TWI559035B - Colorant, coloring composition, color filter and display element - Google Patents

Description

Colorant, coloring composition, color filter, and display element

The present invention relates to a coloring composition, a color filter, and a display element, and more particularly to color filter applied to a transmissive or reflective type color liquid crystal display element, solid-state imaging element, organic EL display element, electronic paper, or the like. The coloring agent of the sheet contains a coloring composition of the coloring agent, a color filter including a coloring layer of the coloring agent, and a display element including the color filter.

When a color filter is produced using a coloring sensitizing radiation composition, a method is known in which a pigment dispersion type color sensitizing radiation composition is applied onto a substrate and dried, and then the dried coating film is irradiated in a desired pattern shape. Radiation (hereinafter referred to as "exposure") and development are performed to obtain pixels of respective colors (Patent Documents 1 to 2). Further, a method of forming a black matrix by using a photopolymerizable composition in which carbon black is dispersed is also known (Patent Document 3). Further, a method of obtaining pixels of respective colors by an inkjet method using a pigment-dispersed colored resin composition is known (Patent Document 4).

However, it is known that it is effective to achieve high luminance and high color purity of a display element or high definition of a solid-state imaging element. Dyes are used as colorants. For example, Patent Document 5 proposes the use of a triarylmethane-based dye having a specific structure.

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open No. 2-144502

[Patent Document 2] Japanese Patent Laid-Open No. 3-53201

[Patent Document 3] Japanese Patent Laid-Open No. Hei 6-35188

[Patent Document 4] Japanese Patent Laid-Open Publication No. 2000-310706

[Patent Document 5] Japanese Patent Laid-Open Publication No. 2008-304766

However, the triarylmethane dye proposed in Patent Document 5 is insufficient in heat resistance if it is exposed to an image exceeding 200 ° C. The heating (post-baking) step after development loses the superiority to the chromaticity characteristics of the pigment. Further, if a dye is used, the problem that the voltage holding ratio of the color filter is deteriorated is repeated. In light of the above background, there is an urgent need to develop a coloring composition suitable for producing a color filter which can achieve both high heat resistance and good voltage holding ratio.

Therefore, an object of the present invention is to provide a coloring composition suitable for forming a coloring layer which can achieve both high heat resistance and good voltage holding ratio. Further, an object of the present invention is to provide a color filter including a coloring layer formed of the coloring composition, and a display element including the color filter.

In view of the above, the present inventors have conducted intensive studies and found that the above problem can be solved by using a conjugate base having an organic acid having a strong acidity as an anion portion and the anion having a polymerizable unsaturated group.

That is, the present invention provides a coloring composition comprising: (A) a coloring agent comprising a compound represented by the following formula (1), (B) a binder resin, and (C) a crosslinking agent.

X ⁺ Z ^- (1)

[In the formula (1), X ⁺ represents a cationic chromophore; and Z ^- represents a conjugate base of an organic acid having a polymerizable unsaturated group and a halogen group. ]

Moreover, the present invention provides a color filter including a coloring layer containing the compound represented by the above formula (1), and a display element including the color filter. Here, the "colored layer" refers to each color pixel, black matrix, black spacer, or the like used for the color filter.

The present invention also provides a coloring agent represented by the above formula (1).

When the colored composition of the present invention is used, a coloring layer having both high heat resistance and a good voltage holding ratio can be formed. Therefore, the coloring composition of the present invention is extremely suitable for use in the production of color filters for display elements, color filters for color separation elements, color filters for organic EL display elements, and color filters for electronic paper. A variety of color filters represented by the film.

[Formation of the Invention]

Hereinafter, the present invention will be described in detail.

Coloring composition

Hereinafter, the constituent components of the colored composition of the present invention will be described in detail.

- (A) colorant -

The coloring composition of the present invention contains (A) a coloring agent containing a compound represented by the following formula (1) (hereinafter also referred to as "the present coloring agent").

X ⁺ Z ^- (1)

[In the formula (1), X ⁺ represents a cationic chromophore; and Z ^- represents a conjugate base of an organic acid having a polymerizable unsaturated group and a halogen group.

First, the formula (1) Z ^- is described.

Z ^- is not particularly limited as long as it is a conjugate base of an organic acid having a polymerizable unsaturated group and a halogen group. Examples of the acid include a carboxylic acid (-CO ₂ H), a sulfonic acid (-SO ₃ H), a ruthenium imidate (-CONHCO-), a sulfoximine acid (-SO ₂ NHSO ₂ -), and a carbonyl group. Aminosulfonic acid (-CONHSO ₂ -) and the like. In the present invention, from the viewpoint of forming a conjugate base of an organic acid having a stronger acidity, among the above acids, sulfonimide (-SO ₂ NHSO ₂ -) or carbonylaminosulfonic acid (- CONHSO ₂ -).

Preferred examples of Z ^- in the present invention include an anion represented by the following formula (1a-1).

In the formula (1a-1), Y ¹ represents a group having a polymerizable unsaturated group; Y ² represents a halogen group or a halogenated hydrocarbon group which may have a linking group containing a carbon atom, a hydrogen atom or an atom other than a halogen atom. ]

Y ¹ is not particularly limited as long as it has a polymerizable unsaturated group, but is preferably an organic group having a polymerizable unsaturated group. The above-mentioned organic group may, for example, be a chain organic group or a cyclic organic group, and is preferably a chain organic group. Incidentally, the bonding position and the number of bonding of the polymerizable unsaturated group to these organic groups are arbitrary. Further, when the organic group has a substituent other than the polymerizable unsaturated group, the kind, the bonding position, and the number of bonds are not limited. Examples of the polymerizable unsaturated group include a (meth)acrylonitrile group, a vinyl group, and an allyl group. The present inventors have estimated that, in the present invention, by having a polymerizable unsaturated group, the polymerizable unsaturated group undergoes a crosslinking reaction during exposure or post-baking, thereby suppressing elution of the dye into the liquid crystal. Can show good voltage retention.

Further, as a particularly preferable Z-, an anion represented by the following formula (1a-2) and formula (1a-3) can be given.

[In the formula (1a-2), R ¹ represents a (meth)acryloyl group or an allyl group; and X ¹ represents -O- or -O-(R ² O) _q -(*) (wherein R ² represents An alkanediyl group having 2 or 3 carbon atoms, q represents an integer of 1 to 100, (*) represents a bond to X ² ); X ² represents a substituted or unsubstituted alkanediyl group; Y ² and formula (1a- The Y ^{2 in} 1) is synonymous. ]

[In the formula ^(1a-3), R 3 represents a hydrogen atom or a methyl group; X ³ represents a single bond or a substituted or unsubstituted alkoxy diyl; ² synonymous with the formula Y ² Y (1a-1) of. ]

R ¹ represents a (meth) acrylonitrile group or an allyl group, but from the viewpoint of easiness of the crosslinking reaction, a (meth) acrylonitrile group is more preferably used.

R ^{2 of} X ¹ represents an alkanediyl group having 2 or 3 carbon atoms. Specifically, ethyl, ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane- The 2,2-diyl group is more preferably an ethyl group or a propane-1,2-diyl group from the viewpoint of ease of production.

The q of X ¹ is an integer of 1 to 100, preferably 1 to 30, more preferably 1 to 10, and particularly preferably 1 to 5.

The alkanediyl group of X ² is preferably an alkanediyl group having 1 to 10 carbon atoms. Specifically, a methylene group, an ethylidene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, and a propane-1,3-di group are mentioned. Base, propane-2,2-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, pentane-1,4-diyl Pentane-1,5-diyl, hexane-1,5-diyl, hexane-1,6-diyl, octane-1,8-diyl, decane-1,10-diyl Among them, an alkanediyl group having 2 to 8 carbon atoms is preferred, and an alkanediyl group having 2 to 6 carbon atoms is more preferred.

The alkanediyl group in X ³ is preferably an alkanediyl group having 1 to 10 carbon atoms. Specifically, the same groups as described above are preferable, and among them, an alkanediyl group having 1 to 8 carbon atoms is preferable, and an alkanediyl group having 2 to 6 carbon atoms is more preferable.

A representative example of Y ¹ in the above formula (1a-1) is, for example, a group represented by the following formula. It should be noted that "*" indicates a connection key to N-.

Next, Y ² of the formula (1a-1), the formula (1a-2), and the formula (1a-3) will be described. Y ² represents a halogen group or a halogenated hydrocarbon group which may have a linking group containing a carbon atom, a hydrogen atom or an atom other than a halogen atom. Examples of the halogen group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the hydrocarbon group which forms the skeleton of the above-mentioned halogenated hydrocarbon group include (1) an aliphatic hydrocarbon group, (2) an alicyclic hydrocarbon group, and (3) an aliphatic hydrocarbon group having an alicyclic hydrocarbon group as a substituent (hereinafter referred to as " An alicyclic hydrocarbon-substituted aliphatic hydrocarbon group"), (4) an aromatic hydrocarbon group, and (5) an aromatic hydrocarbon group having an aliphatic hydrocarbon group as a substituent (hereinafter referred to as "aliphatic hydrocarbon-substituted aromatic hydrocarbon group"), (6) An aliphatic hydrocarbon group having an aromatic hydrocarbon group as a substituent (hereinafter referred to as "aromatic hydrocarbon-substituted aliphatic hydrocarbon group") or the like. The hydrocarbon group which forms the skeleton of the above-mentioned halogenated hydrocarbon group is preferably the following characteristic group from the viewpoint of solubility in an organic solvent.

That is, the (1) aliphatic hydrocarbon group is preferably an alkyl group, and the alkyl group may be linear or branched. The number of carbon atoms of the alkyl group is preferably from 1 to 20, particularly preferably from 1 to 8. Further, the (2) alicyclic hydrocarbon group is preferably an alicyclic saturated hydrocarbon group, and the number of carbon atoms thereof is preferably from 3 to 20, particularly preferably from 3 to 12. Further, the (3) alicyclic hydrocarbon-substituted aliphatic hydrocarbon group is preferably an alicyclic saturated hydrocarbon-substituted alkyl group, and the total number of carbon atoms thereof is preferably 4 to 20, particularly preferably 6 to 14. Further, the (4) aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 14 carbon atoms (more preferably 6 to 10 carbon atoms), and particularly preferably a phenyl group. Further, the (5) aliphatic hydrocarbon-substituted aromatic hydrocarbon group is preferably an alkyl-substituted phenyl group, and the total number of carbon atoms thereof is preferably from 7 to 30, particularly preferably from 7 to 20. Further, the (6) aromatic hydrocarbon-substituted aliphatic hydrocarbon group is preferably an aralkyl group, and the total number of carbon atoms thereof is preferably from 7 to 30, particularly preferably from 7 to 20. Incidentally, the alkyl group in the present specification may be linear or branched.

Among them, as the hydrocarbon group forming the skeleton of the above halogenated hydrocarbon group, (1) an aliphatic hydrocarbon group, (3) an alicyclic hydrocarbon-substituted aliphatic hydrocarbon group, (4) an aromatic hydrocarbon group, and (5) an aliphatic hydrocarbon-substituted aromatic group are preferable. Hydrocarbyl or (6) aromatic hydrocarbon substituted aliphatic hydrocarbon group, more preferably alkyl or alicyclic saturated hydrocarbon Alkenyl, phenyl, alkyl substituted phenyl, aralkyl, particularly preferably alkyl.

Further, the halogen group in the Y ² and the halogen in the halogenated hydrocarbon group are preferably fluorine atoms from the viewpoint of heat resistance of the colorant. It is considered that by selecting a fluorine atom as a substituent, the anion portion of the coloring agent can be made into a conjugate base of an organic acid having a stronger acidity. Therefore, a salt having a stronger ion-bonding force can be formed, and heat resistance can be improved.

