Photosensitive resin composition, cured layer using same, color filter, and CMOS image sensor
The photosensitive resin composition with a yellow pigment dispersion and acidic compound enhances dispersion stability, addressing brightness and contrast issues in color filters, enabling ultra-thin, ultra-fine patterning for CMOS image sensors.
Patent Information
- Application Number
- PCT/KR2025/003078
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-04-26
- Filing Date
- 2025-03-10
- Publication Date
- 2025-10-30
AI Technical Summary
Existing pigment-type photosensitive resin compositions for color filters in liquid crystal displays and CMOS image sensors face limitations in brightness, contrast ratio, and particle size, which hinder ultra-thin, ultra-fine patterning and fine pattern formation.
A photosensitive resin composition incorporating a yellow pigment dispersion with a compound represented by a specific chemical formula, featuring acidic groups for improved dispersion stability, combined with a yellow pigment synergist and other components, to minimize particle size and enhance dispersibility.
Enables ultra-thin, ultra-fine patterning with improved brightness and contrast ratio, suitable for CMOS image sensors, by stabilizing pigment dispersions and preventing re-agglomeration.
Smart Images

Figure KR2025003078_30102025_PF_FP_ABST
Abstract
Description
Photosensitive resin composition, cured film, color filter and CMOS image sensor using the same
[0001] The present invention relates to a photosensitive resin composition, a cured film using the same, a color filter including the cured film, and a CMOS image sensor including the color filter.
[0002]
[0003] Liquid crystal display devices, which are one type of display devices, have advantages such as being lightweight, thin, low-cost, low-power driveability, and excellent compatibility with integrated circuits, and their range of use is expanding for laptop computers, monitors, and TV images. Such liquid crystal display devices are 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, and a capacitor layer, and an upper substrate on which the ITO pixel electrode is formed. The color filter has a structure in which a black matrix layer is formed in a set pattern on a transparent substrate to block light at the boundary between pixels, and a pixel portion in which a plurality of colors, typically the three primary colors of red (R), green (G), and blue (B), are arranged in a set order to form each pixel, are sequentially stacked.
[0004] 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 coating a photopolymerizable composition containing a coloring agent on a transparent substrate provided with a black matrix, exposing a pattern of a desired shape, removing the unexposed area with a solvent, and repeating a series of processes such as thermal curing. The colored photosensitive resin composition used in the manufacture of a color filter according to the pigment dispersion method is generally composed of an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives. The pigment dispersion method is actively applied in the manufacture of LCDs for mobile phones, laptops, monitors, TVs, etc.
[0005] Image sensors are image capturing components that generate images in mobile phone cameras and digital still cameras (DSCs). Depending on their manufacturing process and application, they can be broadly classified into solid-state image sensors (charge-coupled device (CCD)) and complementary metal oxide semiconductor (CMOS) image sensors. Color image capturing devices used in solid-state image sensors or complementary metal oxide semiconductors typically install color filters with filter segments of red, green, and blue additive primary colors on the light-receiving element to perform color separation. Recently, the pattern size of the color filters mounted on these color image capturing devices is 2㎛ or less, which is 1 / 100 to 1 / 200 times the size of the color filter pattern for existing LCDs. Accordingly, increasing the resolution and reducing residue are important factors that determine the performance of the device.
[0006] Meanwhile, color filters manufactured using pigment-type photosensitive resin compositions suffer from limitations in brightness and contrast ratio due to the size of the pigment particles. Furthermore, color imaging elements for image sensors require a smaller particle size to form fine patterns. To address these needs, attempts have been made to introduce non-particle dyes instead of pigments, creating photosensitive resin compositions suitable for the dyes, thereby achieving color filters with improved brightness and contrast ratio. However, dyes, compared to pigments, have lower durability in light and heat resistance, raising concerns about reduced brightness.
[0007]
[0008] One embodiment is to provide a photosensitive resin composition capable of implementing ultra-thin, ultra-fine patterning.
[0009] Another embodiment is to provide a cured film using the photosensitive resin composition.
[0010] Another embodiment is to provide a color filter comprising the above cured film.
[0011] Another embodiment is to provide a CMOS image sensor including the color filter.
[0012]
[0013] One embodiment provides a photosensitive resin composition comprising a yellow pigment dispersion comprising a compound represented by the following chemical formula 1 (or a salt thereof) and a yellow pigment; a pigment; a photopolymerizable compound; a photopolymerization initiator; and a solvent.
