JPH09118836A - Mixed green pigment for sublimation transfer, color filter and its production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject pigment useful for a color filter for liquid crystal display element and a color-separation color filter for image pickup element. SOLUTION: The objective pigment is produced by compounding (A) 1 pt.wt. of an azamethine compound of the formula [R1 is an alkyl or trifluoromethyl; R2 and R3 are each an alkyl; X is H or OR4 (R4 is an alkyl)] with (B) preferably 0.2-4 pts.wt. of a water-insoluble sublimable yellow pigment selected from quinoline dye, styryl dye, and azo dye. The component B has a sublimation starting temperature of 170-260 deg.C and is preferably a pyridone-based azo dye, etc.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a color filter used in a liquid crystal display device and a green mixed dye for sublimation transfer color filter useful as a color separation color filter used in an image pickup device, and a method for producing a color filter using the same.

[0002]

2. Description of the Related Art Conventionally, in order to color a liquid crystal display device or a solid-state image pickup device, red, green and blue (R, G, B) or yellow, magenta and cyan (Y, M, C) are used. A method of combining primary color filters has been adopted. Although there are several methods for forming these color filters, the most basic method is the so-called dyeing method. According to this method, a transparent dyeable resin is formed in a mosaic shape on a substrate, then immersed in a dyeing bath for dyeing, washed with water, and then fixed to perform a dye-proof film to form one color. By repeating this three times, a color filter having a fine color pattern of three primary colors is formed.

[0003]

The dyeing method has a feature that an extremely fine color pattern can be freely formed. However, the photolithography step, the dyeing step, the washing / cleaning step can be performed as many times as the number of colors to be dyed. Since many manufacturing processes such as a fixing process and a dye-proofing process are complicated, there is a risk that the yield may be reduced due to dust adhesion during manufacturing. Further, since the coloring density is almost proportional to the film thickness of the dyed resin film, the fluctuation of the film thickness causes unevenness of color and deteriorates the quality of the product. Depending on the order of dyeing, color unevenness may occur due to contamination or desorption of other colors. Further, a liquid crystal display element manufacturer has strongly demanded a method of reducing the number of steps for manufacturing a color filter to improve the yield and make the cost lower.

[0004]

Means for Solving the Problems As a result of various studies for solving the above problems, the present inventors have found that a green color obtained by mixing an azamethine compound represented by the following general formula [I] and a yellow dye The mixed dye has good sublimation transfer suitability,
This green mixed dye is used in a sublimation transfer method to produce green, R, G, and B, which have excellent heat resistance and excellent spectral characteristics and light resistance.
The present invention has been completed by discovering that primary color filters can be manufactured. That is, the present invention provides the formula (1) [I]

[0005]

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[In the formula [I], R ₁ is an alkyl group or a trifluoromethyl group, R ₂ and R ₃ are each an alkyl group, and X is a hydrogen atom or —OR ₄ (wherein R ₄ is an alkyl group. Represents.) Represents. ] A green mixed dye for sublimation transfer comprising an azamethine compound and a yellow dye, (2)
R ₁ is a linear or branched alkyl group having 1 to 4 carbon atoms, R ₂ and R ₃ are linear alkyl groups having 1 to 4 carbon atoms, and R ₄ is a methyl group or an ethyl group ( (1) Green mixed dye for sublimation transfer, (3) R ₁ is a methyl group, R ₂ and R ₃
Is a methyl group or an ethyl group, X is a hydrogen atom, and (1) or (2) a green mixed dye for sublimation transfer, (4) a yellow dye is selected from quinoline dyes, styryl dyes or azo dyes, and (1) to (3) green mixed dye for sublimation transfer, which is an insoluble and sublimable dye.
(4) A green mixed dye for sublimation transfer, wherein the azo dye is a pyrazole azo dye or a pyridone azo dye, and (6) a yellow dye is a water-insoluble and sublimable pyridone azo dye (1) to (4) Sublimation transfer green mixed dye and (7) yellow dye have a sublimation start temperature of 170 to 260 ° C.
(1) to (6), which is a green mixed dye for sublimation transfer,
(8) The green mixed dye for sublimation transfer of (1) to (7), wherein the mixing ratio of the azamethine compound and the yellow dye is 0.2 to 4 parts by weight of the yellow dye to 1 part by weight of the azamethine compound,

(9) A color filter having the green mixed dye for sublimation transfer of (1) to (8), (10) a dye receiving layer of a transparent substrate having a dye receiving layer on the surface, and (1) to (8) (1) A method for producing a color filter, which comprises heating the sheet after facing the dye-containing layer surfaces of the sheet having the green mixed dye-containing layer for sublimation transfer of (1).
1) The dye receiving layer is a cured film of a photocurable resin composition containing a resin having an acid value of 80 mgKOH / g or more (1
0) The method for producing a color filter, (12) The resin having an acid value of 80 or more is a resin containing a carboxylic acid group and a carboxylic acid ester group or a polymer of (meth) acrylic acid (ester) (11). (13) A method of producing a color filter, wherein the resin containing a carboxylic acid group and a carboxylic acid ester group is a copolymer composed of maleic anhydride and one or more kinds of monomers copolymerizable with maleic anhydride. The maleic anhydride part of the copolymer is represented by the following formula (1) HO (C ₂ H ₄ O) n -A (1) [wherein A represents an acryloyl or methacryloyl group, and n represents 1 or 2]. A compound represented by], and the following formula _{(2) HO (C 2 H} 4 O) n -R (2) wherein R represents an alkyl group, an alkylphenyl group, Arukaroiru group or (meth) acryloyl group, n represents an integer of 2 or more. ] The manufacturing method of the color filter of (12) which is the unsaturated group containing polycarboxylic acid resin half-esterified with the compound represented by these,

(14) The method for producing a color filter according to (13), wherein the monomer copolymerizable with maleic anhydride is styrene, α-methylstyrene, isobutylene, (meth) acrylic acid alkyl ester or benzyl (meth) acrylate. (15) The method for producing a color filter according to (13) or (14), wherein the weight average molecular weight of the copolymer of maleic anhydride and one or more kinds of monomers copolymerizable with maleic anhydride is 5000 or more, (16) The reaction rate of half-esterification is 50 to 100% (13)
To (15) the method for manufacturing a color filter, (17)
The method for producing a color filter according to (12), wherein the (meth) acrylic acid (ester) polymer is a methyl methacrylate, benzyl methacrylate, or methacrylic acid polymer.
8) The method for producing a color filter according to (11), wherein the photocurable resin composition is a composition containing an epoxy compound.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The mixing ratio of the azamethine compound and the yellow dye in the green mixed dye of the present invention is preferably 0.2 to 4 parts by weight, more preferably 0.5 to 4 parts by weight with respect to 1 part by weight of the azamethine compound. 2 parts by weight, more preferably about 0.65 to 1.5 parts by weight. Further, one or more azamethine compounds and one or more yellow dyes can be used. In the present invention, sublimation means not only vaporization from a solid state but also vaporization from a molten state.

