KR102222403B1 - Colored photosensitive resin composition for green pixel - Google Patents

Abstract

The present invention relates to a colored photosensitive resin composition for a green pixel, a color filter manufactured using the same, and a liquid crystal display device including the same.

Description

Colored photosensitive resin composition for green pixels {COLORED PHOTOSENSITIVE RESIN COMPOSITION FOR GREEN PIXEL}

The present invention relates to a colored photosensitive resin composition for a green pixel, a color filter manufactured using the same, and a liquid crystal display device including the same.

Color filters are widely used in imaging devices, liquid crystal display devices, and the like, and their application range is rapidly expanding. A color filter used in a color liquid crystal display device, an image pickup device, or the like is usually applied by spin coating a colored photosensitive resin composition for green pixels containing a colorant corresponding to each color of red, green, and blue on a patterned substrate with a black matrix. After evenly applying, heat-drying (hereinafter, sometimes referred to as pre-baking) to expose and develop the formed coating film, and further heat-curing (hereinafter, also referred to as post-baking) if necessary, for each color. It is manufactured by repeatedly forming pixels of each color. Recently, a color filter for a liquid crystal display (LCD) is required to reproduce a high color, and a change of color coordinates is also required by a change of a backlight. To this end, there is a need for a colored photosensitive resin composition for green pixels that has good color reproducibility and can easily change color coordinates when the backlight is changed.

In a color liquid crystal display, the color reproduction range is a range indicated by a triangle connecting the chromaticity coordinates of red, green, and blue in the XYZ color system, and is expressed as an area ratio to the NTSC (National Television System Committee) standard. The color reproduction range of CRT is about 70% of NTSC standard ratio. The color reproducibility is wider than the EBU (European Broadcasting Union) standard, and the aforementioned NTSC standard is a good standard, and the chromaticity coordinates (x, y) in the XYZ color system of red, green, blue, and each color are red (0.670, 0.330), respectively. ), green (0.210, 0.710), blue (0.140, 0.080). In the case of a conventional liquid crystal display device of NTSC 72% or less (EBU standard), the green pixels of the color filter are the main pigments, and C.I. Pigment Green 36 or C.I. Pigment Green 58 was used, and C.I. Pigment Yellow 150 or C.I. A green pixel was formed by combining Pigment Yellow 138 and the like. In the Digital Cinema Initiatives (DCI) required by the ITU-R BT.2020 broadcast standard (chromatic coordinates (x, y) are red (0.708, 0.292), green (0.170, 0.797), blue (0.131, 0.046), respectively). The chromaticity coordinates (x, y) of are red (0.680, 0.320), green (0.265, 0.690), and blue (0.150, 0.060), respectively, and the chromaticity coordinates (x, y) in Adobe are red (0.640, 0.330), respectively. , Green (0.210, 0.710), blue (0.150, 0.060).

Accordingly, Korean Patent Laid-Open Publication No. 10-2010-0121551 discloses a CI that has high transmittance and contrast ratio as a color material for green pixels. Pigment Green 58 is used, but CI Pigment Green 58 has low colorability, which makes it difficult to implement a pixel in a high color reproduction area.

In addition, when using an existing colorant to form a green pixel of a color filter having a wide color reproducibility in a liquid crystal display device, there is a method of increasing the concentration of the pigment or forming a thicker coating film of the pattern. However, there is a problem of lack of fairness such as line tearing of the pattern, lowering of straightness, and generation of voids in the pattern due to undercut. Therefore, it is urgent to improve the colorability and color reproducibility of the color material of green pixels.

Republic of Korea Patent Publication No. 10-2010-0121551

In order to solve the above problems, an object of the present invention is to provide a colored photosensitive resin composition for a green pixel capable of forming a thin film without increasing the pigment concentration. In addition, it is an object of the present invention to provide a high-quality color filter having a wide color reproducibility with the colored photosensitive resin composition for a green pixel. In addition, another object of the present invention is to provide a liquid crystal display device having the color filter of the present invention.

The present invention includes a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D) and a solvent (E), wherein the colorant (A) is represented by the following formula (1). Yellow pigment and CI containing the compound Pigment Blue 15:6, C.I. Pigment Blue 15:3 and C.I. It provides a colored photosensitive resin composition for a green pixel comprising a blue pigment containing at least one selected from Pigment Blue 15:4.

[Formula 1]

In Formula 1, R1 to R13 are each independently a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO ₃ H, -COOH, -SO ₃ M, -COOM, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent, wherein M is a monovalent to trivalent metal or alkyl ammonium, and adjacent groups of R1 to R4 are integrated. An aromatic ring which may have a substituent can be formed, and R10 to R13 can form an aromatic ring which may have a substituent by uniting adjacent groups.

A color filter formed by forming the colored photosensitive resin composition for a green pixel of the present invention in a predetermined pattern and then exposing and developing it is provided. Further, an image pickup device and a liquid crystal display device including the color filter of the present invention are provided.

The colored photosensitive resin composition for a green pixel of the present invention has excellent coloring power and transmittance, has a high development speed, and does not cause peeling of the pattern. In addition, it is possible to provide a colored photosensitive resin composition for a green pixel having a wide color reproducibility without thickening and maintaining a pigment concentration applied to a liquid crystal display of NTSC 72% or less. That is, it is possible to provide a colored photosensitive composition for a green pixel having a wide color reproducibility capable of forming a thin film without increasing the pigment concentration.

Therefore, the colored photosensitive resin composition for a green pixel of the present invention can be very usefully used in manufacturing a color filter.

Hereinafter, the present invention will be described in more detail.

Conventionally, the use of high-concentration pigments and thick pattern formation, which are methods for forming green pixels of such a color filter with wide color reproducibility in liquid crystal display devices, are used to cut lines of the pattern, decrease the straightness, and voids in the pattern due to undercut. There is a problem of lack of fairness such as occurrence.

In order to solve this problem, the present inventors have found that the above problems can be solved by including a specific blue pigment and a specific yellow pigment in the colored photosensitive composition and completed the present invention.

That is, the present invention includes a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E), and the colorant (A) is represented by the following formula (1). Yellow pigment and CI containing the compound Pigment Blue 15:6, C.I. Pigment Blue 15:3 and C.I. It provides a colored photosensitive resin composition for a green pixel comprising a blue pigment containing at least one selected from Pigment Blue 15:4.

