JP2013041156A - Colored resin composition, color filter, liquid crystal display device, and organic el display device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a colored resin composition capable of providing pixels of a color filter with excellent luminance and satisfying heat resistance required in a color display manufacturing process, and to provide a color filter having pixels with excellent chromatic purity and transmission factor by using the colored resin composition, a high-quality liquid crystal display device, and an organic EL display device.SOLUTION: The colored resin composition includes (A) dye, (B) solvent, and (C) a binder resin, and further includes a chemical compound expressed by a specific structure.

Description

  The present invention resides in a colored resin composition, a color filter, a liquid crystal display device, and an organic EL display device.

In recent years, color liquid crystal display devices and organic EL displays have attracted attention as flat displays, and color filters are used for these displays.
For example, a color liquid crystal display device includes, as an example, a black matrix, a colored layer composed of a plurality of colors (usually three primary colors of red (R), green (G), and blue (B)), a transparent electrode, and an alignment layer. The color filter substrate provided, the thin film transistor (TFT element), the counter electrode substrate provided with the pixel electrode and the alignment layer, and the two substrates are opposed to each other with a predetermined gap, sealed with a sealing member, There is a transmissive liquid crystal display device that is roughly configured from a liquid crystal layer formed by injecting a liquid crystal material. There is also a reflective liquid crystal display device in which a reflective layer is provided between the color filter substrate and the colored layer.

  On the other hand, in principle, an organic EL display has an organic EL element having a structure in which an organic EL light-emitting layer is sandwiched between an anode and a cathode. In order to obtain a possible organic EL display, (1) a method of arranging organic EL elements that emit light of each of the three primary colors, (2) a method of combining organic EL elements that emit white light with a color filter layer of the three primary colors, And (3) a CCM system that combines an organic EL element that emits blue light and a color conversion layer (CCM layer) that performs color conversion from blue to green and blue to red, respectively.

Needless to say, the method of (1) is characterized in that high color reproducibility can be exhibited because organic EL elements of each color are used. Therefore, by placing color filters corresponding to the organic EL elements of each color, improvement in color reproducibility and improvement in contrast by absorbing reflected light can be expected. .
In addition, the combination method of the white organic EL and the color filter in (2) and the CCM method in (3) may use only one type of organic EL element that emits light of the same color. Unlike the EL display, it is not necessary to align the characteristics of the organic EL elements of each color, and the number of processes and materials can be reduced.

  In an organic EL element using a color filter and a color conversion method including a color conversion filter and an organic light emitter, heat resistance required in the color display manufacturing process, weather resistance when used as a display, and For those requiring high-definition images, it is the mainstream to use color filters created by the pigment dispersion method, and red, blue or green pigments in the photosensitive resin solution have a particle size of 1 μm or less. After the finely dispersed material is applied on a glass substrate, pixels are formed in a desired pattern by photolithography.

For color filters, improvements in color purity, saturation, and light transmission are required. Conventionally, for the purpose of improving light transmission, the content of pigment in the photosensitive resin in the image forming material is reduced. Alternatively, a method has been adopted in which the thickness of a pixel formed from an image forming material is reduced. However, with these methods, the saturation of the color filter itself is lowered, the entire display becomes whitish, and the vividness of the color necessary for display is sacrificed. Conversely, the pigment content is increased in favor of saturation. If this is done, the entire display becomes dark, and in this case, the amount of light from the backlight must be increased in order to ensure brightness, leading to an increase in power consumption of the display.

On the other hand, for the purpose of improving the light transmission amount, a method of finely dispersing the pigment particle diameter to 1/2 or less of the coloration wavelength is known (Non-Patent Document 1). Since the coloration wavelength is shorter than that of other red and green pigments, further fine dispersion is required in this case, resulting in problems of cost increase and stability after dispersion.
On the other hand, color filters using dyes as colorants are still being developed. For example, Patent Document 1 describes a color filter provided with a blue filter layer containing C.I. Acid Blue 83 (triallylamine dye) and C.I. Solvent Blue 67 (copper phthalocyanine dye). ing.

One of the important items for putting a color filter using a dye into practical use is heat resistance.
As a method for improving heat resistance, modification of the dye molecule structure has been the mainstream until now. For example, in Patent Documents 1 to 3, a triallylmethane dye or a copper phthalocyanine dye has been molecularly modified. Have been described.

  Further, for example, Patent Documents 4 to 6 describe that the heat resistance is improved without modifying the dye structure by containing an antioxidant in the colored resin composition.

Japanese Patent Laid-Open No. 2002-14222 JP 2000-162429 A JP 2008-304766 A JP 2009-122650 A JP 2009-122650 A JP 2010-134278 A

Kiyoshi Hashizume “Journal of Color Material Association” (December 1967, page 608)

However, the dyes described in Patent Documents 1 to 3 have insufficient heat resistance. Furthermore, when a molecular modification is performed with a substituent or the like, a change in transmission spectrum due to the substituent or a decrease in solubility in a solvent tends to occur.
Further, even with the method described in Patent Document 4, the heat resistance is not sufficiently improved.
In view of the above problems, the present invention provides a colored resin composition that can provide a pixel of a color filter excellent in luminance and that also satisfies the heat resistance required in the color display manufacturing process described above. Objective. Another object of the present invention is to provide a color filter excellent in color purity and transmittance of a pixel, a high-quality liquid crystal display device, and an organic EL display device by using such a colored resin composition.

As a result of intensive studies, the present invention and the like show that when a pixel is formed using a colored resin composition containing a dye, the material contained in the colored resin composition, particularly the dye, is heated by a heating process during pixel formation. It has been found that the above-mentioned problem is that it is deteriorated.
Furthermore, as a result of intensive studies, the present inventors have found that the above problems can be solved by containing an antioxidant and a specific compound, and have arrived at the present invention.

  That is, the present invention is a colored resin composition containing (A) a dye, (B) a solvent, and (C) a binder resin, and further includes a compound represented by the following formula (I) and / or the following ( II) It exists in the colored resin composition, color filter, liquid crystal display device, and organic electroluminescent display device characterized by containing the compound represented by.

(In the above formula (I),
l represents an integer of 1 to 5;
R ¹ may have a hydrogen atom, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, an aromatic ring group which may have a substituent, or a substituent. Represents a heterocyclic group.
R ² and R ³ represent a hydrogen atom, a hydroxyl group, an aromatic ring group which may have a substituent, or a heterocyclic group which may have a substituent.

  The benzene ring in the above formula (I) may have a substituent in addition to the hydroxyl group. )

(In the above formula (II),
m represents an integer of 0 to 4, and n represents an integer of 0 to 5.
However, m + n is 1 or more.
R ⁴ represents a hydrogen atom, a hydroxyl group, an alkoxyl group which may have a substituent, an aromatic ring group which may have a substituent, or a heterocyclic group which may have a substituent. Represent.

  The benzene ring in the above formula (II) may have a substituent other than the hydroxyl group. )

According to the present invention, a color filter having heat resistance required in a color display manufacturing process and excellent in color purity and transmittance of pixels can be obtained. By using such a color filter, the light emission of the organic EL display device and the light emission of the backlight of the color filter can be taken out efficiently, and a liquid crystal display device and an organic EL device that achieve both high color reproducibility and high luminance. A display device can be provided.

It is a section schematic diagram showing an example of an organic EL device which has a color filter of the present invention.

Embodiments of the present invention will be described in detail below, but the following description is an example of embodiments of the present invention, and the present invention is not limited to these contents.
In the present invention, “(meth) acryl”, “(meth) acrylate” and the like mean “acryl and / or methacryl”, “acrylate and / or methacrylate” and the like, for example, “(meth) acrylic acid” "Means" acrylic acid and / or methacrylic acid ".

Further, “total solid content” means all components of the colored resin composition of the present invention other than the solvent components described later.
In the present invention, “coloring material” means both “dye” and “pigment”. Furthermore, “aromatic ring” means “aromatic hydrocarbon ring” and “aromatic heterocyclic ring”. It shall mean both.

Moreover, terms such as “CI Pigment Green” mean a color index (CI).
The colored resin composition of the present invention is a colored resin composition containing (A) a dye, (B) a solvent, and (C) a binder resin, and further a compound represented by the following formula (I) , Sometimes referred to as “compound (I)”) and / or a compound represented by the following (II) (hereinafter, sometimes referred to as “compound (II)”).

(In the above formula (I),
l represents an integer of 1 to 5;
R ¹ may have a hydrogen atom, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, an aromatic ring group which may have a substituent, or a substituent. Represents a heterocyclic group.
R ² and R ³ represent a hydrogen atom, a hydroxyl group, an aromatic ring group which may have a substituent, or a heterocyclic group which may have a substituent.