R ₁ in the above general formula [I] represents an alkyl group or a trifluoromethyl group. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, i-propyl group, n- Butyl group, i-butyl group, sec-butyl group, t-
A linear or branched alkyl group having 1 to 4 carbon atoms such as a butyl group is preferable, and a methyl group is more preferable.
As the alkyl group represented by R ₂ and R ₃ , linear alkyl groups having 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, and n-butyl groups are preferable, and methyl group and ethyl group are more preferable. X is ₄ hydrogen atom or -OR. Examples of R ₄ include alkyl groups such as methyl and ethyl groups. Examples of preferable X include a hydrogen atom.

Among the azamethine compounds represented by the general formula [I], two compounds in which R ₁ is a methyl group, R ₂ and R ₃ are ethyl groups and propyl groups, and X is a hydrogen atom are described in J. C
HEM. SOC. PERKIN TRANS. II 1
987 p815-818 describes its method of synthesis and visible absorption spectrum. However, no description can be found that the azamethine compound represented by the general formula [I] containing these two compounds can be mixed with a yellow dye to form a green mixed dye for a color filter useful for sublimation transfer.

The azamethine compound represented by the general formula [I] is produced according to the method described in the above literature. That is, the formula [II]

[0013]

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3-dicyanovinylindane represented by
1-one and the general formula [III]

[0015]

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[In the formula [III], R ₁ , R ₂ , R ₃ and X have the same meanings as described above. ] The 4-nitrosoaniline compound represented by
After reacting for ~ 5 hours, it is filtered and washed with alcohol to obtain a crude dye. Then, it is recrystallized from a recrystallization solvent such as toluene to obtain a purified product. Specific examples of the 4-nitrosoaniline compound include N, N-diethyl-3-acetylamino-4-nitrosoaniline, N, N-dimethyl-3-acetylamino-4-nitrosoaniline, N, N.
-Dipropyl-3-acetylamino-4-nitrosoaniline, N, N-dibutyl-3-acetylamino-4-nitrosoaniline, N, N-dimethyl-3-propionylamino-4-nitrosoaniline, N, N-diethyl -3
-Propionylamino-4-nitrosoaniline, N, N
-Diethyl-3-butyrylamino-4-nitrosoaniline, N, N-diethyl-3-valeroylamino-4-nitrosoaniline, N, N-diethyl-3-trifluoroacetylamino-4-nitrosoaniline, N, N -Dipropyl-3-trifluoroacetylamino-4-nitrosoaniline, N, N-diethyl-3-acetylamino-4-
Nitroso-6-methoxyaniline, N, N-diethyl-
3-Acetylamino-4-nitroso-6-ethoxyaniline and the like can be mentioned.

Typical examples of the azamethine compound represented by the general formula [I] obtained by the above method are shown below.

[0018]

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The visible absorption spectrum of the azamethine compound represented by the general formula [I] is about λmax = 670-690 nm.
And has the optimum absorption for producing a green color tone when mixed with a yellow pigment. Moreover, the thermal properties thereof are far higher than those of other cyan dyes such as phthalocyanine dyes or anthraquinone-based turkis dyes, and they are excellent in sublimation transferability. As an example thereof, a thermogravimetry (TG) chart of dye [IV] is shown in FIG. From this figure, point A is the sublimation start point, and a decrease of 1.0% was recognized 19 minutes after the start of the test, and the temperature at that time was 209.0.
C., and point B is 1 at 26.80 minutes after the start of the test.
A 0.0% weight loss was observed and the temperature at that time was 293.3.
° C. Therefore, the dye [IV] is
It can be said that the sublimation start temperature is 209 ° C, the sublimation property is high, and the sublimation transfer property is excellent.

Any yellow dye may be mixed to obtain a green color tone, but a yellow dye which is water-insoluble and has sublimability is preferable. As a measure of sublimability, for example, the sublimation start temperature is preferably 170 to 260 ° C. As such a pigment, a pigment having no group having a high affinity for water such as a sulfonic acid group or a carboxylic acid group is preferable, and for example, a quinoline dye,
Examples include styryl dyes and azo dyes. Examples of the quinoline dye include compounds of the following formula (i), and examples of styryl dyes include compounds of the following formula (ii). As the azo dye, focusing on the coupling component, for example, a pyrazole-based azo dye (for example, a compound of the following formula (iii)), an aniline-based azo dye (for example, a compound of the following formula (iv) or a formula (v)), a pyridone-based azo dye Specific examples thereof include monoazo dyes such as azo dyes (for example, compounds of the following formula (vi)), and pyridone monoazo dyes and pyrazole monoazo dyes are preferable from the viewpoint of sublimability and hue. The hydroxyl group may be present as long as it does not significantly affect the sublimation property.

[0021]

[Chemical 6]

The transparent substrate having a dye receiving layer used in the present invention is not particularly limited as long as it is a flat substrate, and examples thereof include a plate-shaped one and a film (sheet) -shaped one.
Examples of the material include glass and plastics such as polyester and polycarbonate.

The dye receiving layer used in the present invention is preferably a cured film of a photocurable resin composition containing a resin having an acid value of 80 or more. The acid value of the resin contained as an essential component in the photocurable resin composition is 80 or more, preferably about 80 to 250, more preferably about 90 to 200, further preferably about 95 to 180, and further preferably 98 to About 170 is good. As the resin having an acid value of 80 or more, for example, a resin containing a carboxylic acid group and a carboxylic acid ester group or (meth) acrylic acid (ester)
Polymers of These may be used in combination. Examples of the resin containing a carboxylic acid group and a carboxylic acid ester group include an unsaturated group-containing polycarboxylic acid resin, and examples of the polymer of (meth) acrylic acid (ester) include (meth) acrylic acid and methyl. Monomers such as (meth) acrylic acid and esters such as (meth) acrylate, ethyl (meth) acrylate, benzyl (meth) acrylate, hydroxyalkyl (meth) acrylates such as hydroxyethyl (meth) acrylate, and alkylacrylamides Examples thereof include those obtained by polymerizing two or more kinds or one or more kinds thereof and a polymerizable monomer such as vinylpyrrolidone and styrene by a known method.

