JP6520118B2 - Color material dispersion, colored resin composition for color filter, color filter, liquid crystal display device, and light emitting display device - Google Patents

Description

  The present invention relates to a colorant dispersion, a colored resin composition for a color filter, a color filter, a liquid crystal display, and a light emitting display.

Many thin image display devices represented by displays and the like, so-called flat panel displays, have been launched on the market, characterized by being thinner than a CRT display and taking up less space in the depth direction. The market price has become reasonable year by year with the evolution of production technology, the demand is further expanded, and the production volume is also increasing year by year. In particular, color LCD TVs almost reached the TV mainstream. In recent years, a light emitting display such as an organic EL display having high visibility due to self light emission is also attracting attention as a next-generation image display. In the performance of these image display devices, further improvement in image quality such as improvement in contrast and color reproducibility and reduction in power consumption are strongly desired.
Color filters are used in these liquid crystal display devices and light emitting display devices. For example, in the case of a color liquid crystal display, a backlight is used as a light source, and the amount of light is controlled by electrically driving the liquid crystal, and color representation is performed by passing the light through a color filter. Therefore, the color expression of the liquid crystal television must be a color filter, and plays a large role in determining the performance of the display. In the light emitting display device, when a color filter is used as the light emitting element emitting white light, a color image is formed as in the liquid crystal display device.

As a trend in recent years, power saving of the image display apparatus is required, and in order to improve the utilization efficiency of the backlight, particularly, high luminance of the color filter is required. This is particularly a big issue for mobile displays (mobile phones, smart phones, tablet PCs).
Although battery capacity has increased due to technological advances, mobile storage capacity remains the same, while power consumption tends to increase as screen size increases. The image display apparatus including the color filter influences the design and performance of the mobile terminal in order to directly connect to the usable time and charging frequency of the mobile terminal.

Here, the color filter is generally formed on a transparent substrate, a colored layer formed on the transparent substrate and made of colored patterns of three primary colors of red, green and blue, and a transparent substrate so as to separate each colored pattern. And a light shielding portion formed.
In the formation method of such a colored layer, the pigment dispersion method using the pigment excellent in heat resistance or light resistance as a coloring material has been widely used. However, with color filters using pigments, it has become difficult to achieve the current demand for higher brightness.

  As one means for achieving high brightness, a colored resin composition for a color filter using a dye has been studied. Dyes can generally produce color filters with high transmittance and high brightness compared to pigments, but the heat resistance and light resistance are poor, and the chromaticity is likely to change during high temperature heating in the color filter manufacturing process, etc. There was a problem. Moreover, the colored resin composition using the dye has a problem that foreign matters are easily precipitated during the drying process. When foreign matter is deposited on the coating film, the contrast is significantly deteriorated and it is difficult to use as a colored layer.

As a method of improving various resistance of a dye, a method of forming a salt of a dye is known.
For example, Patent Document 1 discloses an example in which a chloride ion or an aryl sulfate ion is used as a counter anion of a triarylmethane dye in order to improve the heat resistance of the triarylmethane dye.

  In Patent Document 2, an organic sulfonated product having a triarylmethane basic dye and at least two sulfone groups as a means for obtaining a stable coloring composition for color filter having excellent color characteristics, heat resistance, light resistance and solvent resistance. And a salt forming compound comprising

Further, in Patent Document 3, as a means for obtaining a colored resin composition excellent in light resistance and also satisfying light resistance, a sulfonated dye skeleton such as phthalocyanine or anthraquinone is used as a counter anion, and a triarylmethane skeleton as a cation and a salt Methods to form have been reported.
However, the dye-forming compounds and the salt-forming compounds of the counter anions described in Patent Documents 1 to 3 have problems of color resistance, heat resistance and dyeability to fibers being insufficient.

  In Patent Document 4, as a blue pigment for a color filter which enables liquid crystal display excellent in luminance over a long time even at high temperature, one selected from tungsten, silicon and phosphorus of a specific basic triarylmethane dye There is disclosed a blue pigment for color filter comprising an anion containing a plurality of elements and oxygen as essential elements.

JP 2008-304766 A JP, 2011-7847, A WO2009 / 107734 Japanese Patent Application Publication No. 2011-186043

  However, the color materials described in Patent Documents 1 to 4 are all insufficient in heat resistance, and a color material having further excellent heat resistance is required.

  The present invention has been made in view of the above situation, and is a coloring material dispersion which is excellent in heat resistance and capable of forming a coating film with high brightness and high contrast, and a coloring layer excellent in heat resistance and high contrast and high contrast It is an object of the present invention to provide a colored resin composition for a color filter capable of forming a color filter, a color filter excellent in heat resistance, high brightness and high contrast, a liquid crystal display and a light emitting display having the color filter.

  The colorant dispersion according to the present invention contains (A) a colorant, (B) a dispersant, and (C) a solvent, and the (A) colorant is represented by the following general formula (I): Color material (1).

(In general formula (I), Ar represents a divalent aromatic group which may have a substituent, R ^{1 to} R ⁶ each independently represent a hydrogen atom, an aromatic hydrocarbon group as a substituent, a halogen An aliphatic hydrocarbon group which may have at least one of an atom and a hydroxyl group, or an aromatic hydrocarbon which may have at least one of a halogen atom and an aliphatic hydrocarbon group as a substituent R ¹ and R ² , R ³ and R ⁴ , and R ⁵ and R ⁶ may combine to form a ring structure, provided that at least one of R ^{1 to} R ⁶ is carbon It contains an alicyclic hydrocarbon group having 6 or more atoms.
a represents a number of 1 or more, and X ^a- represents an a-valent anion.
When there are a plurality of R ^{1 to} R ⁶ and Ar, the plurality of R ^{1 to} R ⁶ and Ar may be the same or different. )

  The colored resin composition for a color filter according to the present invention contains (A) a colorant, (B) a dispersant, (C) a solvent, and (D) a binder component, and the (A) colorant is And a coloring material (1) represented by the general formula (I).

  The color filter according to the present invention is a color filter comprising at least a transparent substrate and a colored layer provided on the transparent substrate, wherein at least one of the colored layers is represented by the general formula (I). A color material (1) is included.

  In the colorant dispersion of the present invention, the colored resin composition for a color filter of the present invention, and the color filter of the present invention, the number of carbon atoms in the colorant (1) represented by the general formula (I) is It is preferable that the melting point of the alicyclic hydrocarbon corresponding to 6 or more alicyclic hydrocarbon groups is 80 to 300 ° C. in order to improve the heat resistance of the colored layer and to achieve high brightness and high contrast. .

In the colorant dispersion of the present invention, the colored resin composition for a color filter of the present invention, and the color filter of the present invention, colorants in which a in the above general formula (I) is 1 can be selected and used. .
Further, in the colorant dispersion of the present invention, the colored resin composition for a color filter of the present invention, and the color filter of the present invention, a colorant in which a in the above general formula (I) is 2 or more is selected and used. be able to.

Colorant dispersion of the present invention, a color filter for the colored resin composition of the present invention, and in the color filter of the present invention, the X ^a- is in the general formula (I), 1 or more selected from tungsten and molybdenum It is preferable from the viewpoint of improving the heat resistance of the colored layer and achieving high brightness and high contrast by using an a-valent polyacid containing the following atoms.

  In the colorant dispersion of the present invention, the colored resin composition for a color filter of the present invention, and the color filter of the present invention, the polyacid contained in the colorant (1) represented by the general formula (I) is It is preferable that the heat resistance of the colored layer be improved and that the coloring layer contain at least tungsten and the molar ratio of molybdenum to tungsten be 2/98 or less from the viewpoints of high brightness and high contrast.

The present invention provides a liquid crystal display device comprising the color filter according to the present invention, a liquid crystal layer, and a light resistant substrate.
The present invention also provides a light emitting display device comprising the color filter according to the present invention and a light emitter.

  According to the present invention, a colorant dispersion having excellent heat resistance and capable of forming a coating film with high brightness and high contrast, and a coloring resin for color filter capable of forming a coloring layer excellent in heat resistance and having high brightness and high contrast It is possible to provide a composition, a color filter excellent in heat resistance, high brightness and high contrast, a liquid crystal display device and a light emitting display device having the color filter.

FIG. 1 is a schematic cross-sectional view showing an example of the color filter of the present invention. FIG. 2 is a schematic cross-sectional view showing an example of the liquid crystal display device of the present invention. FIG. 3 is a schematic cross-sectional view showing an example of the light emitting display device of the present invention.

Hereinafter, the colorant dispersion liquid, the color filter, the liquid crystal display device, and the light emitting display device according to the present invention will be described in order.
In the present invention, light includes electromagnetic waves of wavelengths in the visible and non-visible regions, and radiation, and radiation includes, for example, microwaves and electron beams. Specifically, it refers to an electromagnetic wave having a wavelength of 5 μm or less and an electron beam.
In the present invention, (meth) acrylic represents each of acrylic and methacrylic, and (meth) acrylate represents each of acrylate and methacrylate.
In the present invention, the organic group means a group having one or more carbon atoms.

1. Colorant Dispersion The colorant dispersion according to the present invention contains (A) a colorant, (B) a dispersant, and (C) a solvent, and the (A) colorant has the following general formula (I It contains the coloring material (1) represented by.

(In general formula (I), Ar represents a divalent aromatic group which may have a substituent, R ^{1 to} R ⁶ each independently represent a hydrogen atom, an aromatic hydrocarbon group as a substituent, a halogen An aliphatic hydrocarbon group which may have at least one of an atom and a hydroxyl group, or an aromatic hydrocarbon which may have at least one of a halogen atom and an aliphatic hydrocarbon group as a substituent R ¹ and R ² , R ³ and R ⁴ , and R ⁵ and R ⁶ may combine to form a ring structure, provided that at least one of R ^{1 to} R ⁶ is carbon It contains an alicyclic hydrocarbon group having 6 or more atoms.
a represents a number of 1 or more, and X ^a- represents an a-valent anion.
When there are a plurality of R ^{1 to} R ⁶ and Ar, the plurality of R ^{1 to} R ⁶ and Ar may be the same or different. )

  The colorant dispersion according to the present invention is excellent in heat resistance by dispersing the colorant (1) represented by the general formula (I) in a solvent (C) with a dispersant (B), It becomes a colorant dispersion that can form a coating film with high brightness and high contrast.

Although it is not clarified as an effect | action which exhibits the above effects by the said specific combination, it estimates as follows.
The colorant (1) used in the colorant dispersion of the present invention contains a cation having a triarylmethane skeleton as represented by the above general formula (I), and R ^{1 to} R in the triarylmethane skeleton ^At least one of 6 is a substituent containing an alicyclic hydrocarbon group having 6 or more carbon atoms. The alicyclic hydrocarbon group having 6 or more carbon atoms has a bulky structure as compared to a chain aliphatic hydrocarbon group or an aromatic hydrocarbon group having a planar structure. That is, in the alicyclic hydrocarbon group, since the molecular orbital of each carbon atom is an SP3 hybrid orbital, carbon atoms and hydrogen atoms bonded to the carbon atoms are three-dimensionally arranged and bulky. . For example, a cyclohexyl group, which is an alicyclic hydrocarbon group having 6 carbon atoms, has a so-called chair-type conformation or a boat-type conformation, carbon atoms are three-dimensionally disposed, and two carbon atoms each have One of the C—H bonds of is of a bulky structure because it is perpendicular to the quasi-sum plane formed by the carbon ring.
Since triarylmethane cations having such a bulky structure are easily inhibited from intermolecular π-π interactions, triarylmethane cations, even in the aggregated state, are more triaryl than in conventional triarylmethane dyes. It is presumed that stacking of methane skeleton is unlikely to occur. Therefore, it is presumed that the compounds represented by the general formula (I) are arranged so that the triarylmethane skeletons are not in close proximity to each other in the aggregate and they are arranged with a certain distance. Therefore, it is presumed that the compound represented by the general formula (I) absorbs light more efficiently than the conventional triarylmethane dyes which are easily stacked. As a result, the aggregates of the coloring material represented by the general formula (I) are also characterized in having a molar extinction coefficient higher than that of the prior art.
The colorant dispersion of the present invention is excellent in heat resistance because the colorant (1) represented by the general formula (I) is dispersed in the form of aggregates by the (B) dispersant, and thus high temperature Even after heating, a reduction in luminance and contrast is suppressed, and a colorant dispersion liquid capable of forming a coating film having high luminance and high contrast can be obtained.

  The coloring material dispersion of the present invention contains (A) a coloring material containing at least the coloring material (1) represented by the general formula (I), (B) a dispersant, and (C) a solvent In addition, other components may be contained as long as the effects of the present invention are not impaired. Hereinafter, each component of the colorant dispersion liquid of the present invention will be described in order.

[(A) Color material]
The coloring material (A) of the present invention contains at least the coloring material (1) represented by the following general formula (I), and further contains other coloring materials as long as the effects of the present invention are not impaired. is there. In the present invention, since the colorant (A) contains the colorant (1), it has excellent heat resistance and can achieve high brightness and high contrast.

