Photosensitive resin composition containing dispersion aid, photosensitive resin film manufactured using same, and color filter

Abstract

The present invention relates to a photosensitive resin composition containing a dispersion aid, a photosensitive resin film manufactured using the photosensitive resin composition, and a color filter.

Description

Photosensitive resin composition containing a dispersing agent, photosensitive resin film and color filter manufactured using the composition

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

[0002]

[0003] Liquid crystal display devices, one of the display devices, have the advantages of being lightweight, thin, low-cost, low-power, and compatible with excellent integrated circuits, and their use is expanding to include notebook computers, monitors, and TVs.

[0004] Such a liquid crystal display device is composed of a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed, and an active circuit portion composed of a liquid crystal layer, a thin film transistor, a storage capacitor layer, and an upper substrate on which an ITO pixel electrode is formed.

[0005] A color filter has a structure in which a black matrix layer is formed in a set pattern on a transparent substrate to block the boundary between pixels, and pixel parts of multiple colors (typically, three primary colors of red (R), green (G), and blue (B) are sequentially stacked in a set order to form each pixel.

[0006] The pigment dispersion method, which is one of the methods for implementing a color filter, is a method in which a colored thin film is formed by repeating a series of processes including coating a photopolymerizable composition containing a coloring agent on a transparent substrate provided with a black matrix, exposing the pattern of the desired shape, removing the unexposed area with a solvent, and heat-curing.

[0007] A colored photosensitive resin composition used in the manufacture of a color filter according to a pigment dispersion method is generally composed of an alkali-soluble resin, a photopolymerization monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives.

[0008] The pigment dispersion method with the above characteristics is actively applied in the manufacture of LCDs for mobile phones, laptops, monitors, TVs, etc.

[0009] However, in recent years, photosensitive resin compositions for color filters utilizing pigment dispersion methods, which offer numerous advantages, are demanding not only superior pattern characteristics but also improved performance. In particular, high color reproducibility, high brightness, and high contrast ratio are urgently required.

[0010] Meanwhile, image sensors refer to image capturing components that create 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.

[0011] Color imaging devices used in solid-state imaging devices or complementary metal oxide semiconductors generally have color filters having filter segments of additive mixed primary colors of red, green, and blue installed on the light-receiving element to perform color separation.

[0012] The pattern size of the color filters currently mounted on these color imaging devices is 2㎛ or less, 1 / 100 to 1 / 200 times smaller than that of conventional LCD color filter patterns. Accordingly, increased resolution and reduced residue are critical factors influencing device performance.

[0013] Accordingly, photosensitive resin compositions for color filters utilizing pigment dispersion methods, which offer numerous advantages, are increasingly demanding not only superior pattern characteristics but also enhanced performance. In particular, there is an urgent need for compositions that enhance pigment dispersion stability while also achieving high tinting power, contrast ratio, and residue characteristics.

[0014]

[0015] One embodiment is to provide a photosensitive resin composition having high dispersibility and dispersion stability, while also having excellent coloring power and contrast ratio when implementing a color filter.

[0016] Another embodiment is to provide a photosensitive resin film manufactured using the photosensitive resin composition.

[0017] Another embodiment is to provide a color filter including the photosensitive resin film.

[0018]

[0019] 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:

[0020] [Chemical Formula 1]

[0021]

[0022] In the above chemical formula 1,

[0023] M is Cu, Co or Zn;

[0024] R 11 Inland R 14 , R 21 Inland R 24 , R 31 Inland R 34 and R 41 Inland R 44are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryloxy group,

[0025] The above R 31 Inland R 34 and R 41 Inland R 44 At least two of which have a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group, and are a C1 to C20 alkoxy group including a sulfonate at the terminal or a C6 to C20 aryloxy group including a sulfonate at the terminal.

[0026] The above R 11 Inland R 14 can be all hydrogen atoms or all halogen atoms.

[0027] The above R 21 Inland R 24 At least one of the groups may be a substituted or unsubstituted C1 to C20 alkyl group.

[0028] The above R 21 Inland R 24 At least one of the groups may be a C1 to C20 alkoxy group having a sulfonate group at the terminal or a C6 to C20 aryloxy group having a sulfonate group at the terminal, while having a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group.

[0029] The above R 31 Inland R 34 At least one of the above R 41 Inland R 44 At least one of the groups may be a C1 to C20 alkoxy group having a sulfonate group at the terminal or a C6 to C20 aryloxy group having a sulfonate group at the terminal, while having a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group.

[0030] The above R31 Inland R 34 One of and the above R 41 Inland R 44 One of them can be represented by any one of the following chemical formulas L-1 to L-4.

[0031] [Chemical formula L-1]

[0032]

[0033] [Chemical formula L-2]

[0034]

[0035] [Chemical formula L-3]

[0036]

[0037] [Chemical formula L-4]

[0038]

[0039] In the above chemical formulas L-1 to L-4,

[0040] L 1 is a substituted or unsubstituted C1 to C4 alkylene group,

[0041] L 2 is a substituted or unsubstituted C1 to C20 alkylene group,

[0042] n is an integer from 1 to 5,

[0043] X is a group 1 element.

[0044] The above R 21 Inland R 24 One of the above R 31 Inland R 34 One of and the above R 41 Inland R 44 One of them may be represented by any one of the chemical formulas L-1 to L-4.

[0045] The dispersing aid represented by the above chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-8 or may include a combination thereof.

[0046] [Chemical Formula 1-1]

[0047] [Correction pursuant to Rule 91, July 2024]

[0048] [Chemical Formula 1-2]

[0049] [Correction pursuant to Rule 91, July 2024]

[0050] [Chemical Formula 1-3]

[0051] [Correction pursuant to Rule 91, July 2024]

[0052] [Chemical Formula 1-4]

[0053] [Correction pursuant to Rule 91, July 2024]

[0054] [Chemical Formula 1-5]

[0055] [Correction pursuant to Rule 91, July 2024]

[0056] [Chemical Formula 1-6]

[0057]

[0058] [Chemical Formula 1-7]

[0059]

[0060] [Chemical Formula 1-8]

[0061] [Correction pursuant to Rule 91, July 2024]

[0062] The dispersing aid represented by the above chemical formula 1 may have a maximum absorption wavelength of 450 nm to 495 nm.

[0063] The dispersing aid represented by the above chemical formula 1 may be included in an amount of 0.01 wt% to 1 wt% based on the total amount of the photosensitive resin composition.

[0064] The weight ratio of the dispersing aid represented by the above chemical formula 1 and the pigment may be 1:5 to 1:20.

[0065] The pigment may include a blue pigment, a green pigment, a purple pigment, a yellow pigment, or a combination thereof.

[0066] The photosensitive resin composition may include, based on the total amount of the photosensitive resin composition, 15 to 50 wt% of the (A) colorant; 0.1 to 10 wt% of the (B) photopolymerizable compound; 0.1 to 5 wt% of the (C) photopolymerization initiator; 0.5 to 10 wt% of the (D) binder resin; and the remainder of the (E) solvent.

[0067] Another embodiment provides a photosensitive resin film manufactured using the photosensitive resin composition.

[0068] The above photosensitive resin film may be a negative photoresist.

[0069] Another embodiment provides a color filter including the photosensitive resin film.

[0070] Another embodiment provides a display device including the color filter.

[0071] Specific details of other aspects of the present invention are included in the detailed description below.

[0072]

[0073] A photosensitive resin composition according to one embodiment has high dispersibility and dispersion stability, while also exhibiting excellent tinting power and contrast ratio when implemented as a color filter. Therefore, using the photosensitive resin composition according to one embodiment, excellent color filters and display devices can be implemented.

[0074]

[0075] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention. The present invention is defined solely by the scope of the claims set forth below.

[0076] Unless otherwise specified herein, "substitution" means that at least one hydrogen atom in a compound is substituted with a halogen atom (F, Cl, Br, I), a hydroxy group, a C1 to C20 alkoxy group, a nitro group, a cyano group, an amine group, an imino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl 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 phosphoric acid or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C6 to C30 aryl group, a C3 to C20 cycloalkyl group, a C3 to C20 cycloalkenyl group, a C3 to C20 cycloalkynyl group, a C2 to C20 heterocycloalkyl group, a C2 to C20 heterocycloalkenyl group, It means substituted with a C2 to C20 heterocycloalkynyl group or a combination thereof.