The unsaturated group-containing polycarboxylic acid resin, which is a resin containing a carboxylic acid group and a carboxylic acid ester group, is an easily developable and photocurable resin having a property of being dissolved in an alkaline developer, and maleic anhydride. And, after polymerizing using a radical generator at a ratio to be described later, one or more kinds of monomers copolymerizable with maleic anhydride, the compound represented by the formula (1) or (2) is added with a basic catalyst. It is obtained by carrying out an addition reaction with.

As the monomer to be copolymerized with maleic anhydride, any monomer may be used as long as it is a copolymerizable monomer, and various kinds may be used in combination. Particularly useful monomers include, for example, styrene, α-methylstyrene, isobutylene,
Examples thereof include (meth) acrylic acid alkyl ester and benzyl (meth) acrylate. Maleic anhydride,
The ratio of the monomers to be copolymerized with this is such that the total amount of the monomers to be copolymerized is 1 to 5 mol per 1 mol of maleic anhydride.
A mol ratio of 1 to 3 mol is more preferable. Maleic anhydride and a monomer to be copolymerized therewith are dissolved in an organic solvent that does not inhibit polymerization, such as acetic acid ester, dioxane, and xylene, and a radical generator such as azobisisobutyronitrile, benzoyl peroxide, and lauroyl peroxide. To 0.1% of the total weight of maleic anhydride and the monomers to be copolymerized therewith.
The copolymer is obtained by adding 5 wt%, more preferably 0.5 to 2 wt%, and reacting in the temperature range of 70 ° C to 100 ° C for 5 to 10 hours. The copolymer thus obtained is isolated and dried by a known method,
It is used for half-esterification in the next step.

The above copolymer is dissolved in an organic solvent such as ethyl cellosolve acetate or butyl cellosolve acetate which does not inhibit the half-esterification reaction, and then a basic catalyst such as pyridine, triethylamine or 2-methylimidazole is used as the copolymer. It is added within the range of 0.05 to 1% by weight, and more preferably 0.1 to 0.6% by weight. Next, the compound represented by the above formula (2) is added to the above reaction solution within the range of 5 to 60 mol%, more preferably 10 to 50 mol%, based on the number of moles of maleic anhydride in the copolymer. In addition, heat to 95 ~ 100 ℃, 1 at the same temperature
Allow to react for ~ 5 hours. Examples of the alkyl group in the formula (2) include C _{1 to} C ₅ alkyl groups such as methyl group, ethyl group, propyl group, butyl group and pentyl group, and examples of the alkylphenyl group include methylphenyl group and ethylphenyl group. Group, a phenyl group having a C _{1 to} C ₅ alkyl group such as a propylphenyl group, a butylphenyl group, and a pentylphenyl group, and an alkaroyl group includes, for example, C ₂ such as an acetyl group, a propionyl group, a butyryl group, and a valeryl group. To C ₅ alkaloyl group, and R in the formula (2) includes acryloyl group, methacryloyl group and the like. Specific examples of the compound represented by the formula (2) include polyethylene glycol monomethacrylate, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene monoalkylate and the like. In the present invention, for the purpose of adjusting the developability and the physical properties of the film after photocuring, which will be described later, a part of the compound represented by the formula (2) may be replaced with other alcohol to be half-esterified. Specific examples thereof include alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, and 2-ethylhexanol, and the reaction is carried out by simultaneously adding and reacting with the compound represented by the formula (2).
It is added in the range of 50 mol% or less with respect to the number of moles of the compound represented by the formula (2).

After completion of the reaction, the compound represented by the formula (1) is added in the same number of moles as that of the remaining maleic anhydride moiety obtained by reacting the compound represented by the formula (2). 1
By heating to 00 ° C. and reacting at the same temperature for 1 to 5 hours, an easily developable unsaturated group-containing polycarboxylic acid resin to be a sublimable dye receiving layer used in the present invention can be obtained. Specific examples of the compound represented by the formula (1) include hydroxyethyl (meth) acrylate, diethylene glycol mono (meth) acrylate and the like, and they may be used alone within the above range of the number of moles or 2 You may use together more than one kind.

The reaction rate of half-esterification of the unsaturated group-containing polycarboxylic acid resin having an acid value of 80 or more obtained by the above method (actual acid value / theoretical acid value × 100) is
For example, from the viewpoint of development residue and resolution after patterning in the manufacturing process of a color filter, about 50 to 100
%, Preferably about 60-100%, more preferably about 7
It is preferably 0 to 100%, more preferably about 75 to 100%.

The photocurable resin composition used in the present invention contains various additives such as a photopolymerization initiator in addition to the above resin having an acid value of 80 or more. For example, when the above-mentioned easily developable unsaturated group-containing polycarboxylic acid resin is used as a resin having an acid value of 80 or more, a photopolymerization initiator and, if necessary, a photocrosslinking agent, a photopolymerizable cured film are modified. Each component such as a mass agent and a thermosetting agent is blended.

Examples of the photopolymerization initiator include dibenzyl; benzoin ether; benzoin isobutyl ether; benzoin isopropyl ether; benzophenone; benzoylbenzoic acid; methyl benzoylbenzoate.
4-benzoyl-4'-methyldiphenyl sulfide; benzyl methyl ketal; 2-n-butoxyethyl-4-dimethylaminobenzoate; 2-chlorothioxanthone; 2,4-diethylthioxanthone; 2,4-
Diisopropylthioxanthone; Dimethylaminomethylbenzoate; Isoamyl p-dimethylaminobenzoate; 3,3'-Dimethyl-4-methoxybenzophenone;2,4-Dimethylthioxanthone; 1- (4-dodecylphenyl) -2-hydroxy-2- Methylpropan-1-one; 1-hydroxycyclohexyl phenyl ketone; 2-hydroxy-2-methyl-1-phenylpropan-1-one; 1- (4-isopropylphenyl)-
2-Hydroxy-2-methylpropan-1-one; isopropylthioxanthone; methylobenzoyl formate; 2-methyl-1- [4- (methylthio) phenyl]
2-morpholinopropan-1-one and the like can be mentioned. These photopolymerization initiators can be used alone or in combination of two or more, and are 0.5 to 10% by weight, preferably 0.5 to 5% by weight, based on the total weight of the photopolymerizable compound.
Is added within the range.

