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

Abstract

A photosensitive resin composition, a photosensitive resin film manufactured using the composition, and a color filter are disclosed, wherein the photosensitive resin composition comprises a compound having a specific structure.

Description

[0001] Citations of relevant applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0202847, filed on December 31, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This disclosure relates to photosensitive resin compositions, photosensitive resin films manufactured using said photosensitive resin compositions, and color filters. Background Technology

[0004] Among various types of displays, liquid crystal displays (LCDs) offer advantages such as being lightweight, thin, low-cost, low-power operation, and having improved adhesion to integrated circuits, and have been more widely used in laptops, monitors, and TV screens.

[0005] The liquid crystal display device includes 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 portion including a liquid crystal layer, a thin film transistor and a capacitor layer and an ITO pixel electrode are formed.

[0006] Each pixel is formed by stacking multiple color filters (typically formed by the three primary colors such as red (R), green (G) and blue (B)) in a predetermined order in a pixel area, and a black matrix layer is arranged on a transparent substrate in a predetermined pattern to form the boundary between pixels.

[0007] Pigment dispersion, as one method of forming color filters, provides colored films by repeating a series of processes, such as coating a photopolymerizable composition containing a colorant onto a transparent substrate including a black matrix, exposing the formed pattern to light, removing the unexposed portions with a solvent, and thermally curing it.

[0008] Coloring photosensitive resin compositions used to manufacture color filters according to the pigment dispersion method typically include alkali-soluble resins, photopolymerizable monomers, photopolymerization initiators, epoxy resins, solvents, and other additives.

[0009] Pigment dispersion methods are actively applied to the manufacture of LCDs, such as mobile phones, laptops, monitors, and TVs.

[0010] However, in recent years, photosensitive resin compositions for color filters using pigment dispersion methods with various advantages not only need excellent patterning properties but also require further improved performance. In particular, high brightness and high contrast properties, as well as high color gamut properties, are urgently needed.

[0011] Meanwhile, image sensors are the components in portable mobile phone cameras or DSCs (digital still cameras) used to capture images. Based on manufacturing processes and application methods, they can be classified into charge-coupled device (CCD) image sensors and complementary metal-oxide-semiconductor (CMOS) image sensors.

[0012] Color imaging devices for charge-coupled device image sensors or complementary metal-oxide-semiconductor image sensors include color filters, each having a filter segment that mixes red, green, and blue primary colors, and the colors are separated.

[0013] The color filters recently installed on color imaging devices have a pattern size of 2 μm or smaller, which is 1 / 100 to 1 / 200 of the pattern size of conventional color filters used in LCDs.

[0014] Therefore, improving resolution and reducing pattern residue are crucial factors in determining device performance. Consequently, in recent years, photosensitive resin compositions for color filters using pigment dispersion methods with numerous advantages have required not only excellent patterning properties but also further improved performance. In particular, compositions with high tinting strength, contrast, and residue characteristics, while simultaneously improving pigment dispersion stability, are urgently needed.

[0015] Meanwhile, color filters made using pigment-based photosensitive resin compositions are limited in brightness and contrast due to the size of the pigment particles. Furthermore, in the case of color imaging devices used in image sensors, a smaller dispersion particle size is required to form fine patterns. Therefore, an attempt has been made to achieve color filters with improved brightness and contrast by introducing dyes that do not form particles instead of pigments and by manufacturing photosensitive resin compositions suitable for the dyes.

[0016] Having clearly understood the above-mentioned needs, the inventors have invented a photosensitive resin composition that not only has excellent brightness and contrast, but also excellent reliability such as durability by introducing both dyes and pigments. Summary of the Invention

[0017] Some exemplary embodiments provide photosensitive resin compositions that not only have excellent brightness and contrast, but also excellent reliability such as durability.

[0018] Some exemplary embodiments provide photosensitive resin films made using photosensitive resin compositions.

[0019] Some exemplary embodiments provide color filters that include a photosensitive resin film.

[0020] Some exemplary embodiments provide photosensitive resin compositions comprising: (A) a colorant, (B) a photopolymerizable compound, (C) a photopolymerization initiator, (D) an adhesive resin, and (E) a solvent, wherein the colorant comprises a compound represented by chemical formula 1A or chemical formula 1B.

[0021] [Chemical Formula 1A]

[0022]

[0023] [Chemical Formula 1B]

[0024]

[0025] In chemical formula 1A and chemical formula 1B,

[0026] L 1 and L 2 Each is independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, provided that: L 1 and L 2 They are not both single keys.

[0027] R 1 To R 3 Each is independently a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0028] L 1 and R 1 They can fuse together to form fused rings, and

[0029] R 2 and R 3 They can merge together to form fused rings.

[0030] Substituted or unsubstituted C1 to C20 oxyalkylene groups can be represented by chemical formula 2.

[0031] [Chemical Formula 2]

[0032]

[0033] In chemical formula 2,

[0034] L 3 It is a substituted or unsubstituted C1 to C20 alkylene group, and

[0035] n is an integer from 1 to 10.

[0036] In chemical formula 1A or chemical formula 1B, L 1 and L 2At least one of them can be a substituted or unsubstituted C1 to C20 alkylene oxide, R 2 It can be a substituted or unsubstituted C1 to C20 alkyl group, and R 3 It can be a substituted or unsubstituted C6 to C20 aryl group.

[0037] In chemical formula 1A or chemical formula 1B, R 1 It can be represented by chemical formula 3.

[0038] [Chemical Formula 3]

[0039]

[0040] In chemical formula 3,

[0041] L 1 and L 2 Each is independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, provided that: L 1 and L 2 They are not both single keys.

[0042] Chemical formula 1A can be represented by chemical formula 4-1A or chemical formula 4-2A, and chemical formula 1B can be represented by chemical formula 4-1B or chemical formula 4-2B.

[0043] [Chemical Formula 4-1A]

[0044]

[0045] [Chemical Formula 4-2A]

[0046]

[0047] [Chemical Formula 4-1B]

[0048]

[0049] [Chemical Formula 4-2B]

[0050]

[0051] In chemical formulas 4-1A to 4-2B,

[0052] L 2 It is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof.

[0053] L 4 It is a substituted or unsubstituted C1 to C20 alkylene group, and

[0054] R 2 and R 3 Each is independently a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0055] In chemical formula 1A or chemical formula 1B, R 2 and R 3 They can merge together to form fused rings.

[0056] Compounds represented by chemical formula 1A or chemical formula 1B can be dyes.

[0057] Compounds represented by chemical formula 1A or chemical formula 1B can be represented by any one of chemical formulas 1-1 to 1-8.

[0058] [Chemical Formula 1-1]

[0059]

[0060] [Chemical Formula 1-2]

[0061]

[0062] [Chemical Formulas 1-3]

[0063]

[0064] [Chemical Formulas 1-4]

[0065]

[0066] [Chemical Formulas 1-5]

[0067]

[0068] [Chemical Formulas 1-6]

[0069]

[0070] [Chemical Formulas 1-7]

[0071]

[0072] [Chemical Formulas 1-8]

[0073]

[0074] Based on the total amount of the photosensitive resin composition, a compound represented by chemical formula 1A or chemical formula 1B may be included in an amount ranging from 1 wt% to 10 wt%.

[0075] Colorants may also contain pigments.

[0076] Pigments can include red pigments, yellow pigments, or combinations thereof.

