KR20170071435A - The compound, color composition, color filter and display device - Google Patents

Abstract

The present invention relates to a color filter having excellent solvent resistance, a display device including the same, and a compound and a coloring composition capable of providing them.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound, a coloring composition, a color filter,

The present invention relates to compounds and to coloring compositions comprising them.

BACKGROUND ART [0002] Coloring compositions are used in the production of color filters used in display devices such as liquid crystal displays, electroluminescence displays, and plasma displays. As such a coloring composition, a coloring composition containing a compound represented by the following formula is known.

 [Chemical Formula 1]

 (2)

WO2012 / 053211 Japanese Patent Application Laid-Open No. 2015-38201

The above-described compounds can not sufficiently satisfy the absorbance and the voltage holding ratio, and the color filter formed from the coloring composition containing the compound may not be able to sufficiently satisfy the solvent resistance.

Accordingly, in order to solve the above problems, the present invention aims to provide a compound having excellent absorbance and voltage retention, a coloring composition containing the compound, a color filter having excellent solvent resistance, and a display device.

In order to achieve the above object,

A compound represented by the formula (A-I).

(3)

[In the formula (A-I)

R ⁴¹ to R ⁴⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an aralkyl group having 7 to 30 carbon atoms and may have a substituent, substituent group which may have an aromatic hydrocarbon group and the aralkyl group is -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f may be, include groups wherein the saturated hydrocarbon in the saturated hydrocarbon group of 1 to 20 carbon atoms wherein May be substituted with a substituted or unsubstituted amino group or a halogen atom, and when the number of carbon atoms in the saturated hydrocarbon group is 2 to 20, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or -CO- . However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, the adjacent methylene group is not simultaneously substituted with an oxygen atom, and the terminal methylene group is not substituted with an oxygen atom or -CO-. R ⁴¹ and R ⁴² may bond to form a ring together with the nitrogen atom to which they are bonded, and R ⁴³ and R ⁴⁴ may bond to form a ring together with the nitrogen atom to which they are attached.

R ⁴⁷ ~ R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy _{^{group, -SO 3 -, -SO 2 -N}} - -SO 2 -R f , or an alkyl group having 1 to 8 carbon atoms, the alkyl group The constituting methylene group may be substituted with an oxygen atom or -CO-, and R ⁴⁸ and R ⁵² may combine with each other to form -NH-, -S- or -SO ₂ -. However, adjacent methylene groups in the alkyl group are not simultaneously substituted with oxygen atoms, and the terminal methylene group is not substituted with an oxygen atom or -CO-.

The ring T ¹ represents an aromatic heterocycle having 3 to 10 carbon atoms, and the aromatic heterocycle has a saturated hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted amino group, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent . Substituent group which may have the aromatic hydrocarbon is -SO ₃ ^- can be a -SO ₂ -R ^{f -} or -SO ₂ -N.

M ^{r +} represents a hydrogen ion, a metal ion of r, or a substituted or unsubstituted ammonium ion.

k is a -SO ₃ with a compound represented by formula (AI) ^- represents the sum of the number of -SO ₂ -R ^{f -,} and -SO ₂ -N number of.

r represents an integer of 1 or more.

R ^f represents a fluoroalkyl group having 1 to 12 carbon atoms.

However, the compound represented by formula (AI) is -SO ₂ -N ^- -SO ₂ has at least one of -R ^f].

In one embodiment of the present invention, the compound wherein M < ^r > ⁺ is an r-metal ion may be used.

In one embodiment of the present invention, the aromatic heterocycle represented by T ¹ may be a compound represented by the following formula (A-t1).

[Chemical Formula 4]

[In the formula (A-t1)

The ring T ² represents an aromatic heterocycle having 3 to 10 carbon atoms.

R ⁴⁵ and R ⁴⁶ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 7 to 30 carbon atoms And when the number of carbon atoms in the saturated hydrocarbon group is 2 to 20, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or -CO-. However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, the adjacent methylene group is not simultaneously substituted with an oxygen atom, and the terminal methylene group is not substituted with an oxygen atom or -CO-. R ⁴⁵ and R ⁴⁶ may combine to form a ring together with the nitrogen atom to which they are attached.

R ⁵⁵ represents a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms and may have a substituent.

k1 represents 0 or 1;

* Represents the bonding position with the carbanion.]

The present invention also provides a coloring composition comprising the compound of the present invention.

The present invention also provides a color filter formed from the coloring composition.

Further, the present invention provides a display device including the color filter.

The compound of the present invention is excellent in absorbance and voltage retention, and the coloring composition containing the compound can form a color filter excellent in solvent resistance.

The compounds of the present invention are represented by the formula (A-I). Hereinafter, the compound represented by the formula (A-I) is also referred to as the compound (A-I). The compounds of the present invention also include tautomers or salts thereof.

 [Chemical Formula 5]

 [In the formula (A-I)

R ⁴¹ to R ⁴⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an aralkyl group having 7 to 30 carbon atoms and may have a substituent, substituent group which may have an aromatic hydrocarbon group and the aralkyl group is -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f may be, include groups wherein the saturated hydrocarbon in the saturated hydrocarbon group of 1 to 20 carbon atoms wherein May be substituted with a substituted or unsubstituted amino group or a halogen atom, and when the number of carbon atoms in the saturated hydrocarbon group is 2 to 20, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or -CO- . However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, the adjacent methylene group is not simultaneously substituted with an oxygen atom, and the terminal methylene group is not substituted with an oxygen atom or -CO-. R ⁴¹ and R ⁴² may bond to form a ring together with the nitrogen atom to which they are bonded, and R ⁴³ and R ⁴⁴ may bond to form a ring together with the nitrogen atom to which they are attached.

R ⁴⁷ ~ R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy _{^{group, -SO 3 -, -SO 2 -N}} - -SO 2 -R f , or an alkyl group having 1 to 8 carbon atoms, the alkyl group The constituting methylene group may be substituted with an oxygen atom or -CO-, and R ⁴⁸ and R ⁵² may combine with each other to form -NH-, -S- or -SO ₂ -. However, adjacent methylene groups in the alkyl group are not simultaneously substituted with oxygen atoms, and the terminal methylene group is not substituted with an oxygen atom or -CO-.

The ring T ¹ represents an aromatic heterocycle having 3 to 10 carbon atoms and the aromatic heterocycle may have a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms and may have a substituent. Substituent group which may have the aromatic hydrocarbon is -SO ₃ ^- can be a -SO ₂ -R ^{f -} or -SO ₂ -N.

M ^{r +} represents a hydrogen ion, a metal ion of r, or a substituted or unsubstituted ammonium ion.

k is a -SO ₃ with a compound represented by formula (AI) ^- represents the sum of the number of -SO ₂ -R ^{f -,} and -SO ₂ -N number of.

r represents an integer of 1 or more.

R ^f represents a fluoroalkyl group having 1 to 12 carbon atoms.

However, the compound represented by formula (AI) is -SO ₂ -N ^- -SO ₂ has at least one of -R ^f].

The aromatic heterocycle represented by ring T ¹ may be monocyclic or condensed. The number of carbon atoms of the aromatic heterocycle represented by ring T ¹ is 3 to 10, preferably 3 to 8. The aromatic heterocycle is preferably a 5- to 10-membered ring, more preferably a 5- to 9-membered ring. Examples of the monocyclic aromatic heterocycle include a 5-membered ring containing nitrogen atom such as pyrrole ring, oxazole ring, pyrazole ring, imidazole ring, thiazole ring and the like; A 5-membered ring which does not contain a nitrogen atom such as a furan ring or a thiophene ring; A 6-membered ring containing a nitrogen atom such as a pyridine ring, a pyrimidine ring, a pyridazine ring, or a pyrazine ring; The aromatic heterocycle of the condensed ring may be a condensed ring containing a nitrogen atom such as an indole ring, a benzimidazole ring, a benzothiazole ring or a quinoline ring; A condensed ring containing no nitrogen atom such as benzofuran ring; And the like.

Examples of the substituent that the aromatic heterocycle of ring T ¹ may have include a halogen atom, a cyano group, a saturated hydrocarbon group having 1 to 20 carbon atoms (preferably an alkyl group having 1 to 20 carbon atoms), a substituted or unsubstituted amino group (Preferably an alkyl group having 1 to 20 carbon atoms), a substituted or unsubstituted amino group or a substituent group, and the like, and an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, And an aromatic hydrocarbon group having 6 to 20 carbon atoms.

Among them, the aromatic heterocycle of ring T ¹ is preferably an aromatic heterocycle containing a nitrogen atom, and more preferably a five-membered aromatic heterocycle containing a nitrogen atom.

It is more preferable that the ring T ¹ is a ring represented by the formula (A-t1).

 [Chemical Formula 6]

 [In the formula (A-t1)

The ring T ² represents an aromatic heterocycle having 3 to 10 carbon atoms.

R ⁴⁵ and R ⁴⁶ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 7 to 30 carbon atoms And when the number of carbon atoms in the saturated hydrocarbon group is 2 to 20, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or -CO-. However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, the adjacent methylene group is not simultaneously substituted with an oxygen atom, and the terminal methylene group is not substituted with an oxygen atom or -CO-. R ⁴⁵ and R ⁴⁶ may combine to form a ring together with the nitrogen atom to which they are attached.

R ⁵⁵ represents a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms and may have a substituent.

k1 represents 0 or 1;

* Represents the bonding position with the carbanion.]

The aromatic heterocycle of ring T ² is the same ring as the aromatic heterocycle shown for ring T ¹ .

Furthermore, the ring T ¹ is particularly preferably a ring represented by the formula (A-t1-1).

 (7)

 [In the formula (A-t1-1)

R ⁵⁶ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms and may have a substituent.

X2 represents an oxygen atom, -N (R < ⁵⁷ >) - or a sulfur atom.

R ⁵⁷ represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.

R ⁴⁵ and R ⁴⁶ are as defined above.

* Represents the bonding position with the carbanion.]

Also, the ring T ¹ is preferably a ring represented by the formula (A-t2).

 [Chemical Formula 8]

 [In the formula (A-t2)

The ring T ³ represents an aromatic heterocycle having 3 to 10 carbon atoms having a nitrogen atom.

R ⁵⁸ is an aromatic hydrocarbon group, -SO ₃ of 6 to 20 carbon atoms which may have a saturated hydrocarbon group, a substituent having 1 to 20 carbon atoms ^- represents an -SO ₂ -R ^{f -} or -SO ₂ -N.

R ⁵⁹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent.

k2 represents 0 or 1;

* Represents the bonding position with the carbanion.]

The ring T ¹ is more preferably a ring represented by the formula (A-t2-1).

 [Chemical Formula 9]

 [In the formula (A-t2-1)

R ⁶⁰ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms and may have a substituent.

R ⁶¹ is a hydrogen atom, -SO ₃ ^- represents an -SO ₂ -R ^{f -} or -SO ₂ -N.

R ⁵⁹ has the same meaning as above.

* Represents the bonding position with the carbanion.]

The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ may be any of linear, branched and cyclic. Examples of the linear or branched saturated hydrocarbon group include linear or branched saturated hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, A chain alkyl group; And branched chain alkyl groups such as an isopropyl group, an isobutyl group, an isopentyl group, a neopentyl group and a 2-ethylhexyl group. The number of carbon atoms of the saturated hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 6.

The cyclic saturated hydrocarbon group represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ may be monocyclic or polycyclic. Examples of the cyclic saturated hydrocarbon group include an alicyclic saturated hydrocarbon group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and an adamantyl group. The carbon number of the cyclic saturated hydrocarbon group is preferably 3 to 10, more preferably 6 to 10.

Specific examples of the saturated hydrocarbon groups represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ include groups represented by the following formulas. In the following formulas, * represents a bonding position.

 [Chemical formula 10]

The saturated hydrocarbon group represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ may be substituted with a substituted or unsubstituted amino group or a halogen atom. Examples of the substituted amino group include alkylamino groups such as dimethylamino group and diethylamino group. Examples of the halogen atom include fluorine, chlorine, bromine and iodine. When the halogen atom is a fluorine atom, the saturated hydrocarbon group substituted with a halogen atom (fluorine atom) represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ is a trifluoromethyl group, a pentafluoroethyl group, And a perfluoroalkyl group such as a fluoropropyl group.

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms having a substituent include groups represented by the following formulas. In the following formulas, * represents a bonding position with a nitrogen atom or the like.

 (11)

Examples of the alkyl group having 1 to 8 carbon atoms represented by R ⁴⁷ to R ⁵⁴ include a group having 1 to 8 carbon atoms in the straight chain or branched chain saturated hydrocarbon group exemplified as the saturated hydrocarbon group represented by R ⁴¹ .

Examples of the alkyl group having 1 to 10 carbon atoms represented by R ⁵⁷ include a group having 1 to 10 carbon atoms in the straight chain or branched chain saturated hydrocarbon group exemplified as the saturated hydrocarbon group represented by R ⁴¹ .