The photo-crosslinking agent is a monomer, oligomer, prepolymer or the like which can be crosslinked or polymerized by light. Examples of such monomers, oligomers and prepolymers include ethyl acrylate, hydroxyethyl methacrylate, ethylene glycol dimethacrylate,
Acrylic acid or methacrylic acid esters of monohydric or polyhydric alcohols such as pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, isocyanuric acid ethylene oxide modified triacrylate; polyhydric alcohols Polyester (meth) acrylate obtained by reacting a (meth) acrylic acid with a polyester prepolymer obtained by condensing a monobasic acid or a polybasic acid with a compound having a polyol group and two isocyanate groups Polyurethane (meth) acrylate obtained by subsequent reaction with (meth) acrylic acid; bisphenol A type epoxy resin, bisphenol F type epoxy resin, novolac type epoxy resin, polycarb Obtained by reacting (meth) acrylic acid with an epoxy resin such as acid glycidyl ester, polyol polyglycidyl ester, aliphatic or alicyclic epoxy resin, amine epoxy resin, triphenolmethane type epoxy resin, dihydroxybenzene type epoxy resin Usable photopolymerizable resins such as epoxy (meth) acrylate are mentioned.

Examples of the photopolymerizable cured film modifier include unsaturated group-containing polycarboxylic acid resins other than the easily developable unsaturated group-containing polycarboxylic acid resins described above, such as bisphenol A type epoxy resin and bisphenol. Epoxy groups such as F type epoxy resin, novolac type epoxy resin, polycarboxylic acid glycidyl ester, polyol polyglycidyl ester, aliphatic or alicyclic epoxy resin, amine epoxy resin, triphenol methane type epoxy resin, dihydroxybenzene type epoxy resin And (meta)
Epoxy (meth) acrylate-carboxylic acid adduct obtained by reacting an acid anhydride with a hydroxy group obtained by reacting acrylic acid; ethylene, propene, isobutylene, styrene, vinylphenol, acrylic copolymerizable with maleic anhydride Half-esterification by reacting the maleic anhydride part of the copolymer with acid, acrylic acid ester, acrylamide, etc. monomer with acrylate having alcoholic hydroxy group such as hydroxyethyl acrylate or acrylate having epoxy group such as glycidyl methacrylate. Examples of the compound include: acrylic acid, a compound obtained by further reacting acrylic acid with the -OH group of a copolymer of an acrylic acid ester and an acrylate copolymer having an alcoholic hydroxy group such as hydroxyethyl acrylate.

The above-mentioned photopolymerizable compounds are used alone or as a mixture, and the total amount thereof is 50 to 150 when the weight of the easily developable unsaturated group-containing polycarboxylic acid resin is 100 parts. Parts, more preferably 80-120
Used in a range of parts.

The thermosetting agent is a compound which can be crosslinked or polymerized by heat, and examples thereof include epoxy compounds. The epoxy compound improves the heat resistance by thermally reacting with the easily developable unsaturated group-containing polycarboxylic acid resin or the like and crosslinking. As a concrete epoxy compound,
Bisphenol A type epoxy resin, bisphenol F type epoxy resin, novolac type epoxy resin, polycarboxylic acid glycidyl ester, polyol polyglycidyl ester, aliphatic or alicyclic epoxy resin, amine epoxy resin, triphenolmethane type epoxy resin, dihydroxybenzene Type epoxy resin and the like. Such epoxy compounds are used alone or as a mixture, and the total amount thereof is 5 to 30 parts, and more preferably, when the weight of the easily developable unsaturated group-containing polycarboxylic acid resin is 100 parts. , 10 to 20 parts.

As a resin having an acid value of 80 or more,
For example, when the above-mentioned (meth) acrylic acid (ester) polymer is used, since this polymer is not photocurable, a polyfunctional resin and a photocrosslinking agent are required in addition to the photopolymerization initiator. Furthermore, if necessary, components such as a photopolymerizable cured film modifier and a thermosetting agent are blended. As a polyfunctional resin,
For example, the above-mentioned unsaturated group-containing polycarboxylic acid resin may be mentioned. Examples of the photopolymerization initiator, the photocrosslinking agent, the photopolymerizable cured film modifier, the thermosetting agent and the like include those mentioned above.

The photocurable resin composition used in the dye receiving layer of the transparent substrate used in the present invention can be obtained by mixing the above-mentioned components in the above-mentioned proportions. Mixing is usually performed in an organic solvent to obtain a photocurable resin composition solution. Specific examples of the organic solvent include ethyl cellosolve acetate, ethylene glycol monoisopropyl ether acetate, propylene glycol monomethyl ether acetate, butyl cellosolve acetate, isopropyl cellosolve acetate, methoxyisopropyl glycol acetate, ethoxyisopropyl glycol acetate, diglyme, and the like. It is not limited. It is desirable to dilute this solution with an organic solvent to an appropriate viscosity in a coating machine as described below.

The photocurable resin composition solution obtained as described above is applied to a transparent substrate after being filtered and dried in order to remove foreign matters. Filtering is carried out using a conventional filter. The coating on the transparent substrate is performed by a known method using various coaters such as a spin coater and a roll coater. A thin film of a photocurable resin composition applied to a transparent substrate and dried, an electron beam, an ultraviolet ray,
It is irradiated with an active energy ray such as visible light to form a cured film. This cured film becomes the dye receiving layer. The thickness of the cured film is 0.1 to 5 μm, preferably 0.5 to 3 μm.

Next, a method for manufacturing the color filter of the present invention will be described. First, a method for producing a transparent substrate having a dye receiving layer for a color filter will be described. If necessary, the photocurable resin composition used in the present invention is dissolved in the above-mentioned solvent to obtain a coating liquid (photosensitive resin liquid). None, it is applied to a base material such as a smooth glass plate or a glass plate on which Cr is vapor-deposited by a spinner, and further dried to form a smooth coating film. In order to form the desired image on this coating film,
Irradiate ultraviolet rays through a negative mask. At this time, a device such as mask alignment is used so that parallel rays are uniformly irradiated on the entire coating film. Next, this irradiated coating film is heated for a short time to promote polymerization, and then running water of a developing solution or
The desired image (dye receiving layer pixel) is obtained by exposing to a shower to dissolve the uncured portion and developing. As the developing method, there are a dipping rocking method, a shower developing method, and the like, and as a developing solution, an inorganic alkali such as sodium carbonate, potassium carbonate, caustic soda, and caustic potassium, tetramethylammonium hydroxide, diethanolamine,
Organic alkali such as triethanolamine is used,
These concentrations vary depending on the alkali, but 1%
Used in dilute aqueous solution before and after. Further, a surfactant may be used in combination, and any of nonionic, anionic and cationic surfactants can be used, and it is generally used at a concentration of 1% or less.