[0014] [Chemical Formula 1]
[0015]
[0016] In the above chemical formula 1,
[0017] X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group),
[0018] L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group or a combination thereof,
[0019] L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group,
[0020] R 1 Inland R 4are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or an acid group, provided that R 1 Inland R 4 At least one of them is acidic.
[0021] The acid group above is *-SO3 - , which may be a carboxyl group, a phosphoric acid group, or a phosphonic acid group.
[0022] Above *-N(R a )-* can be represented by the following chemical formula N.
[0023] [Chemical formula N]
[0024]
[0025] In the above chemical formula N,
[0026] L 5 is a substituted or unsubstituted C1 to C10 alkylene group,
[0027] R 5 is an acidic group.
[0028] The above chemical formula 1 can be represented by the following chemical formula 1A or chemical formula 1B.
[0029] [Chemical Formula 1A]
[0030]
[0031] [Chemical Formula 1B]
[0032]
[0033] In the above chemical formulas 1A and 1B,
[0034] X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group),
[0035] L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a)-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group or a combination thereof,
[0036] L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group,
[0037] R 1 Inland R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or an acidic group.
[0038] The above R 1 Inland R 4 At least two of them can be acidic.
[0039] The above R 1 Inland R 4 At least three of them can be acidic.
[0040] The above acid groups may be of the same type.
[0041] The above acid groups may be of different types.
[0042] The above compound (or salt thereof) may be represented by any one of the following chemical formulas 1-1 to 1-11.
[0043] [Chemical Formula 1-1]
[0044]
[0045] [Chemical Formula 1-2]
[0046]
[0047] [Chemical Formula 1-3]
[0048]
[0049] [Chemical Formula 1-4]
[0050]
[0051] [Chemical Formula 1-5]
[0052]
[0053] [Chemical Formula 1-6]
[0054]
[0055] [Chemical Formula 1-7]
[0056]
[0057] [Chemical Formula 1-8]
[0058]
[0059] [Chemical Formula 1-9]
[0060]
[0061] [Chemical Formula 1-10]
[0062]
[0063] [Chemical Formula 1-11]
[0064]
[0065] The above pigment is a red pigment dispersion containing a red pigment, and the photosensitive resin composition may further contain a binder resin.
[0066] The photosensitive resin composition may include 10 to 30 wt% of the yellow pigment dispersion; 20 to 50 wt% of the red pigment dispersion; 1 to 10 wt% of the binder resin; 0.1 to 5 wt% of the photopolymerizable compound; 0.01 to 3 wt% of the photopolymerization initiator; and the remainder of the solvent, based on the total amount of the photosensitive resin composition.
[0067] The above pigment may be a green pigment dispersion containing a green pigment.
[0068] The photosensitive resin composition may include 20 to 40 wt% of the yellow pigment dispersion; 25 to 55 wt% of the green pigment dispersion; 1 to 10 wt% of the photopolymerizable compound; 0.1 to 5 wt% of the photopolymerization initiator; and the remainder of the solvent, based on the total amount of the photosensitive resin composition.
[0069] Another embodiment provides a cured film manufactured using the photosensitive resin composition.
[0070] Another embodiment provides a color filter including the cured film.
[0071] Another embodiment provides a CMOS image sensor including the color filter.
[0072] Specific details of other embodiments of the present invention are included in the detailed description below.
[0073]
[0074] A photosensitive resin composition according to one embodiment includes a yellow pigment dispersion containing a yellow pigment synergist represented by a specific structure, thereby ultimately enabling the implementation of a color resist and a CMOS image sensor capable of ultra-thin, ultra-fine patterning.
[0075]
[0076] 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.
[0077] 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.
[0078] 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.
[0079] Unless otherwise specified herein, “(meth)acrylate” means both “acrylate” and “methacrylate”.
[0080] Unless otherwise specified herein, “combination” means mixing or copolymerization.
[0081] 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.
[0082] Additionally, unless otherwise specified herein, “*” means a portion connected to the same or different atoms or chemical formulas.
[0083]
[0084] A photosensitive resin composition according to one embodiment comprises a yellow pigment dispersion comprising a compound represented by the following chemical formula 1 and a yellow pigment; a pigment; a photopolymerizable compound; a photopolymerization initiator; and a solvent.
[0085] [Chemical Formula 1]
[0086]
[0087] In the above chemical formula 1,
[0088] X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group),
[0089] L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group or a combination thereof,
[0090] L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group,
[0091] R 1 Inland R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or an acid group, provided that R 1 Inland R 4 At least one of them is acidic.