Further, in Y ² , examples of the linking group containing a carbon atom, a hydrogen atom, and an atom other than a halogen atom include -O-, -S-, -CO-, -COO-, -CONH-, and -SO _{2 .} -Wait. Further, the number of carbon atoms referred to in the first paragraph on page 11 of the specification means the total number of carbon atoms of a portion other than the carbon atom constituting the linking group.

In the present invention, from the viewpoint of heat resistance of the colorant, Y ^{2 is} preferably a group represented by the following formula (1-1) or (1-2), and particularly preferably an organic acid having a higher acidity. The group of the conjugate base represented by the following formula (1-1).

[In the formula (1-1), R ²³ represents a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, an alicyclic hydrocarbon group, an alkoxy group, a fluorinated alkoxy group, R ²⁴ COOR ²⁵ - or R ²⁴ COOR. ²⁵ CFH-(R ²⁴ represents an alkyl group, an alicyclic hydrocarbon group, a heteroaryl group or a substituted or unsubstituted aryl group, and R ²⁵ represents an alkanediyl group); n represents an integer of 0 or more; "*" represents a linkage. ]

[In the formula (1-2), R ¹⁸ to R ²² each independently represent a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group, a fluorinated alkyl group or an alkoxy group; "*" represents a linkage; wherein, R ¹⁸ ~ At least one of II ²² is a fluorine atom or a fluorinated alkyl group. ]

In the formula (1-1), R ^{23 is} preferably a fluorine atom, a fluorinated alkyl group, an alicyclic hydrocarbon group, a fluorinated alkoxy group, R ²⁴ COOR ²⁵ - or R ²⁴ COOR ²⁵ CFH-, particularly preferably Fluorine atom, alicyclic hydrocarbon group, perfluoroalkoxy group, R ²⁴ COOCH ₂ CH ₂ - or R ²⁴ COOCH ₂ CH ₂ CFH-.

R ²⁴ represents an alkyl group, an alicyclic hydrocarbon group, a heteroaryl group or a substituted or unsubstituted aryl group, and the alkyl group may be linear or branched, and preferably the alkyl group has 1 to 12 carbon atoms. (More preferably 1~8). The alicyclic hydrocarbon group may be a 2 to 4 ring bridged alicyclic hydrocarbon group, and preferably the alicyclic hydrocarbon group has 3 to 20 carbon atoms (more preferably 3 to 12). The heteroaryl group is preferably composed of a 5- to 10-membered aromatic heterocyclic ring containing at least one hetero atom selected from a nitrogen atom, an oxygen atom and a sulfur atom. The aryl group is preferably an aryl group having 6 to 14 carbon atoms (more preferably 6 to 10 carbon atoms), and particularly preferably a phenyl group. In addition, examples of the substituent include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a halogen atom or a trifluoromethyl group, and the position and number of substituents. When it has any two or more substituents, the substituent may be the same or different.

Further, R ²⁵ represents an alkanediyl group, preferably an alkanediyl group having 1 to 6 carbon atoms, and particularly preferably an ethylidene group from the viewpoint of easiness of production.

Incidentally, the upper limit of n is preferably 10, more preferably 8.

Further, in the formula (1-2), at least three of R ¹⁸ to R ²² are preferably a fluorine atom or a fluorinated alkyl group.

Specific examples of Y ² represented by the above formula (1a-1), formula (1a-2), and formula (1a-3) include a group represented by the following formula. Incidentally, the "*" represents a direct bond with the SO _2.

Next, X ⁺ in the formula (1) will be described.

As long as X ⁺ is a cationic chromophores, i.e. X ⁺ Z ^- is formed of alkaline cations colorant is not particularly limited, and examples thereof include triarylmethane-based chromophores, methine chromophore, An azo chromophore, a diarylmethane chromophore, a quinone imine chromophore, a chromophore, an indigo chromophore, A chromophore, etc.

The triarylmethane chromophore is preferably a compound represented by the following formula (2). In the cations represented by the following formula (2), various resonance structures exist, but in the present specification, these resonance structures are regarded as equivalent to the cations represented by the following formula (2).

[In the formula (2), Ar represents a substituted or unsubstituted aromatic hydrocarbon group; and R ⁴ to R ⁷ independently of each other represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a cycloalkyl group having 3 to 8 carbon atoms; Or a phenyl group or a group having an ethylenically unsaturated bond; R ⁸ to R ¹⁵ represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or -COOR'(R' represents a hydrogen atom or an alkane having 1 to 8 carbon atoms; Or a halogen group; Y ³ represents a hydrogen atom or a group represented by the following formula (3). ]

[In the formula (3), R ¹⁶ and R ¹⁷ independently of each other represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group or an ethylenically unsaturated bond. base. ]

The aromatic hydrocarbon group in Ar is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms (more preferably 6 to 10 carbon atoms), and specific examples thereof include a stretching phenyl group, an anthranyl group, and a stretching group. Phenyl, thiol and the like. The substituent is, for example, an alkyl group having 1 to 6 carbon atoms, and the position and number of the substituent are arbitrary. When two or more substituents are present, the substituents may be the same or different.

Examples of the alkyl group having 1 to 8 carbon atoms in R ⁴ to R ¹⁷ (including R' of -COOR' in R ⁸ to R ¹⁷ ) include a methyl group, an ethyl group, a propyl group, and an isopropyl group. , butyl, secondary butyl, tert-butyl, isobutyl, pentyl, tertiary pentyl, hexyl, heptyl, octyl, isooctyl, trioctyl, 2-ethylhexyl and the like.

In the present invention, the cation represented by the above formula (2) is particularly preferably a cation represented by the following formula (4) from the viewpoint of improving brightness and color purity.

[In the formula (4), R ⁴ to R ⁷ and R ¹⁶ to R ^{17 have the} same meanings as R ⁴ to R ⁷ and R ¹⁶ to R ¹⁷ in the above formulas (2) and (3). ]

In the above formula (4), R ⁴ , R ⁵ , R ¹⁶ and R ^{17 are} preferably an alkyl group having 1 to 8 carbon atoms (more preferably 1 to 6 carbon atoms), and further preferably R ⁶ . Preferably, it is an alkyl group or a phenyl group having 1 to 8 carbon atoms (more preferably 1 to 6 carbon atoms), and further preferably R ^{7 is} preferably 1 to 8 carbon atoms (more preferably 1 to 6 carbon atoms). 6) an alkyl or hydrogen atom.

A representative example of the cation represented by the above formula (2) is, for example, a cation represented by the following formula.

The methine chromophore is preferably a compound represented by the following formulas (5-1) to (5-3).

In the formulae (5-1) to (5-3), R ³¹ represents a hydrogen atom or a halogen atom; and R ³² , R ³³ , R ³⁴ and R ³⁵ each independently represent an alkyl group having 1 to 6 carbon atoms; ³⁶ represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; G represents -CH=CH-, -CH=CH-NR ³⁷ - (R ³⁷ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms) , -CH=N-NR ³⁷ - (R ³⁷ is synonymous with the above) or -N=N-NR ³⁷ - (R ³⁷ is synonymous with the above); R ^a represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted Heterocyclic group.]

R ^{a is} preferably a group represented by the following formulas (5a) to (5g).

[In the formulae (5a) to (5g), R ³⁸ and R ⁴⁵ each independently represent an alkyl group having 1 to 6 carbon atoms; and R ³⁹ represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; R ⁴⁰ R ⁴² , R ⁴³ and R ⁴⁴ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and R ⁴¹ and R ⁴⁶ independently represent a hydrogen atom, a halogen atom or an alkoxy group having 1 to 6 carbon atoms; A substituted, unsubstituted alkyl group having 1 to 6 carbon atoms, a nitro group, a hydroxyl group or a cyano group. ]

Examples of the substituent of the alkyl group include a halogen atom, a cyano group, and a hydroxyl group.

Representative examples of the cation represented by the above formulas (5-1) to (5-3) include a cation represented by the following formula.

The azo-based chromophore is preferably a compound represented by the following formulas (6-1) to (6-6).

[In the formulae (6-1) to (6-6), R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , R ⁵⁵ and R ⁵⁷ each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; R ⁵⁶ and R ⁶⁰ independently of each other represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a hydroxyl group or a cyano group; and R ⁵⁸ represents a carbon atom; An alkyl group of 1 to 6; R ⁵⁹ represents a group forming a quaternary ammonium; and R ^b represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group. ]

R ^{59 is} preferably -NR ⁶¹ C _m H _2m N ⁺ R ⁶² R ⁶³ R ⁶⁴ (m is an integer of 1 to 5, and R ⁶¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ⁶² , R ⁶³ and R ⁶⁴ each independently represent an alkyl group having 1 to 6 carbon atoms), -COC _m H _2m N ⁺ R ⁶² R ⁶³ R ⁶⁴ (m, R ⁶² , R ⁶³ and R ^{64 are} synonymous with the above), -C _m H _2m N ⁺ (NH ₂ )R ⁷⁴ R ⁷⁵ (m is synonymous with the above, R ⁷⁴ and R ⁷⁵ independently of each other represent an alkyl group having 1 to 6 carbon atoms), or the following formula (6-i) Or the base represented by (6-ii).

[In the formula [(6-i) and (6-ii), R ⁶¹ and m are synonymous with the above. ]

The above R ^{b is} preferably a group represented by the following formulas (6a) to (6e), a substituted or unsubstituted phenyl group.

[In the formulae (6a) to (6d), R ⁶⁵ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group or a benzyl group; and R ⁶⁶ represents a hydrogen atom or a substituted or unsubstituted carbon atom number 1 to 6 Alkyl; R ⁶⁷ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group; R ⁶⁸ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and R ⁶⁹ represents a hydrogen atom or a carbon atom number 1~ The alkyl group of 6; R ⁷⁰ to R ⁷³ independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a hydroxyl group or a cyano group. ]

The substituent of the alkyl group may, for example, be a halogen atom, a hydroxyl group, a cyano group or a -CONH ₂ group. Examples of the substituent of the phenyl group include a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxyl group, a cyano group, and a nitro group.

Representative examples of the cation represented by the above formulas (6-1) to (6-6) include a cation represented by the following formula.

The diarylmethane chromophore is preferably a compound represented by the following formula (7-1) or (7-2).

[In the formulae (7-1) and (7-2), R ⁸¹ , R ⁸² , R ⁸³ , R ⁸⁴ , R ⁸⁶ , R ⁸⁷ , R ⁸⁸ and R ⁸⁹ each independently represent an alkane having 1 to 6 carbon atoms. The group R ⁸⁵ , R ⁹⁰ and R ⁹¹ independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ]

Representative examples of the cation represented by the above formulas (7-1) to (7-2) include a cation represented by the following formula.

The quinone imine chromophore is preferably a compound represented by the following formulas (8-1) to (8-3).

[In the formulae (8-1) to (8-3), R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁸ , R ¹⁰⁹ , R ¹¹⁰ , R ¹¹¹ , R ¹¹⁴ , R ¹¹⁵ And R ¹¹⁶ , R ¹¹⁷ and R ¹¹⁸ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group or a benzyl group; R ¹⁰⁷ And R ¹¹³ independently of each other represent an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms; and R ¹¹² represents -NR ¹¹⁹ R ¹²⁰ (R ¹¹⁹ and R ¹²⁰ independently of each other represent substituted or unsubstituted An alkyl group having 1 to 6 carbon atoms, a hydroxyl group, a nitro group or a cyano group; and Q represents an oxygen atom or a sulfur atom. ]

Examples of the substituent of the alkyl group include a halogen atom, a hydroxyl group, and a cyano group.