Next, the method for producing the sheet having the sublimable dye-containing layer will be described. A known method is prepared by dissolving the sublimable dye and the binder resin in a solvent on a substrate sheet (film) having a heat resistant slipping layer. The sheet is obtained by applying and drying by the method. The binder resin used here is preferably a resin that dissolves or holds a sublimable dye in a monodisperse state as much as possible, and has a low affinity with the dye, and easily releases the dye when heated. Examples thereof include butyral resin, acetal resin, and polymethylmethacrylate-modified acetal resin.

The above sheet is usually called an ink ribbon. The thickness of the sublimable dye-containing layer on the ink ribbon varies depending on the purpose of use, but is usually about 0.5 to 10 μm, and in the case of a color filter, it is thicker (for example, 4 to 8 μm).
μm) is better. In this way, a transfer ink ribbon coated with the green ink layer is formed, and then the ink side (sublimable dye-containing layer surface) of this ink ribbon is placed on the sublimable dye-receiving substrate (sublimable dye receiving layer). It is superposed on the cured film surface of the photocurable resin composition), and the ink layer is heated by a heating means such as a thermal head or laser light to cure the sublimable dye in the ink on the substrate for dyeing the sublimable dye of the present invention. A color filter is formed by transferring a predetermined pattern on the film.
Incidentally, the transfer method is not limited to this,
It is also possible to adopt a method in which a film coated with a solid dye ink is superposed on a dye receiving layer, and the ink is transferred by irradiating flash light through a mask having a predetermined pattern. The substrate for dyeing the sublimable dye and the sheet having the sublimable dye-containing layer may be in close contact with each other, and may be up to about 500 μm, preferably up to about 300 μm, more preferably 200 μm.
There may be an interval of up to about m.

Further, in order to manufacture a color filter of three primary colors of red, green and blue (R, G, B), for example, the above-mentioned green mixed dye and a sublimable red water-insoluble dye or a sublimable blue non-color dye are used. A water-soluble dye is used to form a transfer ink ribbon in which R, G, and B ink layers are sequentially arranged as described above, and then the ink side of this ink ribbon (sublimable dye-containing layer surface) Is superposed on the sublimable dye receiving layer (cured film surface of the photocurable resin composition) on the substrate for dyeing a sublimable dye, and R, G, B color ink layers are formed by heating means such as a thermal head or laser light. The color filter may be formed by sequentially heating and transferring the sublimable dye in the ink into a predetermined pattern on the cured film on the substrate for dyeing the sublimable dye. Examples of sublimable red water-insoluble dyes and sublimable blue water-insoluble dyes include, for example, Kayaset Scarlet 926 and Kayaset Blue 714.
(All are manufactured by Nippon Kayaku Co., Ltd.) and other sublimable resin coloring dyes.

[0042]

EXAMPLES The present invention will be described in more detail with reference to Reference Examples, Synthesis Examples and Examples. In the following examples, parts represent parts by weight. Synthesis Example 1 (Synthesis of Dye [IV]) In 60 parts of acetic anhydride, 2.8 parts of N, N-diethylamino-3-acetylamino-4-nitrosoaniline and 3-dicyanovinylindan-1-one 2.0 were added. 25 parts
React for 2 hours at ℃. After the reaction, the precipitated crystals were filtered, washed with 20 parts of ethanol and dried to give a crude dye of 4.0.
Get the part. This is recrystallized from toluene to obtain a purified dye. The purified dye has a melting point of 206-208 ℃, λmax = 676nm
(In acetone (the same applies hereinafter)).

Synthesis Example 2 (Synthesis of Dye [V]) N, N-di (n-propyl) amino-3-acetylamino-4-nitrosoaniline 3.3 in 60 parts of acetic anhydride was used.
And 2.0 parts of 3-dicyanovinylindan-1-one are charged and reacted at 25 ° C. for 2 hours. After the reaction, the precipitated crystals are filtered, washed with 20 parts of ethanol and dried to obtain 3.5 parts of a crude dye. This is recrystallized from toluene to obtain a purified dye. The purified dye has a melting point of 172-175 ° C, λma
It was x = 680 nm.

Synthesis Example 3 (Synthesis of Dye [VI]) 3.3 parts and 3 parts of N, N-diethylamino-3-propionylamino-4-nitrosoaniline in 60 parts of acetic anhydride.
-Prepare 2.0 parts of dicyanovinylindan-1-one and react at 25 ° C for 2 hours. After the reaction, the precipitated crystals are filtered, washed with 20 parts of ethanol and dried to obtain 3.5 parts of a crude dye. This is recrystallized from toluene to obtain a purified dye. The purified dye has a melting point of 198-199 ° C and λmax = 67.
It was 6 nm.

The dyes shown in Table 1 below can be synthesized according to Synthesis Example 1.

[0046]

[Table 1] Table 1 R ₁ R ₂ R ₃ X λmax CH ₃ CH ₃ CH ₃ H 673nm CH ₃ n-C ₄ H ₉ n-C ₄ H ₉ H 680nm C ₂ H ₅ CH ₃ CH ₃ H 674nm n- C ₃ H ₇ C ₂ H ₅ C ₂ H ₅ H 676nm n-C ₄ H ₉ C ₂ H ₅ C ₂ H ₅ H 676nm CF ₃ C ₂ H ₅ C ₂ H ₅ H 671nm CH ₃ C ₂ H ₅ C _{2 H 5 OCH 3 688nm CH 3 C} 2 H 5 C 2 H 5 OC 2 H 5 688nm

Reference Example 1 Styrene-maleic anhydride copolymer (copolymerization ratio 1: 1,
After dissolving 500 parts by weight of a molecular weight of 10,000) in 1300 parts by weight of ethyl cellosolve acetate at room temperature, 10 parts by weight of triethylamine, 2 parts by weight of hydroquinone monomethyl ether, polyethylene glycol monomethacrylate manufactured by NOF CORPORATION (brand name Blemmer PE-
90) after adding 109 parts by weight at room temperature.
The reaction was carried out at 3 ° C. for 3 hours. The reaction solution was cooled to 80 ° C., 250 parts by weight of hydroxyethyl acrylate was added, and the mixture was allowed to react again at 90 to 95 ° C. for 3 hours to give a solution of an easily developable unsaturated group-containing polycarboxylic acid resin in ethyl cellosolve acetate. Got The viscosity of this solution is 250
CPS (25 ° C.), acid value (component excluding solvent) 159.
It was 8 mgKOH / g, and the peak of the acid anhydride group was not observed by the measurement by infrared spectroscopy. The ratio of the constituent components of the obtained polycarboxylic acid resin is (A), where the constituent components represented by the following formulas are (A), (B) and (C), respectively:
(B) :( C) = 100: 12.5: 87.5.