[Formula 1]

In Formula 1, R1 to R13 are each independently a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO ₃ H, -COOH, -SO ₃ M, -COOM, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent, wherein M is a monovalent to trivalent metal or alkyl ammonium, and adjacent groups of R1 to R4 are integrated. An aromatic ring which may have a substituent can be formed, and R10 to R13 can form an aromatic ring which may have a substituent by uniting adjacent groups.

Hereinafter, the colored photosensitive resin composition for a green pixel of the present invention will be described in detail for each component.

Colorant (A)

The present invention is a colored photosensitive composition for a green pixel, a yellow pigment comprising a compound represented by the following formula (1) and a selection of CI Pigment Blue 15:6, CI Pigment Blue 15:3 and CI Pigment Blue 15:4 It contains a blue pigment containing at least one type of.

Pigment( a1 )

First, the compound represented by the following formula (1) will be described.

The compound represented by the following formula (1) is an essential component included in the yellow pigment.

[Formula 1]

In Formula 1, R1 to R13 are each independently a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO ₃ H, -COOH, -SO ₃ M, -COOM, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent, wherein M is a monovalent to trivalent metal or alkyl ammonium, and adjacent groups of R1 to R4 are integrated. , An aromatic ring which may have a substituent can be formed, and the adjacent groups of R10 to R13 are united to form an aromatic ring which may have a substituent.

The aromatic ring used herein includes a hydrocarbon aromatic ring and a heteroaromatic ring. Examples of the hydrocarbon aromatic ring may include a benzene ring, a naphthalene ring, an anthracene ring and/or a phenanthrene ring. In addition, as the heteroaromatic ring, a pyridine ring, a pyrazine ring, a pyrrole ring, a quinoline ring, a quinoxaline ring, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, an oxazole ring, a thiazole ring, an imidazole ring , A pyrazole ring, an indole ring and/or a carbazole ring, and the like.

And The compound represented by Formula 1 may be any one selected from compounds represented by Formulas 2 to 4 below.

[Formula 2]

[Formula 3]

[Formula 4]

^{R 14} to R ²⁸ , R ²⁹ to R ⁴³ of Formulas 2 to 4 And R ⁴⁴ to R ⁶⁰ are each independently a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO ₃ H, -COOH, -SO ₃ M, -COOM, a phthalimidomethyl group which may have a substituent or a sulfamoyl group which may have a substituent, and M is a monovalent to trivalent metal or alkyl ammonium.

Specifically, the compounds represented by Chemical Formulas 1 to 4 will be described.

The compounds represented by Chemical Formulas 1 to 4 are also referred to as quinophthalone pigments. R1 to R13, R ¹⁴ to R ²⁸ , R ²⁹ to R ^{43 of Formulas 1 to 4} And ^{examples of the halogen atom of R 44} to R ⁶⁰ include fluorine, chlorine, bromine and/or iodine. In addition, the alkyl group which may have the above substituents is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, neopentyl group, n-hexyl group, n-octyl group, stearyl group, and /Or a linear or branched alkyl group such as a 2-ethylhexyl group; In addition, trichloromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3-tetrafluoropropyl group, 2-ethoxyethyl group , 2-butoxyethyl group, 2-nitropropyl group, benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group and/or 2,4-dichloro An alkyl group having a substituent such as a benzyl group; may be mentioned. In addition, the alkoxyl group which may have the above substituents is a methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutyloxy group, tert-butyloxy group, neopentyloxy group, 2,3 Linear or branched alkoxyl groups such as -dimethyl-3-pentoxy, n-hexyloxy group, n-octyloxy group, stearyloxy group, and/or 2-ethylhexyloxy group; In addition, trichloromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropyloxy group, 2,2-ditrifluoromethyl And an alkoxyl group having a substituent such as a propoxy group, a 2-ethoxyethoxy group, a 2-butoxyethoxy group, a 2-nitropropoxy group, and/or a benzyloxy group. Further, the aryl group which may have the above substituents may include aryl groups such as a phenyl group, a naphthyl group and/or an anthranyl group; In addition, p-methylphenyl group, p-bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-aminophenyl group, 2-methyl-4-chlorophenyl group, Having a substituent such as 4-hydroxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group and/or 2-aminoanthraquinonyl group Aryl group; may be mentioned. Moreover, -SO3H and -COOH are mentioned as an acidic group, As a monovalent-trivalent metal salt of these acidic groups, sodium salt, potassium salt, magnesium salt, calcium salt, iron salt, and/or aluminum salt, etc. are mentioned. Further, examples of the acidic alkyl ammonium salt include ammonium salts of long-chain monoalkylamines such as octylamine, laurylamine and/or stearylamine; Quaternary alkyl ammonium salts such as palmityl trimethyl ammonium, dilauryl dimethyl ammonium, and distearyl dimethyl ammonium salt; and the like. As the substituent in the phthalimidomethyl group (C ₆ H ₄ (CO) ₂ N-CH ₂ -) which may have a substituent and the sulfamoyl group (H ₂ NSO ₂ -) which may have the substituent, the halogen atom , An alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and/or an aryl group which may have a substituent.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 may be included in a weight fraction of 5 to 75% by weight based on the total weight of solids in the colorant (A), preferably 10 to 70% by weight, more Preferably it may be included in 20 to 60% by weight. If the compound represented by Formula 1 among the colorants (A) is in the above range based on the above criteria, the content of the colorant is lowered to prevent the problem of reducing reliability in which the colorant is eluted by the organic solvent, and it is preferable because of its excellent sensitivity.

And it may further include a pigment commonly used in the art.

That is, the yellow pigment may further include various pigments used for printing ink, inkjet ink, and the like. In particular, organic and inorganic pigments include compounds classified as pigments in the color index (published by The Society of Dyers and Colorists), and more specifically, pigments with the following color index (CI) numbers. Although it can be mentioned, it is not necessarily limited to these.

C.I. Pigment Yellow 13, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 129, 137, 138, 139, 147,148, 150, 153, 154, 166, 173, 180 And 185

Each of the yellow pigments may be used alone or in combination of two or more. In particular, among the above-described yellow dyes, at least one pigment selected from CI pigment yellow 129, CI pigment yellow 138, pigment yellow 139, pigment yellow 150, and CI pigment yellow 185 may be preferably used.

And the blue pigment of the present invention may include any one or more selected from C.I pigment blue 15:3, 15:4 and 15:6. According to a preferred embodiment of the present invention, the blue pigment may preferably include CI Pigment Blue 15:3 and/or CI Pigment Blue 15:4, and most preferably CI Pigment Blue 15: May contain 4.

