CN113444380B

CN113444380B - Compound, colorant and colored resin composition

Info

Publication number: CN113444380B
Application number: CN202110301202.XA
Authority: CN
Inventors: 滨木裕史; 尹钟元
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2020-03-26
Filing date: 2021-03-22
Publication date: 2024-02-20
Anticipated expiration: 2041-03-22
Also published as: CN113444380A; JP2021155712A; KR20210120878A; TW202142539A

Abstract

The invention provides a colored resin composition capable of forming a color filter with excellent light resistance, a colorant contained in the colored resin composition, and a benzoperylene compound which is useful as a dye. A colorant comprising at least 2 kinds of compounds represented by the formula (I), wherein the 2 kinds of compounds represented by the formula (I) are each at least R of the formula (I) ¹ Compounds different from each other.

Description

Compound, colorant and colored resin composition

Technical Field

The present invention relates to a benzoperylene compound useful as a dye, a colorant containing the benzoperylene compound, and a colored resin composition containing the benzoperylene compound as a colorant.

Background

The colored resin composition is used for manufacturing color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays. Such a colored resin composition contains a colorant for obtaining a desired color tone or the like, and a perylene compound represented by the following formula (x) is known as a colorant (non-patent document 1).

Prior art literature

Non-patent literature

Non-patent document 1: BASF Protect (Lumogen (registered trademark) F), BASF, 1997, month 11, 2-6

Disclosure of Invention

However, the present inventors have studied and as a result, have found that the light resistance of a color filter formed from a colored resin composition using the above-mentioned perylene compound as a colorant, which has been conventionally known, is not sufficiently satisfactory. Accordingly, an object of the present invention is to provide a colored resin composition capable of forming a color filter excellent in light resistance, a colorant contained in the colored resin composition, and a benzoperylene compound useful as a dye.

The gist of the present invention is as follows.

[1] A colorant comprising at least 2 kinds of compounds represented by the formula (I),

the 2 compounds represented by the formula (I) are at least R of the formula (I) ¹ Compounds different from each other.

In the formula (I) of the formula (I),

R ¹ and R is ² Independently of each other, represents a C1-30 hydrocarbon group which may have a substituent, and the-CH contained in the hydrocarbon group ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-.

R ³ And R is ⁸ Independently of each other, represents a C1-30 hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent and which may have a C1-30 aromatic heterocyclic group, or a combination thereof, wherein the hydrocarbon group contains-CH ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-.

R ⁴ 、R ⁵ 、R ⁶ 、R ⁷ 、R ⁹ And R is ¹⁰ Independently of one another, represent a hydrogen atom, -R ¹¹ A halogen atom, a hydroxyl group, a carboxyl group or a nitro group.

R ⁴ And R is R ⁵ 、R ⁵ And R is R ⁶ And R is ⁶ And R is R ⁷ Can be bonded to each other to form-R ¹² －CO－O－CO－R ¹³ -or-R ¹² －CO－N(R ¹¹ )－CO－R ¹³ -a group represented.

R ¹¹ Represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and the-CH contained in the hydrocarbon group ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-. R is R ¹¹ When plural, they may be the same or different from each other.

R ¹² And R is ¹³ Independently of one another, represents a single bond or a C1-15 hydrocarbon group which may have a substituent, and the-CH contained in the hydrocarbon group which has 2 ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-. R is R ¹² When plural, they may be the same or different from each other, R ¹³ When plural, they may be the same or different from each other.]

[2] The colorant according to [1], wherein at least the combination of (I) the compound represented by the formula (Ia) and the compound represented by the formula (Ib), (ii) the combination of the compound represented by the formula (Ia) and the compound represented by the formula (Ic), or (iii) the combination of the compound represented by the formula (Ib) and the compound represented by the formula (Ic) contains at least 2 compounds selected from the group consisting of the compound represented by the formula (Ia), the compound represented by the formula (Ib) and the compound represented by the formula (Ic) as the compound represented by the formula (I).

[ in formula (Ia), formula (Ib) and formula (Ic),

R ^1a 、R ^2a 、R ^1b and R is ^1c Independently of each other, represents a C1-30 hydrocarbon group which may have a substituent, and the-CH contained in the hydrocarbon group ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-. Wherein R is ^1a And R is R ^2a Different, R ^1b And R is R ^1c Are not identical.