[0077] 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 compound of cycloalkyl, cycloalkenyl, cycloalkynyl, and cycloalkylene, respectively.

[0078] Unless otherwise specified herein, “(meth)acrylate” means both “acrylate” and “methacrylate”.

[0079] Unless otherwise defined herein, "combination" means a mixture or copolymerization. In addition, "copolymerization" means a block copolymerization or a random copolymerization, and "copolymer" means a block copolymer or a random copolymer.

[0080] Unless otherwise defined in the chemical formulas herein, if a chemical bond is not drawn at a position where a chemical bond should be drawn, it means that a hydrogen atom is bonded at that position.

[0081] Unless otherwise defined herein, “*” means a moiety that is connected to the same or different atoms or chemical formulas.

[0082] Unless otherwise defined herein, “particle size” may mean the diameter of a particle, and the particle size may be the Z-average value of particle diameters measured through dynamic light scattering.

[0083]

[0084] (Photosensitive resin composition)

[0085] 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:

[0086] [Chemical Formula 1]

[0087]

[0088] In the above chemical formula 1,

[0089] M is Cu, Co or Zn;

[0090] R 11 Inland R 14 , R 21 Inland R 24 , R 31 Inland R 34 and R 41 Inland R 44are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryloxy group,

[0091] The above R 31 Inland R 34 and R 41 Inland R 44 At least two of which have a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group, and are a C1 to C20 alkoxy group including a sulfonate at the terminal or a C6 to C20 aryloxy group including a sulfonate at the terminal.

[0092]

[0093] (A) Colorant

[0094] The photosensitive resin composition of one embodiment is a pigment-type photosensitive resin composition, wherein the colorant includes a pigment. Color filters manufactured from the pigment-type photosensitive resin composition have limitations in brightness and contrast ratio resulting from the size of the pigment particles.

[0095] Furthermore, for image sensor applications, resin compositions comprised of smaller particles are required to form fine patterns. To achieve this, compounds that aid pigment dispersion and prevent reaggregation, as well as compositions utilizing these compounds, are needed.

[0096] The dispersing aid represented by the above chemical formula 1 has a phthalocyanine-based parent nucleus and a carboxyl group asymmetrically substituted with respect to the phthalocyanine-based parent nucleus.

[0097] The above phthalocyanine-based nucleus interacts with the pigment, and the sulfonate asymmetrically substituted with respect to the phthalocyanine-based nucleus interacts with the dispersant or dispersing resin. Accordingly, the dispersing aid represented by the above chemical formula 1 functions to assist the dispersant in the photosensitive resin composition, thereby enhancing the dispersibility and dispersion stability of the pigment.

[0098] Moreover, the phthalocyanine-based nucleus exhibits blue or green color. Accordingly, the dispersing aid represented by the chemical formula 1 functions to assist the colorant in the photosensitive resin composition and enhance its coloring power.

[0099] In summary, the dispersing aid represented by the above chemical formula 1 is a dispersing aid that helps the dispersant to enhance the dispersibility and dispersion stability of the pigment, and also functions to help the colorant to enhance the tinting power. Therefore, when a photosensitive resin composition containing the dispersing aid represented by the above chemical formula 1 is implemented as a color filter and display device, it can exhibit further improved tinting power (color reproducibility) and contrast ratio.

[0100] For example, the above R 11 Inland R 14 may all be hydrogen atoms or all may be halogen atoms. Here, the halogen atoms may be chlorine atoms or bromine atoms.

[0101] For example, the above R 21 Inland R 24 At least one of the groups may be a C1 to C20 alkoxy group having a sulfonate group at the terminal or a C6 to C20 aryloxy group having a sulfonate group at the terminal, while having a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group.

[0102] For example, the above R 21 Inland R 24One of them may be a C1 to C20 alkoxy group having a sulfonate group at the terminal or a C6 to C20 aryloxy group having a sulfonate group at the terminal, while having a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group.

[0103] Specifically, the above R 21 Inland R 24 One of them may be a substituted or unsubstituted C1 to C20 alkyl group, and the others may all be hydrogen atoms. For example, the R 21 Inland R 24 One or two of them may be a branched C4 alkyl group (tert-butyl group), and the rest may all be hydrogen atoms.

[0104] The above R 21 Inland R 24 In case all of R are hydrogen atoms, 21 Inland R 24 If one or both of the R groups are branched C4 alkyl groups (tert-butyl groups), the solubility of the dispersing aid represented by the chemical formula 1 in the solvent can be improved, and the dispersing aid can be purified in a high yield, which can be very advantageous in terms of improving economic efficiency. In addition, the R 21 Inland R 24 If one of the R groups is a branched C4 alkyl group (tert-butyl group), 11 Inland R 14 are all hydrogen atoms, and the above R 31 Inland R 34 At least one of and R 41 Inland R 44 At least one of them may be a C1 to C20 alkoxy group including a sulfonate at the terminal or a C6 to C20 aryloxy group including a sulfonate at the terminal, each having a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group.

[0105] However, the above R 21 Inland R 24If there are three or more branched C4 alkyl groups (tert-butyl groups), the chemical resistance of the dispersing aid represented by the chemical formula 1 may be reduced.

[0106] For example, the above R 31 Inland R 34 At least one of the above R 41 Inland R 44 At least one of the groups may be a C1 to C20 alkoxy group having a sulfonate group at the terminal or a C6 to C20 aryloxy group having a sulfonate group at the terminal, while having a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group.

[0107] For example, the above R 31 Inland R 34 One of them may be represented by one of the following chemical formulas L-1 to L-4, and the other may be a hydrogen atom.

[0108] For example, the above R 41 Inland R 44 One of them may be represented by one of the following chemical formulas L-1 to L-4, and the other may be a hydrogen atom.

[0109] For example, the above R 21 Inland R 24 One of the above R 31 Inland R 34 One of and the above R 41 Inland R 44 One of them can be represented by any one of the following chemical formulas L-1 to L-4.

[0110] [Chemical formula L-1]

[0111]

[0112] [Chemical formula L-2]

[0113]

[0114] [Chemical formula L-3]

[0115]

[0116] [Chemical formula L-4]

[0117]

[0118] In the above chemical formulas L-1 to L-4,

[0119] L 1 is a substituted or unsubstituted C1 to C4 alkylene group,

[0120] L 2 is a substituted or unsubstituted C1 to C20 alkylene group,

[0121] n is an integer from 1 to 5,

[0122] X is a group 1 element.

[0123] The number of asymmetrically substituted sulfonates for the above phthalocyanine-based parent nucleus may be one or more, for example, two or more, for example, three or more, for example, four or more. This is described in detail as follows.

[0124] The dispersing aid represented by the above chemical formula 1 has excellent dispersibility and dispersion stability while simultaneously improving the tinting power and contrast ratio because the terminal sulfonate is connected to the phthalocyanine-based nucleus by a linking group containing an “ester group and / or alkylene group” (see the structure of the above chemical formulas L-1 to L-4). Furthermore, in the above chemical formulas L-1 to L-4, L 1 By controlling the number of carbon atoms to less than 5, simultaneous improvements in coloring power, contrast ratio, and residue characteristics can be more effectively achieved.

[0125] For example, the dispersing aid represented by the above chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-8, or may be a combination of any two or more of the following chemical formulas 1-1 to 1-8, but is not necessarily limited thereto.

[0126] [Chemical Formula 1-1]

[0127] [Correction pursuant to Rule 91, July 2024]

[0128] [Chemical Formula 1-2]

[0129] [Correction pursuant to Rule 91, July 2024]

[0130] [Chemical Formula 1-3]

[0131] [Correction pursuant to Rule 91, July 2024]

[0132] [Chemical Formula 1-4]

[0133] [Correction pursuant to Rule 91, July 2024]

[0134] [Chemical Formula 1-5]

[0135] [Correction pursuant to Rule 91, July 2024]

[0136] [Chemical Formula 1-6]

[0137]

[0138] [Chemical Formula 1-7]

[0139]

[0140] [Chemical Formula 1-8]

[0141] [Correction pursuant to Rule 91, July 2024]

[0142] As described above, the dispersing aid represented by the chemical formula 1 has a phthalocyanine-based nucleus that exhibits blue or green color, and thus can further improve the coloring power and contrast ratio of the photosensitive resin composition.