[0077] Based on the total amount of the photosensitive resin composition, the photosensitive resin composition may contain 10 to 30 wt% of (A) a colorant, 0.1 to 10 wt% of (B) a photopolymerizable compound, 0.1 to 5 wt% of (C) a photopolymerization initiator, 0.5 to 10 wt% of (D) an adhesive resin, and the balance amount of (E) a solvent.

[0078] Some exemplary embodiments provide photosensitive resin films made using photosensitive resin compositions.

[0079] The photosensitive resin film can be a negative photoresist.

[0080] Some exemplary embodiments may be color filters that include a photosensitive resin film.

[0081] Other embodiments of the invention are included in the following detailed description.

[0082] The photosensitive resin compositions according to some exemplary embodiments can realize color filters with excellent brightness and contrast, as well as excellent reliability such as durability. Therefore, excellent display devices can be realized by using the photosensitive resin compositions according to some exemplary embodiments. In particular, compared with conventional photosensitive resin compositions containing oxalate compounds as colorants, brightness can be significantly improved without any reduction in lightfastness, chemical resistance, etc. Detailed Implementation

[0083] Embodiments of the present invention are described in detail below. However, these embodiments are exemplary, and this disclosure is not limited thereto.

[0084] As used herein, unless otherwise specifically defined, “substituted” means that at least one hydrogen atom of a compound is replaced by a substituent of: a halogen atom (F, Cl, Br or I), a hydroxyl group, a C1 to C20 alkoxy group, a glycidyl group, a nitro group, a cyano group, an amino group, an imino group, an azide group, a formamidinyl group, a hydrazine group, a hydrazine 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, 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 heterocyclic alkyl group, a C2 to C20 heterocyclic alkenyl group, a C2 to C20 heterocyclic alkynyl group, or a combination thereof.

[0085] As used herein, unless otherwise specifically defined, “heterocycloalkyl,” “heterocycloalkenyl,” “heterocycloynyl,” and “heterocycloalkylene group” refer to cyclic compounds of the cycloalkyl, cycloalkenyl, cycloynyl, and heterocycloalkylene groups that include at least one heteroatom of N, O, S, or P.

[0086] As used herein, unless otherwise specifically defined, “(meth)acrylate” refers to both “acrylate” and “methacrylate”.

[0087] As used herein, unless otherwise defined, the term “composite” means blend or copolymer. Furthermore, “copolymer” refers to block copolymer to random copolymer, and “polymer” refers to block copolymer to random copolymer.

[0088] As used in this article, when no chemical bond is drawn at the position where it is required, hydrogen bonding is at the position in the chemical formula unless otherwise defined in the chemical formula.

[0089] As used in this article, unless otherwise specifically defined, "*" represents a point connecting the same or different atoms or chemical formulas.

[0090] As used herein, unless otherwise defined, “particle size” can refer to the diameter of a particle, and particle size can be the Z-mean of the particle size as measured by dynamic light scattering.

[0091] (Photosensitive resin composition)

[0092] Some exemplary embodiments provide a photosensitive resin composition comprising: (A) a colorant, (B) a photopolymerizable compound, (C) a photopolymerization initiator, (D) an adhesive resin, and (E) a solvent, wherein the colorant comprises a compound represented by formula 1A or formula 1B:

[0093] [Chemical Formula 1A]

[0094]

[0095] [Chemical Formula 1B]

[0096]

[0097] In chemical formula 1A and chemical formula 1B,

[0098] L 1 and L 2 Each is independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, provided that: L 1 and L 2They are not both single keys.

[0099] R 1 To R 3 Each is independently a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0100] L 1 and R 1 They can fuse together to form fused rings, and

[0101] R 2 and R 3 They can merge together to form fused rings.

[0102] The compounds represented by chemical formulas 1A and 1B are xatonne compounds and have a resonance structure as shown in the following chemical formulas.

[0103] [Chemical Formula]

[0104]

[0105] (A) Coloring agent

[0106] As described above, color filters made from pigment-based photosensitive resin compositions have limitations in brightness and contrast due to the size of the pigment particles. Furthermore, for application in image sensors, it is required that resin compositions made from smaller particles form fine patterns. To achieve this, it is necessary to develop compounds that help disperse the pigments and prevent re-aggregation, and compositions using these compounds.

[0107] Therefore, the inventors of this invention have overcome the limitations of brightness and contrast, which are limitations of pigment-type photosensitive resin compositions, by including compounds represented by chemical formula 1A or chemical formula 1B (i.e., dye compounds as colorants), and further confirmed that color filters with improved reliability (including durability and chemical resistance) can be achieved by using photosensitive resin compositions containing dye compounds represented by chemical formula 1A or chemical formula 1B, thereby completing the present invention.

[0108] Xanthannae compounds are generally known to possess excellent red spectral characteristics. The inventors of this invention have modified the structure of xanthannae compounds to achieve photosensitive resin compositions for color filters exhibiting excellent brightness and contrast, durability, chemical resistance, and high reliability. In particular, these effects can be further amplified when compounds represented by Formula 1A or Formula 1B are used in conjunction with pigments.

[0109] Specifically, compounds represented by Formula 1A or Formula 1B can readily achieve the above-mentioned effects by not directly attaching hydrogen atoms to the nitrogen atom attached to the parent zeaxanthin-like compound, and by further including one or more epoxy groups as substituents at the end. The above-mentioned effects may not be easily achieved if at least one hydrogen atom is directly attached to the nitrogen atom attached to the parent zeaxanthin-like compound, or if the epoxy group is not substituted at the end.

[0110] Additionally, in chemical formula 1A or chemical formula 1B, L 1 and L 2 It may not include cyclic linking groups, such as aryl groups. In this case, it is easy to obtain effects such as improved tinting strength while minimizing the deterioration of durability.

[0111] For example, substituted or unsubstituted C1 to C20 oxyalkylene groups can be represented by chemical formula 2.

[0112] [Chemical Formula 2]

[0113]

[0114] In chemical formula 2,

[0115] L 3 It is a substituted or unsubstituted C1 to C20 alkylene group, and

[0116] n is an integer from 1 to 10.

[0117] For example, in chemical formula 1A or chemical formula 1B, L 1 and L 2 At least one of them can be a substituted or unsubstituted C1 to C20 alkylene oxide, R 2 It can be a substituted or unsubstituted C1 to C20 alkyl group, and R 3 It can be a substituted or unsubstituted C6 to C20 aryl group.

[0118] For example, R 1 It can be represented by chemical formula 3.

[0119] [Chemical Formula 3]

[0120]

[0121] In chemical formula 3,

[0122] L 1 and L 2 Each is independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, provided that: L 1 and L 2 They are not both single keys.

[0123] That is, in chemical formula 1A or chemical formula 1B, there may be two or more epoxy substituents at the end, and in this case, the linking group between the parent zeolite and the epoxy substituent at the end may be the same.

[0124] For example, in chemical formula 1A or chemical formula 1B, L 1 and R 1 They can fuse together to form fused rings, in which case chemical formula 1A can be represented by chemical formula 4-1A or chemical formula 4-2A, and chemical formula 1B can be represented by chemical formula 4-1B or chemical formula 4-2B.

[0125] [Chemical Formula 4-1A]

[0126]

[0127] [Chemical Formula 4-2A]

[0128]

[0129] [Chemical Formula 4-1B]

[0130]

[0131] [Chemical Formula 4-2B]

[0132]

[0133] In chemical formulas 4-1A to 4-2B,

[0134] L 2 It is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof.