  The benzene ring in the above formula (I) may have a substituent in addition to the hydroxyl group. )

(In the above formula (II),
m represents an integer of 0 to 4, and n represents an integer of 0 to 5.
However, m + n is 1 or more.
R ⁴ represents a hydrogen atom, a hydroxyl group, an alkoxyl group which may have a substituent, an aromatic ring group which may have a substituent, or a heterocyclic group which may have a substituent. Represent.

The benzene ring in the above formula (II) may have a substituent other than the hydroxyl group. )
First, the compound (I) and the compound (II) contained in the colored resin composition of the present invention will be described in detail.
[Compounds (I) and (II)]
[1] About compound (I)

(In the above formula (I),
l represents an integer of 1 to 5;
R ¹ may have a hydrogen atom, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, an aromatic ring group which may have a substituent, or a substituent. Represents a heterocyclic group.
R ² and R ³ represent a hydrogen atom, a hydroxyl group, an aromatic ring group which may have a substituent, or a heterocyclic group which may have a substituent.

The benzene ring in the above formula (I) may have a substituent in addition to the hydroxyl group. )
(About l)
It is preferable that l is 2 or more and 5 or less in that the luminance of the obtained pixel is easily improved.

(About R ¹ )
R ¹ may have a hydrogen atom, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, an aromatic ring group which may have a substituent, or a substituent. Represents a heterocyclic group.
The hydrocarbon group may be linear or branched, may be saturated or unsaturated, and is not particularly limited as long as it has 1 to 8 carbon atoms, but is not limited to methyl, ethyl, n-propyl, 2-propyl. Group, n-butyl group, isobutyl group, tert-butyl group, cyclohexyl group and the like.

Examples of the aromatic ring group include an aromatic hydrocarbon ring group and an aromatic heterocyclic group.
The aromatic hydrocarbon ring group may be a single ring or a condensed ring, and is not particularly limited as long as the number of carbon atoms forming the ring is 5 to 18, but for example, one free valence Benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, fluorene ring and the like.

  The aromatic heterocyclic group may be a single ring or a condensed ring, and is not particularly limited as long as the number of carbon atoms forming the ring is 3 to 10, but for example, one free atom Having a valence, furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole Ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, Synoline ring, quinoxaline ring, phenanthridine ring, Zone imidazole ring, perimidine ring, a quinazoline ring, a quinazolinone ring, groups such as azulene ring.

The free valence in the present invention is based on the description in “Organic Chemistry / Biochemical Nomenclature” (Nanedo, published May 20, 1992, translated by Kenzo Hirayama and Kazuo Hirayama, pages 11-12). It is.
On the other hand, the heterocyclic group (that is, non-aromatic heterocyclic group) may be a single ring or a condensed ring.

The heterocyclic group is a non-aromatic ring group containing any one of a nitrogen atom, a sulfur atom and an oxygen atom as a hetero atom.
When the heterocyclic group has a plurality of ring-constituting atoms other than carbon atoms, these may be the same or different.
Specific examples include a pyridinyl group, a quinolinyl group, an isoquinolinyl group, a benzothiazolinyl group, a phthalimidoyl group, a piperidinyl group, and a pyrrolidinyl group.

R ¹ is preferably a substituent having a hydrogen atom in order to obtain a clear brightness enhancement effect.
(About R ² and R ³ )
R ² and R ³ represent a hydrogen atom, a hydroxyl group, an aromatic ring group which may have a substituent, or a heterocyclic group which may have a substituent.

The aromatic ring group and the heterocyclic group are the same as those described in the above section (for R ¹ ).
R ² and R ³ are preferably electron-withdrawing groups in that the molecules are delocalized and the molecule is more stable, and steric hindrance is unlikely to occur, and synthesis is easy. Of these, a hydroxyl group or a methoxy group is preferable.

In addition, a hydrogen atom is particularly preferable from the viewpoint of easier synthesis.
(About substituents)
Examples of the substituent that the aromatic ring group and the heterocyclic group in R ^{1 to} R ³ and the benzene ring in the formula (I) may have include the following [Substitution group W]. Is not limited to these.

[Substituent group W]
Fluorine atom, chlorine atom, alkyl group having 1 to 8 carbon atoms, alkenyl group having 2 to 8 carbon atoms, alkoxyl group having 1 to 8 carbon atoms, phenyl group, mesityl group, tolyl group, naphthyl group, cyano group, acetyloxy Group, alkyl carboxyl group having 2 to 9 carbon atoms, sulfonic acid amide group, sulfone alkylamide group having 2 to 9 carbon atoms, alkylcarbonyl group having 2 to 9 carbon atoms, phenethyl group, hydroxyethyl group, acetylamide group, carbon A dialkylaminoethyl group formed by bonding an alkyl group having 1 to 4 carbon atoms, a trifluoromethyl group, a trialkylsilyl group having 1 to 8 carbon atoms, a nitro group, an alkylthio group having 1 to 8 carbon atoms, an aromatic ring group, Aromatic heterocyclic group.

Among the above, when the aromatic ring group and the heterocyclic group in R ^{1 to} R ³ have a substituent, the charge of the molecule is delocalized and the molecule is more stable, and thus the electron withdrawing property is obtained. Of these, a hydroxyl group or a methoxy group is particularly preferred from the viewpoint that steric hindrance hardly occurs and synthesis is easy.
Further, it is preferably unsubstituted from the viewpoint that steric hindrance hardly occurs and synthesis is easy.

Among the above, when the benzene ring in the formula (I) has a substituent other than the hydroxyl group, an alkoxy group, an aromatic ring group, or a heterocyclic group can be mentioned, and the heat resistance and luminance are easily improved. Alkoxyl groups are preferred.
The benzene ring in the formula (I) may have a substituent other than the hydroxyl group, but it may not have a substituent in terms of improving the solubility in an organic solvent. preferable.

The compound (I) of the present invention may form a dimer or trimer by extending a linker from any of R ^{1 to} R ³ and the benzene ring, or by directly bonding the linker.
(Molecular weight)
The molecular weight of the compound (I) is usually 160 or more, and usually 800 or less, preferably 600 or less.

Within the above range, it is preferable in that synthesis is easy.
Preferred specific examples of the compound represented by formula (I) are shown below, but the present invention is not limited thereto.
<Specific example>

  [2] About compound (II)

(In the above formula (II),
m represents an integer of 0 to 4, and n represents an integer of 0 to 5.
However, m + n is 1 or more.
R ⁴ represents a hydrogen atom, a hydroxyl group, an alkoxyl group which may have a substituent, an aromatic ring group which may have a substituent, or a heterocyclic group which may have a substituent. Represent.

The benzene ring in the above formula (II) may have a substituent other than the hydroxyl group. )
(About m and n)
It is preferable that m is 1 or more and 4 or less in that the luminance is easily improved.
Similarly, n is preferably 1 or more and 5 or less from the viewpoint that the luminance is easily improved.

m + n is preferably 2 or more and 9 or less from the viewpoint that it becomes easy to trap radicals generated in the system by delocalizing electrons in the molecule, and suppresses a decrease in luminance of the obtained color filter. .
The benzene ring in the above formula (II) may have a substituent other than the hydroxyl group, and examples of the substituent include those described in the above section [Substituent group W].

The preferred embodiment is also the same.
The compound represented by the formula (II) are, for example, extending the linker from R ⁴ and the benzene ring, it may form such a dimer or trimer.
(Molecular weight)
The molecular weight of the compound (II) is usually 250 or more, and usually 800 or less, preferably 600 or less.

Within the above range, it is preferable in that synthesis is easy.
Although the preferable specific example of compound (II) in this invention is shown below, this invention is not limited to these.
<Specific examples of compound (II)>

[Reason for effect]
The reason why the effect that the luminance and heat resistance of the obtained pixel are high by including compound (I) and / or compound (II) in the colored resin composition is estimated as follows.
When forming a pixel using a colored resin composition, after forming a coating film, it dries and goes through a baking process. During the baking step, radicals (singlet oxygen) generated from the initiator in the film react with the dye. As a result, heat resistance is reduced.

Here, when there is compound (I) or compound (II), since singlet oxygen is eliminated before reacting with the dye, a decrease in heat resistance is suppressed.
Compound (I) and compound (II) have a hydroxyl group which is an electron withdrawing group in the molecule. For this reason, even if a radical is received from singlet oxygen, the charges of the compound (I) and the compound (II) are delocalized and stabilized as a whole molecule. For this reason, the compound (I) and the compound (II) have a higher radical trapping ability than other additives, and the effects of the present invention can be obtained.

[Content]
The content of compound (I) and / or compound (II) in the present invention is a total amount, and is usually 0.01% by weight or more, preferably 0.1% by weight or more, more preferably in the solid content of the colored resin composition. Is 0.5% by weight or more, usually 10% by weight or less, preferably 5% by weight or less, more preferably 3% by weight or less.

It is preferable that the luminance is within the above range in that the obtained pixel has good luminance.
[Other antioxidants]
The colored resin composition of the present invention may contain a compound represented by the following formula (III) (hereinafter sometimes referred to as “compound (III)”).