[0143] Specifically, the dispersing aid represented by the above chemical formula 1 has a maximum absorption wavelength (λ max ) may be 450 nm to 495 nm.

[0144] The dispersing aid represented by the above chemical formula 1 may be included in an amount of 0.01 wt% to 1 wt%, specifically 0.05 wt% to 0.8 wt%, for example 0.1 wt% to 0.7 wt%, based on the total amount of the photosensitive resin composition.

[0145] In addition, the weight ratio of the dispersing aid represented by the above chemical formula 1 and the pigment may be 1:5 to 1:20, specifically 1:7 to 1:15, more specifically 1:10 to 1:15, for example 1:10 to 1:13.

[0146] In each of the above ranges, the dispersibility and dispersion stability of the photosensitive resin composition according to the above embodiment can be increased while improving the coloring power and contrast ratio.

[0147] The above colorant may include a pigment, and the pigment may include a green pigment, a blue pigment, a red pigment, a purple pigment, a yellow pigment, a black pigment, etc.

[0148] The above red pigment may be CI Red Pigment 254, CI Red Pigment 255, CI Red Pigment 264, CI Red Pigment 270, CI Red Pigment 272, CI Red Pigment 177, CI Red Pigment 89, etc. within the Color Index, and these may be used alone or in a mixture of two or more, but are not necessarily limited thereto.

[0149] The above purple pigment may be CI Violet Pigment 23 (V.23), CI Violet Pigment 29, Dioxazine Violet, First Violet B, Methyl Violet Lake, Indanthrene Brilliant Violet, etc. within the Color Index, and these may be used alone or in a mixture of two or more, but are not necessarily limited thereto.

[0150] The above green pigment may be CI green pigment 7, CI green pigment 36, CI green pigment 58, CI green pigment 59, etc. within the Color Index, and may be used alone or in a mixture of two or more thereof, but is not necessarily limited thereto.

[0151] The above 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, CI blue pigment 16, etc. within the Color Index, and these may be used alone or in a mixture of two or more, but are not necessarily limited thereto.

[0152] The above yellow pigment may be an isoindoline pigment such as CI Yellow Pigment 185, CI Yellow Pigment 139, etc. within the Color Index, a quinophthalone pigment such as CI Yellow Pigment 138, etc., a nickel complex pigment such as CI Yellow Pigment 150, etc., and these may be used alone or in a mixture of two or more, but are not necessarily limited thereto.

[0153] The above black pigment may be aniline black, perylene black, titanium black, carbon black, etc. within the Color Index, and may be used alone or in a mixture of two or more thereof, but is not necessarily limited thereto.

[0154] The above pigments may be used alone or in combination of two or more. For example, the pigments may include green pigments, blue pigments, purple pigments, or mixtures thereof.

[0155] The above dispersant helps the pigment to be uniformly dispersed in the dispersion, and a nonionic, anionic, or cationic dispersant can be used, respectively. Specifically, polyalkylene glycol or its ester, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid salt, alkyl amide alkylene oxide adduct, alkyl amine, etc. can be used, and these can be used alone or in combination of two or more.

[0156] The pigment may be included in a photosensitive resin composition for a color filter in the form of a dispersion. Such a pigment dispersion may further include a dispersion solvent, a dispersion resin, etc., in addition to the pigment, the dispersant, and the dispersing aid. The solid content of the pigment, excluding the solvent, may be included in an amount of 5 wt% to 20 wt%, for example, 8 wt% to 15 wt%, based on the total amount of the pigment dispersion.

[0157] As the solvent for the above 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.

[0158] The above dispersion resin may use an acrylic resin containing a carboxyl group, which can not only improve the stability of the pigment dispersion but also improve the patternability of the pixels.

[0159] The above colorant may further include a dye while including the pigment, and in this case, the resin composition of the above embodiment may be a hybrid composition. In addition, the dye may include, but is not particularly limited to, a metal complex dye.

[0160] The above metal complex dye can be a compound having maximum absorbance in the wavelength range of 200 nm to 650 nm, and any color metal complex dye that is soluble in an organic solvent can be used as long as it has absorbance in the above range to match the color coordinates to the combination of pigments.

[0161] Specifically, the metal complex dye may be a green dye having a maximum absorbance in a wavelength range of 530 nm to 680 nm, a yellow dye having a maximum absorbance in a wavelength range of 200 nm to 400 nm, an orange dye having a maximum absorbance in a wavelength range of 300 nm to 500 nm, a red dye having a maximum absorbance in a wavelength range of 500 nm to 650 nm, or a combination thereof.

[0162] The above metal complex dye may be a direct dye, an acid dye, a basic dye, an acid mordant dye, a sulfur dye, a reducing dye, an azoic dye, a disperse dye, a reactive dye, an oxidation dye, a useful dye, 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.

[0163] The above metal complex dye may include at least one metal ion selected from the group consisting of Mg, Ni, Cu, Co, Zn, Cr, Pt, Pd and Fe.

[0164] The above metal complex dyes include CI solvent dyes such as CI solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; CI acid dyes such as CI acid green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; CI direct dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, etc.; CI basic dyes such as CI Basic Green 1, etc.; CI mordant dyes such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc.; green pigments such as CI Pigment Green 7, 36, 58; A complex of the metal ion with 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 may be used.

[0165] The dye containing the metal complex may have a solubility of 5 or more, and specifically 5 to 10, in a solvent used in the photosensitive resin composition according to one embodiment, i.e., a solvent described below. The solubility may be obtained by the amount (g) of the dye dissolved in 100 g of the solvent. When the solubility of the dye containing the metal complex is within the above range, compatibility and coloring power with other components forming the photosensitive resin composition according to one embodiment can be secured, and precipitation of the dye can be prevented.

[0166] 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.

[0167] As it has the above specific range, it can be usefully used in color filters such as LCDs and LEDs that exhibit high brightness and high contrast ratio at desired color coordinates.

[0168] The dye containing the metal complex may be included in an amount of 0.01 wt% to 1 wt%, for example, 0.01 wt% to 0.5 wt%, based on the total amount of the photosensitive resin composition. When the dye containing the metal complex is used in the above range, high brightness and contrast ratio can be exhibited at a desired color coordinate.

[0169] When the above dye and the above pigment are mixed and used, they can be mixed and used in a weight ratio of 0.1:99.9 to 99.9:0.1, specifically, in a weight ratio of 1:9 to 9:1. When mixed in the above weight ratio range, chemical resistance and maximum absorption wavelength can be controlled within an appropriate range, and high brightness and contrast ratio can be expressed at a desired color coordinate.

[0170] The colorant may be included in an amount of 15 wt% to 50 wt%, specifically 20 wt% to 45 wt%, for example 30 wt% to 40 wt%, based on the total amount of the photosensitive resin composition. In addition, the colorant may be included in an amount of 5 wt% to 50 wt%, specifically 6 wt% to 40 wt%, for example 7 wt% to 30 wt%, based on the solid content, based on the total amount of the photosensitive resin composition. When the colorant is included within the above range, the coloring effect and developability are excellent.

[0171]

[0172] (B) Photopolymerizable compound

[0173] The above photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond.

[0174] The photopolymerizable compound has the above-described ethylenically unsaturated double bond, and thus can form a pattern with excellent heat resistance, light resistance, and chemical resistance by sufficiently polymerizing upon exposure to light in the pattern forming process.

[0175] Specific examples of photopolymerizable compounds include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol Examples thereof include penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy(meth)acrylate, ethylene glycol monomethyl ether (meth)acrylate, trimethylol propane tri(meth)acrylate, tris(meth)acryloyloxyethyl phosphate, and novolac epoxy (meth)acrylate.