Representative examples of the cation represented by the above formulas (8-1) to (8-3) include, for example, a cation represented by the following formula.

The oxime chromophore is preferably a compound represented by the following formula (9-1) or (9-2).

[In the formulae (9-1) and (9-2), R ¹³¹ , R ¹³⁵ and R ¹³⁶ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted group. Phenyl group; R ¹³² , R ¹³³ , R ¹³⁴ , R ¹³⁸ , R ¹³⁹ and R ¹⁴⁰ each independently represent an alkyl group having 1 to 6 carbon atoms; R ¹³⁷ represents a methylene group or a substituted or unsubstituted carbon atom; 2 to 20 alkanediyl groups. ]

Examples of the substituent of the alkyl group or the phenyl group include an alkyl group having 1 to 6 carbon atoms, a halogen atom, a hydroxyl group, and a cyano group. Further, examples of the substituent of the alkanediyl group having 2 to 20 carbon atoms include a hydroxyl group, a cyano group, and a nitro group.

Representative examples of the cation represented by the above formula (9-1) or (9-2) include a cation represented by the following formula.

The phthalocyanine chromophore is preferably a compound represented by the following formula (10).

CuPc-T (10)

[In the formula (10), CuPc represents a copper indigo residue; and T represents a group represented by the following formula (10a) or (10b). ]

[In the formulae (10a) and (10b), R ¹⁵¹ , R ¹⁵² , R ¹⁵³ , R ¹⁵⁴ , R ¹⁵⁵ , R ¹⁵⁶ , R ¹⁵⁷ and R ¹⁵⁸ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Or phenyl; p independently of each other represents an integer from 2 to 8; m is synonymous with the above. ]

A representative example of the cation represented by the above formula (10) is, for example, a cation represented by the following formula.

As The chromophore is preferably an object represented by the following formula (11).

[In the formula (11), R ¹⁷¹ , R ¹⁷² , R ¹⁷³ and R ¹⁷⁴ each independently represent a hydrogen atom, -R ¹⁷⁸ or an aromatic hydrocarbon group having 6 to 10 carbon atoms (wherein the hydrogen contained in the aromatic hydrocarbon group) The atom may be through a halogen atom, -R ¹⁷⁸ , -OH, -OR ¹⁷⁸ , -SO ₃ H, -SO ₃ M, -CO ₂ H, -CO ₂ R ¹⁷⁸ , -SO ₃ R ¹⁷⁸ , -SO ₂ NHR ¹⁷⁹ or -SO ₂ NR ¹⁷⁹ R ¹⁸⁰ substituted); R ¹⁷⁵ and R ¹⁷⁶ independently of each other represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; and R ¹⁷⁷ represents -SO ₃ H, -SO ₃ M, -CO ₂ H, -CO ₂ R ¹⁷⁸ , -SO ₃ R ¹⁷⁸ , -SO ₂ NHR ¹⁷⁹ or -SO ₂ NR ¹⁷⁹ R ¹⁸⁰ ; r represents an integer of 0 to 5, and when r is an integer of 2 or more, a plurality of R ¹⁷⁷ may be the same or R ¹⁷⁸ represents a saturated hydrocarbon group having 1 to 10 carbon atoms (wherein the hydrogen atom contained in the saturated hydrocarbon group may be substituted by a halogen atom, and the methylene group contained in the saturated hydrocarbon group may be via an oxygen atom, a carbonyl group or -NR ¹⁷⁸⁾ -substituted); R ¹⁷⁹ and R ¹⁸⁰ independently of each other represent a chain alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms or -Z, or R ¹⁷⁹ and R ¹⁸⁰ are bonded to each other. a substituted or unsubstituted heterocyclic group having 1 to 10 carbon atoms formed Wherein the hydrogen atom contained in the alkyl group and the cycloalkyl group may be substituted by a hydroxyl group, a halogen atom, -Z, -CH=CH ₂ or -CH=CHR ¹⁷⁸ , and the methylene group contained in the alkyl group and the cycloalkyl group The group may be substituted by an oxygen atom, a carbonyl group or -NR ¹⁷⁸ -, and the hydrogen atom contained in the heterocyclic group may be substituted by -R ¹⁷⁸ , -OH or -Z; M represents a sodium atom or a potassium atom; Z represents a carbon atom number of 6 An aromatic hydrocarbon group of ~10 or an aromatic heterocyclic group having 5 to 10 carbon atoms. Here, the hydrogen atom contained in the aromatic hydrocarbon group and the aromatic heterocyclic group may be substituted with -OH, R ¹⁷⁸ , -OR ¹⁷⁸ , -NO ₂ , -CH=CH ₂ , -CH=CHR ¹⁷⁸ or a halogen atom. ]

The saturated hydrocarbon group in R ¹⁷⁸ may have a linear structure, a branched chain shape, or a cyclic shape as long as the number of carbon atoms is 1 to 10, and may have a bridging structure. Specifically, in addition to the alkyl group similar to R ⁴ in the above formula (2), a mercapto group, a fluorenyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a tricyclodecyl group may be mentioned. . The group in which the methylene group contained in the saturated hydrocarbon group is substituted with an oxygen atom may, for example, be a methoxypropyl group, an ethoxypropyl group, a 2-ethylhexyloxypropyl group or a methoxyhexyl group.

^Examples of the substituted or unsubstituted heterocyclic group having 1 to 10 carbon atoms formed by bonding R ¹⁷⁹ and R ^{180 to} each other include pyrrole, pyridine, indole, isoindole, quinoline, isoquinoline, and carbazole. , phenoxidine, acridine, furan, piper, isobenzofuran, iso Isochromene, Thiophene, thiophene, phenanthrene Thiophene Wait. Examples of the substituent in the above heterocyclic group include a halogen group, a hydroxyl group, an alkoxy group, an amine group, and an alkyl group. Further, examples of the aromatic heterocyclic group having 5 to 10 carbon atoms in Z include a furyl group, a thienyl group, a pyridyl group, and a pyrrolyl group. Azolyl, different Azolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, pyrimidinyl and the like.

Examples of the aromatic hydrocarbon group in R ¹⁷¹ , R ¹⁷² , R ¹⁷³ , R ¹⁷⁴ and Z include a phenyl group and a naphthyl group.

^Examples of -SO ₃ R ^{178 in} R ¹⁷¹ , R ¹⁷² , R ¹⁷³ , R ¹⁷⁴ and R ¹⁷⁷ include a methylsulfonyl group, an ethylsulfonyl group, a hexylsulfonyl group, a sulfonyl group, and the like. Further, examples of -CO ₂ R ¹⁷⁸ include a methyloxycarbonyl group, an ethyloxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butyloxycarbonyl group, a cyclohexyloxycarbonyl group, and a methoxypropyloxycarbonyl group. Wait. Further, R ¹⁷⁹ and R ^{180 in} -SO ₂ NHR ¹⁷⁹ and -SO ₂ NR ¹⁷⁹ R ¹⁸⁰ are preferably a branched alkyl group having 6 to 8 carbon atoms or an alicyclic ring having 5 to 7 carbon atoms. A hydrocarbon group, an allyl group, an aralkyl group having 8 to 10 carbon atoms, a hydroxyl group-containing alkyl group having 2 to 8 carbon atoms, an alkoxy group-containing alkyl group having 2 to 8 carbon atoms, and an aryl group.

A representative example of the cation represented by the above formula (11), an example The cation represented by the following formula is mentioned.

Examples of the other cationic chromophore include a cation represented by the following formula.

The coloring agent can be produced by a known method, and can be produced, for example, by the same method as the example of JP-A-2003-206415. When the coloring agent is produced by a salt exchange reaction as described in the examples of JP-A-2003-206415, a salt of an anion represented by the above formula (1a-1) is required, but a commercially available product can be used as the salt. Further, a salt synthesized by a method described in, for example, the method described in Example 1 of JP-A-2011-133844 can be used. The present colorant thus obtained is soluble in various organic solvents typified by a ketone such as cyclohexanone, and has excellent heat resistance.

These coloring agents can be used singly or in combination of two or more.

For the coloring agent, for example, when X ⁺ is a triarylmethane-based chromophore, it is blue to red when dissolved in an organic solvent, and thus the coloring agent can be used by being appropriately mixed alone or with other coloring agents. Suitable for use in, for example, coloring compositions for forming blue pixels, red pixels, black colored layers.

The coloring composition of the present invention may contain the coloring agent as a coloring agent and may contain other coloring agents. Other coloring agents are not particularly limited, and colors and materials can be appropriately selected depending on the application.

As the other coloring agent, any of the pigment other than the coloring agent, the dye other than the coloring agent, and the natural coloring matter can be used, and from the viewpoint of obtaining a pixel having high luminance and color purity, an organic pigment or an organic dye is preferable.

The organic pigment may, for example, be a compound classified as a pigment in a color index (C.I.; issued by The Society of Dyers and Colourists), that is, a compound having the following dye index (C.I.) name.

CI Pigment Yellow 12, CI Pigment Yellow 13, CI Pigment Yellow 14, CI Pigment Yellow 17, CI Pigment Yellow 20, CI Pigment Yellow 24, CI Pigment Yellow 31, CI Pigment Yellow 55, CI Pigment Yellow 61, CI Pigment Yellow 61: 1. CI Pigment Yellow 62, CI Pigment Yellow 83, CI Pigment Yellow 93, CI Pigment Yellow 100, CI Pigment Yellow 104, CI Pigment Yellow 109, CI Pigment Yellow 110, CI Pigment Yellow 133, CI Pigment Yellow 138, CI Pigment Yellow 139, CI Pigment Yellow 150, CI Pigment Yellow 153, CI Pigment Yellow 154, CI Pigment Yellow 155, CI Pigment Yellow 166, CI Pigment Yellow 168, CI Pigment Yellow 169, CI Pigment Yellow 180, CI Pigment Yellow 183, CI Pigment Yellow 191, CI Pigment Yellow 191:1, CI Pigment Yellow 206, CI Pigment Yellow 209, CI Pigment Yellow 209:1, CI Pigment Yellow 211, CI Pigment Yellow 212; CI Pigment Orange 5, CI Pigment Orange 13, CI Pigment Orange 14 , CI Pigment Orange 24, CI Pigment Orange 34, CI Pigment Orange 36, CI Pigment Orange 38, CI Pigment Orange 40, CI Pigment Orange 43, CI Pigment Orange 46, CI Pigment Orange 49, CI Pigment Orange 61, CI Pigment Orange 64 , CI Pigment Orange 68, CI Pigment Orange 70, CI Pigment Orange 71, CI Pigment Orange 72, CI Pigment 73, CI Pigment Orange 74; CI Pigment Red 1, CI Pigment Red 2, CI Pigment Red 5, CI Pigment Red 17, CI Pigment Red 31, CI Pigment Red 32, CI Pigment Red 41, CI Pigment Red 48: 1, CI Pigment Red 48:2, CI Pigment Red 48:3, CI Pigment Red 48:4, CI Pigment Red 48:5, CI Pigment Red 49, CI Pigment Red 49:1, CI Pigment Red 49:2, CI Pigment Red 49:3, CI Pigment Red 52:1, CI Pigment Red 52:2, CI Pigment Red 53:1, CI Pigment Red 54, CI Pigment Red 57:1 , CI Pigment Red 58, CI Pigment Red 58:1, CI Pigment Red 58:2, CI Pigment Red 58:3, CI Pigment Red 58:4, CI Pigment Red 60:1, CI Pigment Red 63, CI Pigment Red 63 : 1, CI Pigment Red 63:2, CI Pigment Red 63:3, CI Pigment Red 64:1, CI Pigment Red 68, CI Pigment Red 81, CI Pigment Red 81:1, CI Pigment Red 122, CI Pigment Red 123 , CI Pigment Red 144, CI Pigment Red 149, CI Pigment Red 166, CI Pigment Red 168, CI Pigment Red 170, CI Pigment Red 171, CI Pigment Red 175, CI Pigment Red 176, CI Pigment Red 177, CI Pigment Red 178 , CI Pigment Red 179, CI Pigment Red 180, CI Pigment Red 185, CI Pigment Red 187, CI Pigment Red 200, CI Pigment Red 202, CI Pigment Red 206, CI Pigment Red 207, CI Pigment Red 209, CI Pigment Red 214 , CI Pigment Red 220, CI Pigment Red 221, CI Pigment Red 224, CI Pigment Red 237, CI Pigment Red 239, CI Pigment Red 242, CI Pigment Red 243 CI Pigment Red 247, CI Pigment Red 254, CI Pigment Red 255, CI Pigment Red 262, CI Pigment Red 264, CI Pigment Red 272; CI Pigment Violet 1, CI Pigment Violet 2, CI Pigment Violet 3, CI Pigment Violet 3: 1. CI pigment violet 3:3, CI pigment violet 19, CI pigment violet 23, CI pigment violet 27, CI pigment violet 29, CI pigment violet 32, CI pigment violet 36, CI pigment violet 38, CI pigment violet 39; CI Pigment Blue 1, CI Pigment Blue 2, CI Pigment Blue 3, CI Pigment Blue 9, CI Pigment Blue 10, CI Pigment Blue 14, CI Pigment Blue 15, CI Pigment Blue 15:3, CI Pigment Blue 15:4, CI Pigment Blue 15:6, CI Pigment Blue 17:1, CI Pigment Blue 24, CI Pigment Blue 24:1, CI Pigment Blue 56 , CI Pigment Blue 60, CI Pigment Blue 61, CI Pigment Blue 62, CI Pigment Blue 80; CI Pigment Green 1, CI Pigment Green 4, CI Pigment Green 7, CI Pigment Green 36, CI Pigment Green 58; CI Pigment Brown 23 , CI Pigment Brown 25; CI Pigment Black 1, CI Pigment Black 7.