According to a preferred embodiment of the present invention, the content of the blue pigment may be 5 to 50% by weight, preferably 5 to 45% by weight, based on the total weight of the solids in the colorant (A). .

If included in the range of the above criteria, the colored photosensitive resin composition for green pixels has excellent sensitivity, facilitates pattern formation, and has sufficient color density of pixels. In addition, since the omission property of the non-pixel portion does not decrease during development, it is difficult to generate a residue, which is preferable. According to a preferred embodiment of the present invention, the weight ratio of the yellow pigment and the blue pigment may be 90:10 to 70:30, preferably 80:20 to 60:40. When the weight ratio is in the above range, high color reproducibility is excellent.

And the content of the pigment (a1) is in the range of 10 to 80% by weight, preferably 30 to 75% by weight, based on the total weight of the solid content in the colorant (A). If the content of the pigment is in the range of 10 to 90% by weight based on the above, it is preferable because the viscosity is low, storage stability is excellent, and dispersion efficiency is high, so that it is effective to increase the contrast ratio. As for the pigment, it is preferable to use a pigment dispersion in which the particle diameter is uniformly dispersed.

An example of a method for uniformly dispersing the particle diameter of the pigment may include a method of dispersing by containing a pigment dispersant (a2). According to this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained. have.

Specific examples of the above pigment dispersant (a3) include surfactants such as cationic, anionic, nonionic, amphoteric, polyester, and polyamine, and these may be used alone or in combination of two or more. Can be used.

Pigment dispersant ( a3 )

The pigment dispersant (a3) is added for deagglomeration and stability maintenance of the pigment, and those generally used in the art may be used without limitation. It is preferable to contain an acrylate-based dispersant (hereinafter referred to as an acrylic dispersant) including BMA (butyl methacrylate) or DMAEMA (N,N-dimethylaminoethyl methacrylate). At this time, it is preferable to apply the acrylic dispersant prepared by the living control method as presented in Korean Patent Application No. 2004-0014311. As a commercial product of the acrylate-based dispersant manufactured through the living control method, DISPER BYK- 2000, DISPER BYK-2001, DISPER BYK-2070 and/or DISPER BYK-2150.

Each of the acrylic dispersants exemplified above may be used alone or in combination of two or more. As the dispersant (a3), other resin type pigment dispersants may be used in addition to the acrylic dispersant described above. As the pigment dispersant of the other resin type, a known resin type pigment dispersant, in particular, of a polycarboxylic acid ester typified by polyurethane, polyacrylate, unsaturated polyamide, polycarboxylic acid, polycarboxylic acid (partial) Amine salts, ammonium salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long chain polyaminoamide phosphate salts, esters of hydroxyl group-containing polycarboxylic acids and modified products thereof, or free ) An oily dispersant such as an amide formed by the reaction of a polyester having a carboxyl group with a poly (lower alkyleneimine) or a salt thereof; Water-soluble resins or water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinyl pyrrolidone; Polyester; Modified polyacrylate; And phosphate esters and adducts of ethylene oxide/propylene oxide. Commercially available products of the above resin-type dispersants include cationic resin dispersants, for example, BYK Chemie's brand names: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK- 164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; BASF's brand names: EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA- 4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; Trade names of Lubirzol: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10; Kawaken Fine Chemical's trade names: Hinoact T-6000, Hinoact T-7000, Hinoact T-8000; Ajinomoto's brand names: AJISPUR PB-821, Ajisper PB-822, Ajisper PB-823; Kyoeisha Chemicals' brand name: FLORENE DOPA-17HF, Floren DOPA-15BHF, Floren DOPA-33, Floren DOPA-44, and the like. In addition to the above acrylic dispersants, other resin type pigment dispersants may be used alone or in combination of two or more, or may be used in combination with acrylic dispersion.

The amount of the dispersant (a3) used is in the range of 5 to 60 parts by weight, more preferably 15 to 50 parts by weight, based on 100 parts by weight of the solid content of the pigment (a1) to be used. If the content of the dispersant (a3) exceeds 60 parts by weight based on the above, the viscosity may increase, and if it is less than 5 parts by weight, it may be difficult to atomize the pigment or cause problems such as gelation after dispersion.

dyes( a2 )

The colorant of the present invention may further include a dye (a2) generally used in the art.

The dye (a2) may be additionally used without limitation as long as it has solubility in an organic solvent. Preferably, it is preferable to use a dye that has solubility in an organic solvent and can secure reliability such as solubility in an alkali developer, heat resistance, and solvent resistance. The dye may be selected from acid dyes having acidic groups such as sulfonic acid or carboxylic acid, salts of acidic dyes and nitrogen-containing compounds, sulfonamides of acidic dyes, and derivatives thereof. In addition, azo-based, xanthene-based, phthalocyanine Acid dyes of the system and their derivatives can also be selected. Preferably, the dye may be a compound classified as a dye in the color index (published by The Society of Dyers and Colorists), or a known dye described in the dye note (color dyeing company).

Specific examples of the dye,

C.I. As a solvent dye,

C.I. Yellow dyes, such as solvent yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94, 98, 99, 151, 162, 163;

C.I. Among solvent dyes, C.I. has excellent solubility in organic solvents. Solvent Yellow 14, 16, 21, 56, 151, 79, 93 are preferred, and C.I. Solvent Yellow 21, 79; Is more preferable.

Also, C.I. As an acid dye, CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251, etc. And yellow dyes. In addition, among the acid dyes, C.I. acid yellow, which has excellent solubility in organic solvents, is preferable.

Also as a C.I. direct dye,

CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129 , 136, 138, 141, and other yellow dyes.

Also, C.I. As a modanto dye

Yellow dyes, such as C.I. modanto yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65, etc. are mentioned.

These dyes (a3) can be used alone or in combination of two or more.

The content of the colorant (A) is preferably 5 to 60% by weight, preferably 10 to 50% by weight, based on the total weight of solids in the colored photosensitive resin composition for green pixels of the present invention. In the case where the colorant (A) is included in the above-described range, the color density of the pixel is sufficient even when the thin film is formed, and the omission property of the non-pixel portion is not lowered during development, so that the residue is difficult to occur, so it is preferable.

