JP6094477B2 - Colored resin composition, color filter, liquid crystal display device and organic EL display device - Google Patents

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 (Electroluminescence) 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.
Color filters are required to improve color purity, saturation, and light transmission.
Conventionally, for the purpose of improving the light transmission amount, a method of reducing the content of the color pigment with respect to the photosensitive resin in the image forming material or thinning pixels formed by the image forming material has been adopted. I came.
However, these methods have a problem that the saturation of the color filter itself is lowered, and as a result, the entire display becomes whitish and the vividness of colors necessary for display is lost.
Conversely, if the coloring pigment content is increased with priority on saturation, the entire display becomes darker.In this case, the amount of light from the backlight must be increased in order to ensure brightness, which increases the power consumption of the display. There is a problem of being invited.

Furthermore, for the purpose of improving the light transmission amount, there is known a method of finely dispersing the particle size of pigment particles to ½ or less of the coloration wavelength (Non-Patent Document 1). Fine dispersion is required, and cost increases and stability after dispersion become problems.
On the other hand, a color filter using a dye as a coloring material is being developed. For example, as a colored resin composition for forming a blue pixel, Patent Document 1 includes C-I Acid Blue 83 (triallylamine dye) and C-I Solvent Blue 67 (copper phthalocyanine dye). A color filter provided with a blue filter layer is described.
In addition, as a colored resin composition for forming a green pixel, Patent Document 2 discloses the use of a colored resin composition containing a zinc phthalocyanine pigment and a yellow dye when forming a green pixel.

Japanese Unexamined Patent Publication No. 2002-14222 Japanese Unexamined Patent Publication No. 2010-168531

Kiyoshi Hashizume “Journal of Color Material Association” (December 1967, p608)

However, the colored resin composition for forming a blue pixel described in Patent Document 1 is not satisfactory in that it suppresses the deterioration of the image quality of the display that the entire display becomes whitish and lacks the vividness of colors necessary for display. It was enough.
In addition, the colored resin composition for forming a green pixel described in Patent Document 2 has insufficient pixel formation and developability.

The present invention has been made in view of the above problems, and has an object to provide a display having high image quality and excellent image formation and developability, and a colored resin composition capable of suppressing deterioration in image quality of the display. And
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 inventors have found that when a dye is used as a coloring material, the formed pixel surface is not sufficiently cured and the solvent resistance of the pixel is low. I found out that it was the cause.
The solvent resistance of the pixel indicates the difficulty of elution of the color material (pigment or dye) contained in the formed pixel into the solvent.
That is, if the solvent resistance of the pixel is insufficient, for example, when an alignment film or an overcoat is formed by coating, the color contained in the pixel is included in the solvent contained in the composition for forming these. It is presumed that the material is eluted and contaminates the liquid crystal layer formed on the alignment film or overcoat, resulting in a decrease in image quality of the display.
The reason why the solvent resistance tends to decrease when a dye is used for the coloring material is further estimated as follows.
When a dye is included, even if the photopolymerization initiator is in an excited state upon receiving light energy during exposure, the energy is transferred to the dye before the photopolymerization initiator generates radicals due to contact with the dye, It has been found that some of the photopolymerization initiators do not function as radicals.
When the dye is used, the above phenomenon occurs because the probability of contact with the photopolymerization initiator is higher when the dye is present in a substantially monomolecular state than when the pigment is associated with the coloring material in the colored resin composition. Is big. That is, when a dye is included rather than a pigment, there is a high probability that the energy of the photopolymerization initiator moves. Therefore, when a dye is included, it is presumed that the radical generation function of the photopolymerization initiator does not work sufficiently than when a pigment is used, resulting in a decrease in solvent resistance and, in some cases, insufficient pixel formation. .

As a result of obtaining the above knowledge and conducting further diligent studies, the inventors have found that the above-mentioned problems can be solved by including a specific compound in the colored resin composition containing a dye, and have reached the present invention.
That is, the present invention resides in the following colored resin composition, color filter, liquid crystal display device and organic EL display device.
[1] A colored resin composition containing (A) a dye, (B) a solvent, (C) a binder resin and (D) a chain transfer agent, wherein the (D) chain transfer agent is represented by the following formula (I) A colored resin composition comprising the compound represented (hereinafter, sometimes referred to as “compound (I)”).

(In the above formula (I), p represents an integer of 2 to 4.
R ^a1 represents a hydrogen atom or an alkyl group which may have a substituent.
X represents a direct bond, a 2-4 quaternary carbon atom, a 2-4 valent heterocyclic group or a 2-4 valent aromatic ring group.
In addition, a plurality of structures represented by the following formula (I ′) contained in one molecule

May be the same or different. )
[2] The colored resin composition according to [1], wherein the content of the (D) chain transfer agent is 2% by weight or more and 10% by weight or less in the total solid content.
[3] The colored resin composition according to [1] or [2], wherein the dye is a triarylmethane dye.
[4] The colored resin composition according to any one of [1] to [3], further comprising (E) a polymerizable monomer.
[5] The colored resin composition according to [4], wherein the polymerizable monomer (E) is a compound having an ethylenically unsaturated double bond.
[6] The colored resin composition according to any one of [1] to [5], further including (F) at least one of a photopolymerization initiation component and a thermal polymerization initiation component.
[7] A color filter including pixels formed using the colored resin composition according to any one of [1] to [6].
[8] A liquid crystal display device having the color filter according to [7].
[9] An organic EL display device having the color filter according to [7].

  By using the colored resin composition of the present invention, it is possible to form a pixel that is excellent in pixel formability and developability and has high solvent resistance. Thus, the liquid crystal display device including pixels formed using the colored resin composition of the present invention has high image quality.

  In addition, a color filter having excellent color purity and transparency of the pixel can be obtained. By using such a color filter, light emission from the backlight of the color filter can be efficiently extracted, and high color reproducibility and high performance can be obtained. It is possible to provide a liquid crystal display device and an organic EL display device that are compatible in luminance.

FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element including the 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.
Here, in the present specification, “mass%” and “wt%”, “mass ppm” and “weight ppm”, and “mass part” and “weight part” are synonymous, respectively. In addition, when “ppm” is simply described, it indicates “weight ppm”.

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 for color filter of the present invention other than the solvent components described later.
Furthermore, “aromatic ring” means both “aromatic hydrocarbon ring” and “aromatic heterocycle”.

The colored resin composition of the present invention contains the compound (I) in (A) a dye, (B) a solvent, (C) a binder resin, and (D) a chain transfer agent, preferably (E) a polymerizable monomer. (F) A photopolymerization initiating component and / or a thermal polymerization initiating component are included, and further other components are blended as necessary.
First, (D) the chain transfer agent contained in the colored resin composition of the present invention will be described.

[(D) Chain transfer agent]
The (D) chain transfer agent in the present invention is a compound having a function of receiving a generated radical and transferring the radical to another compound.
The colored resin composition of the present invention contains a compound represented by the following formula (I) as (D) a chain transfer agent.

(In the above formula (I), p represents an integer of 2 to 4.
R ^a1 represents a hydrogen atom or an alkyl group which may have a substituent.
X represents a direct bond, a 2-4 quaternary carbon atom, a 2-4 valent heterocyclic group or a 2-4 valent aromatic ring group.
In addition, a plurality of structures represented by the following formula (I ′) contained in one molecule

May be the same or different. )

(About R ^a1 )
R ^a1 represents a hydrogen atom or an alkyl group which may have a substituent.
As said alkyl group, carbon number is 1-8 normally, Most preferably, it is 1 or 2.
R ^a1 is preferably a hydrogen atom in that the reactivity of the compound is high and the surface curability of the resulting film is high.
As the substituent that the alkyl group have the R ^a1, for example, those described in the section below (substituent group W ^1).

(Substituent group W ¹ )
Fluorine atom, chlorine atom, 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 having 2 to 9 carbon atoms A carboxyl group, a sulfonic acid amide group, a sulfone alkylamide group having 2 to 9 carbon atoms, an alkylcarbonyl group having 2 to 9 carbon atoms, a phenethyl group, a hydroxyethyl group, an acetylamide group, and an alkyl group having 1 to 4 carbon atoms are bonded. A dialkylaminoethyl group, a trifluoromethyl group, a trialkylsilyl group having 1 to 8 carbon atoms, a nitro group, and an alkylthio group having 1 to 8 carbon atoms.

(About X)
In formula (I), X represents a direct bond, a 2-4 quaternary carbon atom, a 2-4 valent heterocyclic group, or a 2-4 valent aromatic ring group.
The case where X is a secondary to quaternary carbon atom means that X has any one of the following structures.

Examples of the aromatic ring group for X 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 it has 5 to 18 carbon atoms to form the ring. Examples thereof include groups having a valence such as a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, and fluorene 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.
In addition, 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. For example, a furan ring, a 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, fluropyrrole 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, cinnoline ring, quinoxaline ring, phenanthridine ring , Benzimidazole ring, perimidi Ring, quinazoline ring, a quinazolinone ring, and azulene ring.

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 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 heteroatoms constituting the ring, 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.
X is preferably a secondary to quaternary carbon atom, particularly preferably a quaternary carbon atom, from the viewpoint of good storage stability of the compound (I).
In addition, the carbon atom, heterocyclic group and aromatic ring group in X have a substituent represented by other than the following structural formula (I ′) (hereinafter sometimes referred to as “sulfanyl group-containing structure”). Examples of the substituent include those described in the above section (Substituent group W ¹ ).

(About p)
p represents an integer of 2 to 4.
In Compound (I), p is particularly preferably 4 in that the reactivity of the compound is increased by increasing the number of sulfanyl groups that are reaction sites, and the resulting pixel has sufficient curability.

Specific examples of compound (I) in the present invention are shown below, but the present invention is not limited thereto.
[Specific Examples of Compound (I)]
Compounds having two sulfanyl group-containing structures: 1,2-ethanedithiol, 1,3-propanedithiol, 1,4-butanedithiol, 2,3-butanedithiol, 1,5-pentanedithiol, 1,6-hexane Dithiol, 1,8-octanedithiol, 1,9-nonanedithiol, 2,3-dimercapto-1-propanol, dithioerythritol, 1,2-benzenedithiol, 1,2-benzenedimethanethiol, 1,3-benzene Dithiol, 3,4-dimercaptotoluene, 4-chloro-1,3-benzenedithiol, 2-hexylamino-4,6-dimercapto-1,3,5-triazine, 2-diethylamino-4,6-dimercapto- 1,3,5-triazine, 2-cyclohexylamino-4,6-dimercapto-1,3 5-triazine, ethylene glycol bis (3-mercaptopropionate), 2,5-dimercapto-1,3,4-thiadiazole, 2,2-bis (2-hydroxy-3-mercapto-propoxyphenyl propane,
Compounds having three sulfanyl group-containing structures: trimethylolpropane tris (3-mercaptopropionate), trimethylolpropane tristhioglycolate, 1,2,6-hexanetriol trithioglycolate, etc.
Examples include compounds having four sulfanyl group-containing structures: pentaerythritol tetrakisthioglycolate, pentaerythritol tetrakis (3-mercaptopropionate), and the like.
Among the above, pentaerythritol tetrakis (3-mercaptopropionate) is particularly preferable.

(About content)
The content of the (D) chain transfer agent in the present invention is usually 2% by weight or more, preferably 4% by weight or more, more preferably 6% by weight or more, and usually 10% by weight or less in the solid content of the colored resin composition. , Preferably 9% by weight or less, more preferably 8.5% by weight or less.
Within the above range, it is preferable in that the obtained pixel has sufficient curability and does not easily affect luminance reduction of the obtained pixel.
The colored resin composition of the present invention may contain a chain transfer agent other than the compound (I). In that case, the colored resin composition contains (D) the total content of the chain transfer agent within the above range. do it.
However, it is particularly preferable to contain only the compound (I) as the (D) chain transfer agent, and it is preferable to contain the compound (I) within the above range.

<Reason for effect>
The reason why the effect of suppressing the deterioration in image quality of the obtained liquid crystal display device can be obtained by using the configuration of the present application is estimated as follows.
As described above, the cause of the deterioration in image quality of the liquid crystal display device is that the obtained pixels have insufficient solvent resistance.
Therefore, attention was focused on improving the solvent resistance by increasing the curability of the obtained pixels.
In order to improve the sclerosis | hardenability of a pixel, it is necessary to fully function polymerizable sclerosing | hardenable components, such as binder resin contained in a colored resin composition.
To fully function the polymerizable curable component means that polymerization occurs in a wide range of pixels.
Conventionally, for example, in the case of a photopolymerization system, polymerization occurs only in the very vicinity where the photopolymerization initiator is present, and since the generated radicals do not diffuse, polymerization in a wide range is unlikely to occur and sufficient for pixels. Curing sufficient to provide solvent resistance was not obtained.
Here, in the present invention, the generated radical containing the compound represented by the formula (I) can be diffused over a wide range through the compound represented by the formula (I).
As a result, the polymerization reaction is more easily performed, the curing is performed so that sufficient solvent resistance is imparted to the pixels, and the image quality deterioration of the liquid crystal display device can be suppressed.

[(A) Dye]
The (A) dye in the present invention is not particularly limited as long as the effects of the present invention are not impaired. For example, an azo dye, anthraquinone dye, phthalocyanine dye, quinoneimine dye, quinoline dye, nitro dye, Preferred examples include carbonyl dyes, methine dyes, cyanine dyes, and triarylmethane dyes.
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.
Among these, the optimum dye varies depending on the desired pixel color.

In the case of forming a blue pixel, a triarylmethane dye and a cyanine dye are preferable, and a triarylmethane dye is particularly preferable because the luminance of the obtained pixel is high.
In addition, when it is a triarylmethane type dye, it is preferable at the point from which the effect of this invention is acquired more easily.
In the case of forming a red pixel or a green pixel, the yellow dye used as a complementary color thereof is particularly preferably an azo yellow dye because the effect of the present invention can be easily obtained.
First, the dye suitably used for the colored resin composition for forming a blue pixel, that is, a triarylmethane dye and a cyanine dye will be described in detail.

[Triarylmethane dyes]
(Triarylmethane dyes: compounds represented by formula (II))
As the triarylmethane dye, a compound represented by the following formula (II) (hereinafter referred to as “compound (II)”) is excellent in heat resistance and particularly in blue purity and transmittance of the obtained pixel. It is particularly preferable that

(In the formula (II), Z ^m1- represents an m1-valent anion.
m1 represents an integer of 1 to 4.
R ^{1 to} R ⁶ each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or an aromatic ring group optionally having a substituent. Adjacent R ^{1 to} R ⁶ may be bonded to form a ring. The ring may have a substituent.
R ⁷ and R ⁸ represent a hydrogen atom or an arbitrary substituent. R ⁷ and R ⁸ may be connected to each other to form a ring.
Moreover, the benzene ring in the above formula (II) may further have an arbitrary substituent.
In addition, multiple molecules in one molecule

May be the same structure or different structures. )

(For ^R 1 ^{~R 6)}
R ^{1 to} R ⁶ each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or an aromatic ring group optionally having a substituent.
Examples of the alkyl group in R ^{1 to} R ⁶ include linear, branched, or cyclic alkyl groups having 1 or more carbon atoms and usually 8 or less, preferably 5 or less carbon atoms. . Specific examples include methyl group, ethyl group, n-propyl group, 2-propyl group, n-butyl group, isobutyl group, tert-butyl group, cyclohexyl group and the like.

Examples of the aromatic ring in R ^{1 to} R ⁶ include an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
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.
In addition, 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.

Adjacent R ^{1 to} R ⁶ may be bonded to form a ring, and the ring may have a substituent.
When adjacent R < ¹ > -R < ⁶ > couple | bonds together and forms a ring, the ring bridge | crosslinked by the hetero atom may be sufficient as these. Specific examples of this ring include the following. These rings may have a substituent.

