Photosensitive resin composition containing a dispersion aid, photosensitive resin film produced using the composition, and color filter

Abstract

To provide a photosensitive resin composition that exhibits superior tinting power and contrast ratio when used in color filter production, while demonstrating high dispersibility and stable dispersion stability.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, in which the colorant comprises a pigment, a dispersant, and a dispersion aid with a carboxy group asymmetrically substituted on a phthalocyanine core represented by a specific formula.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a photosensitive resin composition containing a dispersion aid, a compound for producing the dispersion aid, a photosensitive resin film produced using the composition, and a color filter. [Background technology]

[0002] Liquid crystal display devices, which are one type of display device, have advantages such as light weight, thinness, low cost, low power consumption, and excellent adhesion to integrated circuits, and their range of use is expanding to include notebook computers, monitors, and TV images.

[0003] Such a liquid crystal display device comprises a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed, and an upper substrate on which an active circuit part consisting of a liquid crystal layer, a thin film transistor, and a storage capacitor layer and an ITO pixel electrode 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 from light, and pixel sections in which multiple colors (usually the three primary colors of red (R), green (G), and blue (B)) are arranged in a predetermined order to form each pixel are stacked in sequence.

[0005] The pigment dispersion method, which is one of the methods for producing color filters, is a method in which a photopolymerizable composition containing a colorant is coated on a transparent substrate provided with a black matrix, and a desired pattern is formed by exposing the composition to light, and then removing the unexposed areas with a solvent and thermally curing the composition, thereby forming a colored thin film.

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

[0007] The pigment dispersion method with these characteristics is actively applied to the production of LCDs for mobile phones, notebook computers, monitors, TVs, etc.

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

[0009] Meanwhile, an image sensor is an image capturing device 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] Color imaging elements used in solid-state imaging elements or complementary metal oxide semiconductors generally perform color separation by placing color filters with filter segments of the additive primary colors of red, green, and blue on the light receiving elements.

[0011] Recently, the size of the color filter patterns attached to such color imaging devices is less than 2 μm, which is 1 / 100 to 1 / 200 times the size of the color filter patterns used in existing LCDs. As a result, increasing resolution and reducing residues are important factors that determine the performance of the device.

[0012] Therefore, in recent years, photosensitive resin compositions for color filters using pigment dispersion methods, which have various advantages, are being required to have not only excellent pattern characteristics but also 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 pigments. [Prior art documents] [Patent documents]

[0013] [Patent Document 1] International Publication No. 2009 / 05125 Summary of the Invention [Problem to be solved by the invention]

[0014] One embodiment is intended to provide a photosensitive resin composition that has high dispersibility and dispersion stability, and also has excellent coloring power and contrast ratio when used to form a color filter.

[0015] Another embodiment is directed to providing a compound for producing a dispersing aid included in a photosensitive resin composition.

[0016] Yet another embodiment provides a photosensitive resin film produced using the photosensitive resin composition.

[0017] Yet another embodiment is to provide a color filter comprising a photosensitive resin film. [Means for solving the problem]

[0018] 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 dispersing aid represented by the following Chemical Formula 1: [Chemical formula 1] [ka] In the above chemical formula 1, M is Cu or Zn; R 11 ~R 14 , R 21 ~R 24 and R 31 ~R 34 are each independently a hydrogen atom, a halogen atom, a hydroxy group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; R 41 and R 42 each independently represents a halogen atom, a hydroxy 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 51 ~R 54 are each independently a hydrogen atom, a halogen atom, or a carboxy group, and R 51 ~R 54 at least one of which is a carboxy group; R 55 is a hydrogen atom or a halogen atom, n and m each independently represent an integer of 0 to 3, provided that 0≦n+m≦3.

[0019] R 51 ~R 54 One of the groups may be a carboxy group, and the remaining three groups may be hydrogen atoms or halogen atoms.

[0020] R 11 ~R 14 may all be hydrogen atoms or all be halogen atoms.

[0021] R 11 ~R 14 Any one of them may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0022] R 21 ~R 24may all be halogen atoms.

[0023] R 21 ~R 24 Any one of them may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0024] R 31 ~R 34 may all be hydrogen atoms or all be halogen atoms.

[0025] R 31 ~R 34 Any one of these may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0026] The dispersion aid represented by Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-26 below. [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]

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[0027] The dispersion aid represented by Chemical Formula 1 may have a maximum absorption wavelength of 450 nm to 495 nm.

[0028] The dispersion aid represented by Chemical Formula 1 may be contained in an amount of 0.01% by weight to 1% by weight based on the total amount of the photosensitive resin composition.

[0029] The weight ratio of the dispersing aid represented by Chemical Formula 1 to the pigment may be 1:20 to 1:70.

[0030] The pigment may include a green pigment, a yellow pigment, or a combination thereof.

[0031] The photosensitive resin composition may contain, relative to the total amount of the photosensitive resin composition, (A) 15% by weight to 50% by weight of a colorant; (B) 0.1% by weight to 10% by weight of a photopolymerizable compound; (C) 0.1% by weight to 5% by weight of a photopolymerization initiator; (D) 0.5% by weight to 10% by weight of a binder resin; and (E) the remaining amount of a solvent.

[0032] In another embodiment, there is provided a compound represented by the following Chemical Formula 2 or Chemical Formula 3 for producing a dispersing aid represented by Chemical Formula 1: [Chemical formula 2] [ka] [Chemical formula 3] [ka] In the above chemical formula 2 and chemical formula 3, M is Cu or Zn; R 11 ~R 14 , R 21 ~R 24 , and R 31 ~R 34 are each independently a hydrogen atom, a halogen atom, a hydroxy group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; R 41 and R 42 each independently represents a halogen atom, a hydroxy 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 51 ~R 54 are each independently a hydrogen atom, a halogen atom, or a carboxy group, and R51 ~R 54 at least one of which is a carboxy group; R 55 is a hydrogen atom or a halogen atom, R 61 ~R 64 are each independently a hydrogen atom, a halogen atom, or an ester group substituted with an alkyl group having 1 to 10 carbon atoms, and R 61 ~R 64 at least one of which is an ester group substituted with an alkyl group having 1 to 10 carbon atoms, n and m each independently represent an integer of 0 to 3, provided that 0≦n+m≦3.

[0033] Yet another embodiment provides a photosensitive resin film produced using the photosensitive resin composition.

[0034] The photosensitive resin film may be a negative photoresist.

[0035] Yet another embodiment provides a color filter including a photosensitive resin film.

[0036] Yet another embodiment provides a display device including a color filter.

[0037] Other specific aspects of the present invention are included in the detailed description below. [Effects of the Invention]

[0038] The photosensitive resin composition according to an embodiment has high dispersibility and dispersion stability, and also has excellent coloring power and contrast ratio when used to form a color filter. Therefore, excellent color filters and display devices can be realized by using the photosensitive resin composition according to an embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0039] DETAILED DESCRIPTION OF THE INVENTION The following detailed description of the present invention is provided by way of example only and is not intended to limit the scope of the present invention, which is defined solely by the scope of the claims that follow.

[0040] Unless otherwise specified in this specification, "substituted" means that at least one hydrogen atom in a compound has been replaced with a halogen atom (F, Cl, Br, I), a hydroxy group, an alkoxy group having 1 to 20 carbon atoms, 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 a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, or a group having 1 to 20 carbon atoms. It means being substituted with 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 substituent that is a combination thereof.

[0041] Unless otherwise specified herein, the terms "heterocycloalkyl group," "heterocycloalkenyl group," "heterocycloalkynyl group," and "heterocycloalkylene group" mean that at least one N, O, S, or P heteroatom is present in the ring system of a cycloalkyl, cycloalkenyl, cycloalkynyl, and cycloalkylene, respectively.

[0042] Unless otherwise specified herein, "(meth)acrylate" means that both "acrylate" and "methacrylate" are applicable.

[0043] Unless otherwise defined herein, "combination" means a mixture or copolymerization, and "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymerization or random copolymerization.