(Each symbol in the general formula (I) is as described above.)

<Color material (1)>
In the general formula (I), Ar is a divalent aromatic group which may have a substituent. The said bivalent aromatic group is not specifically limited, It can select suitably in consideration of the color tone etc. of the compound obtained. The aromatic group may be a heterocyclic group in addition to an aromatic hydrocarbon group consisting of carbon rings. As the aromatic hydrocarbon in the aromatic hydrocarbon group, fused polycyclic aromatic hydrocarbons such as naphthalene ring, tetralin ring, indene ring, fluorene ring, anthracene ring, phenanthrene ring and the like other than benzene ring; biphenyl, terphenyl, And chain polycyclic hydrocarbons such as diphenylmethane, triphenylmethane and stilbene. The chained polycyclic hydrocarbon may have O, S, and N in the chain skeleton as in diphenyl ether and the like. On the other hand, as the heterocyclic ring in the heterocyclic group, 5-membered heterocyclic rings such as furan, thiophene, pyrrole, oxazole, thiazole, imidazole and pyrazole; 6-membered heterocyclic rings such as pyrane, pyrone, pyridine, pyrone, pyridazine, pyrimidine and pyrazine And fused polycyclic heterocyclic rings such as benzofuran, thionaphthene, indole, carbazole, coumarin, benzo-pyrone, quinoline, isoquinoline, acridine, phthalazine, quinazoline, quinoxaline and the like.
As a substituent which these aromatic groups may have, halogen atoms, such as a C1-C5 alkyl group, a chlorine atom, a bromine atom, etc. are mentioned.

  In the present invention, Ar is preferably an aromatic group having 6 to 20 carbon atoms, and more preferably an aromatic group consisting of a fused polycyclic carbon ring having 10 to 14 carbon atoms. Among them, a phenylene group or a naphthylene group is more preferable in view of the simple structure and the inexpensive raw materials.

In the general formula (I), R ^{1 to} R ⁶ each independently represent a hydrogen atom, an aliphatic hydrocarbon group which may have at least one of an aromatic hydrocarbon group as a substituent, a halogen atom and a hydroxyl group, Or an aromatic hydrocarbon group which may have at least one of a halogen atom and an aliphatic hydrocarbon group as a substituent, R ¹ and R ² , R ³ and R ⁴ , and R ⁵ and R ⁶ Each may combine to form a ring structure. However, at least one of R ^{1 to} R ⁶ contains an alicyclic hydrocarbon group having 6 or more carbon atoms. In the present invention, including an alicyclic hydrocarbon group having 6 or more carbon atoms means an alicyclic hydrocarbon group having 6 or more carbon atoms, or 6 or more carbon atoms as a substituent. The case containing an alicyclic hydrocarbon group is included. Among them, at least one of R ^{5 and} R ⁶ is preferably an alicyclic hydrocarbon group having 6 or more carbon atoms, from the viewpoint of excellent coloring power and heat resistance.

The aliphatic hydrocarbon group in R ^{1 to} R ⁶ may be a linear or branched aliphatic hydrocarbon group or a cyclic alicyclic hydrocarbon group.
The linear or branched aliphatic hydrocarbon group includes, for example, a linear or branched alkyl group having 1 to 20 carbon atoms, and the like, and among them, a linear or branched alkyl having 1 to 8 carbon atoms It is preferably a group, and is preferably a linear or branched alkyl group having 1 to 5 carbon atoms from the viewpoint of easiness of production and raw material procurement, and among them, it is an ethyl group or a methyl group Is particularly preferred.
The aromatic hydrocarbon group which the aliphatic hydrocarbon group may have as a substituent is not particularly limited, but is preferably an aromatic group having 6 to 20 carbon atoms, for example, and has 6 carbon atoms -16 aromatic groups are more preferred. Among them, phenyl group, naphthyl group and the like are mentioned in view of simple structure and inexpensive raw materials.

The alicyclic hydrocarbon group in R ^{1 to} R ⁶ is not particularly limited, but from the viewpoint of heat resistance, an alicyclic hydrocarbon group having 6 or more carbon atoms is preferable. In the present invention, since at least one of R ^{1 to} R ⁶ contains an alicyclic hydrocarbon group having 6 or more carbon atoms, a compound excellent in heat resistance can be obtained.
Specific examples of the alicyclic hydrocarbon group having 6 or more carbon atoms include cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, norbornyl group, bicyclo [2,2,2] octyl group, adamantyl group and the like And a bridged alicyclic hydrocarbon group. In the present invention, from the viewpoint of heat resistance, among the alicyclic hydrocarbon groups having 6 or more carbon atoms, a bridged alicyclic hydrocarbon group is preferable, and the number of carbon atoms is 7 or more, more preferably It is preferable that it is a bridged alicyclic hydrocarbon group whose carbon reduction number is 10 or more.
In the present invention, a bridged alicyclic hydrocarbon group refers to a polycyclic aliphatic hydrocarbon group having a crosslinked structure in an aliphatic ring and having a polycyclic structure. Since the bridged alicyclic hydrocarbon group has a more bulky structure as compared to an alicyclic hydrocarbon group having no crosslinking structure in the aliphatic ring, the compound aggregate has a bulk It is estimated that the heat resistance becomes smaller.
On the other hand, the upper limit of the carbon atom number of the alicyclic hydrocarbon group is not particularly limited, but is preferably 12 or less, more preferably 10 or less, from the viewpoint of simple structure and easy availability of raw materials.

In the present invention, the melting point of the corresponding alicyclic hydrocarbon in the alicyclic hydrocarbon group having 6 or more carbon atoms is preferably 80 to 300 ° C. By using such an alicyclic hydrocarbon group, when forming a salt of a cation having a triarylmethane skeleton and a polyacid anion, it can be stably present in the bulk, and the heat resistance is improved.
The corresponding alicyclic hydrocarbon is a compound in which hydrogen is added to an alicyclic hydrocarbon group, and for example, an alicyclic hydrocarbon corresponding to a norbornyl group is norbornane (melting point 85 ° C.), The alicyclic hydrocarbon corresponding to the adamantyl group is adamantane (melting point 270 ° C.).

The aromatic hydrocarbon group for R ¹ to R ^6, preferably the number of carbon atoms is 6 to 20 aromatic groups, the number of carbon atoms is more preferably an aromatic group having 6 to 16. The aromatic hydrocarbon group may have at least one of a halogen atom and an aliphatic hydrocarbon group as a substituent, and the aliphatic hydrocarbon group is exemplified as the aliphatic hydrocarbon group. The substituent may contain an alicyclic hydrocarbon group having 6 or more carbon atoms as a substituent.
Examples of the aromatic hydrocarbon group in R ^{1 to} R ⁶ include phenyl group, naphthyl group, tolyl group, xylyl group, cyclohexylphenyl group, norbornylphenyl group, adamantylphenyl group and the like.

R ¹ and R ² , R ³ and R ⁴ , and R ⁵ and R ⁶ combine to form a ring structure, R ¹ and R ² , R ³ and R ⁴ , or R ⁵ and R ⁶ It means that a ring structure is formed through a nitrogen atom. The ring structure is not particularly limited, and examples include pyrrolidine ring, piperidine ring, morpholine ring and the like.

In the present invention, among them, from the viewpoint of chemical stability, any one of R ^{1 to} R ⁶ is an aliphatic hydrocarbon group containing an alicyclic hydrocarbon group having 6 or more carbon atoms, and others Each independently, a hydrogen atom, an alkyl group of 1 to 5 carbon atoms, a phenyl group, or R ¹ and R ² , R ³ and R ⁴ , or R ⁵ and R ⁶ are bonded to form a pyrrolidine ring, piperidine ring, morpholine It is preferable to form a ring.

In the present invention, the anion X a ⁻ represents an a-valent anion. X ^a- is not particularly limited, singly from known anionic, or may be used in combination of two or more.
a represents a number of 1 or more, and in the present invention, the colorant (1) represented by the general formula (I) may be a compound in which a is 1, that is, a compound having a monovalent anion, Further, the color material (1) represented by the general formula (I) may be a compound in which a is 2 or more, that is, a compound having a divalent or higher anion. From the viewpoint that the solubility of the coloring material is lowered and the dispersibility and the dispersion stability are excellent, the compound in which a in the coloring material (1) is 2 or more, that is, a compound having a divalent or higher anion Although preferred, the colorant (1) represented by the general formula (I) having a monovalent anion can be dispersed and used depending on the choice of the solvent and the dispersant.
Hereinafter, the case where X a ⁻ is a monovalent anion and the case where X a ⁻ is a divalent or higher anion will be described in order, but in the present invention, the coloring material represented by formula (I) ( X a ⁻ in 1) may be a mixture of a monovalent anion and a divalent or higher anion.

(If ^{X a-} is a monovalent anion)
In the color material (1) represented by the general formula (I), when X ^a- is a monovalent anion, a monovalent anion is not particularly limited, and an inorganic anion be an organic anion It is also good. Here, the organic anion represents an anion containing at least one carbon atom. Moreover, an inorganic anion represents the anion which does not contain a carbon atom, for example, halide ion like a fluoride ion, a chloride ion, a bromide ion, an iodide ion, nitrate ion (NO < ^- >), perchlorate Ion (ClO ₄ ⁻ ) and the like can be mentioned.

If X ^a- is a monovalent organic anion, the structure is not particularly limited. Among them, an organic group having an anionic substituent is preferable.
As an anionic substituent, for example, -SO ₂ N ^- SO ₂ CH ₃ , -SO ₂ N ^- COCH ₃ , -SO ₂ N ^- SO ₂ CF ₃ , -SO ₂ N ^- COCF ₃ , -CF ₂ SO _{2 ^{N - SO 2 CH 3, -CF}} 2 SO 2 N - COCH 3, -CF 2 SO 2 N - SO 2 CF 3, -CF 2 SO 2 N - COCF 3 or imidate group such as, -SO ₃ ^{-, _{-CF 2 SO 3 -, -COO -}} , -CF 2 COO - substituents, and the like.
Among them, ease and manufacturing cost of raw materials available, from the viewpoint high effect of maintaining the color-developed state is stabilized cations by high acidity, and imidate _{^{groups, -SO 3 -, -CF 2 SO}} 3 - are preferred, further it is preferably (a sulfonato group) ^- -SO _3.

It does not specifically limit as an organic group by which an anionic substituent is substituted. The organic group includes a linear, branched or cyclic saturated or unsaturated hydrocarbon group, a monocyclic or polycyclic aromatic group, and a group obtained by combining them, and these include O, in the carbon chain, Heteroatoms such as S and N may be contained, and a carbonyl group, a carboxy group, an oxycarbonyl group and an amido group may be contained, and a hydrogen atom may be substituted. As a substituent which the organic group may have, a halogen atom etc. are mentioned, for example.
As an organic group by which the said anionic substituent is substituted, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornane, bicyclo [2,2,2] hexane, bicyclo [3,2,3] octane, adamantane etc. are mentioned, for example. Hydrocarbons; benzene, naphthalene, anthracene, phenanthrene, pyrene, triphenylene, trifluorene, fluorene, furan, thiophene, pyrrole, imidazole, pyrane, pyridine, pyrimidine, pyrazine, triazine, indole, purine, quinoline, isoquinoline, xanthene, carbazole, etc. Group compounds, and may further have a substituent such as a halogen atom or an alkyl group.
Among them, a monocyclic or polycyclic aromatic hydrocarbon group and a group obtained by combining these are preferable as the organic group to which the anionic substituent is substituted, from the viewpoint of easy introduction of the anionic substituent.

  When it is intended not to change color due to anions, it is preferable to use an organic group having an absorption maximum in the wavelength region of 400 nm or less. The organic group having an absorption maximum in the wavelength region of 400 nm or less includes, for example, organic groups consisting of fused polycyclic carbon rings such as naphthalene, tetralin, indene, fluorene, anthracene, phenanthrene, etc .; biphenyl, terphenyl, diphenylmethane, triphenyl Organic groups consisting of chained polycyclic hydrocarbons such as methane and stilbene; Organic groups consisting of 5-membered heterocyclic rings such as furan, thiophene, pyrrole, oxazole, thiazole, imidazole and pyrazole, pyran, pyrone, pyridine, pyridazine, Aromatic compounds consisting of a 6-membered heterocyclic ring such as pyrimidine and pyrazine; benzofuran, thionaphthene, indole, carbazole, coumarin, benzo-pyrone, quinoline, isoquinoline, acridine, phthalazine, quinazoline, quinoxaline, etc. Organic group, and the like made.