When the number of carbon atoms of the saturated hydrocarbon group represented by R ⁴¹ to R ⁴⁶ is 2 to 20, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or -CO-. However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, the adjacent methylene group is not simultaneously substituted with an oxygen atom, and the terminal methylene group is not substituted with an oxygen atom or -CO-. In this case, the saturated hydrocarbon group is preferably a linear or branched saturated hydrocarbon group (that is, a linear or branched alkyl group), and more preferably a linear saturated hydrocarbon group (that is, a linear alkyl group). The saturated hydrocarbon group in which the methylene group may be substituted with an oxygen atom or -CO- preferably has 2 to 10 carbon atoms, more preferably 2 to 8 carbon atoms. When the methylene group is substituted with an oxygen atom or -CO-, the number of carbon atoms between the terminal and the oxygen atom or -CO-, or between the oxygen atom or -CO- and the oxygen atom or -CO- is 1 or more, preferably 1 To 5, more preferably 2 to 3, and still more preferably 2. Examples of the group in which the methylene group of the saturated hydrocarbon group is substituted with an oxygen atom or -CO- include an alkoxyalkyl group; A polyalkoxyalkyl group such as an (alkoxyalkoxy) alkyl group, an (alkoxyalkoxyalkoxy) alkyl group, an (alkoxyalkoxyalkoxyalkoxy) alkyl group, an (alkoxyalkoxyalkoxyalkoxy) alkyl group and an (alkoxyalkoxyalkoxyalkoxyalkoxy) The number of repeating alkoxy units is, for example, 1 to 6, preferably 1 to 4, more preferably 1 to 2. A more preferred specific example is a group represented by the following formula. In the following formulas, * represents a bonding position with a nitrogen atom.

 [Chemical Formula 12]

The number of carbon atoms of the aromatic hydrocarbon group which may have a substituent represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ is preferably 6 to 20, more preferably 6 to 15, still more preferably 6 ~ 12. Examples of the aromatic hydrocarbon group include a phenyl group, a tolyl group, a xylyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, and a terphenyl group, preferably a phenyl group, a naphthyl group, a tolyl group, , And particularly preferably a phenyl group. The aromatic hydrocarbon group may have one or two or more substituents. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom and a bromine atom; A haloalkyl group having 1 to 6 carbon atoms such as a chloromethyl group and a trifluoromethyl group; An alkoxy group having 1 to 6 carbon atoms such as methoxy group and ethoxy group; A hydroxy group; A sulfamoyl group; An alkylsulfonyl group having 1 to 6 carbon atoms such as a methylsulfonyl group; An alkoxycarbonyl group having 1 to 6 carbon atoms such as a methoxycarbonyl group and an ethoxycarbonyl group; -SO ₃ ^{-; _{-SO 2 -N - -SO 2 -R f}} ; And the like, -SO ₃ ^- can be a -SO ₂ -R ^{f -} or -SO ₂ -N. However, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f is one that is directly bonded to the aromatic hydrocarbon ring of the aromatic hydrocarbon group, or it is preferable that the substitution of hydrogen atoms bonded to the aromatic hydrocarbon ring .

Specific examples of the aromatic hydrocarbon group which may have a substituent include groups represented by the following formulas. In the following formulas, * represents a bonding position with a nitrogen atom.

[Chemical Formula 13]

 [Chemical Formula 14]

Examples of the aralkyl group which may have a substituent represented by R ⁴¹ to R ⁴⁶ and R ⁵⁹ include an aralkyl group having 1 to 10 carbon atoms (preferably 1 to 5 carbon atoms) such as a methylene group, an ethylene group and a propylene group in the group described as the aromatic hydrocarbon group A group in which a quadriyl group is bonded, and the like. The number of carbon atoms of the aralkyl group is preferably 7 to 30, more preferably 7 to 20, and still more preferably 7 to 17 carbon atoms.

A ring formed by combining R ⁴¹ and R ⁴² together with a nitrogen atom to which they are bonded, a ring formed by bonding R ⁴³ and R ⁴⁴ together with a nitrogen atom to which they are bonded, and R ⁴⁵ and R ⁴⁶ are bonded to form Include a nitrogen-containing nonaromatic 4- to 7-membered ring such as a pyrrolidine ring, a morpholine ring, a piperidine ring, a piperazine ring and the like, preferably a pyrrolidine ring, piperidine ring, And a 4- to 7-membered ring having only one nitrogen atom as a hetero atom such as a pyran ring.

R ⁵⁸ is preferably a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms and may have a substituent.

Among them, R ⁴¹ to R ⁴⁴ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ are preferably a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having optionally a substituent, More preferably a hydrocarbon group or an aromatic hydrocarbon group represented by the following formula. R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ are more preferably aromatic hydrocarbon groups represented by the following formulas. In the following formulas, * represents a bonding position with a nitrogen atom.

 [Chemical Formula 15]

 [Chemical Formula 16]

R ⁴⁵ to R ⁴⁶ each independently represent a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group in which a methylene group constituting an alkyl group having 2 to 20 carbon atoms is substituted with an oxygen atom or -CO-, Or R ⁴⁵ and R ⁴⁶ are bonded to form a ring with the nitrogen atom to which they are bonded. R ⁴⁵ to R ⁴⁶ each independently represent a saturated hydrocarbon group having 1 to 8 carbon atoms, an alkoxyalkyl group, or an aromatic hydrocarbon group represented by the following formula, or R ⁴⁵ and R ⁴⁶ are bonded to each other to form a 4 And more preferably each independently a saturated hydrocarbon group having 1 to 8 carbon atoms, an alkoxyalkyl group, or an aromatic hydrocarbon group represented by the following formula. In the following formulas, * represents a bonding position with a nitrogen atom.

 [Chemical Formula 17]

 [Chemical Formula 18]

Examples of the alkyl group having 1 to 8 carbon atoms represented by R ⁴⁷ to R ⁵⁴ include a group having 1 to 8 carbon atoms in the straight chain or branched chain saturated hydrocarbon group exemplified as the saturated hydrocarbon group represented by R ⁴¹ . A group in which the methylene group constituting the alkyl group having 2 to 8 carbon atoms represented by R ⁴⁷ to R ⁵⁴ is substituted with an oxygen atom or -CO- (provided that the adjacent methylene group in the alkyl group is not substituted with an oxygen atom at the same time, Group is not substituted with oxygen atom or -CO-), the group in which the methylene group constituting the alkyl group having 2 to 20 carbon atoms represented by R ⁴¹ to R ⁴⁶ is substituted with oxygen atom or -CO- has 8 or less carbon atoms The selected group can be named. The alkyl group having 1 to 8 carbon atoms represented by R ⁴⁷ to R ⁵⁴ is more preferably a group represented by the following formula: In the following formulas, * represents a bonding position with a carbon atom.

 [Chemical Formula 19]

From the viewpoint of ease of synthesis, each of R ⁴⁷ to R ⁵⁴ is preferably a hydrogen atom, a halogen atom or an alkyl group having 1 to 8 carbon atoms, and each independently is preferably a hydrogen atom, a methyl group, a fluorine atom or a chlorine atom .

As R ^{57, a} hydrogen atom or an alkyl group having 1 to 5 carbon atoms is preferable.

R ⁶¹ is preferably a hydrogen atom.

The r-valent metal ion represented by M ^{r +} is an alkali metal ion such as lithium ion, sodium ion or potassium ion; Alkaline earth metal ions such as beryllium ion, magnesium ion, calcium ion, strontium ion and barium ion; Transition metal ions such as titanium ion, zirconium ion, chromium ion, manganese ion, iron ion, cobalt ion, nickel ion and copper ion; And typical metal ions such as zinc ion, cadmium ion, aluminum ion, indium ion, tin ion, lead ion and bismuth ion. r is 1 or more, preferably 2 or more, preferably 5 or less, more preferably 4 or less, still more preferably 3 or less. ^Examples of the substituted or unsubstituted ammonium ion represented by M ^{r +} include a quaternary ammonium ion such as tetraalkylammonium ion.

From the viewpoint of the voltage holding ratio, the metal ion of r is preferable, and the alkaline earth metal ion, the typical metal ion and the like are more preferable as M ^{r +} , and the magnesium ion, barium ion and zinc ion are more preferable. From the standpoint of absorbance, M ^{r +} is preferably a hydrogen ion or an alkali metal ion, more preferably a hydrogen ion.

The number of M ^{r +} in the formula (AI) is one less than the sum (k) of the number of -SO ₃ ^{- and} the number of -SO ₂ -N ^- -SO ₂ -R ^f in the compound represented by the formula (AI) . Thus, the compound (AI) has a valence of 0, that is, an electrically neutral compound. -SO ₃ ^- , the number of -SO ₃ ^- is preferably 6 or less, more preferably 3 or less, and may be 1 or more. It is also preferable that the number of -SO ₃ ^- is zero.

Examples of the fluoroalkyl group having 1 to 12 carbon atoms represented by R ^f include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group (perfluoromethyl group), a monofluoroethyl group, a difluoroethyl group, a trifluoroethyl group, (Perfluoroethyl group), a monofluoropropyl group, a difluoropropyl group, a trifluoropropyl group, a tetrafluoropropyl group, a pentafluoropropyl group, a hexafluoropropyl group, a tetrafluoroethyl group, (Perfluoropropyl) group, a monofluorobutyl group, a difluorobutyl group, a trifluoropropyl group, a tetrafluorobutyl group, a pentafluorobutyl group, a hexafluorobutyl group , A heptafluorobutyl group, an octafluorobutyl group, and a nonafluorobutyl group (perfluorobutyl group). Among them, a perfluoroalkyl group is preferable as the alkyl group (fluoroalkyl group) in which all or part of hydrogen atoms represented by R ^f are substituted with fluorine atoms. The alkyl group (fluoroalkyl group) in which all or a part of the hydrogen atoms represented by R ^f are substituted with fluorine atoms preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, still more preferably 1 to 3 carbon atoms.

Compound (AI) is -SO ₂ -N ^- -SO ₂ -R ^f has one of the least. -SO ₂ -N ^- -SO ₂ -R ^f is a number of at least 1, preferably 1-7, and more preferably 1 to 4, more preferably 1 or 2, particularly preferably 2.

This Compound (AI) is -SO ₂ -N ^- -SO ₂ -R ^f the gatdoe -SO ₃ ^- and preferably also does not have a, -SO ₂ -N ^- having ^- -SO ₂ -R ^f -SO ₃ and . -SO ₂ -N ^- if having the compound (AI) is ^{_{-SO 2 -N - - -SO 2 -R}} f , and -SO ₃ and the -SO ₂ -R ^f contains at least one, -SO ₂ - The total number of N ^- -SO ₂ -R ^f and -SO ₃ ^- is preferably 2 to 7, more preferably 2 to 4, still more preferably 2.

The -SO ₂ -N ^- -SO ₂ -R ^f, or -SO ₃ ^- is an aromatic hydrocarbon group of said R ⁴⁷ ~ R ⁵⁴ either includes or as in, R ⁴¹ ~ R 6 to 20 carbon atoms which may have a substituent represented by ⁴⁴ , An aralkyl group having 7 to 30 carbon atoms which may have a substituent represented by R ⁴¹ to R ⁴⁴ and an aromatic hydrocarbon group having 6 to 20 carbon atoms which substitutes a hydrogen atom of an aromatic heterocyclic ring represented by T ¹ are preferred, and are more preferably R ⁴¹ ~ R ⁴⁴ aromatic hydrocarbon group of 6 to 20 carbon atoms which may have a substituent, and may have a substituent represented by R ⁴¹ ~ R ⁴⁴ bonded to the aralkyl group of a carbon number of 7 to 30 which appear in aromatic hydrocarbon rings in, more preferably R ⁴¹ ~ aromatic hydrocarbon group of 6 to 20 carbon atoms which may have a substituent represented by R ^44, R ⁴¹ ~ R ⁴⁴ having a carbon number of 7 to 30 which may have a substituent represented by an aralkyl group ( Benzene ring) And coupled to the para position in combination with the position of the chair.

However, aromatic hydrocarbon group or an aralkyl groups -SO ₂ -N ^- If you are a ^{_{bond, -SO 2 -N - - -SO 2}} -R f -SO ₂ -R ^f or ₃ or -SO -SO ₃ ^- is an aromatic It is preferably bonded directly to an aromatic hydrocarbon ring of a hydrocarbon group or an aralkyl group. That is -SO ₂ -N ^- -SO ₂ -R ^f, or -SO ₃ ^- is preferable that the substitution of hydrogen atoms bonded to the aromatic hydrocarbon ring.

-SO ₂ -N ^- -SO ₂ -R ^f, and -SO ₃ ^- can also be bonded to the same aromatic hydrocarbon ring, but preferably bonded to other aromatic hydrocarbon rings.

It is preferable that the compound (A-I) does not have an ethylenic unsaturated bond.

A compound having a ^- -SO ₂ -R ^f gatdoe the -SO ₃ ^{- -} having no compound _{^{and, -SO 2 -N - -SO 2 -R}} f -SO ₃ and the compound (AI) -SO ₂ -N as It is also preferable to use them in combination. In this _{^{case, -SO 2 -N - -SO 2 -R}} f gatdoe the -SO ₃ ^- having no compound _{^{and, -SO 2 -N - -SO 2 -R}} f , and -SO ₃ ^- and having a molar ratio of compound _{^{(-SO 2 -N - -SO 2 -SO}} 3 gatdoe the -R ^{f -} compound having no _{^{/ -SO 2 -N - -SO 2 -R}} f , and -SO ₃ ^- compound having a) is preferably not less than 0.01 More preferably not less than 0.05, more preferably not less than 0.1, and not more than 50, more preferably not more than 10, still more preferably not more than 5, particularly preferably not more than 1. [

The compound (A-I) is preferably a compound represented by the following formula (A-I1).