[0092] To facilitate the stable dispersion and miniaturization of pigment dispersions, various studies are being conducted to create pigments with particles of a certain size through processes such as salt milling using synthetically obtained pigments. However, as mentioned above, color filters manufactured with pigment-type photosensitive resin compositions have limitations in brightness and contrast ratio due to the size of the pigment particles. Furthermore, color imaging elements for image sensors require a smaller particle size to form fine patterns. To meet these needs, there is a growing need for compounds necessary for finely dispersing pigment particles and creating dispersions containing pigments that do not reaggregate, and for manufacturing photosensitive resin compositions for color filters using dispersions containing such compounds.
[0093] Color filters manufactured from pigment-type photosensitive resin compositions have limitations in their tinting power due to the size of the pigment particles. Furthermore, for applications in image sensors, resin compositions comprising smaller particles are required for fine pattern formation. Furthermore, for applications in KrF exposure, further improvement in the tinting properties of existing materials is necessary. Under these circumstances, the inventors have conducted extensive research and have developed a yellow pigment derivative, i.e., a novel yellow pigment synergist (dispersing agent), and have used a yellow pigment dispersion prepared by mixing the synergist with a yellow pigment. This has ultimately enabled the provision of a composition capable of implementing ultra-thin, ultra-fine patterning.
[0094] Specifically, the compound represented by the above chemical formula 1 has one or more acidic groups at the terminal, and the acidic groups are highly polar groups, L a , L 1 Inland L 4The aforementioned effect can be more effectively realized by introducing the compound represented by the above chemical formula 1 at various positions while being connected to various types of linkers represented by . That is, the dispersion agent represented by the above chemical formula 1, in which the high polarity acidic group is introduced, is used together with a pigment, specifically a yellow pigment, and a dispersant to prevent re-agglomeration of the yellow pigment, thereby minimizing the particle size of the yellow pigment, thereby maximizing dispersion stability.
[0095] For example, the acidic group is *-SO3 - , which may be a carboxyl group, a phosphoric acid group, or a phosphonic acid group.
[0096] For example, the above *-N(R a )-* can be represented by the following chemical formula N.
[0097] [Chemical formula N]
[0098]
[0099] In the above chemical formula N,
[0100] L 5 is a substituted or unsubstituted C1 to C10 alkylene group,
[0101] R 5 is an acidic group.
[0102] Above *-N(R a )-* is represented by the following chemical formula N, the number of sites where the acid group can be introduced in the compound according to one embodiment increases, so that even in a state where the organic pigment described below is finely dispersed, good fluidity and dispersion stability can be maintained, and it can be easier to provide a pigment dispersion agent that is advantageous for implementing ultra-thin, ultra-fine patterning.
[0103] For example, the above chemical formula 1 can be represented by the following chemical formula 1A or chemical formula 1B.
[0104] [Chemical Formula 1A]
[0105]
[0106] [Chemical Formula 1B]
[0107]
[0108] In the above chemical formulas 1A and 1B,
[0109] X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group),
[0110] L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group or a combination thereof,
[0111] L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group,
[0112] R 1 Inland R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or an acidic group.
[0113] In the above chemical formula 1, *-XL 1 -R 1 By specifying the position of the substituent represented by as in the chemical formula 1A or 1B, the fluidity and dispersion stability of the organic pigment, particularly the yellow organic pigment, can be greatly improved.
[0114] For example, the above R 1 Inland R 4 At least one of them may be acidic.
[0115] For example, the above R 1 Inland R 4 At least two of them can be acidic.
[0116] For example, the above R 1 Inland R 4 At least three of them can be acidic.
[0117] For example, the above R 1 Inland R 4 All of them can be acidic.
[0118] For example, the above R 1 Inland R 4 At least two or three acid groups, or the R 1 Inland R 4 When all are acid groups, the acid groups may be the same or different. In most pigment preparations, it is difficult to combine derivatives with different structures, but the compound according to one embodiment has a structure represented by the chemical formula 1, so it is easy to combine acid groups with different structures, and it has the advantage that the introduction positions of the acid groups can be controlled in various ways.
[0119] For example, the compound may be represented by any one of the following chemical formulas 1-1 to 1-11, but is not necessarily limited thereto.
[0120] [Chemical Formula 1-1]
[0121]
[0122] [Chemical Formula 1-2]
[0123]
[0124] [Chemical Formula 1-3]
[0125]
[0126] [Chemical Formula 1-4]
[0127]
[0128] [Chemical Formula 1-5]
[0129]
[0130] [Chemical Formula 1-6]
[0131]
[0132] [Chemical Formula 1-7]
[0133]
[0134] [Chemical Formula 1-8]
[0135]
[0136] [Chemical Formula 1-9]
[0137]
[0138] [Chemical Formula 1-10]
[0139]
[0140] [Chemical Formula 1-11]
[0141]
[0142] For example, the compound may be a pigment synergist, i.e. a pigment dispersing agent.