[0176] Examples of commercially available photopolymerizable compounds include the following: An example of the monofunctional ester of (meth)acrylic acid is Aronix M-101 from Toagosei Chemical Co., Ltd. ® , East M-111 ® , East M-114 ® KAYARAD TC-110S from Nihon Kayaku Co., Ltd. ® , Dong TC-120S ® Back; V-158 of Osaka Yuki Kagaku Kogyo Co., Ltd. ® , V-2311 ® Examples of the bifunctional ester of the above (meth)acrylic acid include Aronix M-210 from Toagosei Chemical Co., Ltd. ® , East M-240 ® , East M-6200 ® KAYARAD HDDA from Nihon Kayaku Co., Ltd. ® , Dong HX-220 ® , East R-604® Back; V-260 from Osaka Yuki Kagaku Kogyo Co., Ltd. ® , V-312 ® , V-335 HP ® Examples of the trifunctional ester of the above (meth)acrylic acid include Aronix M-309 from Toagosei Chemical Co., Ltd. ® , East M-400 ® , East M-405 ® , East M-450 ® , East M-710 ® , East M-8030 ® , East M-8060 ® KAYARAD TMPTA from Nihon Kayaku Co., Ltd. ® , East DPCA-20 ® , East-30 ® , East-60 ® , East-120 ® Back; V-295 of Osaka Yuki Kayaku High School Co., Ltd. ® , East-300 ® , East-360 ® , Dong-GPT ® , Dong-3PA ® , East-400 ® The above products can be used alone or in combination of two or more.

[0177] The above photopolymerizable compound may be used by treating it with an acid anhydride to provide better developing properties.

[0178] The photopolymerizable compound may be included in an amount of 0.1 wt% to 10 wt%, specifically 1 wt% to 10 wt%, for example 3 wt% to 7 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerizable compound is included within the above range, sufficient curing occurs upon exposure in the pattern forming process, resulting in excellent reliability and excellent developability in an alkaline developer.

[0179]

[0180] (C) Photopolymerization initiator

[0181] The above photopolymerization initiator is an initiator generally used in a photosensitive resin composition, and for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, an oxime-based compound, or a combination thereof can be used.

[0182] Examples of the above acetophenone compounds include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloro acetophenone, pt-butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc.

[0183] Examples of the above benzophenone compounds include benzophenone, benzoyl benzoate, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc.

[0184] Examples of the above thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2-chlorothioxanthone, etc.

[0185] Examples of the above benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyldimethyl ketal, etc.

[0186] Examples of the above 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, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, Examples thereof include 2-(naphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, and 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine.

[0187] Examples of the above oxime compounds 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, O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one, etc. Specific examples of the O-acyl oxime 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-dione2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-oneoxime-O-acetate, and 1-(4-phenylsulfanylphenyl)-butane-1-oneoxime-O-acetate.

[0188] In addition to the above compound, the photopolymerization initiator may also include a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, a biimidazole compound, a fluorene compound, etc.

[0189] The above photopolymerization initiator may also be used together with a photosensitizer that causes a chemical reaction by absorbing light, becoming excited, and then transferring the energy.

[0190] Examples of the above photosensitizer include tetraethylene glycol bis-3-mercapto propionate, pentaerythritol tetrakis-3-mercapto propionate, dipentaerythritol tetrakis-3-mercapto propionate, and the like.

[0191] The photopolymerization initiator may be included in an amount of 0.1 wt% to 5 wt%, for example, 1 wt% to 3 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the above range, sufficient curing occurs upon exposure in the pattern formation process, thereby obtaining excellent reliability, and the pattern has excellent heat resistance, light resistance, and chemical resistance, and also excellent resolution and adhesion, and can prevent a decrease in transmittance due to unreacted initiator.

[0192]

[0193] (D) Binder resin

[0194] The above binder resin may include an acrylic resin.

[0195] The above 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.

[0196] The above first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxyl groups, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

[0197] The first ethylenically unsaturated monomer may be included in an amount of 5 wt% to 50 wt%, for example, 10 wt% to 40 wt%, based on the total amount of the acrylic binder resin.

[0198] The second ethylenically unsaturated monomer is an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene, vinylbenzylmethylether, etc.; an unsaturated carboxylic acid ester compound 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, phenyl(meth)acrylate, etc.; an unsaturated carboxylic acid aminoalkyl ester compound such as 2-aminoethyl(meth)acrylate, 2-dimethylaminoethyl(meth)acrylate, etc.; a carboxylic acid vinyl ester compound such as vinyl acetate, vinyl benzoate, etc.; an unsaturated carboxylic acid glycidyl ester compound such as glycidyl(meth)acrylate, etc. Examples include cyanide vinyl compounds such as (meth)acrylonitrile; unsaturated amide compounds such as (meth)acrylamide; etc., and these may be used alone or in combination of two or more.

[0199] Specific examples of the above acrylic resin include, but are not limited to, (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., and these may be used alone or in combination of two or more.

[0200] The above binder resin may include an epoxy-based binder resin.

[0201] The above binder resin can improve heat resistance by further including an epoxy-based binder resin. Examples of the epoxy-based binder resin include, but are not limited to, phenol novolac epoxy resin, tetramethyl biphenyl epoxy resin, bisphenol A-type epoxy resin, bisphenol F-type epoxy resin, alicyclic epoxy resin, or combinations thereof.

[0202] Furthermore, the binder resin including the above epoxy-based binder resin ensures dispersion stability of a coloring agent such as a pigment, which will be described later, and helps form pixels of a desired resolution during the developing process.

[0203] The above epoxy-based binder resin may be included in an amount of 1 wt% to 10 wt%, for example, 5 wt% to 10 wt%, based on the total amount of the binder resin. When the epoxy-based binder resin is included in the above range, the film remaining rate and chemical resistance can be significantly improved.

[0204] The epoxy equivalent weight of the above 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 included in the binder resin, there is a beneficial effect of improving the curing degree of the formed pattern and fixing the colorant within the structure in which the pattern is formed.

[0205] The above binder resin can be dissolved in a solvent described below in a solid form to form a photosensitive resin composition. In this case, the binder resin in solid form may be present in an amount of about 0.1 wt% to 30 wt%, for example, 20 wt% to 30 wt%, based on the total amount of the binder resin solution dissolved in the solvent.

[0206] In addition, the binder resin may be included in an amount of 0.1 wt% to 20 wt%, specifically 0.5 wt% to 15 wt%, for example 1 wt% to 10 wt%, based on the total amount of the photosensitive resin composition. When the binder resin is included within the above range, the developability is excellent during the manufacture of a color filter, and the crosslinking property is improved, thereby obtaining excellent surface smoothness.

[0207]

[0208] (E) solvent

[0209] The solvent may be a material that is compatible with, but does not react with, the colorant, the binder resin, the photopolymerizable compound, and the photopolymerization initiator.

[0210] Examples of the solvent include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; carbitols such as methylethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methylethyl 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; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; Alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and 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, and methyl 3-ethoxypropionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and 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-methyl propionic acid esters such as methyl 2-oxy-2-methyl propionic acid, ethyl 2-oxy-2-methyl propionic acid, etc., monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methyl propionic acid alkyls such as methyl 2-methoxy-2-methyl propionic acid, ethyl 2-ethoxy-2-methyl propionic acid, etc.; esters such as ethyl 2-hydroxypropionic acid, ethyl 2-hydroxy-2-methylpropionic acid, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, etc.; Ketone acid esters such as ethyl pyruvate, etc., and also high boiling point solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate can be mentioned.;

[0211] Considering compatibility and reactivity among these, the solvent may be propylene glycol monomethyl ether acetate (PGMEA), n-butyl acetate (n-BA), ethylene glycol dimethyl ether, or a combination thereof.

[0212] The solvent may be included as a remainder, for example, 40 wt% to 90 wt%, for example, 45 wt% to 70 wt%, based on the total amount of the photosensitive resin composition. When the solvent is included within the above range, the photosensitive resin composition has excellent applicability and a coating film with excellent flatness can be obtained.

[0213]

[0214] (F) Other additives

[0215] The photosensitive resin composition may further include 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 to prevent stains or spots during application, improve leveling performance, and prevent the generation of residue due to non-development.

[0216] The above additives can be easily adjusted according to the desired properties.

[0217] The above coupling agent may be a silane coupling agent, and examples of the silane coupling agent include trimethoxysilyl benzoic acid, γ-methacryloxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, γ-glycidoxy propyl trimethoxysilane, β-(epoxycyclohexyl)ethyl trimethoxysilane, etc., and these may be used alone or in combination of two or more.