[Chemical Formula 20]

[In the formula (A-I1)

R ⁸¹ ~ R ⁹⁰ each independently represent a hydrogen atom, saturated hydrocarbon group of 1 to 20 carbon atoms, a halogen atom, -SO ₃ ^- represents an -SO ₂ -R ^{f -} or -SO ₂ -N.

k1 is a -SO ₃ with a compound represented by the formula (A-I1) ^- represents the sum of the number of -SO ₂ -R ^{f -,} and -SO ₂ -N number of.

R ⁴¹ , R ⁴³ , R ⁴⁷ to R ⁵⁴ , T ¹ , M ^{r +} , r and R ^f are as defined above.

However, the compound of formula (A-I1) is -SO ₂ -N ^- -SO ₂ has at least one of -R ^f].

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ⁸¹ to R ⁹⁰ include the same groups as those exemplified as the saturated hydrocarbon group represented by R ⁴¹ . R ⁸¹ ~ R ⁹⁰ is a saturated hydrocarbon group of hydrogen, carbon number 1 ~ 8, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f is preferably a hydrogen atom, -SO ₃ ^- or -SO -N ₂ ^- is more preferred _{^{-SO 2 -R f - -SO 2 -R}} f is more preferred, and hydrogen atom or a -SO ₂ -N.

In addition, -SO ₂ -N ^- -SO ₂ -R ^f, or -SO ₃ ^- is (e) or included as one of the ^{R 47 ~ R 54, (f} ) R 81 ~ R or included as one of ^90, (g (F), (g), (g) and (g) are preferably bonded to an aromatic hydrocarbon having 6 to 20 carbon atoms substituting the hydrogen atom of the aromatic heterocycle represented by T ¹ , ) Or a combination of (f) to (g), and more preferably exists as (f). Also, among R ⁸¹ to R ⁹⁰ , it is preferably at least one selected from R ⁸⁶ and R ⁸⁹ .

-SO ₂ -N contained in the compound (A-I1) ^- number of -SO ₂ -R ^f is preferably 1-7, and more preferably 1 to 4, more preferably 1 or 2; In addition, compound (A-I1) is -SO ₂ -N ^- if having the compound (A-I1) is ^{_{-SO 2 -N - - -SO 2 -R}} f , and -SO ₃ -SO ₂ -R ^f is at least and it contains ^{_{one, -SO 2 -N - -SO 2 -R}} f , and -SO ₃ ^- the number (k1) of the sum of is preferably 2-7, and more preferably 2 to 4, more preferably 2 to be.

Having a ^- -SO ₂ -R ^f gatdoe the -SO ₃ ^{- -} having no compound _{^{and, -SO 2 -N - -SO 2 -R}} f -SO ₃ and -SO ₂ -N compound as (A-I1) It is also preferable to use a compound in combination. In this _{^{case, -SO 2 -N - -SO 2 -R}} f gatdoe the -SO ₃ ^- having no compound _{^{and, -SO 2 -N - -SO 2 -R}} f , and -SO ₃ ^- and having a molar ratio of compound _{^{(-SO 2 -N - -SO 2 -SO}} 3 gatdoe the -R ^{f -} compound having no _{^{/ -SO 2 -N - -SO 2 -R}} f , and -SO ₃ ^- compound having a) is preferably not less than 0.01 More preferably not less than 0.05, more preferably not less than 0.1, and not more than 50, more preferably not more than 10, still more preferably not more than 5, particularly preferably not more than 1. [

Examples of the compound (A-I) include the compounds (A-I-1) to (A-I-632) represented by the formula (A-I-I) as shown in Tables 1 to 12 below. In the table, * indicates the bonding position.

However, formula (AII) is a compound represented by -SO ₂ -N ^- -SO ₂ -CF ₃ to 2 gae have ^{_{or, -SO 2 -N - -SO 2 -CF}} 3 and one of -SO ₃ ^- 1 one has, and the -SO ₂ -N ^- -SO ₂ -CF ₃ or -SO ₃ ^-, or is included as one of R ^h, and bonded to an aromatic hydrocarbon ring (benzene ring) of the aromatic hydrocarbon groups represented by Ph1 ~ Ph12 and, it is preferably bonded to the para position on the bonding position of R ⁴¹ ~ R ⁴⁴ aromatic hydrocarbon ring (benzene ring) of the aromatic hydrocarbon groups represented by Ph1 ~ Ph12 in.

 [Chemical Formula 21]

In Table 1 to 12, Me represents methyl group, Et represents ethyl group, iPr represents isopropyl group, Bt represents n-butyl group, EOE represents ethoxyethyl group, and 14Bt represents butane-1,4-diyl group, Ph1 to Ph12 represent ≪ / RTI > In the formulas, * represents a bonding position.

 [Chemical Formula 22]

Examples of the compound (A-I) include the compounds (A-I-634) to (A-I-657) represented by the formula (A-I-II) as shown in the following Table 13. In the table, * indicates the bonding position.

However, the compound represented by formula (AI-II) is -SO ₂ -N ^- -SO ₂ -CF _3, and -SO and ₂ -NH-SO ₂ -CF have one by one to _three, the -SO ₂ -N ^- -SO ₂ -CF _3, and -SO ₂ -NH-SO ₂ -CF ₃ or is included as one of R ^h, bonded to an aromatic hydrocarbon ring (benzene ring) of the aromatic hydrocarbon group represented by any one of Ph1, Ph13, Ph14, and have.

(23)

In Table 13, Me represents methyl group, Et represents ethyl group, iPr represents isopropyl group, Bt represents n-butyl group, EOE represents ethoxyethyl group, Hex represents n-hexyl group, Ph1, Ph13 and Ph14 represent the following formula Quot;

In the formulas, * represents a bonding position.

 ≪ EMI ID =

The compound (A-I) can be also used by mixing a compound represented by the following formula (A-III) (hereinafter also referred to as a compound (A-III)).

 (25)

 [In the formula (A-III)

R ^21a to R ^24a each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an aralkyl group having 7 to 30 carbon atoms and may have a substituent, The substituent that the aromatic hydrocarbon group and the aralkyl group may have may be -SO ₃ ^{-. In} the saturated hydrocarbon group having 1 to 20 carbon atoms, the hydrogen atom contained in the saturated hydrocarbon group may be a substituted or unsubstituted amino group or a halogen atom And when the saturated hydrocarbon group having 1 to 20 carbon atoms is an alkyl group having 2 to 20 carbon atoms, the methylene group contained in the alkyl group may be substituted with an oxygen atom or -CO-. However, in the alkyl group having 2 to 20 carbon atoms, the adjacent methylene group is not simultaneously substituted with an oxygen atom, and the terminal methylene group is not substituted with an oxygen atom or -CO-. R ^21a and R ^22a may bond to form a ring together with the nitrogen atom to which they are bonded, and R ^23a and R ^24a may bond to form a ring together with the nitrogen atom to which they are attached.

R ^27a to R ^34a each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, -SO ₃ ^- or an alkyl group having 1 to 8 carbon atoms, and the methylene group constituting the alkyl group is substituted with an oxygen atom or -CO- . R ^28a and R ^32a may combine with each other to form -NH-, -S- or -SO ₂ -.

The ring T ¹⁰ represents an aromatic heterocycle having 3 to 10 carbon atoms and the aromatic heterocycle may have a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms and may have a substituent. The substituent that the aromatic hydrocarbon group may have may be -SO ₃ ^- .

M ^{r +} and r have the same meanings as above.

k2 is a -SO ₃ with a compound represented by the formula (A-III) ^- indicates the number of.

However, the compound represented by the formula (A-III) has at least one -SO ₃ ^- .

The saturated hydrocarbon group, aromatic hydrocarbon group and aralkyl group represented by R ^21a to R ^24a are the same groups as the saturated hydrocarbon group, aromatic hydrocarbon group and aralkyl group represented by R ⁴¹ to R ⁴⁴ , respectively.

^Examples of the alkyl group represented by R ^27a to R ^34a include the same groups as those represented by R ⁴⁷ to R ⁵⁴ .

It is preferable that the compound (A-III) has at least one -SO ₃ ^- . More specifically, -SO ₃ ^- may include any of R ^27a to R ^34a (a ' Is bonded to an aromatic hydrocarbon having 6 to 20 carbon atoms which may have a substituent represented by R ^21a to R ^24a or is bonded to an aralkyl group having 7 to 30 carbon atoms which may have a substituent represented by (c ') R ^21a to R ^24a Or an aromatic hydrocarbon group having 6 to 20 carbon atoms substituting the hydrogen atom of the aromatic heterocycle represented by (d ') T ³ , or a combination of these (a') to (d) , (b '), (c'), (d ') or a combination of these (b') to (d '). The number of -SO ₃ ^- is preferably 0 to 6, more preferably 1 to 6, still more preferably 1 to 3.

-SO ₃ ^- may be bonded to the same aromatic hydrocarbon ring, but is preferably bonded to another aromatic hydrocarbon ring.

When the compound (AI) and the compound (A-III) are mixed, the content of the compound (A-III) is preferably 1 mol or more, more preferably 20 mol or more, More preferably 40 mol or more, and is preferably 90 mol or less, more preferably 80 mol or less, and still more preferably 70 mol or less.

The compound (AI) can be prepared by, for example, sulfonating a compound represented by the formula (A-IV) (hereinafter referred to as a compound (A-IV) ) ≪ / RTI > The compound (AI) may be reacted with a halide (preferably a chloride), an acetate salt, a phosphate, a sulfate, a silicate, a cyanide or the like containing an ^r- metal ion M ^{r +} if necessary. The compound (A-IV) is preferably a hydrochloride salt, a phosphate salt, a perchlorate salt, a BF ₄ salt, a PF ₆ salt or the like.

 (26)

 [In the formula (A-IV)

R ^1a to R ^4a each independently represent a substituted or unsubstituted amino group or a saturated hydrocarbon group having 1 to 20 carbon atoms and an alkyl group having 2 to 20 carbon atoms which may be substituted with a halogen atom, wherein the methylene group constituting the alkyl group is an oxygen atom or - CO-, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, an aralkyl group having 7 to 30 carbon atoms which may have a substituent, or a hydrogen atom. R ^1a and R ^2a may bond to form a ring together with the nitrogen atom to which they are bonded, and R ^3a and R ^4a may bond to form a ring together with the nitrogen atom to which they are attached.

R ^7a to R ^14a each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group or an alkyl group having 1 to 8 carbon atoms, and the methylene group constituting the alkyl group may be substituted with an oxygen atom or -CO-. R ^8a and R ^12a may combine with each other to form -NH-, -S- or -SO ₂ -.

The ring T ¹¹ represents an aromatic heterocycle having 3 to 10 carbon atoms and the aromatic heterocycle may have a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms and may have a substituent.

M ¹ represents Cl ^- , phosphate ion, perchlorate ion, BF ₄ ^- or PF ₆ ^- .

In the formula (A-III), R ^21a to R ^24a , R ^27a to R ^34a , ring T ¹⁰ , M ^{r +} , r and k2 have the same meanings as above.

However, the compound represented by the formula (A-III) has at least one -SO ₃ ^- .

[In formula (A-II), R ^f has the same meaning as above.]

[In formula (AI), R ⁴¹ to R ⁴⁴ , R ⁴⁷ to R ⁵⁴ , ring T ¹ , k, M ^{r +} and r have the same meanings as above.]

The sulfonation can be carried out by various known methods, for example, Journal of Organic Chemistry, (1994), vol. 59, # 11, p. 3232-3236.

The compound (A-I) of the present invention can be applied to a fiber product, for example, by doughing, impregnating or attaching it to a fiber material.

The coloring composition of the present invention comprises a colorant (A), and the colorant (A) comprises a compound (A-I). The coloring composition of the present invention preferably further contains a solvent (E), and more preferably a resin (B), a polymerizable compound (C) and a polymerization initiator (D). (D1) and a leveling agent (F).

Hereinafter, the coloring composition containing the resin (B), the polymerizable compound (C) and the polymerization initiator (D) may be referred to as a colored curable resin composition.

The compounds exemplified as the respective components in the present specification may be used alone or in combination of several kinds unless otherwise specified.

Solvent (E)

The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used. For example, an ester solvent (a solvent containing -COO- in the molecule but not containing -O-), an ether solvent (a solvent containing -O- in the molecule but not containing -COO-), an ether ester solvent (Solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule but not containing -COO-), alcohol solvent (containing OH in the molecule, -O-, -CO - and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide, and the like.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, Butyl propionate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetone, and γ-butyrolactone.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, And the like.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate , Ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, Methyl propionate, methyl propionate, methyl 2-ethoxy-2-methyl propionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol mono Propyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate , Di, and the like ethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate.

Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4- Pentanone, cyclohexanone, and isophorone.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerin.

Examples of the aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone.

These solvents may be used alone, or two or more of them may be used in combination.

Among them, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, 3- Methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, N-methylpyrrolidone, 4-hydroxy-4-methyl-2-pentanone, N, Propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, 3-methoxy-1-butanol, 3-methoxybutyl acetate, 3-methoxybutyl acetate, Ethyl ethoxypropionate, ethyl lactate, and N-methyl pyrrolidone are more preferable.

When the solvent (E) is contained, the content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass with respect to the total amount of the colorant composition. In other words, the total amount of solids of the coloring composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. When the content of the solvent (E) is within the above range, the flatness at the time of coating becomes good, and the color density tends not to be insufficient when the color filter is formed, so that display characteristics tend to be good.

In the present specification, "total amount of solids" refers to the total amount of components excluding the solvent (E) in the coloring composition. The total amount of the solid content and the content of each component thereof can be measured by a known analytical means such as liquid chromatography or gas chromatography.