Moreover, as an organic group to which an anionic substituent is substituted, a skeleton derived from an azo dye, anthraquinone dye, triphenylmethane dye, xanthene dye, phthalocyanine dye, or indigo dye, which is an organic compound or an organic metal compound It is also good. Alternatively, conventionally known acid dyes, direct dyes and acid mordant dyes may be used.
When a dye-derived skeleton, an acid dye, a direct dye, an acid mordant dye or the like is used, the color tone of the obtained color material changes, and the color tone of the color material (1) represented by the general formula (I) It can be adjusted as desired.

(If ^{X a-} is a divalent or more anion)
If X ^a- is a divalent or more anions, the anion is not particularly limited, and may be an inorganic anion be an organic anion.
If X ^a- is a divalent or more organic anions, the structure is not particularly limited. Among them, an organic group having an anionic substituent is preferable.
As an anionic substituent, for example, -SO ₂ N ^- SO ₂ CH ₃ , -SO ₂ N ^- COCH ₃ , -SO ₂ N ^- SO ₂ CF ₃ , -SO ₂ N ^- COCF ₃ , -CF ₂ SO _{2 ^{N - SO 2 CH 3, -CF}} 2 SO 2 N - COCH 3, -CF 2 SO 2 N - SO 2 CF 3, -CF 2 SO 2 N - COCF 3 or imidate group such as, -SO ₃ ^{-, _{-CF 2 SO 3 -, -PO 3}} 2-, -COO -, -CF 2 PO 3 2-, -CF 2 COO - substituents, and the like.
Among them, it is preferable to use two or more monovalent anionic substituents from the viewpoint of stabilizing the cation and stabilizing the color development of the coloring material. The ease and the manufacturing cost of raw materials available, from the viewpoint high effect of maintaining the color-developed state is stabilized cations by high acidity, and imidate _{^{groups, -SO 3 -, -CF 2 SO}} 3 - are preferred, further -SO ₃ ^- and more preferably a (sulfonato group).
When a plurality of anionic substituents are substituted, the same substituent may be used, or different substituents may be used.

It does not specifically limit as an organic group by which an anionic substituent is substituted, It can select suitably from the same organic groups as the case where said ^Xa- is a monovalent anion, and can use it.
Moreover, as an organic group to which an anionic substituent is substituted, a skeleton derived from an azo dye, anthraquinone dye, triphenylmethane dye, xanthene dye, phthalocyanine dye, or indigo dye, which is an organic compound or an organic metal compound It is also good. Alternatively, conventionally known acid dyes, direct dyes and acid mordant dyes may be used.
When a dye-derived skeleton, an acid dye, a direct dye, an acid mordant dye or the like is used, the color tone of the obtained color material changes, and the color tone of the color material (1) represented by the general formula (I) It can be adjusted as desired.

On the other hand, when X a ⁻ is a divalent or higher inorganic anion, the structure or composition thereof is not particularly limited as long as it is an inorganic oxo acid and a dehydrated condensate thereof. Examples of the inorganic anion include anions of divalent or higher oxo acids (phosphate ion, sulfate ion, chromate ion, tungstate ion (WO ₄ ^2- ), molybdate ion (MoO ₄ ^2- ), etc .; Examples thereof include inorganic anions such as polyacid ions in which a plurality of oxo acids are condensed, and mixtures thereof.
The polyacid may be isopolyacid ion (M _m O _n ) ^c- or heteropolyacid ion (X _l M _m O _n ) ^c- . In the above ion formula, M represents a poly atom, X represents a hetero atom, m represents a composition ratio of poly atoms, and n represents a composition ratio of oxygen atoms. As poly atom M, Mo, W, V, Ti, Nb etc. are mentioned, for example. Moreover, as hetero atom X, Si, P, As, S, Fe, Co etc. are mentioned, for example.
Among them, from the viewpoint of heat resistance, it is preferable to be a polyacid anion which contains at least tungsten and may contain molybdenum, and above all, the molar ratio of the molybdenum to the tungsten in the total polyacid anion is 2/98. It is preferable that it is the following.

As a polyacid anion containing at least one of tungsten (W) and molybdenum (Mo), for example, isoporic acid, tungstate ion [W ₁₀ O ₃₂ ] ⁴⁻ , molybdate ion [Mo ₆ O ₁₉ ] ^{2 -} or a heteropoly acid, ion phosphotungstic acid ^{_{[PW 12 O 40] 3-,}} [P 2 W 18 O 62] 6-, silicotungstic acid ion _{[SiW 12 O} ^{40] 4-,} phosphomolybdic acid ion [ PMo ₁₂ O ₄₀ ] ³⁻ , silicomolybdate ion [SiMo ₁₂ O ₄₀ ] ⁴⁻ , lintungst molybdate ion [PW _12−x Mo _x O ₄₀ ] ³⁻ (x is an integer of 1 to 11), [P _{2 W 18-y Mo y O} 62] 6- (y is 1 to 17 integer), Keita ring strike molybdate [SiW ^{_{2-x Mo x O 40]}} 4- (x is 1 to 11 integer), and the like. Among the polyacid anions containing at least one of tungsten (W) and molybdenum (Mo), heteropoly acids are preferable among the above from the viewpoints of heat resistance and availability of raw materials, and P More preferably, it is a heteropoly acid containing phosphorus.

In the present invention, as the anion (X a ⁻ ) of the coloring material (1) represented by the general formula (I), a monovalent anion or a divalent or higher anion can be used alone, and a monovalent anion can be used. And a divalent or higher anion can be used in combination. In the present invention, as the anion, an organic anion or an inorganic anion can be used alone, or an organic anion and an inorganic anion can be used in combination.

(Production Method of Color Material (1) Represented by General Formula (I))
Although the manufacturing method of the compound represented by general formula (I) is not specifically limited, For example, the condensation reaction of the compound represented with the following general formula (A), and the compound represented with the following general formula (B) is carried out The compound represented by the above general formula (I) having a desired anion is obtained by mixing the cation with a desired anion in a solvent, if necessary, after producing a triarylmethane cation. can get.

^(R 1 to R ⁶ in the formula (A) and the general formula (B) is a similar to ^R 1 to R ⁶ in Formula ^(I), at least one of R 1 to R ⁶ Each of which includes an alicyclic hydrocarbon group having 6 or more carbon atoms Ar ′ is a monovalent aromatic group in which hydrogen is bonded to Ar in General Formula (I), and X ′ is a monovalent It is an anion.)

The above-mentioned production method is carried out by dehydration condensation between Ar ^′ of the general formula (A) and the carbonyl group of the general formula (B) to obtain at least one alicyclic hydrocarbon group having 6 or more carbon atoms. It forms a triarylmethane skeleton containing one.
A commercial item may be used for the compound represented by General formula (A), and the compound represented by General formula (B), and you may synthesize | combine the compound which has a desired structure.

Hereinafter, as an example, illustrating the synthesis method of coloring material (1) represented by the general formula (I) in which the number of carbon atoms in R ⁵ or R ⁶ has 6 or more alicyclic hydrocarbon group.
The compound represented by the general formula (A) having an alicyclic hydrocarbon group having 6 or more carbon atoms in R ⁵ or R ⁶ is, for example, a halogenated aromatic compound into which a desired substituent Ar ′ is introduced And an amine compound having an alicyclic hydrocarbon group having 6 or more carbon atoms in a solvent in the presence of a base using palladium acetate or the like as a catalyst.
The amount of the halogenated aromatic compound used is preferably 1.5 to 10 molar equivalents, more preferably 1.5 to 3.0 molar equivalents, more preferably 1. The use of 8 to 2.2 molar equivalents is preferable in terms of suppressing the formation of by-products and improving the reaction yield.
The reaction temperature in the above reaction is not particularly limited, but is usually about 100 to 150 ° C., and preferably 130 to 145 ° C. from the viewpoint of suppressing side reactions. Further, the reaction pressure of the above reaction is not particularly limited, but normal pressure to 0.1 MPa is desirable, and normal pressure is more desirable. The reaction time in the above reaction may vary depending on the amount of synthesis, reaction temperature and the like, and thus can not be generally defined, but is usually set in the range of 6 to 72 hours, preferably 6 to 48 hours.

  Although it does not specifically limit as a base used for the said reaction, For example, a metal alkoxide, metal amide other than sodium hydroxide, potassium hydroxide, potassium carbonate, etc. are mentioned. Among them, it is preferable to use a strong base having low nucleophilicity from the viewpoint of suppressing side reactions and improving the yield of the base generator. For example, potassium-t-butoxide, sodium-t-butoxide, lithium-t- Butoxide, lithium diisopropylamide, potassium hexamethyldisilazide, lithium tetramethylpiperidide and the like are suitably used. It is more preferable to use potassium-t-butoxide among strong bases of low nucleophilicity.

  Although the addition amount of the base is not particularly limited, it is usually 2.0 to 4.0 molar equivalents and 2.5 to 3.5 molar equivalents with respect to the amine compound to improve the reaction yield. It is preferable from the point of view.

The condensation reaction between the compound represented by the general formula (A) and the compound represented by the general formula (B) can be a known method, and for example, a solvent using a chlorinating agent such as phosphorus oxychloride It can be obtained by reacting in the medium.
The amount of the compound represented by the general formula (B) used in the above reaction is preferably 1.5 to 4.0 molar equivalents relative to the general formula (A), and 1.5 to 3 It is more preferable that the amount is 0.1 molar equivalent, and further preferably 1.8 to 2.2 molar equivalents from the viewpoint of suppressing the formation of by-products and improving the reaction yield.
The reaction temperature in the above reaction is not particularly limited, but is usually about 110 to 150 ° C., and preferably 110 to 120 ° C. from the viewpoint of suppressing side reactions. Further, the reaction pressure of the above reaction is not particularly limited, but normal pressure to 0.1 MPa is desirable, and normal pressure is more desirable. The reaction time in the above reaction may vary depending on the synthesis amount, reaction temperature and the like, and thus can not be generally defined, but it is usually set in the range of 1 to 10 hours, preferably 1 to 5 hours.

  Although the addition amount of the said phosphorus oxychloride is not specifically limited, Usually, it is 1.5-3.0 molar equivalent with respect to the said compound (A), It is a reaction that it is 1.8-3.0 molar equivalent. It is preferable from the point which improves a yield.

  The coloring material (1) represented by the general formula (I) can be obtained by mixing the chloride of triarylmethane obtained by the above reaction with a desired anion in a solvent.

<Other color materials>
(A) The colorant may be blended with other colorants as needed for the purpose of controlling the color tone, as long as the effects of the present invention are not impaired. As other coloring materials, for example, conventionally known pigments and dyes can be selected according to the purpose, and one or more kinds can be used.
Specific examples of the other colorants include, for example, C.I. I. Pigment violet 1, C.I. I. Pigment violet 2, C.I. I. Pigment violet 3, C.I. I. Pigment violet 19, C.I. I. Pigment violet 23; C.I. I. Pigment blue 1, C.I. I. Pigment blue 15, C.I. I. Pigment blue 15: 3, C.I. I. Pigment blue 15: 4, C.I. I. Pigment blue 15: 6, C.I. I. Pigment blue 60, C.I. I. Pigment red 81, C.I. I. And pigments such as pigment red 82 and dyes such as acid red.

  The blending amount of the other coloring materials is preferably 40 parts by mass or less, and more preferably 20 parts by mass or less based on 100 parts by mass of the total amount of the coloring material (A). Within this range, it is possible to control the color tone without impairing the high transmittance characteristic of the color material represented by the general formula (I) and the heat resistance and light resistance characteristics. .

The average dispersed particle diameter of the colorant (A) used in the present invention is not particularly limited as long as it can form a desired color when it is used as a colored layer of a color filter, and the contrast is improved. From the viewpoint of excellent heat resistance and light resistance, the thickness is preferably in the range of 10 to 200 nm, and more preferably in the range of 20 to 150 nm. (A) When the average dispersed particle diameter of the coloring material is in the above range, the liquid crystal display and the light emitting display manufactured using the coloring material dispersion liquid of the present invention have high contrast and high quality. be able to.
The average dispersed particle diameter of the (A) colorant in the colorant dispersion is the dispersed particle diameter of the colorant particles dispersed in at least the solvent-containing dispersion medium, and is measured by a laser light scattering particle size distribution analyzer. It is As a measurement of the particle size by a laser light scattering particle size distribution analyzer, the solvent used in the colorant dispersion liquid is appropriately diluted (for example, 1000 times) to a concentration that can be measured by the laser light scattering particle size distribution analyzer And the like, and can be measured at 23 ° C. by a dynamic light scattering method using a laser light scattering particle size distribution analyzer (for example, Nanotrac particle size distribution measuring apparatus UPA-EX150 manufactured by Nikkiso Co., Ltd.). The average dispersed particle size here is a volume average particle size.