Alkali Soluble Resin (B)

Alkali-soluble resin is a component that imparts solubility to the alkali developer used in the developing process, and can be used without limitation if it is soluble in the alkaline developer. In order to dissolve in an alkali developer, it is a common method to introduce an acid value by introducing a carboxyl group into the resin. do. It can be prepared by copolymerizing an ethylenically unsaturated monomer (b1) having a carboxyl group, or by reacting an acid anhydride to a resin copolymer (b2) having a hydroxyl group to give an acid value. At this time, the acid value of the alkali-soluble resin (B) is preferably 30 to 200 mgKOH/g. If the acid value of the alkali-soluble resin (B) is less than 30mgKOH/g, it is difficult for the colored photosensitive resin composition to secure a sufficient developing speed. If it exceeds 200mgKOH/g, the adhesion to the substrate decreases, making it easy to cause a short circuit in the pattern and colorant. A problem occurs in compatibility with the colored photosensitive resin composition, the colorant in the colored photosensitive resin composition is precipitated or the storage stability of the colored photosensitive resin composition is lowered, and the viscosity is liable to increase.

Specific examples of the ethylenically unsaturated monomer (b1) having a carboxyl group include monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; Dicarboxylic acids such as fumaric acid, mesaconic acid, and itaconic acid; And anhydrides of these dicarboxylic acids; and mono (meth) acrylates of polymers having a carboxyl group and a hydroxyl group at both ends, such as ω-carboxypolycaprolactone mono (meth)acrylate, and acrylic acid and methacrylic acid are preferred.

As a method of giving an acid value by reacting an acid anhydride to the resin copolymer (b2) having a hydroxyl group, there is a method of giving an acid value by additionally reacting an anhydride to the hygrosyacrylate copolymer, but is not limited thereto. .

The hydroxyacrylates are typically as follows.

2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, N -Hydroxyethyl (meth)acrylates such as hydroxyethyl acrylamide;

The unsaturated monomers (b3) copolymerizable in the preparation of the alkali-soluble resin (B) are exemplified below, but are not limited thereto.

Specific examples of the copolymerizable unsaturated polymerization monomer (b3) include styrene, vinyltoluene, α-methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinyl Aromatic vinyl compounds such as benzyl methyl ether, m-vinyl benzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, and p-vinyl benzyl glycidyl ether;

N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, No-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, No-methylphenylmaleimide, Nm -N-substituted maleimide compounds such as methylphenylmaleimide, Np-methylphenylmaleimide, No-methoxyphenylmaleimide, Nm-methoxyphenylmaleimide, and Np-methoxyphenylmaleimide;

Methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, i-propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, alkyl (meth)acrylates such as sec-butyl (meth)acrylate and t-butyl (meth)acrylate; Cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6]decane-8-yl (meth)acrylate, 2- Alicyclic (meth)acrylates such as dicyclopentanyloxyethyl (meth)acrylate and isobornyl (meth)acrylate;

Aryl (meth)acrylates such as phenyl (meth)acrylate and benzyl (meth)acrylate;

3-(methacryloyloxymethyl)oxetane, 3-(methacryloyloxymethyl)-3-ethyloxetane, 3-(methacryloyloxymethyl)-2-trifluoromethyloxetane, 3-(methacryloyloxymethyl)-2-phenyloxetane, 2-(methacryloyloxymethyl)oxetane, 2-(methacryloyloxymethyl)-4-trifluoromethyloxetane, etc. And unsaturated oxetane compounds.

The monomers exemplified by the copolymerizable unsaturated monomers (b3) may be used alone or in combination of two or more.

The content of the alkali-soluble resin (B) is in the range of 10 to 80% by weight, preferably 10 to 70% by weight, based on the solid content in the photosensitive resin composition for green pixels. If the content of the alkali-soluble resin (B) is 10 to 80% by weight based on the above, it has sufficient solubility in a developer to facilitate pattern formation. Since the omission property becomes good, it is preferable.

Photopolymerization Compound (C)

The photopolymerizable compound (C) is a compound that can be polymerized by the action of the following photopolymerization initiator (D), and a monofunctional monomer, a bifunctional monomer, or a polyfunctional monomer may be used. Can be used.

Specific examples of the monofunctional monomer include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate or N-vinylpi Rolidone and the like, but are not limited thereto.

Specific examples of the bifunctional monomer include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate , Bis(acryloyloxyethyl) ether of bisphenol A or 3-methylpentanediol di(meth)acrylate, but are not limited thereto.

Specific examples of the polyfunctional monomer include trimethylol propane tri (meth) acrylate, ethoxylated trimethylol propane tri (meth) acrylate, propoxylated trimethylol propane tri (meth) acrylate, pentaerythritol tri (Meth)acrylate, pentaerythritol tetra (meth)acrylate, dipentaerythritol penta (meth)acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaerythritol hexa (meth) ) Acrylate or dipenta erythritol hexa (meth) acrylate, and the like, but are not limited thereto.

The photopolymerizable compound (C) is preferably contained in an amount of 5 to 45% by weight, and more preferably 7 to 45% by weight, based on the solid content in the colored photosensitive resin composition for green pixels. When the photopolymerizable compound (C) is contained in an amount of 5 to 45% by weight based on the above, it is preferable because the strength and smoothness of the pixel portion become good.

Light polymerization Initiator (D)

The photopolymerization initiator in the present invention is a compound that generates a radical capable of initiating polymerization of the photopolymerizable compound (C) by exposure to radiation such as visible light, ultraviolet rays, far ultraviolet rays, electron rays, and X-rays. Representative examples of such photoinitiators include acetophenone-based compounds, benzophenone-based compounds, biimidazole-based compounds, triazine-based compounds, oxime ester-based compounds, thioxanthone-based compounds, and the like. In the present invention, the photoinitiator may be used alone or in combination of two or more, and it is preferable to use one or more oxime ester compounds.

Specific examples of the acetophenone compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-1-[4-(2-hydroxy) Oxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexylphenylketone, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-Benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propane-1 -One, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one, and the like.

Examples of the benzophenone-based compound include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3',4,4'-tetra( tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, and the like.

Specific examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichloro Phenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole , 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole, 2,2-bis(2,6-dichlorophenyl)-4, And imidazole compounds in which the 4'5,5'-tetraphenyl-1,2'-biimidazole or the phenyl group at the 4,4',5,5' position is substituted with a carboalkoxy group. Among these, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4' ,5,5'-tetraphenylbiimidazole, 2,2-bis(2,6-dichlorophenyl)-4,4'5,5'-tetraphenyl-1,2'-biimidazole is preferably used do.

