used in Tables 3 and 4 above are as follows: (A) Coloring agent Green pigment dispersions: Green pigment dispersions from Production Examples 1-13 and Production Comparative Examples 1 and 2 Yellow pigment dispersion (B) Photopolymerizable monomers Dipentaerythritol hexaacrylate (DPHA, manufactured by Nippon Kayaku Co., Ltd.) (C) Photopolymerization initiator C-1:1,2-Octanedione C-2:2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-ylphenyl)-butan-1-one (D) Binder resin A resin copolymerized with benzyl methacrylate and methacrylic acid in an 85:15 ratio (Mw = 22,000 g / mol) (E) Solvent Propylene glycol monomethyl ether acetate (PGMEA)

[0261] Evaluation Example 1: Dispersion and Dispersion Stability The particle size of solids contained in each photosensitive resin composition, Examples 1-13 and Comparative Examples 1 and 2, was measured using a dynamic light scattering analyzer. The results are shown in Table 5 below.

[0262] Furthermore, the viscosity of each photosensitive resin composition from Examples 1-13 and Comparative Examples 1 and 2 was evaluated using a Brookfield DV-II Pro viscometer and a CPE-52 Spindle at 5 rpm (selected at a Torque value of 50-100%) and 25°C, before and after storage at 23°C for one week. The results are shown in Table 5 below.

[0263] [Table 5]

[0264] According to Table 5 above, it was found that the photosensitive resin compositions of Examples 1 to 13 showed less difference in viscosity, as well as less difference in solid particle size before and after one week of storage, compared to the photosensitive resin compositions of Comparative Examples 1 and 2.

[0265] Evaluation Example 2: Coloring Power, Contrast Ratio, and Residue Characteristics Each of the photosensitive resin compositions from Examples 1-13 and Comparative Examples 1 and 2 was applied to a degreased and cleaned 1 mm thick glass substrate to a thickness of 1-3 μm, and dried on a hot plate at 90°C for 2 minutes to obtain a coating film. Next, the coating film was exposed using a high-pressure mercury lamp with a dominant wavelength of 365 nm, and then dried in a hot air circulating drying oven at 200°C for 5 minutes to obtain a color filter test piece.

[0266] The color coordinates (x, y), luminance (Y), and contrast ratio of the pixel layer were measured using a spectrophotometer (MCPD3000, Otsuka Electronic Co., Ltd.) on a color filter test specimen. The results are shown in Table 6 below.

[0267] For the residue evaluation, a red patterned substrate was prepared on glass coated with 100 nm of SiNx, and EUV cleaning was performed using an Eximer UV asher. Then, the photosensitive resin compositions obtained in Examples 1 to 13 and Comparative Examples 1 and 2 were coated and developed, and the residue on the SiNx substrate was observed with an optical microscope. The results are shown in Table 6 below.

[0268] (Evaluation criteria for residue characteristics) ○: The residue on the organic film cannot be observed with an optical microscope. △: Tiny residue is visible on the organic film. X: Residue is visible over a wide area on the organic film.

[0269] [Table 6]

[0270] Overall, using a dispersion aid represented by chemical formula 1 makes it possible to create a photosensitive resin composition with high pigment dispersibility and dispersion stability, and excellent coloring power and contrast ratio when used in color filters.

[0271] Examples 1 to 13 are presented here as representative examples, but it would also be possible to adjust within the scope of one embodiment to control dispersibility, dispersion stability, coloring power, contrast ratio, etc., to the desired level.

[0272] 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 and the detailed description of the invention, and these also naturally fall within the scope of the present invention.

Claims

1. (A) Coloring agent, (B) photopolymerizable compound, (C) Photopolymerization initiator, (D) Binder resin, and (E) containing a solvent, The colorant comprises a pigment, a dispersant, and a dispersion aid represented by the following chemical formula 1. 【Chemistry 1】 In the aforementioned chemical formula 1, M is either Cu or Zn. R ２１ ~R ２４ , and R ３１ ~R ３４ Each of these is independently a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. R ４１ ~R ４４ Each of these is independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, or a substituted or unsubstituted C6-C20 aryloxy group. The aforementioned R ４１ ~R ４４ At least one of them is A C1-C20 alkoxy group having a substituted or unsubstituted C1-C20 oxyalkylene group as a linking group and a C1-C20 dialkylamino group at its terminus, or A substituent-containing aryloxy group having 6 to 20 carbon atoms, wherein the substituent has a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms as a linking group, and has a dialkylamino group at the terminal end. The above R １１ to R １４ are all hydrogen atoms, a photosensitive resin composition.