R ³ ～R ¹⁰ The same meaning as described above is indicated.]

[3] The colorant according to [2], wherein at least one of the combination of the compound represented by the formula (Ia) and the compound represented by the formula (Ib) and the combination of the compound represented by the formula (Ia) and the compound represented by the formula (Ic) is satisfied,

when the compound represented by the formula (Ia) satisfies (i) in combination with the compound represented by the formula (Ib), R of the formula (Ia) ^1a R with formula (Ib) ^1b The same is true of the fact that,

when the compound represented by the formula (Ia) satisfies (ii) in combination with the compound represented by the formula (Ic), R of the formula (Ia) ^2a R of formula (Ic) ^1c The same applies.

[4] The colorant according to [2] or [3], wherein at least 1 compound represented by the formula (Ia), at least 1 compound represented by the formula (Ib) and at least 1 compound represented by the formula (Ic), respectively,

of the total amount of the compound represented by the formula (Ia), the compound represented by the formula (Ib) and the compound represented by the formula (Ic),

the content of the compound represented by the formula (Ia) is 35 to 65 mol%,

The content of the compound represented by the formula (Ib) is 15 to 35 mol%,

the content of the compound represented by the formula (Ic) is 15 to 35 mol%.

[5] The colorant according to any one of [1] to [4], wherein a perylene compound is further contained.

[6] A colored resin composition comprising the colorant of any one of [1] to [5] and a resin.

[7] The colored resin composition according to [6], wherein the colored resin composition further comprises a polymerizable compound and a polymerization initiator.

[8] The colored resin composition according to [6] or [7], wherein a solvent is further contained.

[9] A color filter formed from the colored resin composition described in any one of [6] to [8 ].

[10] A display device comprising the color filter of [9 ].

[11] A compound represented by formula (Ia).

In the formula (Ia),

R ^1a and R is ^2a Independently of each other, represents a C1-30 hydrocarbon group which may have a substituent, and the-CH contained in the hydrocarbon group ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-. However, R is ^1a And R is R ^2a Are not identical.

R ³ And R is ⁸ Independently of each other, represents a C1-30 hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent and which may have a C1-30 aromatic heterocyclic group, or a combination thereof, wherein the hydrocarbon group contains-CH ₂ -and-CH contained in the combined groups ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-.

According to the present invention, there are provided a colored resin composition, a colorant and a compound which can be used for forming a color filter having more excellent light resistance than conventional colored resin compositions containing a perylene compound as a colorant.

Detailed Description

The colorant of the present invention (hereinafter, sometimes referred to as colorant (A)) contains at least 2 compounds represented by the formula (I) (hereinafter, sometimes referred to as compound (I)), and the 2 compounds (I) are each at least R of the formula (I) ¹ Compounds different from each other.

< Compound (I) >)

In the formula (I) of the formula (I),

R ¹ and R is ² Independently of each other, represents a hydrocarbon group of 1 to 30 carbon atoms which may have a substituent (A1), and the-CH contained in the hydrocarbon group ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-.

R ³ And R is ⁸ Independently of each other, represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1), an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent (A1), or a combination thereof, wherein the hydrocarbon group contains-CH ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-.

R ¹¹ Represents a hydrocarbon group of 1 to 30 carbon atoms which may have a substituent (A1), and the-CH contained in the hydrocarbon group ₂ -cocoaSubstituted by-O-, -CO-, -OCO-or-COO-. R is R ¹¹ When plural, they may be the same or different from each other.

R ¹² And R is ¹³ Independently of one another, represents a single bond or a C1-15 hydrocarbon group which may have a substituent (A1), and the-CH contained in the hydrocarbon group having 2 ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-. R is R ¹² When plural, they may be the same or different from each other, R ¹³ When plural, they may be the same or different from each other.]

As R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ Examples of the hydrocarbon group having 1 to 30 carbon atoms include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain-like or alicyclic.