(In the above formula (III),
p represents an integer of 0 to 4, and q represents an integer of 0 to 5.
However, p + q is 1 or more.
R ⁵ and R ⁶ are a hydrogen atom, a hydroxyl group, an alkoxyl group which may have a substituent, an aromatic ring group which may have a substituent, or a heterocycle which may have a substituent. Represents a cyclic group.

The benzene ring in the above formula (III) may have a substituent other than the hydroxyl group. )
(About p and q)
p and q are the same as those described for m and n in formula (II), respectively. The preferred embodiment is also the same.

(About R ⁵ and R ⁶ )
R ⁵ and R ⁶ have the same meaning as R ⁴ in formula (II). The preferred embodiment is the same.
The benzene ring in the above formula (III) may have a substituent other than the hydroxyl group, and examples of the substituent include those described in the above section [Substituent group W].
The preferred embodiment is also the same.

Compound (III) may form a dimer or a trimer by extending a linker from R ^5, R ⁶ and the benzene ring.
(Molecular weight)
The molecular weight of the compound (II) is usually 250 or more, and usually 800 or less, preferably 600 or less.

Within the above range, it is preferable in that synthesis is easy.
Although the preferable specific example of compound (III) is shown below, this invention is not limited to these.
[Specific Examples of Compound (III)]

[(A) Dye]
In the present invention, the dye (A) that can be used as a colorant is not particularly limited as long as the effects of the present invention are not impaired. For example, azo dyes, anthraquinone dyes, phthalocyanine dyes, quinoneimine dyes, quinoline dyes Dyes, nitro dyes, carbonyl dyes, methine dyes, cyanine dyes, triarylmethane dyes and the like are preferred.

Examples of the azo dye include C.I. I. Acid Yellow 11, C.I. I. Acid Orange 7, C.I. I. Acid Red 37, C.I. I. Acid Red 180, C.I. I. Acid Blue 29, C.I. I. Direct Red 28, C.I. I. Direct Red 83, C.I. I. Direct Yellow 12, C.I. I. Direct Orange 26, C.I. I. Direct Green 28, C.I. I. Direct Green 59, C.I. I. Reactive Yellow 2, C.I. I
. Reactive Red 17, C.I. I. Reactive Red 120, C.I. I. Reactive Black 5, C.I. I. Disperse Orange 5, C.I. I. Disperse thread 58, C.I. I. Disperse Blue 165, C.I. I. Basic Blue 41, C.I. I. Basic Red 18, C.I. I. Molded Red 7, C.I. I. Moldant Yellow 5, C.I. I. Examples thereof include Moldant Black 7.

Examples of anthraquinone dyes include C.I. I. Bat Blue 4, C.I. I. Acid Blue 40, C.I. I. Acid Green 25, C.I. I. Reactive Blue 19, C.I. I. Reactive Blue 49, C.I. I. Disper thread 60, C.I. I. Disperse Blue 56, C.I. I. Disperse Blue 60 etc. are mentioned.
Other examples of the phthalocyanine dye include C.I. I. Pad Blue 5 and the like are quinone imine dyes such as C.I. I. Basic Blue 3, C.I. I. Basic Blue 9 and the like are quinoline dyes such as C.I. I. Solvent Yellow 33, C.I. I. Acid Yellow 3, C.I. I. Disperse Yellow 64 and the like are nitro dyes such as C.I. I. Acid Yellow 1, C.I. I. Acid Orange 3, C.I. I. Disperse Yellow 42 and the like.

Examples of the triarylmethane dye include those described in International Publication No. 2009/107734 pamphlet.
Furthermore, examples of the cyanine dye include those described in Japanese Patent Application No. 2010-142748, and preferred embodiments thereof are also the same.
The (A) dye in the present invention may be composed of only the above-mentioned dye, but other colorants can be used in combination with the dye. As other coloring materials, dyes and pigments can be used, but pigments are preferable from the viewpoint of heat resistance, light resistance and the like.

  As the pigment in the present invention, various color pigments such as a blue pigment, a green pigment, a red pigment, a yellow pigment, a purple pigment, an orange pigment, a brown pigment, and a black pigment can be used. In addition to the organic pigments such as azo, phthalocyanine, quinacridone, benzimidazolone, isoindoline, quinophthalone, isoindolinone, dioxazine, indanthrene, perylene, etc. Other inorganic pigments can also be used.

As these usable pigments, for example, pigments described in JP-A-2009-025813 can be used.
The content of all the color materials in the colored resin composition of the present invention, that is, the total content of the (A) dye and other color materials is usually 1 to 50% by weight with respect to the total solid content. , Preferably 3 to 40% by weight, more preferably 5 to 30% by weight.
When it is within the above range, the film thickness is appropriate with respect to the color density, and it is easy to control the gap when forming a liquid crystal cell. Furthermore, the dispersion stability is high, and reaggregation and thickening are difficult to place, which is preferable.

[(C) Binder resin]
(C) What preferable binder resin changes with the hardening means of a colored resin composition.
When the colored resin composition of the present invention is a photopolymerizable resin composition, examples of the (C) binder resin include JP-A-7-2072111, JP-A-8-259876, and JP-A-10-300922. The polymers described in JP-A-11-14144, JP-A-11-174224, JP-A-2000-56118, JP-A-2003-233179, and the like can be used. Of these, the following resins (C-1) to (C-5) are preferred.

(C-1): With respect to a copolymer of an epoxy group-containing (meth) acrylate and another radical polymerizable monomer, an unsaturated monobasic acid is added to at least a part of the epoxy group of the copolymer. Resin to be added, or an alkali-soluble resin (hereinafter referred to as “resin (C-1)”) obtained by adding a polybasic acid anhydride to at least a part of the hydroxyl group generated by the addition reaction. .)
(C-2): Carboxyl group-containing linear alkali-soluble resin (C-2) (hereinafter sometimes referred to as “resin (C-2)”)
(C-3): a resin obtained by adding an epoxy group-containing unsaturated compound to the carboxyl group portion of the resin (C-2) (hereinafter sometimes referred to as “resin (C-3)”).
(C-4): (Meth) acrylic resin (hereinafter sometimes referred to as “resin (C-4)”)
(C-5): Epoxy acrylate resin having a carboxyl group (hereinafter sometimes referred to as “resin (C-5)”)
Of these, the resin (C-1) is particularly preferable, and the resin will be described below.

The resins (C-2) to (C-5) may be anything as long as they are dissolved in an alkaline developer and are soluble to the extent that the desired development processing is performed. It is the same as that described as the same item of 2009-025813 gazette. The preferred embodiment is also the same.
(C-1): With respect to a copolymer of an epoxy group-containing (meth) acrylate and another radical polymerizable monomer, an unsaturated monobasic acid is added to at least a part of the epoxy group of the copolymer. As one of particularly preferable resins of the alkali-soluble resin resin (C-1) obtained by adding a polybasic acid anhydride to at least a part of the hydroxyl group generated by the addition reaction, or an epoxy group, Unsaturated in 10 to 100 mol% of the epoxy group of the copolymer with respect to the copolymer of 5 to 90 mol% of (meth) acrylate and 10 to 95 mol% of other radical polymerizable monomer Examples thereof include a resin obtained by adding a monobasic acid, or an alkali-soluble resin obtained by adding a polybasic acid anhydride to 10 to 100 mol% of a hydroxyl group generated by the addition reaction.

  Examples of the epoxy group-containing (meth) acrylate include glycidyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, (3,4-epoxycyclohexyl) methyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. ) Acrylate glycidyl ether and the like. Of these, glycidyl (meth) acrylate is preferred. These epoxy group-containing (meth) acrylates may be used alone or in combination of two or more.

  The other radical polymerizable monomer copolymerized with the epoxy group-containing (meth) acrylate is not particularly limited as long as the effects of the present invention are not impaired. For example, vinyl aromatics, dienes, (meth) Examples include acrylic acid esters, (meth) acrylic acid amides, vinyl compounds, unsaturated dicarboxylic acid diesters, monomaleimides, and the like, and in particular, mono (meth) having a structure represented by the following formula (7) Acrylate is preferred.

  The repeating unit derived from the mono (meth) acrylate having the structure represented by the following formula (7) contains 5 to 90 mol% among the repeating units derived from “other radical polymerizable monomers”. The content is preferably 10 to 70 mol%, more preferably 15 to 50 mol%.

In the above formula (7), R ⁸⁹ represents a hydrogen atom or a methyl group, and R ⁹⁰ represents a structure represented by the following formula (8).

The formula ^{(8), R} 91 ~R ⁹⁸ independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ⁹⁶ and R ⁹⁸ may be connected to each other to form a ring.
The ring formed by connecting R ⁹⁶ and R ⁹⁸ is preferably an aliphatic ring, may be saturated or unsaturated, and preferably has 5 to 6 carbon atoms.
Among these, among the structures represented by the formula (8), those represented by the following structural formulas (8a), (8b), or (8c) are particularly preferable.