In the colorant dispersion of the present invention, the content of the colorant is not particularly limited. From the viewpoint of dispersibility and dispersion stability, the content of the colorant is preferably in the range of 5 to 40% by mass, and more preferably 10 to 20% by mass, with respect to the total amount of the colorant dispersion.
In the color material dispersion liquid of the present invention, when the color material (1) represented by the general formula (I) and other color materials are mixed and used as the color material (A), the mixing ratio is desired In order to adjust to the color tone, it may set suitably, and is not specifically limited. From the viewpoint of heat resistance, the color material (1) is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, and 80 parts by mass or more in 100 parts by mass of the total amount of the coloring material (A). It is further preferred that

[(B) Dispersant]
In the coloring material dispersion liquid of the present invention, the coloring material (1) represented by at least the general formula (I) in the coloring material (A) is used by being dispersed in a solvent by the (B) dispersing agent. (B) As a dispersing agent, it can select suitably from what is conventionally used as a dispersing agent, and can be used. As a specific example of a dispersing agent, surfactant, such as cationic type, anionic type, nonionic type, amphoteric, silicone type, a fluorine type, can be used, for example. Among the surfactants, polymer surfactants (polymer dispersants) are preferable in that they can be dispersed uniformly and finely.

  As the polymer dispersant, for example, (co) polymers of unsaturated carboxylic acid ester such as polyacrylic acid ester; (partial) amine salt of (co) polymer of unsaturated carboxylic acid such as polyacrylic acid (Partially) ammonium salts and (partially) alkylamine salts; (co) polymers of hydroxyl group-containing unsaturated carboxylic acid esters such as hydroxyl group-containing polyacrylic acid esters and modified products thereof; polyurethanes; unsaturated polyamides; Long-chain polyamino amide phosphates; Polyethylenimine derivatives (amides obtained by reaction of poly (lower alkylenimine) with free carboxyl group-containing polyesters and their bases); Polyallylamine derivatives (polyallylamine and free carboxyls) Co-Condensation of Polyester, Polyamide or Ester Having a Group The reaction product obtained by reacting one or more compound selected from among the three compounds of (polyester amide)), and the like.

  As a commercial item of such a dispersing agent, for example, Disperbyk-2000, 2001, BYK-LPN 6919, 21116 (above, made by Big Chemie Japan KK), Ajispar PB 821, 881 (made by Ajinomoto Co., Ltd.), etc. are mentioned. be able to. Among them, BYK-LPN 6919 and 21116 are preferable in terms of heat resistance, electrical reliability, and dispersibility.

Among them, as the polymer dispersant, a polymer having at least a structural unit represented by the following general formula (II), from the viewpoint of being able to suitably disperse the coloring material (1) and having good dispersion stability, And it is preferable that it is 1 or more types selected from the group which consists of a urethane type dispersing agent which consists of a compound which has 1 or more urethane bond (-NH-COO-) in 1 molecule.
The above-mentioned preferable dispersants will be described in detail below.

<A polymer having a constitutional unit represented by at least the following general formula (II)>
In the present invention, as the (B) dispersant, a polymer having at least a constitutional unit represented by the following general formula (II) can be suitably used.

(In the general formula (II), R ¹¹ is a hydrogen atom or a methyl group, A is a direct bond or a divalent linking group, and Q is a group represented by the following general formula (II-a), or a substituted group Represents a saltable nitrogen-containing heterocyclic group which may have a group)

(In general formula (II-a), R ¹² and R ¹³ each independently represent a hydrogen atom or a hydrocarbon group which may contain a hetero atom, and R ¹² and R ¹³ are the same or different from each other May be

In the general formula (II), A is a direct bond or a divalent linking group. The direct bonding means that Q is directly bonded to a carbon atom in the general formula (II) without a linking group.
As a bivalent coupling group in A, a C1-C10 alkylene group, an arylene group, -CONH- group, -COO- group, a C1-C10 ether group (-R'-OR) is mentioned, for example "-: R 'and R" each independently represent an alkylene group), a combination thereof and the like.
Among them, from the viewpoint of dispersibility, A in the general formula (II) is preferably a direct bond, a -CONH- group, or a divalent linking group containing a -COO- group.

  In addition, it can be particularly suitably used by forming a constituent unit represented by the above general formula (II) of these dispersants in an arbitrary ratio with a salt forming agent described below.

As a polymer which has a structural unit represented by general formula (II), a WO2011 / 108495 pamphlet, Unexamined-Japanese-Patent 2013-054200, Unexamined-Japanese-Patent 2010-237608, 2011-75661 among others are mentioned. Block copolymer having the structure described in the above, and graft copolymer improve the dispersibility and dispersion stability of the color material and the heat resistance of the resin composition, and can form a high brightness and high contrast colored layer It is preferable from
Moreover, BYK-LPN6919 etc. are mentioned as a commercial item of the polymer which has a structural unit represented by General formula (II).

(Salt forming agent)
In the present invention, the dispersant is also preferably a polymer in which at least a part of the nitrogen moiety of the constituent unit represented by the above general formula (II) has formed a salt (hereinafter may be referred to as salt modification). be able to.
In the present invention, the salt forming agent is used to salt the nitrogen moiety of the constituent unit represented by the general formula (II), thereby strongly adsorbing the dispersant to the coloring material similarly forming a salt. By doing this, the dispersibility and dispersion stability of the coloring material are improved. As a salt formation agent, the acidic organic phosphorus compound of WO2011 / 108495 pamphlet, Unexamined-Japanese-Patent No. 2013-054200, an organic sulfonic acid compound, a quaternizing agent etc. can be used conveniently. In particular, when the salt forming agent is an acidic organic phosphorus compound, the coloring material surface is phosphated by the localization of the salt formation site containing the acidic organic phosphorus compound of the dispersing agent on the particle surface of the coloring material. As a result of being in a coated state, attack (hydrogen abstraction) on the dye skeleton of the coloring material by active oxygen is suppressed, and the heat resistance and light resistance of the coloring material including the dye skeleton are improved. Therefore, when a polymer salt-denatured with an acidic organic phosphorus compound is used as a dispersant, it is possible to further suppress the color fading at the time of high temperature heating in a state where the high transmittance color material (A) used in the present invention is well dispersed. Thus, a colored layer having higher brightness can be formed even after the high temperature heating step in the color filter manufacturing step.

<Urethane-based dispersant>
Moreover, the urethane type dispersing agent suitably used as a dispersing agent is a dispersing agent which consists of a compound which has one or more urethane bond (-NH-COO-) in 1 molecule.
By using a urethane dispersant, good dispersion can be achieved with a small amount. By setting the amount of the dispersing agent to a small amount, it is possible to relatively increase the compounding amount of the curing component and the like, and as a result, it is possible to form a colored layer excellent in heat resistance.

  In the present invention, among the urethane dispersants, (1) polyisocyanates having two or more isocyanate groups in one molecule, (2) polyesters having a hydroxyl group at one end or both ends, and one end or one end It is preferably a reaction product with one or more selected from poly (meth) acrylates having hydroxyl groups at both ends, and (1) polyisocyanates having two or more isocyanate groups in one molecule And (2) at least one selected from polyesters having a hydroxyl group at one end or both ends, and poly (meth) acrylates having a hydroxyl group at one end or both ends, and (3) active hydrogen in the same molecule More preferably, it is a reaction product of a compound having a basic group or an acidic group.

  Commercially available urethane dispersants include Disperbyk-161, 162, 163, 164, 167, 168, 170, 171, 174, 182, 183, 184, 185, BYK-9077 (all, Big Chemie Japan KK) And Ajispar PB 711 (manufactured by Ajinomoto Co., Ltd.), EFKA-46, 47 and 48 (manufactured by EFKA CHEMICALS), and the like. Among them, Disperbyk-161, 162, 166, 170, and 174 are preferable in terms of heat resistance, electrical reliability, and dispersibility.

  In the color material dispersion liquid of the present invention, the content of the dispersant is not particularly limited as long as the effects of the present invention are not impaired, but from the viewpoint of the dispersibility of the color material and the dispersion temporal stability, the (A) color material The amount is preferably 5 to 100 parts by mass, more preferably 10 to 80 parts by mass with respect to 100 parts by mass.

(C) Solvent In the present invention, the (C) solvent does not react with each component in the colorant dispersion, and can be appropriately selected from solvents which can dissolve or disperse these. Specifically, alcohol type; ether alcohol type; ester type; ketone type; ether alcohol acetate type; ether type; aprotic amide type; lactone type; unsaturated hydrocarbon type; organic solvent such as saturated hydrocarbon type Among them, it is preferable to use an ester solvent from the viewpoint of solubility at the time of dispersion and coating suitability.

Preferred ester solvents include, for example, methyl methoxypropionate, ethyl ethoxypropionate, methoxyethyl acetate, propylene glycol monomethyl ether acetate, 3-methoxy-3-methyl-1-butyl acetate, 3-methoxybutyl acetate, methoxybutyl Acetate, ethoxyethyl acetate, ethyl cellosolve acetate, dipropylene glycol methyl ether acetate, propylene glycol diacetate, 1,3-butylene glycol diacetate, cyclohexanol acetate, 1,6-hexanediol diacetate, diethylene glycol monoethyl ether acetate, Diethylene glycol monobutyl ether acetate etc. are mentioned.
Above all, it is preferable to use propylene glycol monomethyl ether acetate (PGMEA) from the viewpoints of low danger to human body and low volatility at around room temperature but good heat drying property. In this case, there is an advantage that a special cleaning step is not required even when switching to a colored resin composition using conventional PGMEA.

These solvents may be used alone or in combination of two or more.
The color material dispersion liquid of the present invention is prepared using a solvent such as described above in a proportion of usually 60 to 85% by mass with respect to the total amount of the color material dispersion liquid containing the solvent. When the amount of the solvent is too small, the viscosity increases and the dispersibility tends to be reduced. When the amount of the solvent is too large, the concentration of the coloring material may be lowered, and it may be difficult to achieve the target chromaticity coordinates after preparation of the resin composition.

(Other ingredients)
In the color material dispersion liquid of the present invention, a dispersion assisting resin and other components may be blended, if necessary, as long as the effects of the present invention are not impaired.
As a dispersion | distribution auxiliary | assistant resin, the alkali-soluble resin mentioned later is mentioned, for example. The steric hindrance of the alkali-soluble resin makes it difficult for the coloring material particles to come in contact with each other, and there are cases where it is possible to reduce the dispersing agent by the dispersion stabilization or the dispersion stabilization effect.
Further, as other components, for example, a surfactant for improving wettability, a silane coupling agent for improving adhesion, an antifoaming agent, a repelling agent, an antioxidant, an aggregation inhibitor, and a UV absorber Etc.

<Method of Manufacturing Colorant Dispersion>
In the colorant dispersion of the present invention, the dispersant is mixed with a solvent and stirred to prepare a dispersant solution, and then the colorant and other compounds are mixed with the dispersant solution if necessary, and a disperser is prepared. It can be prepared by dispersing using The colorant dispersion of the present invention may be prepared by mixing a colorant and a dispersant with a solvent and dispersing the mixture using a known disperser.

  Examples of the disperser for performing the dispersion treatment include roll mills such as 2 rolls and 3 rolls, ball mills such as ball mill and vibration ball mill, paint conditioners, bead mills such as continuous disc type bead mill and continuous annular type bead mill. As a preferable dispersion condition of a bead mill, as for the bead diameter to be used, 0.03-2.00 mm is preferable, More preferably, it is 0.10-1.0 mm.

  Specifically, preliminary dispersion is performed using 2 mm zirconia beads having relatively large bead diameters, and further, main dispersion using 0.1 mm zirconia beads having relatively small bead diameters is mentioned. Moreover, it is preferable to filter with a 0.1-0.5 micrometer membrane filter after dispersion | distribution.

  In the present invention, the dispersion time to be dispersed using a known disperser is appropriately adjusted and is not particularly limited, but from the viewpoint of achieving high transmittance by miniaturizing the color material represented by the general formula (I). It is preferable to set to 5 to 40 hours.

  The coloring material dispersion of the present invention is suitably used as a pre-preparation for preparing a colored resin composition for color filter described later. That is, with the colorant dispersion liquid, the mass of solid components other than the colorant components in the composition (mass of colorant components in the composition) / (prepared in the preparation of the colored resin composition described later) 2.) Colorant dispersion with high ratio. Specifically, the ratio (mass of color material component in the composition) / (mass of solid content other than the color material component in the composition) is usually 1.0 or more. A colored resin composition for color filter having excellent dispersibility can be prepared by mixing the colorant dispersion and each component described later.

[Colored resin composition for color filter]
The colored resin composition for a color filter according to the present invention contains (A) a colorant, (B) a dispersant, (C) a solvent, and (D) a binder component, and the (A) colorant is And a coloring material (1) represented by the general formula (I).