[0135] L 4 It is a substituted or unsubstituted C1 to C20 alkylene group, and

[0136] R 2 and R 3 Each is independently a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0137] For example, in chemical formula 1A or chemical formula 1B, R 2 and R 3 They can fuse together to form fused rings, in which case chemical formula 1A can be represented by chemical formula 5-1A, and chemical formula 1B can be represented by chemical formula 5-1B.

[0138] [Chemical Formula 5-1A]

[0139]

[0140] [Chemical Formula 5-1B]

[0141]

[0142] In chemical formulas 5-1A and 5-1B,

[0143] L 1 and L 2 Each is independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, provided that: L 1 and L 2 They are not both single keys.

[0144] R 1 It is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof.

[0145] L 4 and L 5 Each is independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted C6 to C20 arylene group.

[0146] A is a nitrogen-containing monocyclic ring or a nitrogen-containing fused ring.

[0147] For example, when A is a nitrogen-containing monocyclic ring, A can be pyrrolidine, acridine, aziridine, pyrrole, pyrazole, imidazole, triazole, etc., but is not limited to these.

[0148] For example, when A is a nitrogen-containing fused ring, A can be indoline, indole, isoindole, indazole, azaindole, carbazole, purine, quinoline, etc., but is not limited to these.

[0149] For example, a compound represented by chemical formula 1A or chemical formula 1B can be a dye, such as a red dye.

[0150] For example, compounds represented by chemical formula 1A or 1B can have a maximum absorption wavelength (λ) in the range of 480 nm to 600 nm. max ).

[0151] For example, a compound represented by chemical formula 1A or chemical formula 1B can be represented by any one of chemical formulas 1-1 to 1-8.

[0152] [Chemical Formula 1-1]

[0153]

[0154] [Chemical Formula 1-2]

[0155]

[0156] [Chemical Formulas 1-3]

[0157]

[0158] [Chemical Formulas 1-4]

[0159]

[0160] [Chemical Formulas 1-5]

[0161]

[0162] [Chemical Formulas 1-6]

[0163]

[0164] [Chemical Formulas 1-7]

[0165]

[0166] [Chemical Formulas 1-8]

[0167]

[0168] For example, based on the total amount of the photosensitive resin composition, a compound represented by chemical formula 1A or chemical formula 1B may be included in an amount of 1 wt% to 10 wt% (e.g., 2 wt% to 8 wt%, e.g., 3 wt% to 7 wt%). When a compound represented by chemical formula 1A or chemical formula 1B is included in the above range, brightness and contrast can be improved more easily.

[0169] For example, the colorant may also contain pigments. That is, the photosensitive resin composition according to some exemplary embodiments may be a hybrid composition.

[0170] For example, pigments can include red pigments, yellow pigments, or combinations thereof.

[0171] The red pigment can 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. in the color index. They can be used alone or in a mixture of two or more, but the present invention is not limited thereto.

[0172] Yellow pigments can be isoindoline pigments, such as CI yellow pigment 185 and CI yellow pigment 139 in the color index; quinophthalone pigments, such as CI yellow pigment 138 in the color index; nickel complex pigments, such as CI yellow pigment 150 in the color index. They can be used alone or in mixtures of two or more, but the present invention is not limited thereto.

[0173] For example, pigments can also include purple pigments, green pigments, blue pigments, black pigments, etc.

[0174] Purple pigments can be CI Purple Pigment 23 (V.23), CI Purple Pigment 29, Dioxazine Violet, First Violet B, Methyl Violet Lake, Indanethrene Brilliant Violet, etc., as listed in the color index. They can be used alone or in mixtures of two or more, but the present invention is not limited thereto.

[0175] Green pigments can be CI green pigment 7, CI green pigment 36, CI green pigment 58, CI green pigment 59, etc. in the color index. They can be used alone or in mixtures of two or more, but the present invention is not limited thereto.

[0176] The blue pigment can 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 in the color index. They can be used alone or in mixtures of two or more, but the present invention is not limited thereto.

[0177] Black pigments can be aniline black, perylene black, titanium black, carbon black, etc., as listed in the color index. They can be used alone or in mixtures of two or more, but the present invention is not limited thereto.

[0178] Pigments can be used with dispersants in the form of pigment dispersions. For example, dispersants help to uniformly disperse pigments and can include nonionic, anionic, or cationic dispersants. Specific examples can be polyalkylene glycols or their esters, polyoxyalkylene oxides, polyol ester epoxide addition products, alcohol epoxide addition products, sulfonates, sulfonates, carboxylic esters, carboxylates, alkylamide epoxide addition products, alkylamines, and can be used alone or in mixtures of two or more.

[0179] In addition to pigments and dispersants, pigment dispersions may also contain dispersing aids, dispersing solvents, dispersing resins, etc. Based on the total amount of the pigment dispersion, the solid content of the pigment may be included in an amount of 5 wt% to 20 wt% (e.g., 8 wt% to 15 wt%).

[0180] Solvents used for pigment dispersions can be ethylene glycol acetate, ethyl celex, propylene glycol monomethyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol monomethyl ether, etc., and preferably propylene glycol monomethyl ether acetate.

[0181] The dispersion resin can be an acrylic resin containing carboxyl groups, which improves the stability of the pigment dispersion and the patterning properties of the pixels.

[0182] For example, in addition to compounds represented by chemical formula 1A or chemical formula 1B, colorants may also contain metal complex dyes as dyes.

[0183] Metal complex dyes can be compounds that have maximum absorbance in the wavelength range of 200 nm to 650 nm, and if the compound has absorbance in the above range to match the color coordinate of the dye combination, then metal complex dyes of all colors soluble in organic solvents can be used.

[0184] Specifically, the metal complex dye may be a green dye with maximum absorbance in the wavelength range of 530 nm to 680 nm, a yellow dye with maximum absorbance in the wavelength range of 200 nm to 400 nm, an orange dye with maximum absorbance in the wavelength range of 300 nm to 500 nm, a red dye with maximum absorbance in the wavelength range of 500 nm to 650 nm, or a combination thereof.

[0185] Metal complex dyes can be direct dyes, acid dyes, basic dyes, acid mordant dyes, sulfur dyes, vat dyes, insoluble azo dyes (azo dyes, ice dyes), disperse dyes, reactive dyes, oxidative dyes, oil-soluble dyes, azo dyes, anthraquinone dyes, indigoid dyes, carbocation dyes, phthalocyanine dyes, nitro dyes, quinoline dyes, cyanine dyes, polymethyst dyes, or combinations thereof.

[0186] Metal complex dyes may include at least one metal ion selected from the following: Mg, Ni, Cu, Co, Zn, Cr, Pt, Pd and Fe.

[0187] Metal complex dyes can be complexes selected from at least one of the following: CI solvent pigments, such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc.; 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, etc.; 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 mordants, such as CI Mordant Green, etc. Green pigments such as 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc.; CI green pigments, such as Pigment Green 7, 36, 58, etc.; 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 and metal ions.

[0188] Metal complex dyes can have a solubility greater than or equal to 5, specifically 5 to 10, in solvents (i.e., solvents described below) used in photosensitive resin compositions according to some exemplary embodiments. The solubility can be obtained by dissolving the dye in 100 g of solvent. If the solubility of the metal complex dye is within the above range, compatibility and tinting strength with other components constituting the photosensitive resin compositions according to some embodiments can be ensured, and dye precipitation can be prevented.