The colorant (A)

The colorant (A) may be used alone as a dye containing the compound (AI) of the present invention as an active ingredient, but it may further contain other dyes (A1), pigments P) or mixtures thereof.

Examples of the dye (A1) include dyes such as oil soluble dyes, acid dyes, basic dyes, direct dyes, mordant dyes, amine salts of acid dyes and sulfonamide derivatives of acid dyes. and Colourists), or known dyes described in Dyeing Note (Color Dyeing). According to the chemical structure, it is also possible to use azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, Reel dyes, coumarin dyes, quinoline dyes and nitro dyes. Of these, organic solvent-soluble dyes are preferably used.

Specific examples of the dye (A1) include C.I. 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;

C.I. Solvent Red 24, 45, 49, 90, 91, 118, 119, 122, 124, 125, 127, 130, 132, 145, 160, 218;

C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;

C.I. Solvent Blue 4, 5, 37, 67, 70, 90;

C.I. Solvent Green 1, 4, 5, 7, 34, 35; C.I. Solvent dyes,

C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 91, 163, 168, 169, 172, 163, 163, 163, 163, 170, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 211, 212, 214, 220, 221, 228, 230, 232, 235, 242, 243, 251, 274, 289;

C.I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 87, 215, 198, 206, 211, 215, 216, 217, 218, 219, 288, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 276, 268, 270, 274, 277, 280, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;

C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

C.I. Acid Violet 6B, 7, 9, 17, 19, 30, 102, 120;

C.I. Acid Blue 1, 7, 9, 15, 18, 22, 29, 42, 59, 60, 62, 70, 72, 74, 82, 83, 86, 87, 90, 92, 93, 166, 167, 168, 170, 171, 184, 187, 192, 199, 210, 229, 234, 236, 242, 243, 256, 259, 267, 285, 296, 315, 335;

C.I. C.I., such as Acid Green 1, 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, Acid dyes,

C.I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 136, 138, 141;

C.I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;

C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 108, 109, 129, 132, 136, 138, 141;

C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

C.I. Direct Blue 1, 2, 6, 8, 15, 22, 25, 41, 57, 71, 76, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 198, 199, 200, 201, 202, 203, 207, 209, 210, 202, 203, 207, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;

C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, Direct dyes,

C.I. Dispersion Yellow 51, 54, 76, etc. C.I. Disperse dyes,

C.I. Basic Red 1, 10;

C.I. Basic Blue 1, 3, 5, 7, 9, 19, 24, 25, 26, 28, 29, 40, 41, 54, 58, 59, 64, 65, 66, 67, 68;

C.I. Basic Green 1; C.I. Basic dyes,

C.I. Reactive Yellow 2, 76, 116;

C.I. Reactive Orange 16;

C.I. Reactive red 36; C.I. Reactive dyes,

C.I. Modern Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

C.I. 43, 38, 39, 41, 43, 43, 43, 43, 42, 43, , 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95;

C.I. Modern orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

C.I. Modern Violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58;

C.I. 1, 2, 3, 7, 9, 12, 13, 15, 16, 19, 20, 21, 22, 26, 30, 31, 39, 40, 41, 43, 44, 49, 53, 61 , 74, 77, 83, 84;

C.I. Modern Green 1, 3, 4, 5, 10, 15, 26, 29, 33, 34, 35, 41, 43, 53; C.I. Modern dyes,

C.I. C.I. Vat dyes and the like. Among them, a violet dye is preferable.

The pigment (P) is not particularly limited, and known pigments can be used. For example, pigments classified as pigments in the color index (The Society of Dyers and Colourists) are cited.

As the pigment, for example,

C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138 , 139, 147, 148, 150, 153, 154, 166, 173, 194 and 214;

C.I. Orange pigments such as Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;

C.I. Red pigments such as Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, ;

C.I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60;

C.I. Violet pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;

C.I. Green pigments such as Pigment Green 7, 36, and 58;

C.I. Brown pigments such as Pigment Brown 23 and 25;

C.I. Pigment black 1, pigment black 7, and the like.

The pigment (P) is preferably a phthalocyanine pigment and a dioxazine pigment, more preferably C.I. Pigment Blue 15: 6 and Pigment Violet 23. By including the pigment, the transmission spectrum can be easily optimized, and the light resistance and chemical resistance of the color filter can be improved.

If necessary, the pigment may be subjected to surface treatment using a rosin treatment, a pigment derivative in which an acidic group or a basic group is introduced, graft treatment on the surface of the pigment with a polymer compound or the like, atomization treatment using a sulfuric acid atomization method or the like, A cleaning treatment with a solvent or water, a removal treatment with an ion exchange method of ionic impurities, or the like. The pigment preferably has a uniform particle size.

The pigment may be a pigment dispersion in which the pigment is uniformly dispersed in a solution by containing a pigment dispersant and carrying out a dispersion treatment. Each of the pigments may be dispersed singly, or various dispersions may be mixed and dispersed.

Examples of the pigment dispersing agent include surfactants, and surfactants such as cationic, anionic, nonionic, and amphoteric surfactants may be used. Specific examples thereof include pigment dispersants such as polyester-based, polyamine-based, and acrylic-based pigments. These pigment dispersants may be used alone or in combination of two or more. (Trade name) manufactured by Shin-Etsu Chemical Co., Ltd.), fullerene (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca), EFKA (registered trademark) (Manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.) and Disperbyk (registered trademark) (manufactured by Bigkema Corporation).

When a pigment dispersant is used, its amount to be used is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less, based on 100 parts by mass of the pigment. When the amount of the pigment dispersant is in the above range, a pigment dispersion in a uniformly dispersed state tends to be obtained.

The content of the compound (A-I) is preferably 5 mass% or more and 70 mass% or less, more preferably 5 mass% or more and 60 mass% or less, and still more preferably 5 mass% or more and 50 mass% or less, with respect to the total amount of the solid matter.

The content of the compound (A-I) is preferably 1% by mass or more and 100% by mass or less, and more preferably 10% by mass or more and 100% by mass or less, based on the total amount of the colorant (A).

When the compound (AI) and the compound (A-III) are mixed and used, the total content of the compound (AI) and the compound (A-III) is preferably 10 mass% or more and 70 mass% or less based on the total amount of the solid , More preferably 15 mass% or more and 60 mass% or less.

When the dye (A1) is contained, its content is preferably 0.5% by mass or more and 90% by mass or less, and more preferably 0.5% by mass or more and 70% by mass or less, based on the total amount of the colorant (A). When the pigment (P) is contained, the content thereof is preferably 1% by mass or more and 99% by mass or less, and more preferably 1% by mass or more and 70% by mass or less, based on the total amount of the colorant (A).

The content of the colorant (A) is preferably 5% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 60% by mass or less, and still more preferably 5% by mass or more and 50% by mass or less, based on the total amount of solid matter.

Resin (B)

The resin (B) is preferably an alkali-soluble resin (B). The alkali-soluble resin (B) (hereinafter also referred to as "resin (B)") may contain a structural unit derived from at least one monomer (Ba) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride ≪ / RTI >

Examples of such a resin (B) include the following resins [K1] to [K6].

(A) (hereinafter sometimes referred to as "(a)") selected from the group consisting of a resin [K1] unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride, A copolymer having a structural unit derived from a monomer (b) having an ethylenic unsaturated bond and a cyclic ether structure (hereinafter occasionally referred to as "(b)");

(A) and (b) which are copolymerizable with (a) the structural unit derived from the resin (K2) (a), the structural unit derived from the monomer (b) (c) "); < / RTI >

Resin [K3] a copolymer having a structural unit derived from (a) and a structural unit derived from (c);

Resin [K4] Resin (copolymer) having a structural unit derived from (a) and a structural unit derived from (c);

Resin (K5) Resin (copolymer) having a structural unit derived from (b) and a structural unit derived from (c);

Resin [K6] Resin (copolymer) having (a) added to the structural unit derived from (b) and having a structural unit further added with a carboxylic acid anhydride and a structural unit derived from (c).

(a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m- and p-vinylbenzoic acid;

Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid;

5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept- 5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo [2.2.1] hept- [2.2.1] hept-2-ene, and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;

Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride , Unsaturated dicarboxylic acid anhydrides such as dimethyl tetrahydrophthalic anhydride and 5,6-dicarboxybicyclo [2.2.1] hept-2-eno anhydride;

(Meth) acryloyloxyalkyl (meth) acrylate of a divalent or higher polyvalent carboxylic acid such as succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono Esters;

and unsaturated acrylates containing a hydroxyl group and a carboxyl group in the same molecule such as? - (hydroxymethyl) acrylic acid.

Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoints of copolymerization reactivity and the solubility of the resulting resin in an aqueous alkali solution.

(b) is a polymerizable compound having an ethylenic unsaturated bond and a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one member selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) .

(b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.

In the present specification, the term "(meth) acrylic acid" refers to at least one member selected from the group consisting of acrylic acid and methacrylic acid. The expressions such as "(meth) acryloyl" and "(meth) acrylate"

(b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter may be referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (b2) "), a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter occasionally referred to as" (b3) "), and the like.

(b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which a straight chain or branched aliphatic unsaturated hydrocarbon is epoxidized, and alicyclic unsaturated hydrocarbons (B1-2) having an epoxidized structure (hereinafter may be referred to as "(b1-2)").

(meth) acrylate,? -methyl glycidyl (meth) acrylate,? -ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl Vinylbenzyl glycidyl ether,? -Methyl-o-vinylbenzyl glycidyl ether,? -Methyl-o-vinylbenzyl glycidyl ether,? -Methyl- Methyl-p-vinylbenzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene, 2,4-bis (glycidyloxymethyl) styrene, 2,5- ) Styrene, 2,6-bis (glycidyloxymethyl) styrene, 2,3,4-tris (glycidyloxymethyl) styrene, 2,3,5- , 3,6-tris (glycidyloxymethyl) styrene, 3,4,5-tris (glycidyloxymethyl) styrene, 2,4,6-tris (glycidyloxymethyl) have.

(b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide (registered trademark) 2000 manufactured by Daicel Co.), 3,4-epoxycyclohexyl (Meth) acrylate (for example, Cyclomer (registered trademark) A400 manufactured by Daicel Chemical Industries, Ltd.), 3,4-epoxycyclohexylmethyl (meth) Die cell production), a compound represented by the formula (BI) and a compound represented by the formula (BII).

 (27)

[In the formula (BI) and the formula (BII), R ^a and R ^b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group.

X ^a and X ^b represent a single bond, * -R ^c -, * -R ^c -O-, * -R ^c -S- or * -R ^c -NH-.

R ^c represents an alkanediyl group having 1 to 6 carbon atoms.

* Represents the bonding position with O.]

Examples of the alkyl group having 1 to 4 carbon atoms represented by R ^a and R ^b include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl.

Examples of the alkyl group in which the hydrogen atoms of R ^a and R ^b are substituted with hydroxy include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, Methylpropyl group, propyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, And the like.

R ^a and R ^b are preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, specifically preferably a hydrogen atom, , An ethyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, more preferably a hydrogen atom and a methyl group.

Examples of the alkanediyl group of R < ^c > include a linear or branched alkanediyl group, and specifically exemplified by methylene, ethylene, propane-1,3-diyl, butane- A straight chain alkanediyl group such as a 1,5-diyl group or a hexane-1,6-diyl group; And a branched chain alkanediyl group such as propane-1,2-diyl group.

X ^a and X ^b are preferably a single bond, * -R ^c - or * -R ^c -O-, more preferably a single bond or * -R ^c -O-, particularly preferably a single bond, an ethylene group, * -CH ₂ may be mentioned -O- and * -CH ₂ CH ₂ -O-, can be cited more preferably a single _{bond, * -CH 2 CH 2 -O- (} * is a bond with O Position.

Examples of the compound represented by the formula (BI) include a compound represented by any one of the formulas (BI-1) to (BI-15). Among them, the expression (BI-1), the expression (BI-3), the expression (BI-5), the expression (BI- (BI-1), a compound represented by the formula (BI-7), a compound represented by the formula (BI-9) or a compound represented by the formula (BI-15) are more preferable.

(28)

 [Chemical Formula 29]

Examples of the compound represented by formula (BII) include compounds represented by any one of formulas (BII-1) to (BII-15). Among them, BII-1, BII-3, BII-5, BII-7, BII-9 or BII- (BII-1), a compound represented by the formula (BII-7), a compound represented by the formula (BII-9) or a compound represented by the formula (BII-15) are more preferable.

(30)

(31)

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone, or the compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When these compounds are used in combination, the content of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95: 5, more preferably 10:90 to 90:10, More preferably 20:80 to 80:20.

(b2) is more preferably a monomer having an oxetanyl group and a (meth) acryloyloxy group. (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3- Ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3- 3-ethyl-3-acryloyloxyethyl oxetane, and the like.

(b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group. (b3) specifically include tetrahydrofurfuryl acrylate (e.g., Viscot V # 150, Osaka Yuki Kagaku Kogyo Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

(b), it is preferable that (b1) that the reliability of heat resistance, chemical resistance and the like of the obtained color filter can be further improved. Furthermore, (b1-2) is more preferable because the storage stability of the coloring composition is excellent.

(meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert- (Meth) acrylate, cyclohexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (Meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate (also referred to in the art as "dicyclopentanyl (meth) acrylate" (Also referred to as "tricyclodecyl (meth) acrylate"), tricyclo [5.2.1.0 ^2,6 ] decen-8-yl (meth) acrylate (Meth) acrylate "), dicyclopentanyloxyethyl (meth) acrylate (Meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (Meth) acrylate; and (meth) acrylic acid esters such as benzyl (meth) acrylate;

(Meth) acrylic acid esters having a hydroxy group such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;

Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate;

2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5-methoxybicyclo [2.2.1] (2'-hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] hept- Ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept- 2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept- Cyclohexyl [2.2.1] hept-2-ene, 5,6-bis 2,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene and the like such as bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept- Cyclo-unsaturated compounds;

N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N- Dicarbonylimide derivatives such as 6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate and N- (9-acridinyl) maleimide;

Vinyl group-containing aromatic compounds such as styrene,? -Methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene and p-methoxystyrene; Vinyl group-containing nitriles such as acrylonitrile and methacrylonitrile; Halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; Vinyl group-containing amides such as acrylamide and methacrylamide; Esters such as vinyl acetate; Dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene; And the like.

Among them, (c) is preferably a vinyl group-containing aromatic compound, a dicarbonylimide derivative, or a bicyclo-unsaturated compound from the viewpoint of copolymerization reactivity and heat resistance. Specifically, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, and bicyclo [2.2.1] hept-2-ene are preferred.

The proportion of the structural units derived from each of the resins [K1] is preferably one of the total structural units constituting the resin [K1]

a structural unit derived from (a); 2 to 60 mol%

a structural unit derived from (b); , More preferably 40 to 98 mol%

a structural unit derived from (a); 10 to 50 mol%

a structural unit derived from (b); And more preferably 50 to 90 mol%.

When the ratio of the structural unit of the resin [K1] is within the above range, there is a tendency that the storage stability of the coloring composition, developability in forming a coloring pattern, and solvent resistance of the resulting color filter are excellent.

The resin [K1] can be prepared by, for example, the method described in "Experimental Method of Polymer Synthesis" (First Edition, First Edition, Chemical Synthesis, by Takatsuki Otsuka Co., Ltd., March 1, 1972) And can be produced by referring to the reference documents listed in the document.

Specifically, a predetermined amount of the components (a) and (b), a polymerization initiator and a solvent are placed in a reaction vessel, and oxygen is replaced by, for example, nitrogen, thereby forming a deoxygenation atmosphere. have. The polymerization initiator and the solvent to be used herein are not particularly limited and those generally used in the field can be used. Examples of the polymerization initiator include azo compounds such as 2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), organic peroxides (such as benzoyl peroxide) And the solvent may be any solvent as long as it dissolves the respective monomers, and includes the solvents listed as the solvent (E) of the coloring composition of the present invention.

As the obtained copolymer, the solution after the reaction may be used as it is, or a concentrated or diluted solution may be used, or a solid (powder) extracted by re-precipitation or the like may be used. In particular, since the solvent after the reaction can be directly used for preparing the coloring composition of the present invention by using a solvent contained in the coloring composition of the present invention as a solvent in such polymerization, the production process of the coloring composition of the present invention can be simplified.

The ratio of the structural units derived from each of the resins [K2] is preferably one of the total structural units constituting the resin [K2]

a structural unit derived from (a); 2 to 45 mol%

a structural unit derived from (b); 2 to 95 mol%

(c); It is preferably 1 to 65 mol%

a structural unit derived from (a); 5 to 40 mol%

a structural unit derived from (b); 5 to 80 mol%

(c); And more preferably 5 to 60 mol%.

When the ratio of the structural unit of the resin [K2] is within the above range, there is a tendency that storage stability of the coloring composition, developability in forming a coloring pattern, and solvent resistance, heat resistance and mechanical strength of the resulting color filter are excellent.

The resin [K2] can be produced, for example, in the same manner as described for the method of producing the resin [K1].

The proportion of the structural units derived from each of the resins [K3] is preferably one of the total structural units constituting the resin [K3]

a structural unit derived from (a); 2 to 60 mol%

(c); , More preferably 40 to 98 mol%

a structural unit derived from (a); 10 to 50 mol%

(c); And more preferably 50 to 90 mol%.

The resin [K3] can be produced, for example, in the same manner as described for the method of producing the resin [K1].

Resin [K4] is obtained by obtaining a copolymer of (a) and (c) and adding a cyclic ether having 2 to 4 carbon atoms of (b) to a carboxylic acid and / or carboxylic acid anhydride having (a) can do.

First, a copolymer of (a) and (c) is prepared in the same manner as described for the method of producing the resin [K1]. In such a case, the proportion of the respective structural units derived from each of them is preferably the same as that enumerated in the resin [K3].

Next, a cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer.

(a) and (c), the atmosphere in the flask is replaced with air in nitrogen, and (b) a reaction catalyst of a carboxylic acid or a carboxylic acid anhydride and a cyclic ether (for example, tris (K4) can be prepared by placing a polymerization inhibitor (for example, hydroquinone or the like) into a flask and reacting at 60 to 130 ° C for 1 to 10 hours, for example.

(b) is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). (b) is adjusted to this range, the balance between the storage stability of the colored composition, the developability in forming the pattern, and the solvent resistance, heat resistance, mechanical strength and sensitivity of the resulting pattern tends to be improved. (B1) is preferable for (b1) used in the resin [K4], and (b1-1) is more preferable because the reactivity of the cyclic ether is high and unreacted (b)

The amount of the reaction catalyst to be used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor to be used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c).

Reaction conditions such as injection method, reaction temperature and reaction time of each test agent can be appropriately controlled in consideration of the manufacturing facility or the amount of heat generated by polymerization. In addition, the injection method and the reaction temperature can be appropriately controlled in consideration of the amount of heat generated by the production equipment or polymerization, as in the case of the polymerization conditions.

In the production of the resin [K5], a copolymer of (b) and (c) is obtained in the same manner as in the above-mentioned process for producing the resin [K1]. The copolymer obtained in the same manner as described above can be used as a solution after the reaction as it is, or a concentrated or diluted solution may be used, or a solid (powder) extracted by re-precipitation or the like may be used.

the ratio of the structural units derived from the structural units (b) and (c) is preferably in the range of the total number of moles of the total structural units constituting the copolymer of (b) and (c)

a structural unit derived from (b); 5 to 95 mol%

(c); , More preferably 5 to 95 mol%

a structural unit derived from (b); 10 to 90 mol%

(c); And more preferably 10 to 90 mol%.

Furthermore, as a second step, a cyclic ether derived from the copolymer (b) having the copolymer (b) and the copolymer (c) under the same conditions as the method for producing the resin [K4] The resin [K5] can be obtained by reacting an anhydride.

In the second step, the amount of (a) to be reacted with the copolymer of (b) and (c) is preferably 5 to 80 moles per 100 moles of (b). (B1) is preferable for (b1) used in the resin [K5], and (b1-1) is more preferable because the reactivity of the cyclic ether is high and unreacted (b)

The resin [K6] is a resin obtained by further reacting the resin [K5] with a carboxylic acid anhydride. A carboxylic acid anhydride is reacted with a hydroxy group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride.

The resin [K6] is a resin obtained by further reacting a carboxylic acid anhydride with the resin [K5]. Specifically, the resin [K6] is a resin obtained by reacting a cyclic ether derived from (b) with a carboxylic acid or a carboxylic acid anhydride Can be produced by reacting a carboxylic acid anhydride with a hydroxy group generated by the reaction.

Examples of the carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, Tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride. The amount of the carboxylic acid anhydride to be used is preferably 0.5 to 1 mole based on 1 mole of the amount of (a).

Examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) A resin [K1] such as a (meth) acrylic acid copolymer; (Meth) acrylate / styrene / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2 (meth) acrylate / glycidyl .1.0 ^2,6] decyl (meth) acrylate / (meth) acrylic acid / N- cyclohexyl maleimide copolymer, the resin composition comprising 3,4-tricyclo [5.2.1.0 ^2,6] decyl (meth) acrylate / ( A resin [K2] such as a methacrylic acid / vinyltoluene copolymer, and 3-methyl-3- (meth) acryloyloxymethyloxetane / (meth) acrylic acid / styrene copolymer; A resin such as benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer, benzyl (meth) acrylate / tricyclodecyl (meth) acrylate / (meth) ]; A resin obtained by adding glycidyl (meth) acrylate to a benzyl (meth) acrylate / (meth) acrylic acid copolymer, a resin obtained by adding glycidyl (meth) acrylate to a tricyclodecyl (meth) acrylate / styrene / (K4) such as a resin obtained by adding glycidyl (meth) acrylate to a tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer; A resin obtained by reacting a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate with (meth) acrylic acid, a resin obtained by reacting tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) A resin [K5] such as a resin obtained by reacting (meth) acrylic acid with a copolymer; A resin such as a resin obtained by reacting a (meth) acrylic acid with a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate and tetrahydrophthalic anhydride in addition to the resin [K6] have.

The resin (B) is preferably one kind selected from the group consisting of a resin [K1], a resin [K2] and a resin [K3], more preferably a resin selected from the group consisting of a resin [K2] It is a species. If these resins are used, the coloring composition is excellent in developing property. From the viewpoint of the adhesion between the coloring pattern and the substrate, the resin [K2] is more preferable.

The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the coating film is improved, the residual film ratio is high, the solubility in the developing solution of the unexposed portion is good, and the resolution of the coloring pattern tends to be improved.

The dispersion degree (weight average molecular weight (Mw) / number average molecular weight (Mn)) of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.

The acid value of the resin (B) in terms of solid content is preferably 30 to 170 mg-KOH / g, more preferably 40 to 150 mg-KOH / g, and still more preferably 50 to 135 mg-KOH / g. The acid value is a value measured as the amount (mg) of potassium hydroxide necessary for neutralizing 1 g of the resin (B), and can be determined by titration using, for example, an aqueous potassium hydroxide solution.

When the resin (B) is contained, the content of the resin (B) is preferably 7 to 70 mass%, more preferably 13 to 65 mass%, and still more preferably 17 to 60 mass% with respect to the total amount of the solid content. When the content of the resin (B) is in the above range, a colored pattern can be formed, and the resolution and residual film ratio of the colored pattern tends to be improved.

The polymerizable compound (C)

The polymerizable compound (C) is a compound capable of polymerizing with an active radical and / or an acid generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenically unsaturated bond, Methacrylate ester compound.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl Acrylate, N-vinylpyrrolidone, and the above-mentioned (Ba), (Bb) and (Bc).

Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene Glycol di (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (metha) acrylate, tetrapentaerythritol deca (Meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified dipentaerythritol hexa Propylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate , Caprolactone-modified pentaerythritol tetra (meth) acrylate, and caprolactone-modified dipentaerythritol hexa (meth) acrylate. Of these, dipentaerythritol penta (meth) acrylate and dipentaerythritol Hexa (meth) acrylate is preferable.

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 to 1,500 or less.

When the polymerizable compound (C) is contained, the content of the polymerizable compound (C) is preferably 7% by mass or more and 65% by mass or less, more preferably 10% by mass or more and 60% And more preferably 12 mass% or more and 55 mass% or less.

When the resin (B) and the polymerizable compound (C) are contained, the content ratio of the resin (B) and the polymerizable compound (C) (resin (B): polymerizable compound (C) 20:80 to 80:20, and more preferably 30:70 to 80:20.

When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming a coloring pattern and the chemical resistance of the color filter tend to be improved.

The polymerization initiator (D)

The polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating an active radical or acid by the action of light or heat, and a known polymerization initiator can be used.

Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, imidazole compounds, triazine compounds and acylphosphine oxide compounds.

The O-acyloxime compound is a compound having a partial structure represented by the formula (d1). * Indicates a bonding position.

 (32)

Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy- 1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan- - ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] (3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethan- 1-imine, N- acetoxy- 1- [ -9-ethyl-6- (2-methylbenzoyl) -9H-carbazole < / RTI > -3-yl] -3-cyclopentylpropan-1-one-2-imine. Commercially available products such as Irgacure (registered trademark) OXE 01, OXE 02 (manufactured by BASF) and N-1919 (manufactured by ADEKA) may also be used. Among them, the O-acyloxime compound is preferably selected from the group consisting of N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan- 2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine, -Benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine is more preferable.

The alkylphenone compound is, for example, a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). Of these partial structures, the benzene ring may have a substituent.

 (33)

Examples of the compound having a partial structure represented by the formula (d2) include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan- (4-morpholinophenyl) -2-benzylbutan-1-one, 2- (dimethylamino) Butane-1-one and the like. IRGACURE 369, 907 and 379 (all manufactured by BASF) can be used.

Examples of the compound having a partial structure represented by the formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2- Hydroxy-2-methyl-1- (4-isopropenylphenyl) propane-1-one, 1-hydroxycyclohexylphenylketone and 2-hydroxy- ,? -? - diethoxyacetophenone, and benzyl dimethyl ketal.

From the viewpoint of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

The non-imidazole compound includes, for example, a compound represented by formula (d4).

(34)

[In the formula (d4), R ^d1 to R ^d6 represent an aryl group having 6 to 10 carbon atoms which may have a substituent.]

Examples of the aryl group having 6 to 10 carbon atoms represented by R ^d1 to R ^d6 include a phenyl group, a toluyl group, a xylyl group, an ethylphenyl group and a naphthyl group, and preferably a phenyl group.

Examples of the substituent capable of substituting the aryl group of R ^d1 to R ^d6 include a halogen atom and an alkoxy group having 1 to 4 carbon atoms. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and preferably a chlorine atom. Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a butoxy group and the like, preferably a methoxy group.

Examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3- Phenyl) -4,4 ', 5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372, JP-A-6-75373, -Bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis Bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (dialkoxyphenyl) biimidazole, 2,2'-bis Phenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) bimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Laid- Imidazole compounds in which the phenyl group at the 4,4 ', 5,5'-position is substituted by a carboalkoxy group (see, for example, JP-A-7-10913). Among them, a compound represented by the following formula and a mixture thereof are preferable.

(35)

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) (Trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) Bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) -Yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-tri Azine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4- Methyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like.

Further, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; Benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (tert- butylperoxycarbonyl) benzophenone, Benzophenone compounds such as 2,4,6-trimethylbenzophenone; Quinone compounds such as 9,10-phenanthrenequinone, 2-ethyl anthraquinone, camphorquinone, etc .; Butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.

These are preferably used in combination with a polymerization initiator (D1) (particularly amines) to be described later.

Examples of the polymerization initiator that generates an acid include 4-hydroxyphenyldimethylsulfonium-p-toluene sulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium- p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium-p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p- Onium salts such as toluene sulfonate and diphenyl iodonium hexafluoroantimonate, nitrobenzyl tosylates, and benzoin tosylates.

As the polymerization initiator (D), a polymerization initiator that generates an active radical is preferable. Specifically, at least a polymerization initiator selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a non- And more preferably a polymerization initiator comprising an O-acyloxime compound.

When the polymerization initiator (D) is contained, the content of the polymerization initiator (D) is preferably 0.1 part by mass to 40 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) 1 part by mass to 30 parts by mass.

The polymerization initiator (D1)

The polymerization initiator (D1) is a compound or a sensitizer used for promoting polymerization of a polymerizable compound initiated by polymerization initiator. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).

Examples of the polymerization initiator (D1) include an amine compound, an alkoxyanthracene compound, a thioxanthone compound, and a carboxylic acid compound.

Examples of the amine compound include alkanolamines such as triethanolamine, methyldiethanolamine and triisopropanolamine; Aminobenzoic acid esters such as methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate and 2-ethylhexyl 4-dimethylaminobenzoate; N, N-dimethyl para-toluidine; Alkylamino such as 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone and 4,4'- Benzophenone; Among them, alkylaminobenzophenone is preferable, and 4,4'-bis (diethylamino) benzophenone is preferable. And commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) may be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, Dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene and the like.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1- Citoxanthone and the like.

Examples of the carboxylic acid compound include phenylsulfanyl acetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, Chlorophenylsulfanyl acetic acid, dichlorophenylsulfanyl acetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.

When these polymerization initiation assistants (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) . When the amount of the polymerization initiator (D1) is within the above range, a colored pattern can be formed with a higher sensitivity, and the productivity of the color filter tends to be improved.

Leveling agent (F)

Examples of the leveling agent (F) include a silicone surfactant, a fluorinated surfactant, and a silicon surfactant having a fluorine atom. These may have a polymerizable group in the side chain.

Examples of the silicone surfactant include a surfactant having a siloxane bond in the molecule. Specifically, Toray Silicon DC3PA, copper SH7PA, copper DC11PA, copper SH21PA, copper SH28PA, copper SH29PA, copper SH30PA, copper SH8400 KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 Manufactured by Japan Performance Materials Japan Co., Ltd.).

Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain in the molecule. Concretely, it is preferable to use a mixture of FLORAD (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Ltd.), Megapack (registered trademark) F142D, copper (equivalent) F171, copper (same) F-177, F183, F554, R30, RS-718-K (manufactured by DIC), F-TOP (registered trademark) EF301, (Trade name) EF303, EF351 and EF352 (manufactured by Mitsubishi Materials Denshi Kasei Co., Ltd.), Surflon (registered trademark) S381, S382, S1002, ) SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Co., Ltd.).

Examples of the silicon-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megapac (registered trademark) R08, Dongbang BL20, Dongbu F475, Dongbu F477 and Dongbu F443 (manufactured by DIC Corporation).

When the leveling agent (F) is contained, the content thereof is preferably 0.001 mass% or more and 0.5 mass% or less, more preferably 0.002 mass% or more and 0.4 mass% or less, further preferably 0.005 mass% or more 0.3% by mass or less. When the content of the leveling agent (F) is in the above range, the flatness of the color filter can be improved.

Other ingredients

The coloring composition may contain additives known in the art such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and the like, if necessary.

Method for producing coloring composition

The coloring composition containing the resin (B), the polymerizable compound (C), the polymerization initiator (D) and the solvent (E) (A), a leveling agent (F), a polymerization initiator (D1) and other components other than the polymerization initiator (D), the solvent (E) and the compound .

When the pigment (P) is contained, the pigment is preferably mixed with part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. At this time, if necessary, a part or all of the pigment dispersant and the resin (B) may be blended. The desired coloring composition can be prepared by mixing the remaining components in the resulting pigment dispersion to a predetermined concentration.

In the present invention, the compound (A-I) may be mixed with a solvent to obtain a colored dispersion. If the coloring composition is further mixed with the resin (B), the polymerizable compound (C), the polymerization initiator (D) or the like after preparing the coloring dispersion, heat resistance when made into a color filter can be further increased.

Any solvent that can be used as the solvent (E) of the coloring composition can be used as the solvent. The solvent (E1) particularly excellent for the purpose of dispersing the compound (AI) is, for example, an ether ester solvent, more preferably a solvent in which one hydroxy group of an alkylene glycol or a polyalkylene glycol is etherified and the remaining hydroxy group is esterified For example, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol Monobutyl ether acetate, dipropylene glycol methyl ether acetate, and the like. These may be included singly or in various forms.

The amount of the solvent (E1) is, for example, 4 to 1000 parts by mass, preferably 6 to 200 parts by mass, and more preferably 9 to 100 parts by mass with respect to 1 part by mass of the compound (A-I).

In preparing the colored dispersion, it is preferable to use a dispersing agent. As the dispersing agent, for example, known pigment dispersants such as cationic, anionic, nonionic, amphoteric, polyester, polyamine, acrylic and the like can be used. These pigment dispersants may be used alone or in combination of two or more. Examples of the pigment dispersing agent include KP (manufactured by Shinetsu Kagaku Kogyo K.K.), fullerene (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca), EFKA (manufactured by BASF) (Manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk, BYK (manufactured by Big Chemical), and the like.

The amount of the dispersing agent is, for example, 1 to 1000 parts by mass, preferably 3 to 100 parts by mass, more preferably 5 to 90 parts by mass, particularly preferably 10 to 80 parts by mass with respect to 100 parts by mass of the compound (A-I).

When the dye (A1) is contained in the coloring composition, it may contain some or all, preferably all, of the dye (A1) in advance, if necessary. The amount of the dye (A1) in the coloring dispersion is, for example, from 0.1 to 20 parts by mass, preferably from 0.5 to 15 parts by mass, more preferably from 1 to 10 parts by mass, based on 100 parts by mass of the compound (A-I).

The colored dispersion may contain a part or all, preferably a part of the resin (B) used in the coloring composition in advance, if necessary. By preliminarily including the resin (B), the dispersibility in the case of being made into a colored composition can be further improved. The solid content of the resin (B) in the coloring dispersion is, for example, 1 to 300 parts by mass, preferably 10 to 100 parts by mass, and more preferably 20 to 70 parts by mass, based on 100 parts by mass of the compound (A-I).

In preparing the dispersion, it is preferable to finely disperse the dispersion by appropriately adding the necessary components and then using a dispersing device. As the dispersing device, a bead mill device may be used. The beads to be used are generally hard beads such as zirconia beads and the particle size thereof is selected from the range of 0.05 mm to 20 mm, preferably 0.1 to 10 mm, more preferably 0.1 to 0.5 mm.

It is also preferable to prepare the solution by dissolving the compound (A-I) in a part or all of the solvent (E) in advance. Furthermore, it is preferable to filter the solution with a filter having a pore diameter of about 0.01 to 1 mu m.

The colored composition after mixing is preferably filtered with a filter having a pore size of 0.01 to 10 mu m or so.

Method for manufacturing color filter

Examples of the method for producing a colored pattern from the colored composition of the present invention include a photolithographic method, an inkjet method, a printing method, and the like. Among them, the photolithographic method is preferable. The photolithography method is a method in which the above-mentioned coloring composition is applied to a substrate, followed by drying to form a coloring composition layer, and the coloring composition layer is exposed and developed via a photomask. A colored coating film which is a cured product of the colored composition layer can be formed by photolithography without using and / or developing a photomask during exposure. The coloring pattern or colored coating film thus formed can be used as a color filter.

The thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted depending on the purpose and application, and is, for example, from 0.1 to 30 μm, preferably from 0.1 to 20 μm, more preferably from 0.5 to 6 μm.

Examples of the substrate include a glass plate such as quartz glass, borosilicate glass, aluminosilicate glass and soda lime glass whose surface is coated with silica, a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, Silver / copper / palladium alloy thin film, or the like is formed. A separate color filter layer, a resin layer, a transistor, a circuit, and the like may be formed on these substrates.

The formation of each color pixel by the photolithographic method can be performed by a known or common apparatus or condition. For example, it can be manufactured as follows.

First, the coloring composition is applied onto a substrate, followed by drying by heating (prebaking) and / or drying under reduced pressure to remove volatile components such as a solvent and drying to obtain a smooth colored composition layer.

Examples of the application method include a spin coating method, a slit coating method, and a slit and spin coating method.

The temperature in the case of performing heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

In the case of performing the reduced-pressure drying, it is preferably carried out at a temperature of 20 to 25 캜 under a pressure of 50 to 150 Pa.

The film thickness of the coloring composition layer is not particularly limited and may be appropriately selected depending on the film thickness of the intended color filter.

Next, the coloring composition layer is exposed through a photomask for forming a desired coloring pattern. The pattern on the photomask is not particularly limited and a pattern according to the intended use is used.

As a light source used for exposure, a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, light having a wavelength of less than 350 nm may be cut using a filter cutting this wavelength region, or light having a wavelength in the vicinity of 436 nm, around 408 nm, or around 365 nm may be selectively extracted using a bandpass filter for extracting these wavelength regions can do. Specifically, examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp, and a halogen lamp.

It is preferable to use an exposure apparatus such as a mask aligner and a stepper because it is possible to uniformly irradiate the entire exposure surface with parallel rays or to precisely align the photomask with the substrate on which the coloring composition layer is formed.

A coloring pattern is formed on the substrate by bringing the colored composition layer after exposure into contact with a developing solution. By the development, the unexposed portion of the colored composition layer is dissolved and removed in the developer. As the developing solution, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, tetramethylammonium hydroxide or the like is preferable. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. Further, the developing solution may contain a surfactant.

The developing method may be any of paddle method, dipping method and spray method. Further, the substrate may be tilted at an arbitrary angle at the time of development.

It is preferable to rinse after development.

Further, post-baking is preferably performed on the obtained color pattern. The post bake temperature is preferably 150 to 250 DEG C, more preferably 160 to 235 DEG C. The post bake time is preferably from 1 to 120 minutes, more preferably from 10 to 60 minutes.

The compound of the present invention has a high absorbance and, according to the coloring composition using the coloring composition, a color filter excellent in solvent resistance can be produced. The color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state image pickup device.

< Example >

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples. In the examples, "%" and "parts" indicating the content or amount are based on mass unless otherwise specified.

Unless otherwise specified, the reaction was carried out in a nitrogen atmosphere. Hereinafter, the structure of the compound was confirmed by mass analysis (LC: Agilent 1200 type, MASS: Agilent LC / MSD type).

Example  One.

10.0 parts of potassium thiocyanate and 55.0 parts of acetonitrile were put in a flask equipped with a stirrer, a cooling tube and a stirrer, and the mixture was stirred at room temperature for 30 minutes. And 13.6 parts of 2-fluorobenzoyl chloride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added dropwise over 10 minutes, followed by stirring at room temperature for 2 hours. 11.6 parts of N-ethyl-o-toluidine (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added dropwise and the mixture was stirred at room temperature for 30 minutes. 30.0 parts of sodium chloroacetate was dissolved in 40.8 parts of ion-exchanged water, and this solution was added dropwise, followed by dropwise addition of 22.9 parts of a 30% sodium hydroxide aqueous solution. After completion of dropwise addition, the mixture was stirred at room temperature for 20 hours. After adding 204.0 parts of ion-exchanged water, the mixture was stirred at room temperature for 1 hour, and the precipitated solid was filtered off. The resulting solid was washed with 41.0 parts of acetonitrile and then washed with 200.0 parts of ion-exchanged water to obtain a wet cake of the compound represented by the formula (B-I-1). A flask equipped with a cooling tube and a stirrer was charged with 68.0 parts of ion-exchanged water, 68.0 parts of toluene and 15.8 parts of acetic acid, and the mixture was stirred at room temperature for 30 minutes. The wet cake of the obtained compound represented by the formula (B-I-1) was added in the entire amount, and the mixture was stirred at room temperature for 2 hours. 35.4 parts of a 30% aqueous solution of sodium hydroxide was added, and an organic layer was obtained by liquid separation and purification. The obtained organic layer was subjected to liquid separation and purification using 68.0 parts of ion-exchanged water, followed by liquid separation and purification using a 35% hydrochloric acid aqueous solution. Magnesium sulfate was added to the obtained organic layer, and after stirring for 1 hour, the solid was separated by filtration. The solvent was distilled off to obtain 18.5 parts of a compound represented by the formula (B-I-2). The yield was 69%.