In addition, the mono (meth) acrylate which has a structure represented by the said Formula (8) may be used individually by 1 type, and may use 2 or more types together.
As "other radical polymerizable monomers" other than the mono (meth) acrylate having the structure represented by the formula (8), styrene, in that the heat resistance and strength of the obtained pixel can be improved. (Meth) acrylic acid-n-butyl, (meth) acrylic acid-tert-butyl, (meth) acrylic acid cyclohexyl, (meth) acrylic acid isobornyl, (meth) acrylic acid adamantyl, (meth) acrylic acid benzyl, (meta ) -2-hydroxyethyl acrylate, N-phenylmaleimide, N-cyclohexylmaleimide.

The content of the repeating unit derived from at least one selected from the above monomer group is preferably 1 to 70 mol%, more preferably 3 to 50 mol%.
A known solution polymerization method is applied to the copolymerization reaction between the epoxy group-containing (meth) acrylate and the other radical polymerizable monomer.
In the present invention, as a copolymer of the epoxy group-containing (meth) acrylate and the other radical polymerizable monomer, 5 to 90 mol% of repeating units derived from the epoxy group-containing (meth) acrylate, and others Is preferably composed of 10 to 95 mol% of repeating units derived from the radically polymerizable monomer, more preferably composed of 20 to 80 mol% of the former and 80 to 20 mol% of the latter. What consists of 70 mol% and the latter 70-30 mol% is especially preferable.

Within the above range, the addition amount of the polymerizable component and alkali-soluble component described later is sufficient, and the heat resistance and the strength of the film are sufficient, which is preferable.
The epoxy group portion of the epoxy group-containing copolymer synthesized as described above is reacted with an unsaturated monobasic acid (polymerizable component) and a polybasic acid anhydride (alkali-soluble component).
Here, as an unsaturated monobasic acid added to an epoxy group, a well-known thing can be used, For example, unsaturated carboxylic acid which has an ethylenically unsaturated double bond is mentioned.

Specific examples include (meth) acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, α-position substituted with a haloalkyl group, an alkoxyl group, a halogen atom, a nitro group, or a cyano group. And monocarboxylic acids such as (meth) acrylic acid. Of these, (meth) acrylic acid is preferred. These may be used alone or in combination of two or more.

By adding such components, polymerizability can be imparted to the binder resin used in the present invention.
These unsaturated monobasic acids are usually added to 10 to 100 mol% of the epoxy group of the copolymer, preferably 30 to 100 mol%, more preferably 50 to 100 mol%. It is preferable for it to be in the above range since the colored resin composition is excellent in stability over time. In addition, a well-known method is employable as a method of adding unsaturated monobasic acid to the epoxy group of a copolymer.

Furthermore, a well-known thing can be used as a polybasic acid anhydride added to the hydroxyl group produced when an unsaturated monobasic acid is added to the epoxy group of a copolymer.
For example, dibasic acid anhydrides such as maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, chlorendic anhydride; trimellitic anhydride, pyromellitic anhydride, benzophenone Examples thereof include anhydrides of three or more bases such as tetracarboxylic acid anhydride and biphenyltetracarboxylic acid anhydride. Of these, succinic anhydride and tetrahydrophthalic anhydride are preferred. These polybasic acid anhydrides may be used individually by 1 type, and may use 2 or more types together.

By adding such a component, alkali solubility can be imparted to the binder resin used in the present invention.
These polybasic acid anhydrides are usually added to 10 to 100 mol% of the hydroxyl group generated by adding an unsaturated monobasic acid to the epoxy group of the copolymer, preferably 20 to 90 mol. %, More preferably 30 to 80 mol%.

Within the above range, the remaining film ratio and solubility during development are sufficient, which is preferable.
In addition, a well-known method is employable as a method of adding a polybasic acid anhydride to the said hydroxyl group.
Furthermore, in order to improve photosensitivity, after adding the above-mentioned polybasic acid anhydride, glycidyl (meth) acrylate or a glycidyl ether compound having a polymerizable unsaturated group is added to a part of the generated carboxyl group. May be. Such a resin structure is described in, for example, Japanese Patent Application Laid-Open Nos. 8-297366 and 2001-89533.

The polystyrene-reduced weight average molecular weight (Mw) of the above-described binder resin (C-1) measured by GPC (gel permeation chromatography) is preferably 3000 to 100,000, and particularly preferably 5000 to 50000. Within the above range, heat resistance, film strength, and solubility in a developer are preferable.
Moreover, as a standard of molecular weight distribution, the ratio of weight average molecular weight (Mw) / number average molecular weight (Mn) is preferably 2.0 to 5.0.

In addition, the acid value of binder resin (C-1) is 10-200 mg-KOH / g normally, Preferably it is 15-150 mg-KOH / g, More preferably, it is 25-100 mg-KOH / g. If the acid value is too low, the solubility in the developer may be reduced. Conversely, if it is too high, film roughening may occur.
Content of (C) binder resin in a colored resin composition is 0.1 to 80 weight% normally in a total solid, Preferably it is 1 to 60 weight%.
Within the above range, the adhesion to the substrate is good, the permeability of the developer to the exposed area is moderate, and the surface smoothness and sensitivity of the pixels are good.

[(B) Solvent]
The colored resin composition of the present invention contains (B) a solvent. The solvent has a function of dissolving or dispersing each component contained in the colored resin composition and adjusting the viscosity.
The solvent (B) may be any solvent as long as it can dissolve or disperse each component constituting the colored resin composition, and a solvent having a boiling point in the range of 100 to 200 ° C. is preferably selected. More preferably, it has a boiling point of 120-170 ° C.
Examples of such solvents include the following.

  Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether (PGME), propylene glycol-mono t-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, methoxymethyl pen Glycol monoalkyl ethers such as butanol, propylene glycol monoethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, 3-methyl-3-methoxybutanol, tripropylene glycol monomethyl ether;

Glycol dialkyl ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether;
Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, 3-methoxybutyl acetate, methoxypentyl acetate, Glycol alkyl ether acetates such as diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether acetate, 3-methyl-3-methoxybutyl acetate;

Ethers such as diethyl ether, dipropyl ether, diisopropyl ether, diamyl ether, ethyl isobutyl ether, dihexyl ether;
Ketones such as acetone, methyl ethyl ketone, methyl amyl ketone, methyl isopropyl ketone, methyl isoamyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl amyl ketone, methyl butyl ketone, methyl hexyl ketone, methyl nonyl ketone;
Mono- or polyhydric alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, glycerin;

aliphatic hydrocarbons such as n-pentane, n-octane, diisobutylene, n-hexane, hexene, isoprene, dipentene, dodecane;
Cycloaliphatic hydrocarbons such as cyclohexane, methylcyclohexane, methylcyclohexene, bicyclohexyl;
Aromatic hydrocarbons such as benzene, toluene, xylene, cumene;
Amyl formate, ethyl formate, ethyl acetate, butyl acetate, propyl acetate, amyl acetate, methyl isobutyrate, ethylene glycol acetate, ethyl propionate, propyl propionate, butyl butyrate, isobutyl butyrate, methyl isobutyrate, ethyl Caprylate, butyl stearate, ethyl benzoate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, 3-methoxypropionic acid Linear or cyclic esters such as butyl, γ-butyrolactone;

Alkoxycarboxylic acids such as 3-methoxypropionic acid and 3-ethoxypropionic acid;
Halogenated hydrocarbons such as butyl chloride and amyl chloride;
Ether ketones such as methoxymethylpentanone;
Examples of commercially available solvents corresponding to the above include mineral spirit, carbitol, ethyl carbitol, butyl carbitol, methyl cellosolve, ethyl cellosolve, ethyl cellosolve acetate, methyl cellosolve acetate, diglyme (all trade names).

These solvents may be used alone or in combination of two or more.
Among the above solvents, glycol monoalkyl ethers are preferred from the viewpoint of the solubility of the dye (A) according to the present invention. Among these, propylene glycol monomethyl ether is particularly preferable from the viewpoint of the solubility of various components in the composition.
Further, for example, when a pigment (F), which will be described later, is included as an optional component, the balance of coating properties, surface tension, etc. is good, and from the viewpoint that the solubility of the constituent components in the composition is relatively high, glycolalkyl is further used as a solvent. It is more preferable to use a mixture of ether acetates. In a composition containing a pigment, glycol monoalkyl ethers have a high polarity, tend to aggregate the pigment, and may reduce storage stability such as increasing the viscosity of the colored resin composition. For this reason, it is preferable that the amount of the glycol monoalkyl ether used is not excessively large, and the proportion of the glycol monoalkyl ether in the solvent (B) is preferably 5 to 50% by weight, more preferably 5 to 30% by weight. .