[0143] For example, the compound may be a yellow pigment synergist, i.e. a yellow pigment dispersing agent.
[0144] For example, the yellow pigment dispersion comprises the yellow pigment synergist and a yellow pigment. The yellow pigment synergist may be present in an amount of 0.5 to 5 wt% based on the total weight of the pigment dispersion. In this case, reaggregation of the pigment can be minimized, thereby maximizing dispersion stability.
[0145] For example, examples of the yellow pigment include, but are not limited to, Pigment Yellow 138, 139, 150, 185, etc.
[0146] The above yellow pigment may be included in an amount of 5 to 20 wt% based on the total amount of the yellow pigment dispersion. In this case, the interaction between the yellow pigment synergist and the yellow pigment is maximized, thereby minimizing reaggregation of the pigment and maximizing dispersion stability.
[0147] For example, the yellow pigment dispersion may further include a dispersant, a dispersing resin, and a solvent.
[0148] For example, as the dispersant, a polymer pigment dispersant that has been conventionally used in printing ink, paint, pigment dispersion resist composition for color filters, ink for inkjet printing, etc. can be used, and its type can be appropriately selected depending on the type of organic pigment used together or the type of organic solvent described later. Specifically, the dispersant helps the pigment to be uniformly dispersed in the dispersion, and any nonionic, anionic, or cationic dispersant can be used. More 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, quaternary amine, etc. can be used, and these can be used alone or in combination of two or more.
[0149] The dispersant may be included in an amount of 1 to 5 wt% based on the total amount of the yellow pigment dispersion. If the content of the dispersant is less than 1 wt%, pigment dispersibility may be reduced, and if it exceeds 20 wt%, there may be concerns such as reduced developability.
[0150] For example, the dispersion resin may use an acrylic resin containing a carboxyl group, which can not only improve the stability of the yellow pigment dispersion but also improve the patternability of the pixels.
[0151] The above dispersion resin may be included in an amount of 3 wt% to 10 wt% based on the total amount of the yellow pigment dispersion.
[0152] As the above solvent, 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.
[0153] Considering the solubility, pigment dispersibility, and applicability of the dispersion resin, it may be preferable for these solvents to be included in a remainder amount, for example, 60 wt% to 90 wt%, of the total amount of the yellow pigment dispersion.
[0154] For example, the pigment used together with the yellow pigment dispersion may be an organic pigment, such as a red pigment or a green pigment, and the organic pigment may be a finely divided one. The finely divided organic pigment may be a salt-milled organic pigment. Specifically, in order to increase the transmittance and contrast ratio of a color filter or inkjet printing, it may be preferable for the organic pigment to be finely divided. In addition, it may be more preferable to salt-mill the organic pigment by grinding it with an inorganic salt using a kneader or a mixing device that rotates and orbits three stirring blades respectively, so that the primary particle diameter of the organic pigment becomes even finer. Among these, it may be preferable to use an organic pigment obtained by salt-milling using a mixing device that rotates and orbits three stirring blades respectively. In this case, the primary particle diameter of the pigment can be further made finer and more uniform by salt milling.
[0155] Examples of the above red pigments include perylene pigments, anthraquinone pigments, azo pigments, diazo pigments, quinacridone pigments, anthracene pigments, etc. Specific examples of the above red pigments include, but are not limited to, perylene pigments, quinacridone pigments, naphthol AS, cycomine pigments, anthraquinone (sudan I, II, III, R), bis azo, benzopyran, etc.
[0156] When the photosensitive resin composition according to one embodiment is a red photosensitive resin composition including the red pigment, the red pigment may be included in the composition in the form of a pigment dispersion.
[0157] Examples of the green pigment include, but are not limited to, Pigment Green 58, 59, etc.
[0158] When the photosensitive resin composition according to one embodiment is a green photosensitive resin composition including the green pigment, the green pigment may be included in the composition in the form of a pigment dispersion.
[0159] When the pigment is a red pigment, the photosensitive resin composition may necessarily include a binder resin, and in this case, the photosensitive resin composition may include 10 to 30 wt% of the yellow pigment dispersion; 20 to 50 wt% of the red pigment dispersion; 1 to 10 wt% of the binder resin; 0.1 to 5 wt% of the photopolymerizable compound; 0.01 to 3 wt% of the photopolymerization initiator; and the remainder of the solvent, based on the total amount of the photosensitive resin composition.