(36)

(37)

15.3 parts of N-methylaniline (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 60 parts of N, N-dimethylformamide were added to a flask equipped with a condenser and a stirrer, and then the mixed solution was ice-cooled. 5.7 parts of 60% sodium hydride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added portionwise over 30 minutes under ice-cooling, and the mixture was stirred for 1 hour while being warmed to room temperature. 10.4 parts of 4,4'-difluorobenzophenone (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added to the reaction solution little by little and the mixture was stirred at room temperature for 24 hours. The reaction liquid was added little by little to 200 parts of ice water, and the mixture was allowed to stand at room temperature for 15 hours. When water was removed by decantation, a viscous solid was obtained as a residue. After adding 60 parts of methanol to the resulting solid, the mixture was stirred at room temperature for 15 hours. The precipitated solid was separated by filtration and then purified by column chromatography. The purified light yellow solid was dried at 60 캜 under reduced pressure to obtain 9.8 parts of a compound represented by the formula (BP-1). The yield was 53%.

(38)

8.2 parts of the compound represented by the formula (BI-2), 10.0 parts of the compound represented by the formula (BP-1) and 20.0 parts of toluene were charged into a flask equipped with a stirrer and a cooling tube, And the mixture was stirred at 95 to 100 占 폚 for 3 hours. The reaction mixture was then cooled to room temperature and then diluted with 170.0 parts of isopropanol. Subsequently, the diluted reaction solution was poured into 300.0 parts of saturated saline, 100 parts of toluene was added, and the mixture was stirred for 30 minutes. Subsequently, stirring was stopped, and the mixture was allowed to stand for 30 minutes. The organic layer and the aqueous layer were separated. After the aqueous layer was discarded by separating operation, the organic layer was washed with 300 parts of saturated saline. An appropriate amount of sodium sulfate (manganese) was added to the organic layer and stirred for 30 minutes, followed by filtration to obtain a dried organic layer. The obtained organic layer was distilled off with an evaporator to obtain a bluish green solid. Further, the violet solid was dried at 60 DEG C under reduced pressure to obtain 18.4 parts of a compound represented by the formula (A-IV-1). The yield was 100%.

[Chemical Formula 39]

Identification of the compound represented by the formula (A-IV-1)

(Mass analysis) Ionization mode = ESI +: m / z = 687.3 [M-Cl] ⁺

Exact Mass: 722.3

12.4 parts of the compound represented by the formula (A-IV-1) and 45.5 parts of chloroform were put in a flask equipped with a condenser and a stirrer, and stirred. 10 parts of chlorosulfonic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added thereto, and the mixture was stirred at 25 to 30 ° C for 18 hours. After cooling to room temperature, 210 parts of N, N-dimethylformamide was added, and the reaction liquid was added dropwise to 2610 parts of toluene. After stirring for 1 hour, the solid obtained by filtration was washed with 870 parts of toluene and dried at 60 ° C under reduced pressure to obtain 12.9 parts of a compound represented by the formula (A-III-1). The yield was 89%.

(40)

Identification of the compound represented by the formula (A-III-1)

(Mass analysis) Ionization mode = ESI +: m / z = 845.3 [M] ⁺

      Exact Mass: 846. 2

In a flask equipped with a cooling tube and a stirrer, 69.8 parts of the compound represented by the formula (A-III-1) and 418 parts of chloroform were added and stirred. 369.7 parts of phosphorus oxychloride was added dropwise, and the mixture was stirred at 60 占 폚 for 4 hours. After cooling to room temperature, the reaction solution was poured into 5000 parts of cold water and stirred for 30 minutes. Stirring was stopped, and the mixture was allowed to stand for 30 minutes. The organic layer and the water layer were separated. The obtained organic layer was washed twice with 4000 parts of cold water. 14.7 parts of trifluoromethanesulfonamide and 10 parts of triethylamine were dissolved in 100 parts of chloroform, and the mixture was allowed to react at room temperature for 12 hours. The reaction solution was poured into 5000 parts of ion-exchanged water and stirred for 30 minutes. Stirring was stopped, and the mixture was allowed to stand for 30 minutes. The organic layer and the water layer were separated. The obtained organic layer was washed twice with 4000 parts of ion-exchanged water. After 200 parts of magnesium sulfate was added to the organic layer and the mixture was stirred for 1 hour, the organic layer was evaporated off with an evaporator to obtain a bluish-purple solid. Further, the bluish green solid was dried under reduced pressure at 60 占 폚 and a 32:41:16 mixture of the compounds represented by the formulas (A-III-1), (A-II-1) and (A- Mol basis). This mixture is referred to as a colorant (A-II-3).

(41)

Identification of the compound represented by the formula (A-II-1)

(Mass analysis) Ionization mode = ESI +: m / z = 978.5 [M] ⁺

      Exact Mass: 977.2

(42)

Identification of the compound represented by the formula (A-II-2)

(Mass analysis) Ionization mode = ESI +: m / z = 1109.5 [M] ⁺

      Exact Mass: 1108.1

Example  2.

2.0 parts of the compound represented by the formula (A-IV-1) and 5.7 parts of methylene chloride were added to a flask equipped with a stirrer, a condenser and a cooling tube, and 1.6 parts of chlorosulfonic acid was added dropwise at 25 to 30 ° C and stirred at the same temperature for 3 hours . Then, a mixture of 3.3 parts of DMF and 0.3 part of ion-exchanged water was added dropwise to not more than 25 캜 to prepare a solution. This solution was poured into 32.7 parts of toluene to separate the liquid portion, and the residue was further washed with 16.3 parts of toluene. The remaining residue was concentrated under reduced pressure with an Evaporator, and the concentrate was poured into 31.2 parts of ion-exchanged water to precipitate crystals and filtrate. This coarse filtrate was suspended in 13.0 parts of a 20% aqueous sodium chloride solution, filtered, and the filtered solid was washed with 13.0 parts of a 20% aqueous sodium chloride solution and dried under reduced pressure at 35 ° C. Subsequently, this dried material was dissolved in 6.2 parts of methanol. The insoluble material was filtered, concentrated under reduced pressure with an evaporator, and dried under reduced pressure at 35 ° C to obtain 1.9 parts of a compound represented by the formula (A-III-1) as a blue solid. The yield was 97.9%.

(43)

Identification of the compound represented by the formula (A-III-1)

(Mass analysis) Ionization mode = ESI +: m / z = 845.3 [M] ⁺

      Exact Mass: 846.2

The following reaction was carried out in a nitrogen atmosphere. 2.0 parts of the compound represented by the formula (A-III-1) obtained above and 10.0 parts of acetonitrile were fed into a flask equipped with a stirrer, a condenser and a cooling tube, and 1.0 part of phosphorus oxychloride was added dropwise at 70 to 80 ° C. And the mixture was stirred at the same temperature for 2 hours. Subsequently, the reaction mixture was cooled to 5 ° C, and 1.0 part of trifluoromethanesulfonamide was added to the reaction mixture. Subsequently, 2.3 parts of triethylamine was added dropwise at 5 to 15 占 폚, and the mixture was stirred at 15 to 30 占 폚 for 2 hours. 10.0 parts of methyl ethyl ketone and 10.0 parts of a 20% aqueous sodium chloride solution were poured into the reaction solution, and the mixture was concentrated under reduced pressure using an evaporator. 15.0 parts of methylene chloride and 10.0 parts of ion-exchanged water were poured into the concentrated residue, and the organic layer and the aqueous layer were separated. The organic layer was concentrated under reduced pressure with an evaporator and dried under reduced pressure at 35 ° C to obtain a compound represented by the formula (A-II-2) 3.1 parts as a blue solid. The yield was 107.7%.

(44)

Identification of the compound represented by the formula (A-II-2)

(Mass analysis) Ionization mode = ESI +: m / z = 1109.5 [M] ⁺

      Exact Mass: 1108.1

Example  3.

2.0 parts of the compound represented by the formula (A-II-2), 3.4 parts of magnesium chloride hexahydrate, 40.0 parts of dimethyl sulfoxide and 16.0 parts of ion-exchanged water were charged into a flask equipped with a stirrer, Lt; / RTI &gt; After the reaction mixture was cooled to room temperature, it was added dropwise to a solution of 161.3 parts of ion-exchanged water and 53.8 parts of magnesium chloride hexahydrate, followed by stirring at 40 ° C for 30 minutes. The resulting suspension was filtered to wash the washed solid twice with 20.0 parts of ion-exchanged water and 50.0 parts of ion-exchanged water. The obtained solid was dried under reduced pressure at 60 캜 to obtain 1.9 parts of a compound represented by the formula (A-II-4).

[Chemical Formula 45]

Example  4.

The same reaction as in Example 3 was carried out except that magnesium chloride hexahydrate was changed to zinc chloride to synthesize a compound represented by the formula (A-II-5).

(46)

Example  5.

The same reaction as in Example 3 was carried out except that magnesium chloride hexahydrate was changed to barium chloride dihydrate to synthesize a compound represented by the formula (A-II-6).

(47)

Example  6.

(A-III-2) and (A-II-7) were obtained in the same manner as in Example 1 except that the compound represented by the formula (BP-1) , A 30: 52: 9 mixture (based on mole) of the compound represented by the formula (A-II-8) was obtained. This mixture is referred to as a coloring material (A-II-9). In addition, the formula, -SO ₃ ^- and -SO ₂ -N ^- -SO ₂ -CF ₃ is substituted to mean that any of hydrogen atoms included in the partial structure in parenthesis.

(48)

(49)

Identification of the compound represented by the formula (A-III-2)

(Mass analysis) Ionization mode = ESI +: m / z = 931.5 [M] ⁺

      Exact Mass: 930.3

(50)

Identification of the compound represented by the formula (A-II-7)

(Mass analysis) Ionization mode = ESI +: m / z = 1063.5 [M] ⁺

      Exact Mass: 1061.3

(51)

Identification of the compound represented by the formula (A-II-8)

(Mass analysis) Ionization mode = ESI +: m / z = 1193.5 [M] ⁺

      Exact Mass: 1192.2

Example  7.

A compound represented by the formula (A-II-8) was obtained in the same manner as in Example 2 except that the compound represented by the formula (BP-1) was changed to the compound represented by the formula (BP-2).

(52)

Identification of the compound represented by the formula (A-II-8)

(Mass analysis) Ionization mode = ESI +: m / z = 1193.5 [M] ⁺

      Exact Mass: 1192.2

Example  8.

The same reaction as in Example 3 was carried out except that the compound represented by the formula (A-II-2) was changed to the compound represented by the formula (A-II-8) Compound was synthesized.

(53)

Example  9.

The same reaction as in Example 4 was carried out except that the compound represented by the formula (A-II-2) was changed to the compound represented by the formula (A-II-8) Compound was synthesized.

(54)

Example  10.

The same reaction as in Example 5 was carried out except that the compound represented by the formula (A-II-2) was changed to the compound represented by the formula (A-II-8) Compound was synthesized.

(55)

Comparative Example  1, 2.

(Hereinafter also referred to as a compound (AX-1)) and a compound represented by the formula (AX-2) (hereinafter referred to as a compound (AX-1)) in accordance with the method described in Japanese Patent Application Laid-Open No. 2015-38201 AX-2)) was synthesized.

(56)

(57)

Synthetic example  One.

A nitrogen purged flask equipped with a reflux condenser, a dropping funnel and a stirrer was purged with nitrogen to make a nitrogen atmosphere, and 100 parts of propylene glycol monomethyl ether acetate was added and heated to 85 DEG C with stirring. Then, 19 parts of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan-8-yl acrylate and 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane- A solution prepared by dissolving 171 parts of propylene glycol monomethyl ether acetate (trade name: "E-DCPA &quot;, manufactured by Daicel Chemical Industries, Ltd.) Followed by dropwise addition over about 5 hours. On the other hand, a solution prepared by dissolving 26 parts of polymerization initiator 2,2'-azobis (2,4-dimethylvaleronitrile) in 120 parts of propylene glycol monomethyl ether acetate was dropped into a flask over about 5 hours using a separate dropping pump did. After the dropping of the polymerization initiator was completed, the temperature was maintained at the same temperature for about 3 hours, and then cooled to room temperature to obtain a solution of a copolymer (resin (B-1)) having a solid content of 43.5%. The weight average molecular weight of the obtained resin (B-1) was 8000, the degree of dispersion was 1.98, and the acid value in terms of solid content was 53 mg-KOH / g.

(58)

Synthetic example  2.

In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, an appropriate amount of nitrogen was poured into a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added and heated to 80 DEG C with stirring. Then, 38 parts of acrylic acid, a mixture of 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8 and 9-yl acrylate (containing ratio of 50:50 in molar ratio) (trade name: E-DCPA Manufactured by Daicel Co., Ltd.) in 125 parts of propylene glycol monomethyl ether acetate was dropwise added thereto using a dropping pump over about 5 hours. On the other hand, a solution obtained by dissolving 33 parts of polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise into the flask over about 6 hours using a separate dropping pump . After the dropping of the polymerization initiator was completed, the temperature was maintained at the same temperature for about 4 hours and then cooled to room temperature to obtain a copolymer (resin (B-2)) having a solid content of 35.1%. The resin (B-2) thus obtained had a weight-average molecular weight of 9200, a degree of dispersion of 2.08, and an acid value in terms of solid content of 77 mg-KOH / g.