[0048]

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Reference Example 2 Styrene-maleic anhydride copolymer (copolymerization ratio 1: 1,
After dissolving 40.4 parts by weight of molecular weight 10,000) in 113 parts by weight of ethyl cellosolve acetate at room temperature, 1 part by weight of triethylamine, 0.2 part by weight of hydroquinone monomethyl ether, polyethylene glycol monomethacrylate manufactured by NOF CORPORATION (trade name) Blemmer PE-
350) was added at room temperature to 17.5 parts by weight, and then 90 to 9
The reaction was carried out at 5 ° C for 3 hours. After the reaction solution was cooled to 80 ° C., 17.4 parts by weight of hydroxyethyl acrylate was added, and the mixture was allowed to react again at 90 to 95 ° C. for 3 hours to obtain ethyl cellosolve which is an easily developable unsaturated group-containing polycarboxylic acid resin. An acetate solution was obtained. The viscosity of this solution is 272 CPS (25 ° C), acid value (component excluding solvent) 1
It was 51 mgKOH / g, and the peak of the acid anhydride group was not observed by the measurement by infrared spectroscopy. The ratio of the constituent components (above) of the obtained polycarboxylic acid resin is (A):
(B) :( C) = 100: 25: 75.

Reference Example 3 Styrene-maleic anhydride copolymer (copolymerization ratio 1: 1,
After dissolving 40.4 parts by weight of molecular weight 10,000) in 130 parts by weight of ethyl cellosolve acetate at room temperature, 1 part by weight of triethylamine, 0.2 part by weight of hydroquinone monomethyl ether, polyethylene glycol monomethacrylate manufactured by NOF CORPORATION (trade name) Blemmer PE-
350) and 35.0 parts by weight at room temperature.
The reaction was carried out at 0 to 95 ° C for 3 hours. After the reaction solution was cooled to 80 ° C., hydroxyethyl acrylate was added to 11.
By adding 6 parts by weight and reacting again at 90 to 95 ° C. for 3 hours, an ethyl cellosolve acetate solution of an easily developable unsaturated group-containing polycarboxylic acid resin was obtained. This solution has a viscosity of 294 CPS (25 ° C) and an acid value of 121.5 mg KO.
H / g, and no peak of an acid anhydride group was observed by measurement by infrared spectroscopy. The ratio of the constituent components (above) of the obtained polycarboxylic acid resin is (A) :( B) :( C) = 1.
It was 00:50:50.

Reference Example 4 Styrene-maleic anhydride copolymer (copolymerization ratio 2: 1,
After dissolving 45.9 parts by weight of a molecular weight of 10,000 in 101 parts by weight of ethyl cellosolve acetate at room temperature, 1 part by weight of triethylamine, 0.2 part by weight of hydroquinone monomethyl ether, polyethylene glycol monomethacrylate manufactured by NOF CORPORATION (trade name) Blemmer PE-
350) was added at 6.45 parts by weight at room temperature and then 90 to 9
The reaction was carried out at 5 ° C for 3 hours. The reaction solution was cooled to 80 ° C., 15.3 parts by weight of hydroxyethyl acrylate was added, and the mixture was allowed to react again at 90 to 95 ° C. for 3 hours to obtain ethyl cellosolve which is an easily developable unsaturated group-containing polycarboxylic acid resin. An acetate solution was obtained. The viscosity of this solution is 284 CPS (25 ° C.), acid value is 127.1 mg KOH /
It was g, and the peak of the acid anhydride group was not seen by the measurement by infrared spectroscopy. The ratio of the constituent components (above) of the obtained polycarboxylic acid resin is (A) :( B) :( C) = 20.
It was 0: 12.5: 87.5.

Reference Example 5 Styrene-maleic anhydride copolymer (copolymerization ratio 2: 1,
After dissolving 45.9 parts by weight of a molecular weight of 10,000) in 108 parts by weight of ethyl cellosolve acetate at room temperature, 1 part by weight of triethylamine, 0.2 part by weight of hydroquinone monomethyl ether, polyethylene glycol monomethacrylate manufactured by NOF CORPORATION (trade name) Blemmer PE-
350) and 13.1 parts by weight at room temperature.
The reaction was carried out at 5 ° C for 3 hours. The reaction solution was cooled to 80 ° C., 13.1 parts by weight of hydroxyethyl acrylate was added, and the mixture was allowed to react again at 90 to 95 ° C. for 3 hours to obtain ethyl cellosolve which is an easily developable unsaturated group-containing polycarboxylic acid resin. An acetate solution was obtained. The viscosity of this solution is 303 CPS (25 ° C), acid value is 103.1 mgKOH /
It was g, and the peak of the acid anhydride group was not seen by the measurement by infrared spectroscopy. The ratio of the constituent components (above) of the obtained polycarboxylic acid resin is (A) :( B) :( C) = 20.
It was 0:25:75.

Reference Example 6 In Reference Example 4, the same reaction was carried out by changing the ethyl cellosolve acetate to propylene glycol monomethyl ether acetate, and the ratio of the constituents was (A) :( B):
(C) = 200: 12.5: 87.5 A propylene glycol monomethyl ether acetate solution of an easily developable unsaturated group-containing polycarboxylic acid resin was obtained.

Reference Example 7 15 parts by weight of an ethyl cellosolve acetate solution of the unsaturated group-containing polycarboxylic acid resin obtained in Reference Example 1, 4 parts by weight of Aronix M-315 manufactured by Toagosei Co., Ltd., and Ciba-Geigy 0.8 parts by weight of Irgacure 369, a photopolymerization initiator, 0.4 parts by weight of DETX-S (diethylthioxanthone) manufactured by Nippon Kayaku Co., Ltd., 0.4 parts of biimidazole manufactured by Kurogane Kasei Co., Ltd. By mixing 0.4 parts by weight of 2-mercaptobenzothiazole and 26 parts by weight of ethyl cellosolve acetate, a photosensitive resin liquid was obtained.

Reference Examples 8 to 11 Using the ethylcellosolve acetate solutions of the unsaturated group-containing polycarboxylic acid resins obtained in Reference Examples 2 to 5, photosensitive resin solutions were obtained in the same manner as in Reference Example 7. .