[0160] When the pigment is a green pigment, the photosensitive resin composition may not include a binder resin (a binder resin-free photosensitive resin composition), and in this case, the photosensitive resin composition may include 20 wt% to 40 wt% of the yellow pigment dispersion; 25 wt% to 55 wt% of the green pigment dispersion; 1 wt% to 10 wt% of the photopolymerizable compound; 0.1 wt% to 5 wt% of the photopolymerization initiator; and the remainder of the solvent, based on the total amount of the photosensitive resin composition.
[0161] By changing the composition of the photosensitive resin composition as described above depending on the type of the pigment, a colored photosensitive resin composition for a color filter having excellent dispersibility and dispersion stability, improved coloring power, and an effect of suppressing pattern residue can be obtained.
[0162] The above binder resin may be an acrylic resin.
[0163] 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.
[0164] 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.
[0165] 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.
[0166] 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.
[0167] 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.
[0168] For example, the binder resin may further include an epoxy resin together with the acrylic resin.
[0169] The weight average molecular weight of the binder resin may be 3,000 g / mol to 150,000 g / mol, for example 5,000 g / mol to 50,000 g / mol, for example 20,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the binder resin is within the above range, the photosensitive resin composition has excellent physical and chemical properties, appropriate viscosity, and excellent adhesion to a substrate during the manufacture of a color filter.
[0170] The acid value of the above binder resin may be 15 mgKOH / g to 60 mgKOH / g, for example, 20 mgKOH / g to 50 mgKOH / g. When the acid value of the binder resin is within the above range, the resolution of the pixel pattern is excellent.
[0171] The above photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond.
[0172] The above photopolymerizable compound has the above ethylenically unsaturated double bond, and thus can form a pattern with excellent heat resistance, light resistance, and chemical resistance by causing sufficient polymerization upon exposure in the pattern forming process.
[0173] Specific examples of the above photopolymerizable compound include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol Examples 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.
[0174] Examples of commercially available products of the above photopolymerizable compounds are as follows. An example of the monofunctional ester of (meth)acrylic acid is Aronix M-101 from Toagosei Chemical Industry 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.
[0175] The above photopolymerizable compound may be used by treating it with an acid anhydride to provide better developing properties.
[0176] The preferred content range of the photopolymerizable compound is as described above. When the photopolymerizable compound is included within the above range, sufficient curing occurs upon exposure in the pattern formation process, resulting in excellent reliability and excellent developability in an alkaline developer.
[0177] 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.
[0178] 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.
[0179] 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.
[0180] Examples of the above thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2-chlorothioxanthone, etc.
[0181] Examples of the above benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyldimethyl ketal, etc.
[0182] 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.
[0183] 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.
[0184] 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.
[0185] 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.
[0186] 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.
[0187] The preferred content range of the photopolymerization initiator is as described above. When the photopolymerization initiator is included within the above range, sufficient curing occurs during exposure in the pattern formation process, thereby achieving excellent reliability. The pattern has excellent heat resistance, light resistance, and chemical resistance, and also has excellent resolution and adhesion, and can prevent a decrease in transmittance due to unreacted initiator.
[0188] The solvent may be a pigment dispersion containing a compound according to one embodiment, a material that is compatible with the pigment, the binder resin, the photopolymerizable compound, and the photopolymerization initiator but does not react with them.
[0189] 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.;
[0190] Among these, glycol ethers such as ethylene glycol monoethyl ether, taking into account compatibility and reactivity; ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; esters such as 2-hydroxypropionate ethyl; carbitols such as diethylene glycol monomethyl ether; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate; and / or ketones such as cyclohexanone can be used.
[0191] The photosensitive resin composition may further include other additives such as malonic acid; 3-amino-1,2-propanediol; a silane coupling agent; a leveling agent; a fluorinated surfactant; a radical polymerization initiator; or a combination thereof to prevent stains or spots during application, improve leveling performance, and prevent the formation of residues due to non-development.
[0192] Examples of the above silane coupling agent include trimethoxysilyl benzoic acid, γ-methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, γ-glycidoxy propyl trimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, etc., and these may be used alone or in combination of two or more.