[0044] Unless otherwise defined in the chemical formulas herein, when no chemical bond is drawn at a position where a chemical bond should be drawn, this means that a hydrogen atom is bonded at that position.

[0045] Unless otherwise defined herein, "*" means a moiety connected to the same or different atom or chemical formula.

[0046] Unless otherwise defined herein, "particle size" may refer to the diameter of a particle, and particle size may be the Z-average particle diameter measured by dynamic light scattering.

[0047] (Photosensitive resin composition) 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 dispersing aid represented by the following Chemical Formula 1: [Chemical formula 1] [ka] In the above chemical formula 1, M is Cu or Zn; R 11 ~R 14 , R 21 ~R 24 , and R 31 ~R 34 are each independently a hydrogen atom, a halogen atom, a hydroxy group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; R 41 and R 42 each independently represents a halogen atom, a hydroxy 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 51 ~R 54are each independently a hydrogen atom, a halogen atom, or a carboxy group, and R 51 ~R 54 at least one of which is a carboxy group; R 55 is a hydrogen atom or a halogen atom, n and m each independently represent an integer of 0 to 3, provided that 0≦n+m≦3.

[0048] (A) Colorant In one embodiment, the photosensitive resin composition is a pigment-type photosensitive resin composition, and the colorant contains a pigment. Color filters manufactured from the pigment-type photosensitive resin composition have limitations in brightness and contrast ratio due to the size of the pigment particles.

[0049] Furthermore, for applications in image sensors, resin compositions containing even smaller particles are required for the formation of fine patterns. To achieve this, it is necessary to develop a compound that helps disperse pigments and prevents re-aggregation, and a composition using this compound.

[0050] The dispersing aid represented by Chemical Formula 1 has a phthalocyanine-based core and a carboxyl group asymmetrically substituted on the phthalocyanine-based core.

[0051] The phthalocyanine base interacts with the pigment, and the carboxyl groups asymmetrically substituted on the phthalocyanine base interact with the dispersant or dispersing resin. Thus, the dispersing aid represented by Chemical Formula 1 functions to assist the dispersant in the photosensitive resin composition and enhance the dispersibility and dispersion stability of the pigment.

[0052] Furthermore, the phthalocyanine-based mother nucleus exhibits a blue color. Therefore, the dispersing aid represented by Chemical Formula 1 functions to enhance the coloring power by assisting the colorant in the photosensitive resin composition.

[0053] Overall, the dispersing aid represented by Chemical Formula 1 functions to enhance the dispersibility and dispersion stability of the pigment by aiding the dispersant, and also to enhance the coloring power by aiding the colorant. Therefore, when a photosensitive resin composition containing the dispersing aid represented by Chemical Formula 1 is used in a color filter or display device, it can exhibit further improved coloring power (color reproducibility) and contrast ratio.

[0054] R 11 ~R 14 may each independently be a hydrogen atom, a halogen atom, a hydroxy group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0055] For example, R 11 ~R 14 may all be hydrogen atoms or all be halogen atoms, where the halogen atoms may be chlorine atoms.

[0056] For example, R 11 ~R 14 Any one of R may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. 11 ~R 14 Any one of R may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and the rest may all be hydrogen atoms. 11 ~R 14 One or two of these may be a branched C4 alkyl group (tert-butyl group), and the rest may all be hydrogen atoms.

[0057] R 11 ~R 14 Compared to when all are hydrogen atoms or halogen atoms, R 11 ~R 14 When one or two of the groups are branched C4 alkyl groups (tert-butyl groups), the solubility of the dispersing aid represented by Chemical Formula 1 in the solvent is improved.

[0058] R 11 ~R 14The number of branched C4 alkyl groups (tert-butyl groups) in the formula (1) may depend on the number of N-containing substituents (A) in the dispersing aid represented by formula (1). If there is one N-containing substituent (A) in the dispersing aid represented by formula (1), then R 11 ~R 14 In addition, if there are two N-containing substituents (A) in the dispersing aid represented by Chemical Formula 1, R 11 ~R 14 There may be two branched C4 alkyl groups (tert-butyl groups) among R 11 ~R 14 If there are three or more branched C4 alkyl groups (tert-butyl groups), the chemical resistance of the dispersing aid represented by Chemical Formula 1 may actually decrease.

[0059] R 21 ~R 24 may each independently be a hydrogen atom, a halogen atom, a hydroxy group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0060] Specifically, R 21 ~R 24 may all be halogen atoms, and the halogen atoms may be chlorine atoms.

[0061] In contrast, R 21 ~R 24 Any one of R may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and the rest may all be hydrogen atoms. 21 ~R 24 One or two of these may be a branched C4 alkyl group (tert-butyl group), and the rest may all be hydrogen atoms.

[0062] R 21 ~R 24 Compared to when all atoms are hydrogen atoms, R 21 ~R 24When one or two of the groups are branched C4 alkyl groups (tert-butyl groups), the solubility of the dispersing aid represented by Chemical Formula 1 in the solvent is improved.

[0063] R 21 ~R 24 The number of branched C4 alkyl groups (tert-butyl groups) in the formula (1) may depend on the number of N-containing substituents (A) in the dispersing aid represented by formula (1). If there is one N-containing substituent (A) in the dispersing aid represented by formula (1), then R 21 ~R 24 In addition, if there are two N-containing substituents (A) in the dispersing aid represented by Chemical Formula 1, R 21 ~R 24 There may be two branched C4 alkyl groups (tert-butyl groups) among R 21 ~R 24 If there are three or more branched C4 alkyl groups (tert-butyl groups), the chemical resistance of the dispersing aid represented by Chemical Formula 1 may actually decrease.

[0064] R 31 ~R 34 may each independently be a hydrogen atom, a halogen atom, a hydroxy group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0065] For example, R 31 ~R 34 may all be hydrogen atoms or halogen atoms, where the halogen atoms may be chlorine atoms.

[0066] In contrast, R 31 ~R 34 Any one of R may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and the rest may all be hydrogen atoms. 31 ~R 34 One or two of these may be a branched C4 alkyl group (tert-butyl group), and the rest may all be hydrogen atoms.

[0067] R 31 ~R 34 Compared to when all atoms are hydrogen atoms, R 31 ~R 34 When one or two of the groups are branched C4 alkyl groups (tert-butyl groups), the solubility of the dispersing aid represented by Chemical Formula 1 in the solvent is improved.

[0068] R 31 ~R 34 The number of branched C4 alkyl groups (tert-butyl groups) in the formula (1) may depend on the number of N-containing substituents (A) in the dispersing aid represented by formula (1). If there is one N-containing substituent (A) in the dispersing aid represented by formula (1), then R 31 ~R 34 In addition, if there are two N-containing substituents (A) in the dispersing aid represented by Chemical Formula 1, R 31 ~R 34 There may be two branched C4 alkyl groups (tert-butyl groups) among R 31 ~R 34 If there are three or more branched C4 alkyl groups (tert-butyl groups), the chemical resistance of the dispersing aid represented by Chemical Formula 1 may actually decrease.

[0069] For example, R 41 and R 42 may each independently be a halogen atom, where the halogen atom may be a chlorine atom or a bromine atom.

[0070] The carboxy group asymmetrically substituted on the phthalocyanine mother nucleus is "an aryloxy group having 1 to 20 carbon atoms and substituted at its terminal with one or more carboxy groups." The number of carboxy groups asymmetrically substituted on the phthalocyanine mother nucleus is one or more. This will be explained in detail below.

[0071] R 51 ~R 54 are each independently a hydrogen atom, a halogen atom, or a carboxy group, and R51 ~R 54 At least one of them may be a carboxy group.

[0072] Specifically, R 51 ~R 54 one of which is a carboxy group, and R 55 may be a hydrogen atom or a halogen atom.

[0073] R 51 ~R 54 Only one of R is a carboxy group, and the remaining three may be hydrogen atoms or halogen atoms that are not carboxy groups. 51 ~R 54 If two or more of the groups are carboxy groups, the solubility of the dispersing aid represented by Chemical Formula 1 in a solvent may decrease.