Reference Example 12 Using the propylene glycol monomethyl ether acetate solution of the unsaturated group-containing polycarboxylic acid resin obtained in Reference Example 6, a photosensitive resin liquid was obtained in the same manner as in Reference Example 7.

Example 1 The photosensitive resin liquid obtained in Reference Example 1 was applied to a glass substrate with a spinner and predried at 100 ° C. for 100 seconds,
150mj / cm with ultra high pressure mercury lamp through negative mask
^Two exposures were made. Then, a sublimation dye dyeing patterning only the UV irradiation portion by developing in an aqueous solution shower containing 0.1% tetramethylammonium hydroxide and 0.2% nonionic surfactant for 30 seconds, washing with water and post-baking. A substrate for use was obtained. The patterned pixels had a good resolution and no residue was found in the developed area. On the other hand, methyl ethyl ketone / toluene (1/1 weight) in which 1 part of the dye [IV] and 1 part of the pyridone azo dye of the above formula (vi) are dissolved in 2 parts of polyvinyl butyral (trade name: PVB300K Sekisui Chemical Co., Ltd.) Ratio) Dissolved in 100 parts of the mixed solution to obtain a coating solution. This solution was applied using a wire bar so that the film thickness when dried was about 6 μm to prepare a green ink ribbon. The heating element of the thermal head is used to partially heat the thus produced ink ribbon to color the dye receiving layer surface of the sublimation dye dyeing substrate prepared above to obtain a green color filter.

Reference Example 13 11.25 parts by weight of a propylene glycol monomethyl ether acetate solution of the unsaturated group-containing polycarboxylic acid resin obtained in Reference Example 6 and 3.6 of Aronix M-315 manufactured by Toagosei Co., Ltd. Parts by weight, KA manufactured by Nippon Kayaku Co., Ltd.
0.9 parts by weight of YARADR2225 (phenol novolac type epoxy acrylate), 1 part by weight of Techmore VG3101 (trisphenol type epoxy) manufactured by Mitsui Petrochemical Co., Ltd., 0.8 parts of IRGACURE 369 photopolymerization initiator manufactured by Ciba-Geigy Parts by weight, 0.4 parts by weight of DETX-S manufactured by Nippon Kayaku Co., 0.4 parts by weight of biimidazole manufactured by Kurogane Kasei Co., Ltd., 0.4 parts by weight of 2-mercaptobenzothiazole, ethylene glycol A photosensitive resin liquid was obtained by mixing 26 parts by weight of monoisopropyl ether acetate.

Example 2 The photosensitive resin liquid obtained in Reference Example 13 was applied on a glass substrate by a spinner and pre-dried at 100 ° C. for 100 seconds, then, through a negative mask, an ultrahigh pressure mercury lamp of 150 mj /
cm ^{2 was} exposed. Then, a sublimation dye dyeing patterning only the UV irradiation portion by developing in an aqueous solution shower containing 0.1% tetramethylammonium hydroxide and 0.2% nonionic surfactant for 30 seconds, washing with water and post-baking. A substrate for use was obtained. The patterned pixels had a good resolution and no residue was found in the developed area. The film thickness of the cured film of the photocurable resin composition obtained here was 1 to 2 μm. On the other hand, methyl ethyl ketone / toluene (1) in which 1 part of the dye [V] and 1 part of the pyridone azo dye of the above formula (vi) are dissolved in 2 parts of polyvinyl butyral (trade name: PVB300K Sekisui Chemical Co., Ltd.)
(1 / weight ratio) It was dissolved in 100 parts of the mixed solution to obtain a coating solution. This solution was applied using a wire bar so that the film thickness when dried was about 6 μm to prepare a green ink ribbon. The heating element of the thermal head is used to partially heat the thus produced ink ribbon to color the dye receiving layer surface of the sublimation dye dyeing substrate prepared above to obtain a green color filter.

Reference Example 14 Benzyl methacrylate, methyl methacrylate and methacrylic acid were polymerized by a known method in an ethylene glycol monoisopropyl ether acetate solvent at a ratio of 68:17:15 (molecular weight 10
000) 27 parts by weight, Toagosei Co., Ltd. Aronix M-315 4 parts by weight, Ciba-Geigy photopolymerization initiator Irgacure 369 0.8 parts by weight, Nippon Kayaku Co., Ltd. DETX 0.4 parts by weight of -S, Kurogane Kasei Co., Ltd.
0.4 parts by weight of Biimidazole, 0.4 parts by weight of 2-mercaptobenzothiazole and 26 parts by weight of ethylene glycol monoisopropyl ether acetate were mixed to obtain a photosensitive resin liquid.

Example 3 The photosensitive resin liquid obtained in Reference Example 14 was applied to a glass substrate by a spinner and pre-dried at 100 ° C. for 100 seconds, and then 150 mj / min was passed through a negative mask with an ultrahigh pressure mercury lamp.
cm ^{2 was} exposed. Then, a sublimation dye dyeing substrate in which only UV irradiation portions are patterned by developing for 30 seconds with a 0.1% tetramethylammonium hydroxide and 0.2% nonionic surfactant aqueous solution shower, washing with water and post-baking. was gotten. The patterned pixels had a good resolution and no residue was found in the developed area. On the other hand, 1 part of the dye [VI] and 1 part of the pyridone-based azo dye of the above formula (vi) are dissolved in 2 parts of polyvinyl butyral (trade name: S-REC B BL-S Co., Ltd. Sekisui Chemical Co., Ltd.) methyl ethyl ketone / toluene ( It was dissolved in 100 parts of the mixed solution (1/1 weight ratio) to obtain a coating solution. This solution was applied using a wire bar so that the film thickness when dried was about 6 μm to prepare a green ink ribbon. The heating element of the thermal head is used to partially heat the thus produced ink ribbon to color the dye receiving layer surface of the sublimation dye dyeing substrate prepared above to obtain a green color filter.