[0193] An example of the above fluorinated surfactant is BM-1000 from BM Chemie. ® , BM-1100 ® Back; Mecha Pack F 142D by Dai Nippon Inki Kagaku Kogyo Co., Ltd. ® , East F 172 ® , East F 173 ® , East F 183 ® Back; Prorad FC-135 from Sumitomo 3M Co., Ltd. ® , East FC-170C ® , East FC-430 ® , East FC-431 ® Saffron S-112 from Asahi Glass Co., Ltd. ® , East S-113 ® , East S-131 ® , East S-141 ® , East S-145 ® SH-28PA from Toray Silicone Co., Ltd. ® , East-190 ® , East-193 ® , SZ-6032 ® , SF-8428 ® Examples of commercial products include:
[0194] The content of the above additives can be easily adjusted according to the desired properties.
[0195] Another embodiment provides a cured film manufactured using the photosensitive resin composition.
[0196] Another embodiment provides a color filter including the cured film.
[0197] The pattern formation process within the above color filter is as follows.
[0198] A process for applying the photosensitive resin composition onto a supporting substrate by spin coating, slit coating, inkjet printing, etc.; a process for drying the applied photosensitive resin composition to form a photosensitive resin composition film; a process for exposing the photosensitive resin composition film to light; a process for developing the exposed photosensitive resin composition film with an alkaline aqueous solution to produce a photosensitive resin film; and a process for heat-treating the photosensitive resin film. Since the conditions for the process, etc. are widely known in the art, a detailed description thereof will be omitted herein.
[0199] Another embodiment provides a CMOS image sensor including the color filter.
[0200]
[0201] Hereinafter, preferred embodiments of the present invention are described. However, the following examples are only preferred embodiments of the present invention, and the present invention is not limited to the following examples.
[0202]
[0203] (Preparation of yellow pigment dispersion)
[0204] A yellow pigment dispersion having the compositions shown in Tables 1 and 2 below was prepared.
[0205] dispersant
[0206] Tertiary amine dispersant Efka PX 4310 (amine value 19 mgKOH / g, BASF)
[0207] Dispersion resin
[0208] Acrylic binder resin (molecular weight 6000 g / mol, acid value 70 KOHmg / g, double bond equivalent 370 g / mol, Showa Denko)
[0209] menstruum
[0210] Propylene glycol monomethyl ether acetate (PGMEA, Sigma-Aldrich)
[0211]
[0212] (Unit: weight%) Yellow pigment dispersion Pigment Y139 Dispersant Dispersing aid (in parentheses is weight) Dispersing resin Solvent Pigment Dispersion 1124- 480 Pigment dispersion 2123 Chemical formula 1-1 (1) 480 Pigment dispersion 3122 Chemical formula 1-1 (2) 480 Pigment dispersion 4123 Chemical formula 1-3 (1) 480 Pigment dispersion 5122 Chemical formula 1-3 (2) 480 Pigment dispersion 6123 Chemical formula 1-10 (1) 480 Pigment dispersion 7122 Chemical formula 1-10 (2) 480 Pigment dispersion 8123 Chemical formula C-1 (1) 480 Pigment dispersion 9123 Chemical formula C-1 (2) 480 Pigment dispersion 10123 Chemical formula C-2 (1)480 pigment dispersion 11123 chemical formula C-2 (2)480
[0213] (Unit: weight%)Yellow pigment dispersionPigment Y185DispersantDispersing aid(in parentheses is weight)Dispersing resinSolventPigmentDispersion 12124- 480Pigment dispersion 13123Chemical formula 1-1 (1)480Pigment dispersion 14122Chemical formula 1-1 (2)480Pigment dispersion 15123Chemical formula 1-3 (1)480Pigment dispersion 16122Chemical formula 1-3 (2)480Pigment dispersion 17123Chemical formula 1-10 (1)480Pigment dispersion 18122Chemical formula 1-10 (2)480Pigment dispersion 19123Chemical formula C-1 (1)480Pigment dispersion 20123Chemical formula C-1 (2)480Pigment dispersion 21123Chemical formula C-2 (1)480 pigment dispersion 22123 chemical formula C-2 (2)480
[0214] [Chemical Formula 1-1]
[0215]
[0216] [Chemical Formula 1-3]
[0217]
[0218] [Chemical Formula 1-10]
[0219]
[0220] [Chemical Formula C-1]
[0221]
[0222] [Chemical Formula C-2]
[0223]
[0224]
[0225] (Manufacture of photosensitive resin composition)
[0226] A photosensitive resin composition having the compositions shown in Tables 3 and 4 below was prepared. In Table 3 below, the red pigment in the red pigment dispersion is R254, and in Table 4 below, the green pigment in the green pigment dispersion is G58. In Tables 3 and 4 below, the binder resin is an acrylic binder resin (molecular weight 6000 g / mol, acid value 70 KOHmg / g, double bond equivalent 370 g / mol, Showa Denko Co., Ltd.), the photopolymerizable compound is DPHA (Nippon Gunyaku Co., Ltd.), the photopolymerization initiator is SPI-03 (Samyang Co., Ltd.), and the solvent is propylene glycol monomethyl ether acetate (PGMEA, Sigma-Aldrich Co., Ltd.).