From the viewpoint of chemical stability, R ^{1 to} R ⁶ are preferably each independently a hydrogen atom, a C 1-8 alkyl group which may have a substituent, or a substituent. It is a good phenyl group, or it is a case where adjacent R ^{1 to} R ⁶ are bonded to each other to form a ring, and is more preferable in that the heat resistance of the dye is improved and the light resistance of the resulting color filter is excellent. Is a C1-C8 alkyl group which may have a substituent or a phenyl group which may have a substituent.

When R ^{1 to} R ⁶ are an optionally substituted alkyl group having 1 to 8 carbon atoms, it is presumed that the charges in the cation are dispersed by hyperconjugation and the cation is stabilized.
Further, when R ^{1 to} R ⁶ are phenyl groups which may have a substituent, it is assumed that the cation is stabilized by extending the conjugated system and dispersing the charge in the cation. Is done. As described above, it can be considered that the light resistance of the obtained color filter becomes more excellent as a result of stabilization of the cation.
The R ¹ alkyl group in to R ^6, an aromatic hydrocarbon ring group and an adjacent R ¹ to R ⁶ are bonded to each other ring substituents which may have formed by, for example, the following (substituted Those of the group W ² ).

(Substituent group W ² )
C1-C8 alkyl group, C2-C8 alkenyl group, C1-C8 alkoxy group, C6-C15 aryl group, C2-C9 alkylcarbonyloxy group, C7 -16 arylcarbonyloxy group, C2-C9 alkoxycarbonyl group, C7-C16 aryloxycarbonyl group, carbamoyl group, C2-C9 alkylcarbamoyl group, C7-C16 arylcarbamoyl Group, sulfamoyl group, alkylsulfamoyl group having 1 to 8 carbon atoms, arylsulfamoyl group having 6 to 15 carbon atoms, alkylcarbonyl group having 2 to 9 carbon atoms, arylcarbonyl group having 7 to 16 carbon atoms, carbon An alkylsulfonyl group having 1 to 8 carbon atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, and an arylsulfonylamino group having 6 to 15 carbon atoms An amino group, an alkylamino group formed by bonding an alkyl group having 1 to 8 carbon atoms, a dialkylamino group formed by bonding an alkyl group having 1 to 4 carbon atoms, an arylamino group having 6 to 15 carbon atoms, or 6 carbon atoms An arylalkylamino group formed by bonding an aryl group having 15 to 15 carbon atoms and an alkyl group having 1 to 4 carbon atoms, a diarylamino group formed by bonding an aryl group having 6 to 15 carbon atoms, a phenethyl group, a hydroxyethyl group, 1 carbon atom ˜8 alkylcarbonylamino group, C7-16 arylcarbonylamino group, dialkylaminoethyl group formed by bonding of C1-4 alkyl group, trifluoromethyl group, C1-8 trialkyl Silyl group, alkylthio group having 1 to 8 carbon atoms, arylthio group having 6 to 15 carbon atoms, hydroxy group, nitro group, cyano group, carboxy group, sulfo group Group, a fluorine atom, a halogen atom such as a chlorine atom.
Specific examples of the aryl group in the substituent group W ² include those described as the aromatic ring groups in R ^{1 to} R ⁶ . The aryl group is a lower alkyl group such as a methyl group or an ethyl group, a lower alkoxy group such as a methoxy group or an ethoxy group, a nitro group, a trifluoromethyl group, a cyano group, a carbamoyl group, a sulfamoyl group, a fluorine atom, or a chlorine atom. May be further substituted as a substituent.
Especially, as a substituent which the alkyl group in R < ¹ > -R < ⁶ >, an aromatic ring group, and the ring formed by mutually connecting may have, Preferably it is a C1-C8 alkyl group, C1-C1 8 alkoxy group, phenyl group, tolyl group, alkylcarbonyloxy group having 2 to 9 carbon atoms, carbamoyl group, sulfamoyl group, alkylsulfamoyl group having 1 to 8 carbon atoms, trifluoromethyl group, cyano group, sulfo group And a fluorine atom.

(About R ⁷ and R ⁸ )
R ⁷ and R ⁸ represent a hydrogen atom or an arbitrary substituent.
As this arbitrary substituent, the C1-C8 alkyl group which may have a halogen atom, a substituent, the aromatic ring group which may have a substituent, etc. are mentioned, for example.
R ⁷ and R ⁸ may be connected to each other to form a ring.
When R ⁷ and R ⁸ are bonded to each other to form a ring, these may be a ring bridged with a heteroatom. Specific examples of this ring include the following. These rings may have a substituent.

(In the above, R ^1z and R ^2z each independently represent a hydrogen atom or an alkyl group.)
From the viewpoint that the obtained color filter is blue and has high luminance, it is preferable that R ⁷ and R ⁸ are not connected to each other to form a ring.

Moreover, the benzene ring in the above formula (II) may further have an arbitrary substituent.
Examples of the substituent that the benzene ring may have include those described in the above section (Substituent group W ² ).

(About Z ^m1- )
Z ^m1- represents an m1-valent anion.
The anion is not particularly limited as long as the effect of the present invention is not impaired. For example, halide ions such as F ⁻ , Cl ⁻ , Br ⁻ and I ⁻ ;
_{(C 6 H 5) 4 B} - like boron anion;
Carboxylic acid anions such as CH ₃ COO ⁻ , C ₂ H ₅ COO ⁻ , C ₆ H ₅ COO ⁻ ;
Sulfate anions such as SO ₄ ²⁻ and HSO ₄ ⁻ ;
Phosphate anions such as HPO ₄ ²⁻ , PO ₄ ³⁻ ;
Examples include sulfonate anions.
Examples of the sulfonate anion include aliphatic sulfonate anions which may have a substituent such as trifluoromethanesulfonic acid, methanesulfonic acid, pentanesulfonic acid, hexanesulfonic acid, heptanesulfonic acid, dodecanesulfonic acid, and camphorsulfonic acid. ;
An aromatic sulfonate anion optionally having a substituent such as benzenesulfonic acid, p-toluenesulfonic acid, 1-naphthalenesulfonic acid, 2-naphthalenesulfonic acid;
acid blue 80 (C.I. 61585), acid green 25 (C.I. 61570), acid blue 45 (C.I. 63010), acid blue 43 (C.I. 63000), acid blue 25 (C.I. An anion of an anthraquinone dye having a sulfonate group such as I.62055), acid blue 40 (C.I. 65125);
anions of phthalocyanine dyes having a sulfonate group such as direct blue 86 (C.I. 74810), direct blue 199 (C.I. 14190);
an anion of an indigo dye having a sulfonate group such as acid blue 74 (C.I.73015);
And disulfonylimide anion.
Among them, disulfonylimide anion is preferable, and the compound represented by the formula (II) is particularly preferably a compound represented by the following formula (II-1).

^(Wherein, R 1 to R ⁸ have the same meanings as ^R 1 to R ⁸ in Formula (II).
R ²¹ and R ²² are each independently an alkyl group having 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 6 carbon atoms which may have a substituent, or a substituent. The C3-C8 cycloalkyl group which may have is represented.
R ²¹ and R ²² may be bonded to each other to form a ring. )

(About R ²¹ and R ²² )
R ²¹ and R ²² are each independently an alkyl group having 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 6 carbon atoms which may have a substituent, or a substituent. The C3-C8 cycloalkyl group which may have is represented.
R ²¹ and R ²² may be bonded to each other to form a ring.
Examples of the substituent include those described in the above section (Substituent group W ² ).

Among these, in particular, as the substituent of the alkyl group, alkenyl group or cycloalkyl group in R ²¹ and R ²² , the anion charge is more delocalized, and the heat resistance of the coloring material is improved. It preferably has a fluorine atom as a substituent.
That is, R ²¹ and R ²² are preferably a C 1-8 perfluoroalkyl group in that the anion charge is dispersed and the anion is stabilized.
More specifically, in the compound represented by the formula (II)

Is preferably a compound represented by the following formula (II′-1). The anion represented by the formula (hereinafter sometimes referred to as “anion in the compound represented by the formula (II)”) is .

(In the above formula (II′-1), n and n ′ each independently represent an integer of 1 to 8)
n and n ′ are generally an integer of 1 to 8, preferably 1 to 4.
n and n ′ may be the same or different.
Specific examples of the sulfonylimide anion when n and n ′ are the same include bis (trifluoromethanesulfone) imide, bis (pentafluorobutanesulfone) imide and the like.
Specific examples of the sulfonylimide anion when n and n ′ are different include pentafluoroethanesulfone trifluoromethanesulfonimide, trifluoromethanesulfone heptafluoropropanesulfonimide, fluorobutanesulfone trifluoromethanesulfonimide, and the like.
Among these, bis (pentafluoroethanesulfone) imide, where n = n ′ = 2, is particularly preferable because the anion is most stabilized.

On the other hand, R ¹¹ and R ¹² may be bonded to each other to form a ring.
In the case of forming a ring, R ¹¹ and R ¹² are particularly preferably a fluoroalkylene group having 2 to 12 carbon atoms.
That is, the anion in the compound represented by the formula (II-1) is preferably an anion represented by the following formula (II′-2).

(In the above formula (II′-2), n ″ represents an integer of 2 to 12)
n ″ is preferably 2 to 8 and more preferably 3 in terms of heat resistance.
The smaller the number of n ″, the smaller the effect of steric repulsion and the stronger the interaction. That is, it is presumed that the smaller n ″ is, the larger the interaction between anion and cation is, and the ion pair is stabilized and the heat resistance of the coloring material is improved.
Although the preferable specific example of the compound represented by Formula (II) in this invention is shown below, this invention is not limited to these.
[Specific Examples of Compound (II)]

(Triarylmethane dyes: compounds represented by formula (III))
The triarylmethane dye is a compound represented by the following formula (III) (hereinafter sometimes referred to as “compound (III)”) in that it has light resistance, heat resistance, and high transmittance. Is preferred.

(In the above formula (III), ^Zm2- represents an m2-valent anion.
m2 represents an integer of 1 to 4.
R ^{11 to} R ¹⁶ each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or an optionally substituted aromatic ring group. R ¹¹ and R ¹² , R ¹³ and R ^14, and R ¹⁵ and R ¹⁶ may be bonded to each other to form a ring structure.
R ¹⁷ and R ¹⁸ each independently represents a hydrogen atom or an arbitrary substituent. R ¹⁷ and R ¹⁸ may be bonded to each other to form a ring.
Further, the benzene ring and indole ring in the above formula (III) may further have an arbitrary substituent.

  In addition, multiple molecules in one molecule

May be the same structure or different structures. )

(About R ^{11 to} R ¹⁶ )
R ^{11 to} R ¹⁶ each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or an optionally substituted aromatic ring group.
Examples of the alkyl group having 1 to 8 carbon atoms and the aromatic ring group are the same as those described in the above section (for R ^{1 to} R ⁶ ).
Further, when adjacent R ^{11 to} R ¹⁶ , that is, R ¹¹ and R ¹² , R ¹³ and R ^14, and R ¹⁵ and R ¹⁶ are bonded to each other to form a ring structure, the above (R ^{1 to} R ⁶ ) are the same as those described in the section).

(About R ¹⁷ and R ¹⁸ )
R ¹⁷ and R ¹⁸ represent a hydrogen atom or an arbitrary substituent. Examples of the optional substituents include those described in the R ¹ to R ^6.
R ¹⁷ and R ¹⁸ may be connected to each other to form a ring.
When R ¹⁷ and R ¹⁸ are bonded to each other to form a ring, these may be a ring bridged with a heteroatom, and specific examples thereof are described in the above section (for R ⁷ and R ⁸ ). It is the same as that. These rings may have a substituent.
From the viewpoint that the obtained color filter is purple and has high luminance, it is preferable that R ⁷ and R ⁸ are not connected to each other to form a ring.
In addition, it is preferable that the obtained color filters are red and have high luminance, so that they are connected to each other to form a ring.

In compound (III), the benzene ring and the indole ring may further have a substituent. That is, you may have a substituent other than having specified in Formula (III) in the range which does not impair the effect of this invention.
Examples of such a substituent include the substituents described in the above section (Substituent group W ² ).
In addition, in the benzene ring in formula (III), when a bulky group is bonded to the carbon atom located at the center of the triarylmethine structure, the planarity of the molecule is inhibited, and the compound Color purity may be reduced. Accordingly, it is preferable that the o-position does not have a substituent or is substituted with a halogen atom or an alkyl group having 1 to 4 carbon atoms.
Moreover, the compound (III) may form a dimer, a trimer, etc. by extending a linker from, for example, R ^{11 to} R ¹⁸ .

(About the compound represented by Formula (III-1))
In the compound (III), particularly preferably, the anion is a disulfonylimide anion. In the formula (III), a compound represented by the following formula (III-1) (hereinafter referred to as “compound (III-1)”) It may be referred to as “.

^(Wherein, R 11 ^{to R 18} are the same as ^R 11 ^{to R 18} in the formula (III).
R ³¹ and R ³² are each independently an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent. The C3-C8 cycloalkyl group which may have is represented.
R ³¹ and R ³² may be bonded to each other to form a ring. )

(About R ³¹ and R ³² )
R ³¹ and R ³² are each independently an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent. The C3-C8 cycloalkyl group which may have is represented.
R ³¹ and R ³² may be bonded to each other to form a ring.
R ³¹ and R ³² are the same as R ²¹ and R ²² in the formula (II-1), and preferred embodiments are also the same.
That is, the anion represented by the formula (III-1) is preferably an anion represented by the formula (II′-1) or (II′-2).

Although the preferable specific example of the compound represented by Formula (III) in this invention is shown below, this invention is not limited to these.
[Specific Examples of Compound (III)]

(Triarylmethane dyes: compounds represented by formula (IV))
The triarylmethane dye is a compound represented by the following formula (IV) (hereinafter sometimes referred to as “compound (IV)”) in that the luminance of the obtained pixel is high and the voltage holding ratio is high. It is preferable that

(In the above formula, R ^{41 to} R ⁴⁶ each independently represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent.
Adjacent R ^{41 to} R ⁴⁶ may be connected to each other to form a ring, and the ring may have a substituent.
R ⁴⁷ and R ⁴⁸ each independently represents a hydrogen atom or an arbitrary substituent.
R ⁴⁷ and R ⁴⁸ may be bonded to each other to form a ring, and the ring may have a substituent.
Moreover, the benzene ring and indole ring in the above formula (IV) may further have an arbitrary substituent.
M ⁺ represents a hydrogen ion, an alkali metal cation, an alkaline earth metal cation, a tertiary ammonium cation or a quaternary ammonium cation.
n represents an integer of 0 to 4. )

(About R ^{41 to} R ⁴⁶ )
R ^{41 to} R ⁴⁶ each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent.
Examples of the alkyl group which may have a substituent and the aromatic ring group which may have a substituent include those described in the above section (for R ^{1 to} R ⁶ ).
It has the C1-C8 alkyl group or substituent which may have a substituent more preferably at the point which improves the heat resistance of compound (IV), and the heat resistance of the color filter obtained is excellent. It may be an aromatic hydrocarbon ring group having 6 to 10 carbon atoms, and more preferably an alkyl group having 1 to 8 carbon atoms or a phenyl group which may have a substituent.
When at least one of R ^{41 to} R ⁴⁶ is an optionally substituted alkyl group having 1 to 8 carbon atoms, it is presumed that the charge in the cation is dispersed by hyperconjugation and the cation is stabilized. Is done.
In addition, when at least one of R ^{41 to} R ⁴⁶ is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, the conjugated system is extended, so that the charge in the cation is dispersed. Thus, the cation is stabilized. As described above, it can be considered that as a result of stabilization of the cation, the heat resistance of the obtained color filter is further improved.
That is, it R ⁴¹ to R ⁴⁶ is an aromatic hydrocarbon group of the alkyl group or carbon atoms which may have a substituent 6-10 having 1 to 8 carbon atoms which may have a substituent Is preferred.
Examples of the substituent that the alkyl group, the aromatic ring group, and the ring formed by being linked to each other in R ^{41 to} R ⁴⁶ may have include those described above in (Substituent group W ² ).