In the colored resin composition of the present invention, the (B) solvent preferably contains a polar organic solvent, particularly in that the compound (II) is dissolved well.
Aprotic polar organic solvents are preferred, for example, acetone, tetrahydrofuran, acetonitrile, N, N-dimethylformamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone, etc., among which N-methyl-2-pyrrolidone is particularly preferred. .

The aprotic polar organic solvent is preferably contained in a total amount of 0.1% by weight or more, preferably 1% by weight or more, and usually 20% by weight or less, preferably 10% by weight or less.
It is preferable for it to be within the above range since the viscosity of the colored resin composition hardly changes with time.
Further, from the viewpoint of suitability for a slit coat method corresponding to a recent large substrate or the like, it is also preferable to use a solvent having a boiling point of 150 ° C. or higher. In this case, the content of such a high boiling point solvent is preferably 3 to 50% by weight, more preferably 5 to 40% by weight, and particularly preferably 5 to 30% by weight based on the total amount of the solvent (B). If the amount of the high boiling point solvent is too small, for example, a dye component may precipitate and solidify at the tip of the slit nozzle to cause foreign matter defects, and if it is too large, the drying speed of the composition will be slowed down. There is a concern that the filter manufacturing process may cause problems such as tact defects in the vacuum drying process and pin marks of prebaking.

The solvent having a boiling point of 150 ° C. or higher may be glycol alkyl ether acetates or glycol alkyl ethers. In this case, a solvent having a boiling point of 150 ° C. or higher may not be included separately. .
The colored resin composition of the present invention may be used for color filter production by the ink jet method, but in color filter production by the ink jet method, the ink emitted from the nozzle is very small, from several to several tens pL, There is a tendency for the solvent to evaporate and the ink to concentrate and dry before landing on the periphery of the nozzle opening or in the pixel bank. In order to avoid this, it is preferable that the solvent has a high boiling point. Specifically, it is preferable that the solvent (B) contains a solvent having a boiling point of 180 ° C. or higher. In particular, it is preferable to contain a solvent having a boiling point of 200 ° C. or higher, particularly 220 ° C. or higher. Moreover, it is preferable that the high boiling point solvent whose boiling point is 180 degreeC or more is 50 weight% or more in (B) solvent. When the ratio of such a high boiling point solvent is less than 50% by weight, the effect of preventing evaporation of the solvent from the ink droplets may not be sufficiently exhibited.

  In the colored resin composition of the present invention, the content of the (B) solvent is not particularly limited, but the upper limit is usually 99% by weight. When the content of the (B) solvent in the composition exceeds 99% by weight, the concentration of each component excluding the (B) solvent becomes too small and may be inappropriate for forming a coating film. . On the other hand, the lower limit of the content of the solvent (B) is usually 75% by weight, preferably 80% by weight, and more preferably 82% by weight in consideration of viscosity suitable for coating.

[(D) Polymerizable monomer]
The colored resin composition of the present invention preferably contains (D) a polymerizable monomer.
(D) The polymerizable monomer is not particularly limited as long as it is a polymerizable low-molecular compound, but it may be an addition-polymerizable compound having at least one ethylenic double bond (hereinafter referred to as “ethylenic compound”). Is preferred).

The ethylenic compound is a compound having an ethylenic double bond that undergoes addition polymerization and cures by the action of a photopolymerization initiation component described later when the colored resin composition of the present invention is irradiated with actinic rays. In addition, the (D) polymerizable monomer in this invention means the concept opposite to what is called a polymeric substance, and also includes a dimer, a trimer, and an oligomer other than a monomer in a narrow sense.
(D) Examples of the ethylenic compound in the polymerizable monomer include unsaturated carboxylic acids such as (meth) acrylic acid; esters of monohydroxy compounds and unsaturated carboxylic acids; aliphatic polyhydroxy compounds and unsaturated carboxylic acids; Esters of aromatic polyhydroxy compounds and unsaturated carboxylic acids; Esterification of unsaturated carboxylic acids with polyvalent carboxylic acids and polyhydric hydroxy compounds such as aliphatic polyhydroxy compounds and aromatic polyhydroxy compounds described above An ester obtained by the reaction; an ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound and a (meth) acryloyl group-containing hydroxy compound;

  Esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids include ethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate , Pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) Examples include (meth) acrylic acid esters such as acrylate and glycerol (meth) acrylate. In addition, the (meth) acrylic acid portion of these (meth) acrylic acid esters is replaced with an itaconic acid portion, a crotonic acid portion replaced with a crotonic acid portion, or a maleic acid ester replaced with a maleic acid portion Is mentioned.

Examples of the ester of an aromatic polyhydroxy compound and an unsaturated carboxylic acid include hydroquinone di (meth) acrylate, resorcin di (meth) acrylate, pyrogallol tri (meth) acrylate, and the like.
The ester obtained by the esterification reaction of an unsaturated carboxylic acid with a polyvalent carboxylic acid and a polyvalent hydroxy compound may be a single substance or a mixture. Representative examples are condensates of (meth) acrylic acid, phthalic acid, and ethylene glycol; condensates of (meth) acrylic acid, maleic acid, and diethylene glycol; condensation of (meth) acrylic acid, terephthalic acid, and pentaerythritol A condensate of (meth) acrylic acid, adipic acid, butanediol, and glycerin.

  Examples of the ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound and a (meth) acryloyl group-containing hydroxy compound include aliphatic diisocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; alicyclic rings such as cyclohexane diisocyanate and isophorone diisocyanate. Formula diisocyanates; aromatic diisocyanates such as tolylene diisocyanate and diphenylmethane diisocyanate, and (meth) acryloyl such as 2-hydroxyethyl (meth) acrylate and 3-hydroxy [1,1,1-tri (meth) acryloyloxymethyl] propane A reaction product with a group-containing hydroxy compound is exemplified.

In addition, examples of the ethylenic compound used in the present invention include (meth) acrylamides such as ethylene bis (meth) acrylamide; allyl esters such as diallyl phthalate; vinyl group-containing compounds such as divinyl phthalate. .
Among these, esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids are preferred, pentaerythritol or (meth) acrylic acid esters of dipentaerythritol are more preferred, and dipentaerythritol hexa (meth) acrylate is particularly preferred.

  The ethylenic compound may be a monomer having an acid value. The monomer having an acid value is, for example, an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, and a non-aromatic carboxylic acid anhydride is reacted with an unreacted hydroxyl group of the aliphatic polyhydroxy compound. A polyfunctional monomer having a group is preferable, and in this ester, the aliphatic polyhydroxy compound is pentaerythritol and / or dipentaerythritol.

These monomers may be used alone, but since it is difficult to obtain a single compound in production, a mixture of two or more kinds may be used.
Moreover, you may use together the polyfunctional monomer which does not have an acid group, and the polyfunctional monomer which has an acid group as (D) polymeric monomer as needed.
A preferable acid value of the polyfunctional monomer having an acid group is 0.1 to 40 mg-KOH / g, and particularly preferably 5 to 30 mg-KOH / g.

When it is within the above range, the development and dissolution characteristics are hardly lowered, and the production and handling are easy. Furthermore, it is preferable because the photopolymerization performance is hardly lowered and the curability such as the surface smoothness of the pixel is good.
In the present invention, a more preferred polyfunctional monomer having an acid group is, for example, a mixture containing succinic acid ester of dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentaacrylate as a main component. It is also possible to use this polyfunctional monomer in combination with another polyfunctional monomer.

In the colored resin composition of the present invention, the content of the polymerizable monomer (D) is usually 1% by weight or more, preferably 5% by weight or more, more preferably 10% by weight or more in the total solid content. Further, it is usually 80% by weight or less, preferably 70% by weight or less, more preferably 50% by weight or less, and particularly preferably 40% by weight or less.
The ratio of the (D) polymerizable monomer to the (A) dye is usually 1% by weight or more, preferably 5% by weight or more, more preferably 10% by weight or more, and particularly preferably 20% by weight or more. The amount is usually 200% by weight or less, preferably 100% by weight or less, and more preferably 80% by weight or less.

Within the above range, photocuring is appropriate, poor adhesion during development is difficult to place, the cross-section after development is difficult to reverse taper, and further, peeling phenomenon and omission failure due to lower solubility are difficult to place. preferable.
[(E) Photopolymerization initiation component and / or thermal polymerization initiation component]
The colored resin composition of the present invention preferably contains (E) a photopolymerization initiation component and / or a thermal polymerization initiation component for the purpose of curing the coating film. However, the curing method may be other than those using these initiators.

  In particular, when the colored resin composition of the present invention includes a resin having an ethylenic double bond as the component (C), or includes an ethylenic compound as the component (D), it directly absorbs light, or It is preferable to contain a photopolymerization initiating component that has a function of generating a polymerization active radical and / or a thermal polymerization initiating component that generates a polymerization active radical by heat. In the present invention, the component (E) as a photopolymerization initiation component refers to a photopolymerization initiator (hereinafter also referred to as “(E1) component”), a polymerization accelerator (hereinafter, optionally referred to as “(E2) component”). ")" And a sensitizing dye (hereinafter also referred to as "(E3) component").