[0218] The above silane coupling agent can be specifically used in an amount of 0.01 to 1 part by weight based on 100 parts by weight of the photosensitive resin composition.

[0219] In addition, the photosensitive resin composition for the color filter may further include a surfactant, such as a fluorinated surfactant, as needed.

[0220] Examples of the above fluorinated surfactants include, but are not limited to, DIC's F-482, F-484, and F-478.

[0221] The above surfactant is preferably included in an amount of 0.01 wt% to 5 wt%, and more preferably 0.01 wt% to 2 wt%, based on the total amount of the photosensitive resin composition. If the amount exceeds the above range, the problem of foreign substances being generated after development may arise, which is not preferable.

[0222] In addition, the photosensitive resin composition may have a certain amount of other additives such as antioxidants and stabilizers added to it, as long as the physical properties are not impaired.

[0223]

[0224] (photosensitive resin film, color filter and display device)

[0225] According to another embodiment, a photosensitive resin film manufactured using a photosensitive resin composition according to one embodiment is provided.

[0226]

[0227] The photosensitive resin film of one embodiment is largely divided into a positive photoresist composition and a negative photoresist composition.

[0228] The photosensitive resin film of one embodiment may be a negative photoresist. This has the advantage of not causing coloring by the photoresist and having relatively higher photosensitivity than a positive photoresist.

[0229]

[0230] According to another embodiment, a color filter manufactured using the photosensitive resin composition described above is provided.

[0231]

[0232] A method for manufacturing a color filter of one embodiment is as follows.

[0233] The photosensitive resin composition described above is applied to a glass substrate using an appropriate method such as spin coating, roller coating, or spray coating, for example, to a thickness of 0.5 um to 10 um, thereby forming a photosensitive resin composition layer.

[0234] Next, light is irradiated on the substrate on which the photosensitive resin composition layer is formed so as to form a pattern required for the color filter. The light source used for the irradiation may be UV, electron beam, or X-ray, and for example, UV in the range of 190 nm to 450 nm, specifically 200 nm to 400 nm, may be irradiated. The irradiation process may further be performed using a photoresist mask. After performing the irradiation process as described above, the photosensitive resin composition layer irradiated with the light source is treated with a developing solution. At this time, the unexposed portion of the photosensitive resin composition layer is dissolved, thereby forming a pattern required for the color filter. By repeating this process according to the number of required colors, a color filter having a desired pattern can be obtained. In addition, if the image pattern obtained by development in the above process is cured again by heating or irradiating with active rays, etc., crack resistance, solvent resistance, etc. can be improved.

[0235]

[0236] According to another embodiment, a display device including the aforementioned color filter is provided.

[0237] The above display device may be a liquid crystal display device, a CMOS image sensor, or the like.

[0238]

[0239] Hereinafter, the present invention will be described in more detail with reference to examples. However, the following examples are only preferred examples of the present invention, and the present invention is not limited to the following examples.

[0240]

[0241] (Synthetic example)

[0242] Synthesis Example 1: Compound represented by Chemical Formula 1-1

[0243] (1) Preparation of intermediate 1-1

[0244]

[0245] In a 500 ml flask, add methyl 3-hydroxybenzoate (50 g), 4-nitrophthalonitrile (569 g), K2CO3 (68.1 g), and N,N-dimethylformamide (DMF) (250 ml), heat to 70°C, and stir. After the reaction is complete, extract with EA (ethyl acetate). After extraction, concentrate, and purify by column chromatography. After purification, vacuum dry to obtain intermediate 1-1.

[0246] (2) Preparation of intermediate 1-2

[0247]

[0248] In a 250 mL flask, add intermediate 1-1 (20 g), phthalonitrile (4.60 g), 4-tert-Butylphthalonitrile (6.62 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (100 g), heat to 90°C until the solid dissolves, then add copper (II) chloride (4.83 g) and heat to 140°C while stirring. After the reaction is complete, check for precipitation with methanol, filter, and dry under vacuum. Purify the dried solid by column chromatography. After purification, add an appropriate amount of MC (Dichloromethane) to the solid obtained to dissolve the solid, and then add methanol to crystallize. Filter the crystallized solid and dry under vacuum to obtain intermediate 1-2.

[0249] (3) Preparation of intermediates 1-3

[0250]

[0251] In a 250 mL flask, add the intermediate 1-2 (5 g), 30 g of THF (Tetrahydrofuran), and 30 g of ethyl alcohol, and add 70 g of a 10 wt% NaOH aqueous solution while stirring. After the addition is complete, heat to 65°C while stirring. After the reaction is complete, remove THF and ethyl alcohol using an evaporator, and then add 70 g of a 20 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, filter again to remove unreacted dyes and impurities, and then dry in vacuum to obtain intermediate 1-3.

[0252] (4) Preparation of a compound represented by chemical formula 1-1

[0253]

[0254] In a 100 mL flask, add 1,4-Butanesultone (9.03 g), K2CO3 (4.58 g), and N,N-dimethylformamide (DMF) (20 ml) to the intermediate 1-3 (3 g) and heat to 70°C while stirring. After the reaction is complete, add 150 g of a 10 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, and filter again to remove impurities to obtain the compound represented by the chemical formula 1-1 (Maldi-tof MS: 1173 m / z).

[0255]

[0256] Synthesis Example 2: Compound represented by Chemical Formula 1-2

[0257] (1) Preparation of intermediate 2-1

[0258]

[0259] In a 250 mL flask, add intermediate 1-1 (30 g), phthalonitrile (4.60 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.47 g), and 1-pentanol (100 g), heat to 90°C until the solid dissolves, then add copper (II) chloride (4.83 g) and heat to 140°C while stirring. After the reaction is complete, check for precipitation with methanol, filter, and vacuum-dry. Purify the dried solid by column chromatography. Add an appropriate amount of MC to the solid obtained after purification to dissolve the solid, and then add methanol to crystallize. Filter the crystallized solid and vacuum-dry to obtain intermediate 2-1.

[0260] (2) Preparation of intermediate 2-2

[0261]

[0262] In a 250 mL flask, add the intermediate 2-1 (5 g), 30 g of THF (Tetrahydrofuran), and 30 g of ethyl alcohol, and add 70 g of a 10 wt% NaOH aqueous solution while stirring. After the addition is complete, heat to 65°C while stirring. After the reaction is complete, remove THF and ethyl alcohol using an evaporator, and then add 70 g of a 20 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, filter again to remove unreacted dye and impurities, and then dry in vacuum to obtain intermediate 2-2.

[0263] (3) Preparation of a compound represented by chemical formula 1-2

[0264]

[0265] In a 100 mL flask, add 1,4-Butanesultone (12.45 g), K2CO3 (6.32 g), and N,N-dimethylformamide (DMF) (20 ml) to the intermediate 2-2 (3 g) and heat to 70°C while stirring. After the reaction is complete, add 150 g of a 10 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, and filter again to remove impurities to obtain the compound represented by the chemical formula 1-2 (Maldi-tof MS: 1388 m / z).

[0266]

[0267] Synthesis Example 3: Compound represented by Chemical Formula 1-3

[0268] (1) Preparation of intermediate 3-1

[0269]

[0270] In a 500 ml flask, add Dimethyl 5-Hydroxyisophthalate (50 g), 4-Nitro-phthalonitrile (41.2 g), K2CO3 (49.3 g), and N,N-dimethylformamide (DMF) (250 ml), heat to 70°C, and stir. After the reaction is complete, extract with EA (ethyl acetate). After extraction, concentrate, and purify by column chromatography. After purification, vacuum dry to obtain intermediate 3-1.

[0271] (2) Preparation of intermediate 3-2

[0272]

[0273] In a 250 mL flask, add intermediate 3-1 (20 g), phthalonitrile (3.81 g), 4-tert-Butyl-phthalonitrile (5.48 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (4.53 g), and 1-pentanol (100 g), heat to 90°C until the solid dissolves, then add copper(II) chloride (4.00 g) and heat to 140°C while stirring. After the reaction is complete, check for precipitation with methanol, filter, and dry under vacuum. Purify the dried solid by column chromatography. After purification, add an appropriate amount of MC (Dichloromethane) to the solid obtained to dissolve the solid, and then add methanol to crystallize. Filter the crystallized solid and dry under vacuum to obtain intermediate 3-2.