(About R ⁴⁷ and R ⁴⁸ )
R ⁴⁷ and R ⁴⁸ represent a hydrogen atom or an arbitrary substituent. As this arbitrary substituent, the C1-C8 alkyl group which may have a halogen atom, a substituent, the aromatic ring group which may have a substituent, etc. are mentioned, for example.
R ⁴⁷ and R ⁴⁸ are the same as those described in the above section (for R ¹⁷ and R ¹⁸ ). The preferred embodiment is also the same.

(About M ⁺ and n)
M ⁺ represents a hydrogen ion, an alkali metal cation, an alkaline earth metal cation, a tertiary ammonium cation or a quaternary ammonium cation.
Examples of the alkali metal of the alkali metal cation include lithium, sodium, and potassium. Examples of the alkaline earth metal of the alkaline earth metal cation include magnesium, calcium, and barium.
The tertiary ammonium cation represents N ⁺ HR ₃ (R represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent. R may be the same or different.
Examples of the preferred carbon number of the alkyl group in R and the substituents that may be present are the same as those exemplified for the alkyl groups of R ^{41 to} R ⁴⁶ . Examples of the preferable number of carbon atoms of the aromatic ring group and the substituent which may be included are the same as those exemplified in the case of the aromatic ring group of R ^{41 to} R ⁴⁶ . Specifically, a lower alkyl ammonium cation having 1 to 6 carbon atoms (for example, methyl ammonium cation, ethyl ammonium cation, diethyl ammonium cation, triethyl ammonium cation, etc.), an alkyl ammonium cation having 1 to 6 carbon atoms substituted with a hydroxy group. (Eg, ethanolammonium cation, diethanolammonium cation, triethanolammonium cation, etc.), carboxy-substituted alkylammonium cations having 1 to 6 carbon atoms (eg, carboxymethylammonium cation, carboxyethylammonium cation, carboxypropylammonium cation, Carboxymethylammonium cation, etc.), ammonium cation substituted with an aromatic ring group and an alkyl group (for example, N N- diethyl-phenyl ammonium cation and the like) and the like.

The quaternary ammonium cation is represented by N ⁺ R ₄ , and R represents an alkyl group which may have a substituent or an aromatic ring group which may have a substituent. A plurality of Rs may be the same or different. The preferred carbon number of the alkyl group and examples of the substituent which may be present are the same as those exemplified in the case of the alkyl group of R ^{1 to} R ⁶ . Examples of the preferable number of carbon atoms of the aromatic ring group and the substituents that may be included are the same as those exemplified for the aromatic ring groups of R ^{1 to} R ⁶ .
Specific examples include quaternary alkylammonium cations having 1 to 6 carbon atoms (for example, tetramethylammonium cation, tetraethylammonium cation, tetrabutylammonium cation, etc.).

In addition, the kind of the cation of M ⁺ is not limited to one kind, and a plurality of kinds may be mixed. Moreover, multiple types may be mixed in one molecule of a compound, and multiple types may be mixed in the colored resin composition.
Preferred as M ⁺ is a hydrogen ion, an alkali metal cation, a tertiary ammonium cation, or a quaternary ammonium cation from the viewpoint of solubility in an organic solvent used in the colored resin composition, and more preferably a lithium cation, Sodium cation, unsubstituted ammonium cation and tetrabutylammonium cation are preferred.

n represents an integer of 0 to 4.
The larger n is, the more the sulfo group of the hydrophilic group is substituted in the compound (IV), the heat resistance and light resistance are improved, and the solubility of the compound (IV) in the hydrophobic liquid crystal is also lowered. Although the voltage holding ratio is also improved, it is preferably 0 to 2 in terms of high solubility in the organic solvent used in the colored resin composition.

[Compound represented by Formula (IV-1)]
Compound (IV) in the present invention is a compound represented by the following formula (IV-1) (hereinafter referred to as “compound (IV-)” in that the color purity and transmittance of the obtained pixel are excellent when used in a color filter. 1) may be referred to)).

(In the above formula, R ^{51 to} R ⁵⁶ each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent.
Adjacent R ^{51 to} R ⁵⁶ may be connected to each other to form a ring, and the ring may have a substituent.
R ⁵⁷ and R ⁵⁸ each independently represent a hydrogen atom or an arbitrary substituent.
R ⁵⁷ and R ⁵⁸ may be connected to each other to form a ring, and the ring may have a substituent.
The benzene ring and indole ring in the above formula (IV-1) may further have an arbitrary substituent. )

The SO ₃ ^— group shown in the above formula (IV-1) is substituted on any carbon of the indole ring. Moreover, when the sulfo group is substituted in the benzene ring in the above formula (IV-1) and R ^{11 to} R ¹⁸ described below, the sulfo group is represented by M ⁺ represented by the above formula (IV). A salt may be formed.

(About R ^{51 to} R ⁵⁶ )
R ^{51 to} R ⁵⁶ are respectively synonymous with R ^{41 to} R ⁴⁶ in the compound (IV). Specific examples and preferred embodiments are also the same.
(About R ⁵⁷ and R ⁵⁸ )
R ⁵⁷ and R ⁵⁸ have the same meanings as R ⁴⁷ and R ⁴⁸ in compound (IV), respectively. Specific examples and preferred embodiments are also the same.

[Compound represented by formula (IV-2)]
The compound (IV) of the present invention is a compound represented by the following formula (IV-2) (hereinafter referred to as “compound (IV-)” in that the color purity and transmittance of the obtained pixel are excellent when used in a color filter. 2) ”may be referred to).

(In the above formula, R ^{61 to} R ⁶⁵ each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent.
Adjacent R ^{61 to} R ⁶⁵ may be connected to each other to form a ring, and the ring may have a substituent.
R ⁶⁷ and R ⁶⁸ each independently represent a hydrogen atom or an arbitrary substituent.
R ⁶⁷ and R ⁶⁸ may be connected to each other to form a ring, and the ring may have a substituent.
Q ² is a divalent aromatic ring group that may have a substituent, a divalent aliphatic hydrocarbon group that may have a substituent, or a divalent that may have a substituent. An aliphatic heterocyclic group, one group selected from the group consisting of —C (═O) —, —O—, —S— and —NH—, or a group formed by bonding two or more of these.
Moreover, the benzene ring and indole ring in the above formula (IV-2) may further have an arbitrary substituent. )

When the sulfo group is substituted in the benzene ring, indole ring, Q ² , R ^{61 to} R ⁶⁵ and R ⁶⁷ and R ⁶⁸ described below in the formula (IV-2), the sulfo group is represented by the formula A salt may be formed with M ⁺ shown in (IV).

(For ^R 61 ^{~R 65)}
R ^{61 to} R ⁶⁵ are respectively synonymous with R ^{41 to} R ⁴⁵ in the compound (IV). Specific examples and preferred embodiments are also the same.
(About R ⁶⁷ and R ⁶⁸ )
R ⁶⁷ and R ⁶⁸ have the same meanings as R ⁴⁷ and R ⁴⁸ in compound (IV), respectively. Specific examples and preferred embodiments are also the same.

(For ^{Q 2)}
Q ² is a divalent aromatic ring group that may have a substituent, a divalent aliphatic hydrocarbon group that may have a substituent, or a divalent that may have a substituent. An aliphatic heterocyclic group, one group selected from the group consisting of —C (═O) —, —O—, —S— and —NH—, or a group formed by bonding two or more of these.
The divalent aromatic ring group has two free valences in the aromatic ring having one free valence described in the above section (for R ^{51 to} R ⁵⁶ ), and Examples include groups having 2 to 14 carbon atoms. Examples of the substituent that these groups may have include those described above in (Substituent group W ² ).
The divalent aliphatic hydrocarbon group is a linear, branched or cyclic group and is an aliphatic hydrocarbon group, the carbon number of which is usually 1 or more, and usually 8 or less, preferably Is 6 or less. Specific examples include an alkylene group having 1 to 8 carbon atoms, a cyclopentanediyl group, and a cyclohexanediyl group. Examples of the substituent that these groups may have include those described above in (Substituent group W ² ).
Examples of the divalent aliphatic heterocyclic group include piperidinyl group, pyrrolidinyl group, imidazolidinyl group, pyrazolidinyl group, piperazinyl group, morpholinyl group, indolinyl group, isoindolinyl group and the like. Examples of the substituent that these groups may have include those described above in (Substituent group W ² ).

[Compound represented by formula (IV-3)]
The compound (IV) of the present invention is a compound represented by the following formula (IV-3) (hereinafter referred to as “the compound of the present invention” in that the color purity and transmittance of the obtained pixel are excellent when used as a color filter. (IV-3) ”may be preferred).

(In the above formula, R ^{71 to} R ⁷³ and R ^{75 to} R ⁷⁶ are each independently a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent. Indicates.
Q ³ is a divalent aromatic ring group that may have a substituent, a divalent aliphatic hydrocarbon group that may have a substituent, or a divalent that may have a substituent. An aliphatic heterocyclic group, one group selected from the group consisting of —C (═O) —, —O—, —S— and —NH—, or a group formed by bonding two or more of these.
Adjacent R ⁷¹ and R ⁷² , R ⁷³ and Q ^3, and R ⁷⁵ and R ⁷⁶ may be linked to each other to form a ring, and the ring may have a substituent.
R ⁷⁷ and R ⁷⁸ each independently represent a hydrogen atom or an arbitrary substituent.
R ⁷⁷ and R ⁷⁸ may be bonded to each other to form a ring, and the ring may have a substituent.
Moreover, the benzene ring and indole ring in the above formula (IV-3) may further have an arbitrary substituent. )

When the sulfo group is substituted in the benzene ring, indole ring, Q ³ , R ^{71 to} R ⁷⁵ and R ^{77 to} R ⁷⁸ described below in the formula (IV-3), the sulfo group is A salt may be formed with M ⁺ shown in (IV).
(For ^{R 71 ~R 73, R 75,} R 76)
R ^{71 to} R ⁷³ , R ⁷⁵ and R ⁷⁶ have the same meanings as R ^{41 to} R ⁴³ , R ⁴⁵ and R ⁴⁶ in the compound (IV), respectively. Specific examples and preferred embodiments are also the same.
(About R ⁷⁷ and R ⁷⁸ )
R ⁷⁷ and R ⁷⁸ have the same meanings as R ^{47 to} R ⁴⁸ in compound (IV), respectively. Specific examples and preferred embodiments are also the same.

(For ^{Q 3)}
Q ³ is a divalent aromatic ring group that may have a substituent, a divalent aliphatic hydrocarbon group that may have a substituent, or a divalent that may have a substituent. An aliphatic heterocyclic group, one group selected from the group consisting of —C (═O) —, —O—, —S— and —NH—, or a group formed by bonding two or more of these.
The divalent aromatic ring group has two free valences in the aromatic ring having one free valence described in the above section (for R ^{51 to} R ⁵⁶ ), and Examples include groups having 2 to 14 carbon atoms. Examples of the substituent that these groups may have include those described above in (Substituent group W ² ).
The divalent aliphatic hydrocarbon group is a linear, branched or cyclic group and is an aliphatic hydrocarbon group, the carbon number of which is usually 1 or more, and usually 8 or less, preferably Is 6 or less. Specific examples include an alkylene group having 1 to 8 carbon atoms, a cyclopentanediyl group, and a cyclohexanediyl group. Examples of the substituent that these groups may have include those described above in (Substituent group W ² ).
Examples of the divalent aliphatic heterocyclic group include piperidinyl group, pyrrolidinyl group, imidazolidinyl group, pyrazolidinyl group, piperazinyl group, morpholinyl group, indolinyl group, isoindolinyl group and the like. Examples of the substituent that these groups may have include those described above in (Substituent group W ² ).

[Molecular weight]
The molecular weight of the compound (IV) of the present invention is usually 500 or more, preferably 600 or more, and usually 5000 or less, preferably 2000 or less.
It is preferable that it is within the above-mentioned range in terms of good solubility in a solvent and easy production.

Although the preferable specific example of compound (IV) of this invention is shown below, this invention is not limited to these.
[Specific Examples of Compound (IV)]

[Synthesis method]
The compounds (II) to (IV) are described in J.I. Chem. Soc. PerkinTrans. 1998, 2,297. , International Publication No. 2006/120205, “Review Synthetic Dyes” (Horiguchi Hiroshi, Sankyo Publishing, 1968).

(Triarylmethane dyes: compounds represented by formula (V))

(In formula (V), R ^{b1 to} R ^b4 each independently represents a hydrogen atom, —R ^b6, or an aromatic hydrocarbon group having 6 to 10 carbon atoms.
R ^b5 represents —SO ₃ ^— , —SO ₃ H, —SO ₃ M, —CO ₂ H, —CO ₂ R ^b6 , —SO ₃ R ^b6 , —SO ₂ NHR ^b8 or —SO ₂ NR ^b8 R ^b9 Represent.
m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R ^b5 may be the same or different.
R ^b6 represents a saturated hydrocarbon group having 1 to 10 carbon atoms.
R ^b8 and R ^b9 each independently represent a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or -Q1.
Q1 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms.
M represents a sodium atom or a potassium atom.
D represents a halogen atom. a represents an integer of 0 or 1. )

(About R ^b6 )
As R ^b6 , methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, cycloheptyl, octyl, 2-ethylhexyl, cyclooctyl, nonyl, decanyl, tricyclodecane Nyl, methoxypropyl, ethoxypropyl, hexyloxypropyl, 2-ethylhexyloxypropyl, methoxyhexyl, ethoxypropyl and the like.

Examples of —SO ₃ R ^b6 include methanesulfonyl, ethanesulfonyl, hexanesulfonyl, decanesulfonyl, and the like.

As —CO ₂ R ^b6 , methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, isopropyloxycarbonyl, butyloxycarbonyl, isobutyloxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, cyclopentyloxycarbonyl, Hexyloxycarbonyl, cyclohexyloxycarbonyl, heptyloxycarbonyl, cycloheptyloxycarbonyl, octyloxycarbonyl, 2-ethylhexyloxycarbonyl, cyclooctyloxycarbonyl, nonyloxycarbonyl, decanyloxycarbonyl, tricyclodecanyloxycarbonyl, methoxypropyl Oxycarbonyl, ethoxypropyloxycarbonyl, f Siloxy propyl oxycarbonyl, 2-ethylhexyloxy propyloxy, methoxy hexyloxycarbonyl, and the like.

As —SO ₂ NHR ^b8 , sulfamoyl, methanesulfamoyl, ethanesulfamoyl, propanesulfamoyl, isopropanesulfamoyl, butanesulfamoyl, isobutanesulfamoyl, pentansulfamoyl, isopentanesulfamoyl, Neopentanesulfamoyl, cyclopentanesulfamoyl, hexanesulfamoyl, cyclohexanesulfamoyl, heptanesulfamoyl, cycloheptanesulfamoyl, octanessulfamoyl, 2-ethylhexanesulfamoyl, 1,5- Dimethylhexanesulfamoyl, cyclooctanesulfamoyl, nonanesulfamoyl, decanesulfamoyl, tricyclodecanesulfamoyl, methoxypropanesulfamoyl, ethoxypropanesulfur Moyl, propoxypropane sulfamoyl, isopropoxypropane sulfamoyl, hexyloxypropane sulfamoyl, 2-ethylhexyloxypropane sulfamoyl, methoxyhexanesulfamoyl, 3-phenyl-1-methylpropanesulfamoyl, etc. Is mentioned.

Examples of —SO ₂ NHR ^b8 and —SO ₂ NR ^b8 R ^b9 include groups represented by the following formulas.

In the above formula, X ¹ represents a halogen atom. Examples of the halogen atom for X ¹ include a fluorine atom, a chlorine atom, and a bromine atom.