[(E) Photopolymerization initiation component]
You may contain in the colored resin composition of this invention. The photopolymerization initiating component is usually used as a mixture of (E1) a photopolymerization initiator, and (E2) a polymerization accelerator and (E3) an additive such as a sensitizing dye, which are added as necessary. It is a component having a function of generating a polymerization active radical by directly absorbing or photosensitizing to cause a decomposition reaction or a hydrogen abstraction reaction.

  Examples of (E1) photopolymerization initiator constituting the photopolymerization initiating component include titanocene derivatives described in JP-A Nos. 59-152396 and 61-151197, etc .; JP-A-10-300922 Hexaarylbiimidazole derivatives described in JP-A-11-174224, JP-A-2000-56118, etc .; halomethylated oxadiazole derivatives described in JP-A-10-39503, etc., halomethyl-s -Radical activators such as triazine derivatives, N-aryl-α-amino acids such as N-phenylglycine, N-aryl-α-amino acid salts, N-aryl-α-amino acid esters, α-aminoalkylphenone derivatives And oxime ester derivatives described in JP-A No. 2000-80068 and the like.

Specific examples include photopolymerization initiators described in International Publication No. 2009/107734 pamphlet and the like.
Among these photopolymerization initiators, α-aminoalkylphenone derivatives, oxime ester derivatives, biimidazole derivatives, acetophenone derivatives, and thioxanthone derivatives are more preferable.

  The oxime ester derivatives include 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (o-benzoyloxime), ethanone, 1- [9-ethyl-6- ( 2-methylbenzoyl) -9H-carbazol-3-yl], 1- (o-acetyloxime), and a compound represented by the following formula (XI).

(In formula (XI), R ¹⁰¹ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 25 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a heteroaryl group having 4 to 25 carbon atoms. An alkyl group, each of which may have a substituent, or R ¹⁰¹ may be bonded to X or Z to form a ring;
R ¹⁰² represents an alkanoyl group having 2 to 20 carbon atoms, an alkenoyl group having 3 to 25 carbon atoms, a cycloalkanoyl group having 4 to 8 carbon atoms, an aryloyl group having 7 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 10 carbon atoms. , An aryloxycarbonyl group having 7 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a heteroaryloyl group having 3 to 20 carbon atoms, or an alkylaminocarbonyl group having 2 to 20 carbon atoms, It may have a substituent.

X represents a divalent aromatic hydrocarbon ring group and / or an aromatic hetero group formed by condensation of two or more rings which may have a substituent.
Z represents an aromatic group which may have a substituent. )
Of the compounds represented by the formula (XI), compounds in which X is a carbazole ring which may have a substituent are preferable. Specifically, compounds represented by the following formula (XII) Among them, the compound represented by the following formula (XIII) is particularly preferable.

(In the formula, R ¹⁰¹ , R ¹⁰² and Z have the same meanings as in formula (XI). R ^{10
3 to} R ¹⁰⁹ each independently represent a hydrogen atom or an arbitrary substituent. )

(In the formula, R ^101a represents an alkyl group having 1 to 3 carbon atoms or a group represented by the following formula (XIIIa).

(Wherein R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a phenyl group or an N-acetyl-N-acetoxyamino group.
* Represents a binding site. )
R ^102a represents an alkanoyl group having 2 to 4 carbon atoms, and X ^a represents a 3,6-carbazolyl group in which the nitrogen atom may be substituted with an alkyl group having 1 to 4 carbon atoms. Za represents ^a phenyl group which may be substituted with an alkyl group or a naphthyl group which may be substituted with a morpholino group. )
In addition, benzoin alkyl ethers, anthraquinone derivatives; acetophenone derivatives such as 2-methyl- (4′-methylthiophenyl) -2-morpholino-1-propanone, 2-ethylthioxanthone, 2,4-diethylthioxanthone, etc. Examples also include thioxanthone derivatives, benzoate derivatives, acridine derivatives, phenazine derivatives, anthrone derivatives and the like.

Among these photopolymerization initiators, α-aminoalkylphenone derivatives, thioxanthone derivatives, and oxime ester derivatives are more preferable. In particular, oxime ester derivatives are preferable.
Examples of the (E2) polymerization accelerator used as necessary include N, N-dialkylaminobenzoic acid alkyl esters such as N, N-dimethylaminobenzoic acid ethyl ester; 2-mercaptobenzothiazole, 2-mercapto Examples thereof include mercapto compounds having a heterocyclic ring such as benzoxazole and 2-mercaptobenzimidazole; mercapto compounds such as aliphatic polyfunctional mercapto compounds.

Each of these (E1) photopolymerization initiator and (E2) polymerization accelerator may be used alone or in combination of two or more.
Further, (E3) sensitizing dye is used for the purpose of increasing the sensitivity as required. As the sensitizing dye, an appropriate one is used according to the wavelength of the image exposure light source. For example, xanthene dyes described in JP-A-4-221958 and JP-A-4-219756; No. 239703, JP-A-5-289335, etc. Coumarin dyes having a heterocyclic ring; JP-A-3-239703, JP-A-5-289335, etc .; 3-ketocoumarin dyes; Pyrromethene dyes described in JP-A-6-19240 and the like;
-2528, JP 54-155292, JP-B 45-37377, JP 48-84183, JP 52-112681, JP 58-15503, JP 60-88005 JP-A-59-56403, JP-A-2-69, JP-A-57-168088, JP-A-5-107761, JP-A-5-210240, JP-A-4-288818, etc. And dyes having a dialkylaminobenzene skeleton.

(E3) A sensitizing dye may also be used alone or in combination of two or more.
In the colored resin composition of the present invention, the content of these (E) photopolymerization initiating components is usually 0.1% by weight or more, preferably 0.2% by weight or more, more preferably 0.8% by weight in the total solid content. It is 5% by weight or more, usually 40% by weight or less, preferably 30% by weight or less, and more preferably 20% by weight or less.

Within the above range, the sensitivity to the exposure light beam is good, the solubility of the unexposed part in the development station is good, and it is preferable in that it is difficult to induce poor development.
(Thermal polymerization initiation component)
Specific examples of the thermal polymerization initiation component that may be contained in the colored resin composition of the present invention include azo compounds, organic peroxides, hydrogen peroxide, and the like. Of these, azo compounds are preferably used. More specifically, for example, a thermal polymerization initiating component described in International Publication No. 2009/107734 can be used.

These thermal polymerization initiating components may be used alone or in combination of two or more.
[Other optional ingredients]
In addition to the above components, the colored resin composition of the present invention comprises a surfactant, an organic carboxylic acid and / or an organic carboxylic acid anhydride, a thermosetting compound, a plasticizer, a thermal polymerization inhibitor, a storage stabilizer, a surface It may contain a protective agent, an adhesion improver, a development improver, and the like. Moreover, when it contains the below-mentioned (F) pigment, you may contain a dispersing agent and a dispersing aid. As these optional components, for example, various compounds described in JP-A-2007-113000 can be used.

<(F) Pigment>
The colored resin composition of the present invention may contain (F) a pigment within a range not impairing the effects of the present invention for the purpose of improving the heat resistance of the obtained color filter.
(F) As a pigment, for example, when forming a pixel of a color filter, pigments of various colors such as blue and purple can be used. Examples of the chemical structure include organic pigments such as phthalocyanine, quinacridone, benzimidazolone, dioxazine, indanthrene, and perylene. In addition, various inorganic pigments can be used. Hereinafter, specific examples of usable pigments are indicated by pigment numbers.

  Examples of blue pigments include C.I. I. Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56: 1, 60, 61, 61: 1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like.

Among these, a blue copper phthalocyanine pigment is preferable, and examples of the copper phthalocyanine pigment include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6 and the like are preferable, and C.I. I. Pigment Blue 15: 6.
For this reason, when the colored resin composition of this invention contains a blue pigment, it is 80 weight% or more with respect to the total content of a blue pigment, Especially 90 weight% or more, Especially 95-100 weight% is C.I. I. Pigment Blue 15: 6 is preferable.

Examples of purple pigments include C.I. I. Pigment Violet 1, 1: 1, 2, 2: 2, 3, 3: 1, 3: 3, 5, 5: 1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50 and the like.
Among these, a purple dioxazine pigment is preferable, and as the dioxazine pigment, C.I. I. Pigment Violet 19 and 23 are preferable, and C.I. I. Pigment Violet 23.

For this reason, when the colored resin composition of this invention contains a purple pigment, it is 80 weight% or more with respect to the total content of a purple pigment, Especially 90 weight% or more, Especially 95-100 weight% is C.I. I. Pigment Violet 23 is preferable.
These may be used alone or in a combination of two or more in any combination and ratio.