[0074] For example, R 55 may be a hydrogen atom or a halogen atom other than a carboxy group. As described above, the carboxy group is substituted with an aryloxy group having 1 to 20 carbon atoms. In this case, if the substitution position of the carboxy group is ortho or meta, the chemical resistance of the dispersing aid represented by Chemical Formula 1 can be improved, and if the substitution position of the carboxy group is para, the chemical resistance of the dispersing aid represented by Chemical Formula 1 can be reduced.

[0075] For example, the dispersion aid represented by Chemical Formula 1 can be represented by any one of Chemical Formulas 1A to 1C below, but is not necessarily limited thereto. [Chemical formula 1A] [ka] [Chemical formula 1B] [ka] [Chemical formula 1C] [ka] In the above chemical formulas 1A to 1C, the specific explanations for each substituent are as described above.

[0076] For example, representative examples of the dispersing aid represented by Chemical Formula 1 may be as follows, but are not necessarily limited thereto: [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] [ka] [Chemical formula 1-9] [ka] [Chemical formula 1-10]

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[0077] As described above, the dispersion aid represented by Chemical Formula 1 has a phthalocyanine-based mother nucleus that exhibits blue color, and can further improve the coloring power and contrast ratio of the photosensitive resin composition.

[0078] Specifically, the dispersion aid represented by Chemical Formula 1 has a maximum absorption wavelength (λ max ) may be 450 nm to 495 nm.

[0079] The dispersion aid represented by Chemical Formula 1 may be contained in an amount of 0.01% by weight to 1% by weight, specifically 0.05% by weight to 0.5% by weight, for example 0.1% by weight to 0.3% by weight, relative to the total amount of the photosensitive resin composition.

[0080] The weight ratio of the dispersion aid represented by Chemical Formula 1 to the pigment may be 1:10 to 1:70, specifically 1:20 to 1:70, more specifically 1:20 to 1:60, for example 1:20 to 1:50.

[0081] Within each range, the photosensitive resin composition according to an embodiment can have improved dispersibility and dispersion stability while also improving coloring power and contrast ratio.

[0082] The colorant may contain a pigment, and examples of the pigment that can be used include green pigments, blue pigments, red pigments, purple pigments, yellow pigments, and black pigments.

[0083] The red pigment may be, but is not limited to, 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., which may be used alone or in combination of two or more kinds, in the Color Index.

[0084] Examples of purple pigments that can be used include CI Violet Pigment 23 (V.23), CI Violet Pigment 29, Dioxazine Violet, Fast Violet B, Methyl Violet Lake, and Indanthrene Brilliant Violet in the Color Index, and these can be used alone or in combination of two or more, but are not necessarily limited to these.

[0085] The green pigment may be, but is not limited to, CI Green Pigment 7, CI Green Pigment 36, CI Green Pigment 58, CI Green Pigment 59, etc., in the Color Index, which may be used alone or in combination of two or more.

[0086] The blue pigment may be a copper phthalocyanine pigment 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, or CI Blue Pigment 16 in the Color Index, which may be used alone or in combination of two or more, but is not necessarily limited thereto.

[0087] The yellow pigment may be an isoindoline pigment such as CI Yellow Pigment 185 or CI Yellow Pigment 139, a quinophthalone pigment such as CI Yellow Pigment 138, or a nickel complex pigment such as CI Yellow Pigment 150, all of which may be used alone or in combination, but are not limited thereto.

[0088] The black pigment may be aniline black, perylene black, titanium black, carbon black, etc., as listed in the Color Index, and may be used alone or in combination of two or more thereof, but is not necessarily limited to these.

[0089] The pigments may be used alone or in combination of two or more thereof. For example, the pigment may be a green pigment, a yellow pigment, or a mixture thereof.

[0090] The dispersant helps the pigment to be uniformly dispersed in the dispersion, and nonionic, anionic, or cationic dispersants can be used. Specifically, polyalkylene glycols or their esters, polyoxyalkylenes, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, alkylamide alkylene oxide adducts, alkylamines, etc. can be used alone or in combination of two or more.

[0091] The pigment may be contained 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, etc., in addition to the pigment, dispersant, and dispersion aid. The solid pigment may be contained in an amount of 5% by weight to 20% by weight, for example, 8% by weight to 15% by weight, based on the total amount of the pigment dispersion.

[0092] 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 among these, propylene glycol methyl ether acetate can be preferably used.

[0093] The dispersing resin may be an acrylic resin containing a carboxy group, which can not only improve the stability of the pigment dispersion liquid but also the patternability of the pixels.

[0094] The colorant may include a pigment and a dye, and in this case, the resin composition of an embodiment may be a hybrid composition. The dye is not particularly limited, and may include a metal complex dye.

[0095] Metal complex dyes can be compounds with maximum absorbance in the wavelength range of 200nm to 650nm, and in order to match the color coordinates to the combination of dyes, metal complex dyes of any color that are soluble in organic solvents can be used as long as they have absorbance in this range.

[0096] Specifically, the metal complex dye may be a green dye having a maximum absorbance in the wavelength range of 530 nm to 680 nm, a yellow dye having a maximum absorbance in the wavelength range of 200 nm to 400 nm, an orange dye having a maximum absorbance in the wavelength range of 300 nm to 500 nm, a red dye having a maximum absorbance in the wavelength range of 500 nm to 650 nm, or a combination thereof.

[0097] The metal complex dye may be a direct dye, an acid dye, a basic dye, an acid mordant dye, a sulfide dye, a reduction dye, an azoic fuel, a disperse dye, a reactive dye, an oxidation dye, an oil-soluble fuel, an azo dye, an anthraquinone dye, an indigoid dye, a carbonium ion dye, a phthalocyanine dye, a nitro dye, a quinoline dye, a cyanine dye, a polymethine dye, or a combination thereof.

[0098] The metal complex dye may contain at least one metal ion selected from the group consisting of Mg, Ni, Cu, Co, Zn, Cr, Pt, Pd, and Fe.

[0099] Metal complex dyes include CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, and 35; and CI Acid Greens 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, and 109. Dyes: 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, 41 , 43, 53, and the like; green pigments such as CI Pigment Green 7, 36, 58, and the like; and complexes of at least one selected from the group consisting of 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 with a metal ion.

[0100] The dye containing a metal complex may have a solubility of 5 or more, specifically 5 to 10, in the solvent used in the photosensitive resin composition according to one embodiment, i.e., the solvent described below. The solubility can be expressed as the amount (g) of dye that dissolves in 100 g of solvent. When the solubility of the dye containing a metal complex is within the above range, compatibility with other components constituting the photosensitive resin composition according to one embodiment and coloring power can be ensured, and precipitation of the dye can be prevented.

[0101] The solvent may be, for example, propylene glycol monomethyl ether acetate (PGMEA), ethyl lactate (EL), ethylene glycol ethyl acetate (EGA), cyclohexanone, 3-methoxy-1-butanol, or a combination thereof.

[0102] By satisfying the above specific range, the color filter can be usefully used in color filters for LCDs, LEDs, etc. that exhibit high brightness and a high contrast ratio at desired color coordinates.

[0103] The dye containing a metal complex may be contained in an amount of 0.01 to 1% by weight, for example, 0.01 to 0.5% by weight, based on the total amount of the photosensitive resin composition. When the dye containing a metal complex is used in this range, high brightness and contrast ratio can be achieved with desired color coordinates.

[0104] When dyes and pigments are mixed, they can be used in a weight ratio of 0.1:99.9 to 99.9:0.1, specifically 1:9 to 9:1. When mixed in this weight ratio range, chemical resistance and maximum absorption wavelength can be controlled within appropriate ranges, and high brightness and contrast ratio can be achieved with desired color coordinates.

[0105] The colorant may be contained in an amount of 15% to 50% by weight, specifically 20% to 45% by weight, for example 30% to 40% by weight, based on the total amount of the photosensitive resin composition. The colorant may also be contained 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, based on the total amount of the photosensitive resin composition. When the colorant is contained within the above range, excellent coloring effect and developability are achieved.