In the above formula, X ³ represents an alkyl group or an alkoxyl group having 1 to 3 carbon atoms having 1 to 3 carbon atoms, hydrogen atoms of the alkyl group and alkoxy group may be substituted with a halogen atom.
Examples of the alkyl group having 1 to 3 carbon atoms which may be substituted with a halogen atom include methyl, ethyl, propyl, isopropyl, perfluoromethyl and the like.
Examples of the alkoxy group having 1 to 3 carbon atoms which may be substituted with a halogen atom include methoxy, ethoxy and propoxy.

In the above formula, X ² represents an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, a halogen atom or a nitro group, and the hydrogen atom of the alkyl group and the alkoxy group is substituted with a halogen atom. It may be.
Examples of the halogen atom for X ² include a fluorine atom, a chlorine atom and a bromine atom.
Examples of the alkyl group having 1 to 3 carbon atoms which may be substituted with a halogen atom include methyl, ethyl, propyl, isopropyl, perfluoromethyl and the like.
Examples of the alkoxy group having 1 to 3 carbon atoms which may be substituted with a halogen atom include methoxy, ethoxy and propoxy.

In the above formula, X ² represents the same meaning as described above.

In the above formula, X ³ represents the same meaning as described above.
As R ^b8 and R ^b9 contained in —SO ₂ NR ^b8 R ^b9 , branched alkyl groups having 6 to 8 carbon atoms, alicyclic alkyl groups having 5 to 7 carbon atoms, allyl groups, phenyl groups, carbon numbers An aralkyl group having 8 to 10 carbon atoms, a hydroxyl group-containing alkyl and aryl group having 2 to 8 carbon atoms, or an alkoxyl group-containing alkyl or aryl group having 2 to 8 carbon atoms is preferable, and 2-ethylhexyl is particularly preferable.

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl and naphthyl.
As a substituent of an aromatic hydrocarbon group having 6 to 10 carbon atoms, ethyl, propyl, phenyl, dimethylphenyl, —SO ₃ R ^b6 or —SO ₂ NHR ^b8 is preferable. As a halogen atom mentioned as a substituent of this C6-C10 aromatic hydrocarbon group, a fluorine atom, a chlorine atom, a bromine atom, etc. are mentioned.
As a substituent of an aromatic hydrocarbon group having 6 to 10 carbon atoms, ethyl, propyl, phenyl, dimethylphenyl, —SO ₃ R ^b6 or —SO ₂ NHR ^b8 is preferable.
Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, hexylphenyl, decanylphenyl, fluorophenyl, chlorophenyl, bromophenyl, hydroxyphenyl, methoxyphenyl , Dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, decanyloxyphenyl, trifluoromethylphenyl and the like.

(Method for synthesizing compound (V))
In the compound (V), for example, a dye or dye intermediate having —SO ₃ H is chlorinated by a conventional method, and the obtained dye or dye intermediate having —SO ₂ Cl is represented by R ⁸ —NH _2. It can be produced by reacting with an amine. Moreover, it can manufacture by making the pigment | dye manufactured by the method of the upper right column-lower left column of Japan Unexamined-Japanese-Patent No. 3-78702 3 pages react with an amine after chlorination like the above.

(Concrete example)
Specific examples of compound (V) are shown below.

(Cyanine dye: about the compound represented by formula (VI))
The cyanine dye is preferably a compound represented by the following formula (VI) (hereinafter sometimes referred to as “compound (VI)”) in terms of high heat resistance, light resistance, and high transmittance. .

(In the formula, Z ^m3- represents an m3-valent anion.
m3 represents an integer of 1 to 4.
Ar ¹ and Ar ² each independently represent a nitrogen-containing heterocyclic group which may have a substituent.
q represents the integer of 1-5. )

(About q)
q represents the integer of 1-5.
q is preferably 1 to 5 and particularly preferably 1 to 3 in terms of heat resistance of the coloring material.

(About Ar ¹ and Ar ² )
Ar ¹ and Ar ² each independently represent a nitrogen-containing heterocyclic group which may have a substituent.
Examples of the nitrogen-containing heterocyclic group include an indole ring, a benzoindole ring, an indolenine ring, a benzoindolenine ring, an oxazole ring, a benzoxazole ring, a thiazole ring, a benzothiazole ring, a benzo having one free valence. Examples include imidazole ring and quinoline ring. Of these, indole ring, benzoindole ring, indolenine ring, and benzoindolenine ring are preferable, and indole ring and benzoindolenine ring are more preferable in terms of high luminance.

Further, the substituent that the nitrogen-containing heterocyclic ring in Ar ¹ and Ar ² may have is not particularly limited as long as the effects of the present invention are not impaired, but a methyl group, an ethyl group, a propyl group, an isopropyl group Aliphatic hydrocarbon groups such as butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl;
Aromatic hydrocarbon groups such as phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group;
Alkoxy groups such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group;
Aryloxy groups such as phenoxy groups;
An aralkyloxy group such as a benzyloxy group;
Groups having an ester bond such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, acetoxy group, benzoyloxy group;
Methylsulfamoyl group, dimethylsulfamoyl group, ethylsulfamoyl group, diethylsulfamoyl group, n-propylsulfamoyl group, di-n-propylsulfamoyl group, isopropylsulfamoyl group, diisopropylsulfamoyl group Alkylsulfamoyl groups such as a famoyl group, n-butylsulfamoyl group, di-n-butylsulfamoyl group;
Alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group;
Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
Examples thereof include a nitro group and a cyano group.

  When the substituent has a hydrogen atom, the hydrogen atom is, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, or a butoxy group. , Isobutoxy group, sec-butoxy group, tert-butoxy group, alkoxy group such as pentyloxy group; aryloxy group such as phenoxy group, benzyloxy group; phenyl group, o-tolyl group, m-tolyl group, p-tolyl group An aromatic hydrocarbon group such as a group, xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group; carboxy group; cyano group; nitro group;

The compound represented by the formula (VI) has a cis-trans isomer at the cation site, but may be any isomer.
The compound represented by the formula (VI) is more preferably a compound represented by the following formula (VI-1) from the viewpoint of increasing the lightness and heat resistance of the coating film.

(In said formula (VI-1), n is synonymous with n in said Formula (VI).
R ⁹⁰¹ and R ⁹⁰² each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms.
R ⁹¹ and R ⁹² each independently represent —O—, —S—, —N—, —Se— or —CR ⁹⁰³ R ⁹⁰⁴ —.
R ⁹⁰³ and R ⁹⁰⁴ each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms.
However, when R ⁹¹ and R ⁹² are —CR ⁹⁰³ R ⁹⁰⁴ —, R ⁹⁰³ may be bonded to each other to form a ring. The ring may have a substituent.
Rings Y ¹ and Y ² each independently represent a benzene ring that may have a substituent or a naphthalene ring that may have a substituent.
R ⁸¹ and R ⁸² are each independently an alkyl group having 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 6 carbon atoms which may have a substituent, or a substituent. The C3-C8 cycloalkyl group which may have is represented.
R ⁸¹ and R ⁸² may be bonded to each other to form a ring. )

(About ^R901 and ^R902 )
R ⁹⁰¹ and R ⁹⁰² each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
Examples of the aliphatic hydrocarbon group include methyl group, ethyl group, vinyl group, ethynyl group, propyl group, isopropyl group, isopropenyl group, 1-propenyl group, 2-propenyl group, 2-propynyl group, butyl group, Isobutyl group, sec-butyl group, tert-butyl group, 2-butenyl group, 1,3-butadienyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1-methylpentyl group, 2-methylpentyl group 2-pentene-4-ynyl group, hexyl group, isohexyl group, 5-methylhexyl group, heptyl group and octyl group.
Examples of the substituent that the aliphatic hydrocarbon group may have include, for example, a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a xylyl group, a mesityl group, an o-cumenyl group, an aromatic hydrocarbon group such as an m-cumenyl group and a p-cumenyl group;
Alkoxy groups such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, phenoxy group, benzyloxy group;
Halogen groups such as fluoro, chloro, bromo and iodo groups;
Furthermore, a carboxy group, a nitro group, and a cyano group are mentioned.
R ⁹⁰¹ and R ⁹⁰² are each preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms.

(About R ⁹¹ and R ⁹² )
R ⁹¹ and R ⁹² each independently represent —O—, —S—, —N—, —Se— or —CR ⁹⁰³ R ⁹⁰⁴ —.
R ⁹⁰³ and R ⁹⁰⁴ each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms.
However, when R ⁹¹ and R ⁹² are —CR ⁹⁰³ R ⁹⁰⁴ —, R ⁹⁰³ may be bonded to each other to form a ring.
Preferable specific examples of the ring which R ⁹¹ and R ⁹² may be bonded to each other include, for example, the following, but the present invention is not limited thereto.

(About rings Y ¹ and Y ² )
Rings Y ¹ and Y ² each independently represent a benzene ring that may have a substituent or a naphthalene ring that may have a substituent.
The aliphatic hydrocarbon group in R ⁹⁰³ and R ⁹⁰⁴ , the ring that R ⁹¹ and R ⁹² may be bonded to each other, and the benzene ring and the naphthalene ring in rings Y ¹ and Y ² may have. As a substituent, the substituent which the aliphatic hydrocarbon group in the said ^R901 and ^R902 may have is mentioned.

(About R ⁸¹ and R ⁸² )
R ⁸¹ and R ⁸² are each independently an alkyl group having 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 6 carbon atoms which may have a substituent, or a substituent. The C3-C8 cycloalkyl group which may have is represented.
R ⁸¹ and R ⁸² may be bonded to each other to form a ring.
R ⁸¹ and R ⁸² have the same meanings as R ²¹ and R ²² in formula (II-1), and the preferred embodiments are also the same.
That is, the anion in the compound represented by the formula (VI-1) is preferably a compound represented by the formula (II′-1) or (II′-2).
The compound represented by the formula (VI) are, for ^example, from R 901 ^{to R 902} and ^{R 91} and ^{R 92,} stretched a linker, may form a like a dimer or trimer.

Although the preferable specific example of the compound represented by Formula (VI) in this invention is shown below, this invention is not limited to these.
[Concrete example]

When the colored resin composition of the present invention is a colored resin composition for forming a red pixel or a colored resin composition for forming a green pixel, a yellow dye may be used as a complementary color.
When a yellow dye is included, the image forming property and developability tend to be insufficient before the solvent resistance is lowered.
This is because when the absorption wavelength of the yellow dye and the absorption wavelength of the photopolymerization initiator overlap, the photopolymerization initiator cannot obtain sufficient light energy, and the amount of radical generation decreases, resulting in a colored resin composition. It is presumed that the photopolymerization initiator contained in the product does not function sufficiently.
That is, it is preferable that the following yellow dye is included in the colored resin composition because the effects of the present invention can be more easily obtained.
Hereinafter, the yellow dye will be described in detail.

[Yellow dye]
Examples of the yellow dye in the present invention include azo dyes, quinophthalone dyes, cyanine dyes, anthraquinone dyes, methine dyes, and dipyrromethene dyes. Of these, azo dyes are preferable.
Examples of the azo dyes include pyridone azo dyes, pyrazolone azo dyes and barbituric acid azo dyes, and in particular, pyridone azo dyes have a sharp absorption edge at an absorption spectrum of 400 nm to 500 nm, This is preferable in that a pixel with high luminance can be obtained.
The pyridone azo dye is not particularly limited, and a known substance can be used. However, a compound represented by the following formula (VII) (hereinafter referred to as “compound”) is highly soluble in the colored resin composition. VII) ”)).

(In the above formula (VII), A represents an aromatic hydrocarbon ring group which may have a substituent or a heterocyclic group which may have a substituent.
R ^1a represents a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, a carboxy group, or a trifluoromethyl group.
R ^2a represents a hydrogen atom, a cyano group, a carbamoyl group, an alkylcarbamoyl group which may have a substituent, an arylcarbamoyl group which may have a substituent, a carboxy group, a sulfamoyl group or a sulfo group.
R ^3a has a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group having 6 to 30 carbon atoms, and a substituent. May be an aralkyl group having 7 to 20 carbon atoms, an optionally substituted heterocyclic group having 3 to 20 carbon atoms, a carbamoyl group, or an optionally substituted alkyl carbamoyl group having 2 to 20 carbon atoms. An arylcarbamoyl group having 7 to 30 carbon atoms which may have a substituent, a sulfamoyl group having 1 to 20 carbon atoms, an alkylsulfamoyl group having 1 to 20 carbon atoms which may have a substituent, and a substituent. An optionally substituted arylsulfamoyl group having 6-30 carbon atoms, an optionally substituted alkyloxycarbonyl group having 2-20 carbon atoms, and an optionally substituted 7-30 carbon atoms. Aryloxycarbonyl group, substituent An optionally substituted acyl group having 2 to 30 carbon atoms, an optionally substituted alkylsulfonyl group having 1 to 30 carbon atoms or an optionally substituted aryl having 6 to 30 carbon atoms Represents a sulfonyl group. )

(About A)
A represents an aromatic hydrocarbon ring group which may have a substituent or a heterocyclic group which may have a substituent.
Examples of the aromatic hydrocarbon ring group include a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring having one free valence. Acenaphthene ring, fluoranthene ring, fluorene ring and the like.
Examples of the heterocyclic group include pyrrolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, oxazolyl group, triazolyl group, thiadiazolyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzothiazolinyl group Phthalimidoyl group, benzimidazolonyl group, furyl group, thiophenyl group and the like.
As the substituent that the aromatic hydrocarbon ring group or the heterocyclic group may have, a hydrophilic group or a color tone can be adjusted in terms of improving the solubility of the compound (I) in a solvent. A group having electron donating properties and electron withdrawing properties is preferred.

  More specifically, an alkyl group which may have a substituent, an aryl group which may have a substituent, a monovalent heterocyclic group which may have a substituent, and a substituent. An optionally substituted alkoxy group, an amino group, an optionally substituted alkylamino group, an optionally substituted arylamino group, an optionally substituted acylamino group, carbamoyl A group, an optionally substituted alkylcarbamoyl group, an optionally substituted arylcarbamoyl group, a sulfamoyl group, an optionally substituted alkylsulfamoyl group, and a substituent. Arylsulfamoyl group which may be substituted, alkyloxycarbonyl group which may have substituent, aryloxycarbonyl group which may have substituent, nitro group, carboxy group, sulfo group A hydroxyl group, a cyano group and a halogen atom.

  The alkyl group which may have a substituent has usually 1 or more, usually 12 or less, preferably 10 or less. Examples of the group that may be substituted with the alkyl group include an alkoxy group having 1 to 10 carbon atoms, a phenyl group, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, a sulfo group, and a carboxy group. Is mentioned. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, hydroxyethyl group, 1,2-dihydroxypropyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2 -(2-methoxyethoxy) ethyl group, 2- (2-ethoxyethoxy) ethyl group, 2- (2-butoxyethoxy) ethyl group, benzyl group, phenethyl group and the like can be mentioned.

  The aryl group which may have a substituent usually has 6 or more carbon atoms, usually 14 or less, and preferably 12 or less. Examples of the aryl group include a phenyl group, a naphthyl group, and an anthracenyl group. Examples of the group which may be substituted for the aryl group include an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a sulfo group, and A carboxy group etc. are mentioned. Specific examples of the aryl group include a phenyl group, a p-tolyl group, an m-tolyl group, a p-methoxyphenyl group, a naphthyl group, and an anthracenyl group.