2. (A) Coloring agent, (B) photopolymerizable compound, (C) Photopolymerization initiator, (D) Binder resin, and (E) containing a solvent, The colorant comprises a pigment, a dispersant, and a dispersion aid represented by the following chemical formula 1. 【Chemistry 2】 In the aforementioned chemical formula 1, M is either Cu or Zn. R １１ ~R １４ , R ２１ ~R ２４ , and R ３１ ~R ３４ Each of these is independently a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. R ４１ ~R ４４ Each of these is independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, or a substituted or unsubstituted C6-C20 aryloxy group. The aforementioned R ４１ ~R ４４ At least one of them is A C1-C20 alkoxy group having a substituted or unsubstituted C1-C20 oxyalkylene group as a linking group and a C1-C20 dialkylamino group at its terminus, or A substituent-containing aryloxy group having 6 to 20 carbon atoms, wherein the substituent has a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms as a linking group, and has a dialkylamino group at the terminal end. The aforementioned R ２１ ~R ２４ A photosensitive resin composition in which one or two of the elements are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.

3. The aforementioned R ３１ ~R ３４ The photosensitive resin composition according to claim 1 or 2, wherein all atoms are hydrogen atoms.

4. The aforementioned R ４１ ~R ４４ One of these is represented by the following chemical formula L-1 or chemical formula L-2: 【Transformation 3】 In the aforementioned chemical formula L-1 or the aforementioned chemical formula L-2, L １ and L ２ Each of these is independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms. R ５１ These are substituted or unsubstituted amino groups, The photosensitive resin composition according to claim 1 or 2, wherein n is an integer from 0 to 10.

5. The aforementioned R ５１ It is represented by the following chemical formula N, 【Chemistry 4】 In the above chemical formula N, R ６１ and R ６２ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group, R ６１ and R ６２ The photosensitive resin composition according to claim 4, wherein each element exists independently or is bonded to each other to form a condensed ring.

6. The aforementioned R ５１ It is represented by one of the following chemical formulas N-1 to N-6: 【Transformation 5】 【Transformation 6】 Among the chemical formulas N-4 to N-6, X １ ~X ３ Each is independently either N or CH, R ７１ ~R ７７ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group. The photosensitive resin composition according to claim 4, wherein m is an integer from 0 to 4.

7. The photosensitive resin composition according to claim 1 or 2, wherein the dispersion aid represented by chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-13. 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】

8. The photosensitive resin composition according to claim 1 or 2, wherein the dispersion aid represented by the chemical formula 1 has a maximum absorption wavelength of 450 nm to 495 nm.

9. The photosensitive resin composition according to claim 1 or 2, wherein the dispersion aid represented by chemical formula 1 is contained in an amount of 0.01% to 1% by weight relative to the total amount of the photosensitive resin composition.

10. The photosensitive resin composition according to claim 1 or 2, wherein the weight ratio of the dispersion aid represented by the chemical formula 1 to the pigment is 1:20 to 1:

70.

11. The photosensitive resin composition according to claim 1 or 2, wherein the pigment comprises a green pigment, a yellow pigment, or a combination thereof.

12. The photosensitive resin composition is, in relation to the total amount of the photosensitive resin composition, The above (A) coloring agent is present in an amount of 15% to 50% by weight. The above (B) photopolymerizable compound is present in an amount of 0.1% to 10% by weight. The (C) photopolymerization initiator is present in an amount of 0.1% to 5% by weight. The (D) binder resin is present in an amount of 0.5% to 10% by weight, and The photosensitive resin composition according to claim 1 or 2, comprising the solvent (E) in a remaining amount.

13. A photosensitive resin film manufactured using the photosensitive resin composition described in claim 1 or 2.

14. The photosensitive resin film according to claim 13, wherein the photosensitive resin film is a negative photoresist.

15. A color filter comprising the photosensitive resin film described in claim 13.

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