Specific examples of the triazine-based compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6 -(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis (Trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2- Yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine , 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl )-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

Examples of the oxime ester compound include 1,2-Octanedione, 1-[4-(phenylthio) phenyl]-,2-(O-benzoyloxime), 1-[9-Ethyl-6-(2-methylbenzoyl)-9H- carbazol-3-yl]ethanone 1-(O-acetyloxime).

Examples of the thioxanthone compound include 2-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichloro thioxanthone, 1-chloro-4-propoxy thioxanthone, etc. There is this.

In addition, the photopolymerization initiator (D) may further include a photopolymerization initiation aid (d1) in order to improve the sensitivity of the colored photosensitive resin composition of the present invention. When the colored photosensitive resin composition according to the present invention contains the photopolymerization initiation aid (d1), the sensitivity is further increased and the productivity can be improved.

The photopolymerization initiation aid (d1) may preferably be one or more compounds selected from the group consisting of an amine compound, a carboxylic acid compound, and an organic sulfur compound having a thiol group.

It is preferable to use an aromatic amine compound as the amine compound, and specifically, aliphatic amine compounds such as triethanolamine, methyl diethanolamine, and triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4- Isoamyl dimethylaminobenzoic acid, 2-ethylhexyl 4-dimethylaminobenzoic acid, 2-dimethylaminoethyl benzoic acid, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (common name: Michler's ketone ), 4,4'-bis(diethylamino)benzophenone, etc. can be used.

The carboxylic acid compound is preferably an aromatic heteroacetic acid, specifically phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid Acetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, and the like.

Specific examples of the organic sulfur compound having a thiol group include 2-mercaptobenzothiazole, 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(3-mercaptobutyloxyethyl)- 1,3,5-triazine-2,4,6(1H,3H,5H)-trione, trimethylolpropanetris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptobutyl) Rate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptopropionate), tetraethylene glycolbis (3-mercaptopropionate), etc. I can.

The photopolymerization initiator (D) is 0.1 to 40% by weight, preferably based on the total solid content of the colored photosensitive resin composition for green pixels of the present invention, based on the content of the alkali-soluble resin (B) and the photopolymerizable compound (C). It may be included in 1 to 30% by weight. If the photopolymerization initiator (D) is in the range of 0.1 to 40% by weight, it is preferable that the colored photosensitive resin composition for a green pixel of the present invention is highly sensitive to shorten exposure time, thereby improving productivity and maintaining high resolution. . Further, the strength of the pixel portion formed by using the composition under the above-described conditions and the smoothness on the surface of the pixel portion can be improved. In addition, the photopolymerization initiator (d1) should contain 10 to 100% by weight, preferably 20 to 100% by weight, of the total photopolymerization initiator (D). When the proportion of the photopolymerization initiator (d1) in the total photopolymerization initiator is less than 10% by weight, the reduction in sensitivity due to the dye cannot be overcome, and a short circuit of the pattern is likely to occur during the development process.

In addition, when the photopolymerization initiation aid (d1) is further used, the photopolymerization initiation aid (d1) is the alkali-soluble resin (B) and the light weight based on the total solid content of the colored photosensitive resin composition for green pixels of the present invention. It may be included in an amount of 0.1 to 40% by weight, preferably 1 to 30% by weight, based on the content of the synthetic compound (C). If the amount of the photopolymerization initiation aid (d1) is within the range of 0.1 to 40% by weight, The sensitivity of the colored photosensitive resin composition is further increased, and the productivity of the color filter formed by using the composition is improved.

Solvent (E)

The solvent (E) is for the green pixel of the present invention. As long as it is effective in dissolving other components contained in the colored photosensitive resin composition, the solvent used in the usual colored photosensitive resin composition can be used without particular limitation, and in particular, ethers, aromatic hydrocarbons, ketones, alcohols, esters or amino Drew et al. are preferred.

The solvent (E) is specifically ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether,

Diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether;

Ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate,

Alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, methoxypentyl acetate,

Aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene,

Ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone,

Alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin,

Esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate, and cyclic esters such as γ-butyrolactone.

The solvent (E) is preferably an organic solvent having a boiling point of 100°C to 200°C in terms of coating and drying properties, more preferably propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate , Butalactate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and the like can be used.

The exemplified solvent (E) may be used alone or in combination of two or more, and may be included in 60 to 90% by weight, preferably 70 to 85% by weight, based on the total weight of the colored photosensitive resin composition of the present invention. have. When the solvent (F) is in the range of 60 to 90% by weight described above, it is applied when applied with a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes referred to as a die coater), or inkjet. It provides the effect of improving the property.

Additive (F)

Additives such as fillers, other polymer compounds, curing agents, adhesion promoters, ultraviolet absorbers, anti-aggregation agents, etc., according to the needs of those skilled in the art, within the scope of not impairing the object of the present invention in addition to the above components, the photosensitive resin composition for green pixels of the present invention It is also possible to use together.

Specifically, the filler may be glass, silica, alumina, or the like, but is not limited thereto.

The other polymer compounds are specifically curable resins such as epoxy resin and maleimide resin, polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and thermoplastic resins such as polyurethane. However, it is not limited thereto.

The curing agent is used to increase deep curing and mechanical strength, and specifically, an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, an oxetane compound, etc. may be used, but the present invention is not limited thereto. Specifically, the epoxy compound is a bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, noblock epoxy resin, other aromatic epoxy resin, alicyclic epoxy resin, gly Cydyl ester resins, glycidylamine resins, or brominated derivatives of these epoxy resins, aliphatic, alicyclic or aromatic epoxy compounds other than epoxy resins and brominated derivatives thereof, butadiene (co)polymer epoxidation, isoprene (co) Polymer epoxides, glycidyl (meth) acrylate (co) polymers, triglycidyl isocyanurate, and the like may be used, but are not limited thereto. Specifically, the oxetane compound may be carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, cyclohexane dicarboxylic acid bisoxetane, etc., but are limited thereto. It is not.

The curing agent may be used in combination with a curing agent and a curing auxiliary compound capable of ring-opening polymerization of the epoxy group of the epoxy compound and the oxetane skeleton of the oxetane compound. Specifically, as the curing auxiliary compound, polyvalent carboxylic acids, polyvalent carboxylic anhydrides, acid generators, and the like can be used. The carboxylic anhydrides may be commercially available as an epoxy resin curing agent. Examples of the commercially available epoxy resin curing agent include a brand name (Adeka Hadona EH-700) (manufactured by Adeka Industries, Ltd.), a brand name (Rika Shiddo HH) (manufactured by Shin Nippon Ewha Corporation), and a brand name (MH-700) (Manufactured by New Japan Ewha Corporation) and the like.