[0274] (3) Preparation of intermediate 3-3

[0275]

[0276] In a 250 mL flask, add the intermediate 3-2 (5 g), 30 g of THF (Tetrahydrofuran), and 30 g of ethyl alcohol, and add 70 g of a 10 wt% NaOH aqueous solution while stirring. After the addition is complete, heat to 65°C while stirring. After the reaction is complete, remove THF and ethyl alcohol using an evaporator, and then add 70 g of a 20 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, filter again to remove unreacted dye and impurities, and then dry in vacuum to obtain intermediate 3-3.

[0277] (4) Preparation of a compound represented by chemical formula 1-3

[0278]

[0279] In a 100 mL flask, add 1,4-Butanesultone (16.47 g), K2CO3 (8.36 g), and N,N-dimethylformamide (DMF) (20 ml) to the intermediate 3-3 (3 g) and heat to 70°C while stirring. After the reaction is complete, add 150 g of a 10 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, and filter again to remove impurities to obtain a compound represented by the chemical formula 1-3 (Maldi-tof MS: 1531 m / z).

[0280]

[0281] Synthesis Example 4: Compound represented by Chemical Formula 1-4

[0282] (1) Preparation of intermediate 4-1

[0283]

[0284] In a 500 ml flask, add the above Ethyl 6-Hydroxyhexanoate (50 g), 4-Nitrophthalonitrile (54.0 g), K2CO3 (64.7 g), and N,N-dimethylformamide (DMF) (250 ml), heat to 80°C, and stir. After the reaction is complete, extract with MC (Dichloromethane). After extraction, concentrate, and purify by column chromatography. After purification, vacuum dry to obtain intermediate 4-1.

[0285] (2) Preparation of intermediate 4-2

[0286]

[0287] In a 250 mL flask, add intermediate 4-1 (20 g), phthalonitrile (4.47 g), 4-tert-Butylphthalonitrile (6.43 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.32 g), and 1-pentanol (100 g), heat to 90°C until the solid dissolves, then add copper (II) chloride (4.70 g) and heat to 140°C while stirring. After the reaction is complete, check for precipitation with methanol, filter, and dry under vacuum. Purify the dried solid by column chromatography. After purification, add an appropriate amount of MC (Dichloromethane) to the solid obtained to dissolve the solid, and then add methanol to crystallize. Filter the crystallized solid and dry under vacuum to obtain intermediate 4-2.

[0288] (3) Preparation of intermediate 4-3

[0289]

[0290] In a 250 mL flask, add the above intermediate 4-2 (5 g), 30 g of THF (Tetrahydrofuran), and 30 g of ethyl alcohol, and add 70 g of a 20 wt% NaOH aqueous solution while stirring. After the addition is complete, heat to 65°C while stirring. After the reaction is complete, remove THF and ethyl alcohol using an evaporator, and then add 70 g of a 20 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, filter again to remove unreacted dye and impurities, and then dry under vacuum to obtain intermediate 4-3.

[0291] (4) Preparation of a compound represented by chemical formula 1-4

[0292]

[0293] In a 100 mL flask, add 1,4-Butanesultone (9.15 g), K2CO3 (4.65 g), and N,N-dimethylformamide (DMF) (20 ml) to the intermediate 4-3 (3 g) and heat to 70°C while stirring. After the reaction is complete, add 150 g of a 10 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, and filter again to remove impurities to obtain the compound represented by the chemical formula 1-4 (Maldi-tof MS: 1161 m / z).

[0294]

[0295] Synthesis Example 5: Compound represented by Chemical Formula 1-5

[0296] (1) Preparation of intermediate 5-1

[0297]

[0298] In a 250 mL flask, add intermediate 4-1 (30 g), phthalonitrile (4.47 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.32 g), and 1-pentanol (100 g), heat to 90°C until the solid dissolves, then add copper (II) chloride (4.70 g) and heat to 140°C while stirring. After the reaction is complete, check for precipitation with methanol, filter, and dry under vacuum. Purify the dried solid by column chromatography. Add an appropriate amount of MC to the solid obtained after purification to dissolve the solid, and then add methanol to crystallize. Filter the crystallized solid and dry under vacuum to obtain intermediate 5-1.

[0299] (2) Preparation of intermediate 5-2

[0300]

[0301] In a 250 mL flask, add 5 g of the above intermediate 5-1, 30 g of THF (Tetrahydrofuran), and 30 g of ethyl alcohol, and add 70 g of a 10 wt% NaOH aqueous solution while stirring. After the addition is complete, heat to 65°C while stirring. After the reaction is complete, remove THF and ethyl alcohol using an evaporator, and then add 70 g of a 20 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, filter again to remove unreacted dye and impurities, and then vacuum dry to obtain intermediate 5-2.

[0302] (3) Preparation of a compound represented by chemical formula 1-5

[0303]

[0304] In a 100 mL flask, add 1,4-Butanesultone (9.15 g), K2CO3 (4.65 g), and N,N-dimethylformamide (DMF) (20 ml) to the intermediate 5-2 (3 g) and heat to 70°C while stirring. After the reaction is complete, add 150 g of a 10 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, and filter again to remove impurities to obtain the compound represented by the chemical formula 1-5 (Maldi-tof MS: 1370 m / z).

[0305]

[0306] Synthesis Example 6: Compound represented by Chemical Formula 1-6

[0307] (1) Preparation of intermediate 6-1

[0308]

[0309] In a 250 ml flask, add 1,4-Butanediol (10 g), 4-Nitrophthalonitrile (19.21 g), K2CO3 (30.67 g), and N,N-dimethylformamide (DMF) (100 ml), heat to 70°C, and stir. After the reaction is complete, extract with EA (ethyl acetate). After extraction, concentrate, and purify by column chromatography. After purification, vacuum dry to obtain intermediate 6.

[0310] Add 100 g of bromic acid (approximately 48 wt%) to 10 g of the above intermediate 6, connect a condenser, and heat to 80°C while stirring to form a nitrogen atmosphere. After the reaction is complete, extract with MC (Dichloromethane). Remove moisture from the extracted organic layer with MgSO4, concentrate, and dry in vacuum to obtain intermediate 6-1.

[0311] (2) Preparation of intermediate 6-2

[0312]

[0313] In a 250 mL flask, add intermediate 6-1 (10 g), phthalonitrile (9.18 g), 4-tert-Butylphthalonitrile (6.60 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (5.45 g), and 1-pentanol (100 g), heat to 90°C until the solid dissolves, then add copper (II) chloride (4.82 g) and heat to 140°C while stirring. After the reaction is complete, check for precipitation with methanol, filter, and dry under vacuum. Purify the dried solid by column chromatography. After purification, add an appropriate amount of MC (Dichloromethane) to the solid obtained to dissolve the solid, and then add methanol to crystallize. Filter the crystallized solid and dry under vacuum to obtain intermediate 6-2.

[0314] (3) Preparation of a compound represented by chemical formula 1-6

[0315]

[0316] In a 250 mL flask, add the intermediate 6-2 (5 g), sodium sulfite (4.05 g), THF (Tetrahydrofuran) 30 g, and DIW 30 g, and heat to 65°C while stirring. After the reaction is complete, remove THF using an evaporator, and then add 70 g of a 20 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, and filter again to remove unreacted dye and impurities. The solid thus obtained is vacuum-dried to obtain a compound represented by the chemical formula 1-6 (Maldi-tof MS: 933 m / z).

[0317]

[0318] Synthesis Example 7: Compound represented by Chemical Formula 1-7

[0319] (1) Preparation of intermediate 7-1

[0320]

[0321] In a 250 mL flask, add intermediate 6-1 (20 g), phthalonitrile (3.06 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (3.64 g), and 1-pentanol (100 g), heat to 90°C until the solid dissolves, then add copper(II) chloride (3.21 g) and heat to 140°C while stirring. After the reaction is complete, check for precipitation with methanol, filter, and dry under vacuum. Purify the dried solid by column chromatography. Add an appropriate amount of MC to the solid obtained after purification to dissolve the solid, and then add methanol to crystallize. Filter the crystallized solid and dry under vacuum to obtain intermediate 7-1.