[0189] Solvents may be, for example, propylene glycol monomethyl ether acetate (PGMEA), ethyl lactate (EL), ethylene glycol acetate (EGA), cyclohexanone, 3-methoxy-1-butanol, or combinations thereof.

[0190] Because of its specific range, it can be usefully used for color filters that represent high brightness and high contrast in the desired color coordinates, such as LCDs and LEDs.

[0191] Based on the total amount of the photosensitive resin composition, the metal complex dye can be included in an amount of 0.01 wt% to 1 wt%, for example, 0.01 wt% to 0.5 wt%. If the metal complex dye is used within the above range, high brightness and contrast can be displayed in the desired color coordinates.

[0192] If dyes and pigments are used in combination, they can be mixed in weight ratios of 0.1:99.9 to 99.9:0.1, and specifically 1:9 to 9:1. Mixing within these weight ratio ranges allows for proper control of chemical resistance and maximum absorption wavelength, and enables the display of high brightness and contrast in the desired color coordinates.

[0193] Based on the total amount of the photosensitive resin composition, a colorant may be included in an amount of 10 wt% to 30 wt%, specifically 15 wt% to 25 wt%. Furthermore, based on the total solids content of the photosensitive resin composition, a colorant may be included in an amount of 5 wt% to 25 wt%, specifically 6 wt% to 20 wt%. Including a colorant within the above range improves the coloring effect and developability.

[0194] (B) Photopolymerizable compounds

[0195] Photopolymerizable compounds can be monofunctional or polyfunctional esters of (meth)acrylic acid comprising at least one olefinic unsaturated double bond.

[0196] Photopolymerizable compounds can undergo full polymerization during exposure in the patterning process due to their alkene-based unsaturated double bonds, resulting in patterns with excellent heat resistance, light resistance, and chemical resistance.

[0197] 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, etc. Pentaerythritol tetra(meth)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, tri(meth)acryloyl phosphate, phenolic epoxy (meth)acrylate, etc.

[0198] Commercially available examples of photopolymerizable compounds are shown below. Monofunctional (meth)acrylates may include Aronix. (Toagosei Chemistry Industry Co., Ltd.); KAYARAD (Nippon Kayaku Co.,Ltd.); (Osaka Organic Chemical Ind., Ltd.) etc. Examples of bifunctional (meth)acrylates may include Aronix. (Toagosei Chemistry Industry Co.,Ltd.)、KAYARAD (Nippon Kayaku Co.,Ltd.)、 V-335 (Osaka Organic Chemical Ind., Ltd.), etc. Examples of trifunctional (meth)acrylates may include Aronix. (Toagosei Chemistry Industry Co.,Ltd.)、KAYARAD (Nippon Kayaku Co., Ltd.) (Osaka YukiKayaku Kogyo Co.Ltd.), etc. These can be used alone or in mixtures of two or more.

[0199] Photopolymerizable compounds can be treated with acid anhydrides to improve their developability.

[0200] Based on the total amount of the photosensitive resin composition, a photopolymerizable compound may be included in amounts from 0.1 wt% to 10 wt%, specifically from 1 wt% to 10 wt%, for example from 3 wt% to 9 wt%. If a photopolymerizable compound is included within the above range, sufficient curing occurs during exposure in the patterning process, resulting in excellent reliability and excellent developability in alkaline developers.

[0201] (C) Photopolymerization initiator

[0202] Photopolymerization initiators can be commonly used photopolymerization initiators in photosensitive resin compositions, such as acetophenone compounds, benzophenone compounds, thioxanone compounds, benzoin compounds, oxime compounds, etc.

[0203] Examples of acetophenone compounds include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylacetophenone, p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropyl-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-but-1-one, etc.

[0204] Examples of benzophenone compounds include benzoyl benzoate, benzoyl benzoate methyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc.

[0205] Examples of thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone, etc.

[0206] Examples of benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, etc.

[0207] 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-(naphthol-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthol-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-helianyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, etc.

[0208] Examples of 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-carbazole-3-yl]ethyl ketone, O-ethoxycarbonyl-α-oxoamino-1-phenylprop-1-one, etc. Specific examples of O-acyloxime compounds include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-but-1-one, 1-(4-phenylhydrothiophenyl)-butane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylhydrothiophenyl)-octane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylhydrothiophenyl)-octane-1-one-oxime-O-acetate, and 1-(4-phenylhydrothiophenyl)-but-1-one-oxime-O-acetate.

[0209] In addition to the compounds mentioned above, photopolymerization initiators may also include carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, imidazole compounds, biimidazole compounds, fluorene compounds, etc.

[0210] Photopolymerization initiators can be used with photosensitizers that can induce chemical reactions by absorbing light and being excited, and then transferring their energy.

[0211] Examples of photosensitizers include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetra-3-mercaptopropionate, and dipentaerythritol tetra-3-mercaptopropionate.

[0212] Based on the total amount of the photosensitive resin composition, a photopolymerization initiator may be included in an amount of 0.1 wt% to 5 wt%, for example, 1 wt% to 3 wt%. If a photopolymerization initiator is included within this range, excellent reliability can be ensured during exposure in the patterning process due to sufficient curing; the pattern can exhibit excellent resolution and close-contact properties, as well as excellent heat resistance, light resistance, and chemical resistance; and transmittance reduction caused by unreacted initiator can be prevented.

[0213] (D) Adhesive resin

[0214] Adhesive resins may include acrylic binder resins.

[0215] Acrylic resin is a copolymer of a first olefinic unsaturated monomer and a second olefinic unsaturated monomer that can be copolymerized therewith, and is a resin comprising at least one acryl-based repeating unit.

[0216] The first olefinic unsaturated monomer can be an olefinic unsaturated monomer comprising at least one carboxyl group, and examples of the monomer can include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, and combinations thereof.

[0217] Based on the total amount of acrylic adhesive resin, the first olefinic unsaturated monomer may be included in an amount of 5 wt% to 50 wt%, for example 10 wt% to 40 wt%.

[0218] The second olefinic unsaturated monomer can be an aromatic vinyl compound, such as styrene, α-methylstyrene, vinyltoluene, vinylbenzene methyl ether, etc.; an unsaturated carboxylic acid ester compound, such as methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxybutyl methacrylate, benzyl methacrylate, cyclohexyl methacrylate, phenyl methacrylate, etc.; an unsaturated aminoalkyl carboxylic acid ester compound, such as 2-aminoethyl methacrylate, 2-dimethylaminoethyl methacrylate, etc.; a carboxylic acid vinyl ester compound, such as vinyl acetate, vinyl benzoate, etc.; an unsaturated glycidyl carboxylic acid ester compound, such as glycidyl methacrylate, etc.; a cyanide compound, such as methacrylonitrile, etc.; an unsaturated amide compound, such as methacrylamide, etc.; etc., and the second olefinic unsaturated monomer can be used alone or in a mixture of two or more.

[0219] Specific examples of acrylic resins may be (meth)acrylic acid / benzyl methacrylate copolymers, (meth)acrylic acid / benzyl methacrylate / styrene copolymers, (meth)acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymers, (meth)acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymers, etc., but are not limited thereto, and these may be used alone or in mixtures of two or more.