The (F) pigment used in the colored resin composition of the present invention preferably has a small average primary particle diameter from the viewpoint of forming a high-contrast pixel. Specifically, the average primary particle diameter is 40 nm or less. Is preferable, and it is more preferable that it is 35 nm or less.
Particularly for the blue copper phthalocyanine pigment, the average primary particle size is preferably 40 nm or less, more preferably 35 nm or less, and still more preferably 20 to 30 nm.

Moreover, about a dioxazine pigment, an average primary particle diameter becomes like this. Preferably it is 40 nm or less, More preferably, it is 25-35 nm. From the viewpoint that the pigment is less likely to aggregate in the colored resin composition, it is preferable that the average primary particle size is not too small.
Here, the average primary particle size of the (F) pigment is a value measured and calculated by the following method.

  First, (F) a pigment is ultrasonically dispersed in chloroform, dropped onto a collodion film-attached mesh, dried, and a primary particle image of the pigment is obtained by observation with a transmission electron microscope (TEM). From this image, the particle size of each pigment particle is determined for a plurality of (usually about 200 to 300) pigment particles, with the diameter corresponding to the area circle converted to the diameter of a circle having the same area.

Using the obtained primary particle size value, the number average value is calculated according to the following formula to obtain the average particle size.
The particle diameter of each pigment _{particle: X 1, X 2, X} 3, X 4, ····, X i, ······ X m

{Blending amount}
In the present invention, when the pigment (F) is contained, the content of the pigment in the colored resin composition is usually 80% by weight or less, preferably 50% by weight or less in the total solid content.
Moreover, content with respect to 100 weight part of said (A) dye is 2000 weight part or less normally, Preferably it is 1000 weight part or less.

By setting it within the above-mentioned range, (A) it is preferable in that heat resistance is easily improved without greatly affecting the transmittance of the dye.
[Dispersant]
When the colored resin composition of the present invention contains (F) a pigment, it is preferable to further contain a dispersant.

The dispersant in the present invention is not particularly limited as long as the pigment is dispersed and can maintain stability.
For example, cationic, anionic, nonionic or amphoteric dispersants can be used, but polymer dispersants are preferred. Specific examples include block copolymers, polyurethanes, polyesters, alkylammonium salts or phosphate esters of polymer copolymers, and cationic comb graft polymers. Of these dispersants, block copolymers, polyurethanes, and cationic comb graft polymers are preferred. In particular, a block copolymer is preferable, and among these, a block copolymer composed of an A block having solvophilicity and a B block having a functional group containing a nitrogen atom is preferable.

Specifically, the B block having a nitrogen atom-containing functional group includes a unit structure having a quaternary ammonium base and / or an amino group in the side chain, while the solvophilic A block includes a quaternary ammonium. Examples include a unit structure having no base and amino group.
The B block constituting the acrylic block copolymer has a unit structure having a quaternary ammonium base and / or an amino group, and has a pigment adsorption function.

Further, when the B block has a quaternary ammonium base, the quaternary ammonium base may be directly bonded to the main chain, but may be bonded to the main chain via a divalent linking group. Good.
Examples of such block copolymers include those described in JP-A-2009-025813.

Moreover, the colored resin composition of the present invention may contain a dispersant other than those described above. Examples of other dispersants include those described in JP-A-2006-343648, for example.
When the colored resin composition of the present invention contains (F) a pigment, the content of the dispersant in the total solid content is 2 to 1000% by weight, particularly 5 to 500% by weight of the total content of (F) pigment. %, Particularly 10 to 250% by weight.

By setting it within the above range, (A) it is preferable in that good pigment dispersibility can be ensured without affecting the heat resistance of the dye, and the pigment dispersion stability becomes better.
[Preparation Method of Colored Resin Composition]
In the present invention, the colored resin composition can be prepared by an appropriate method. For example, (A) a dye and (C) a binder resin are mixed together with (B) a solvent and optional components used as necessary. Can be prepared.

  In addition, as a preparation method in the case of containing (F) a pigment, (F) a pigment containing (A) dye may be added in a solvent in the presence of a dispersing agent and a dispersing aid if necessary (C ) A color dispersion is prepared by mixing and dispersing together with a part of the binder resin, for example, using a paint shaker, sand grinder, ball mill, roll mill, stone mill, jet mill, homogenizer and the like. (A) a dye, (C) a binder resin, and (D) a polymerizable monomer, (E) a photopolymerization initiating component and / or a thermal polymerization initiating component, etc. are added to the colored dispersion and mixed. The method of preparing by doing can be mentioned.

[Application of colored resin composition]
The colored resin composition of the present invention is usually in a state where all the constituent components are dissolved or dispersed in a solvent. Such a colored resin composition is supplied onto a substrate to form components such as a color filter, a liquid crystal display device, and an organic EL display device.
The colored resin composition of the present invention is particularly preferably used for forming a pixel of a color filter. That is, the colored resin composition of the present invention is preferably a colored resin composition for color filters.

Hereinafter, as an application example of the colored resin composition of the present invention, an application as a pixel of a color filter and a liquid crystal display device (panel) and an organic EL display device having them will be described.
<Color filter>
The color filter of the present invention has a pixel formed from the colored resin composition of the present invention.

The method for forming the color filter of the present invention will be described below.
The pixel of the color filter can be formed by various methods. Here, although the case where it forms by the photolithographic method using a photopolymerizable colored resin composition is demonstrated to an example, a manufacturing method is not limited to this.
First, on the surface of the substrate, if necessary, a black matrix is formed so as to partition a portion for forming pixels, and after applying the colored resin composition of the present invention on this substrate, pre-baking is performed. The solvent is evaporated to form a coating film. Then, after exposing this coating film through a photomask, developing with an alkali developer, dissolving and removing the unexposed portion of the coating film, and then post-baking, each of red, green, and blue A color filter can be manufactured by forming a pixel pattern.

The substrate used for forming the pixels is not particularly limited as long as it is transparent and has an appropriate strength. For example, polyester resin, polyolefin resin, polycarbonate resin, acrylic resin, thermoplastic resin Examples thereof include a sheet made, an epoxy resin, a thermosetting resin, and various glasses.
In addition, these substrates may be appropriately subjected to pretreatment as desired, such as thin film formation treatment with a silane coupling agent or urethane resin, surface treatment such as corona discharge treatment or ozone treatment, if desired.

When applying the colored resin composition to the substrate, a spinner method, a wire bar method, a flow coating method, a slit and spin method, a die coating method, a roll coating method, a spray coating method, and the like can be given. Of these, the slit and spin method and the die coating method are preferable.
The thickness of the coating film is usually 0.2 to 20 μm, preferably 0.5 to 10 μm, particularly preferably 0.8 to 5.0 μm as the film thickness after drying.

Within the above range, it is preferable in that the gap can be easily adjusted in the pattern development or liquid crystal cell forming step, and a desired color can be easily expressed.
As the radiation used in the exposure, for example, visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray or the like can be used, and radiation having a wavelength in the range of 190 to 450 nm is preferable.

  A light source for using radiation having a wavelength of 190 to 450 nm used for image exposure is not particularly limited. For example, a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, Lamp light sources such as medium pressure mercury lamp, low pressure mercury lamp, carbon arc, fluorescent lamp; laser light sources such as argon ion laser, YAG laser, excimer laser, nitrogen laser, helium cadmium laser, semiconductor laser, and the like. An optical filter can also be used when used by irradiating light of a specific wavelength.

Exposure of radiation, 10~10,000J / ^{m 2} is preferred.
Examples of the alkaline developer include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium silicate, potassium silicate, sodium metasilicate, sodium phosphate, Inorganic alkaline compounds such as potassium phosphate, sodium hydrogen phosphate, potassium hydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, ammonium hydroxide; mono-di- or tri-ethanolamine, mono-di-, or tri -Methylamine, mono-, di-, or tri-ethylamine, mono-, or di-isopropylamine, n-butylamine, mono-, di-, or tri-isopropanolamine, ethyleneimine, ethylenediimine, tetramethylammonium Hydroxide (TMAH) Aqueous solution of an organic alkaline compound choline are preferred.

An appropriate amount of a water-soluble organic solvent such as isopropyl alcohol, benzyl alcohol, ethyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol, diacetone alcohol, or the like can be added to the alkali developer. In addition, it is usually washed with water after alkali development.
As the development processing method, any method such as an immersion development method, a spray development method, a brush development method, and an ultrasonic development method can be used. The development conditions are preferably 5 to 300 seconds at room temperature (23 ° C.).

There are no particular restrictions on the conditions of the development processing, but the development temperature is usually 10 ° C. or higher, especially 15 ° C. or higher, more preferably 20 ° C. or higher, and usually 50 ° C. or lower, especially 45 ° C. or lower, further 40 ° C. or lower. Is preferred.
The developing method can be any one of immersion developing method, spray developing method, brush developing method, ultrasonic developing method and the like.