The colored resin composition for a color filter of the present invention can form a colored layer having excellent heat resistance, high brightness and high contrast by containing the color material dispersion according to the present invention.
When the colored resin composition for a color filter according to the present invention is used as a photosensitive resin composition to be described later, developability is good. Usually, the cationic dye has a reduced solubility in an aqueous alkali solution at the time of development due to electrostatic interaction between an acrylic acid group in an alkali-soluble resin described later and a cation of the dye. In particular, when it is uniformly dissolved in the resin composition, the effect is large, so the development solubility is poor. On the other hand, in the colored resin composition for a color filter according to the present invention, since the coloring material represented by the general formula (I) is dispersed by the dispersing agent, the dispersing agent covers the periphery of the coloring material particles and the steric hindrance It is presumed that the compound has sufficient development solubility because the above-mentioned electrostatic interaction with the alkali-soluble acrylic acid group is eliminated.

The colored resin composition for color filters of the present invention contains at least (A) a coloring material, (B) a dispersant, (C) a solvent, and (D) a binder component, and the effect of the present invention As long as it does not impair, it may have other components as needed.
Hereinafter, each component of the colored resin composition for color filters of this invention is demonstrated in detail.
The components that can be contained in the colorant dispersion according to the present invention can be the same as those described in the section of the colorant dispersion, so the description thereof is omitted here.

[Binder component]
The colored resin composition for color filter of the present invention contains a binder component in order to impart film formability and adhesion to the surface to be coated. Among them, in order to impart sufficient hardness to the coating film, it is preferable to contain a curable binder component. The curable binder component is not particularly limited, and a curable binder component used to form a colored layer of a conventionally known color filter can be appropriately used.
As the curable binder component, for example, a photocurable binder component containing a photocurable resin that can be polymerized and cured by visible light, ultraviolet light, electron beam or the like, or a thermosetting resin that can be polymerized and cured by heating What contains the thermosetting binder component which can be used can be used.

When the colored resin composition for color filter is used in an ink jet system, for example, when a colored layer can be formed by selectively adhering it on a substrate in a pattern, developability is required for the curable binder component Absent. In this case, a known thermosetting binder component, a photosensitive binder component or the like used when forming a color filter colored layer by an inkjet method etc. can be used appropriately.
As the thermosetting binder, a combination of a compound having two or more thermosetting functional groups in one molecule and a curing agent is usually used, and a catalyst capable of promoting a thermosetting reaction may be further added. As a thermosetting functional group, an epoxy group, oxetanyl group, an isocyanate group, an ethylenically unsaturated bond, etc. are mentioned. An epoxy group is preferably used as the thermosetting functional group. As a specific example of a thermosetting binder component, the thing of Unexamined-Japanese-Patent No. 2013-250446 can be mentioned, for example.

On the other hand, when using a photolithography process when forming a colored layer, the photosensitive binder component which has alkali developability is used suitably.
Hereinafter, although a photosensitive binder component is demonstrated, a curable binder component is not limited to these. In addition to the photosensitive binder component described below, a thermosetting binder component that can be polymerized and cured by heating, such as an epoxy resin, may be further used.

  Examples of the photosensitive binder component include a positive photosensitive binder component and a negative photosensitive binder component. Examples of the positive photosensitive binder component include a system including an alkali-soluble resin and an o-quinonediazide group-containing compound as a photosensitivity imparting component.

On the other hand, as the negative photosensitive binder component, a system containing at least an alkali soluble resin, a polyfunctional monomer and a photoinitiator is suitably used.
In the colored resin composition for color filters of the present invention, it is preferable that it is a negative photosensitive binder component from the viewpoint that a pattern can be easily formed by photolithography using an existing process.
The alkali-soluble resin, the polyfunctional monomer, and the photoinitiator, which constitute the negative photosensitive binder component, will be specifically described below.

(1) Alkali-Soluble Resin The alkali-soluble resin in the present invention has an acidic group, acts as a binder resin, and as long as it is soluble in a developer used when forming a pattern, particularly preferably an alkaline developer, It can be selected appropriately and used.
The preferred alkali-soluble resin in the present invention is a resin having a carboxyl group as an acidic group, and specifically, an acrylic copolymer having a carboxyl group, an epoxy (meth) acrylate resin having a carboxyl group, etc. It can be mentioned. Among these, particularly preferred are those having a carboxyl group in the side chain and further having a photopolymerizable functional group such as an ethylenically unsaturated group in the side chain. It is because the film strength of the cured film formed by containing a photopolymerizable functional group is improved. In addition, these acrylic copolymers and epoxy acrylate resins may be used as a mixture of two or more.

The acrylic copolymer having a carboxyl group is obtained by copolymerizing a carboxyl group-containing ethylenically unsaturated monomer and an ethylenically unsaturated monomer.
The acrylic copolymer having a carboxyl group may further contain a structural unit having an aromatic carbon ring. The aromatic carbon ring functions as a component that imparts coating properties to the colored resin composition for color filter.
The acrylic copolymer having a carboxyl group may further contain a structural unit having an ester group. The structural unit having an ester group not only functions as a component that suppresses the alkali solubility of the colored resin composition for color filter, but also functions as a component that improves the solubility in a solvent and the solvent resolubility.

As a specific example of the acryl-type copolymer which has a carboxyl group, the thing of Unexamined-Japanese-Patent No. 2013-250446 can be mentioned, for example, Specifically, For example, methyl (meth) acrylate, ethyl (meta A copolymer comprising a monomer having no carboxyl group such as acrylate) and one or more selected from (meth) acrylic acid and its anhydride can be exemplified. In addition, for example, polymers in which an ethylenically unsaturated bond is introduced by adding an ethylenically unsaturated compound having a reactive functional group such as a glycidyl group or a hydroxyl group to the above-mentioned copolymer can be exemplified, but the present invention is limited thereto It is not something to be done.
Among these, polymers or the like into which an ethylenically unsaturated bond is introduced by addition of an ethylenically unsaturated compound having a glycidyl group or a hydroxyl group to a copolymer are polymerized with a polyfunctional monomer described later at the time of exposure. Is particularly preferable in that the colored layer is more stable.

  The copolymerization ratio of the carboxyl group-containing ethylenically unsaturated monomer in the carboxyl group-containing copolymer is usually 5 to 50% by mass, preferably 10 to 40% by mass. In this case, if the copolymerization ratio of the carboxyl group-containing ethylenically unsaturated monomer is less than 5% by mass, the solubility of the obtained coating film in an alkali developer decreases, and pattern formation becomes difficult. On the other hand, if the copolymerization ratio exceeds 50% by mass, the formed pattern may tend to come off from the substrate or to roughen the surface of the pattern during development with an alkaline developer.

  The preferred molecular weight of the carboxyl group-containing copolymer is preferably in the range of 1,000 to 500,000, and more preferably 3,000 to 200,000. If it is less than 1,000, the binder function after curing is significantly reduced, and if it exceeds 500,000, pattern formation may be difficult at the time of development with an alkali developer.

The epoxy (meth) acrylate resin having a carboxyl group is not particularly limited, but an epoxy (meth) obtained by reacting a reaction product of an epoxy compound and an unsaturated group-containing monocarboxylic acid with an acid anhydride. Acrylate compounds are suitable.
The epoxy compound, the unsaturated group-containing monocarboxylic acid, and the acid anhydride can be appropriately selected from known ones and used. As a specific example, the thing of Unexamined-Japanese-Patent No. 2013-250446, etc. are mentioned, for example. The epoxy compound, unsaturated group-containing monocarboxylic acid, and acid anhydride may be used alone or in combination of two or more.

  The alkali-soluble resin used in the colored resin composition for color filter may be used singly or in combination of two or more types, and as the content thereof, the color contained in the colored resin composition The amount is usually in the range of 10 to 1000 parts by mass, preferably in the range of 20 to 500 parts by mass with respect to 100 parts by mass of the material. If the content of the alkali-soluble resin is too small, sufficient alkali developability may not be obtained, and if the content of the alkali-soluble resin is too large, the proportion of the coloring material becomes relatively low, which is sufficient. In some cases, the color density can not be obtained.

(2) Polyfunctional Monomer The polyfunctional monomer used in the colored resin composition for color filter is not particularly limited as long as it can be polymerized by a photoinitiator described later, and is usually an ethylenically unsaturated double bond. It is preferable that it is a polyfunctional (meth) acrylate in which the compound which has two or more is used, especially having two or more acryloyl group or methacryloyl group.
As such a polyfunctional (meth) acrylate, it may select suitably from conventionally well-known things, and may be used. As a specific example, the thing of Unexamined-Japanese-Patent No. 2013-250446, etc. are mentioned, for example.

One of these polyfunctional (meth) acrylates may be used alone, or two or more thereof may be used in combination. In addition, when excellent photocurability (high sensitivity) is required for the colored resin composition for color filter of the present invention, the polyfunctional monomer has three or more polymerizable double bonds (trifunctional) or more. And poly (meth) acrylates of polyhydric alcohols having a valence of 3 or more and dicarboxylic acid modified products thereof. Specifically, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth ) Acrylate, succinic acid modified product of pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol penta (meth) acrylate Acid modified product of dipentae Sri Tall hexa (meth) acrylate are preferable.
The content of the polyfunctional monomer used in the colored resin composition for color filter is not particularly limited, but generally about 5 to 500 parts by mass, preferably 20 to 300 parts by mass with respect to 100 parts by mass of the alkali-soluble resin. The scope of the department. If the content of the polyfunctional monomer is less than the above range, light curing may not proceed sufficiently, and the exposed portion may elute. If the content of the polyfunctional monomer is more than the above range, the alkali developability may be reduced. There is.

(3) Photo-initiator The photo-initiator to be used in the colored resin composition for color filter is not particularly limited, and is used by combining one or two or more kinds out of conventionally known various photo-initiators. be able to. As a specific example, the thing of Unexamined-Japanese-Patent No. 2013-250446, etc. are mentioned, for example.

  The content of the photoinitiator used in the colored resin composition for color filter is usually about 0.01 to 100 parts by mass, preferably 5 to 60 parts by mass, with respect to 100 parts by mass of the polyfunctional monomer. If this content is less than the above range, a sufficient polymerization reaction can not be generated, and therefore the hardness of the colored layer may not be sufficient. On the other hand, if it is more than the above range, the colored resin for color filter The content of the coloring material and the like in the solid content of the composition may be relatively small, and a sufficient coloring density may not be obtained.

  Further, in the colored resin composition for color filter of the present invention, further, a polymerization terminator, a chain transfer agent, a leveling agent, a plasticizer, a surfactant, an antifoaming agent, a silane coupling agent, an ultraviolet light absorber, adhesion promotion You may contain an agent etc.

<Mixing ratio of each component in colored resin composition for color filter>
The total content of the color material (A) is preferably blended at a ratio of 3 to 65% by mass, more preferably 4 to 55% by mass, with respect to the total solid content of the colored resin composition for color filter. If it is more than the said lower limit, the colored layer at the time of apply | coating the colored resin composition for color filters to a predetermined | prescribed film thickness (usually 1.0-5.0 micrometers) has sufficient color density. Moreover, if it is below the said upper limit, while it is excellent in dispersibility and dispersion stability, the colored layer which has sufficient hardness and adhesiveness with a board | substrate can be obtained. In the present invention, the solid content is all other than the above-mentioned solvents, and also includes liquid polyfunctional monomers and the like.
Further, the content of the dispersant (B) is not particularly limited as long as the colorant (A) can be uniformly dispersed, but, for example, the solid resin of the colored resin composition for color filter 3-40 mass% can be used with respect to the whole quantity. Furthermore, it is preferable to mix | blend in the ratio of 5-35 mass% with respect to solid content whole quantity of colored resin composition for color filters, and it is preferable to mix | blend in the ratio of 5-25 mass% especially. If it is more than the said lower limit, it will be excellent in the dispersibility and dispersion stability of (A) coloring material, and will be excellent in storage stability. Further, if it is not more than the above upper limit value, developability becomes good.
The total amount of the binder component is preferably 10 to 92% by mass, preferably 15 to 87% by mass, based on the total solid content of the colored resin composition for color filter. If it is more than the said lower limit, the colored layer which has sufficient hardness and adhesiveness with a board | substrate can be obtained. Moreover, if it is below the said upper limit, it is excellent in developability, or generation | occurrence | production of the fine wrinkles by heat shrinkage is also suppressed.
Moreover, what is necessary is just to set content of the (C) solvent suitably in the range which can form a colored layer accurately. It is preferably in the range of 55 to 95% by mass, more preferably in the range of 65 to 88% by mass, based on the total amount of the colored resin composition for color filters containing the solvent. . When the content of the solvent is in the above range, the coating property can be excellent.

<Method of producing colored resin composition for color filter>
The method for producing a colored resin composition for color filter comprises (A) a color material, (B) a dispersant, (C) a solvent, a binder component, and various additive components optionally used (A The coloring material is not particularly limited as long as the coloring material can be uniformly dispersed in the solvent (C) than the dispersing agent (B), and it can be prepared by mixing using a known mixing means.
As a manufacturing method of the colored resin composition for the said color filter, for example, after mixing a (1) (A) coloring material, a (B) dispersing agent, and a (C) solvent and preparing a coloring material dispersion liquid A method of mixing a binder component and various additive components optionally used in the color material dispersion; (2) (C) in a solvent, (A) a colorant, (B) a dispersant, and a binder component And a method of simultaneously charging and mixing various additive components optionally used; (3) (C) adding a dispersant, a binder component, and various additive components optionally used in a solvent (A) a method of adding and mixing a colorant, and the like.
Among these methods, the method of the above (1) is preferable from the viewpoint of effectively preventing aggregation of the coloring material and uniformly dispersing it. In the method of the above (1), as a method of preparing the colorant dispersion, any method may be used as long as the colorant (A) can be uniformly dispersed in the solvent by the dispersant, and known mixing means can be used. .