Example 4 The photosensitive resin liquid obtained in Reference Example 14 was applied to a glass substrate by a spinner and pre-dried at 100 ° C. for 100 seconds, then, through a negative mask, an ultrahigh pressure mercury lamp of 150 mj /
cm ^{2 was} exposed. Then, a sublimation dye dyeing substrate in which only UV irradiation portions are patterned by developing for 30 seconds with a 0.1% tetramethylammonium hydroxide and 0.2% nonionic surfactant aqueous solution shower, washing with water and post-baking. was gotten. The patterned pixels had a good resolution and no residue was found in the developed area. On the other hand, 1 part of the dye [VI] is dissolved in 1 part of polyvinyl butyral (trade name: S-REC B BL-S Co., Ltd. Sekisui Chemical Co., Ltd.) methyl ethyl ketone / toluene (1
(1 / weight ratio) was dissolved in 50 parts of the mixed solution to obtain a coating solution. This solution was applied using a wire bar so that the film thickness when dried was about 6 μm to prepare a blue-green ink ribbon. Furthermore, 1 part of the pyridone-based azo dye of the above formula (vi) was added to polyvinyl butyral (trade name: S-REC B B
A coating solution was obtained by dissolving 1 part of L-S Co., Ltd. Sekisui Chemical Co., Ltd. in 50 parts of a mixed solution of methyl ethyl ketone / toluene (1/1 weight ratio). This solution was applied using a wire bar so that the film thickness when dried was about 6 μm to prepare a yellow ink ribbon. Partially heated by the heating element of the thermal head via the yellow ink ribbon thus prepared, the dye-receiving layer surface of the sublimation dye dyeing substrate prepared above is colored yellow, and then thermal is transferred via the blue-green ink ribbon. Partial heating by the heating element of the head, coloring the dye receiving layer surface of the sublimation dye dyeing substrate dyed yellow,
Get the green color filter.

[0063]

INDUSTRIAL APPLICABILITY According to the present invention, a green mixed dye containing an azamethine compound and having excellent spectral characteristics, heat resistance and light resistance can be obtained. At the same time, the sublimation transfer property is excellent, the dye adsorbing ability of the dye receiving layer is good, and a high-density color filter can be obtained by the sublimation transfer method. Since it is not necessary to perform the patterning and the dyeing and fixing treatment three times like the conventional dyeing method of the color filter, the process is remarkably simplified. In addition, the decrease in yield due to dust adherence in the dyeing process is very small. Further, since the green mixed dye of the present invention has excellent sublimation transferability, it is expected as a green dye for a sublimation transfer type color printer.

[Brief description of the drawings]

FIG. 1 is a TG chart of a typical dye [IV] used in the present invention.

FIG. 2 is a transmission spectrum of a green color filter obtained according to Example 1 of the present invention.

[Explanation of symbols]

In FIG. 1, [I] indicates a heat loss curve, and the scale is the weight loss rate on the right side. In the heat loss curve, point A indicates the sublimation start point and point B indicates the 10% weight loss point. In FIG. 1, [II] shows a temperature rising curve, and the scale is the temperature on the left side.

Claims (18)

[Claims] 1. The formula [I]: [In the formula [I], R ₁ represents an alkyl group or a trifluoromethyl group, R ₂ and R ₃ each represent an alkyl group, and X represents a hydrogen atom or —OR ₄ (wherein R ₄ represents an alkyl group. )
Represents ] A green mixed dye for sublimation transfer comprising an azamethine compound and a yellow dye. 2. R ₁ is a linear or branched alkyl group having 1 to 4 carbon atoms, R ₂ and R ₃ are linear alkyl groups having 1 to 4 carbon atoms, and R ₄ is a methyl group or The green mixed dye for sublimation transfer according to claim 1, which is an ethyl group. 3. The green mixed dye for sublimation transfer according to claim 1, wherein R ₁ is a methyl group, R ₂ and R ₃ are methyl groups or ethyl groups, and X is a hydrogen atom. 4. The green mixture for sublimation transfer according to any one of claims 1 to 3, wherein the yellow dye is a dye which is selected from quinoline dyes, styryl dyes or azo dyes and is water-insoluble and has sublimability. Pigment. 5. The green mixed dye for sublimation transfer according to claim 4, wherein the azo dye is a pyrazole azo dye or a pyridone azo dye. 6. The green mixed dye for sublimation transfer according to any one of claims 1 to 4, wherein the yellow dye is a water-insoluble and sublimable pyridone azo dye. 7. The sublimation initiation temperature of a yellow dye is 170 to 260.
The green mixed dye for sublimation transfer according to any one of claims 1 to 6, which has a temperature of ° C. 8. The mixing ratio of the azamethine compound and the yellow pigment is 0.2 to 4 yellow pigment to 1 part by weight of the azamethine compound.
The green mixed dye for sublimation transfer according to any one of claims 1 to 7, which is parts by weight. 9. A color filter comprising the green mixed dye for sublimation transfer according to claim 1. Description: 10. A dye-containing layer surface of a transparent substrate having a dye-receiving layer on its surface and a dye-containing layer surface of a sheet having a green mixed dye-containing layer for sublimation transfer according to any one of claims 1 to 8. A method of manufacturing a color filter, comprising heating the sheet after heating. 11. The method for producing a color filter according to claim 10, wherein the dye receiving layer is a cured film of a photocurable resin composition containing a resin having an acid value of 80 mgKOH / g or more. 12. The resin having an acid value of 80 or more is a resin containing a carboxylic acid group and a carboxylic acid ester group or a polymer of (meth) acrylic acid (ester).
Of manufacturing color filter of. 13. A resin containing a carboxylic acid group and a carboxylic acid ester group, which is a copolymer of maleic anhydride and one or more kinds of monomers copolymerizable with maleic anhydride. the portion of maleic anhydride is the following formula _{(1) HO (C 2 H} 4 O) n -A (1) [wherein a is an acryloyl or methacryloyl group, n represents 1 or 2. A compound represented by], and the following formula _{(2) HO (C 2 H} 4 O) n -R (2) wherein R represents an alkyl group, an alkylphenyl group, Arukaroiru group or (meth) acryloyl group, n represents an integer of 2 or more. ] The manufacturing method of the color filter of Claim 12 which is the unsaturated group containing polycarboxylic acid resin half-esterified with the compound represented by these. 14. A monomer copolymerizable with maleic anhydride is styrene, α-methylstyrene, isobutylene,
The method for producing a color filter according to claim 13, wherein the color filter is (meth) acrylic acid alkyl ester or benzyl (meth) acrylate. 15. The weight average molecular weight of maleic anhydride and a copolymer comprising one or more kinds of monomers copolymerizable with maleic anhydride has a weight average molecular weight of 5,000 or more.
4. The method for manufacturing the color filter of 4. 16. The reaction rate of half-esterification is 50 to 10.
It is 0%, The manufacturing method of the color filter as described in any one of Claim 13 thru | or 15. 17. The method for producing a color filter according to claim 12, wherein the (meth) acrylic acid (ester) polymer is a polymer of methyl methacrylate, benzyl methacrylate or methacrylic acid. 18. The method for producing a color filter according to claim 11, wherein the photocurable resin composition is a composition containing an epoxy compound.