[0106] (B) Photopolymerizable compound The photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond.

[0107] The photopolymerizable compound has an ethylenically unsaturated double bond, which allows sufficient polymerization to occur upon exposure in the pattern formation step, thereby forming a pattern that is excellent in heat resistance, light resistance, and chemical resistance.

[0108] Specific examples of the photopolymerizable compound 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. acrylate, 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, novolac epoxy(meth)acrylate, and the like.

[0109] 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) manufactured by Toagosei Chemical Industry Co., Ltd.; KAYARAD TC-110S (registered trademark) and TC-120S (registered trademark) manufactured by Nippon Kayaku Co., Ltd.; and V-158 (registered trademark) and V-2311 (registered trademark) manufactured by Osaka Organic Chemical Industry Co., Ltd. Examples of bifunctional esters of (meth)acrylic acid include Aronix M-210 (registered trademark), M-240 (registered trademark), M-6200 (registered trademark), and the like, manufactured by Toagosei Chemical Industry Co., Ltd.; KAYARAD HDDA (registered trademark), HX-220 (registered trademark), R-604 (registered trademark), and the like, manufactured by Nippon Kayaku Co., Ltd.; and V-260 (registered trademark), V-312 (registered trademark), V-335 HP (registered trademark), and the like, manufactured by Osaka Organic Chemical Industry Ltd. Examples of 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), and M-8060 (registered trademark) manufactured by Toagosei Chemical Industry Co., Ltd.; KAYARAD TMPTA (registered trademark), DPCA-20 (registered trademark), DPCA-30 (registered trademark), DPCA-60 (registered trademark), and DPCA-120 (registered trademark) manufactured by Nippon Kayaku Co., Ltd.; and V-295 (registered trademark), V-300 (registered trademark), V-360 (registered trademark), V-GPT (registered trademark), V-3PA (registered trademark), and V-400 (registered trademark) manufactured by Osaka Organic Chemical Industry Co., Ltd. These products can be used alone or in combination of two or more types.

[0110] The photopolymerizable compound can also be used after being treated with an acid anhydride in order to impart better developability.

[0111] The photopolymerizable compound may be contained 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 contained within the above range, sufficient curing occurs upon exposure in the pattern formation step, resulting in excellent reliability and excellent developability in an alkaline developer.

[0112] (C) Photopolymerization initiator The photopolymerization initiator is an initiator commonly used in photosensitive resin compositions, and examples thereof include acetophenone-based compounds, benzophenone-based compounds, thioxanthone-based compounds, benzoin-based compounds, triazine-based compounds, oxime-based compounds, and combinations thereof.

[0113] 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.

[0114] Examples of benzophenone compounds include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

[0115] Examples of thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and 2-chlorothioxanthone.

[0116] Examples of the benzoin-based compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

[0117] Examples of triazine compounds include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-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. 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, and the like.

[0118] Examples of oxime compounds that can be used include O-acyloxime compounds, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, and O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one. Specific examples of O-acyloxime compounds include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-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.

[0119] In addition to the compound, the photopolymerization initiator may also be a carbazole-based compound, a diketone compound, a sulfonium borate-based compound, a diazo-based compound, an imidazole-based compound, a biimidazole-based compound, a fluorene-based compound, or the like.

[0120] Photoinitiators can also be used in conjunction with photosensitizers, which absorb light, become excited, and then transfer that energy to initiate a chemical reaction.

[0121] Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, and dipentaerythritol tetrakis-3-mercaptopropionate.

[0122] The photopolymerization initiator may be contained in an amount of 0.1 to 5% by weight, for example, 1 to 3% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, sufficient curing occurs upon 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 initiator.

[0123] (D) Binder resin The binder resin may include an acrylic resin.

[0124] The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin containing one or more acrylic repeating units.

[0125] The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxy groups, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

[0126] The first ethylenically unsaturated monomer may be contained in an amount of 5% by weight to 50% by weight, for example 10% by weight to 40% by weight, based on the total amount of the acrylic binder resin.

[0127] Examples of the second ethylenically unsaturated monomer 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; carboxylic acid vinyl 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 alone or in combination.

[0128] 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, (meth)acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, etc., but are not limited to these, and these can be used alone or in combination of two or more.

[0129] The binder resin may further include an epoxy-based binder resin.

[0130] The binder resin can further contain an epoxy-based binder resin to improve heat resistance. Examples of the epoxy-based binder resin include, but are not limited to, phenol novolac epoxy resin, tetramethylbiphenyl epoxy resin, bisphenol A epoxy resin, bisphenol F epoxy resin, alicyclic epoxy resin, and combinations thereof.

[0131] Furthermore, the binder resin including the epoxy-based binder resin ensures the dispersion stability of colorants such as pigments described below, and also helps to form pixels with a desired resolution during the development process.

[0132] The epoxy binder resin may be contained in an amount of 1 to 10% by weight, for example, 5 to 10% by weight, based on the total amount of binder resins. When the epoxy binder resin is contained in this range, the film retention rate and chemical resistance can be significantly improved.

[0133] The epoxy equivalent weight of the epoxy binder resin may be 150 g / eq to 200 g / eq. When an epoxy binder resin having an epoxy equivalent weight within the above range is contained in the binder resin, there is an advantageous effect in improving the degree of hardening of the formed pattern and in fixing the colorant within the structure in which the pattern is formed.

[0134] The binder resin may be dissolved in a solvent in a solid form to form a photosensitive resin composition. In this case, the amount of the binder resin in a solid form may be about 0.1% by weight to 30% by weight, for example, 20% by weight to 30% by weight, based on the total amount of the binder resin solution dissolved in the solvent.

[0135] The binder resin may be contained 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 contained within the above range, excellent developability and improved crosslinking properties can be obtained during production of a color filter, resulting in excellent surface smoothness.

[0136] (E) Solvent The solvent may be a substance that is compatible with but does not react with the colorant, binder resin, photopolymerizable compound, and photopolymerization initiator.

[0137] Examples of the solvent include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methyl phenyl 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, 2-heptanone, etc.; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, etc.; lactic acid esters such as methyl lactate and ethyl lactate; oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc.; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate;2-Alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, and methyl 2-ethoxypropionate; 2-Oxy-2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate; Monooxymonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyl esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; Ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate, 2-hydroxypropionic acid alkyl esters Esters such as methyl hydroxy-3-methylbutanoate; ketone acid esters such as ethyl pyruvate; and high-boiling 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.

[0138] Among these, in consideration of compatibility and reactivity, the solvent may be propylene glycol monomethyl ether acetate (PGMEA), n-butyl acetate (n-BA), ethylene glycol dimethyl ether, or a combination thereof.

[0139] The solvent may be contained in an amount of the remainder, for example, 40% by weight to 90% by weight, for example, 45% by weight to 70% by weight, relative to the total amount of the photosensitive resin composition. When the solvent is contained within the above range, the photosensitive resin composition has excellent coatability and can provide a coating film with excellent flatness.

[0140] (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 a (meth)acryloxy 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 generation of residues due to undevelopment.

[0141] The additives can be easily adjusted depending on the desired physical properties.

[0142] The coupling agent may be a silane-based coupling agent, and examples of the silane-based coupling agent include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatepropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, and β-epoxycyclohexylethyltrimethoxysilane, and these may be used alone or in combination of two or more.

[0143] 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.

[0144] Furthermore, the photosensitive resin composition for color filters may further contain a surfactant, such as a fluorine-based surfactant, if necessary.

[0145] Examples of fluorine-based surfactants include, but are not limited to, F-482, F-484, and F-478 manufactured by DIC Corporation.

[0146] The surfactant is preferably contained in an amount of 0.01 to 5% by weight, more preferably 0.01 to 2% by weight, based on the total amount of the photosensitive resin composition. If the amount deviates from the above range, it is not preferable because there is a problem of foreign matter being generated after development.