[0220] Acrylic resins can have a weight-average molecular weight ranging from 5,000 g / mol to 30,000 g / mol. If an acrylic resin has a weight-average molecular weight within this range, it can help improve durability and chemical resistance.

[0221] Adhesive resins may also include epoxy adhesive resins.

[0222] The heat resistance of the adhesive resin can be improved by further including epoxy adhesive resins. Epoxy adhesive resins can be, for example, phenolic epoxy resins, tetramethylbiphenyl epoxy resins, bisphenol A epoxy resins, bisphenol F epoxy resins, alicyclic epoxy resins, or combinations thereof, but are not limited thereto.

[0223] Furthermore, adhesive resins, including epoxy-based adhesive resins, ensure the dispersion stability of colorants such as pigments, which will be described subsequently, and help form pixels with the desired resolution during the development process.

[0224] Based on the total amount of adhesive resin, epoxy adhesive resin can be included in an amount of 1 wt% to 10 wt%, for example, 5 wt% to 10 wt%. Including epoxy adhesive resin within the above range can significantly improve film residue ratio and chemical resistance.

[0225] The epoxy equivalent weight of the epoxy resin can be from 150 g / eq to 200 g / eq. Including an epoxy resin with an epoxy equivalent weight within the above range in the adhesive resin has an advantageous effect on improving the curing degree of the formed pattern and fixing the colorant in the structure in which the pattern is formed.

[0226] The adhesive resin can be dissolved in a solvent, which will be described below, in solid form to form a photosensitive resin composition. In this case, based on the total amount of the adhesive resin solution dissolved in the solvent, the adhesive resin in solid form can be included in an amount of 0.5 wt% to 10 wt%, for example 1 wt% to 4 wt%.

[0227] Furthermore, based on the total amount of the photosensitive resin composition, a binder resin may be included in an amount of 0.5 wt% to 10 wt%, specifically 1 wt% to 5 wt%. If a binder resin is included within the above range, excellent surface smoothness can be obtained due to superior developability and improved crosslinking properties during filter manufacturing.

[0228] (E) Solvent

[0229] Solvents are materials that are compatible with colorants, adhesive resins, photopolymerizable compounds, and photopolymerization initiators but do not react with them.

[0230] Examples of solvents can include alcohols, such as methanol and ethanol; ethers, such as dichloroethyl ether, n-butyl ether, diisopentyl ether, methyl phenyl ether, tetrahydrofuran, etc.; glycol ethers, such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; selenoacetic acid, such as methyl selenoacetic acid, ethyl selenoacetic acid, diethyl selenoacetic acid, etc.; carbitol, such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, etc.; propylene glycol alkyl ether acetates, such as propylene glycol alkyl ether acetates, etc. Glycol monomethyl ether acetate, propylene glycol propyl ether acetate, etc.; aromatic hydrocarbons, such as toluene, xylene, etc.; ketones, such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl n-acetone, methyl n-butyl ketone, methyl n-pentanone, 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, ethyl lactate, etc.; oxyacetic acid alkyl esters, such as methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, etc.; alkoxyacetic acid alkyl esters, such as methyl methoxyacetate, methoxy... Ethyl ethyl acetate, methoxyethyl acetate, methyl ethoxyethyl acetate, ethyl ethoxyacetate, etc.; alkyl 3-oxypropionic acid esters, such as methyl 3-oxypropionate, ethyl 3-oxypropionate, etc.; alkyl 3-alkoxypropionic acid esters, such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc.; alkyl 2-oxypropionic acid esters, such as methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc.; alkyl 2-alkoxypropionic acid esters, such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, alkyl 2-alkoxypropionate, etc. - Ethyl ethoxypropionate, methyl 2-ethoxypropionate, etc.; 2-O-2-methylpropionates, such as methyl 2-O-2-methylpropionate, ethyl 2-O-2-methylpropionate, etc.; 2-alkoxy-2-methylalkylpropionates, such as methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc., monooxymonocarboxylic acid alkyl esters; esters, such as 2-hydroxyethylpropionate, 2-hydroxy-2-methylethylpropionate, hydroxyethyl acetate, 2-hydroxy-3-methylmethylbutyrate, etc.; ketonate esters, such as ethyl pyruvate, etc. In addition, high-boiling-point solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformaniline, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, hexanoic acid, octanoic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, phenyl celazine, etc. can also be used.

[0231] Considering compatibility and reactivity, solvents that can be used include propylene glycol monomethyl ether acetate (PGMEA), n-butyl acetate (n-BA), ethylene glycol dimethyl ether, cyclohexanone, or combinations thereof.

[0232] Based on the total amount of the photosensitive resin composition, the solvent may be included in the balance, for example, 40 wt% to 90 wt%, or 45 wt% to 70 wt%. Including the solvent within this range improves the coatability of the photosensitive resin composition and results in a film with improved flatness.

[0233] (F) Other additives

[0234] The photosensitive resin composition may also contain at least one additive selected from the following: malonic acid, 3-amino-1,2-propanediol, coupling agents including vinyl or (meth)acryloyloxy groups, leveling agents, surfactants, and free radical polymerization initiators to prevent stains or spots during coating, adjust leveling, or prevent pattern residue due to undeveloped material.

[0235] The additives can be easily adjusted according to the desired physical properties.

[0236] The coupling agent can be a silane coupling agent, and examples of silane coupling agents can include trimethoxysilylbenzoic acid, γ-methacryloyloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanate propyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-(epoxycyclohexyl)ethyltrimethoxysilane, which can be used alone or in mixtures of two or more types.

[0237] Based on 100 parts by weight of the photosensitive resin composition, a silane coupling agent may be used specifically in an amount from 0.01 parts by weight to 1 part by weight.

[0238] In addition, if necessary, the photosensitive resin composition for color filters may also contain surfactants, such as fluorinated surfactants.

[0239] Examples of fluorinated surfactants include, but are not limited to, F-482, F-484 and F-478 of DIC Co., Ltd.

[0240] Based on the total amount of the photosensitive resin composition, a surfactant may be included in an amount of 0.01 wt% to 5 wt%, for example, 0.01 wt% to 2 wt%. If it is outside the above range, it may undesirably cause problems with the generation of foreign matter after development.

[0241] In addition, within the limits of not impairing the physical properties, a certain amount of other additives such as antioxidants and stabilizers can be added to the photosensitive resin composition.

[0242] (Photosensitive resin film, color filter and display device)

[0243] According to some exemplary embodiments, a photosensitive resin film manufactured using a photosensitive resin composition according to some exemplary embodiments is provided.

[0244] Photosensitive resin films in some exemplary embodiments are broadly classified into positive photoresists and negative photoresists. In some exemplary embodiments, the photosensitive resin film can be a negative photoresist. This has the following advantages: no coloration caused by the photoresist occurs, and the photosensitivity is relatively higher than that of positive photoresists.

[0245] Some exemplary embodiments provide color filters manufactured using the above-described photosensitive resin composition.

[0246] The method for manufacturing a color filter according to some exemplary embodiments is shown below.

[0247] The above-mentioned photosensitive resin composition is coated on a glass substrate by an appropriate method such as spin coating, roller coating, spray coating, etc., to form a photosensitive resin composition layer with a thickness of 0.5 μm to 10 μm.