  The monovalent heterocyclic group which may have a substituent usually has 2 or more carbon atoms and usually 14 or less, preferably 12 or less. Examples of the monovalent heterocyclic group include pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, triazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, benzothiazolinyl Group, phthalimidoyl group, benzimidazolonyl group, furyl group, thiophenyl group, pyranyl group, piperidinyl group, pyrrolidinyl group, imidazolidinyl group, pyrazolidinyl group, piperazinyl group, morpholinyl group, indolinyl group, isoindolinyl group and the like. Examples of the group that may be substituted on the monovalent heterocyclic group include an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, and a halogen atom. , Sulfo group and carboxy group. Specific examples of the monovalent heterocyclic group include a 2-pyrrolyl group, a 2-imidazolyl group, a 1-pyrazolyl group, a 2-thiazolyl group, a 2-oxazolyl group, a 1,2,4-triazol-1-yl group, 4-pyridinyl group, 2-pyrimidinyl group, 4,6-diamino-2-triazinyl group, 8-quinolinyl group, 8-isoquinolinyl group, 2-benzothiazolinyl group, 6-methyl-7-sulfo-2-benzo Thiazolinyl group, 1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl group, 1H-benzimidazol-2-yl group, 2-furyl group, 2-thiophenyl group, 1-piperidinyl Group, 1-pyrrolidinyl group, 1-imidazolidinyl group, 1-pyrazolidinyl group, 1-piperazinyl group, 1-morpholinyl group, 1-indolinyl group, 2-isoindolinyl group It is below.

  The alkoxy group which may have a substituent usually has 1 or more carbon atoms and usually 12 or less, preferably 10 or less. Examples of the group which may be substituted for the alkoxy group include an alkoxy group having 1 to 10 carbon atoms, a phenyl group, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, a sulfo group, and a carboxy group. Is mentioned. Specific examples of the alkoxy group include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, hydroxyethoxy group, 1,2-dihydroxypropoxy group, 2-methoxyethoxy group, 2-ethoxyethoxy group, 2- Examples include butoxyethoxy group, 2- (2-methoxyethoxy) ethoxy group, 2- (2-ethoxyethoxy) ethoxy group, 2- (2-butoxyethoxy) ethoxy group, benzyloxy group, phenethyloxy group and the like.

The alkylamino group which may have a substituent is represented by —NR ^11a R ^12a , R ^11a represents an alkyl group which may have a substituent, and R ^12a represents a hydrogen atom or a substituent. It represents an alkyl group that may have. The alkyl group usually has 1 or more carbon atoms and usually 12 or less, preferably 10 or less. Examples of the group that may be substituted with the alkyl group include an alkoxy group having 1 to 10 carbon atoms, a phenyl group, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, a sulfo group, and a carboxy group. Is mentioned. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, cyclohexyl group, hydroxyethyl group, 1,2-dihydroxypropyl group, 2-methoxyethyl group, 2-ethoxyethyl group. 2-butoxyethyl group, 2- (2-methoxyethoxy) ethyl group, 2- (2-ethoxyethoxy) ethyl group, 2- (2-butoxyethoxy) ethyl group, benzyl group, phenethyl group and the like. Specific examples of the alkylamino group include an ethylamino group, a dimethylamino group, a diethylamino group, a dibutylamino group, a di (2-ethoxyethyl) amino group, a diphenethylethylamino group, and a cyclohexylethyl group.

The arylamino group which may have a substituent is represented by —NR ^13a R ^14a , R ^13a represents an aryl group which may have a substituent, and R ^14a represents a hydrogen atom or a substituent. The alkyl group which may have and the aryl group which may have a substituent are represented. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. The aryl group usually has 6 or more carbon atoms and usually 14 or less, preferably 12 or less, and examples thereof include a phenyl group, a naphthyl group, and an anthracenyl group. Examples of the group which may be substituted on the aryl group include an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, A sulfo group, a carboxy group, etc. are mentioned. Specific examples of the aryl group include a phenyl group, a p-tolyl group, an m-tolyl group, a p-methoxyphenyl group, a naphthyl group, and an anthracenyl group. Specific examples of the arylamino group include a phenylamino group, a diphenylamino group, a di (p-tolyl) amino group, a di (p-methoxyphenyl) amino group, an ethylphenylamino group, and an n-butylphenylamino group. Can be mentioned.

The acylamino group which may have a substituent is represented by -NH-COR ^15a , and R ^15a represents an alkyl group which may have a substituent or an aryl group which may have a substituent. . The preferred carbon number of the alkyl group and examples of the substituent which may be present are the same as those exemplified for the alkyl group of R ^11a and R ^12a . Examples of the preferable carbon number of the aryl group and the substituent that may be included are the same as the substituent that the aryl group of R ^13a may have. Specific examples of the acylamino group include acetylamino group, benzoylamino group, 2-ethylhexylcarbonylamino group and the like.

An optionally substituted alkylcarbamoyl group ^is represented by ^{-CO-NR 16a R 17a, R} 16a and ^{R 17a} each independently represent a hydrogen atom or an optionally substituted alkyl group Represents. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Specific examples of the alkylcarbamoyl group include a methylcarbamoyl group, an ethylcarbamoyl group, a phenethylcarbamoyl group, a 2-ethylhexylcarbamoyl group, a 2-ethoxyethylcarbamoyl group, a 2- (2-ethoxyethoxy) ethylcarbamoyl group, and the like. .

The arylcarbamoyl group which may have a substituent is represented by —CO—NR ^18a R ^19a , and R ^18a represents an aryl group which may have a substituent. R ^19a represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ^13a . Specific examples of the arylcarbamoyl group include phenylcarbamoyl group, naphthylcarbamoyl group, p-tolylcarbamoyl group, p-methoxyphenylcarbamoyl group and the like.

The alkylsulfamoyl group which may have a substituent is represented by —SO ₂ —NR ^20a R ^21a , and R ^20a and R ^21a may each independently have a hydrogen atom or a substituent. Represents a good alkyl group. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Specific examples of the alkylsulfamoyl group include methylsulfamoyl group, ethylsulfamoyl group, phenethylsulfamoyl group, 2-ethylhexylsulfamoyl group, 2-ethoxyethylsulfamoyl group, 2- ( And 2-ethoxyethoxy) ethylsulfamoyl group.

The arylsulfamoyl group which may have a substituent is represented by —SO ₂ —NR ^22a R ^23a , and R ^22a represents an aryl group which may have a substituent. R ^23a represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ^13a . Specific examples of the arylsulfamoyl group include a phenylsulfamoyl group, a naphthylsulfamoyl group, a p-tolylsulfamoyl group, and a p-methoxyphenylsulfamoyl group.

The alkyloxycarbonyl group which may have a substituent is represented by —CO—OR ^24a , and R ^24a represents an alkyl group which may have a substituent. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Specific examples of the alkyloxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a phenethyloxycarbonyl group, a 2-ethylhexyloxycarbonyl group, a 2-ethoxyethoxycarbonyl group, and a 2- (2-ethoxyethoxy) ethoxycarbonyl group. Is mentioned.

The aryloxycarbonyl group which may have a substituent is represented by —CO—OR ^25a , and R ^25a represents an aryl group which may have a substituent. Examples of the preferable number of carbon atoms of the aryl group and the substituent that may be included are the same as the substituent that the aryl group in R ^23a may have. Specific examples of the aryloxycarbonyl group include phenoxycarbonyl group, naphthoxycarbonyl group, p-tolyloxycarbonyl group, p-methoxyphenoxycarbonyl group and the like.

  Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and among them, a fluorine atom and a chlorine atom having high electronegativity are preferable.

(About R ^1a )
R ^1a represents a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, a carboxy group, or a trifluoromethyl group.
The alkyl group which may have a substituent has usually 1 or more, usually 10 or less, preferably 5 or less. Examples of the group that may be substituted on the alkyl group include an alkoxy group having 1 to 8 carbon atoms and a hydroxyl group. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, hydroxyethyl group, methoxymethyl group and the like.

(About R ^2a )
R ^2a represents a hydrogen atom, a cyano group, a carbamoyl group, an alkylcarbamoyl group which may have a substituent, an arylcarbamoyl group which may have a substituent, a carboxy group, a sulfamoyl group or a sulfo group.
The alkylcarbamoyl group which may have a substituent is represented by —CO—NR ^56a R ^57a , and R ^56a and R ^57a each independently represent a hydrogen atom or an alkyl group which may have a substituent. Represents. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Specific examples of the alkylcarbamoyl group include a methylcarbamoyl group, an ethylcarbamoyl group, a phenethylcarbamoyl group, a 2-ethylhexylcarbamoyl group, a 2-ethoxyethylcarbamoyl group, a 2- (2-ethoxyethoxy) ethylcarbamoyl group, and the like. .

Which may have a substituent arylcarbamoyl group ^is represented by ^{-CO-NR 58a R 59a, R} 58a represents an aryl group which may have a substituent. R ^59a represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ^13a . Specific examples of the arylcarbamoyl group include phenylcarbamoyl group, naphthylcarbamoyl group, p-tolylcarbamoyl group, p-methoxyphenylcarbamoyl group and the like.

(About R ^3a )
R ^3a has a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group having 6 to 30 carbon atoms, and a substituent. May be an aralkyl group having 7 to 20 carbon atoms, an optionally substituted heterocyclic group having 3 to 20 carbon atoms, a carbamoyl group, or an optionally substituted alkyl carbamoyl group having 2 to 20 carbon atoms. An arylcarbamoyl group having 7 to 30 carbon atoms which may have a substituent, a sulfamoyl group having 1 to 20 carbon atoms, an alkylsulfamoyl group having 1 to 20 carbon atoms which may have a substituent, and a substituent. An optionally substituted arylsulfamoyl group having 6-30 carbon atoms, an optionally substituted alkyloxycarbonyl group having 2-20 carbon atoms, and an optionally substituted 7-30 carbon atoms. Aryloxycarbonyl group, substituent An optionally substituted acyl group having 2 to 30 carbon atoms, an optionally substituted alkylsulfonyl group having 1 to 30 carbon atoms or an optionally substituted aryl having 6 to 30 carbon atoms Represents a sulfonyl group.

  The alkyl group having 1 to 20 carbon atoms which may have a substituent has usually 1 or more, usually 20 or less, preferably 15 or less. Examples of the group that may be substituted on the alkyl group include an alkoxy group having 1 to 15 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, a sulfo group, and a carboxy group. . Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, hydroxyethyl group, 1,2-dihydroxypropyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2 -(2-methoxyethoxy) ethyl group, 2- (2-ethoxyethoxy) ethyl group, 2- (2-butoxyethoxy) ethyl group and the like can be mentioned.

  The aryl group having 6 to 30 carbon atoms which may have a substituent usually has 6 or more carbon atoms, usually 30 or less, preferably 25 or less. Examples of the aryl group include a phenyl group, a naphthyl group, and an anthracenyl group. Examples of the group that may be substituted on the aryl group include an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a sulfo group, and A carboxy group etc. are mentioned. Specific examples of the aryl group include a phenyl group, a p-tolyl group, an m-tolyl group, a p-methoxyphenyl group, a naphthyl group, and an anthracenyl group.

  The aralkyl group having 7 to 20 carbon atoms which may have a substituent usually has 7 or more carbon atoms, usually 20 or less, preferably 15 or less. Examples of the group that may be substituted for the aralkyl group include an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a sulfo group, and A carboxy group etc. are mentioned. Specific examples of the aryl group include benzyl group, phenethyl group, α-methylbenzyl group, α-methylphenylethyl group, β-methylphenylethyl group, fluorenyl group and the like.

  The C3-C20 heterocyclic group which may have a substituent usually has 3 or more carbon atoms, usually 20 or less, and preferably 15 or less. Examples of the monovalent heterocyclic group include pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, triazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, benzothiazolinyl Group, phthalimidoyl group, benzimidazolonyl group, furyl group, thiophenyl group and the like. Examples of the group that may be substituted on the monovalent heterocyclic group include an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, and a halogen atom. , Sulfo group and carboxy group. Specific examples of the monovalent heterocyclic group include a 2-pyrrolyl group, a 2-imidazolyl group, a 1-pyrazolyl group, a 2-thiazolyl group, a 2-oxazolyl group, a 1,2,4-triazol-1-yl group, 4-pyridinyl group, 2-pyrimidinyl group, 4,6-diamino-2-triazinyl group, 8-quinolinyl group, 8-isoquinolinyl group, 2-benzothiazolinyl group, 6-methyl-7-sulfo-2-benzo Examples include thiazolinyl group, 1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl group, 1H-benzimidazol-2-yl group, 2-furyl group, and 2-thiophenyl group.

Alkylcarbamoyl group having carbon atoms of 2 to 20 which may have a substituent group ^is represented by ^{-CO-NR 60a R 61a, R} 60a and ^{R 61a} each independently a hydrogen atom or a substituent Represents an optionally substituted alkyl group. The preferred carbon number of the alkyl group and examples of the substituent which may be present are the same as those exemplified for the alkyl group of R ^11a and R ^12a . Specific examples of the alkylcarbamoyl group include a methylcarbamoyl group, an ethylcarbamoyl group, a phenethylcarbamoyl group, a 2-ethylhexylcarbamoyl group, a 2-ethoxyethylcarbamoyl group, a 2- (2-ethoxyethoxy) ethylcarbamoyl group, and the like. .

The arylcarbamoyl group having 7 to 30 carbon atoms which may have a substituent is represented by —CO—NR ^62a R ^63a , and R ^62a represents an aryl group which may have a substituent. R ^63a represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ^13a . Specific examples of the arylcarbamoyl group include phenylcarbamoyl group, naphthylcarbamoyl group, p-tolylcarbamoyl group, p-methoxyphenylcarbamoyl group and the like.

Substituents alkylsulfamoyl group having 1 to 20 carbon atoms which may have a _is represented by ^{-SO 2 -NR 64a R 65a, R} 64a and ^{R 65a} each independently represent a hydrogen atom or a substituent Represents an alkyl group which may have Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Specific examples of the alkylfurfamoyl group include a methylsulfamoyl group, an ethylsulfamoyl group, a phenethylsulfamoyl group, a 2-ethylhexylsulfamoyl group, a 2-ethoxyethylsulfamoyl group, 2- ( And 2-ethoxyethoxy) ethylsulfamoyl group.

The arylsulfamoyl group having 6 to 30 carbon atoms which may have a substituent is represented by —SO ₂ —NR ^66a R ^67a , and R ^66a represents an aryl group which may have a substituent. . R ^67a represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ^13a . Specific examples of the arylsulfamoyl group include a phenylsulfamoyl group, a naphthylsulfamoyl group, a p-tolylsulfamoyl group, and a p-methoxyphenylsulfamoyl group.

Alkyloxycarbonyl group having carbon atoms of 2 to 20 which may have a substituent group is represented by ^{-CO-OR 68a, R 68a} represents an alkyl group which may have a substituent. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Specific examples of the alkyloxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a phenethyloxycarbonyl group, a 2-ethylhexyloxycarbonyl group, a 2-ethoxyethoxycarbonyl group, and a 2- (2-ethoxyethoxy) ethoxycarbonyl group. Is mentioned.

The aryloxycarbonyl group having 7 to 30 carbon atoms which may have a substituent is represented by —CO—OR ^69a , and R ^69a represents an aryl group which may have a substituent. Examples of the preferable number of carbon atoms of the aryl group and the substituent that may be included are the same as the substituent that the aryl group in R ^23a may have. Specific examples of the aryloxycarbonyl group include phenoxycarbonyl group, naphthoxycarbonyl group, p-tolyloxycarbonyl group, p-methoxyphenoxycarbonyl group and the like.

Optionally substituted acyl group having a carbon number of 2 to 30 is represented by ^{-COR 70a,} R ^70a is an optionally substituted alkyl group, which may have a substituent Represents an aryl group. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ^13a . Specific examples of the acyl group include an acetyl group, a benzoyl group, and a 2-ethylhexylcarbonyl group.

The alkylsulfonyl group having 1 to 30 carbon atoms which may have a substituent is represented by —SO ₂ —R ^71a , and R ^71a represents an alkyl group which may have a substituent. Examples of the preferred carbon number of the alkyl group and the substituent that may be present are the same as the substituent that the alkyl group in R ^11a and R ^12a may have. Specific examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a phenethylsulfonyl group, a 2-ethylhexylsulfonyl group, a 2-ethoxyethylsulfonyl group, and a 2- (2-ethoxyethoxy) ethylsulfonyl group. .