[0147] Furthermore, the photosensitive resin composition may contain certain amounts of other additives such as antioxidants and stabilizers within the range that does not impair the physical properties.

[0148] (Compounds for manufacturing dispersing aids) According to another embodiment, there is provided a compound for producing a dispersion aid contained in the photosensitive resin composition according to the embodiment.

[0149] The compound for producing the dispersing aid represented by Chemical Formula 1 is represented by Chemical Formula 2 or Chemical Formula 3 below. [Chemical formula 2] [ka] [Chemical formula 3] [ka]

[0150] In the above chemical formula 2 and chemical formula 3, M is Cu or Zn; R 11 ~R 14 , R 21 ~R 24 , and R 31 ~R 34 are each independently a hydrogen atom, a halogen atom, a hydroxy group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, R 41 and R 42 each independently represents a halogen atom, a hydroxy 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 51 ~R 54 are each independently a hydrogen atom, a halogen atom, or a carboxy group, and R 51 ~R 54 at least one of which is a carboxy group; R 55 is a hydrogen atom or a halogen atom, R 61 ~R 64 are each independently a hydrogen atom, a halogen atom, or an ester group substituted with an alkyl group having 1 to 10 carbon atoms, and R 61 ~R 64 at least one of which is an ester group substituted with an alkyl group having 1 to 10 carbon atoms, n and m each independently represent an integer of 0 to 3, provided that 0≦n+m≦3.

[0151] The substituents of the compound for producing a dispersing aid represented by Chemical Formula 2 or Chemical Formula 3 may be as described above.

[0152] (Photosensitive resin film, color filter, and display device) According to yet another embodiment, there is provided a photosensitive resin film manufactured using the photosensitive resin composition according to the embodiment.

[0153] In one embodiment, the photosensitive resin film can be broadly classified into a positive photoresist composition and a negative photoresist composition. In one embodiment, the photosensitive resin film can be a negative photoresist. This has the advantages of not causing coloration due to the photoresist and having relatively higher photosensitivity than a positive photoresist.

[0154] According to yet another embodiment, there is provided a color filter manufactured using the above-described photosensitive resin composition.

[0155] A method for manufacturing a color filter according to one embodiment is as follows.

[0156] The photosensitive resin composition is applied onto a glass substrate 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 to form a photosensitive resin composition layer.

[0157] Next, the substrate on which the photosensitive resin composition layer has been 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 190 nm to 450 nm range, specifically 200 nm to 400 nm range, can be irradiated. The irradiation process can also be performed using a photoresist mask. After the irradiation process, the photosensitive resin composition layer irradiated with the light source is treated with a developer. The unexposed portions of the photosensitive resin composition layer are dissolved, thereby forming the pattern required for the color filter. This process can be repeated for the number of required colors to obtain a color filter with the desired pattern. Furthermore, the image pattern obtained by development in this process can be cured by heating or exposure to actinic radiation, etc., to improve crack resistance, solvent resistance, etc.

[0158] According to yet another embodiment, there is provided a display device including the color filter described above.

[0159] The display device may be a liquid crystal display device, a CMOS image sensor, or the like. [Example]

[0160] The present invention will be described in more detail with reference to the following examples, but the following examples are merely preferred examples of the present invention and are not intended to limit the scope of the present invention.

[0161] (Synthesis example) Synthesis Example 1: Compound represented by chemical formula 1-1 (1) Preparation of Intermediate 1-1-1 [ka]

[0162] Methyl 3-hydroxybenzoate (10 g), 3,4,5,6-tetrachlorophthalonitrile (TCPN) (17.5 g), K2CO3 (10.9 g), and N,N-dimethyl-formamide (DMF) (100 ml) were placed in a 250 ml flask and stirred while heating to 70 °C. After the reaction was completed, the mixture was extracted with EA (ethyl acetate). After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was dried in vacuo to obtain intermediate 1-1-1.

[0163] (2) Preparation of Intermediate 1-1-2 [ka]

[0164] 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 in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (1.93 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, methylene chloride (MC) was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain Intermediate 1-1-2.

[0165] (3) Preparation of the compound represented by chemical formula 1-1 Intermediate 1-1-2 (1.0 g), NaOH (0.29 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was connected. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing water with MgSO4. An appropriate amount of MC was added to the obtained solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-1. [Chemical formula 1-1] [ka] Maldi-tof MS: 870 m / z

[0166] Synthesis Example 2: Compound represented by chemical formula 1-2 (1) Preparation of Intermediate 1-2-1 [ka]

[0167] 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 completed, the mixture was extracted with EA (ethyl acetate). After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was dried in vacuo to obtain intermediate 1-2-1.

[0168] (2) Preparation of Intermediate 1-2-2 [ka]

[0169] 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 placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (1.93 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-2-2.

[0170] (3) Preparation of the compound represented by chemical formula 1-2 Intermediate 2-2 (1.0 g), NaOH (0.29 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the obtained solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-2. [Chemical formula 1-2] [ka] Maldi-tof MS: 870 m / z

[0171] Synthesis Example 3: Compound represented by chemical formula 1-3 (1) Preparation of Intermediate 1-3-1 [ka]

[0172] Methyl 3-hydroxybenzoate (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 completed, the mixture was extracted with EA (ethyl acetate). After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was dried in vacuo to obtain intermediate 1-3-1.

[0173] (2) Preparation of Intermediate 1-3-2 [ka]

[0174] Intermediate 1-3-1 (5 g), phthalonitrile (2.30 g), 4-tert-butylphthalonitrile (3.31 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-3-2.

[0175] (3) Preparation of Compounds Represented by Chemical Formula 1-3 Intermediate 1-3-2 (1.0 g), NaOH (0.33 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the obtained solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-3. [Chemical formula 1-3] [ka] Maldi-tof MS: 768 m / z

[0176] Synthesis Example 4: Compound represented by chemical formula 1-4 (1) Preparation of Intermediate 1-4-1 [ka]

[0177] 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 completed, the mixture was extracted with EA (ethyl acetate). After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was dried in vacuo to obtain intermediate 1-4-1.

[0178] (2) Preparation of Intermediate 1-4-2 [ka]

[0179] Intermediate 1-4-1 (5 g), phthalonitrile (2.30 g), 4-tert-butylphthalonitrile (3.31 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-4-2.

[0180] (3) Preparation of Compounds Represented by Chemical Formula 1-4 Intermediate 1-4-2 (1.0 g), NaOH (0.33 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the obtained solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-4. [Chemical formula 1-4] [ka] Maldi-tof MS: 768 m / z

[0181] Synthesis Example 5: Compound represented by chemical formula 1-5 (1) Preparation of Intermediate 1-5-1 [ka]

[0182] 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, the mixture was extracted with EA (ethyl acetate). After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was dried in vacuo to obtain intermediate 1-5-1.

[0183] (2) Preparation of Intermediate 1-5-2 [ka]

[0184] Intermediate 1-5-1 (5 g), phthalonitrile (2.30 g), 4-tert-butylphthalonitrile (3.31 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-5-2.

[0185] (3) Preparation of Compounds Represented by Chemical Formula 1-5 Intermediate 1-5-2 (1.0 g), NaOH (0.33 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-5. [Chemical formula 1-5] [ka] Maldi-tof MS: 768 m / z

[0186] Synthesis Example 6: Compound represented by chemical formula 1-6 (1) Preparation of Intermediate 1-6-1 [ka]

[0187] Methyl 3-hydroxybenzoate (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, the mixture was extracted with EA (ethyl acetate). After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was dried in vacuo to obtain intermediate 1-6-1.

[0188] (2) Preparation of Intermediate 1-6-2 [ka]

[0189] Intermediate 1-6-1 (5 g), phthalonitrile (2.30 g), 4-tert-butylphthalonitrile (3.31 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-6-2.