[0248] Subsequently, a substrate having a photosensitive resin composition layer is irradiated with light to form the pattern required for the color filter. Irradiation can be performed using UV, electron beam, or X-rays as the light source, and UV irradiation can be performed in the region of, for example, 190 nm to 450 nm, and specifically 200 nm to 400 nm. Irradiation can be further performed by using a photoresist mask. After the irradiation process in this manner, the photosensitive resin composition layer exposed to the light source is treated with a developer. Here, the unexposed areas in the photosensitive resin composition layer are dissolved and a pattern for the color filter is formed. This process can be repeated the same number of times as the desired number of colors to obtain a color filter with the desired pattern. Furthermore, if the image pattern obtained by development in the above process is cured by reheating or irradiating it with photochemical rays, crack resistance, solvent resistance, etc., can be improved.

[0249] According to some exemplary embodiments, an image sensor and display device including the color filter described above are provided.

[0250] The image sensor can be a CMOS image sensor.

[0251] The display device can be a liquid crystal display device.

[0252] The invention will be described in more detail below with reference to embodiments. However, the following embodiments are merely preferred embodiments of the invention, and the invention is not limited to these embodiments.

[0253] (synthesis example)

[0254] Synthesis Example 1: Compounds represented by chemical formula 1-1

[0255] (1) Preparation of intermediate 1-1

[0256]

[0257] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropanol were added to a 250 mL flask and stirred while cooling to 0 °C. After adding 3.61 g of diethylamine to the flask, the temperature was raised to 45 °C and stirred. After the reaction was complete, the reaction product was cooled and added to 1000 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 1-1.

[0258] (2) Preparation of intermediate 1-2

[0259]

[0260] 5.0 g of intermediate 1-1, 1.33 g of o-toluidine, 1.75 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 125 °C with stirring. After the reaction was complete, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 1-2.

[0261] (3) Preparation of the compound represented by chemical formula 1-1 (compound 1)

[0262]

[0263] 3.0 g of intermediate 1-2, 2.71 g of epichlorohydrin, 2.02 g of potassium carbonate, 1.64 g of potassium hydroxide, 0.88 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 60 °C with stirring. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the product was concentrated and purified by column chromatography. After purification and vacuum drying, compound 1 was obtained.

[0264] [Chemical Formula 1-1]

[0265]

[0266] Maldi-tof MS: 569 m / z

[0267] Synthesis Example 2: Compounds represented by chemical formulas 1-2

[0268] (1) Preparation of intermediate 2-1

[0269]

[0270] 5.0 g of intermediate 1-1, 1.51 g of 2,6-dimethylmethylamine, 1.75 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 125 °C with stirring. After the reaction was complete, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 2-1.

[0271] (2) Preparation of the compound represented by chemical formula 1-2 (compound 2)

[0272]

[0273] 3.0 g of intermediate 2-1, 2.64 g of epichlorohydrin, 1.97 g of potassium carbonate, 1.60 g of potassium hydroxide, 0.85 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 60 °C with stirring. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the product was concentrated and purified by column chromatography. After purification and vacuum drying, compound 2 was obtained.

[0274] [Chemical Formula 1-2]

[0275]

[0276] Maldi-tof MS: 583 m / z

[0277] Synthesis Example 3: Compounds represented by chemical formulas 1-3

[0278] (1) Preparation of intermediate 3-1

[0279]

[0280] 5.0 g of intermediate 1-1, 1.51 g of 2,4-dimethylmethylamine, 1.75 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 125 °C with stirring. After the reaction was complete, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 3-1.

[0281] (2) Preparation of the compound represented by chemical formula 1-3 (compound 3)

[0282]

[0283] 3.0 g of intermediate 3-1, 2.64 g of epichlorohydrin, 1.97 g of potassium carbonate, 1.60 g of potassium hydroxide, 0.85 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 60 °C with stirring. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the product was concentrated and purified by column chromatography. After purification and vacuum drying, compound 3 was obtained.

[0284] [Chemical Formulas 1-3]

[0285]

[0286] Maldi-tof MS: 583 m / z

[0287] Synthesis Example 4: Compounds represented by chemical formulas 1-4

[0288] (1) Preparation of intermediate 4-1

[0289]

[0290] 5.0 g of intermediate 1-1, 1.68 g of 2,4,6-trimethylaniline, 1.75 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 125 °C with stirring. After the reaction was complete, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 4-1.

[0291] (2) Preparation of compounds represented by chemical formulas 1-4 (compound 4)

[0292]

[0293] 3.0 g of intermediate 4-1, 2.57 g of epichlorohydrin, 1.92 g of potassium carbonate, 1.56 g of potassium hydroxide, 0.83 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 60 °C with stirring. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the product was concentrated and purified by column chromatography. After purification and vacuum drying, compound 4 was obtained.

[0294] [Chemical Formulas 1-4]

[0295]

[0296] Maldi-tof MS: 597 m / z

[0297] Synthesis Example 5: Compounds represented by chemical formulas 1-5

[0298] (1) Preparation of intermediate 5-1

[0299]

[0300] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropanol were added to a 250 mL flask and stirred while cooling to 0 °C. After adding 4.40 g of 2-(ethylamino)ethanol to the flask, the temperature was raised to 45 °C and stirred. After the reaction was complete, the reaction product was cooled and added to 1000 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 5-1.

[0301] (2) Preparation of intermediate 5-2

[0302]

[0303] 5.0 g of intermediate 5-1, 1.46 g of N-ethylaniline, 1.69 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 125 °C with stirring. After the reaction was complete, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 5-2.

[0304] (3) Preparation of compounds represented by chemical formulas 1-5 (compound 5)

[0305]

[0306] 3.0 g of intermediate 5-2, 2.56 g of epichlorohydrin, 1.91 g of potassium carbonate, 1.55 g of potassium hydroxide, 0.83 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 60 °C with stirring. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the product was concentrated and purified by column chromatography. After purification and vacuum drying, compound 5 was obtained.

[0307] [Chemical Formulas 1-5]

[0308]

[0309] Maldi-tof MS: 599 m / z

[0310] Synthesis Example 6: Compounds represented by chemical formulas 1-6

[0311] (1) Preparation of intermediate 6-1

[0312]

[0313] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropanol were added to a 250 mL flask and stirred while cooling to 0 °C. After adding 5.19 g of diethanolamine to the flask, the temperature was raised to 45 °C and stirred. After the reaction was complete, the reaction product was cooled and added to 1000 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 6-1.

[0314] (2) Preparation of intermediate 6-2

[0315]

[0316] 5.0 g of intermediate 6-1, 1.41 g of N-ethylaniline, 1.64 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 125 °C with stirring. After the reaction was complete, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 6-2.

[0317] (3) Preparation of compounds represented by chemical formulas 1-6 (compound 6)

[0318]

[0319] 3.0 g of intermediate 6-2, 4.97 g of epichlorohydrin, 3.71 g of potassium carbonate, 3.01 g of potassium hydroxide, 1.61 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 60 °C with stirring. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the product was concentrated and purified by column chromatography. After purification and vacuum drying, compound 6 was obtained.

[0320] [Chemical Formulas 1-6]

[0321]

[0322] Maldi-tof MS: 615 m / z

[0323] Synthesis Example 7: Compounds represented by chemical formulas 1-7

[0324] (1) Preparation of intermediate 7-1

[0325]

[0326] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropanol were added to a 250 mL flask and stirred while cooling to 0 °C. After adding 4.30 g of 3-pyrrolidone to the flask, the temperature was raised to 45 °C and stirred. After the reaction was complete, the reaction product was cooled and added to 1000 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 7-1.