[0322] (2) Preparation of a compound represented by chemical formula 1-7

[0323]

[0324] In a 250 mL flask, add the intermediate 7-1 (5 g), sodium sulfite (5.51 g), THF (Tetrahydrofuran) 30 g, and DIW 30 g, and heat to 65°C while stirring. After the reaction is complete, remove THF using an evaporator, and then add 70 g of a 20 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, and filter again to remove unreacted dye and impurities. The solid thus obtained is vacuum-dried to obtain a compound represented by the following chemical formula 1-7 (Maldi-tof MS: 1028 m / z).

[0325]

[0326] Synthesis Example 8: Compound represented by Chemical Formula 1-8

[0327] (1) Preparation of intermediate 8-1

[0328]

[0329] Add 2-(4-Hydroxyphenyl)ethanol (10g) and hydrobromic acid (100g) to a 250ml flask, connect a condenser, and create a nitrogen atmosphere. Heat to 80℃ and stir. After the reaction is complete, extract with MC (Dichloromethane). Remove moisture from the extracted organic layer with MgSO4, concentrate, and dry in vacuum to obtain intermediate 8.

[0330] In a 100 ml flask, add the intermediate 8 (5 g), 4-Nitrophthalonitrile (4.31 g), K2CO3 (6.19 g), and N,N-dimethylformamide (DMF) (25 ml), heat to 70°C, and stir. After the reaction is complete, extract with MC (Dichloromethane). After extraction, concentrate, and purify by column chromatography. After purification, vacuum dry to obtain intermediate 8-1.

[0331] (2) Preparation of intermediate 8-2

[0332]

[0333] In a 250 mL flask, add intermediate 8-1 (20 g), phthalonitrile (3.92 g), 4-tert-Butylphthalonitrile (5.63 g), 1,8-Diazabicyclo[5.4.0]-7-undecene (4.65 g), and 1-pentanol (100 g), heat to 90°C until the solid dissolves, then add copper (II) chloride (4.11 g) and heat to 140°C while stirring. After the reaction is complete, check for precipitation with methanol, filter, and dry under vacuum. Purify the dried solid by column chromatography. Add an appropriate amount of MC to the solid obtained after purification to dissolve the solid, and then add methanol to crystallize. Filter the crystallized solid and dry under vacuum to obtain intermediate 8-2.

[0334] (3) Preparation of a compound represented by chemical formula 1-8

[0335]

[0336] In a 250 mL flask, add the intermediate 8-2 (5 g), sodium sulfite (3.67 g), THF (Tetrahydrofuran) 30 g, and DIW 30 g, and heat to 65°C while stirring. After the reaction is complete, remove THF using an evaporator, and then add 70 g of a 20 wt% NaCl aqueous solution. Separate the solid through a filter, then add MC (Dichloromethane), stir for 30 minutes, and filter again to remove unreacted dye and impurities. The solid thus obtained is vacuum-dried to obtain a compound represented by the chemical formula 1-8 (Maldi-tof MS: 1029 m / z).

[0337]

[0338] Comparative synthesis example 1

[0339] (1) Preparation of comparative intermediate 1

[0340]

[0341] In a 100 ml flask, add 4-Propylphenol (5 g), 4-Nitrophthalonitrile (6.35 g), K2CO3 (6.08 g), and N,N-dimethylformamide (DMF) (25 ml), heat to 70°C, and stir. After the reaction is complete, extract with MC (Dichloromethane). After extraction, concentrate, and purify by column chromatography. After purification, vacuum dry to obtain comparative intermediate 1.

[0342] (2) Preparation of a compound represented by chemical formula C-1

[0343]

[0344] In a 100 mL flask, add comparative intermediate 1 (3 g), phthalonitrile (4.40 g), 1,8-Diazabicycloundec-7-ene (2.08 g), and 1-pentanol (30 g), heat to 90°C until the solid dissolves, then add copper (II) chloride (1.54 g) and heat to 140°C while stirring. After the reaction is complete, check for precipitation with methanol, filter, and dry under vacuum. Purify the dried solid by column chromatography. After purification, add an appropriate amount of MC (Dichloromethane) to the solid obtained to dissolve the solid, and then add methanol to crystallize. Filter the crystallized solid and dry under vacuum to obtain a compound represented by the chemical formula C-1 (Maldi-tof MS: 710 m / z).

[0345]

[0346] Preparation of pigment dispersions

[0347] Pigment dispersions of Manufacturing Examples 1 to 10 and Manufacturing Comparative Examples 1 and 2 were prepared by mixing the compositions shown in Table 1 below (unit: g).

[0348] (Pigment refinement)

[0349] 231 g of blue pigment (CI Pigment Blue 15:6 (TOYO INK Co., Ltd., product name [Lionol Blue Es])), 69 g of purple pigment 23 (CI Pigment violet 23 (TOYO INK Co., Ltd., product name [Liongen Violet FG])), 3000 g of sodium sulfate, and 850 g of diethylene glycol (DEG) were placed in a roll mixer and mixed at 50°C for 9 hours. This mixture was poured into 8 L of warm water (70°C) and stirred for 30 minutes to make a slurry.

[0350] After filtering through a Buchner funnel, deionized water was added and washed until the electrical conductivity of the washing solution became 3 μS / cm or less. The obtained result was dried at 90°C for 16 hours and pulverized in a pulverizer to obtain 300 g of micronized pigment.

[0351] (Manufacture of pigment dispersion)

[0352] 40.0 g (100 parts) of dispersant (Hinoact T-8000E, manufactured by KAWAKEN Co., Ltd., acid value 3.8 mgKOH / g, amine value 25.3 mgKOH / g), 12.0 g (35 parts) of dispersing resin (Lipoxy SPC2000, manufactured by Showa Polymer Co., Ltd.), and 48.0 g (120 parts) of solvent (propylene glycol monomethyl ether acetate (PGMEA)) were placed in a mixer with a capacity of 500 mL and stirred for 10 minutes to perform preliminary dispersion.

[0353] To the obtained pre-dispersed product, 40.00 g (100 parts) of a pigment composed of 36.8 g of the above-mentioned micronized pigment (CIPigment Blue 15:6) and 3.2 g of the dispersing aid of Synthesis Examples 1 to 10 and Comparative Synthesis Example 1 was added, and 720 g of zirconia beads having a diameter of 0.1 mm was added thereto, and the mixture was dispersed by shaking for 3 hours using a paint shaker, and the zirconia beads were removed with a filter to prepare a blue pigment dispersion.

[0354]

[0355]

[0356]

[0357] Preparation of yellow pigment dispersion

[0358] 12.0 parts by weight of yellow pigment (CI PIGMENT Yellow 138), 3.0 parts by weight of dispersant (BYK-LPN6919, manufacturer: BYK), and 85.0 parts by weight of solvent (propylene glycol monomethyl ether acetate, PGMEA) are mixed, and 300 parts of zirconia beads (diameter: 0.4 ㎛) are added based on 100 parts by weight of this mixture, and the mixture is shaken and dispersed for 3 hours using a paint shaker, and the zirconia beads are removed by a filter, thereby obtaining a yellow pigment dispersion.

[0359]

[0360] Preparation of photosensitive resin composition

[0361] The photosensitive resin compositions of Examples 1 to 10 and Comparative Examples 1 and 2 were prepared by mixing the compositions shown in Table 2 below (unit: weight%).

[0362] Specifically, a photosensitive colored resin composition was prepared by mixing pigment dispersions (respective blue pigment dispersions and yellow pigment dispersions of Preparation Examples 1 to 10 and Preparation Comparative Examples 1 and 2), alkali-soluble resins (resin copolymerized with benzyl methacrylate and methacrylic acid at a ratio of 85:15, Mw = 22,000), photopolymerization monomers (DPHA manufactured by Nippon Kayaku Co., Ltd.), photopolymerization initiators [1,2-octanedione (C1) and 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one (C2)], and solvent [propylene glycol monomethyl ether acetate (PGMEA)].

[0363]

[0364]

[0365]

[0366] Evaluation Example 1: Dispersibility and Dispersion Stability

[0367] Using a dynamic light scattering analyzer, the particle size of the solid content included in each photosensitive resin composition of Examples 1 to 10 and Comparative Examples 1 and 2 was measured, and the results are shown in Table 3 below.