[0190] (3) Preparation of Compounds Represented by Chemical Formula 1-6 Intermediate 1-6-2 (1.0 g), NaOH (0.33 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-6. [Chemical formula 1-6] [ka] Maldi-tof MS: 768 m / z

[0191] Synthesis Example 7: Compound represented by chemical formula 1-7 (1) Preparation of Intermediate 1-7-1 [ka]

[0192] Intermediate 1-6-1 (5 g), phthalonitrile (4.60 g), 4-tert-butylphthalonitrile (3.31 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Copper(II) chloride (2.42 g) was then added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-7-1.

[0193] (2) Preparation of the compound represented by formula 1-7 Intermediate 1-7-1 (1.0 g), 10 wt% NaOH aqueous solution (5.10 g), and NMP (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an HCl aqueous solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the obtained solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-7. [Chemical formula 1-7] [ka] Maldi-tof MS: 767 m / z

[0194] Synthesis Example 8: Compound represented by chemical formula 1-8 (1) Preparation of Intermediate 1-8-1 [ka]

[0195] Intermediate 1-3-1 (5 g), TCPN (4.78 g), phthalonitrile (2.31 g), 4-tert-butylphthalonitrile (3.31 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-8-1.

[0196] (2) Preparation of the compound represented by chemical formula 1-8 Intermediate 1-8-1 (1.0 g), 10 wt% NaOH aqueous solution (4.30 g), and NMP (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an HCl aqueous solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the obtained solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-8. [Chemical formula 1-8] [ka] Maldi-tof MS: 904 m / z

[0197] Synthesis Example 9: Compound represented by chemical formula 1-9 (1) Preparation of Intermediate 1-9-1 [ka]

[0198] Intermediate 1-3-1 (5 g), TCPN (9.56 g), 4-tert-Butylphthalonitrile (3.31 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-9-1.

[0199] (2) Preparation of the compound represented by chemical formula 1-9 Intermediate 1-9-1 (1.0 g), NaOH (0.38 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-9. [Chemical formula 1-9] [ka] Maldi-tof MS: 1040 m / z

[0200] Synthesis Example 10: Compound represented by chemical formula 1-10 (1) Preparation of Intermediate 1-10-1 [ka]

[0201] Intermediate 1-3-1 (5 g), TCPN (14.33 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was completed, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the obtained solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-10-1.

[0202] (2) Preparation of the compound represented by formula 1-10 Intermediate 1-10-1 (1.0 g), NaOH (0.35 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-10. [Chemical formula 1-10] [ka] Maldi-tof MS: 1120 m / z

[0203] Synthesis Example 11: Compound represented by chemical formula 1-11 (1) Preparation of Intermediate 1-11-1 [ka]

[0204] Intermediate 1-3-1 (5 g), phthalonitrile (2.30 g), 4-tert-butylphthalonitrile (6.62 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain Intermediate 1-11-1.

[0205] (2) Preparation of the compound represented by chemical formula 1-11 Intermediate 1-11-1 (1.0 g), NaOH (0.48 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-11. [Chemical formula 1-11] [ka] Maldi-tof MS: 824 m / z

[0206] Synthesis Example 12: Compound represented by chemical formula 1-12 (1) Preparation of Intermediate 1-12-1 [ka]

[0207] Intermediate 1-3-1 (5 g), TCPN (4.78 g), 4-tert-Butylphthalonitrile (6.62 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-12-1.

[0208] (2) Preparation of the compound represented by formula 1-12 Intermediate 1-12-1 (1.0 g), NaOH (0.41 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-12. [Chemical formula 1-12] [ka] Maldi-tof MS: 960 m / z

[0209] Synthesis Example 13: Compound represented by chemical formula 1-13 (1) Preparation of Intermediate 1-13-1 [ka]

[0210] Intermediate 1-3-1 (5 g), 4-tert-Butylphthalonitrile (9.93 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-13-1.

[0211] (2) Preparation of the compound represented by chemical formula 1-13 Intermediate 1-13-1 (1.0 g), NaOH (0.45 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-13. [Chemical formula 1-13] [ka] Maldi-tof MS: 880 m / z

[0212] Synthesis Example 14: Compound represented by formula 1-14 (1) Preparation of Intermediate 1-14-1 [ka]

[0213] Intermediate 1-2-1 (5 g), TCPN (3.48 g), phthalonitrile (1.68 g), 4-tert-butylphthalonitrile (2.41 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (3.99 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (2.40 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-14-1.

[0214] (2) Preparation of the compound represented by formula 1-14 Intermediate 1-14-1 (1.0 g), NaOH (0.39 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-14. [Chemical formula 1-14] [ka] Maldi-tof MS: 1006 m / z

[0215] Synthesis Example 15: Compound represented by formula 1-15 (1) Preparation of Intermediate 1-15-1 [ka]

[0216] Intermediate 1-2-1 (5 g), TCPN (6.97 g), 4-tert-Butylphthalonitrile (2.41 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (3.99 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (2.40 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-15-1.

[0217] (2) Preparation of the compound represented by formula 1-15 Intermediate 1-15-1 (1.0 g), NaOH (0.34 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-15. [Chemical formula 1-15] [ka] Maldi-tof MS: 1142 m / z

[0218] Synthesis Example 16: Compound represented by chemical formula 1-16 (1) Preparation of Intermediate 1-16-1 [ka]

[0219] Intermediate 1-2-1 (5 g), TCPN (10.45 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (3.99 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (2.40 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-16-1.

[0220] (2) Preparation of the compound represented by formula 1-16 Intermediate 1-16-1 (1.0 g), NaOH (0.32 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-16. [Chemical formula 1-16] [ka] Maldi-tof MS: 1222 m / z

[0221] Synthesis Example 17: Compound represented by formula 1-17 (1) Preparation of Intermediate 1-17-1 [ka]

[0222] Intermediate 1-2-1 (5 g), phthalonitrile (1.68 g), 4-tert-butylphthalonitrile (4.83 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (3.99 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (2.40 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-17-1.

[0223] (2) Preparation of the compound represented by formula 1-17 Intermediate 1-17-1 (1.0 g), NaOH (0.42 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-17. [Chemical formula 1-17] [ka] Maldi-tof MS: 926 m / z

[0224] Synthesis Example 18: Compound represented by formula 1-18 (1) Preparation of Intermediate 1-18-1 [ka]

[0225] Intermediate 1-2-1 (5 g), TCPN (3.48 g), 4-tert-Butylphthalonitrile (4.83 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (3.99 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (2.40 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-18-1.

[0226] (2) Preparation of the compound represented by formula 1-18 Intermediate 1-18-1 (1.0 g), NaOH (0.37 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-18.

[0227] [Chemical formula 1-18] [ka] Maldi-tof MS: 1062 m / z

[0228] Synthesis Example 19: Compound represented by formula 1-19 (1) Preparation of Intermediate 1-19-1 [ka]

[0229] Intermediate 1-2-1 (5 g), 4-tert-Butylphthalonitrile (7.24 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (3.99 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (2.40 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-19-1.

[0230] (2) Preparation of the compound represented by formula 1-19 Intermediate 1-19-1 (1.0 g), NaOH (0.36 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-19. [Chemical formula 1-19] [ka] Maldi-tof MS: 982 m / z

[0231] Synthesis Example 20: Compound represented by formula 1-20 (1) Preparation of Intermediate 1-20-1 [ka]

[0232] Intermediate 1-4-1 (5 g), TCPN (4.78 g), phthalonitrile (2.30 g), 4-tert-butylphthalonitrile (3.31 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-20-1.

[0233] (2) Preparation of the compound represented by formula 1-20 Intermediate 1-20-1 (1.0 g), NaOH (0.43 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the obtained solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-20. [Chemical formula 1-20] [ka] Maldi-tof MS: 904 m / z

[0234] Synthesis Example 21: Compound represented by formula 1-21 (1) Preparation of Intermediate 1-21-1 [ka] Intermediate 1-4-1 (5 g), TCPN (9.56 g), 4-tert-Butylphthalonitrile (3.31 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-21-1.