In the present invention, when a pigment is used as another coloring agent, the pigment may be purified by a recrystallization method, a reprecipitation method, a solvent cleaning method, a sublimation method, a vacuum heating method, or a combination thereof. Further, the pigment may be used by modifying the surface of the particles with a resin as needed. For example, the resin which is described in JP-A-2001-108817 or a commercially available resin for dispersing various pigments is used as the resin for modifying the surface of the particles of the pigment. For the resin coating method of the surface of the carbon black, for example, the method described in JP-A-H09-71733, JP-A-9-95625, JP-A-9-124969, and the like can be used. Further, the organic pigment is preferably used by refining the primary particles by so-called salt polishing. As a method of salt polishing, for example, a method disclosed in Japanese Laid-Open Patent Publication No. Hei 08-179111 can be employed.

In the present invention, when a pigment is used as the other coloring agent, a well-known dispersing agent and a dispersing aid may be contained. Examples of the known dispersant include a polyurethane dispersant, a polyethyleneimine dispersant, a polyoxyethylene alkyl ether dispersant, and a polyoxyethylene alkylphenyl ether dispersant. A polyethylene glycol diester-based dispersing agent, a sorbitan fatty acid ester-based dispersing agent, a polyester-based dispersing agent, an acrylic dispersing agent, and the like, and examples of the dispersing aid include a pigment derivative.

Such a dispersant can be obtained by a commercial pipe. For example, as an acrylic dispersant, Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116, BYK-LPN21324 (above BYK CHEMIE (BYK)) As a polyurethane dispersant, Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 (above, BYK CHEMIE (BYK)) For example, Solsperse 24000 (manufactured by LUBRIZOL Co., Ltd.), etc., may be Solsperse 24000 (manufactured by LUBRIZOL Co., Ltd.), and examples of the polyester-based dispersant include Adisper PB821 and Adisper. PB822, Adisper PB880, Adisper PB881 (above, manufactured by Ajinomoto Fine-Techno Co., Ltd.), and the like.

In addition, specific examples of the pigment derivative include a copper phthalocyanine, a diketopyrrolopyrrole, and a sulfonic acid derivative of quinacridone.

In addition, the dye may be appropriately selected from various oil-soluble dyes, direct dyes, acid dyes, metal complex dyes, and the like, and examples thereof include dyes having the following dye index (C.I.) name.

CI Solvent Yellow 4, CI Solvent Yellow 14, CI Solvent Yellow 15, CI Solvent Yellow 24, CI Solvent Yellow 82, CI Solvent Yellow 88, CI Solvent Yellow 94, CI Solvent Yellow 98, CI Solvent Yellow 162, CI Solvent Yellow 179; CI Solvent Red 45, CI Solvent Red 49; CI Solvent Orange 2, CI Solvent Orange 7, CI Solvent Orange 11, CI Solvent Orange 15, CI Solvent Orange 26, CI Solvent Orange 56; CI Solvent Blue 35, CI Solvent Blue 37, CI Solvent Blue 59, CI Solvent Blue 67; CI Acid Yellow 17, CI Acid Yellow 29, CI Acid Yellow 40, CI Acid Yellow 76; CI Acid Red 91, CI Acid Red 92, CI Acid Red 97, CI Acid Red 114, CI Acid Red 138, CI Acid red 151; CI acid orange 51, CI acid orange 63; CI acid blue 80, CI acid blue 83, CI acid blue 90; CI acid green 9, CI acid green 16, CI acid green 25, CI acid green 27.

The other coloring agents in the present invention may be used singly or in combination of two or more.

In the present invention, when X ⁺ is a methine chromophore, it is preferred to form a green pixel-forming coloring composition by using the coloring agent and other green coloring agents in combination, or to form a red color by using the coloring agent and other red coloring agents. A coloring composition for pixel formation. In this case, the green colorant as the other colorant is preferably a green organic pigment, preferably at least one selected from the group consisting of CI Pigment Green 7, CI Pigment Green 36, and CI Pigment Green 58, and particularly preferably CI Pigment Green. 58. Further, the red coloring agent as the other coloring agent is preferably a red organic pigment, and is preferably at least one selected from the group consisting of CI Pigment Red 242, CI Pigment Red 254, and CI Pigment Red 264.

Further, when X ⁺ is an azo-based chromophore or a quinone imine chromophore, it is preferred to use a coloring agent, a blue coloring agent or a purple coloring agent together to form a coloring component for forming a blue pixel. Alternatively, the coloring agent and the red coloring agent are used in combination to form a coloring composition for forming a red pixel. In this case, the blue colorant as the other colorant is preferably a blue organic pigment, preferably CI Pigment Blue 15:6. Further, as the purple coloring agent of the other coloring agent, a purple organic pigment is preferable, and CI Pigment Violet 23 is preferable.

Further, when X ⁺ is a diarylmethane-based chromophore, it is preferred to form a green pixel-forming coloring composition by using the coloring agent and other green coloring agents in combination, or to use the coloring agent and other red coloring agents to form a red color. A coloring composition for pixel formation. In this case, the green colorant as the other colorant is preferably a green organic pigment, preferably at least one selected from the group consisting of CI Pigment Green 7, CI Pigment Green 36, and CI Pigment Green 58, and particularly preferably CI Pigment Green. 58. The red coloring agent as the other coloring agent is preferably a red organic pigment, and is preferably at least one selected from the group consisting of CI Pigment Red 242, CI Pigment Red 254, and CI Pigment Red 264.

In addition, X ⁺ is a chromophore, In the case of a chromophore, it is preferred to form a coloring composition for forming a blue pixel by using the coloring agent and other blue coloring agents or other purple coloring agents in combination. In this case, the blue colorant as the other colorant is preferably a blue organic pigment, preferably CI Pigment Blue 15:6. Further, as the purple coloring agent of the other coloring agent, a purple organic pigment is preferable, and CI Pigment Violet 23 is preferable.

The content ratio of the present colorant in this paragraph varies depending on the desired chromaticity characteristics, and is usually 10 to 99% by mass, and more preferably 30 to 95% by mass in the total colorant. Further preferably, it is 50 to 90% by mass.

From the viewpoint of forming a pixel having high luminance and excellent color purity or a black matrix having excellent light-shielding properties, the content of the colorant (A) is usually 5 to 70% by mass, preferably in the solid content of the coloring composition. It is 5 to 60% by mass. The solid content referred to herein means that in addition to the solvent described later External ingredients.

- (B) Adhesive Resin -

The (B) binder resin in the present invention is not particularly limited, and is preferably a resin having an acidic functional group such as a carboxyl group or a phenolic hydroxyl group. In particular, a polymer having a carboxyl group (hereinafter also referred to as a "carboxyl group-containing polymer") is preferable, and examples thereof include an ethylenically unsaturated monomer having one or more carboxyl groups (hereinafter, also referred to as "no". A copolymer of a saturated monomer (b1)") and another copolymerizable ethylenically unsaturated monomer (hereinafter also referred to as "unsaturated monomer (b2)").

Examples of the unsaturated monomer (b1) include (meth)acrylic acid, maleic acid, maleic anhydride, succinic acid mono [2-(methyl) propylene oxyethyl ester], and ω-carboxyl polymerization. Caprolactone mono(meth)acrylate, p-vinylbenzoic acid, and the like.

These unsaturated monomers (b1) can be used individually or in mixture of 2 or more types.

Further, examples of the unsaturated monomer (b2) include an N-position substituted maleimide such as N-phenylmaleimide and N-cyclohexylmaleimide; styrene; An aromatic vinyl compound such as α-methylstyrene, p-hydroxystyrene, p-hydroxy-α-methylstyrene, p-vinylbenzyl glycidyl ether or decene; methyl (meth)acrylate; N-butyl methacrylate, 2-ethylhexyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, allyl (meth)acrylate, benzyl (meth)acrylate, polyethyl b Diol (degree of polymerization 2~10) methyl ether (meth) acrylate, polypropylene glycol (degree of polymerization 2~10) methyl ether (meth) acrylate, polyethylene glycol (degree of polymerization 2~10) single (A) Acrylate, polypropylene glycol (degree of polymerization 2~10) mono (meth) acrylate, cyclohexyl (meth) acrylate, isodecyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] Decane-8-yl (meth) acrylate, dicyclopentenyl (meth) acrylate, glycerol mono (meth) acrylate, 4-hydroxyphenyl (meth) acrylate, Ethylene oxide modified (meth) acrylate of phenol, glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, 3-[(meth) propylene (Meth) acrylate such as mercaptooxymethyl]oxetane or 3-[(meth)acryloyloxymethyl]-3-ethyloxetane; cyclohexyl vinyl ether , isodecyl vinyl ether, tricyclo [5.2.1.0 ^2,6 ]decane-8-yl vinyl ether, pentacyclopentadecyl vinyl ether, 3-(vinyloxymethyl)-3- a vinyl ether such as ethyloxetane; a polymer molecular chain such as polystyrene, poly(methyl) methacrylate, poly(methyl) methacrylate, or polyoxyalkylene has a single molecular terminal A (methyl) acrylonitrile-based macromonomer or the like.

These unsaturated monomers (b2) can be used individually or in mixture of 2 or more types.