[0227]
[0228] (Unit: weight%)Yellow pigment dispersion (weight in parentheses)Red pigment dispersion (SAKATA)Binder resinPhotopolymerizable compoundPhotopolymerization initiatorSolvent (PGMEA)Comparative example 1Pigment dispersion 1 (20)36410.238.8Example 1Pigment dispersion 2 (20)36410.238.8Example 2Pigment dispersion 3 (20)36410.238.8Example 3Pigment dispersion 4 (20)36410.238.8Example 4Pigment dispersion 5 (20)36410.238.8Example 5Pigment dispersion 6 (20)36410.238.8Example 6Pigment dispersion 7 (20)36410.238.8Comparative example 2 Pigment dispersion 8 (20) 364 10.238.8 Comparative example 3 Pigment dispersion 9 (20) 364 10.238.8 Comparative example 4 Pigment dispersion 10 (20) 364 10.238.8 Comparative example 5 Pigment dispersion 11 (20) 364 10.238.8
[0229] (Unit: weight%) Yellow pigment dispersion (weight in parentheses) Green pigment dispersion (SANYO) Photopolymerizable compound Photopolymerization initiator Solvent (PGMEA) Comparative example 6 Pigment dispersion 12 (30) 402.50.527 Example 7 Pigment dispersion 13 (30) 402.50.527 Example 8 Pigment dispersion 14 (30) 402.50.527 Example 9 Pigment dispersion 15 (30) 402.50.527 Example 10 Pigment dispersion 16 (30) 402.50.527 Example 11 Pigment dispersion 17 (30) 402.50.527 Example 12 Pigment dispersion 18 (30) 402.50.527 Comparative example 7 Pigment Dispersion 19 (30) 402.50.527 Comparative Example 8 Pigment Dispersion 20 (30) 402.50.527 Comparative Example 9 Pigment Dispersion 21 (30) 402.50.527 Comparative Example 10 Pigment Dispersion 22 (30) 402.50.527
[0230] (evaluation)
[0231] Viscosity measurement
[0232] For each of the photosensitive resin compositions of Examples 1 to 12 and Comparative Examples 1 to 10, the viscosity (25°C) immediately after manufacture and the viscosity (25°C) after storage at room temperature (25°C) for one week after manufacture were measured using a viscometer (Thermo Fisher Scientific Inc. HAAKE MARS 40), and the results are shown in Table 5 below.
[0233]
[0234] Spectroscopic measurements
[0235] On glass (118 mm X 118 mm, thickness 0.7 mm), each of the photosensitive resin compositions of Examples 1 to 12 and Comparative Examples 1 to 10 was applied by spin coating, and heated at 100°C for 3 minutes using a hot plate to form a coating layer of 0.6 μm. Then, an i-line stepper exposure device (Nikon) was used at 2500 J / m 2Specimens were formed by exposing to energy and heating on a 200°C hot plate for 5 minutes. The transmittance of the obtained specimens at a wavelength of 470 nm was measured using MCPD (Otsuka Electronics Co., Ltd.), and the results are shown in Table 5 below.
[0236]
[0237] Residue (resolution) evaluation
[0238] On an 8-inch silicon wafer, each of the photosensitive resin compositions of Examples 1 to 12 and Comparative Examples 1 to 10 was applied by spin coating, and heated at 100°C for 3 minutes using a hot plate to form a 0.6 μm coating layer. Then, an i-line stepper exposure device (Nikon) was used at 2500 J / m 2 After exposure to energy, the film was developed using a 0.38% aqueous tetramethylammonium hydroxide solution (ENF Co.) using a puddle method, and then rinsed with purified water. After that, the film was heated on a 200°C hot plate for 5 minutes to form a patterned specimen. The formed specimen was used to find a pattern with a CD of 1.4 μm using a CD-SEM (Hitachi Co.), and the residue between the patterns was quantified according to the following criteria according to the degree, and the results are shown in Table 5 below. If the degree of residue was 1 to 2, the residue suppression effect was evaluated as excellent.