The arylsulfonyl group having 6 to 30 carbon atoms which may have a substituent is represented by —SO ₂ —R ^72a , and R ^72a represents an aryl group which may have a substituent. Examples of the preferable number of carbon atoms of the aryl group and the substituent that may be included are the same as the substituent that the aryl group in R ^23a may have. Specific examples of the arylsulfonyl group include a phenylsulfonyl group, a naphthylsulfonyl group, a p-tolylsulfonyl group, and a p-methoxyphenylsulfonyl group.

[Specific Example of Compound (VII)]
Although the preferable specific example of compound (VII) is shown below, this invention is not limited to these.

  In addition to the above structure, Japanese Patent Laid-Open No. 2002-14223, Japanese Patent Laid-Open No. 2005-126529, Japanese Patent Laid-Open No. 2005-226622, Japanese Patent Laid-Open No. 2006-58701, Japanese Patent Laid-Open No. 2006-124634 Japan JP 2009-280691, JP 2009-299030, JP 2010-1469, JP 2010-152160, JP 2010-168531, Japan Special Pyridone azo dyes described in JP2010-275533, JP-A-2011-148899, JP-A-2011-148990, JP-A-2011-148991, JP-A-2011-148992, Complexed pyridone azo dyes described in JP 2011-148993 A and JP Examples thereof include polymerized pyridone azo dyes described in Japanese Patent Application Laid-Open No. 2006-265495, and dimerized pyridone azo dyes described in Japanese Patent Application Laid-Open Nos. 2010-170073 and 2010-275531. .

[Other color materials]
The colored resin composition of the present invention contains (A) a dye as a colorant, and other colorants can be used in combination with the dye.
Examples of other colorants include pigments and the like, which can be appropriately combined depending on the color of a desired pixel.

For example, when forming a blue pixel, when the dye contains the compound (II) or (VI), a violet pigment is preferably used as the pigment that can be used in combination.
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. Of these, C.I. I. Pigment violet 19, 23, etc., more preferably C.I. I. Pigment violet 23 and the like.

Moreover, when forming a blue pixel, when a dye contains compound (III)-(V), as a pigment which can be used together, a blue pigment is used suitably.
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.

Moreover, when forming a green pixel, when a dye contains a compound (VII), a green pixel is used suitably as a pigment which can be used together.
Examples of green pigments include C.I. I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, 58 and the like. Of these, C.I. I. Pigment green 7, 36, 58, and the like.
In particular, C.I. I. When the pigment green 58 is used, it is preferable in that the effects of the present invention can be easily obtained.

  In addition, a yellow pigment or a red pigment may be included as appropriate. As these pigments, for example, pigments described in Japanese Patent Application Laid-Open No. 2009-25813 can be used.

When the color material contains a pigment, the average primary particle diameter of the pigment is usually 100 nm or less, preferably 80 nm or less, more preferably 20 nm or more and 70 nm or less. Since the present invention is particularly effective in the case of a composition containing a highly atomized pigment, the case of containing a pigment having an average primary particle size of 20 nm to 60 nm is particularly preferable.
By keeping the average primary particle size of the pigment used in the above range, the depolarization characteristics are kept good, high contrast and transmittance are realized, dispersion stability is good, and heat resistance and light resistance are also improved. An excellent pigment dispersion and colored resin composition can be obtained.

The primary particle diameter of the pigment can be determined by the following method.
First, the 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). However, in the case of organic pigments, the particle diameter of each pigment particle is the diameter corresponding to the area circle converted to the diameter of a circle having the same area, and the particle diameter of each of plural (usually about 200 to 300) pigment particles. Ask for. 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 pigment thus obtained may be used alone, but one or two or more pigments can be mixed and used within a range not impairing the effects of the present invention.

(Coloring material content)
The content of the color material contained in the colored resin composition of the present invention varies depending on the color of the desired pixel. For example, the total content of the (A) dye and other color material is based on the total solid content. It is usually 1% by weight or more, preferably 3% by weight or more, more preferably 5% by weight or more, and usually 50% by weight or less, more preferably 40% by weight or less, more preferably 30% by weight or less.
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 it is difficult to place reaggregation or thickening.

[(B) Solvent]
The (B) solvent in the present invention has a function of adjusting the viscosity by dissolving or dispersing each component contained in the colored resin composition.
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, propylene glycol-mono t-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, methoxymethylpentanol, propylene Glycol monoalkyl ethers such as 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, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, 3-methoxybutyl acetate, methoxypentyl acetate, diethylene glycol monoethyl Glycol alkyl ether acetates such as 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;
Nitriles such as acetonitrile and benzonitrile:

  Commercially available solvents corresponding to the above include mineral spirit, Barsol # 2, Apco # 18 Solvent, Apco thinner, Soal Solvent No. 1 and no. 2, Solvesso # 150, Shell TS28 Solvent, carbitol, ethyl carbitol, butyl carbitol, methyl cellosolve, ethyl cellosolve, ethyl cellosolve acetate, methyl cellosolve acetate, diglyme (all trade names) and the like.

  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.

  In addition, for example, when a pigment described later is included as an optional component, glycol alkyl ether acetates are further used as a solvent from the viewpoint that the balance of coatability, surface tension, etc. is good and the solubility of the constituent components in the composition is relatively high. It is more preferable to use a mixture of these. 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. .

  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. .

  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.

[(C) Binder resin]
(C) The preferred resin for the binder resin differs depending on the curing means.
When the colored resin composition of the present invention is a photopolymerizable resin composition, examples of the (C) binder resin include Japanese Patent Application Laid-Open No. 7-207211, Japanese Patent Application Laid-Open No. 8-259876, and Japanese Patent Application Laid-Open No. H10-10. Polymers described in JP-A-11-30144, JP-A-11-140144, JP-A-11-174224, JP-A-2000-56118, JP-A-2003-233179, etc. Although compounds can be used, the following resins (C-1) to (C-5) are preferred among them.

(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. This is the same as that described in JP 2009-025813 A as the same item. 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 each 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.

  The “other radical polymerizable monomer” other than the mono (meth) acrylate having the structure represented by the formula (8) is styrene in that the heat resistance and strength of the colored resin composition 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, Meth) acrylic acid-2-hydroxyethyl, 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 strength 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. The structure of such a resin is described in, for example, Japanese Patent Application Laid-Open No. 8-297366 and Japanese Patent Application Laid-Open No. 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. If the molecular weight is less than 3000, heat resistance and film strength may be inferior, and if it exceeds 100,000, the solubility in a developer tends to be insufficient. 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.
(C) Content of binder resin is 0.1-80 weight% normally in a total solid, Preferably it is 1-60 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.

[(E) Polymerizable monomer]
The colored resin composition of the present invention preferably contains (E) a polymerizable monomer because the crosslink density in the film can be easily controlled.
(E) Although a well-known material can be used as a polymerizable monomer, It is preferable that it is a compound which has an ethylenically unsaturated double bond at the point that the dark reactivity in a colored resin composition is low.
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 (E) 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.

  Examples of the ethylenic compound include unsaturated carboxylic acid such as (meth) acrylic acid; ester of monohydroxy compound and unsaturated carboxylic acid; ester of aliphatic polyhydroxy compound and unsaturated carboxylic acid; aromatic polyhydroxy An ester of a compound and an unsaturated carboxylic acid; an ester obtained by an esterification reaction of an unsaturated carboxylic acid with a polyvalent carboxylic acid and a polyvalent hydroxy compound such as the above-mentioned aliphatic polyhydroxy compound or aromatic polyhydroxy compound; And an ethylenic compound having a urethane skeleton obtained by reacting an isocyanate compound with 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, etc. 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 is not necessarily a single substance but may be 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, an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid is preferable, pentaerythritol or (meth) acrylic ester of dipentaerythritol is more preferable, and dipentaerythritol hexa (meth) acrylate is particularly preferable.

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 (E) 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. If the acid value of this polyfunctional monomer is too low, the development and dissolution properties tend to be lowered, and if it is too high, production and handling may be difficult, and photopolymerization performance may deteriorate, and the surface smoothness of the pixel, etc. Curability may be inferior. Accordingly, when two or more polyfunctional monomers having different acid groups are used in combination, or when a polyfunctional monomer having no acid group is used in combination, the acid groups as the entire polyfunctional monomer should be adjusted so as to fall within the above range. Is preferred.

  In the present invention, more preferred polyfunctional monomers having acid groups are dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, and succinic acid ester of dipentaerythritol pentaacrylate, which are commercially available as “TO1382” manufactured by Toagosei Co., Ltd. It is a mixture containing the 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 these (E) polymerizable monomers 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 (E) polymerizable monomer to the total colorant including the aforementioned (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%. It is usually not more than 200% by weight, preferably not more than 100% by weight, more preferably not more than 80% by weight.

  If it is within the above range, the light effect is sufficient, and it is difficult to cause adhesion failure at the time of development, and the cross section after development is difficult to have a reverse taper shape. It is preferable in that a defect or the like hardly occurs.

[(F) Photopolymerization initiation component and / or thermal polymerization initiation component]
The colored resin composition of the present invention preferably contains at least one of (F) a photopolymerization initiation component and 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 (E), 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 (F) as a photopolymerization initiation component refers to a photopolymerization initiator (hereinafter arbitrarily referred to as (F1) component) and a polymerization accelerator (hereinafter arbitrarily referred to as (F2) component). , Means a mixture in which an additive such as a sensitizing dye (hereinafter, arbitrarily referred to as component (F3)) is used in combination.

(Photopolymerization initiation component)
The colored resin composition of the present invention preferably contains (F) a photopolymerization initiation component. The photopolymerization initiating component is usually used as a mixture of (F1) a photopolymerization initiator and an additive such as (F2) a polymerization accelerator and (F3) 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 the photopolymerization initiator (F1) constituting the photopolymerization initiating component include, for example, titanocene derivatives described in JP-A-59-152396, JP-A-61-151197, and the like; Hexaarylbiimidazole derivatives described in JP-A-10-300922, JP-A-11-174224, JP-A-2000-56118, etc .; described in JP-A-10-39503, etc. Halomethylated oxadiazole derivatives, halomethyl-s-triazine derivatives, N-aryl-α-amino acids such as N-phenylglycine, N-aryl-α-amino acid salts, N-aryl-α-amino acid esters Radical activators such as α-aminoalkylphenone derivatives; Okis described in JP-A No. 2000-80068, etc. Muesuteru based derivatives, and the like.

Specific examples include photopolymerization initiators described in International Publication No. 2009/107734.
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 the like.

  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 (F2) 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.

  These (F1) photopolymerization initiators and (F2) polymerization accelerators may be used alone or in combination of two or more.

  Further, (F3) 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, JP-A-4-219756, and the like; Coumarin dyes having a heterocyclic ring as described in JP-A-3-239703, JP-A-5-289335, etc .; JP-A-3-239703, JP-A-5-289335 3-ketocoumarin dyes described in JP-A-6-19240; pyromethene dyes described in JP-A-6-19240; JP-A-47-2528, JP-A-54-155292, JP-B-45 No. 37737, Japanese Patent Publication No. 48-84183, Japanese Patent Publication No. 52-112681, Japanese Unexamined Patent Publication No. 58-15503, Japanese Unexamined Patent Publication No. 60-88005, Japanese Special Sho 59-56403, Japanese Unexamined Patent Publication No. 2-69, Japanese Unexamined Patent Publication No. 57-168088, Japanese Unexamined Patent Publication No. 5-107761, Japanese Unexamined Patent Publication No. 5-210240, Japanese Unexamined Patent Publication No. 4-288818. And dyes having a dialkylaminobenzene skeleton described in each publication.

  (F3) 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 (F) photopolymerization initiating components is usually 0.1% by weight or more, preferably 0.2% by weight or more, more preferably 0.8% by weight based on 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, it is preferable in that the sensitivity to the exposure light beam is good, the solubility of the unexposed portion in the developer is sufficient, and poor development is unlikely to occur.

(Thermal polymerization initiation component)
Specific examples of the thermal polymerization initiation component (thermal polymerization initiator) that may be contained in the colored resin composition of the present invention include azo compounds, organic peroxides, and hydrogen peroxide. Of these, azo compounds are preferably used. More specifically, for example, a thermal polymerization initiator described in International Publication No. 2009/107734 can be used.
These thermal polymerization initiators may be used individually by 1 type, and may use 2 or more types together.

[Optional ingredients]
The colored resin composition of the present invention includes a surfactant, an organic carboxylic acid and / or an organic carboxylic acid anhydride, a thermosetting compound, a plasticizer, and the above-described (A) according to the present invention, in addition to the components described above. It may contain dyes other than dyes, thermal polymerization inhibitors, storage stabilizers, surface protective agents, adhesion improvers, development improvers and the like. Moreover, when a pigment is contained as a coloring matter, a dispersant or a dispersion aid may be contained. As these optional components, for example, various compounds described in Japanese Patent Application Laid-Open No. 2007-113000 can be used.

[Dispersant]
When the colored resin composition of this invention contains a pigment, it is preferable to contain a dispersing agent further.
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 a block copolymer include those described in Japanese Patent Application Laid-Open No. 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 Japanese Patent Application Laid-Open No. 2006-343648, for example.

When the colored resin composition of the present invention contains a pigment, the content of the dispersant in the total solid content is 2 to 1000% by weight, particularly 5 to 500% by weight, especially 10 to 250% by weight of the total content of the pigment. It is preferable to use so that it may become in the range of weight%.
By setting it within the above range, 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.

[Dispersion aid]
The colored resin composition of the present invention may contain a dispersion aid. The dispersion aid here may be a pigment derivative. Examples of the pigment derivative include Japanese Patent Laid-Open No. 2001-220520, Japanese Patent Laid-Open No. 2001-271004, and Japanese Patent Laid-Open No. 2002-179976. Various compounds described in Japanese Patent Laid-Open No. 2007-113000 and Japanese Patent Laid-Open No. 2007-186861 can be used.

  The content of the dispersion aid in the colored resin composition of the present invention is usually 0.1% by weight or more, usually 30% by weight or less, preferably 20% by weight or less, based on the total solid content of the pigment. Preferably it is 10 weight% or less, More preferably, it is 5 weight% or less. By controlling the addition amount within the above range, it is preferable in that the effect as a dispersion aid is exhibited and the dispersibility and dispersion stability are better.

[Dispersion resin]
The colored resin composition of the present invention may contain a part or all of the resin selected from the (C) binder resin or other binder resins as the following dispersion resin.
Specifically, in [Preparation Method of Colored Resin Composition], which will be described later, by adding (C) binder resin together with the components such as the above-mentioned dispersant, the (C) binder resin is combined with the dispersant. A synergistic effect contributes to the dispersion stability of the pigment. As a result, the amount of dispersant added may be reduced, which is preferable. Further, it is preferable because the developability is improved, the undissolved matter does not remain in the non-pixel portion of the substrate, and the adhesion of the pixel to the substrate is improved.
Thus, the (C) binder resin used in the dispersion treatment step may be referred to as a dispersion resin. The dispersion resin is preferably used in an amount of about 0 to 200% by weight, more preferably about 10 to 100% by weight, based on the total amount of the pigment in the colored resin composition.

[Preparation Method of Colored Resin Composition]
In the present invention, the colored resin composition can be prepared by an appropriate method. For example, (D) a chain transfer agent containing (A) a dye, (C) a binder resin, and compound (I), B) It can be prepared by mixing with a solvent and other additives.
In addition to (A) the dye, a preparation method in the case of further containing a pigment is as follows. In the solvent containing the pigment, in the presence of a dispersing agent and, if necessary, a dispersing aid, (C) a binder. Together with a part of the resin, for example, a paint shaker, a sand grinder, a ball mill, a roll mill, a stone mill, a jet mill, a homogenizer or the like is used to prepare a colored dispersion by mixing and dispersing while pulverizing. (A) a dye, (C) a binder resin, (D) a chain transfer agent, and (E) a polymerizable monomer, (F) a photopolymerization initiator and a thermal polymerization initiator, if necessary. A method of preparing by adding an additive such as at least one and mixing 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. This colored resin composition is supplied onto the substrate to form components such as a color filter, a liquid crystal display device, and an organic EL display device.
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 color filter, and a liquid crystal display device (panel) and an organic EL display device using 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.