In the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2), the copolymerization ratio of the unsaturated monomer (b1) in the copolymer is preferably from 5 to 50% by mass, further preferably 10 ~40% by mass. By copolymerizing the unsaturated monomer (b1) in such a range, a coloring composition excellent in alkali developability and storage stability can be obtained.

Specific examples of the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2) include JP-A-7-140654, JP-A-8-259876, and JP-A-10-10 No. 31308 Copolymerization disclosed in, for example, Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Things.

In the present invention, for example, Japanese Laid-Open Patent Publication No. Hei 5-19467, Japanese Patent Application Laid-Open No. Hei No. Hei. No. Hei. No. Hei. A carboxyl group-containing polymer having a polymerizable unsaturated bond such as a (meth) acrylonitrile group in a side chain as a binder resin may be used as disclosed in JP-A-2008-181095, and the like.

The polystyrene-equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (hereinafter abbreviated as GPC) (eluent solvent: tetrahydrofuran) in the present invention is usually 1,000 to 100,000, preferably 3,000. 50,000. When the Mw is too small, the residual film ratio of the film to be obtained may be lowered, or the pattern shape, heat resistance, or the like may be impaired, or electrical characteristics may be deteriorated. On the other hand, if the film size is too large, the resolution may be lowered or the pattern shape may be impaired. Or it may become easy to produce dry foreign matter at the time of coating by the slit nozzle method.

Further, the ratio (Mw/Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) of the binder resin in the present invention is preferably from 1.0 to 5.0, more preferably from 1.0 to 3.0. In addition, the term "Mn" as used herein means a polystyrene-equivalent number average molecular weight measured by GPC (solution solvent: tetrahydrofuran).

The binder resin in the present invention can be produced by a known method, for example, by Japanese Patent Laid-Open Publication No. 2003-222717, Japan. The method disclosed in JP-A-2006-259680, the pamphlet of International Publication No. 07/029871, and the like, controls the structure, Mw, and Mw/Mn.

In the present invention, the binder resin may be used singly or in combination of two or more.

In the present invention, the content of the binder resin is usually 10 to 1,000 parts by mass, preferably 20 to 500 parts by mass, per 100 parts by mass of the (A) colorant. If the content of the binder resin is too small, for example, the alkali developability may be lowered, or the storage stability of the obtained colored composition may be lowered. On the other hand, if the amount is too large, the concentration of the colorant is relatively lowered, so that it may be difficult as a film. Achieve target color density.

-(C) Crosslinker -

In the present invention, the (C) crosslinking agent means a compound having two or more polymerizable groups. Examples of the polymerizable group include an ethylenically unsaturated group, an oxiranyl group, an oxetanyl group, and an N-alkoxymethylamino group. In the present invention, the (C) crosslinking agent is preferably a compound having two or more (meth)acryl fluorenyl groups or a compound having two or more N-alkoxymethylamino groups.

Specific examples of the compound having two or more (meth) acryloyl fluorenyl groups include polyfunctional (meth) acrylates obtained by reacting an aliphatic polyhydroxy compound with (meth)acrylic acid. An ester-modified polyfunctional (meth) acrylate, an alkylene oxide-modified polyfunctional (meth) acrylate, a polyfunctional amine group obtained by reacting a (meth) acrylate having a hydroxyl group and a polyfunctional isocyanate A formate (meth) acrylate, a polyfunctional (meth) acrylate having a carboxyl group obtained by reacting a (meth) acrylate having a hydroxyl group and an acid anhydride, and the like.

Here, examples of the aliphatic polyhydroxy compound include a two-membered aliphatic polyhydroxy compound such as ethylene glycol, propylene glycol, polyethylene glycol, and polypropylene glycol; glycerin, trimethylolpropane, and pentaerythritol. A trivalent or higher aliphatic polyhydroxy compound such as dipentaerythritol. Examples of the (meth) acrylate having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, trimethylolpropane bis(meth)acrylate, and pentaerythritol tri(meth)acrylic acid. Ester, dipentaerythritol penta (meth) acrylate, glycerol dimethacrylate, and the like. Examples of the polyfunctional isocyanate include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate. Examples of the acid anhydride include acid anhydrides of dibasic acids such as succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, and hexahydrophthalic anhydride, and pyromellitic dianhydride. A tetrabasic acid dianhydride such as biphenyltetracarboxylic dianhydride or benzophenone tetracarboxylic dianhydride.

In addition, the compound described in paragraphs [0015] to [0018] of JP-A-11-44955 is exemplified as the above-mentioned caprolactone-modified polyfunctional (meth) acrylate. The polyalkylene oxide-modified polyfunctional (meth)acrylate may be at least one selected from the group consisting of an ethylene oxide adduct selected from bisphenol A and a propylene oxide adduct of bisphenol A. The modified bis(meth)acrylate is modified from at least one selected from the group consisting of an ethylene oxide adduct of isocyanuric acid and a propylene oxide adduct of isocyanuric acid. Tris (meth) acrylate, modified from at least one of an ethylene oxide adduct selected from trimethylolpropane and a propylene oxide adduct of trimethylolpropane At least one of an acrylate, an ethylene oxide adduct selected from neopentyl alcohol, and a propylene oxide adduct of neopentyl alcohol The modified tri(meth)acrylate, modified from at least one of an ethylene oxide adduct selected from neopentyl alcohol and a propylene oxide adduct of neopentyl alcohol a tetra (meth) acrylate, a modified one of at least one selected from the group consisting of an ethylene oxide adduct selected from dipentaerythritol and a propylene oxide adduct of dipentaerythritol a methyl (meth) acrylate, a hexa(methyl) modified from at least one selected from the group consisting of an ethylene oxide adduct of dipentaerythritol and a propylene oxide adduct of dipentaerythritol Acrylate and the like.

In addition, examples of the compound having two or more N-alkoxymethylamino groups include a compound having a melamine structure, a benzoguanamine structure, and a urea structure. It should be noted that the melamine structure and the benzoguanamine structure refer to having one or more three Ring or phenyl substituted three The chemical structure of the ring as a basic skeleton also includes the concept of melamine, benzoguanamine or their condensates. Specific examples of the compound having two or more N-alkoxymethylamino groups include N,N,N',N',N",N"-hexa(alkoxymethyl)melamine, and N. , N, N', N'-tetrakis(alkoxymethyl)benzoguanamine, N, N, N', N'-tetrakis(alkoxymethyl) glycoluril, and the like.

Among these crosslinking agent compounds, a polyfunctional (meth) acrylate obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth)acrylic acid, or a caprolactone-modified polyfunctional (methyl group) is preferred. Acrylate, polyfunctional urethane (meth) acrylate, polyfunctional (meth) acrylate having carboxyl group, N, N, N', N', N", N"-hexa (alkoxy) Methyl) melamine, N, N, N', N'-tetrakis(alkoxymethyl)benzoguanamine. From the viewpoint of high strength of the colored layer, excellent surface smoothness of the colored layer, and difficulty in generating scum, film residue, and the like on the substrate of the unexposed portion and the light shielding layer, the aliphatic group having three or more members is more Hydroxy compound and (meth)acrylic acid Among the polyfunctional (meth) acrylates to be obtained, trimethylolpropane triacrylate, neopentyl alcohol triacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate are particularly preferred. An ester, particularly a polyfunctional (meth) acrylate having a carboxyl group, is a compound obtained by reacting pentaerythritol triacrylate with succinic anhydride, and reacting dipentaerythritol pentaacrylate with succinic anhydride. The compound obtained.

In the present invention, the (C) crosslinking agent may be used singly or in combination of two or more.

The content of the (C) crosslinking agent in the present invention is preferably 10 to 1,000 parts by mass, particularly preferably 20 to 500 parts by mass, per 100 parts by mass of the (A) coloring agent. At this time, if the content of the crosslinking agent is too small, sufficient curability may not be obtained. On the other hand, when the content of the crosslinking agent is too large, when the alkali developability is imparted to the colored composition of the present invention, the alkali developability is lowered, and scum or film is likely to be generated on the substrate or the light-shielding layer of the unexposed portion. Residual trends such as.

-Photopolymerization initiator -

The coloring composition of the present invention may contain a photopolymerization initiator. Thereby, the coloring composition can be imparted with radiation. The photopolymerization initiator used in the present invention is a compound which generates an active species capable of initiating polymerization of (C) a crosslinking agent by exposure to radiation such as visible light, ultraviolet rays, far ultraviolet rays, electron beams, and X-rays.

Examples of such a photopolymerization initiator include a thioxanthone compound, an acetophenone compound, a biimidazole compound, and the like. Compound, O-mercapto oxime compound, sulfonium salt compound, benzoin compound, benzophenone compound, α-diketone compound, polycyclic guanidine compound, diazo compound, quinone A sulfonate-based compound, a phosphonium salt-based compound, or the like.

In the present invention, the photopolymerization initiator may be used singly or in combination of two or more. The photopolymerization initiator is preferably selected from the group consisting of a thioxanthone compound, an acetophenone compound, a biimidazole compound, and three At least one of a compound and an O-mercapto lanthanide compound.

In a preferred photopolymerization initiator of the present invention, specific examples of the thioxanthone-based compound include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, and 2-isopropyl group. Thioxanthone, 4-isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-di Isopropyl thioxanthone and the like.

Further, specific examples of the acetophenone-based compound include 2-methyl-1-[4-(methylthio)phenyl]-2- Lolinylpropan-1-one, 2-benzyl-2-dimethylamino-1-(4- Polinylphenyl)butan-1-one, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4- Polinylphenyl)butan-1-one and the like.

Further, specific examples of the biimidazole-based compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole. , 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4 , 6-trichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, and the like.

In the case where a biimidazole-based compound is used as the photopolymerization initiator, it is preferred to use a hydrogen donor in combination from the viewpoint of improving the sensitivity. The term "hydrogen donor" as used herein refers to a compound which can supply a hydrogen atom to a radical generated by a biimidazole-based compound by exposure. Examples of the hydrogen donor include 2-mercaptobenzothiazole and 2-mercaptobenzoene. A thiol-based hydrogen donor such as oxazole; an amine-based hydrogen supply such as 4,4'-bis(dimethylamino)benzophenone or 4,4'-bis(diethylamino)benzophenone body. In the present invention, the hydrogen donor may be used alone or in combination of two or more. From the viewpoint of further improving the sensitivity, it is preferred to combine one or more kinds of thiol-based hydrogen donors and one or more amine-based hydrogen donors. use.

In addition, as the above three Specific examples of the compound include 2,4,6-tris(trichloromethyl)-s-three. 2-methyl-4,6-bis(trichloromethyl)-s-three ,2-[2-(5-methylfuran-2-yl)vinyl]-4,6-bis(trichloromethyl)-s-three ,2-[2-(furan-2-yl)vinyl]-4,6-bis(trichloromethyl)-s-three 2-[2-(4-Diethylamino-2-methylphenyl)vinyl]-4,6-bis(trichloromethyl)-s-three ,2-[2-(3,4-dimethoxyphenyl)vinyl]-4,6-bis(trichloromethyl)-s-three , 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-three , 2-(4-ethoxystyryl)-4,6-bis(trichloromethyl)-s-three ,2-(4-n-butoxyphenyl)-4,6-bis(trichloromethyl)-s-three Three with a halogenated methyl group a compound.