As R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ Examples of the saturated or unsaturated chain hydrocarbon group include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and eicosyl groups; branched alkyl groups such as isopropyl, (1-ethyl) propyl, isobutyl, sec-butyl, tert-butyl, (3-methyl) butyl, (1-ethyl) butyl, (2-ethyl) butyl, (1-propyl) butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl) pentyl, (3-methyl) pentyl, (1-ethyl) pentyl, (2-ethyl) pentyl, (3-ethyl) pentyl, (1-propyl) pentyl, (1-butyl) pentyl, isohexyl, (5-methyl) hexyl, (1-ethyl) hexyl, (2-ethyl) hexyl, (1-butyl) hexyl, (1-pentyl) hexyl, (3-ethyl) heptyl, (1-hexyl) heptyl, (1-heptyl) octyl, and (1-octyl) nonyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl. Carbon of saturated chain hydrocarbon radical The number of atoms is preferably 1 to 25, more preferably 1 to 20, and still more preferably 1 to 15. The number of carbon atoms of the unsaturated chain hydrocarbon group is preferably 2 to 25, more preferably 2 to 20, and still more preferably 2 to 15.

As R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ Examples of the saturated or unsaturated alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohexane-2-ene, cyclohexane-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]Octyl, and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 25, more preferably 3 to 20, and still more preferably 3 to 15.

As R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ Examples of the aromatic hydrocarbon group include phenyl, 1-naphthyl, 2-naphthyl, phenanthryl, anthracyl, and pyrenyl. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 25, more preferably 6 to 20, and even more preferably 6 to 15.

R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ The hydrocarbyl group represented by the above may be a group formed by combining 2 or more of the chain hydrocarbyl group, alicyclic hydrocarbyl group, and aromatic hydrocarbyl group, as long as the upper limit of the number of carbon atoms is 30 or less. Such a group may be, for example, a group obtained by combining an aromatic hydrocarbon group with at least one group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group and an aromatic hydrocarbon group, and the chain hydrocarbon group may be combined as a 2-valent group (for example, alkanediyl group) in the hydrocarbon group based on the combination. Examples of the hydrocarbon group based on the combination include aralkyl groups such as benzyl, phenethyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 2-naphthylmethyl and the like; aryl alkenyl groups such as phenyl vinyl (phenyl vinyl); arylalkynyl such as phenylethynyl; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2, 3-dimethylphenyl, 2, 4-dimethylphenyl, 2, 5-dimethylphenyl, 2, 6-dimethylphenyl, 3, 4-dimethylphenyl, 3, 5-di-dimethylphenyl Alkylaryl groups such as methylphenyl, 2,4, 6-trimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2, 3-diisopropylphenyl, 2, 4-diisopropylphenyl, 2, 5-diisopropylphenyl, 2, 6-diisopropylphenyl, 3, 5-diisopropylphenyl, 2,4, 6-triisopropylphenyl, 4-butylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 2, 6-di-tert-butylphenyl, 3, 5-di-tert-butylphenyl, 3, 6-di-tert-butylphenyl, 4-tert-butyl-2, 6-dimethylphenyl, 4-pentylphenyl, 4-octylphenyl, 4- (2, 4-trimethyl-2-pentyl) phenyl, 2-dodecylphenyl, 3-dodecylphenyl and 4-dodecylphenyl; aryl groups bonded to alkanediyl such as 2, 3-dihydro-4-indenyl, 1,2,3,5,6, 7-hexahydro-4-s-dicyclopentadienophenyl, 8-methyl-1, 2,3,5,6, 7-hexahydro-4-s-dicyclopentadienophenyl, 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, 3-methyl-5, 6,7, 8-tetrahydro-2-naphthyl, and 3,5, 8-pentamethyl-5, 6,7, 8-tetrahydro-2-naphthyl; aryl bonded by more than one aryl group such as biphenyl and terphenyl; cyclohexylmethylphenyl, benzyl phenyl, (dimethyl (phenyl) methyl) phenyl, and the like. The hydrocarbon group may be, for example, a hydrocarbon group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, and as an example thereof, examples thereof include 1-methylcyclopropyl, 2-methylcyclopentyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, 2,4, 6-trimethylcyclohexyl alicyclic hydrocarbon groups having 1 or more alkyl groups bonded thereto, such as 2, 6-tetramethylcyclohexyl, 3, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl, and 4-cyclohexylcyclohexyl; cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl Alkyl groups in which 1 or more alicyclic hydrocarbon groups such as a group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group, and adamantylmethyl group are bonded to each other. The number of carbon atoms of the group obtained by combining 2 or more chain hydrocarbon groups, alicyclic hydrocarbon groups and aromatic hydrocarbon groups is preferably 4 to 28, more preferably 5 to 25, and still more preferably 6 to 20.