The curing agent and the curing auxiliary compound exemplified above may be used alone or in combination of two or more.

Specifically, the adhesion promoter is vinyltrimethoxysilane, vinyltriethoxysilane, vinyl tris(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N -(2-Aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercapto propyltri Methoxysilane, 3-isocyanate propyl trimethoxy silane, and 3-isocyanate propyl triethoxy silane alone or a mixture thereof may be used. The adhesion promoter may be included in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 2 parts by weight, based on 100 parts by weight of the solid content of the composition.

Specifically, the ultraviolet absorber may be 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotyrazole, alkoxybenzophenone, or the like, but is not limited thereto.

The anti-aggregation agent may specifically use sodium polyacrylate, but is not limited thereto.

On the other hand, when a green pixel of a color filter was formed using a conventional colored photosensitive resin composition for a green pixel, the thickness of the pixel had to be formed to exceed 4 μm.

However, when a green pixel of a color filter is formed using the colored photosensitive resin composition for a green pixel of the present invention, the pixel has a film thickness of 1.5 um to 4.0 um, preferably 1.5 to 3.5 um, and more Preferably, a pattern may be formed with a film thickness of 2um to 3.0um. In addition, according to a preferred embodiment of the present invention, when a green pixel of a color filter is formed using the colored photosensitive resin composition for a green pixel, the chromaticity of the pixel is determined by the chromaticity coordinates (x, y) in the XYZ color system. As represented by, x of the chromaticity coordinates is 0.15<x<0.33, and y of the chromaticity coordinates is 0.63<y<0.80. Further, when a green pixel of a color filter is formed using the colored photosensitive resin composition for green pixels, the luminance Y of the pixel is 20<Y<40.

That is, the colored photosensitive resin composition for a green pixel of the present invention can produce a color filter capable of high color reproduction even with a thin thickness.

The method for preparing the colored photosensitive resin composition for a green pixel of the present invention will be described as follows.

First, the pigment (a1) of the colorant (A) is mixed with the solvent (F) and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. At this time, if necessary, a pigment dispersant (a3), part or all of the alkali-soluble resin (B), or a dye (a3) may be mixed together with a solvent (E) to dissolve or disperse.

The present invention by further adding dye (a3), the remainder of the alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), and a solvent (E) to a predetermined concentration to the mixed dispersion. It is possible to prepare a colored photosensitive resin composition according to.

The present invention provides a color filter including a color layer formed by forming the colored photosensitive resin composition for a green pixel of the present invention in a predetermined pattern, then exposing and developing.

According to a preferred embodiment of the present invention, when the chromaticity of the pixel of the color filter is represented by chromaticity coordinates (x, y) in the XYZ color system, x of the chromaticity coordinate is 0.15<x<0.33, and y may be 0.63<y<0.80. In addition, the luminance Y of the color filter pixel may be 20<Y<40. In addition, the pixel of the color filter may be patterned with a film thickness of 1.5 um to 4.0 um, preferably 1.5 to 3.5 um, and more preferably 2 um to 3.0 um.

In addition, it provides an image pickup device and a liquid crystal display device including the color filter of the present invention.

The color filter, the image pickup device, and the liquid crystal display of the present invention may be manufactured by a known method.

Another aspect of the present invention is a step of applying the colored photosensitive resin composition of the present invention; Selectively exposing a partial region of the colored photosensitive resin composition; And removing the exposed area or the non-exposed area of the colored photosensitive resin composition.

Hereinafter, the present invention will be described in more detail based on examples, but the embodiments of the present invention disclosed below are examples only, and the scope of the present invention is not limited to these embodiments. The scope of the present invention is indicated in the claims, and furthermore contains the meanings equivalent to the claims recorded and all modifications within the scope. In addition, "%" and "parts" indicating content in the following examples and comparative examples are based on weight unless otherwise noted.

Pigment dispersion composition manufacturing

<Pigment dispersion composition M1>

As a pigment, C.I. Pigment Blue 15:4 12.0 parts by weight, DISPERBYK-2001 (manufactured by BYK) 4.0 parts by weight as a pigment dispersant, 84 parts by weight of propylene glycol methyl ether acetate as a solvent were mixed/dispersed with a bead mill for 12 hours to obtain pigment dispersion M1. Was prepared.

<Pigment dispersion composition M2>

Pigment 12.0 parts by weight of a compound represented by the following formula (5), DISPERBYK-2001 (manufactured by BYK) 4.0 parts by weight as a pigment dispersant, and 84 parts by weight of propylene glycol methyl ether acetate as a solvent were mixed/dispersed by a bead mill for 12 hours to obtain a pigment. Dispersion M2 was prepared.

[Formula 5]

<Pigment dispersion composition M3>

As a pigment, C.I. Pigment Green 7 12.0 parts by weight, DISPERBYK-2001 (manufactured by BYK) 4.0 parts by weight as a pigment dispersant, 84 parts by weight of propylene glycol methyl ether acetate as a solvent were mixed/dispersed for 12 hours by a bead mill to prepare a pigment dispersion M3. .

<Pigment dispersion composition M4>

As a pigment, C.I. Pigment Yellow 138 12.0 parts by weight, DISPERBYK-2001 (manufactured by BYK) 4.0 parts by weight as a pigment dispersant, 84 parts by weight of propylene glycol methyl ether acetate as a solvent were mixed/dispersed with a bead mill for 12 hours to prepare a pigment dispersion M4. .

<Pigment dispersion composition M5>

12.0 parts by weight of CI Pigment Yellow 150 as a pigment, 4.0 parts by weight of DISPERBYK-2001 (manufactured by BYK) as a pigment dispersant, 84 parts by weight of propylene glycol methyl ether acetate as a solvent were mixed/dispersed for 12 hours by a bead mill, and pigment dispersion M5 Was prepared.

Synthesis of alkali-soluble resin

<Synthesis Example 1>

Propylene glycol monomethyl ether acetate 120 parts by weight, propylene glycol monomethyl ether 80 parts by weight, AIBN 2 parts by weight, acrylic acid 13.0 parts by weight, benzyl methacrylic in a flask equipped with a stirrer, thermometer reflux condenser, dropping lot and nitrogen inlet tube 10 parts by weight of rate, 57.0 parts by weight of styrene, 20 parts by weight of methyl methacrylate, and 3 parts by weight of n-dodecylmercapto were added, followed by nitrogen substitution. Then, while stirring, the temperature of the reaction solution was raised to 110° C. and reacted for 6 hours. The acid value of the solid content of the thus synthesized alkali-soluble resin was 100.2 mgKOH/g, and the weight average molecular weight Mw measured by GPC was about 15110.