  When the color filter thus produced is used in a liquid crystal display device, a transparent electrode such as ITO is formed on the image as it is, and is used as a part of a component such as a color display or a liquid crystal display device. Although used, in order to improve surface smoothness and durability, a top coat layer such as polyamide or polyimide can be provided on the image as necessary. Further, in some applications such as a planar alignment type drive system (IPS mode), the transparent electrode may not be formed. In the vertical alignment type driving method (MVA mode), ribs may be formed. Further, a column structure (photo spacer) by a photolithography method may be formed instead of the bead dispersion type spacer.

<Liquid crystal display device>
The liquid crystal display device of the present invention uses the above-described color filter of the present invention. There is no restriction | limiting in particular about the model and structure of the liquid crystal display device of this invention, It can assemble according to a conventional method using the color filter of this invention.
For example, the liquid crystal display device of the present invention can be formed by the method described in “Liquid Crystal Device Handbook” (Nikkan Kogyo Shimbun, September 29, 1989, Japan Society for the Promotion of Science 142nd Committee).

<Organic EL display device>
When producing an organic EL display device having the color filter of the present invention, for example, as shown in FIG. 1, on a blue color filter in which pixels 20 are formed on a transparent support substrate 10 by the colored resin composition of the present invention. A multicolor organic EL element is manufactured by laminating the organic light-emitting body 500 through the organic protective layer 30 and the inorganic oxide film 40.

  As a method for laminating the organic light emitter 500, a transparent anode 50, a hole injection layer 51, a hole transport layer 52, a light emitting layer 53, an electron injection layer 54, and a cathode 55 are sequentially formed on the upper surface of the color filter. For example, a method of adhering the organic light-emitting body 500 formed on another substrate onto the inorganic oxide film 40 can be used. The organic EL element 100 manufactured as described above can be applied to both a passive drive type organic EL display device and an active drive type organic EL display device.

EXAMPLES Next, although an Example demonstrates this invention further more concretely, this invention is not limited to description of a following example, unless the summary is exceeded.
(Reference Synthesis Example 1: Synthesis of Resin A)
145 parts by weight of propylene glycol monomethyl ether acetate was stirred while replacing with nitrogen, and the temperature was raised to 120 ° C. 20 parts by weight of styrene, 57 parts by weight of glycidyl methacrylate and 82 parts by weight of monoacrylate having a tricyclodecane skeleton (FA-513M manufactured by Hitachi Chemical Co., Ltd.) were added dropwise thereto, and the mixture was further stirred at 120 ° C. for 2 hours. Next, the inside of the reaction vessel was changed to air substitution, 0.7 parts by weight of trisdimethylaminomethylphenol and 0.12 parts by weight of hydroquinone were added to 27 parts by weight of acrylic acid, and the reaction was continued at 120 ° C. for 6 hours. Then, 52 parts by weight of tetrahydrophthalic anhydride (THPA) and 0.7 parts by weight of triethylamine were added and reacted at 120 ° C. for 3.5 hours. The weight average molecular weight Mw measured by GPC of the resin A thus obtained was about 15000. The structure of Resin A was as shown below (polymer compound containing the following four types of repeating units).

(Reference Synthesis Example 2: Synthesis of Dye A)

Reaction 1: A solution of compound 1 (10 g) in N, N-dimethylformamide (100 ml) was cooled in an ice bath, sodium hydride (60%, 4.3 g) was added, and after stirring for a while, compound 2 (6.5 g) was added. ) Was added in small portions. After stirring at room temperature for 5 hours, water was added, extracted with dichloromethane, and purified by silica gel column chromatography to obtain compound 3 (3.1 g).

  Reaction 2: Phosphorus oxychloride (1.8 ml) was added to a mixture of compound 3 (5.61 g), compound 4 (2.65 g) and toluene (15 ml), and the mixture was stirred at 115 ° C. for 2 hours. After returning to room temperature, saturated brine (30 ml) was added, and the mixture was extracted twice with chloroform. The product was purified by silica gel column chromatography (silica gel 300 g, chloroform / methanol 1 / 0-10 / 1/7/1), and the resulting solid was washed with hexane to obtain compound 5 (9.23 g).

Reaction 3: A mixture of compound 5 (5.00 g), compound 6 (2.56 g), and methanol (50 ml) was stirred at 40 ° C. for 1 hour, then concentrated under reduced pressure, water was added, and the solid was collected by filtration. The solid was washed with methanol / water: 1/3 (200 ml) and again washed with methanol / water: 1/3 (200 ml) to obtain Dye A (5.90 g).
[Preparation of colored resin composition]
The resin A synthesized in Reference Synthesis Example 1 and the dye A synthesized in Reference Synthesis Example 2 were mixed with other components so as to have the composition described in Table 1 to prepare a colored resin composition.
Table 2 shows the types and contents of Compound (I), Compound (II) and antioxidant in each Example and Comparative Example.

In addition, the numerical value in Table 1 and Table 2 represents the weight part of each component to add.
In mixing, the components were stirred for 1 hour or more until they were sufficiently mixed, and finally filtered through a 5 μm piece filter to remove foreign matters.

In addition, all the numerical values in Table 1 represent parts by weight of each component to be added.
Moreover, each compound in Table 1 is as follows.
PGMEA: Propylene glycol monomethyl ether acetate PGME: Propylene glycol monomethyl ether NMP: N-methyl-2-pyrrolidone Table 2 shows the compounds (I), (II) and antioxidants used in Examples and Comparative Examples.

  In addition, all the numerical values in Table 2 represent parts by weight of each component to be added.

3,4,5,7-tetrahydroxyflavone: manufactured by Tokyo Chemical Industry

Caffeic acid: manufactured by Tokyo Chemical Industry Co., Ltd. IRGANOX1010: manufactured by Ciba Specialty Chemicals Co., Ltd. JPP100: manufactured by Johoku Chemical Industry Co., Ltd. [3] Production of colored resin film and evaluation of heat resistance The composition was applied by spin coating so as to have a dry film thickness of 1.8 μm, dried under reduced pressure, and then pre-baked on a hot plate at 80 ° C. for 3 minutes. Then, after exposing the entire surface with an exposure amount of 60 mJ / cm ² , the spectral transmittance is measured with a spectrophotometer U-3310 (manufactured by Hitachi, Ltd.), and the chromaticity (C light source) in the XYZ color system is calculated. did.

  Subsequently, the substrate was baked at 230 ° C. for 30 minutes in a clean oven, and then the spectral transmittance was measured in the same manner as described above, and the chromaticity (C light source) in the XYZ color system was calculated. The color difference (ΔE * ab) from the chromaticity after firing, that is, the results of measuring the heat resistance are summarized in Table 3.

  As shown in Table 3, it can be seen that the pixels formed using the colored resin composition of the present invention have high luminance and particularly significantly improved heat resistance.

DESCRIPTION OF SYMBOLS 100 Organic EL element 20 Pixel 30 Organic protective layer 40 Inorganic oxide film 500 Organic light-emitting body 51 Hole injection layer 54 Electron injection layer

Claims (9)

A colored resin composition containing (A) a dye, (B) a solvent, and (C) a binder resin,
Furthermore, the coloring resin composition characterized by containing the compound represented by the following formula (I), and / or the following formula (II).

(In the above formula (I),
l represents an integer of 1 to 5;
R ¹ may have a hydrogen atom, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, an aromatic ring group which may have a substituent, or a substituent. Represents a heterocyclic group.
R ² and R ³ represent a hydrogen atom, a hydroxyl group, an aromatic ring group which may have a substituent, or a heterocyclic group which may have a substituent.
The benzene ring in the above formula (I) may have a substituent in addition to the hydroxyl group. )

(In the above formula (II),
m represents an integer of 0 to 4, and n represents an integer of 0 to 5.
However, m + n is 1 or more.
R ⁴ represents a hydrogen atom, a hydroxyl group, an alkoxyl group which may have a substituent, an aromatic ring group which may have a substituent, or a heterocyclic group which may have a substituent. Represent.
The benzene ring in the above formula (II) may have a substituent other than the hydroxyl group. )   2. The colored resin composition according to claim 1, wherein the compound represented by the formulas (I) and (II) is contained in a total solid content of 0.01 wt% or more and 10 wt% or less.   The colored resin composition according to claim 1, comprising an aprotic polar organic solvent as the solvent (B).   The colored resin composition according to any one of claims 1 to 3, wherein the aprotic polar organic solvent is contained in an amount of 0.1 wt% to 20 wt% in all solvents. The colored resin composition according to claim 1, further comprising (D) a polymerizable monomer.   The colored resin composition according to any one of claims 1 to 5, further comprising (E) a photopolymerization initiation component and / or a thermal polymerization initiation component.   The color filter which has a pixel formed using the colored resin composition as described in any one of Claims 1-6.   A liquid crystal display device comprising the color filter according to claim 7.   An organic EL display device comprising the color filter according to claim 7.

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