Further, specific examples of the O-mercapto fluorene-based compound include 1,2-octanedione-1-[4-(phenylthio)phenyl]-2-(O-benzamide), Ethyl ketone-1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]-1-(O-acetamidine), ethyl ketone-1-[ 9-Ethyl-6-(2-methyl-4-tetrahydrofurylmethoxybenzylidene)-9H-indazol-3-yl]-1-(O-acetyl), ethyl ketone-1 -[9-ethyl-6-{2-methyl-4-(2,2-dimethyl-1,3-dioxolanyl)methoxybenzylidene}9H-carbazole-3 -yl]-1-(O-acetamidine) and the like. As a commercial item of the O-mercapto fluorene-based compound, NCI-831, NCI-930 (above, manufactured by ADEKA Co., Ltd.), or the like can be used.

In the present invention, a biimidazole-based compound such as an acetophenone-based compound is used. In the case of a photopolymerization initiator other than the compound, a sensitizer may be used in combination. Examples of such a sensitizer include 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, and 4-di Ethylaminoacetophenone, 4-dimethylaminopropiophenone, ethyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylhexyl benzoate, 2,5 - bis(4-diethylaminobenzylidene)cyclohexanone, 7-diethylamino-3-(4-diethylaminobenzimidyl)coumarin, 4-(2-B Amino group) Chalcone and the like.

In the present invention, the content of the photopolymerization initiator is preferably 0.01 to 120 parts by mass, particularly preferably 1 to 100 parts by mass, per 100 parts by mass of the (C) crosslinking agent. At this time, if the content of the photopolymerization initiator is too small, the curing due to exposure may be insufficient. On the other hand, if the amount is too large, the formed coloring layer tends to fall off from the substrate during development.

- solvent -

The colored composition of the present invention contains the above components (A) to (C) and optionally added other components, and usually, a solvent is prepared to prepare a liquid composition. The solvent is appropriately selected and used as long as it disperses or dissolves the components (A) to (C) constituting the colored composition and does not react with these components and has moderate volatility.

Examples of such a solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, and diethylene glycol. Monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether , propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol single (poly) olefinic diol monoalkyl ethers such as methyl ether, tripropylene glycol monoethyl ether; alkyl lactate such as methyl lactate or ethyl lactate; methanol, ethanol, propanol, butanol, isopropanol, iso (cyclo)alkyl alcohols such as butanol, tertiary butanol, octanol, 2-ethylhexanol, cyclohexanol; ketone alcohols such as diacetone alcohol; ethylene glycol monomethyl ether acetate, ethylene Alcohol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether acetate (poly)olefin diol monoalkyl ether acetates such as ester, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate; diethylene glycol II Other ethers such as methyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone; propylene glycol Diacetate such as diacetate, 1,3-butanediol diacetate or 1,6-hexanediol diacetate; methyl 3-methoxypropionate, 3-methoxypropene Ethyl acetate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethoxylate Alkoxycarboxylates such as ethyl acetate and 3-methyl-3-methoxybutylpropionate; ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate Ester, n-amyl formate, isoamyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate , other esters such as n-propyl pyruvate, methyl acetate, ethyl acetate, ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; N,N-dimethyl Indoleamine, N,N-dimethylacetamide, N-methylpyridinium Amidoxime or an indoleamine such as a pyridone.

Among these solvents, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, and propylene glycol are preferable from the viewpoints of solubility, pigment dispersibility, and coatability. Ethyl acetate, 3-methoxybutyl acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, 1, 3-butanediol diacetate, 1,6-hexanediol diacetate, ethyl lactate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propyl propionate, 3-methyl-3-methoxybutyl propionate, n-butyl acetate, isobutyl acetate, n-amyl formate, isoamyl acetate, n-butyl propionate, butyric acid Ethyl ester, isopropyl butyrate, n-butyl butyrate, ethyl pyruvate, and the like.

In the present invention, the solvent may be used singly or in combination of two or more.

The content of the solvent is not particularly limited, and the total concentration of each component other than the solvent of the coloring composition is preferably from 5 to 50% by mass, more preferably from 10 to 40% by mass. In such a manner, a colorant dispersion having good dispersibility and stability and a colored composition having good coatability can be obtained.

-additive-

The colored composition of the present invention may further contain various additives as needed.

Examples of the additive include a filler such as glass or alumina; a polymer compound such as polyvinyl alcohol or poly(fluoroalkyl acrylate); a surfactant such as a fluorine-based surfactant or an anthrone-based surfactant; ; vinyl trimethoxy decane, vinyl triethoxy decane, vinyl tris(2-methoxyethoxy) decane, N-(2-aminoethyl)-3-aminopropylmethyl Dimethoxydecane, N-(2-aminoethyl)-3-aminopropyltrimethoxydecane, 3-aminopropyltriethoxydecane, 3-glycidoxypropyltrimethyl Oxydecane, 3-glycidoxypropylmethyldimethoxydecane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, 3-chloropropylmethyldimethoxy a adhesion promoter such as decane, 3-chloropropyltrimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane, 3-mercaptopropyltrimethoxydecane; 2,2-thiobis An antioxidant such as (4-methyl-6-tertiary butylphenol) or 2,6-ditributylphenol; 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole, alkoxybenzophenone and other ultraviolet absorbers; anti-aggregating agents such as sodium polyacrylate; malonic acid, adipic acid, itaconic acid, citraconic acid, fumaric acid , mesaconic acid, 2-aminoethanol, 3-amino-1-propanol, 5-amino-1-pentanol, 3-amino-1,2-propanediol, 2-amino-1,3 - residue improving agent such as propylene glycol or 4-amino-1,2-butanediol; succinic acid mono [2-(methyl) propylene methoxyethyl] ester, phthalic acid mono [2-(methyl) Acetyleneoxyethyl]ester, ω-carboxyl A developer improving agent such as a polycaprolactone mono(meth)acrylate; a siloxane oligomer having a reactive functional group disclosed in JP-A-2008-242078 or the like.

The colored composition of the present invention can be produced by a suitable method, and when the coloring agent is a dye, it can be produced, for example, by a method disclosed in JP-A-2008-58642, JP-A-2010-132874, and the like. When both the coloring agent and the pigment as the dye are used as the coloring agent, as shown in Japanese Laid-Open Patent Publication No. 2010-132874, the following method may be employed: after the dye solution containing the coloring agent or the like is passed through the first filter, The dye solution that has passed through the first filter is mixed with a separately prepared pigment dispersion or the like, and the obtained colored composition is passed through a second filter. Ready. In addition, a method may be employed in which a dye containing the coloring agent or the like and the components (B) to (C) and, if necessary, other components are dissolved in a solvent, and the obtained solution is passed through the first filter. The solution that passed through the first filter was mixed with a separately prepared pigment dispersion, and the obtained colored composition was passed through a second filter to prepare. In addition, a dye solution containing the coloring agent or the like may be passed through the first filter, and the dye solution that has passed through the first filter and the components (B) to (C) and, if necessary, may be used. Mix other ingredients. After the solution was dissolved, the obtained solution was passed through a second filter, and the solution passed through the second filter was further mixed with the separately prepared pigment dispersion, and the obtained colored composition was passed through a third filter to prepare.

Color filter and manufacturing method thereof

The color filter of the present invention is provided with a coloring layer containing the present coloring agent.

As a method of manufacturing a color filter, the following method is mentioned first. First, a light shielding layer (black matrix) is formed on the surface of the substrate in such a manner as to divide a portion where pixels are formed. Next, a liquid composition of the blue radiation-sensitive composition of the present invention containing the coloring agent, for example, is applied onto the substrate, and then pre-baked to evaporate the solvent to form a coating film. Then, the coating film was exposed through a photomask, and then developed with an alkali developing solution to dissolve and remove the unexposed portion of the coating film. Thereafter, a pixel array in which a blue pixel pattern is formed by a predetermined sequence is formed by post-baking.

Next, using the green or red respective radiation-sensitive coloring composition, coating, prebaking, exposing, developing, and post-baking each of the radiation-sensitive coloring compositions are performed in the same manner as described above, and green is sequentially formed on the same substrate. Pixel array and red pixel array. Thereby getting A color filter of a pixel array of three primary colors of red, green, and blue is disposed on the substrate. However, in the present invention, the order in which the pixels of the respective colors are formed is not limited to the above order. Further, in the first method of manufacturing a color filter, any one or more of the blue, green, and red pixel arrays may be a coloring layer formed using the coloring composition of the present invention.

Further, the black matrix may be formed by forming a metal film such as chromium which is formed by sputtering or vapor deposition into a desired pattern by photolithography, or a radiation-sensitive coloring composition in which a black colorant is dispersed may be used. It is formed in the same manner as the case where the above-described pixels are formed. The colored composition of the present invention is also suitable for the formation of the black matrix.

Examples of the substrate used for forming the color filter include glass, ruthenium, polycarbonate, polyester, aromatic polyamide, polyamidimide, and polyimide.

Further, for these substrates, if necessary, appropriate pretreatment such as reagent treatment using a decane coupling agent, plasma treatment, ion plating, sputtering, gas phase reaction method, or vacuum vapor deposition may be performed.

When the radiation sensitive coloring composition is applied to a substrate, an appropriate coating method such as a spray coating method, a roll coating method, a spin coating method (spin coating method), a slit die coating method, or a bar coating method may be employed. Spin coating method, slit type die coating method.

Pre-baking is usually carried out by combining dry-pressure drying and heat drying. Drying under reduced pressure usually proceeds to 50 to 200 Pa. In addition, the conditions of heat drying are usually 70 to 110 ° C for about 1 to 10 minutes.

The coating thickness is usually 0.6 to 8 μm, preferably 1.2 to 5 μm, in terms of the film thickness after drying.

Examples of the light source for forming the pixel and/or the black matrix include a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a medium pressure mercury lamp, a low pressure mercury lamp, and the like. Light source, argon ion laser, YAG laser, XeCl excited molecular laser, nitrogen laser and other laser sources. As the exposure light source, an ultraviolet LED can also be used. Radiation having a wavelength in the range of 190 to 450 nm is preferred.

The exposure amount of the radiation is generally preferably from 10 to 10,000 J/m ² .

Further, as the alkaline developing solution, for example, sodium carbonate, sodium hydroxide, sodium hydrogencarbonate, potassium hydroxide, tetramethylammonium hydroxide, choline or 1,8-diguanidine is preferred [5.4.0] An aqueous solution of -7-undecene, 1,5-dibicyclobicyclo[4.3.0]-5-nonene or the like.

A water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like may be added to the alkaline developing solution in an appropriate amount. It should be noted that water washing is usually carried out after alkaline development.

As the development treatment method, a shower development method, a spray development method, a dip development method, a paddle type (liquid pool method) development method, or the like can be used. The development conditions are preferably 5 to 300 seconds at normal temperature.

The post-baking conditions are usually about 120 to 280 ° C for about 10 to 60 minutes. From the viewpoint of heat resistance of the coloring agent, the post-baking temperature is preferably 240 ° C or less, and particularly preferably 230 ° C or less.

The film thickness of the pixel thus formed is usually 0.5 to 5 μm, preferably 1 to 3 μm.

In addition, as a second method of manufacturing a color filter, Japanese Patent Laid-Open Publication No. Hei 7-318723, No. 2000-310706 A method of obtaining pixels of respective colors by an inkjet method disclosed in Japanese Laid-Open Patent Publication. In this method, first, a partition wall having a light blocking function is formed on the surface of the substrate. Next, in the formed partition walls, for example, a liquid composition of the thermosetting coloring composition of the present invention containing blue of the present coloring agent is ejected by an inkjet device, and then prebaked to evaporate the solvent. Next, the coating film is exposed as needed, and then post-baked to be cured to form a blue pixel.