[0368] In addition, for each photosensitive resin composition of Examples 1 to 10 and Comparative Examples 1 and 2, the viscosity was evaluated at 23°C for one week before and after storage at 5 rpm (rpm selected at which the torque value is 50 to 100%) and 25°C using a Brookfield DV-II Pro viscometer and CPE-52 Spindle, and the results are shown in Table 3 below.

[0369]

[0370] Solid content particle size (nm) viscosity (cPs) Difference after 1 week after production Difference after 1 week after production Example 1 38.5 38.4-0.14.32 4.32 0.00 Example 2 41.5 41.6 0.14.27 4.28 0.01 Example 3 39.9 40.00.14.30 4.28-0.02 Example 4 40.5 40.60.14.27 4.28 0.01 Example 5 43.5 42.9-0.64.23 4.25 0.02 Example 6 37.9 38.00.14.30 4.28-0.02 Example 7 35.9 35.8-0.14.31 4.29-0.02 Example 836.836.2-0.64.324.320.00Example 933.533.60.14.274.280.01Example 1039.940.00.14.304.28-0.02Comparative Example 143.446.73.34.786.021.24Comparative Example 243.044.71.73.995.841.85

[0371] According to Table 3 above, the photosensitive resin compositions of Examples 1 to 10 show a smaller difference in viscosity as well as in solid particle size before and after storage for one week compared to the photosensitive resin compositions of Comparative Examples 1 and 2.

[0372]

[0373] Evaluation Example 2: Color strength and residue characteristics

[0374] Each of the photosensitive resin compositions of Examples 1 to 10 and Comparative Examples 1 and 2 was applied to a thickness of 1 to 3 μm on a 1 mm thick glass substrate that had been degreased and washed, and dried on a hot plate at 90°C for 2 minutes to obtain a coating film. Subsequently, the coating film was exposed 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 specimen.

[0375] The pixel layer measured the color coordinates (x, y), luminance (Y), and contrast ratio of the color filter specimen using a spectrophotometer (MCPD3000, Otsuka electronic), and the results are shown in Table 4 below.

[0376] Residue evaluation was performed by preparing a blue pattern substrate on a lower SiNx 1000Å coated glass, performing EUV cleaning using an Eximer UV asher, and then coating and developing the photosensitive resin compositions obtained in Examples 1 to 10 and Comparative Examples 1 and 2, and observing the residue on the SiNx substrate with an optical microscope. The results are shown in Table 4 below.

[0377] (Residue Characteristics Evaluation Criteria)

[0378] ○: No residue on the organic film was observed under an optical microscope.

[0379] △: Residue on the organic film is faintly visible

[0380] X: Extensive residues are visible on the organic film

[0381]

[0382] xyY Contrast Ratio Residual Characteristics Example 10.13510.120015.3315,500○Example 20.13510.120015.3215,500○Example 30.13510.120015.3215,600○Example 40.13510.120015.3415,600○Example 50.13510.120015.3215,600○Example 60.13510.120015.3515,500○Example 70.13510.120015.3315,600○Example 80.13510.120015.3415,600○Example 90.13510.120015.3515,700○Example 100.13510.120015.3415,600○Comparative Example 10.13510.120015.2815,400△Comparative Example 20.13510.120015.3015,800X

[0383] According to Table 4 above, it can be confirmed that the color filter specimens of Examples 1 to 10 have improved coloring power and residue characteristics compared to the color filter specimens of Comparative Examples 1 and 2.

[0384]

[0385] In summary, by using the dispersing aid represented by the above chemical formula 1, a photosensitive resin composition having high pigment dispersibility and dispersion stability, as well as excellent coloring power and reflection characteristics when implementing a color filter, can be realized.

[0386] Here, examples 1 to 10 are exemplified as representative examples, but it may also be possible to control dispersibility, dispersion stability, coloring power, contrast ratio, etc. to the desired level by adjusting within the scope of one embodiment.

[0387]

[0388] Although the preferred embodiments of the present invention have 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 attached drawings, and it is obvious that this also falls within the scope of the present invention.

Claims

1. (A) Colorant; (B) Photopolymerizable compound; (C) Photopolymerization initiator; (D) binder resin; and (E) containing a solvent, The above colorant is a photosensitive resin composition comprising a pigment, a dispersant, and a dispersing aid represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, M is Cu, Co or Zn; R 11 Inland R 14 , R 21 Inland R 24 , R 31 Inland R 34 and R 41 Inland R 44 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryloxy group, The above R 31 Inland R 34 and R 41 Inland R 44 At least two of which have a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group, and are a C1 to C20 alkoxy group including a sulfonate at the terminal or a C6 to C20 aryloxy group including a sulfonate at the terminal.

2. In paragraph 1, The above R 11 Inland R 14 A photosensitive resin composition in which all are hydrogen atoms or all are halogen atoms.

3. In paragraph 1, The above R 21 Inland R 24 A photosensitive resin composition wherein at least one of the groups is a substituted or unsubstituted C1 to C20 alkyl group.

4. In paragraph 1, The above R 21 Inland R 24 A photosensitive resin composition wherein at least one of the groups has a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group, and is a C1 to C20 alkoxy group including a sulfonate at the terminal or a C6 to C20 aryloxy group including a sulfonate at the terminal.

5. In paragraph 1, The above R 31 Inland R 34 At least one of the above R 41 Inland R 44 A photosensitive resin composition wherein at least one of the groups has a substituted or unsubstituted C1 to C20 alkylene group and / or ester group as a linking group, and is a C1 to C20 alkoxy group including a sulfonate at the terminal or a C6 to C20 aryloxy group including a sulfonate at the terminal.

6. In paragraph 1, The above R 31 Inland R 34 One of and the above R 41 Inland R 44 One of them is a photosensitive resin composition represented by any one of the following chemical formulas L-1 to L-4: [Chemical formula L-1] [Chemical formula L-2] [Chemical formula L-3] [Chemical formula L-4] In the above chemical formulas L-1 to L-4, L 1 is a substituted or unsubstituted C1 to C4 alkylene group, L 2 is a substituted or unsubstituted C1 to C20 alkylene group, n is an integer from 1 to 5, X is a group 1 element.

7. In paragraph 6, The above R 21 Inland R 24 One of the above R 31 Inland R 34 One of and the above R 41 Inland R 44 One of them is a photosensitive resin composition represented by any one of the chemical formulas L-1 to L-4.

8. [Revised on 02.07.2024 by Article 91 of the Rules] In paragraph 1, the dispersing aid represented by the chemical formula 1 is a photosensitive resin composition represented by any one of the following chemical formulas 1-1 to 1-8 or a combination thereof: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] 9. In paragraph 1, A photosensitive resin composition having a maximum absorption wavelength of 450 nm to 495 nm, wherein the dispersing aid represented by the above chemical formula 1 is a photosensitive resin composition.

10. In paragraph 1, A photosensitive resin composition in which the dispersing aid represented by the above chemical formula 1 is contained in an amount of 0.01 wt% to 1 wt% based on the total amount of the photosensitive resin composition.

11. In paragraph 1, A photosensitive resin composition in which the weight ratio of the dispersing aid represented by the above chemical formula 1 and the above pigment is 1:5 to 1:

20.

12. In paragraph 1, The above pigment is a photosensitive resin composition comprising a blue pigment, a green pigment, a purple pigment, a yellow pigment or a combination thereof.

13. In paragraph 1, The above photosensitive resin composition, with respect to the total amount of the photosensitive resin composition, 15 to 50 wt% of the above (A) colorant; 0.1 wt% to 10 wt% of the above (B) photopolymerizable compound; 0.1 wt% to 5 wt% of the above (C) photopolymerization initiator; 0.5 wt% to 10 wt% of the above (D) binder resin; and Containing the above (E) solvent residue Photosensitive resin composition.

14. A photosensitive resin film manufactured using the photosensitive resin composition of any one of claims 1 to 13.

15. In paragraph 14, The above photosensitive resin film is a photosensitive resin film that is a negative photoresist.

16. A color filter comprising the photosensitive resin film of Article 14.

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