[0327] (2) Preparation of intermediate 7-2

[0328]

[0329] 5.0 g of intermediate 7-1, 1.46 g of N-ethylaniline, 1.70 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 125 °C with stirring. After the reaction was complete, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 7-2.

[0330] (3) Preparation of compounds represented by chemical formulas 1-7 (compound 7)

[0331]

[0332] 3.0 g of intermediate 7-2, 2.57 g of epichlorohydrin, 1.92 g of potassium carbonate, 1.56 g of potassium hydroxide, 0.83 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 60 °C with stirring. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the product was concentrated and purified by column chromatography. After purification and vacuum drying, compound 7 was obtained.

[0333] [Chemical Formulas 1-7]

[0334]

[0335] Maldi-tof MS: 597 m / z

[0336] Synthesis Example 8: Compounds represented by chemical formulas 1-8

[0337] (1) Preparation of intermediate 8-1

[0338]

[0339] 5.0 g of intermediate 5-1, 1.43 g of indoline, 1.69 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 125 °C with stirring. After the reaction was complete, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 8-1.

[0340] (2) Preparation of compounds represented by chemical formulas 1-8 (compound 8)

[0341]

[0342] 3.0 g of intermediate 8-1, 2.57 g of epichlorohydrin, 1.92 g of potassium carbonate, 1.56 g of potassium hydroxide, 0.83 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 60 °C with stirring. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the product was concentrated and purified by column chromatography. After purification and vacuum drying, compound 8 was obtained.

[0343] [Chemical Formulas 1-8]

[0344]

[0345] Maldi-tof MS: 597 m / z

[0346] Comparative Synthesis Example 1

[0347] (1) Preparation of Comparative Intermediate 1

[0348]

[0349] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropanol were added to a 250 mL flask and stirred while cooling to 0 °C. After adding 6.08 g of 4-amino-m-cresol to the flask, the temperature was raised to 45 °C and stirred. After the reaction was complete, the reaction product was cooled and added to 1000 mL of diethyl ether to produce a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain comparative intermediate 1.

[0350] (2) Preparation of Comparative Intermediate 2

[0351]

[0352] 5.0 g of comparative intermediate 1, 2.23 g of diethylamine, 3.94 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 60 °C with stirring. After 1 hour, the result was heated to 125 °C with stirring. After the reaction was complete, the product was cooled and added to 500 mL of diethyl ether to produce a precipitate. The precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain comparative intermediate 2.

[0353] (3) Preparation of compounds represented by chemical formula C-1 (comparative compound 1)

[0354]

[0355] 3.0 g of comparative intermediate 2, 2.63 g of epichlorohydrin, 1.59 g of potassium hydroxide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 50 °C while stirring. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the product was concentrated and purified by column chromatography. After purification and vacuum drying, comparative compound 1 was obtained.

[0356] [Chemical formula C-1]

[0357]

[0358] Maldi-tof MS: 585 m / z

[0359] Comparative Synthesis Example 2

[0360] Preparation of compounds represented by chemical formula C-2 (comparative compound 2)

[0361]

[0362] 5.0 g of intermediate 1-1, 1.86 g of N-ethyl-2,6-dimethylmethylamine, 1.75 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 125 °C with stirring. After the reaction was complete, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. After redissolving in dichloromethane, it was concentrated and purified by column chromatography. After purification and vacuum drying, the compound represented by chemical formula C-2 (comparative compound 2) was prepared.

[0363] [Chemical formula C-2]

[0364]

[0365] Maldi-tof MS: 555 m / z

[0366] Comparative Synthesis Example 3

[0367] (1) Preparation of comparative intermediate 3-1

[0368]

[0369] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropanol were added to a 250 mL flask and stirred while cooling to 0 °C. After adding 6.77 g of 4-(ethylamino)phenol to the flask, the temperature was raised to 45 °C and stirred. After the reaction was complete, the reaction product was cooled and added to 1000 mL of diethyl ether to produce a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain comparative intermediate 3-1.

[0370] (2) Preparation of comparative intermediate 3-2

[0371]

[0372] 5.0 g of comparative intermediate 3-1, 1.32 g of N-ethylaniline, 1.53 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 60 °C with stirring. After 1 hour, the result was heated to 125 °C with stirring. After the reaction was complete, the reaction product was cooled and added to 500 mL of diethyl ether to produce a precipitate. The resulting precipitate was filtered and further washed with diethyl ether. The filtrate was dried to obtain comparative intermediate 3-2.

[0373] (3) Preparation of compounds represented by chemical formula C-3 (comparative compound 3)

[0374]

[0375] 3.0 g of comparative intermediate 3-2, 2.35 g of epichlorohydrin, 1.59 g of potassium hydroxide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 mL flask and heated to 50 °C with stirring. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the product was concentrated and purified by column chromatography. After purification and vacuum drying, the compound represented by chemical formula C-3 (comparative compound 3) was prepared.

[0376] [Chemical formula C-3]

[0377]

[0378] Maldi-tof MS: 647 m / z

[0379] Preparation of yellow pigment dispersion

[0380] A yellow pigment dispersion was obtained by mixing 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), and then adding 300 parts by weight of zirconia beads (diameter: 0.4 μm) to 100 parts by weight of the mixture. The dispersion was dispersed by shaking with a paint shaker for 3 hours, and the zirconia beads were removed by filtration.

[0381] Preparation of photosensitive resin compositions

[0382] Example 1

[0383] The photosensitive resin composition of Example 1 was prepared by mixing to have the composition shown in Table 1.

[0384] Specifically, a photopolymerization initiator is dissolved in a solvent and stirred at room temperature for 2 hours. An acrylic binder resin and a photopolymerizable compound are then added to the mixture, and the mixture is stirred at room temperature for another 2 hours. Subsequently, a compound (dye) represented by chemical formula 1-1 and a pigment (in pigment dispersion form) are added as colorants to the reactants, and the mixture is stirred at room temperature for 1 hour. The resulting product is then filtered three times to remove impurities to prepare a photosensitive resin composition.

[0385] (Table 1)

[0386] (Unit: wt%)

[0387]

[0388] Example 2

[0389] The photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 2 (chemical formula 1-2) was used instead of compound 1 (chemical formula 1-1).

[0390] Example 3

[0391] The photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 3 (chemical formula 1-3) was used instead of compound 1 (chemical formula 1-1).

[0392] Example 4

[0393] The photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 4 (chemical formula 1-4) was used instead of compound 1 (chemical formula 1-1).

[0394] Example 5

[0395] The photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 5 (chemical formula 1-5) was used instead of compound 1 (chemical formula 1-1).

[0396] Example 6

[0397] The photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 6 (chemical formula 1-6) was used instead of compound 1 (chemical formula 1-1).

[0398] Example 7

[0399] The photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 7 (chemical formula 1-7) was used instead of compound 1 (chemical formula 1-1).

[0400] Example 8

[0401] The photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 8 (chemical formula 1-8) was used instead of compound 1 (chemical formula 1-1).

[0402] Comparative Example 1

[0403] The photosensitive resin composition was prepared in the same manner as in Example 1, except that comparative compound 1 (chemical formula C-1) was used instead of compound 1 (chemical formula 1-1).