For example, visible rays, ultraviolet rays, far ultraviolet rays, electron beams, X-rays, and the like can be used as the radiation used when forming the pixels, but radiation having a wavelength in the range of 190 to 450 nm is preferable.
The light source used for image exposure for using radiation having a wavelength of 190 to 450 nm is not particularly limited. 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 color display, a liquid crystal display device, or the like. 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 photolithography 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 in accordance with 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 including 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.

<About the colored resin composition for forming a blue pixel>
[Synthesis of dyes]
(Synthesis of Compound A)

(Reaction 1)
Compound 2 (5.02 g, 20 mmol), Compound 1 (14 ml, 80 mmol), sodium t-butoxy (7.53 g, 80 mmol), toluene (100 ml), palladium (II) acetate (0.55 g, 2.45 mmol), A mixture of tri-t-butylphosphine (10% hexane solution, 10 g, 4.94 mmol) was heated to reflux under nitrogen for 10 hours. After cooling to room temperature, water was added and the mixture was filtered through celite. The filtrate was extracted with toluene and washed with water. The toluene layer was concentrated under reduced pressure, purified by silica gel column chromatography (silica gel 500 g, hexane / ethyl acetate 10 / 1-8 / 1-6 / 1), and the resulting powder was washed with cold methanol to give compound A (4 .59, 53% yield).

(Synthesis Example 1: Synthesis of Dye (1))

(Reaction 2)
Phosphorus oxychloride (12.2 ml, 134 mmol) was added to a mixture of compound A (39 g, 89.3 mmol), compound 3 (18.5 g, 89.3 mmol) and toluene (120 ml), and the mixture was heated to reflux for 3.5 hours. After returning to room temperature, water was added and the mixture was extracted with chloroform, and the chloroform layer was washed three times with saturated brine. The product was purified by silica gel column chromatography (silica gel 300 g, chloroform / methanol 15/1), and the obtained solid was washed with hexane to obtain compound B (54.8 g, yield 93%).

(Reaction 3)
A mixture of Compound B (29 g, 43.8 mmol), lithium bis (trifluoromethanesulfonyl) imide (12.6 g, 43.8 mmol) and methanol (175 ml) was stirred at 50 ° C. for 1.5 hours. After concentration under reduced pressure, the obtained solid was washed with methanol / water = 1/2 to obtain Dye (1) (33.59 g, yield 84.5%).

(Synthesis Example 2: Synthesis of Dye (2))

(Reaction 4)
Phosphorous oxychloride (15 ml, 164 mmol) was added to a mixture of compound 4 (35.4 g, 109 mmol), compound 3 (22.6 g, 109 mmol) and toluene (200 ml), and the mixture was heated to reflux for 4 hours. After returning to room temperature, water was added and the mixture was extracted with chloroform, and the chloroform layer was washed three times with saturated brine. The product was purified by silica gel column chromatography (silica gel 300 g, chloroform / methanol 10/1 to 8/1), and the resulting solid was washed with hexane to obtain compound C (20 g, yield 33%).

(Reaction 5)
A mixture of compound C (18 g, 32.7 mmol), lithium bis (trifluoromethanesulfonyl) imide (9.4 g, 32.7 mmol) and methanol (60 ml) was stirred at 50 ° C. for 1 hour. After concentration under reduced pressure, the obtained solid was washed with methanol / water = 1/2 to obtain Dye (2) (17.7 g, yield 68%).

(Synthesis Example 3: Synthesis of Dye (3))

  Compound 5 (6.0 g, 25 mmol: synthesized by the method described in International Publication No. 2008/003604), Compound 6 (6.4 ml, 50 mmol: manufactured by Tokyo Chemical Industry Co., Ltd.), potassium carbonate (6.9 g, 50 mmol), N -A mixture of methyl-2-pyrrolidone (25 ml) was heated and stirred at 110-125 ° C for 4 hours. After cooling to room temperature, water was added and extracted with toluene. The toluene layer was washed with dilute hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. Concentration under reduced pressure gave 9.2 g of a light brown oil. This was dissolved in ethanol (40 ml), a solution of sodium hydroxide (2 g, 52.3 mmol) in water (25 ml) was added, and the mixture was stirred at 85 ° C. for 1 hr. The mixture was allowed to cool and extracted with toluene, and the toluene layer was washed with saturated brine and dried over anhydrous sodium sulfate. Concentration under reduced pressure and purification by silica gel column chromatography (hexane / ethyl acetate = 3/1) gave compound 7 (5.95 g, yield 94%) as a white powder.

  Compound 8 (1.47 g, 4.34 mmol: synthesized by the method described in WO2009 / 107734), Compound 7 (1.1 g, 4.34 mmol), toluene (30 ml), phosphorus oxychloride (0.6 ml) The mixture was heated to reflux for 4 hours, cooled to room temperature, water was added, and the mixture was extracted with chloroform. The chloroform layer was concentrated under reduced pressure and purified by silica gel column chromatography (developing solvent: chloroform / methanol = 15/1 to 10/1), and the resulting solid was washed with hexane to give compound 9 (1.32 g, yield). 50%).

  A mixture of Compound 9 (8.9 g, 14.6 mmol), Compound 10 (4.2 g, 14.6 mmol: manufactured by Tokyo Chemical Industry Co., Ltd.) and methanol (50 ml) was stirred at 50 ° C. for 1.5 hours, and then concentrated under reduced pressure. The obtained solid was washed with methanol / water = 1/2 to obtain Dye (3) (11.5 g, yield 92.3%).

(Synthesis Example 4: Synthesis of Dye (4))

  N-ethyl-p-toluidine (Tokyo Chemical Industry Co., Ltd., 138 g) was dissolved in N, N-dimethylformamide (520 ml), cooled in an ice bath, and t-butoxypotassium (115 g) was added little by little. Further, a DMF (180 ml) solution of 4,4′-difluorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd., 37 g) was added dropwise over 30 minutes with cooling in an ice bath, and then stirred at 50 ° C. for 3 hours. Water and toluene were added, the organic layer was separated, and the organic layer was washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography (hexane / ethyl acetate 15/1 to 10/1) gave Compound D (63.6 g) as a pale yellow solid.

  Phosphorus oxychloride (7.3 ml) (manufactured by Wako Pure Chemical Industries, Ltd.) is added to a mixture of compound D (24 g), compound 3 (11.1 g) (manufactured by Tokyo Chemical Industry Co., Ltd.) and toluene (130 ml) for 5 hours. Heated to reflux. After cooling to room temperature, water was added, extracted with chloroform, and the organic layer was washed 3 times with saturated brine. The mixture was concentrated under reduced pressure and purified by silica gel column chromatography (chloroform / methanol = 12/1) to obtain Compound E (34.8 g).

  A mixture of Compound E (6.66 g), lithium bis (trifluoromethanesulfonyl) imide (manufactured by Tokyo Chemical Industry Co., Ltd., 2.87 g) and methanol (100 ml) was stirred at 40 ° C. for 30 minutes and then concentrated under reduced pressure to obtain The solid was washed with a mixture of methanol / water (1/2) to give Dye (4) (6.51 g).

(Synthesis Example 5: Synthesis of Dye (5))
(Synthesis of Intermediate C1)

  To a mixture of Intermediate D (24 g), 1-methyl-2-phenylindole (Tokyo Chemical Industry Co., Ltd., 11.1 g) and toluene (130 ml), phosphorus oxychloride (Wako Pure Chemical Industries, Ltd., 7.3 ml) And heated to reflux for 5 hours. After cooling to room temperature, water was added, extracted with chloroform, and the organic layer was washed 3 times with saturated brine. The extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (chloroform / methanol = 12/1) to obtain Intermediate C1 (34.8 g).

A mixture of intermediate C1 (6.0 g) and 95% sulfuric acid (90 g) was stirred at 70 ° C. for 6 hours and at 80 ° C. for 4 hours, then poured into ice water, and the precipitate was collected by filtration. After dissolving in acetone and diluting with water, the pH was adjusted to 8 with a 1N aqueous sodium hydroxide solution, and the precipitate was filtered and dried to obtain Dye 1 (5.4 g). Dye (5) was a 64:36 mixture of Dye (5) A and Dye (5) B by ¹ H NMR analysis.

The results of ¹ H NMR and MS are shown below.
¹ H NMR (500 MHz, CD ₃ OD) δ 1.25 (t, H-4), 2.39 (s, H-1), 3.88 (m, H-5, H-11), 6.4 -6.8 (br, H-6), 7.00 (d, H-15), 7.12 (d, H-3), 7.23-7.38 (m, H-2, H- 7, H-8, H-9, H-10), 7.60 (d, H-12), 7.63 (dd, H-16), 7.71 (d, H-14), 7. 87 (dd, H-13), 8.11 (d, H-17)
_{MS (LDI, posi) m /} z 718 (M + H, C 46 H 44 N 3 O 3 S), 740 (M + Na, C 46 H 43 N 3 NaO 3 S).

(Synthesis Example 6: Synthesis of Dye (6))
C. I. Chloroform (222.9 g) and N, N-dimethylformamide (13.225 g) were added to Acid Red 289 (Tokyo Chemical Industry Co., Ltd., 22.29 g), and thionyl chloride (16 19 g) was added dropwise. After the dropwise addition, the temperature was raised, the reaction was carried out at 50 ° C. for 5 hours, and then cooled to 20 ° C. or less, and mixed with triethylamine (32.8 g, 0.324 mol) and 2-ethylhexylamine (18.57 g, 0.1436 mol). The liquid was added dropwise over 35 minutes while maintaining the temperature at 20 ° C or lower. Then, it stirred at room temperature for 5 hours. The solvent was concentrated, methanol (15 ml) was added and the mixture was sufficiently stirred, and then added dropwise to water (557 g) with stirring to precipitate red crystals. The part that became Harz was again dissolved in methanol, concentrated, and added again to water for crystallization. The crystal once filtered was washed with water (300 ml) and dried under reduced pressure to obtain Dye (6) (21.823 g).

[Synthesis of resin]
(Reference Synthesis Example 1: Synthesis of Resin A)
Propylene glycol monomethyl ether acetate (145 parts by weight) was stirred while being purged with nitrogen, and the temperature was raised to 120 ° C. Styrene (20 parts by weight), glycidyl methacrylate (57 parts by weight) 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. It was. Next, the inside of the reaction vessel was changed to air substitution, and trisdimethylaminomethylphenol (0.7 parts by weight) and hydroquinone (0.12 parts by weight) were added to 27 parts by weight of acrylic acid, and the reaction was continued at 120 ° C. for 6 hours. It was. Then, 52 parts by weight of tetrahydrophthalic anhydride (THPA) and triethylamine (0.7 parts by weight) 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).

[Preparation of blue pigment dispersion]
C.I. I. Pigment Blue 15: 6 is 11.36 parts by weight, 57.5 parts by weight of propylene glycol monomethyl ether acetate as a solvent, and a dispersant “Disperbic 2000” (manufactured by Big Chemie) is 3.02 parts by weight in terms of solid content, diameter 0 A stainless steel container was filled with 215.7 parts by weight of 5 mm zirconia beads and dispersed in a paint shaker for 6 hours to prepare a blue pigment dispersion.

[Preparation of colored resin composition]
Each dye obtained by [Synthesis of Dye] and Resin A obtained by [Synthesis of Resin] are mixed with other components so as to have the composition described in Tables 1 to 3, and a colored resin composition Was prepared. The numerical values in Tables 1 to 3 all represent parts by weight in the resist solid content. The solid content in the resist was 22%, and the solvent composition was PGMEA (propylene glycol monomethyl ether acetate): PGME (propylene glycol monomethyl ether) = 7: 3.
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, the numerical value in Tables 1-3 represents the weight part of each component to add.

<Production of colored resin film and evaluation of solvent resistance>
Each colored resin composition is applied onto a glass substrate cut into 5 cm square by spin coating so as to have a dry film thickness of 1.8 μm, dried under reduced pressure, and then prebaked at 80 ° C. for 3 minutes on a hot plate. did. Thereafter, the entire surface was exposed with an exposure amount of 60 mJ / cm ² and baked at 230 ° C. for 30 minutes in a clean oven. Thereafter, the spectral transmittance was measured with a spectrophotometer U-3310 (manufactured by Hitachi, Ltd.), and the chromaticity (C light source) in the XYZ color system was calculated.
Subsequently, after the substrate was immersed in PGMEA for 30 minutes, the spectral transmittance was measured as described above, and the chromaticity (C light source) in the XYZ color system was calculated. Tables 4 to 6 summarize the results of measuring the color difference (ΔE * ab) from the chromaticity after immersion, that is, the solvent resistance.
Further, the substrate was measured with a spectrophotometer U-3310 (manufactured by Hitachi, Ltd.), and the results are shown in Tables 7 and 8.

As shown in Tables 4-6, it can be seen that the pixels formed using the colored resin composition of the present invention are remarkably excellent in solvent resistance.
In addition, as shown in Tables 7 and 8, pixels formed using the colored resin composition of the present invention have high luminance.
Thus, the liquid crystal display device having pixels formed using the colored resin composition of the present invention has high image quality.

<About colored resin composition for green pixel formation>
[1] Synthesis of yellow dye <Synthesis Example 1: Synthesis of compound (1-i)>
To a four-necked flask, 117 parts by weight of 4-acetamidobenzenesulfonyl chloride, 1600 parts by weight of methylene chloride, 56 parts by weight of triethylamine, and 3 parts by weight of 4-dimethylaminopyridine were added and cooled to 5 ° C. Subsequently, 71 parts by weight of 1,5-dimethylhexylamine was added dropwise over 15 minutes, followed by stirring at room temperature for 6 hours. The organic layer was washed twice with 1000 parts by weight of 1 mol / L hydrochloric acid, followed by washing with 1000 parts by weight of a saturated aqueous sodium hydrogen carbonate solution, and the resulting organic layer was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the solvent was distilled off to obtain 154 parts by weight of a white solid intermediate (ia).

When 98 parts by weight of intermediate (ia) and 250 parts by weight of 5% by weight hydrochloric acid were added to a four-necked flask and stirred at 90 ° C. for 5 hours, white solid (1-b) was obtained. This white solid was used in the next reaction without purification.

  To the suspension containing the above (ib), 1000 parts by weight of water and 24 parts by weight of concentrated hydrochloric acid were added, cooled to 5 ° C., 8 parts by weight of sodium nitrite was added, and stirred for 30 minutes. 26 parts by weight of 1- (2-ethylhexyl) -1,2-dihydro-6-hydroxy-4-methyl-2-oxo-3-pyridinecarbonitrile was added to a mixed solution of 80 parts by weight of methanol and 50 parts by weight of water, The solution containing the diazonium salt was added dropwise while maintaining the pH at 8 with sodium hydroxide. The reaction solution was subjected to suction filtration to obtain an orange solid. This solid was purified by silica gel chromatography to obtain 66 parts by weight of yellow solid compound (1-i).

The maximum absorption wavelength (λmax) of this compound in a 10 ppm chloroform solution was 431 nm, and the Gram extinction coefficient was 87. The results of NMR are shown below.
¹ H NMR (CDCl ₃ , 400 MHz) δ 7.96 (d, 2H, J = 8.8 Hz), 7.57 (d, 2H, J = 8.8 Hz), 4.26 (d, 2H, J = 8.4 Hz), 4.00-3.83 (m, 2H), 3.45-3.30 (m, 1H) 2.64 (s, 3H), 1.87-1.75 (m, 1H) ), 1.48-1.00 (m, 18H), 0.97-0.86 (m, 6H), 0.81 (dd, 6H, J = 6.4, 2.4 Hz).