Preparation of colored photosensitive resin composition

<Example 1>

16.90 parts of the <pigment dispersion composition M1>, 33.10 parts of the <pigment dispersion composition M2>, 9.56 parts of the resin of <Synthesis Example 1>, 3.18 parts of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.64 parts of Irgacure OXE01 (manufactured by BASF), A colored photosensitive resin composition was prepared by mixing 36.63 parts of propylene glycol monomethyl ether acetate.

<Example 2>

16.25 parts of the <pigment dispersion composition M1>, 31.25 parts of the <pigment dispersion composition M2>, 10.10 parts of the resin of <Synthesis Example 1>, 3.36 parts of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.67 parts of Irgacure OXE01 (manufactured by BASF), A colored photosensitive resin composition was prepared by mixing 38.36 parts of propylene glycol monomethyl ether acetate.

<Example 3>

12.25 parts of the <pigment dispersion composition M1>, 24.00 parts of the <pigment dispersion composition M2>, 12.56 parts of the resin of <Synthesis Example 1>, 4.18 parts of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.84 parts of Irgacure OXE01 (manufactured by BASF), A colored photosensitive resin composition was prepared by mixing 46.17 parts of propylene glycol monomethyl ether acetate.

<Example 4>

The <pigment dispersion composition M1> 17.35 parts, <pigment dispersion composition M2> 28.90 parts, resin of <Synthesis Example 1> 10.37 parts, KAYARAD DPHA (manufactured by Nippon Kayaku) 3.45 parts, Irgacure OXE01 (manufactured by BASF) 0.69 parts, A colored photosensitive resin composition was prepared by mixing 39.23 parts of propylene glycol monomethyl ether acetate.

<Example 5>

12.19 parts of the <pigment dispersion composition M1>, 20.31 parts of the <pigment dispersion composition M2>, 13.38 parts of the resin of <Synthesis Example 1>, 4.45 parts of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.89 parts of Irgacure OXE01 (manufactured by BASF), A colored photosensitive resin composition was prepared by mixing 48.78 parts of propylene glycol monomethyl ether acetate.

<Example 6>

7.85 parts of the <pigment dispersion composition M1>, 42.15 parts of the <pigment dispersion composition M2>, 9.56 parts of the resin of <Synthesis Example 1>, 3.18 parts of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.64 parts of Irgacure OXE01 (manufactured by BASF), A colored photosensitive resin composition was prepared by mixing 36.63 parts of propylene glycol monomethyl ether acetate.

<Comparative Example 1>

11.43 parts of the <pigment dispersion composition M1>, 72.64 parts of the <pigment dispersion composition M4>, 2.11 parts of the resin of <Synthesis Example 1>, 0.70 parts of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.14 parts of Irgacure OXE01 (manufactured by BASF), A colored photosensitive resin composition was prepared by mixing 12.97 parts of propylene glycol monomethyl ether acetate.

<Comparative Example 2>

14.64 parts of the <pigment dispersion composition M1>, 35.36 parts of the <pigment dispersion composition M5>, 9.56 parts of the resin of <Synthesis Example 1>, 3.18 parts of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.64 parts of Irgacure OXE01 (manufactured by BASF), A colored photosensitive resin composition was prepared by mixing 36.63 parts of propylene glycol monomethyl ether acetate.

<Comparative Example 3>

54.61 parts of the <pigment dispersion composition M3>, 12.18 parts of the <pigment dispersion composition M5>, 5.89 parts of the resin of <Synthesis Example 1>, 1.96 parts of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.39 parts of Irgacure OXE01 (manufactured by BASF), A colored photosensitive resin composition was prepared by mixing 24.97 parts of propylene glycol monomethyl ether acetate.

<Comparative Example 4>

50.02 parts of the <pigment dispersion composition M3>, 27.48 parts of the <pigment dispersion composition M4>, 3.55 parts of the resin of <Synthesis Example 1>, 1.18 parts of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.24 parts of Irgacure OXE01 (manufactured by BASF), A colored photosensitive resin composition was prepared by mixing 17.53 parts of propylene glycol monomethyl ether acetate.

Experimental production example 1: Preparation of color filter

A color filter was manufactured using the colored photosensitive resin compositions prepared in Examples 1 to 6 and Comparative Examples 1 to 4.

Specifically, each of the above colored photosensitive resin compositions is coated on a 2-inch-angled glass substrate (manufactured by Corning, 「EAGLE XG」) by spin coating, and then placed on a heating plate and held at a temperature of 100° C. for 3 minutes to form a thin film. Made it. Subsequently, a test photomask having a pattern for changing the transmittance in a stepwise shape in the range of 1 to 100% and a line/space pattern of 1 µm to 100 µm is placed on the thin film, and the distance between the test photo mask is set to 300 µm. Was investigated. At this time, the ultraviolet light source was irradiated with an illuminance of 60 mJ/cm 2 using a 1KW high-pressure mercury lamp containing all g, h, and i lines, and no special optical filter was used. The UV-irradiated thin film was developed by immersing it in a developing solution of a KOH solution having a pH of 10.5 for 2 minutes. The glass plate coated with the thin film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 200° C. for 25 minutes to prepare a color filter.

Experimental example One

The color filter prepared in Experimental Preparation Example 1 was evaluated in the following manner.

(1) Evaluation of development speed

In the above process, the time taken for the unexposed part to completely dissolve in the developer during development (development speed) was measured and shown in Table 1.

(2) Evaluation of adhesion

When the generated pattern was evaluated through an optical microscope, the degree of tearing on the pattern as follows was evaluated and shown in Table 1 below.

<Evaluation criteria>

○: No tearing in the pattern

△: 1 to 3 tears in the pattern

×: 4 or more tearing in pattern

××: 10 or more tears in the pattern

×××: No pattern formation

(3) residue evaluation

After development, the presence or absence and amount of residuals that were not washed away on the area to be developed were observed. When there was no residue, it was evaluated as good and if there was a residue, it was evaluated as bad.

Composition Development speed (sec) Residue Adhesion Example 1 10 Good ○ Example 2 11 Good ○ Example 3 10 Good ○ Example 4 12 Good ○ Example 5 11 Good ○ Example 6 10 Good ○ Comparative Example 1 32 Bad XXX Comparative Example 2 28 Bad X Comparative Example 3 35 Bad △ Comparative Example 4 45 Bad XXX

Experimental production example 2: Preparation of color filter

A color filter was prepared in the same manner as in Experimental Preparation Example 1 except that the test photomask was not used.