[0239] <Residue Evaluation Criteria>
[0240]
[0241]
[0242] (Unit: wt%) Viscosity immediately after manufacturing (cPs) Viscosity after 1 week (cPs) Permeability (%) Residue Comparative Example 14.02 4.03 3.53 Example 14.06 4.12 63 Example 24.08 4.13 2.13 Example 33.85 3.85 3.11 Example 43.88 3.9 2.61 Example 54.01 42.82 Example 64.03 4.04 2.22 Comparative Example 24.3 4.42 4.54 Comparative Example 34.35 4.48 4.34 Comparative Example 44.43 4.44 4.25 Comparative Example 54.45 4.47 4.15 Comparative Example 64.71 4.65 6.43 Example 74.744.575.23 Example 84.74.794.83 Example 93.753.765.81 Example 103.83.785.31 Example 114.724.735.52 Example 124.694.75.03 Comparative Example 74.834.836.74 Comparative Example 84.874.866.64 Comparative Example 95.035.046.65 Comparative Example 105.015.026.55
[0243] From the above Table 5, it can be confirmed that the photosensitive resin composition according to one embodiment significantly improves the dispersibility and dispersion stability of pigment particles by using a yellow pigment dispersion liquid containing a yellow pigment synergist that helps disperse pigments while also having light absorption properties, thereby preventing agglomeration between pigments used, thereby having improved coloring power while also having an excellent effect of suppressing residue in patterns. In other words, it can be easily predicted that fine patterning and thin film formation can be achieved by using the photosensitive resin composition according to one embodiment.
[0244]
[0245] The present invention is not limited to the above-described embodiments, but can be manufactured in a variety of different forms. Those skilled in the art will appreciate that the present invention can be implemented in other specific forms without altering the technical spirit or essential characteristics of the present invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.
Claims
1. A yellow pigment dispersion comprising a compound represented by the following chemical formula 1 and a yellow pigment; pigment; photopolymerizable compound; photopolymerization initiator; and menstruum A photosensitive resin composition comprising: [Chemical Formula 1] In the above chemical formula 1, X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group or a combination thereof, L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 1 Inland R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or an acid group, provided that R 1 Inland R 4 At least one of them is acidic.
2. In paragraph 1, The acid group above is *-SO3 - , a photosensitive resin composition having a carboxyl group, a phosphoric acid group or a phosphonic acid group.
3. In paragraph 1, Above *-N(R a )-* is a photosensitive resin composition represented by the following chemical formula N: [Chemical formula N] In the above chemical formula N, L 5 is a substituted or unsubstituted C1 to C10 alkylene group, R 5 is an acidic group.
4. In paragraph 1, The above chemical formula 1 is a photosensitive resin composition represented by the following chemical formula 1A or chemical formula 1B: [Chemical Formula 1A] [Chemical Formula 1B] In the above chemical formulas 1A and 1B, X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group or a combination thereof, L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 1 Inland R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or an acidic group.
5. In paragraph 1, The above R 1 Inland R 4 A photosensitive resin composition, wherein at least two of the components are acid groups.
6. In paragraph 1, The above R 1 Inland R 4 A photosensitive resin composition, wherein at least three of the groups are acidic.
7. In paragraph 6, The above acidic group is a photosensitive resin composition having the same type.
8. In paragraph 1, The above acidic groups are different types of photosensitive resin compositions.
9. In paragraph 1, The above compound is a photosensitive resin composition represented by any one of the following chemical formulas 1-1 to 1-11. [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] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] 10. In paragraph 1, The above pigment is a red pigment dispersion containing a red pigment, and the photosensitive resin composition further contains a binder resin.
11. In paragraph 10, The above photosensitive resin composition is based on the total amount of the above photosensitive resin composition. 10 to 30 wt% of the above yellow pigment dispersion; 20 to 50 wt% of the above red pigment dispersion; 1 to 10 wt% of the above binder resin; 0.1 wt% to 5 wt% of the photopolymerizable compound; 0.01 wt% to 3 wt% of the above photopolymerization initiator; and The above solvent residue A photosensitive resin composition comprising:
12. In paragraph 1, The above pigment is a photosensitive resin composition which is a green pigment dispersion containing a green pigment.
13. In paragraph 12, The above photosensitive resin composition is based on the total amount of the above photosensitive resin composition. 20 to 40 wt% of the above yellow pigment dispersion; 25 wt% to 55 wt% of the above green pigment dispersion; 1 to 10 wt% of the photopolymerizable compound; 0.1 wt% to 5 wt% of the photopolymerization initiator; and The above solvent residue A photosensitive resin composition comprising:
14. A cured film manufactured using a photosensitive resin composition according to any one of claims 1 to 13.
15. A color filter comprising the cured film of Article 14.
16. A CMOS image sensor including the color filter of claim 15.
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