[2] Resin synthesis
<Reference Synthesis Example 2: Synthesis of Resin B>
Prepare a separable flask with a cooling tube as a reaction tank, charge 400 parts by weight of propylene glycol monomethyl ether acetate, purge with nitrogen, and heat in an oil bath while stirring to raise the temperature of the reaction tank to 90 ° C. did.

  Meanwhile, 30 parts by weight of dimethyl-2,2 '-[oxybis (methylene)] bis-2-propenoate, 60 parts by weight of methacrylic acid, 110 parts by weight of cyclohexyl methacrylate, t-butylperoxy-2-ethyl Charge 5.2 parts by weight of hexanoate and 40 parts by weight of propylene glycol monomethyl ether acetate, charge 5.2 parts by weight of n-dodecyl mercaptan and 27 parts by weight of propylene glycol monomethyl ether acetate to the chain transfer agent tank, and temperature of the reaction tank Was stabilized at 90 ° C., dripping was started from the monomer tank and the chain transfer agent tank, and polymerization was started. While maintaining the temperature at 90 ° C., dropping was carried out over 135 minutes each, and 60 minutes after the dropping was finished, the temperature was raised and the reaction vessel was brought to 110 ° C.

  After maintaining at 110 ° C. for 3 hours, a gas introduction tube was attached to the separable flask and bubbling of oxygen / nitrogen = 5/95 (v / v) mixed gas was started. Next, 39.6 parts by weight of glycidyl methacrylate, 0.4 parts by weight of 2,2′-methylenebis (4-methyl-6-tert-butylphenol), and 0.8 parts by weight of triethylamine were charged into the reaction vessel at 110 ° C. as it was. For 9 hours. The polystyrene equivalent weight average molecular weight Mw measured by GPC of the resin B thus obtained was 8000, and the acid value was 101 mg-KOH / g.

<Reference Synthesis Example 3: Synthesis of Resin C>
145 parts by weight of propylene glycol monomethyl ether acetate was stirred while purging with nitrogen, and the temperature was raised to 120 ° C. 10 parts by weight of styrene, 85.2 parts by weight of glycidyl methacrylate and 66 parts by weight of monoacrylate FA-513M (manufactured by Hitachi Chemical Co., Ltd.) having a tricyclodecane skeleton were added dropwise thereto, and 2.2'-azobis-2-methyl 8.47 parts by weight of butyronitrile was added dropwise over 3 hours, and stirring was continued at 90 ° C. for 2 hours. Next, the inside of the reaction vessel was changed to air substitution, 0.7 part by weight of trisdimethylaminomethylphenol and 0.12 part by weight of hydroquinone were added to 43.2 parts by weight of acrylic acid, and the reaction was continued at 100 ° C. for 12 hours. Thereafter, 56.2 parts by weight of tetrahydrophthalic anhydride (THPA) and 0.7 parts by weight of triethylamine were added and reacted at 100 ° C. for 3.5 hours. The polystyrene equivalent weight average molecular weight Mw measured by GPC of the resin C thus obtained was about 8400, and the acid value was 80 mg-KOH / g.
Further, propylene glycol monomethyl ether acetate was added to adjust the solid content concentration to 40%.

[3] Synthesis of photopolymerization initiator A photopolymerization initiator (compound I-1) is shown.

  Compound I-1 was synthesized according to the method described in Japanese Patent Application Laid-Open No. 2008-179611.

[4] Preparation of green pigment dispersion
As a halogenated metal phthalocyanine pigment, C.I. I. Pigment Green 58 (manufactured by DIC), 12.7 parts by weight, “BYK-LPN6919” (methacrylic acid AB block copolymer, amine value 121 mg-KOH / g, acid value 1 mg-KOH / g or less) is 3.2 parts by weight in terms of solid content, and 4.2 parts by weight of resin B synthesized in Reference Synthesis Example 2 is mixed, and using propylene glycol monomethyl ether acetate as a solvent, the solid content concentration Adjusted to 20%. A stainless steel container was filled with 100.5 parts by weight of the mixed solution and 300 parts by weight of zirconia beads having a diameter of 0.5 mm, and dispersed in a paint shaker for 6 hours to prepare a green pigment dispersion.

[5] Preparation of colored resin composition
Dye synthesized in [1], resin C synthesized in [2], photopolymerization initiator synthesized in [3], pigment dispersion prepared in [4], dipentaerythritol hexaacrylate as a polymerizable monomer, chain transfer Diluted with 1% propylene glycol monomethyl ether acetate pentaerythritol-tetrakis (3-mercaptopropionate) (manufactured by Sakai Chemical Co., Ltd.) and fluorinated surfactant F-475 (DIC) as a surfactant Were mixed in the proportions shown in Table 9, and propylene glycol monomethyl ether acetate as a solvent was used to prepare colored resin compositions of Examples and Comparative Examples so as to have a solid content concentration of 20%. In addition, the numerical value of Table 9 is content (weight part) which does not contain a solvent.
The components having the following composition were mixed and dissolved to prepare a colored photopolymerizable composition. In addition, the numerical value of Table 9 is content (weight part) which does not contain a solvent.

In addition, all the numerical values in Table 9 represent parts by weight of each component to be added.
In addition, each compound in Table 9 is as follows.
PET-P: pentaerythritol-tetrakis (3-mercaptopropionate) (manufactured by Sakai Chemical Co., Ltd.)
DPHA: Dipentaerythritol hexaacrylate F475: Fluorosurfactant (manufactured by DIC)

[5] Measurement of dissolution time and remaining film ratio On the glass substrate AN100 (manufactured by Asahi Glass Co., Ltd.) cut into 5 cm square after being washed, the above colored resin compositions are dried to a thickness of 2.0 μm by spin coating. And dried under reduced pressure. When spray development is performed using a 0.04 wt% aqueous potassium hydroxide solution at a developer temperature of 23 ° C. and a pressure of 0.25 MPa, the unexposed portion of the colored resin composition is completely dissolved in the developer and the substrate is exposed. The time taken was the dissolution time of the colored resin composition.
Similar to the measurement of the dissolution time, the colored resin composition was applied and dried on a cleaned glass substrate AN100 (Asahi Glass Co., Ltd.). Thereafter, the entire surface was exposed with an exposure amount of 50 mJ / cm ² and spray-developed using a 0.04 wt% aqueous potassium hydroxide solution at a developer temperature of 23 ° C. and a pressure of 0.25 MPa. The development time was set to dissolution time + 20 seconds. After development, the film was washed with sufficient pure water and dried with clean air, and the thickness of the colored resin composition remaining on the substrate was measured. The ratio of the film thickness after development when the film thickness before development was 100% was defined as the remaining film ratio.
The results are summarized in Table 10.

[6] Width measurement of photocured part (Examples 24-27, Comparative Examples 8-9) (line width measurement)
Similar to the measurement of [5] dissolution time, each colored resin composition was applied and dried on a washed glass substrate AN100 (Asahi Glass Co., Ltd.). Then, it exposed with the exposure amount of 50 mJ / cm < ² > using the photomask which has a width | variety pattern of 40 micrometers in width and 30 mm in length, Developer temperature 23 degreeC, pressure using 0.04 weight% potassium hydroxide aqueous solution. Spray development was performed at 0.25 MPa.
The development time was two conditions: dissolution time + 10 seconds and dissolution time + 20 seconds.
After development, the substrate was washed with sufficient pure water, dried with clean air, and baked in a 230 ° C. oven for 20 minutes. Thereafter, the line width of the photocured portion was measured with a 50 × optical microscope.
The results are summarized in Table 10.

As shown in Table 10, in the case of a colored resin composition containing a yellow dye, even when no chain transfer agent is contained, even image formation is difficult (Comparative Examples 8 and 9).
On the other hand, the pixel formed using the colored resin composition of the present invention has a high surface curability, so that the film surface due to alkali development in the exposed portion does not dissolve, and shows a high residual film ratio and a photomask having a pattern In the alkali development after exposure using, good pixels could be formed (Examples 24-27).
Accordingly, a color filter including pixels formed using the colored resin composition of the present invention is excellent in pixel formation, and a liquid crystal display device and an organic EL display device including the color filter are of high quality.

  Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention. This application is based on a Japanese patent application filed on March 23, 2011 (Japanese Patent Application No. 2011-064454) and a Japanese patent application filed on November 28, 2011 (Japanese Patent Application No. 2011-259238). Incorporated by reference.

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 (7)

A colored resin composition comprising (A) a dye, (B) a solvent, (C) a binder resin and (D) a chain transfer agent,
The (A) dye is a compound represented by any one of the following formulas (II) to (V),
The (D) chain transfer agent is a compound represented by the following formula (I):
And (E) a polymerizable monomer,
Further, (F) contains at least one of a photopolymerization initiation component and a thermal polymerization initiation component,
In addition to (A) dye as a coloring material, it contains a pigment,
A colored resin composition in which the total content of coloring materials contained in the colored resin composition is 5% by weight or more based on the total solid content.
(In the above formula (I), p represents an integer of 2 to 4.
R ^a1 represents a hydrogen atom or an alkyl group which may have a substituent.
X represents a direct bond , a divalent to tetravalent heterocyclic group , a divalent to tetravalent aromatic ring group, or a secondary to quaternary carbon atom having any of the following structures .
In addition, a plurality of structures represented by the following formula (I ′) contained in one molecule
May be the same or different. )
(In the formula (II), Z ^m1- represents an m1-valent anion.
m1 represents an integer of 1 to 4.
R ^{1 to} R ⁶ each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or an aromatic ring group optionally having a substituent. Adjacent R ^{1 to} R ⁶ may be bonded to form a ring. The ring may have a substituent.
R ⁷ and R ⁸ represent a hydrogen atom or an arbitrary substituent. R ⁷ and R ⁸ may be connected to each other to form a ring.
Moreover, the benzene ring in the above formula (II) may further have an arbitrary substituent.
In addition, multiple molecules in one molecule
May be the same structure or different structures. )
(In the above formula (III), ^Zm2- represents an m2-valent anion.
m2 represents an integer of 1 to 4.
R ^{11 to} R ¹⁶ each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or an optionally substituted aromatic ring group. R ¹¹ and R ¹² , R ¹³ and R ^14, and R ¹⁵ and R ¹⁶ may be bonded to each other to form a ring structure.
R ¹⁷ and R ¹⁸ each independently represents a hydrogen atom or an arbitrary substituent. R ¹⁷ and R ¹⁸ may be bonded to each other to form a ring.
Further, the benzene ring and indole ring in the above formula (III) may further have an arbitrary substituent.
In addition, multiple molecules in one molecule
May be the same structure or different structures. )
(In the above formula (IV)
R ^{41 to} R ⁴⁶ each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent.
Adjacent R ^{41 to} R ⁴⁶ may be connected to each other to form a ring, and the ring may have a substituent.
R ⁴⁷ and R ⁴⁸ each independently represents a hydrogen atom or an arbitrary substituent.
R ⁴⁷ and R ⁴⁸ may be bonded to each other to form a ring, and the ring may have a substituent.
Moreover, the benzene ring and indole ring in the above formula (IV) may further have an arbitrary substituent.
M ⁺ represents a hydrogen ion, an alkali metal cation, an alkaline earth metal cation, a tertiary ammonium cation or a quaternary ammonium cation.
n represents an integer of 0 to 4. )
(In the formula (V), R ^{b1 to} R ^b4 each independently represents a hydrogen atom, —R ^b6, or an aromatic hydrocarbon group having 6 to 10 carbon atoms.
R ^{b5 _{is, -SO 3 -, -SO 3 H}} , -SO 3 M, -CO 2 H, -CO 2 R b6, -SO 3 R b6, the -SO 2 ^{NHR b8} or _-SO 2 ^NR b8 ^{R b9} Represent.
m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R ^b5 may be the same or different.
R ^b6 represents a saturated hydrocarbon group having 1 to 10 carbon atoms.
R ^b8 and R ^b9 each independently represent a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or -Q1.
Q1 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms.
M represents a sodium atom or a potassium atom.
D represents a halogen atom. a represents an integer of 0 or 1. ) A colored resin composition comprising (A) a dye, (B) a solvent, (C) a binder resin and (D) a chain transfer agent,
The (A) dye is a compound represented by any one of the following formulas (II) to (V),
The (D) chain transfer agent is at least one selected from ethylene glycol bis (3-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate) and pentaerythritol tetrakis (3-mercaptopropionate). Seeds,
And (E) a polymerizable monomer,
Further, (F) contains at least one of a photopolymerization initiation component and a thermal polymerization initiation component,
In addition to (A) dye as a coloring material, it contains a pigment,
A colored resin composition in which the total content of coloring materials contained in the colored resin composition is 5% by weight or more based on the total solid content.
(In the formula (II), Z ^m1- represents an m1-valent anion.
m1 represents an integer of 1 to 4.
R ^{1 to} R ⁶ each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or an aromatic ring group optionally having a substituent. Adjacent R ^{1 to} R ⁶ may be bonded to form a ring. The ring may have a substituent.
R ⁷ and R ⁸ represent a hydrogen atom or an arbitrary substituent. R ⁷ and R ⁸ may be connected to each other to form a ring.
Moreover, the benzene ring in the above formula (II) may further have an arbitrary substituent.
In addition, multiple molecules in one molecule
May be the same structure or different structures. )
(In the above formula (III), ^Zm2- represents an m2-valent anion.
m2 represents an integer of 1 to 4.
R ^{11 to} R ¹⁶ each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or an optionally substituted aromatic ring group. R ¹¹ and R ¹² , R ¹³ and R ^14, and R ¹⁵ and R ¹⁶ may be bonded to each other to form a ring structure.
R ¹⁷ and R ¹⁸ each independently represents a hydrogen atom or an arbitrary substituent. R ¹⁷ and R ¹⁸ may be bonded to each other to form a ring.
Further, the benzene ring and indole ring in the above formula (III) may further have an arbitrary substituent.
In addition, multiple molecules in one molecule
May be the same structure or different structures. )
(In the above formula (IV)
R ^{41 to} R ⁴⁶ each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent.
Adjacent R ^{41 to} R ⁴⁶ may be connected to each other to form a ring, and the ring may have a substituent.
R ⁴⁷ and R ⁴⁸ each independently represents a hydrogen atom or an arbitrary substituent.
R ⁴⁷ and R ⁴⁸ may be bonded to each other to form a ring, and the ring may have a substituent.
Moreover, the benzene ring and indole ring in the above formula (IV) may further have an arbitrary substituent.
M ⁺ represents a hydrogen ion, an alkali metal cation, an alkaline earth metal cation, a tertiary ammonium cation or a quaternary ammonium cation.
n represents an integer of 0 to 4. )
(In the formula (V), R ^{b1 to} R ^b4 each independently represents a hydrogen atom, —R ^b6, or an aromatic hydrocarbon group having 6 to 10 carbon atoms.
R ^b5 represents —SO ₃ ^— , —SO ₃ H, —SO ₃ M, —CO ₂ H, —CO ₂ R ^b6 , —SO ₃ R ^b6 , —SO ₂ NHR ^b8 or —SO ₂ NR ^b8 R ^b9 . Represent.
m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R ^b5 may be the same or different.
R ^b6 represents a saturated hydrocarbon group having 1 to 10 carbon atoms.
R ^b8 and R ^b9 each independently represent a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or -Q1.
Q1 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms.
M represents a sodium atom or a potassium atom.
D represents a halogen atom. a represents an integer of 0 or 1. )   The colored resin composition according to claim 1 or 2, wherein the content of the (D) chain transfer agent is 2% by weight or more and 10% by weight or less based on the total solid content. The colored resin composition according to any one of claims 1 to 3, wherein the polymerizable monomer (E) is a compound having an ethylenically unsaturated double bond. The color filter containing the pixel formed using the colored resin composition as described in any one of Claims 1-4 . A liquid crystal display device comprising the color filter according to claim 5 . An organic EL display device comprising the color filter according to claim 5 .