Next, using each of the green or red thermosetting coloring composition, a green pixel pattern and a red pixel pattern are sequentially formed on the same substrate in the same manner as described above. Thereby, a color filter in which pixel patterns of three primary colors of red, green, and blue are arranged on the substrate is obtained. However, in the present invention, the order in which the pixels of the respective colors are formed is not limited to the above order. Further, in the second method of producing a color filter, any one or more of the blue, green, and red pixel arrays may be a coloring layer formed using the colored composition of the present invention.

In addition, the partition wall not only has a light-shielding function, but also has a function of not mixing colors of the coloring compositions discharged into the divided regions, and thus the film thickness is thicker than the black matrix used in the first method. Therefore, the partition walls are usually formed using a black sensitizing radioactive composition. The substrate used for forming the color filter, the light source of the radiation, and the method and conditions of the prebaking and postbaking are the same as those of the first method described above. The film thickness of the pixel formed by the ink jet method is the same as the height of the partition wall.

After the protective film is formed on the pixel pattern thus obtained as needed, a transparent conductive film is formed by sputtering. After forming a transparent conductive film It is also possible to further form a spacer to form a color filter. The spacer is usually formed using a radiation-sensitive composition, and may be formed into a light-shielding spacer (black spacer). At this time, a radiation-sensitive coloring composition in which a black colorant is dispersed is used, but the coloring composition of the present invention can also be applied to the formation of the black spacer.

Since the color filter of the present invention thus obtained has extremely high luminance and color purity, it is extremely useful for a color liquid crystal display element, a color image sensor element, a color sensor, an organic EL display element, electronic paper, and the like.

Display component

The display element of the present invention includes the color filter of the present invention. Examples of the display element include a color liquid crystal display element, an organic EL display element, and electronic paper.

The color liquid crystal display element having the color filter of the present invention may be of a transmissive type or a reflective type, and an appropriate structure may be employed. For example, a color filter may be formed on a substrate different from a driving substrate on which a thin film transistor (TFT) is disposed, and the driving substrate and the substrate on which the color filter is formed may be disposed to face each other via a liquid crystal layer; A structure in which a color filter is formed on a surface of a driving substrate on which a thin film transistor (TFT) is disposed, and a substrate on which an ITO (tin-doped indium oxide) electrode is formed may be disposed opposite to each other via a liquid crystal layer. . The structure of the latter can significantly increase the aperture ratio, and has the advantage of obtaining a bright and high-definition liquid crystal display element.

The color liquid crystal display element including the color filter of the present invention may include a backlight unit using a white LED as a light source in addition to a cold cathode fluorescent lamp (CCFL). Examples of the white LED include a white LED in which a red LED, a green LED, and a blue LED are combined to obtain white light by color mixing, and a blue LED, a red LED, and a green phosphor are combined to obtain white light by color mixing. a white LED that combines a blue LED, a red illuminating phosphor, and a green illuminating phosphor to obtain a white light white LED by color mixing, and obtain a white light by mixing a blue LED and a YAG fluorescent body. A white LED that combines a blue LED, an orange illuminating phosphor, and a green illuminating phosphor to obtain a white light white LED by mixing colors, and to illuminate the ultraviolet LED, the red luminescent phosphor, the green luminescent phosphor, and the blue illuminating The phosphor combines to obtain a white light white LED or the like by color mixing.

In the color liquid crystal display device including the color filter of the present invention, TN (Twisted Nematic) type, STN (Super Twisted Nematic) type, and IPS (In-Planes Switching) type can be applied. A suitable liquid crystal mode such as an internal switching type, a VA (Vertical Alignment) type, or an OCB (Optically Compensated Birefringence) type.

In addition, the organic EL display element having the color filter of the present invention may have a suitable structure, and for example, a structure disclosed in Japanese Laid-Open Patent Publication No. Hei 11-307242.

Further, the electronic paper including the color filter of the present invention may have a suitable structure, and for example, a structure disclosed in Japanese Laid-Open Patent Publication No. 2007-41169 can be cited.

[Examples]

Hereinafter, the embodiments will be enumerated, and the present invention will be further specifically described. The implementation of the Ming. However, the invention is not limited to the following examples.

<Synthesis and Evaluation of the Colorant>

1. Synthesis of the colorant

Synthesis Example 1

The hydrazine chloride (12 mmol) was dissolved in 10 mL of DMF, and after cooling at 0 ° C, potassium sulfonate 3-sulfonate (10 mmol) was added portionwise. After reacting for 5 hours, the reaction mixture was concentrated, and acetone was added thereto to remove the resulting salt, and the filtrate was concentrated to give a compound represented by the formula (A1) below. The obtained compound was used as the intermediate 1.

Synthesis Example 2

Trifluoromethanesulfonamide (20.1 mmol) manufactured by Tokyo Chemical Industry Co., Ltd. was dissolved in 30 mL of dichloromethane, and the internal temperature was cooled to 5 ° C or lower. Triethylamine (50.4 mmol) manufactured by Wako Pure Chemical Industries Co., Ltd. was added dropwise at an internal temperature of not more than 10 ° C, and after completion of the dropwise addition, Intermediate 1 (20.1 mmol) was added at 10 ° C or lower. After stirring at 5 ° C or lower for 1 hour, the mixture was further stirred at room temperature for 5 hours, and 100 mL of water was added to the reaction mixture for extraction. The organic layer was separated and washed with magnesium sulfate, and the organic layer was concentrated under reduced pressure with an evaporator to give the compound of the formula (A2) below. The obtained compound was used as the intermediate 2.

Synthesis Example 3

C.I. Basic Blue 7 (2.70 mmol) and 300 mL of water were placed in a 3-neck flask, and the mixture was heated to 80 ° C while stirring, and stirred until dissolved. Thereafter, a solution obtained by dissolving Intermediate 2 (5.40 mmol) in 10 mL of water was added, and the mixture was heated at the same temperature for 1 hour. After cooling the reaction solution to room temperature, it was allowed to stand at -15 ° C for 12 hours. Thereafter, the temperature was raised to room temperature, and the supernatant was removed by decantation. 100 mL of ice water was poured into the residue and washed. Repeat the same operation 3 times. The obtained solid was dried under reduced pressure at 60 ° C to yield 450 mg of a blue-black solid.

The compound obtained by the measurement of ¹ H-NMR spectrum (solvent: deuterated chloroform) was confirmed to be a compound represented by the following formula (A3). The obtained compound was designated as the dye (A-1).

Synthesis Example 4

In the synthesis example 2, a compound represented by the following formula (A4) was obtained in the same manner except that methacrylium ruthenium chloride was used instead of the intermediate 1. The obtained compound was used as the intermediate 3.

Synthesis Example 5

In the synthesis example 3, the intermediate agent 3 was used instead of the intermediate 2, and the coloring agent was synthesized in the same manner. The compound obtained by the measurement of the ¹ H-NMR spectrum (solvent: deuterated chloroform) was confirmed to be a compound represented by the following formula (A5). The obtained compound was designated as a dye (A-2).

Synthesis Example 6

In the synthesis example 3, a coloring agent was synthesized in the same manner except that CI basic violet 16 which is a methine-based basic dye was used instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was designated as a dye (A-3).

Synthesis Example 7

In the synthesis example 3, a coloring agent was synthesized in the same manner except that CI basic red 13 which is a methine-based basic dye was used instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was designated as a dye (A-4).

Synthesis Example 8

In the synthesis example 3, a coloring agent was synthesized in the same manner except that CI basic yellow 21 as a methine-based basic dye was used instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was designated as a dye (A-5).

Synthesis Example 9

In the synthesis example 3, a coloring agent was synthesized in the same manner except that CI basic blue 41 which is an azo basic dye was used instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was designated as a dye (A-6).

Synthesis Example 10

In the synthesis example 3, a coloring agent was synthesized in the same manner except that CI basic yellow 25 as an azo basic dye was used instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was designated as a dye (A-7).

Synthesis Example 11

In the synthesis example 3, a coloring agent was synthesized in the same manner except that CI basic orange 24 as an azo basic dye was used instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was designated as a dye (A-8).

Synthesis Example 12

In the synthesis example 3, a coloring agent was synthesized in the same manner except that CI basic yellow 2 as a diarylmethane-based basic dye was used instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was designated as a dye (A-9).

Synthesis Example 13

In the synthesis example 3, a coloring agent was synthesized in the same manner except that CI basic blue 3 which is a quinone imine basic dye was used instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was used as a dye (A-10).

Synthesis Example 14

In the synthesis example 3, a coloring agent was synthesized in the same manner except that CI basic red 2 which is a quinone imine basic dye was used instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was used as a dye (A-11).

Synthesis Example 15

In the synthesis example 3, a coloring agent was synthesized in the same manner except that CI basic blue 22 which is an lanthanoid basic dye was used instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was designated as a dye (A-12).

Synthesis Example 16

In Synthesis Example 3, it was used as A coloring agent was synthesized in the same manner as in the case of CI basic blue 11:1 which is a basic dye instead of CI basic blue 7. The objective compound was confirmed by ¹ H-NMR spectrum (solvent: deuterated chloroform). The obtained compound was designated as a dye (A-13).

2. Evaluation of the colorant

The dyes (A-1) to (A-13) obtained in each of the above Synthesis Examples are all dissolved in cyclohexanone at 10% by mass or more.

Further, the temperature at which the dyes (A-1) to (A-13) were reduced by 5% by mass based on the thermogravimetric-differential heat simultaneous measurement analysis was 250 °C or higher. On the other hand, CI alkaline blue 7, CI alkaline violet 16, CI alkaline red 13, CI alkaline yellow 21, CI alkaline blue 41, CI alkaline yellow 25, CI alkaline orange 24, CI alkaline yellow 2. The temperature of the 5% mass reduction based on the thermogravimetry-differential heat simultaneous measurement of CI basic blue 3, CI basic red 2, CI basic blue 22 and CI basic violet 11:1 was less than 200 °C. Incidentally, it can be said that the reduction by 5% based on the thermogravimetric-differential heat simultaneous measurement analysis is performed, and the higher the temperature, the higher the heat resistance of the colorant.

<Preparation of Pigment Dispersion>

Preparation Example 1

15 parts by mass of CI Pigment Violet 23 as a coloring agent, 12.5 parts by mass (solid content concentration: 40% by mass) of BYK-LPN21116 (manufactured by BYK Chemie (BYK) Co., Ltd.) as a dispersing agent, and 72.5 parts by mass of propylene glycol monomethyl ether acetate The ester was treated as a solvent by a bead mill to prepare a pigment dispersion liquid (a-1).

<Preparation of dye solution>

Preparation Example 2

15 parts by weight of mixed dye (A-1) and 85 parts by weight of cyclohexanone, prepared and dyed Solution solution (A-1).

Preparation Example 3

In the same manner as in Preparation Example 2, a dye solution (A-2) was prepared in the same manner as in Production Example 2 except that the dye (A-2) was used instead of the dye (A-1).

Preparation Example 4

In the preparation example 2, a dye solution (A-3) was prepared in the same manner as in Production Example 2 except that C.I. Basic Blue 7 was used instead of the dye (A-1).

Preparation Example 5

In the same manner as in Preparation Example 2, a dye solution (A-4) was prepared in the same manner as in Production Example 2 except that the dye (A-4) was used instead of the dye (A-1).

Preparation Example 6

In the same manner as in Preparation Example 2, a dye solution (A-5) was prepared in the same manner as in Production Example 2 except that the dye (A-6) was used instead of the dye (A-1).

Preparation Example 7

In the same manner as in Preparation Example 2, a dye solution (A-6) was prepared in the same manner as in Production Example 2 except that the dye (A-11) was used instead of the dye (A-1).