  Examples of the disperser for performing the dispersion treatment include roll mills such as 2 rolls and 3 rolls, ball mills such as ball mill and vibration ball mill, paint conditioners, bead mills such as continuous disc type bead mill and continuous annular type bead mill. As a preferable dispersion condition of a bead mill, as for the bead diameter to be used, 0.03-2.00 mm is preferable, More preferably, it is 0.10-1.0 mm.

  Specifically, preliminary dispersion is performed using 2 mm zirconia beads having relatively large bead diameters, and further, main dispersion using 0.1 mm zirconia beads having relatively small bead diameters is mentioned. Moreover, it is preferable to filter with a 0.5-5.0 micrometers membrane filter after dispersion | distribution.

3. Color Filter The color filter according to the present invention is a color filter comprising at least a transparent substrate and a colored layer provided on the transparent substrate, wherein at least one of the colored layers is represented by the following general formula (I) A color material (1).

(Each symbol in the general formula (I) is as described above.)

  Such a color filter according to the present invention will be described with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing an example of the color filter of the present invention. According to FIG. 1, the color filter 10 of the present invention has a transparent substrate 1, a light shielding portion 2, and a colored layer 3.

(Colored layer)
At least one of the colored layers used in the color filter of the present invention is a colored layer containing a coloring material (1) represented by the general formula (I).
The colored layer is usually formed at an opening of a light shielding portion on a transparent substrate described later, and is usually formed of a coloring pattern of three or more colors.
Moreover, it does not specifically limit as arrangement | sequence of the said colored layer, For example, it can be set as general arrangement, such as stripe type, mosaic type, triangle type, 4 pixel arrangement | positioning type | mold. In addition, the width, area, and the like of the colored layer can be set arbitrarily.
The thickness of the colored layer is appropriately controlled by adjusting the coating method, the solid content concentration, the viscosity, and the like of the colored resin composition for a color filter, but in general, the range of 1 to 5 μm is preferable.

The colored layer containing the coloring material (1) represented by the above general formula (I) used in the color filter of the present invention is preferably formed using the colored resin composition for a color filter according to the present invention It is preferable that it is a hardened | cured material of the said colored resin composition for color filters. The said colored layer can be formed by the following method, for example, when the said colored resin composition for color filters is a photosensitive resin composition.
First, a colored resin composition for color filter is coated on a transparent substrate to be described later using a coating method such as a spray coating method, dip coating method, bar coating method, call coating method, spin coating method, etc. To form
Next, the wet coating film is dried using a hot plate, an oven or the like, exposed to light through a mask of a predetermined pattern, and photopolymerized with an alkali-soluble resin, a polyfunctional monomer, etc. It is a photosensitive coating film. As a light source used for exposure, ultraviolet rays, such as a low pressure mercury lamp, a high pressure mercury lamp, and a metal halide lamp, an electron beam etc. are mentioned, for example. The exposure amount is appropriately adjusted depending on the light source to be used, the thickness of the coating film, and the like.
Further, heat treatment may be performed to promote the polymerization reaction after exposure. The heating conditions are appropriately selected depending on the blending ratio of each component in the colored resin composition for color filter to be used, the thickness of the coating film, and the like.

Next, development processing is performed using a developer, and the unexposed area is dissolved and removed to form a coating film in a desired pattern. As a developing solution, usually, a solution in which an alkali is dissolved in water or a water-soluble solvent is used. An appropriate amount of surfactant or the like may be added to the alkaline solution. Moreover, the developing method can employ | adopt a general method.
After the development treatment, usually, washing of the developing solution and drying of the cured coating film of the colored resin composition for color filter are performed to form a colored layer. In addition, you may heat-process in order to fully harden a coating film after image development processing. There is no limitation in particular as heating conditions, According to the use of a coating film, it selects suitably.

(Light blocking part)
The light shielding portion in the color filter of the present invention is formed in a pattern on a transparent substrate described later, and can be the same as that used as a light shielding portion in a general color filter.
It does not specifically limit as a pattern shape of the said light-shielding part, For example, shapes, such as stripe form and a matrix form, are mentioned. Examples of the light shielding portion include those obtained by dispersing or dissolving a black pigment in a binder resin, and metal thin films such as chromium and chromium oxide. The metal thin film, CrO _x film (x is an arbitrary number) may be one and the Cr film is two-layered, also, CrO _x film (x is an arbitrary number) with reduced more reflectivity Alternatively, three layers of CrN _y films (y is an arbitrary number) and Cr films may be stacked.
When the light shielding portion is obtained by dispersing or dissolving a black color material in a binder resin, a method of forming the light shielding portion is not particularly limited as long as the light shielding portion can be patterned. For example, the photolithography method, the printing method, the inkjet method etc. using the coloring resin composition for light-shielding parts can be mentioned.

  The film thickness of the light shielding portion is set to about 0.2 to 0.4 μm in the case of a metal thin film, and in the case of about 0.5 to 2 μm in the case where a black color material is dispersed or dissolved in a binder resin. It is set.

(Transparent substrate)
The transparent substrate in the color filter of the present invention is not particularly limited as long as it is a substrate transparent to visible light, and a transparent substrate used for a general color filter can be used. Specifically, it has flexibility and flexibility such as transparent non-flexible rigid material such as quartz glass, non-alkali glass, synthetic quartz plate, or transparent resin film, resin plate for optics, flexible glass, etc. A transparent flexible material is mentioned.
Although the thickness of the said transparent substrate is not specifically limited, According to the use of the color filter of this invention, a thing about 100 micrometers-about 1 mm can be used, for example.
The color filter of the present invention may have, for example, an overcoat layer, a transparent electrode layer, an alignment film, a columnar spacer, etc. in addition to the transparent substrate, the light shielding portion and the colored layer. .

4. Liquid Crystal Display Device The liquid crystal display device of the present invention is characterized by including the color filter according to the present invention described above, a liquid crystal layer, and a light resistant substrate. The liquid crystal display device of the present invention generally comprises the color filter of the present invention, a counter substrate, and a liquid crystal layer formed between the color filter and the counter substrate.
Such a liquid crystal display device of the present invention will be described with reference to the drawings. FIG. 2 is a schematic view showing an example of the liquid crystal display device of the present invention. As exemplified in FIG. 2, the liquid crystal display device 40 of the present invention includes a color filter 10, an opposing substrate 30 having an electrode substrate 22 on a transparent substrate 23, and between the color filter 10 and the opposing substrate 30. The liquid crystal layer 25 is formed, and the transparent electrode film 21 is provided between the color filter 10 and the liquid crystal layer 25.
The liquid crystal display device of the present invention is not limited to the configuration shown in FIG. 2 and can be generally known as a liquid crystal display device using a color filter.

The drive method of the liquid crystal display device of the present invention is not particularly limited, and a drive method generally used for a liquid crystal display device can be adopted. As such a driving method, for example, a TN method, an IPS method, an OCB method, an MVA method and the like can be mentioned. In the present invention, any of these systems can be suitably used.
Further, the substrate 21 and the substrate 22 can be appropriately selected and used according to the driving method of the liquid crystal display device of the present invention, and, for example, those having a transparent electrode and an alignment film on a transparent substrate can do.
Furthermore, as the liquid crystal constituting the liquid crystal layer, various liquid crystals having different dielectric anisotropy, and a mixture thereof can be used according to the driving method and the like of the liquid crystal display device of the present invention.

As a method of forming a liquid crystal layer, a method generally used as a method of manufacturing a liquid crystal cell can be used, and examples thereof include a vacuum injection method and a liquid crystal dropping method.
In the vacuum injection method, for example, a liquid crystal cell is prepared in advance using a color filter and an opposite substrate, and the liquid crystal is heated to be an isotropic liquid, and the liquid crystal cell is isotropic liquid using the capillary effect. The liquid crystal layer can be formed by injecting in the state of and sealing with an adhesive. Thereafter, by gradually cooling the liquid crystal cell to room temperature, the enclosed liquid crystal can be aligned.
In the liquid crystal dropping method, for example, a sealing agent is applied to the peripheral edge of the color filter, the color filter is heated to a temperature at which the liquid crystal becomes an isotropic phase, and the liquid crystal is dropped in the isotropic liquid state using a dispenser or the like. The liquid crystal layer can be formed by stacking the color filter and the counter substrate under reduced pressure and adhering them through a sealing agent. Thereafter, by gradually cooling the liquid crystal cell to room temperature, the enclosed liquid crystal can be aligned.

5. Light Emitting Display Device A light emitting display device according to the present invention includes the color filter according to the present invention described above and a light emitter.
Such a light emitting display device of the present invention will be described with reference to the drawings. FIG. 3 is a schematic view showing an example of the light emitting display device of the present invention. As illustrated in FIG. 3, the light emitting display device 100 of the present invention includes a color filter 10 and a light emitter 80. The organic protective layer 50 and the inorganic oxide film 60 may be provided between the color filter 10 and the light emitter 80.

As a method of laminating the light emitting body 80, for example, a method of sequentially forming the transparent anode 71, the hole injection layer 72, the hole transport layer 73, the light emitting layer 74, the electron injection layer 75, and the cathode 76 on the color filter Alternatively, the light-emitting body 80 formed on another substrate may be attached to the inorganic oxide film 60. The transparent anode 71, the hole injection layer 72, the hole transport layer 73, the light emitting layer 74, the electron injection layer 75, the cathode 76, and the other components in the light emitting body 80 may be appropriately known ones. The light emitting display device 100 manufactured in this manner is applicable to, for example, an organic EL display of a passive drive system and an organic EL display of an active drive system.
The light emitting display device of the present invention is not limited to the configuration shown in FIG. 3 and can be generally known as a light emitting display device using a color filter.

  Hereinafter, the present invention will be specifically described by way of examples. These descriptions do not limit the present invention.

Synthesis Example 1: Synthesis of Color Material A-1 and Color Material A-2
(1) Synthesis of Intermediate A 25 g (133.2 mmol) of 2-adamantanamine hydrochloride was added to 175 mL of water, then 5.9 g (147.5 mmol) of sodium hydroxide was added, and the mixture was stirred at room temperature for 1 hour. , Filtered. The cake was washed with water and dried to give 15.6 g of 2-adamantanamine.
In 50 mL of xylene, 26.0 g (270.6 mmol) of t-butoxy sodium, 13.9 g (91.9 mmol) of 2-adamantanamine, 0.51 g (1.94 mmol) of triphenylphosphine, 0.22 g (0.2 g) of palladium acetate. 98 mmol) was added, and it heated up to 110-115 degreeC. At the same temperature, 20.0 g (96.6 mmol) of 1-bromonaphthalene was added dropwise. After completion of the dropwise addition, reaction was carried out at the same temperature for 20 hours, water was added to the reaction solution, and the organic layer was washed. The organic layer was concentrated and purified by column chromatography (silica gel, developing solvent toluene / n-hexane) to obtain 3.5 g (yield 13%) of an intermediate A represented by the following general formula (1) .
The obtained compound was confirmed to be the target compound from the following analysis results.
MS (ESI) (m / z): 278 (M + H)

(2) Synthesis of Coloring Material A-1 In 15 g of chlorobenzene, 3.0 g (10.8 mmol) of the intermediate A, 4.8 g (14.8 mmol) of 4,4'-bis (diethylamino) benzophenone, phosphorus oxychloride 2.4g (15.7 mmol) was added and it was made to react at 40-45 degreeC for 2 hours. The reaction solution was extracted with chloroform, and the organic layer was washed with water and concentrated. The concentrate was purified by column chromatography (silica gel, developing solvent chloroform / methanol) to obtain 2.2 g (yield 33%) of a color material A-1 represented by the following chemical formula (2).
The obtained compound was confirmed to be the target compound from the following analysis results.
MS (ESI) (m / z): 584 (M +)
Elemental analysis values: CHN measured values (79.27%, 8.09%, 6.83%); theoretical values (79.39%, 8.12%, 6.77%)
Further, the coloring material A-1 has an absorption maximum at a wavelength of 600 nm, and the molar absorption coefficient at the maximum wavelength is 92600 L / (mol · cm).
The molar absorption coefficient was measured using a U-4100 spectrophotometer manufactured by Hitachi High-Technologies Corporation, using a 1 cm quartz cell at a sampling interval of 0.5 nm, and was calculated by the following equation.
Molar extinction coefficient (ε) = absorbance at maximum wavelength / molar concentration

(3) Synthesis of Color Material A-2 The Kanto Chemical 12 tungstoric acid n hydrate 1.84 g (0.52 mmol) was dissolved by heating in a mixture of 40 mL of methanol and 40 mL of water, and the color material A-1 was prepared. 1.0 g (1.6 mmol) was added and stirred for 1 hour. The precipitate was collected by filtration and washed with water. The obtained precipitate was dried under reduced pressure to obtain 2.4 g (yield 96%) of a color material A-2 represented by the following chemical formula (3).
The obtained compound (coloring material A-2) was confirmed to be a target compound from the following analysis results.
^{· 31 P NMR (d-dmso} , ppm) δ - 15.15
MS (MALDI) (m / z): 584 (M ⁺ ), 2879 (M ⁻ )
Elemental analysis value: CHN actual measurement value (31.85%, 8.10%, 6.93%); theoretical value (31.90%, 3.26%, 2.72%)
・ Fluorescent X-ray analysis: Mo / W actual ratio (0%, 100%); theoretical value (0%, 100)

The molar ratio of molybdenum to tungsten in the coloring material is determined by the following measurement conditions using a fluorescent X-ray analyzer (XRF: X-ray Fluorescence Analysis) (RIX-3100: manufactured by Rigaku Denki Kogyo Co., Ltd.) The analysis was performed, and the actual ratio was obtained from the detection results of Mo and W among the detected elements.
As measurement conditions of XRF, the measurement diameter of the above-mentioned coloring material is 30 mmφ, the measurement atmosphere is a vacuum state of 13 Pa, and the measurement elements are elements from B (boron) to U (uranium) in atomic number order.