[0404] Comparative Example 2

[0405] The photosensitive resin composition was prepared in the same manner as in Example 1, except that comparative compound 2 (chemical formula C-2) was used instead of compound 1 (chemical formula 1-1).

[0406] Comparative Example 3

[0407] The photosensitive resin composition was prepared in the same manner as in Example 1, except that comparative compound 3 (chemical formula C-3) was used instead of compound 1 (chemical formula 1-1).

[0408] Evaluation Example 1: Reliability

[0409] Color filter samples were prepared according to the photosensitive resin compositions of Examples 1 to 8 and Comparative Examples 1 to 3, respectively.

[0410] Specifically, each photosensitive resin composition is applied to a 1 mm thick degreased and cleaned glass substrate, and then dried on a heated plate at 90°C for 2 minutes to obtain a film.

[0411] The durability of each color filter sample was evaluated in two aspects: chemical resistance and light resistance.

[0412] Chemical resistance: at the maximum absorption wavelength (λ) max The absorbance intensity of each color filter sample was measured. Specifically, the maximum absorption wavelength (λ) of each color filter sample was determined using a UV-Vis-NIR spectrometer (UV-3600Plus, Shimadzu Scientific Instruments). max ), and simultaneously measure the absorbance intensity at that wavelength.

[0413] In addition, each filter sample was immersed in NMP (N-methyl-2-pyrrolidone) solution at 50°C for 10 minutes, rinsed with ultrapure water for 30 seconds, and dried by blowing compressed air. Subsequently, in the same manner as described above, the sample was analyzed at the maximum absorption wavelength (λ). max )Measure absorbance intensity.

[0414] The absorbance intensity of each filter sample before and after exposure to the solvent was substituted into Equation 1 to quantify chemical resistance, and the results are shown in Table 2.

[0415] [Equation 1]

[0416] Chemical resistance = {1 - (absorbance intensity after NMP immersion) / (absorbance intensity before NMP immersion)} × 100%

[0417] Lightfastness: at the maximum absorption wavelength (λ) max The absorbance intensity of each color filter sample was measured. Specifically, the maximum absorption wavelength (λ) of each color filter sample was determined using a UV-Vis-NIR spectrometer (UV-3600Plus, Shimadzu Scientific Instruments). max ), and simultaneously measure the absorbance intensity at that wavelength.

[0418] In addition, each color filter sample was exposed to 50 mJ / cm in an exposure device. 2 Expose to light, and in the same manner as described above, at the wavelength of maximum absorption (λ). max The absorbance intensity was measured under the following conditions.

[0419] The absorbance intensity of each color filter sample before and after exposure was substituted into Equation 2 to quantify the lightfastness, and the results are shown in Table 2.

[0420] [Equation 2]

[0421] Lightfastness = {1 - (Absorbance intensity after exposure) / (Absorbance intensity before exposure)} × 100%

[0422] (Table 2)

[0423]

[0424] Referring to Table 2, it is confirmed that the photosensitive resin compositions of Examples 1 to 8, which include compounds as dyes according to some exemplary embodiments, have excellent chemical resistance and lightfastness compared to those of Comparative Examples 1 to 3.

[0425] Evaluation Example 2: Brightness

[0426] In the same manner as Evaluation 1, the photosensitive resin compositions of Examples 1 to 8 and Comparative Examples 1 to 3 were respectively prepared into color filter samples.

[0427] Specifically, each photosensitive resin composition is coated to a thickness of 1 μm to 3 μm on a degreased and cleaned 1 mm thick glass substrate, and then dried on a heating plate at 90 °C for 2 minutes to obtain a film.

[0428] The obtained film was exposed using a high-pressure mercury lamp with a main wavelength of 365 nm, and then dried in a forced convection dryer at 200 °C for 5 minutes. The brightness of the pixel layer was measured using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.), and the results are shown in Table 3.

[0429] (Table 3)

[0430] brightness Example 1 68.2 Example 2 68.5 Example 3 68.4 Example 4 68.4 Example 5 68.3 Example 6 68.3 Example 7 68.2 Example 8 68.5 Comparative Example 1 67.1 Comparative Example 2 61.8 Comparative Example 3 67.7

[0431] Referring to Table 3, it is confirmed that the photosensitive resin compositions of Examples 1 to 8, which include compounds as dyes according to some exemplary embodiments, exhibit superior brightness compared to those of Comparative Examples 1 to 3.

[0432] In summary, when a compound represented by any one of the above chemical formulas 1-1 to 1-8 is included as a dye, a photosensitive resin composition that simultaneously possesses excellent lightfastness, chemical resistance, and brightness is achieved.

[0433] In this document, Examples 1 to 8 are illustrated as representative embodiments. However, within the scope of some exemplary embodiments, Examples 1 to 8 may be modified to control lightfastness, chemical resistance, brightness, etc., to the desired level.

[0434] Although the invention has been described in conjunction with exemplary embodiments which are now considered to be practical, it should be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A photosensitive resin composition comprising... (A) Coloring agent; (B) Photopolymerizable compounds; (C) Photopolymerization initiator; (D) Adhesive resin; and (E) Solvent, in, The colorant comprises a compound represented by chemical formula 1A or chemical formula 1B: [Chemical Formula 1A] [Chemical Formula 1B] In chemical formula 1A and chemical formula 1B, L 1 and L 2 each independently is a single bond, substituted or unsubstituted C1to C20alkylene, substituted or unsubstituted C1to C20oxyalkylene, or a combination thereof, provided that L 1 and L 2 are not both a single bond, R 1 To R 3 Each is independently a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C6 to C20 aryl, or a combination thereof. L 1 and R 1 They can fuse together to form fused rings, and R 2 and R 3 They can merge together to form fused rings.

2. The photosensitive resin composition according to claim 1, wherein... The substituted or unsubstituted C1 to C20 oxyalkylene groups are represented by chemical formula 2: [Chemical Formula 2] In chemical formula 2, L 3 It is a substituted or unsubstituted C1 to C20 alkylene group, and n is an integer from 1 to 10.

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

4. The photosensitive resin composition according to claim 1, wherein... The compound represented by chemical formula 1A or chemical formula 1B is represented by any one of chemical formulas 1-1 to 1-8: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] [Chemical Formulas 1-6] [Chemical Formulas 1-7] [Chemical Formulas 1-8] 5. The photosensitive resin composition according to claim 1, wherein the compound represented by chemical formula 1A or chemical formula 1B is contained in an amount of 1 wt% to 10 wt% based on the total amount of the photosensitive resin composition.

6. The photosensitive resin composition according to claim 1, wherein... The colorant also includes pigments.

7. The photosensitive resin composition according to claim 6, wherein... The pigments include red pigments, yellow pigments, or combinations thereof.

8. The photosensitive resin composition according to claim 1, wherein... Based on the total amount of the photosensitive resin composition, the photosensitive resin composition comprises: 10 wt% to 30 wt% of the colorant (A); 0.1 wt% to 10 wt% of the (B) photopolymerizable compound; 0.1 wt% to 5 wt% of the (C) photopolymerization initiator; 0.5 wt% to 10 wt% of the (D) adhesive resin; and The remainder of the solvent (E).

9. A photosensitive resin film, said photosensitive resin film being manufactured using the photosensitive resin composition according to any one of claims 1 to 8.

10. The photosensitive resin film according to claim 9, wherein... The photosensitive resin film is a negative photoresist.

11. A color filter comprising the photosensitive resin film of claim 9 or 10.

Images