[0235] (2) Preparation of the compound represented by formula 1-21 Intermediate 1-21-1 (1.0 g), NaOH (0.38 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-21. [Chemical formula 1-21] [ka] Maldi-tof MS: 1040 m / z

[0236] Synthesis Example 22: Compound represented by formula 1-22 (1) Preparation of Intermediate 1-22-1 [ka] Intermediate 1-4-1 (5 g), TCPN (14.33 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-22-1.

[0237] (2) Preparation of the compound represented by formula 1-22 Intermediate 1-22-1 (1.0 g), NaOH (0.35 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-22. [Chemical formula 1-22] [ka] Maldi-tof MS: 1120 m / z

[0238] Synthesis Example 23: Compound represented by formula 1-23 (1) Preparation of Intermediate 1-23-1 [ka] Intermediate 1-4-1 (5 g), phthalonitrile (2.30 g), 4-tert-butylphthalonitrile (6.62 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-23-1.

[0239] (2) Preparation of the compound represented by formula 1-23 Intermediate 1-23-1 (1.0 g), NaOH (0.48 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-23. [Chemical formula 1-23] [ka] Maldi-tof MS: 824 m / z

[0240] Synthesis Example 24: Compound represented by formula 1-24 (1) Preparation of Intermediate 1-24-1 [ka]

[0241] Intermediate 1-4-1 (5 g), TCPN (4.78 g), 4-tert-Butylphthalonitrile (6.62 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-24-1.

[0242] (2) Preparation of the compound represented by formula 1-24 Intermediate 1-24-1 (1.0 g), NaOH (0.41 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-24. [Chemical formula 1-24] [ka] Maldi-tof MS: 960 m / z

[0243] Synthesis Example 25: Compound represented by formula 1-25 (1) Preparation of Intermediate 1-25-1 [ka]

[0244] Intermediate 1-4-1 (5 g), 4-tert-Butylphthalonitrile (9.93 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (3.30 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-25-1.

[0245] (2) Preparation of the compound represented by formula 1-25 Intermediate 1-25-1 (1.0 g), NaOH (0.45 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-25. [Chemical formula 1-25] [ka] Maldi-tof MS: 880 m / z

[0246] Synthesis Example 26: Compound represented by formula 1-26 (1) Preparation of Intermediate 1-26-1 [ka]

[0247] Intermediate 1-2-1 (5 g), phthalonitrile (3.36 g), 4-tert-butylphthalonitrile (2.41 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (3.99 g), and 1-pentanol (30 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (2.40 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate 1-26-1.

[0248] (2) Preparation of the compound represented by chemical formula 1-26 Intermediate 1-26-1 (1.0 g), NaOH (0.45 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing moisture with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain the compound represented by the following chemical formula 1-26. [Chemical formula 1-26] [ka] Maldi-tof MS: 870 m / z

[0249] Comparative synthesis example 1 (1) Preparation of Intermediate C-1 [ka]

[0250] Methyl glycolate (10 g), 4-nitrophthalonitrile (19.2 g), K2CO3 (30.7 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, the mixture was extracted with EA (ethyl acetate). After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was dried in vacuo to obtain intermediate C-1.

[0251] (2) Preparation of Intermediate C-2 [ka]

[0252] Intermediate C-1 (2 g), phthalonitrile (2.37 g), 4-tert-butylphthalonitrile (1.70 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.63 g), and 1-pentanol (15 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (1.70 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain Intermediate C-2.

[0253] (3) Preparation of Chemical Formula X Intermediate C-2 (2.0 g), NaOH (0.44 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then created. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing water with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain a compound represented by the following chemical formula X. [Chemical formula X] [ka] Maldi-tof MS: 706 m / z

[0254] Reference synthesis example 1 (1) Preparation of Intermediate C-3 [ka] Dimethyl 5-hydroxyisophthalate (10 g), 3,4,5,6-tetrachlorophthalonitrile (12.7 g), K2CO3 (13.2 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, the mixture was extracted with EA (ethyl acetate). After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was dried in vacuo to obtain intermediate C-3.

[0255] (2) Preparation of Intermediate C-4 [ka]

[0256] Intermediate C-3 (2 g), phthalonitrile (1.17 g), 4-tert-butylphthalonitrile (0.84 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (2.77 g), and 1-pentanol (15 g) were placed in a 100 mL flask and heated to 90 °C to dissolve the solid. Then, zinc acetate (0.83 g) was added and the mixture was heated to 140 °C while stirring. After the reaction was complete, precipitation was confirmed with methanol, filtered, and dried under vacuum. The dried solid was purified by column chromatography. After purification, an appropriate amount of MC was added to the resulting solid to dissolve the solid, and then methanol was added to crystallize it. The crystallized solid was filtered and dried under vacuum to obtain intermediate C-4.

[0257] (3) Preparation of Chemical Formula Y Intermediate C-4 (1.0 g), NaOH (0.34 g), and EtOH (10 ml) were placed in a 100 mL flask, and a condenser was attached. A nitrogen atmosphere was then formed. The mixture was heated to 80°C while stirring. After the reaction was completed, an aqueous HCl solution was added to adjust the pH to 5-6, followed by extraction with MC. The extracted organic layer was concentrated by removing water with MgSO4. An appropriate amount of MC was added to the resulting solid and dissolved, followed by crystallization by adding methanol. The crystallized solid was filtered and dried in vacuo to obtain a compound represented by the following chemical formula Y. [Chemical formula Y] [ka] Maldi-tof MS: 914 m / z

[0258] Manufacturing of green pigment dispersion Green pigment dispersions of Production Examples 1 to 26, Production Comparative Example 1 and Production Reference Example 1 were prepared by mixing ingredients in the compositions shown in Tables 1 to 4 below.

[0259] Specifically, a green pigment, a dispersant, a dispersion aid, and a solvent were mixed, and 300 parts of zirconia beads (diameter: 0.4 μm) were added based on 100 parts by weight of this mixture. The mixture was then shaken for 3 hours using a paint shaker to disperse the mixture, and the zirconia beads were removed using a filter to obtain a green pigment dispersion.

[0260] [Table 1]

[0261] [Table 2]

[0262] [Table 3]

[0263] [Table 4]

[0264] The materials used in Tables 1 to 4 above are as follows: Green pigment: CIPIGMENT Green 58 (G58) Dispersant: BYK-LPN6919 (manufacturer: BYK) Dispersing aid: each compound of Synthesis Examples 1 to 26, Comparative Synthesis Example 1, and Reference Synthesis Example 1 Solvent: Propylene glycol monomethyl ether acetate (PGMEA)

[0265] Manufacturing of yellow pigment dispersion 12.0 parts by weight of a yellow pigment (CIPIGMENT Yellow 138), 3.0 parts by weight of a dispersant (BYK-LPN6919, manufacturer: BYK), and 85.0 parts by weight of a solvent (propylene glycol monomethyl ether acetate, PGMEA) were mixed together, and 300 parts by weight of zirconia beads (diameter: 0.4 μm) were added to 100 parts by weight of this mixture. The mixture was then shaken for 3 hours using a paint shaker to disperse the particles, and the zirconia beads were removed using a filter to obtain a yellow pigment dispersion.

[0266] Production of photosensitive resin composition Photosensitive resin compositions of Examples 1 to 26, Comparative Example 1 and Reference Example 1 were produced by mixing ingredients in the compositions shown in Tables 5 to 8 below.

[0267] Specifically, a green pigment dispersion, a yellow pigment dispersion, a photopolymerizable monomer, a photopolymerization initiator, a binder resin, and a solvent were mixed together to produce a photosensitive colored resin composition.

[0268] [Table 5]

[0269] [Table 6]

[0270] [Table 7]

[0271] [Table 8]

[0272] The materials used in Tables 5 to 8 above are as follows: (A) Colorant Green pigment dispersions: green pigment dispersions of Production Examples 1 to 26, Production Comparative Example 1, and Production Reference Example 1 Yellow pigment dispersion (B) Photopolymerizable monomer Dipentaerythritol hexaacrylate (DPHA, Manufacturer: Nippon Kayaku Co., Ltd.) (C) Photopolymerization initiator C-1: 1,2-octanedione C-2: 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one (D) Binder resin Resin (Mw=22,000g / mol) copolymerized with benzyl methacrylate and methacrylic acid in an 85:15 ratio (E) Solvent Propylene glycol monomethyl ether acetate (PGMEA)

[0273] Evaluation example 1: Dispersibility and dispersion stability Using a dynamic light scattering analyzer, the particle size of the solid content contained in each of the photosensitive resin compositions of Examples 1 to 26, Comparative Example 1, and Reference Example 1 was measured, and the results are shown in Table 9 below.