Synthesis Example 2: Synthesis of Color Material B-1 and Color Material B-2
(1) Synthesis of Intermediate B 8.2 g (85.3 mmol) of sodium t-butoxy, 9.6 g (58.1 mmol) of 1-adamantane methylamine, 0.32 g (1.22 mmol) of triphenylphosphine in 32 mL of xylene 0.14 g (0.62 mmol) of palladium acetate was added, and it heated up to 110-115 degreeC. At the same temperature, 12.6 g (60.8 mmol) of 1-bromonaphthalene was added dropwise. After completion of the dropwise addition, reaction was carried out at the same temperature for 20 hours, water was added to the reaction solution, and the organic layer was washed. The organic layer was concentrated and purified by column chromatography (silica gel, developing solvent toluene / n-hexane) to obtain 2.5 g (yield 14%) of an intermediate B represented by the following general formula (4) .
The obtained compound was confirmed to be the target compound from the following analysis results.
MS (ESI) (m / z): 292 (M + H)

(2) Synthesis of coloring material B-1 In 11.0 g of chlorobenzene, 2.2 g (7.5 mmol) of intermediate B, 3.6 g (11.1 mmol) of 4,4'-bis (diethylamino) benzophenone, oxychloride 1.8 g (11.7 mmol) of phosphorus was added and allowed to react at 40-45 ° C. for 2 hours. The reaction solution was extracted with chloroform, and the organic layer was washed with water and concentrated. The concentrate was purified by column chromatography (silica gel, developing solvent chloroform / methanol) to obtain 1.3 g (yield 25%) of a color material B-1 represented by the following chemical formula (5).
The obtained compound was confirmed to be the target compound from the following analysis results.
MS (ESI) (m / z): 598 (M +)
Elemental analysis value: CHN actual measurement value (79.71%, 8.18%, 6.76%); theoretical value (79.52%, 8.26%, 6.62%)
Further, the coloring material B-1 has an absorption maximum at a wavelength of 586 nm, and the molar absorption coefficient at the maximum wavelength is 83600 L / (mol · cm).

(3) Synthesis of Color Material B-2 Subsequently, in (3) of Synthesis Example 1 and (3) of Synthesis Example 1, except that Color material B-1 was used instead of Color material A-1 Similarly, a color material B-2 represented by the following chemical formula (6) was obtained (yield: 97%).
It was confirmed that the obtained compound (coloring material B-2) is a target compound from the following analysis results.
31P NMR (d-dmso, ppm) δ-15.15
MS (MALDI) (m / z): 598 (M +), 2879 (MH2-)
Elemental analysis value: CHN actual measurement value (32.45%, 3.42%, 2.65%); theoretical value (32.38%, 3.36%, 2.70%)
・ Fluorescent X-ray analysis: MoW actual ratio (0%, 100%); theoretical value (0%, 100)

Synthesis Example 3: Synthesis of Color Material C-1 and Color Material C-2
(1) Synthesis of Intermediate C 16.2 g (168.6 mmol) of t-butoxy sodium, 11.4 g (115.0 mmol) of cyclohexylamine, 0.63 g (2.40 mmol) of triphenylphosphine, palladium acetate in 62 mL of xylene 0.27 g (1.20 mmol) was added, and it heated up to 110-115 degreeC. At the same temperature, 25.0 g (120.7 mmol) of 1-bromonaphthalene was added dropwise. After completion of the dropwise addition, reaction was carried out at the same temperature for 20 hours, water was added to the reaction solution, and the organic layer was washed. The organic layer was concentrated and purified by column chromatography (silica gel, developing solvent toluene / n-hexane) to obtain 5.9 g (yield 22%) of an intermediate C represented by the following general formula (7) .
The obtained compound was confirmed to be the target compound from the following analysis results.
MS (ESI) (m / z): 226 (M + H)

(2) Synthesis of coloring material C-1 In 25 g of chlorobenzene, 5.0 g (22.2 mmol) of the intermediate C, 9.9 g (30.5 mmol) of 4,4'-bis (diethylamino) benzophenone, phosphorus oxychloride 4.9 g (32.0 mmol) was added and allowed to react at 40-45 ° C. for 3 hours. The reaction solution was extracted with chloroform, and the organic layer was washed with water and concentrated. The concentrate was purified by column chromatography (silica gel, developing solvent chloroform / methanol) to obtain 4.3 g (yield 34%) of a coloring material C-1 represented by the following chemical formula (8).
The obtained compound was confirmed to be the target compound from the following analysis results.
MS (ESI) (m / z): 532 (M +)
Elemental analysis value: CHN actual measurement value (78.13%, 7.94%, 7.27%); theoretical value (78.21%, 8.16%, 7.39%)
・ Fluorescent X-ray analysis: MoW actual ratio (0%, 100%); theoretical value (0%, 100)
Further, the coloring material C-1 has an absorption maximum at a wavelength of 588 nm, and the molar absorption coefficient at the maximum wavelength is 80,900 L / (mol · cm).

(3) Synthesis of Color Material C-2 Subsequently, in (3) of Synthesis Example 1 and (3) of Synthesis Example 1, except that Color material C-1 was used instead of Color material A-1 Similarly, a coloring material C-2 represented by the following chemical formula (9) was obtained (yield 96%).
It was confirmed that the obtained compound (coloring material C-2) is a target compound from the following analysis result.
31P NMR (d-dmso, ppm) δ-15.15
MS (MALDI) (m / z): 598 (M +), 2879 (M2-)
Elemental analysis values: CHN actual values (29.84%, 3.21%, 2.90%); theoretical values (29.79%, 3.11%, 2.82%)
・ Fluorescent X-ray analysis: MoW actual ratio (0%, 100%); theoretical value (0%, 100)

Synthesis Example 4 Synthesis of Color Material D-2
In the synthesis example 1 (3), instead of 9.19 g (2.7 mmol) of 12 tungstophosphoric acid n hydrates manufactured by Kanto Chemical Co., Ltd. 9.01 g of 12 tungstophosphoric acid n hydrates manufactured by Kanto Chemical In the same manner as in (3) of the above-mentioned Synthesis Example 1 except that 2.6 mmol) and 0.01 g (0.054 mmol) of 12 molybdophosphoric acid / n hydrate made by Kanto Chemical Co., Ltd. were used, Table The coloring material D-2 having a molar ratio of molybdenum to tungsten of 2.0: 98.0 was obtained (yield: 96%).
It was confirmed that the obtained compound (coloring material D-2) is a target compound from the analysis results described below.
31P NMR (d-dmso, ppm) δ-4.02, -15.15
MS (MALDI) (m / z): 584 (M +), 1824 (M2-), 2879 (M2-)
Elemental analysis value: CHN actual measurement value (32.15%, 3.40%, 2.60%); theoretical value (32.04%, 3.28%, 2.73%)
・ Fluorescent X-ray analysis: MoW actual ratio (2.0%, 97.9%); theoretical value (2.00%, 98.0)

Comparative Synthesis Example 1: Synthesis of Color Material E-2
In the same manner as in (3) of the above-mentioned Synthesis Example 1 except that, in (3) of the above Synthesis Example 1 except that Basic Blue 7 manufactured by Tokyo Kasei Co., Ltd. was used instead of the coloring material A-1, To obtain a colorant E-2 (yield 95%).
The obtained compound (coloring material E-2) was confirmed to be a target compound from the following analysis results.
31P NMR (d-dmso, ppm) δ-15.15
MS (MALDI) (m / z): 478 (M +), 2879 (MH2-)
Elemental analysis values: CHN measured values (27.65%, 2.75%, 2.86%); theoretical values (27.57%, 2.80%, 2.92%)
・ Fluorescent X-ray analysis: MoW actual ratio (0%, 100%); theoretical value (0%, 100)
Basic Blue 7 had an absorption maximum at a wavelength of 593 nm, and the molar absorption coefficient at the maximum wavelength was 70600 L / (mol · cm).

Comparative Synthesis Example 2: Synthesis of Color Material F-1 and Color Material F-2
(1) Synthesis of Intermediate F 16.2 g (168.6 mmol) of sodium t-butoxy, 11.6 g (114.6 mmol) of n-hexylamine, 0.63 g (2.40 mmol) of triphenylphosphine in 62 mL of xylene, 0.27 g (1.20 mmol) of palladium acetate was added, and it heated up to 110-115 degreeC. At the same temperature, 25.0 g (120.7 mmol) of 1-bromonaphthalene was added dropwise. After completion of the dropwise addition, reaction was carried out at the same temperature for 20 hours, water was added to the reaction solution, and the organic layer was washed. The organic layer was concentrated and purified by column chromatography (silica gel, developing solvent toluene / n-hexane) to obtain 11.0 g (yield 40%) of an intermediate F represented by the following general formula (12) .
The obtained compound was confirmed to be the target compound from the following analysis results.
MS (ESI) (m / z): 228 (M + H)

(2) Synthesis of coloring material F-1 In 25 g of chlorobenzene, 5.0 g (22.0 mmol) of the intermediate F, 9.9 g (30.5 mmol) of 4,4'-bis (diethylamino) benzophenone, and phosphorus oxychloride 4.9 g (32.0 mmol) was added and allowed to react at 40-45 ° C. for 3 hours. The reaction solution was extracted with chloroform, and the organic layer was washed with water and concentrated. The concentrate was purified by column chromatography (silica gel, developing solvent chloroform / methanol) to obtain 9.6 g (yield 77%) of a coloring material F-1 represented by the following chemical formula (13).
The obtained compound was confirmed to be the target compound from the following analysis results.
MS (ESI) (m / z): 534 (M +)
Elemental analysis values: CHN measured values (77.75%, 8.62%, 7.19%); theoretical values (77.93%, 8.48%, 7.37%)
Further, the coloring material F-1 has an absorption maximum at a wavelength of 591 nm, and the molar absorption coefficient at the maximum wavelength is 83200 L / (mol · cm).

(3) Synthesis of Color Material F-2 Subsequently, in (3) of Synthesis Example 1 and (3) of Synthesis Example 1, except that Color material F-1 was used instead of Color material A-1 Similarly, a colorant coloring material F-2 represented by the following chemical formula (14) was obtained (yield: 92%).
The obtained compound (coloring material F-2) was confirmed to be a target compound from the following analysis results.
31P NMR (d-dmso, ppm) δ-15.15
MS (MALDI) (m / z): 584 (M +), 2879 (M2-)
Elemental analysis: Measured CHN (29.78%, 3.19%, 2.91%); theoretical value (29.75%, 3.24%, 2.81%)
・ Fluorescent X-ray analysis: MoW actual ratio (0%, 100%); theoretical value (0%, 100)

Preparation Example 1: Preparation of Salt Block Polymer Dispersant A Solution
60.74 parts by mass of PGMEA and a block copolymer containing a tertiary amino group (trade name: BYK-LPN 6919, manufactured by BYK-Chemie Co., Ltd.) (amine value: 120 mg KOH / g, solid content: 60% by weight) 35.64 parts by mass (Equivalent solids: 21.38 parts by mass) are dissolved respectively, 3.62 parts by mass of PPA (0.5 molar equivalent relative to the tertiary amino group of the block copolymer) are added, and the mixture is stirred at 40 ° C. for 30 minutes Thus, a salt-type block polymer dispersant A solution (solid content 25%) was prepared.