Preparation Example 8

In the same manner as in Preparation Example 2, a dye solution (A-7) was prepared in the same manner as in Production Example 2 except that the dye (A-13) was used instead of the dye (A-1).

<Synthesis of binder resin>

In a flask equipped with a cooling tube and a stirrer, 100 parts by mass of propylene glycol monomethyl ether acetate was added and replaced with nitrogen. The mixture was heated to 80 ° C, and 100 parts by mass of propylene glycol monomethyl ether acetate, 20 parts by mass of methacrylic acid, 10 parts by mass of styrene, 5 parts by mass of benzyl methacrylate, and methacrylic acid were added dropwise at the same temperature for 1 hour. 2-hydroxyethyl ester 15 parts by mass, methacrylic acid 23 parts by mass of 2-ethylhexyl ester, 12 parts by mass of N-phenylmaleimide, 15 parts by mass of mono(2-propenyloxyethyl) succinate, and 2,2'-azobis (6,4-Dimethylvaleronitrile) 6 parts by mass of a mixed solution, and polymerization was maintained at this temperature for 2 hours. Then, the temperature of the reaction solution was raised to 100 ° C, and further polymerization was carried out for 1 hour, whereby a binder resin solution (solid content concentration: 33% by mass) was obtained. The resulting binder resin had a Mw of 12,200 and an Mn of 6,500. This binder resin is referred to as "adhesive resin (B1)".

<Evaluation of Voltage Retention Rate>

Example 1

7.2 parts by mass of the dye solution (A-1), 9.9 parts by mass of a binder resin (B1) solution as a binder resin, M-402 (dipentaerythritol hexaacrylate) manufactured by Toagosei Co., Ltd. as a crosslinking agent a mixture of an ester and dipentaerythritol pentaacrylate) 15.4 parts by mass of 2-benzyl-2-dimethylamino-1-(4-) as a photopolymerization initiator L-phenylphenyl)butan-1-one (manufactured by Ciba Specialty Chemicals, trade name IRGACURE 369) 1.8 parts by mass, NCI-930 (made by Adeka Co., Ltd.) 0.1 part by weight, MEGAFAC F- as a fluorine-based surfactant 554 (manufactured by DIC Corporation) 0.2 parts by mass and ethyl lactate as a solvent were mixed to prepare a colored composition (CR1) having a solid content concentration of 20% by mass.

An SiO ₂ film for preventing elution of sodium ions is formed on the surface, and an ITO (indium-tin oxide alloy) electrode is vapor-deposited into a predetermined shape, and the obtained colored composition (CR1) is spin-coated on the thus formed soda glass substrate. The film was prebaked for 1 minute using a hot plate at 100 ° C to form a film having a film thickness of 2.0 μm. Next, the film was exposed without exposure to a photomask at an amount of exposure of 700 J/m ² . Thereafter, the substrate was immersed in a developing solution of a 0.04% by mass aqueous potassium hydroxide solution at 23 ° C for 1 minute, and after development, it was air-dried with ultrapure water, and further post-baked at 230 ° C for 30 minutes. The film is hardened to form a permanent cured film. Next, the substrate on which the pixel was formed and the substrate on which only the ITO electrode was vapor-deposited into a predetermined shape were bonded together with a sealant in which 1.8 mm of glass beads were mixed, and then a liquid crystal (MLC6608) manufactured by Merck was injected to prepare a liquid crystal cell. Then, the liquid crystal cell was placed in a constant temperature layer at 60° C., and the voltage holding ratio of the liquid crystal cell was measured by a liquid crystal voltage retention ratio measurement system (VHR-1A type, manufactured by TOYO Corporation). The applied voltage at this time was a square wave of 5.5 V, and the measurement frequency was 60 Hz. Here, the voltage holding ratio is a value obtained by (a liquid crystal cell potential difference after 16.7 milliseconds / a voltage applied at 0 milliseconds). When the voltage holding ratio of the liquid crystal cell is 90% or less, the liquid crystal cell cannot hold the time of 16.7 milliseconds and the applied voltage at a predetermined level, and the liquid crystal cannot be sufficiently aligned, which may cause an "afterimage" of a residual image or the like. The results are shown in Table 1.

Examples 2 to 6 and Comparative Example 1

In the same manner as in Example 1, except that the type of the dye solution was changed as shown in Table 1, the colored compositions (CR2) to (CR7) were prepared.

Next, a liquid crystal cell was produced in the same manner as in Example 1, and the voltage holding ratio was measured. The results are shown in Table 1.

<Evaluation of chromaticity characteristics and contrast>

Example 7

13.5 parts by mass of the pigment dispersion liquid (a-1), 7.2 parts by mass of the dye solution (A-1), and 9.9 parts by mass of a binder resin (B1) solution as a binder resin, East Asia Synthetic Co., Ltd. as a crosslinking agent M-402 (a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate) 15.4 parts by mass of 2-benzyl-2-dimethylamino-1- as a photopolymerization initiator (4- L-phenylphenyl)butan-1-one (manufactured by Ciba Specialty Chemicals, trade name IRGACURE 369) 1.8 parts by mass, NCI-930 (made by Adeka Co., Ltd.) 0.1 part by weight, MEGAFAC F- as a fluorine-based surfactant 554 (manufactured by DIC Corporation) 0.2 parts by mass and ethyl lactate as a solvent were mixed to prepare a coloring composition (CR8) having a solid content concentration of 20% by mass.

The colored composition (CR8) was applied onto a glass substrate by a spin coater, and then prebaked in a hot plate at 80 ° C for 10 minutes to form a coating film. The number of rotations of the spin coater was changed, and after the same operation, three coating films having different film thicknesses were formed.

Next, after the substrates were cooled to room temperature, radiation of respective wavelengths of 365 nm, 405 nm, and 436 nm was exposed to each of the coating films at a exposure amount of 2000 J/m ² without using a high-pressure mercury lamp. Then, a developing solution of a 0.04 mass% potassium hydroxide aqueous solution at 23 ° C was sprayed onto the substrates at a developing pressure of 1 kgf/cm ² (nozzle diameter: 1 mm), and spray development was performed for 90 seconds. Then, the substrate was washed with ultrapure water, air-dried, and further baked in a clean oven at 230 ° C for 30 minutes to form a cured film for evaluation.

Evaluation of chromaticity characteristics

For the obtained three cured films, a color analyzer (MCPD2000 manufactured by Otsuka Electronics Co., Ltd.) was used, and the chromaticity coordinate value (x, y) and the stimulus value in the CIE color system were measured by a C light source and a 2 degree field of view ( Y). Further, the film thickness of the obtained cured film was measured using Alpha-Step IQ manufactured by KLA-Tencor. From the measurement results, the chromaticity coordinate value x, the stimulus value (Y), and the film thickness of the chromaticity coordinate value y = 0.080 were obtained. The evaluation results are shown in Table 2. Incidentally, it can be said that the larger the stimulation value (Y), the higher the brightness, and the thinner the film thickness, the greater the coloring power of the colorant.

Contrast evaluation

The substrate on which the cured film is formed is sandwiched between two polarizing plates, and the polarizing plate on the front side is rotated by a fluorescent lamp (wavelength range of 380 to 780 nm) from the back side, and is illuminated by a luminance meter LS-100 (Minolta) The system determines the maximum and minimum values of the transmitted light intensity. Next, for each of the cured films, a value obtained by removing the maximum value by the minimum value was used as a contrast ratio. From the measurement results, the contrast ratio of the chromaticity coordinate value y = 0.080 was obtained. The evaluation results are shown in Table 2.

Example 8 and Comparative Example 2

In the same manner as in Example 7, except that the type and amount of the pigment dispersion liquid and the dye solution were changed as shown in Table 2, coloring compositions (CR9) to (CR10) were prepared. Further, the obtained coloring compositions (CR9) to (CR10) were evaluated in the same manner as in Example 7. The evaluation results are shown in Table 2.

Claims (9)

A coloring composition comprising: (A) a coloring agent comprising a compound represented by the following formula (1), (B) a binder resin, and (C) a crosslinking agent, X ⁺ Z ^- (1) [formula ( 1), X ⁺ represents a methine chromophore, an azo chromophore, a diarylmethane chromophore, a quinone imine chromophore, an anthraquinone chromophore, an indigo Chromophore or A chromophore; Z ^- represents a conjugate base of an organic acid having a polymerizable unsaturated group and a halogen group]. The colored composition of claim 1, wherein the Z ^- is an anion represented by the following formula (1a-1), In the formula (1a-1), Y ¹ represents a group having a polymerizable unsaturated group; Y ² represents a halogen group or a halogenated hydrocarbon group which may have a linking group which contains a carbon atom, a hydrogen atom or a halogen atom Atom]. The colored composition of claim 2, wherein the Y ¹ is a chain organic group having a polymerizable unsaturated group. The colored composition of claim 1, wherein the Z ^- is an anion represented by any one of the following formula (1a-2) or formula (1a-3), [In the formula (1a-2), R ¹ represents a (meth)acryloyl group or an allyl group; and X ¹ represents -O- or -O-(R ² O) _q -(*), wherein R ² represents alkanediyl group having a carbon number 2 or 3, q represents an integer of 1 to 100, (*) represents a linking bond of X ^2; X ² represents a substituted or unsubstituted alkanediyl group; and the Y ² of formula (1a-1 Y ^{2 is} synonymous], [In Formula ^(1a-3), R 3 represents a hydrogen atom or a methyl group; X ³ represents a single bond or a substituted or unsubstituted alkoxy diyl; ² synonymous with the formula Y ² Y (1a-1) above]. The colored composition of claim ² , wherein the Y ² is a fluorine group or a fluorinated hydrocarbon group which may have a linking group, and the linking group contains a carbon atom, a hydrogen atom or an atom other than a halogen atom. The colored composition according to any one of claims 2 to 5, wherein the Y ² is a group represented by the following formula (1-1) or a group represented by the following formula (1-2), [In the formula (1-1), R ²³ represents a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, an alicyclic hydrocarbon group, an alkoxy group, a fluorinated alkoxy group, R ²⁴ COOR ²⁵ - or R ²⁴ COOR. ²⁵ CFH-, wherein R ²⁴ represents an alkyl group, an alicyclic hydrocarbon group, a heteroaryl group or a substituted or unsubstituted aryl group, R ²⁵ represents an alkanediyl group; n represents an integer of 0 or more; "*" represents a linkage] , [In the formula (1-2), R ¹⁸ to R ²² each independently represent a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group, a fluorinated alkyl group or an alkoxy group; "*" represents a linkage; wherein, R ¹⁸ ~ At least one of R ²² is a fluorine atom or a fluorinated alkyl group]. A color filter comprising a coloring layer containing a compound represented by the following formula (1): X ⁺ Z ^- (1) [In the formula (1), X ⁺ represents a cationic chromophore; Z ^- An anion represented by the following formula (1a-1), [In the formula (1a-1), Y ¹ represents a chain-like organic group having a polymerizable unsaturated group; and Y ² represents a halogen group or a halogenated hydrocarbon group which may have a linking group which contains a carbon atom, a hydrogen atom or a halogen-removing group. An atom other than an atom]. A display element comprising the color filter of item 7 of the patent application. A coloring agent represented by the following formula (1): X ⁺ Z ^- (1) [In the formula (1), X ⁺ represents a cationic chromophore; and Z ^- represents a formula (1a-1) represented by the following formula (1a-1) Anion], [In the formula (1a-1), Y ¹ represents a chain-like organic group having a polymerizable unsaturated group; and Y ² represents a halogen group or a halogenated hydrocarbon group which may have a linking group which contains a carbon atom, a hydrogen atom or a halogen-removing group. An atom other than an atom].