[Chemical Formula 59]

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by the GPC method under the following conditions.

Device ; HLC-8120 GPC (manufactured by Tosoh Corporation)

column ; TSK-GEL G2000 HXL

Column temperature; 40 ℃

 Solvent; THF

 Flow rate; 1.0 mL / min

 Solid concentration of the test solution; 0.001 to 0.01 mass%

 Dose; 50 μL

 Detector; RI

 Calibration standards; TSK STANDARD POLYSTYRENE

      F-40, F-4, F-288, A-2500, A-500

     (Manufactured by TOSOH CORPORATION)

The ratio (Mw / Mn) of the weight average molecular weight and the number average molecular weight in terms of polystyrene obtained as described above was dispersed.

&Lt; Preparation of colored curable resin composition >

Example  11 to 20 and Comparative Example  3 to 4.

Each component was mixed with the following composition to obtain a colored curable resin composition.

In Table 14, each component represents the following compound.

(A-II-2): A compound represented by the formula (A-II-2)

(A-II-3): Coloring material (A-II-3)

(A-II-4): A compound represented by the formula (A-II-4)

(A-II-5): A compound represented by the formula (A-II-5)

(A-II-6): A compound represented by the formula (A-II-6)

(A-II-8): A compound represented by the formula (A-II-8)

(A-II-9): Coloring material (A-II-9)

(A-II-10): A compound represented by the formula (A-II-10)

(A-II-11): A compound represented by the formula (A-II-11)

(A-II-12): A compound represented by the formula (A-II-12)

(A-X-1): A compound represented by the formula (A-X-1)

(A-X-2): A compound represented by the formula (A-X-2)

(B-1): Resin (B-1) (in terms of solid content)

(C-1): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nihon Kayaku Co., Ltd.)

(Irgacure (registered trademark) OXE-01 manufactured by BASF), O-acyloxime (D-1) compound)

(E-1): Propylene glycol monomethyl ether acetate

(E-2): N-methylpyrrolidone

(E-3): Ethyl lactate

(F-1): polyether-modified silicone oil (in terms of solid content) (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.)

&Lt; Fabrication of color filter &

The above-mentioned colored curable resin composition was coated on a 2 inch square glass substrate (# 1737; Corning) by spin coating and then pre-baked at 100 ° C for 3 minutes to form a colored composition layer. After cooling, the substrate was exposed using an exposure apparatus (TME-150 RSK; manufactured by Topcon Co., Ltd.) at an exposure amount of 150 mJ / cm ² (365 nm standard) in an air atmosphere. Also, no photomask was used. The coloring composition layer after exposure was post-baked in an oven at 180 캜 for 20 minutes to prepare a color filter (film thickness 2.0 탆).

&Lt; Measurement of absorbance &

0.35 g of the resulting compound or color material was dissolved in chloroform to make a volume of 250 cm ³ and 2 cm ³ of the solution was diluted with chloroform to make a volume of 100 cm ³ (concentration: 0.028 g / L) ; 1 cm) was used to measure the absorption spectrum. The absorbance at a maximum absorption wavelength in terms of 0.028 g / L was evaluated according to the following criteria.

A: 2.0 or higher

B: 1.5 or more and less than 2.0

C: less than 1.5

< Solvent resistance  Evaluation>

The color difference (DELTA Eab *) before and after the immersion of the coating film was measured using a colorimeter (OSP-SP-200, manufactured by OLYMPUS CO., LTD.) And the following colorimetric . The value of? Eab * is a value obtained from the following color difference formula by the spatial colorimetry system of CIE 1976 (L *, a *, b *) (Japanese Society of Color Science Handbook of Color Science Handbook (1986) p.266).

? Eab * = {(? L *) 2+ (? A *) 2+ (? B *) 2 1/2

A: less than 5.0

B: 5.0 to less than 10.0

C: 10.0 or later

coloring agent Solvent resistance Compound / coloring matter Absorbance Example 12 (A-II-3) A A Example 17 (A-II-9) A A Comparative Example 3 (A-X-1) A C Comparative Example 4 (A-X-2) B A

&Lt; Measurement of voltage holding ratio &

0.025 g of the obtained compound and 1 g of liquid crystal (MCL-6608, manufactured by Merck Co., Ltd.) were mixed and heated in a sample bottle at 120 캜 for 50 minutes. The mixture was transferred to a centrifuge tube, and centrifugation was performed twice with MICRO SIX (manufactured by Asuzen Co., Ltd.) for 30 minutes. The upper portion of the mixture was sealed in a liquid crystal evaluation cell (KSRT-05 / BIIIMINTS 05X, manufactured by EHC Co., Ltd.), and the liquid crystal property evaluation device (Model 6254 manufactured by Toyo Techno Co., Ltd.) Were measured and evaluated based on the following criteria.

Measuring conditions

Applied voltage Pulse amplitude: 5V

* Voltage maintenance ratio: potential difference of the liquid crystal cell after 1000 milliseconds / value of voltage applied at 0 milliseconds

Evaluation standard

A: 95% or more

B: 85% or more and less than 95%

C: Less than 85%

coloring agent Solvent resistance Compound / coloring matter Voltage holding ratio Example 11 (A-II-2) A A Example 13 (A-II-4) A A Example 14 (A-II-5) A A Example 15 (A-II-6) A A Example 16 (A-II-8) A A Example 18 (A-II-10) A A Example 19 (A-II-11) A A Example 20 (A-II-12) A A Comparative Example 3 (A-X-1) C C Comparative Example 4 (A-X-2) C A

Example  21 to 24, Comparative Example  5, 6.

How to make dispersion

After each component shown in Table 17 was weighed, 600 parts of zirconia beads having a thickness of 0.4 mu m were added and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU) to prepare dispersions 1 to 6.

Unit (minus) Example Comparative Example 21 22 23 24 5 6 Dispersion No. One 2 3 4 5 6 The colorant (A) (A-II-5) 10.0 (A-II-10) 10.0 (A-II-11) 10.0 (A-II-12) 10.0 (A-X-1) 10.0 (A-X-2) 10.0 Dispersant Dispersant 1 18.4 18.4 18.4 18.4 18.4 18.4 Dispersion resin Dispersion resin 1 5.7 5.7 5.7 5.7 5.0 5.7 Solvent (E) (E-1) 165.9 165.9 165.9 165.9 165.9 165.9

In Table 17, each component represents the following compound.

(A-II-5): A compound represented by the formula (A-II-5)

(A-II-10): A compound represented by the formula (A-II-10)

(A-II-11): A compound represented by the formula (A-II-11)

(A-II-12): A compound represented by the formula (A-II-12)

(A-X-1): A compound represented by the formula (A-X-1)

(A-X-2): A compound represented by the formula (A-X-2)

Dispersant 1: DISPERBYK-162 (propylene glycol monomethyl ether acetate solution having a solid content of 38%)

Dispersion Resin 1: Propylene glycol monomethyl ether acetate solution (solid content 35.1%) of Resin (B-2)

(E-1): Propylene glycol monomethyl ether acetate

Production method of colored curable resin composition

The components shown in Table 18 were mixed to obtain a colored curable resin composition.

The unit (sub) Example Comparative Example 21 22 23 24 25 26 Dispersion Dispersion 1 15 Dispersion 2 15 Dispersion 3 15 Dispersion 4 15 Dispersion 5 15 Dispersion 6 15 Resin (B) (B-1) 3.5 3.5 3.5 3.5 3.5 3.5 The polymerizable compound (C) (C-1) 2.0 2.0 2.0 2.0 2.0 2.0 Polymerization initiator (D) (D-1) 0.5 0.5 0.5 0.5 0.5 0.5 Solvent (E) (E-1) 18 18 18 18 18 18 Leveling agent (F) (F-1) 0.09 0.09 0.09 0.09 0.09 0.09

In Table 18, each component represents the following compound.

(B-1): Resin (B-1) (in terms of solid content)

(C-1): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nihon Kayaku Co., Ltd.)

(Irgacure (registered trademark) OXE-01 manufactured by BASF), O-acyloxime (D-1) compound)

(E-1): Propylene glycol monomethyl ether acetate

(F-1): polyether-modified silicone oil (in terms of solid content)

(Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.)

Measurement of voltage holding ratio

The above-mentioned colored curable resin composition was coated on a glass substrate (# 1737; Corning) having a 3-inch square by spin coating, and then prebaked at 100 ° C for 3 minutes to form a colored composition layer. After cooling, the substrate was exposed using an exposure apparatus (TME-150 RSK; manufactured by Topcon Co., Ltd.) at an exposure amount of 150 mJ / cm ² (365 nm standard) in an air atmosphere. Also, no photomask was used. The exposed coloring composition layer was subjected to post-baking in an oven at 230 캜 for 20 minutes to prepare a coating film (film thickness: 2.0 탆). This coating film was scraped from the glass substrate to obtain a powder. 0.025 g of the obtained powder and 1 g of liquid crystal (MCL-6608, manufactured by Merck Co., Ltd.) were mixed and heated in a sample bottle at 120 캜 for 50 minutes. The mixture was transferred to a centrifuge tube and subjected to centrifugation twice for 30 minutes with MICRO SIX (manufactured by Asuzo Co., Ltd.). The upper portion of the mixture was sealed in a liquid crystal evaluation cell (KSRT-05 / BIIIMINTS 05X, manufactured by EHC Co., Ltd.), and the liquid crystal property evaluation device (Model 6254 manufactured by Toyo Techno Co., Ltd.) Were measured and evaluated based on the following criteria.

Measuring conditions

Applied voltage Pulse amplitude: 5V

* Voltage maintenance ratio: potential difference of the liquid crystal cell after 1000 milliseconds / value of voltage applied at 0 milliseconds

Evaluation standard

A: 95% or more

B: 85% or more and less than 95%

C: Less than 85%

coloring agent compound Voltage holding ratio Example 21 (A-II-5) A Example 22 (A-II-10) A Example 23 (A-II-11) A Example 24 (A-II-12) A Comparative Example 5 (A-X-1) C Comparative Example 6 (A-X-2) C

The compound of the present invention is excellent in absorbance and voltage retention, and a color filter excellent in solvent resistance can be produced by using the coloring composition using the compound.

Claims (6)

A compound represented by the formula (AI).
[Chemical Formula 1]

[In the formula (AI)
R ⁴¹ to R ⁴⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an aralkyl group having 7 to 30 carbon atoms and may have a substituent, substituent group which may have an aromatic hydrocarbon group and the aralkyl group is -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f may be, include groups wherein the saturated hydrocarbon in the saturated hydrocarbon group of 1 to 20 carbon atoms wherein May be substituted with a substituted or unsubstituted amino group or a halogen atom, and when the number of carbon atoms in the saturated hydrocarbon group is 2 to 20, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or -CO- . However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, the adjacent methylene group is not simultaneously substituted with an oxygen atom, and the terminal methylene group is not substituted with an oxygen atom or -CO-. R ⁴¹ and R ⁴² may bond to form a ring together with the nitrogen atom to which they are bonded, and R ⁴³ and R ⁴⁴ may bond to form a ring together with the nitrogen atom to which they are attached.
R ⁴⁷ ~ R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy _{^{group, -SO 3 -, -SO 2 -N}} - -SO 2 -R f , or an alkyl group having 1 to 8 carbon atoms, the alkyl group The constituting methylene group may be substituted with an oxygen atom or -CO-, and R ⁴⁸ and R ⁵² may combine with each other to form -NH-, -S-, or -SO ₂ -. However, adjacent methylene groups in the alkyl group are not simultaneously substituted with oxygen atoms, and the terminal methylene group is not substituted with an oxygen atom or -CO-.
The ring T ¹ represents an aromatic heterocycle having 3 to 10 carbon atoms, and the aromatic heterocycle has a saturated hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted amino group, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent . Substituent group which may have the aromatic hydrocarbon is -SO ₃ ^- can be a -SO ₂ -R ^{f -} or -SO ₂ -N.
M ^{r +} represents a hydrogen ion, a metal ion of r, or a substituted or unsubstituted ammonium ion.
k is a -SO ₃ with a compound represented by formula (AI) ^- represents the sum of the number of -SO ₂ -R ^{f -,} and -SO ₂ -N number of.
r represents an integer of 1 or more.
R ^f represents a fluoroalkyl group having 1 to 12 carbon atoms.
However, the compound represented by formula (AI) is -SO ₂ -N ^- -SO ₂ has at least one of -R ^f]. 2. The compound according to claim 1, wherein M ^&lt; ^r &gt; ⁺ is an r-valent metal ion. The method according to claim 1,
Wherein the aromatic heterocycle represented by T ¹ is a ring represented by the following formula (A-t1).
(2)

[In the formula (A-t1)
The ring T ² represents an aromatic heterocycle having 3 to 10 carbon atoms.
R ⁴⁵ and R ⁴⁶ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 7 to 30 carbon atoms And when the number of carbon atoms in the saturated hydrocarbon group is 2 to 20, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or -CO-. However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, the adjacent methylene group is not simultaneously substituted with an oxygen atom, and the terminal methylene group is not substituted with an oxygen atom or -CO-. R ⁴⁵ and R ⁴⁶ may combine to form a ring together with the nitrogen atom to which they are attached.
R ⁵⁵ represents a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms and may have a substituent.
k1 represents 0 or 1;
* Represents the bonding position with the carbanion.] A coloring composition comprising a compound according to any one of claims 1 to 3. A color filter formed from the coloring composition according to claim 4. A display device comprising the color filter according to claim 5.