Preparation Example 2 Preparation of Binder Composition A
(1) Synthesis of binder resin A 130 parts by mass of diethylene glycol ethyl methyl ether (abbr. EMDG) is charged as a solvent in a reactor equipped with a cooling pipe, a funnel for addition, an inlet for nitrogen, a mechanical stirrer and a digital thermometer. After raising the temperature to 90 ° C. under an atmosphere, 32 parts by mass of methyl methacrylate, 22 parts by mass of cyclohexyl methacrylate, 24 parts by mass of methacrylic acid, 2.0 parts by mass of AIBN as an initiator and n-dodecyl mercaptan 4 as a chain transfer agent A mixture containing .5 parts by weight was continuously added dropwise over 1.5 hours.
Thereafter, the reaction was continued while maintaining the synthesis temperature, and 2 parts after completion of the dropwise addition, 0.05 parts by mass of p-methoxyphenol was added as a polymerization inhibitor.
Next, 22 parts by mass of glycidyl methacrylate is added while blowing in air, and the temperature is raised to 110 ° C. 0.2 parts by mass of triethylamine is then added to cause addition reaction at 110 ° C. for 15 hours. The solid content was 44% by mass).
The obtained binder resin A had a weight average molecular weight (Mw) of 8500, a number average molecular weight (Mn) of 4200, a molecular weight distribution (Mw / Mn) of 2.02, and an acid value of 85 mg KOH / g.

(2) 19.82 parts by mass of PGMEA, 18.18 parts by mass of the binder resin A (solid content: 44% by mass), 8.00 parts by mass of 5- to 6-functional acrylate monomer (trade name: Alonix M403, manufactured by Toagosei Co., Ltd.) 2-Methyl-1 [4- (methylthio) phenyl] -2-morpholinopropan-1-one (trade name: Irgacure 907, manufactured by BASF Corp.) 3.00 parts by mass, 2,4 diethylthioxanthone (trade name: Binder composition A (solid content: 40% by mass) was prepared by mixing 1.00 parts by mass of Kayacure DETX-S (manufactured by Nippon Kayaku Co., Ltd.).

Example 1 Preparation of Colorant Dispersion A and Colored Resin Composition A
(1) 13.0 parts by mass of a color material A-2 of Synthesis Example 1 and 20.80 parts by mass of a solution of the salt type block polymer dispersant A prepared in Preparation Example 1 (effective solid content 5.20 parts by mass), 11.82 parts by mass of the binder resin A of Preparation Example 2 (effective solid content 5.20 parts by mass) and 54.38 parts by mass of PGMEA are mixed and 1 hour with 2 mm zirconia beads as preliminary dispersion with a paint shaker (manufactured by Asada Iron Works) Further, as main dispersion, dispersion was carried out with 0.1 mm zirconia beads for 6 hours to obtain a colorant dispersion liquid A.
(2) 28.57 parts by mass of the color material dispersion A obtained in the above (1), 28.29 parts by mass of the binder composition A obtained in Preparation Example 2, 43.14 parts by mass of PGMEA, surfactant R08 MH A colored resin composition A was obtained by adding and mixing 0.04 parts by mass (manufactured by DIC) and 0.4 parts by mass of a silane coupling agent KBM 503 (manufactured by Shin-Etsu Silicone Co., Ltd.), and performing pressure filtration.

(Examples 2 to 4: Preparation of Colorant Dispersions B to D, and Colored Resin Compositions B to D)
Color material dispersion liquids B to D and colored resin compositions B to D in the same manner as in Example 1 except that color materials B-2 to D-2 were used instead of color material A-2 in example 1. I got D.

Comparative Examples 1 to 2 Preparation of Colorant Dispersions E to F, and Colored Resin Compositions E to F
Color material dispersions E to F and colored resin compositions E to F in the same manner as in Example 1 except that color materials E-2 to F-2 were used instead of color material A in Example 1. Obtained.

[Evaluation]
<Optical performance evaluation, heat resistance evaluation>
The colored resin composition obtained in each Example and Comparative Example was coated on a glass substrate ("OA-10G" manufactured by Nippon Electric Glass Co., Ltd.) having a thickness of 0.7 mm using a spin coater. Then, it heat-dried on the 80 degreeC hotplate for 3 minutes. The cured film (blue colored layer) was obtained by irradiating an ultraviolet-ray of 40 mJ / cm < ² > using a super-high pressure mercury lamp. The film thickness after drying and curing is set to the target chromaticity y = 0.082, and the chromaticity (x, y), luminance (Y), L, a, b (L ₀ , a ₀ ) of the obtained colored substrate are obtained. , B ₀ ) were measured using “Microspectroscopic light measuring apparatus OSP-SP200” manufactured by Olympus Corporation. The substrate on which the colored film is formed is post-baked for 30 minutes in a clean oven at 230 ° C., and the chromaticity (x, y), luminance (Y), L, a, b (L ₁ ) of the obtained colored film are obtained. , A ₁ , b ₁ ) were measured. From the measured values, the chromaticity (x) after heating, the value of luminance (Y), and the color difference (ΔEab) before and after heating at 230 ° C. were calculated. Table 1 shows the results.

<Evaluation: Contrast>
The colored resin compositions obtained in the respective Examples and Comparative Examples were respectively spin coated on a glass substrate and dried on a hot plate at 80 ° C. for 3 minutes.
This substrate was exposed with a gap of 150 μm in air using a U-BO Co., Ltd. UI-501C ultra-high pressure mercury lamp. The exposure dose was 50 mJ / cm ^{2 as} measured with an integrated actinometer UIT-102 manufactured by Ushio Inc. and a light receiver UVD-365 PD. The obtained coating film was left to stand at 230 ° C. for 30 minutes, and the contrast value of the produced glass substrate was measured using “Contrast measuring device CT-1B” manufactured by Takasaka Electric Co., Ltd. The larger the contrast value, the smaller the degree of light scattering, and the smaller the leaked light when used as a color filter of a liquid crystal display device, making it possible to make the liquid crystal panel bright and dark. In order to increase the contrast, it is required that the coating film be uniform. In the case of a nonuniform coating film in which precipitation of crystals, phase separation and the like occur, the contrast value becomes small. The measurement results are shown in Table 1.

[Result Summary]
As shown in Table 1, the colored layer obtained using the colored resin composition containing the coloring materials A-2 to D-2, which is the coloring material represented by the general formula (I), is after post-baking It was revealed that the color difference of was small and the luminance and the contrast were excellent. This is due to the salt formation of a cation having a triarylmethane skeleton having an alicyclic hydrocarbon group having 6 or more carbon atoms and a polyacid anion in the aggregate of the coloring material represented by the general formula (I). The stacking of the triarylmethane skeleton is unlikely to occur, and the alicyclic hydrocarbon group introduced as a substituent in the triarylmethane skeleton, which is disposed at a certain distance, is in a space in the aggregate of the coloring material. It is considered that the heat resistance is improved as a result of the space in the colorant aggregate being reduced and the density being increased because the particles are uniformly disposed and fixed. Among them, it is apparent that Examples 1, 2 and 4 containing Colorant A-2, B-2 or D-2 having an adamantyl group are further excellent in heat resistance as compared with Example 3. became. This is because the melting point of adamantane corresponding to the adamantyl group is as high as 270 ° C., which is higher than the melting point 6 to 7 ° C. of cyclohexane, so that it is stable in the coloring material even at high temperature heating. It is estimated that it contributes. On the other hand, Comparative Examples 1 and 2 containing a coloring material containing an ethyl group or a hexyl group as a chain hydrocarbon group had low heat resistance. Since the melting point of the chain-increasing hydrocarbon corresponding to the chain-like hydrocarbon group is low, the chain-like hydrocarbon group has high activity of movement due to heat, and can not be stably present in the space in the colorant aggregate, It is thought that the sex improvement effect was low. Further, since the melting point is lower in hexane (melting point-95 ° C) corresponding to hexyl group than ethane (melting point-89 ° C) corresponding to ethyl group, Comparative Example 2 is more heat resistant than Comparative Example 1 It is considered that the result was low. It is considered that the decrease in the melting point due to the extension of the alkyl chain length led to the destabilization of the compound. In addition, as a result of the color material deteriorating due to heat, the apparent contrast value of Comparative Example 2 is high.

DESCRIPTION OF SYMBOLS 1 transparent substrate 2 light-shielding part 3 colored layer 10 color filter 21 transparent electrode film 22 electrode substrate 23 transparent substrate 25 liquid crystal layer 30 counter substrate 40 liquid crystal display device 50 organic protective layer 60 inorganic oxide film 71 transparent anode 72 hole injection layer 73 positive Hole transport layer 74 Light emitting layer 75 Electron injection layer 76 Cathode 80 Light emitter 100 Organic light emitting display

Claims (8)

A color containing (A) a coloring material, (B) a dispersant, and (C) a solvent, and the (A) coloring material containing a coloring material (1) represented by the following general formula (I) Material dispersion.
(In general formula (I), Ar represents a divalent aromatic group which may have a substituent, R ^{1 to} R ⁶ each independently represent a hydrogen atom, an aromatic hydrocarbon group as a substituent, a halogen An aliphatic hydrocarbon group which may have at least one of an atom and a hydroxyl group, or an aromatic hydrocarbon which may have at least one of a halogen atom and an aliphatic hydrocarbon group as a substituent R ¹ and R ² , R ³ and R ⁴ , and R ⁵ and R ⁶ may combine to form a ring structure, provided that at least one of R ^{1 to} R ⁶ is carbon It contains an alicyclic hydrocarbon group having 6 or more atoms.
a represents a number of 2 or more, X ^a- is table to a value of the inorganic anion, the inorganic anion is one or more selected from oxo inorganic acids and the group consisting of the dehydrated condensate.
When there are a plurality of R ^{1 to} R ⁶ and Ar, the plurality of R ^{1 to} R ⁶ and Ar may be the same or different. )   The melting point of the alicyclic hydrocarbon corresponding to the alicyclic hydrocarbon group having 6 or more carbon atoms which the coloring material (1) represented by the general formula (I) has is 80 to 300 ° C. The colorant dispersion according to claim 1. The colorant dispersion according to claim 1 or 2, wherein ^Xa- in the general formula (I) is an a-valent polyacid containing one or more atoms selected from tungsten and molybdenum. The colorant according to claim 3 , wherein the polyacid contained in the colorant (1) represented by the general formula (I) contains at least tungsten, and the molar ratio of molybdenum to tungsten is 2/98 or less. Dispersion. A colorant containing (A) a colorant, (B) a dispersant, (C) a solvent, and (D) a binder component, wherein the (A) colorant is represented by the following general formula (I) Colored resin composition for color filters containing (1).
(In general formula (I), Ar represents a divalent aromatic group which may have a substituent, R ^{1 to} R ⁶ each independently represent a hydrogen atom, an aromatic hydrocarbon group as a substituent, a halogen An aliphatic hydrocarbon group which may have at least one of an atom and a hydroxyl group, or an aromatic hydrocarbon which may have at least one of a halogen atom and an aliphatic hydrocarbon group as a substituent R ¹ and R ² , R ³ and R ⁴ , and R ⁵ and R ⁶ may combine to form a ring structure, provided that at least one of R ^{1 to} R ⁶ is carbon It contains an alicyclic hydrocarbon group having 6 or more atoms.
a represents a number of 2 or more, X ^a- is table to a value of the inorganic anion, the inorganic anion is one or more selected from oxo inorganic acids and the group consisting of the dehydrated condensate.
When there are a plurality of R ^{1 to} R ⁶ and Ar, the plurality of R ^{1 to} R ⁶ and Ar may be the same or different. ) A color filter comprising at least a transparent substrate and a colored layer provided on the transparent substrate, wherein at least one of the colored layers comprises a coloring material (1) represented by the following general formula (I): Color filter.
(In general formula (I), Ar represents a divalent aromatic group which may have a substituent, R ^{1 to} R ⁶ each independently represent a hydrogen atom, an aromatic hydrocarbon group as a substituent, a halogen An aliphatic hydrocarbon group which may have at least one of an atom and a hydroxyl group, or an aromatic hydrocarbon which may have at least one of a halogen atom and an aliphatic hydrocarbon group as a substituent R ¹ and R ² , R ³ and R ⁴ , and R ⁵ and R ⁶ may combine to form a ring structure, provided that at least one of R ^{1 to} R ⁶ is carbon It contains an alicyclic hydrocarbon group having 6 or more atoms.
a represents a number of 2 or more, X ^a- is table to a value of the inorganic anion, the inorganic anion is one or more selected from oxo inorganic acids and the group consisting of the dehydrated condensate.
When there are a plurality of R ^{1 to} R ⁶ and Ar, the plurality of R ^{1 to} R ⁶ and Ar may be the same or different. )   A liquid crystal display device comprising the color filter according to claim 6, a liquid crystal layer, and a counter substrate.   A light emitting display device comprising the color filter according to claim 6 and a light emitter.