[0274] Furthermore, the viscosity of each of the photosensitive resin compositions of Examples 1 to 26, Comparative Example 1, and Reference Example 1 was evaluated immediately after production and after storage at 23°C for one week using a Brookfield DV-II Pro viscometer and a CPE-52 Spindle at 5 rpm (selected so that the torque value becomes 50 to 100%) and 25°C, and the results are shown in Table 10 below.

[0275] [Table 9]

[0276] From Table 9 above, it can be seen that the photosensitive resin compositions of Examples 1 to 26 not only had smaller differences in particle size of the solid content before and after one week of storage, but also in viscosity, compared to the photosensitive resin compositions of Comparative Example 1 and Reference Example 1.

[0277] Evaluation example 2: Coloring strength and contrast ratio Each of the photosensitive resin compositions of Examples 1 to 26, Comparative Example 1, and Reference Example 1 was applied to a thickness of 1 μm to 3 μm on a degreased and washed glass substrate having a thickness of 1 mm, and then dried on a hot plate at 90° C. for 2 minutes to obtain a coating film. The coating film was then exposed to light using a high-pressure mercury lamp having a dominant wavelength of 365 nm, and then dried in a hot air circulation drying oven at 200° C. for 5 minutes to obtain a color filter test piece.

[0278] The pixel layer was measured for color coordinates (x, y), luminance (Y) and contrast ratio of the color filter test piece using a spectrophotometer (MCPD3000, manufactured by Otsuka Electronics Co., Ltd.), and the results are shown in Table 10 below.

[0279] [Table 10]

[0280] From Table 10 above, it was confirmed that the color filter test pieces of Examples 1 to 6 and Examples 8 to 26 had improved coloring power and contrast ratio compared to the color filter test pieces of Comparative Example 1 and Reference Example 1. On the other hand, since the central metal in the dispersion aid of Example 7 is Cu instead of Zn, the color coordinates are different and therefore the brightness is measured to be lower, but it was also confirmed that the color filter test piece of Example 7, in which the central metal is Cu, also had an excellent contrast ratio like the color filter test pieces of the other Examples.

[0281] Overall, the use of the dispersing aid represented by Chemical Formula 1 can realize a photosensitive resin composition that has high pigment dispersibility and dispersion stability, and also has excellent coloring power and contrast ratio when used in a color filter.

[0282] Here, Examples 1 to 26 are shown as representative examples, but it is possible to adjust within the scope of one embodiment to control dispersibility, dispersion stability, coloring strength, contrast ratio, etc. to desired levels.

[0283] Although the preferred embodiment of the present invention has been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims, the detailed description of the invention, and the accompanying drawings, and it is to be understood that these modifications also fall within the scope of the present invention.

Claims

1. (A) a colorant; (B) photopolymerizable compound; (C) a photopolymerization initiator; (D) a binder resin; and (E) a solvent, The colorant is a photosensitive resin composition comprising a pigment, a dispersant, and a dispersion aid represented by the following Chemical Formula 1: [Chemical formula 1] 【Chemical 1】 In the above chemical formula 1, M is Cu or Zn; R １１ ~R １４ , R ２１ ~R ２４ and R ３１ ~R ３４ are each independently a hydrogen atom, a halogen atom, a hydroxy group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; R ４１ and R ４２ each independently represents a halogen atom, a hydroxy 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 ５１ ~R ５４ are each independently a hydrogen atom, a halogen atom, or a carboxy group, and ５１ ~R ５４ at least one of which is a carboxy group; R ５５ is a hydrogen atom or a halogen atom, n and m each independently represent an integer of 0 to 3, provided that 0≦n+m≦3.

2. The R ５１ ~R ５４ 2. The photosensitive resin composition according to claim 1, wherein one of the groups is a carboxy group and the remaining three groups are hydrogen atoms or halogen atoms.

3. The R １１ ~R １４ The photosensitive resin composition according to claim 1 , wherein all of are hydrogen atoms or all of are halogen atoms.

4. The R １１ ~R １４ 2. The photosensitive resin composition according to claim 1, wherein any one of the groups is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

5. The R ２１ ~R ２４ The photosensitive resin composition according to claim 1 , wherein all of are halogen atoms.

6. The R ２１ ~R ２４ 2. The photosensitive resin composition according to claim 1, wherein any one of the groups is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

7. The R ３１ ~R ３４ The photosensitive resin composition according to claim 1 , wherein all of are hydrogen atoms or all of are halogen atoms.

8. The R ３１ ~R ３４ 2. The photosensitive resin composition according to claim 1, wherein any one of the groups is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

9. The photosensitive resin composition according to claim 1, wherein the dispersion aid represented by Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-26 below. [Chemical formula 1-1] 【Chemistry 2】 [Chemical formula 1-2] 【Chemistry 3】 [Chemical formula 1-3] 【Chemistry 4】 [Chemical formula 1-4] 【Chemistry 5】 [Chemical formula 1-5] 【Chemistry 6】 [Chemical formula 1-6] 【Chemistry 7】 [Chemical formula 1-7] 【Chemistry 8】 [Chemical formula 1-8] 【Chemistry 9】 [Chemical formula 1-9] 【Chemistry 10】 [Chemical formula 1-10] 【Chemistry 11】 [Chemical formula 1-11] 【Chemistry 12】 [Chemical formula 1-12] 【Chemistry 13】 [Chemical formula 1-13] 【Chemistry 14】 [Chemical formula 1-14] 【Chemistry 15】 [Chemical formula 1-15] 【Chemistry 16】 [Chemical formula 1-16] 【Chemistry 17】 [Chemical formula 1-17] 【Chemistry 18】 [Chemical formula 1-18] 【Chemistry 19】 [Chemical formula 1-19] 【Chemistry 20】 [Chemical formula 1-20] 【Chemical Formula 21】 [Chemical formula 1-21] 【Chemical 22】 [Chemical formula 1-22] 【Chemical 23】 [Chemical formula 1-23] 【Chemistry 24】 [Chemical formula 1-24] 【Chemistry 25】 [Chemical formula 1-25] 【Chemical Formula 26】 [Chemical formula 1-26] 【Chemical 27】

10. 2. The photosensitive resin composition according to claim 1, wherein the dispersion aid represented by Chemical Formula 1 has a maximum absorption wavelength of 450 nm to 495 nm.

11. 2. The photosensitive resin composition according to claim 1, wherein the dispersion aid represented by Chemical Formula 1 is contained in an amount of 0.01% by weight to 1% by weight based on the total amount of the photosensitive resin composition.

12. 2. The photosensitive resin composition according to claim 1, wherein the weight ratio of the dispersing aid represented by Formula 1 to the pigment is 1:20 to 1:

70.

13. The photosensitive resin composition of claim 1 , wherein the pigment comprises a green pigment, a yellow pigment, or a combination thereof.

14. The photosensitive resin composition contains, relative to the total amount of the photosensitive resin composition, 15% by weight to 50% by weight of the colorant (A); 0.1% by weight to 10% by weight of the photopolymerizable compound (B); 0.1% by weight to 5% by weight of the (C) photopolymerization initiator; 0.5% by weight to 10% by weight of the (D) binder resin; and The photosensitive resin composition according to claim 1 , further comprising the solvent (E) in a remaining amount.

15. A photosensitive resin film produced using the photosensitive resin composition according to any one of claims 1 to 14.

16. The photosensitive resin film according to claim 15, wherein the photosensitive resin film is a negative photoresist.

17. A color filter comprising the photosensitive resin film according to claim 15.

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