Experimental example 2

The color filter prepared in Experimental Preparation Example 2 was evaluated in the following manner.

(1) chromaticity

The prepared color filter was measured using a colorimeter (Olympus, OSP-200), and is shown in Table 2.

(2) film thickness

The prepared color filter was measured using a Surface Profile measuring device (manufactured by Veeco, DEKTAK 6M), and is shown in Table 2.

Composition Film thickness(um) Pigment content (%) x y Y Example 1 2.2 40% 0.1610 0.6408 25.59 Example 2 2.4 38% 0.1963 0.6960 26.81 Example 3 3.2 29% 0.1981 0.6957 27.14 Example 4 2.4 37% 0.1888 0.6836 25.72 Example 5 3.4 26% 0.1888 0.6836 25.72 Example 6 3.2 40% 0.2003 0.7214 29.52 Comparative Example 1 3.4 67.3% 0.1610 0.6408 23.83 Comparative Example 2 3.2 40% 0.1610 0.6408 21.20 Comparative Example 3 3.2 53.4% 0.1610 0.6408 23.24 Comparative Example 4 3.2 64.5% 0.1610 0.6408 25.22

As shown in Tables 1 and 2, when implementing the same color in Example 1 compared to Comparative Examples 1 to 4, the pigment content was low. Therefore, it can be seen that Example 1 has better coloring power than Comparative Examples 1 to 4.

Examples 3 and 6 are excellent in color even though the pigment content is low even at the same thickness than Comparative Examples 2 to 4. Example 5 is also excellent in color even though the pigment content is low even at the same thickness as in Comparative Example 1.

Further, it can be seen that the transmittance is also excellent by measuring the colorimeter and evaluating the luminance.

In conclusion, the present invention is capable of forming a thin film with a thickness of 2.2 μm, and has excellent coloring power for achieving high color reproduction. In addition, it has excellent transmittance, and it is possible to form a green pixel without residue and pattern tearing.

Claims (15)

Including a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D) and a solvent (E),
The colorant (A) is
A yellow pigment comprising a compound represented by the following Formula 1 and a blue pigment including at least one selected from CI pigment blue 15:6, CI pigment 15:3, and CI pigment 15:4,
A colored photosensitive resin composition for green pixels, characterized in that it does not contain CI pigment green 7, 36 and 58:
[Formula 1]

In Formula 1, R1 to R9 are each independently a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO ₃ H, -COOH,- SO ₃ M, -COOM, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent,
R10 to R13 are each independently a hydrogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO ₃ H, -COOH, -SO ₃ M, -COOM, Represents a phthalimidomethyl group which may have a substituent or a sulfamoyl group which may have a substituent,
M is a monovalent to trivalent metal or alkyl ammonium,
Adjacent groups of R1 to R4 may be integrated to form an aromatic ring which may have a substituent, and R10 to R13 may be integrated with adjacent groups to form an aromatic ring which may have a substituent. The method according to claim 1,
The compound represented by Formula 1 is
A colored photosensitive resin composition for a green pixel, characterized in that it is any one selected from compounds represented by the following Chemical Formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

R14 to R19, R24 to R28 of Formula 2, R29 to R32, R39 to R43 of Formula 3, R44 to R49 and R56 to R60 of Formula 4 are each independently a hydrogen atom, a halogen atom, an alkyl group which may have a substituent , Alkoxyl group which may have a substituent, aryl group which may have a substituent, -SO ₃ H, -COOH, -SO ₃ M, -COOM, a phthalimidomethyl group which may have a substituent, or a sulfamo which may have a substituent Show the diary,
R20 to R23 in Formula 2, R33 to R38 in Formula 3, and R50 to R55 in Formula 4 are each independently a hydrogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and an aryl which may have a substituent. Group, -SO ₃ H, -COOH, -SO ₃ M, -COOM, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent,
M is a monovalent to trivalent metal or alkyl ammonium. The method according to claim 1,
The yellow pigment is CI Pigment Yellow 13, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 129, 137, 138, 139, 147, 148, 150, 153, A colored photosensitive resin composition for a green pixel, further comprising at least one selected from the group consisting of 154, 166, 173, 180, and 185. The method according to claim 1,
The blue pigment is CI Pigment Blue 15:4, characterized in that the colored photosensitive resin composition for a green pixel. The method according to claim 1,
The colorant (A) is a colored photosensitive resin composition for a green pixel, characterized in that it is contained in a weight fraction of 5 to 60% by weight based on the total weight of the solid content in the colored photosensitive resin composition for green pixels. The method according to claim 1,
The blue pigment is a colored photosensitive resin composition for a green pixel, characterized in that it is contained in a weight fraction of 5 to 50% by weight based on the total weight of the solid content in the colorant (A). The method according to claim 1,
When a green pixel of a color filter is formed using the colored photosensitive resin composition for a green pixel, the chromaticity of the pixel is represented by chromaticity coordinates (x, y) in the XYZ color system,
X of the chromaticity coordinate is 0.15<x<0.33,
The colored photosensitive resin composition for a green pixel, wherein y of the chromaticity coordinate is 0.63<y<0.80. The method according to claim 1,
When forming green pixels of a color filter using the colored photosensitive resin composition for green pixels,
The luminance Y of the pixel is 20<Y<40, wherein the colored photosensitive resin composition for a green pixel. The method according to claim 1,
When a green pixel of a color filter is formed using the colored photosensitive resin composition for a green pixel, the pixel is patterned with a film thickness of 1.5um to 4.0um. A color filter formed by forming the colored photosensitive resin composition for a green pixel of claim 1 in a predetermined pattern, then exposing and developing. The method of claim 10,
When the chromaticity of the pixel of the color filter is represented by chromaticity coordinates (x, y) in the XYZ color system,
X of the chromaticity coordinate is 0.15<x<0.33,
The color filter, wherein y of the chromaticity coordinate is 0.63<y<0.80. The method of claim 10,
A color filter that satisfies Equation 3 below, wherein the luminance Y of the color filter pixel is 20<Y<40. The method of claim 10,
The color filter, characterized in that the pixel of the color filter is patterned with a film thickness of 1.5um ~ 4.0um. An image pickup device comprising the color filter of claim 10. A liquid crystal display device comprising the color filter of claim 10.