R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ Represented by-CH contained in hydrocarbon group ₂ -is replaced by-O-, -CO-; when OCO-or-COO-, the number of the elements may be 1 or 2 or more. the-CH group contained in the hydrocarbon group ₂ -is replaced by-O-, -CO-; when OCO-or-COO-, the number of carbon atoms before substitution is calculated as the number of carbon atoms of the hydrocarbon group. As R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ Represented by-CH contained in hydrocarbon group ₂ -is replaced by-O-, -CO-; -OCO-or-COO-, in particular, the method comprises the steps of, examples thereof include groups represented by the following formulas (Y-1) to (Y-25). * Represents the bonding site.

As R ¹² And R is ¹³ Examples of the 2-valent hydrocarbon group having 1 to 15 carbon atoms include R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ And a group having 1 hydrogen atom as a bonding site in the hydrocarbon group represented (excluding the examples having 16 or more carbon atoms). The number of carbon atoms of the 2-valent hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, and still more preferably 1 to 5. The 2-valent hydrocarbon group is preferably a 2-valent saturated chain hydrocarbon group, and more preferably a linear or branched alkanediyl group. Examples of the 2-valent hydrocarbon group include alkanediyl groups such as methylene, ethylene, propylene and butylene.

R ¹² And R is ¹³ Represented by-CH contained in a 2-valent hydrocarbon group ₂ Substitution of-O-, -CO-, -OCO-or-COO-may be 1 or 2 or more. the-CH group contained in the hydrocarbon group ₂ -is replaced by-O-, -CO-; when OCO-or-COO-, the number of carbon atoms before substitution is calculated as the number of carbon atoms of the 2-valent hydrocarbon group. As R ¹² And R is ¹³ Represented by-CH contained in a 2-valent hydrocarbon group ₂ -a group substituted by-O-, -CO-, -OCO-, or-COO-, in particular, the method comprises the steps of, examples of the group include those having 1 hydrogen atom contained in the groups represented by the above formulas (Y-1) to (Y-25) as a bonding site.

As R ³ And R is ⁸ Examples of the aromatic heterocyclic group having 1 to 30 carbon atoms include aromatic heterocyclic groups containing at least 1 heteroatom such as nitrogen atom, oxygen atom and sulfur atom. Specific examples of the aromatic heterocyclic group include furyl, pyrrolyl, thienyl,Oxazolyl, pyridyl, quinolinyl, thiazolyl, benzothiazolyl, carbazolyl, and the like. The number of carbon atoms of the aromatic heterocyclic group is preferably 2 to 25, more preferably 3 to 20, and still more preferably 3 to 15.

As R ³ And R is ⁸ The group in which the hydrocarbon group and the aromatic heterocyclic group are bonded may be a group in which 2 or more hydrocarbon groups and aromatic heterocyclic groups are bonded, and for example, at least 1 selected from the group consisting of a chain hydrocarbon group, an alicyclic hydrocarbon group and an aromatic hydrocarbon group may be bonded to an aromatic heterocyclic group, and the chain hydrocarbon group may be bonded as a 2-valent group (for example, alkanediyl group) among the groups in which the hydrocarbon group and the aromatic heterocyclic group are bonded. Examples of the group formed by bonding the hydrocarbon group to the aromatic heterocyclic group include a 2-methylpyridyl group, a 4-ethyl-2-methylpyridyl group, an indolyl group, a benzimidazolyl group, a benzofuranyl group, and a benzothienyl group. The number of carbon atoms of the group obtained by combining the above-mentioned hydrocarbon group and the above-mentioned aromatic heterocyclic group is preferably 4 to 30, more preferably 6 to 30, and still more preferably 10 to 30.

As R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ A hydrocarbon group having 1 to 30 carbon atoms, R ³ And R is ⁸ An aromatic heterocyclic group having 1 to 30 carbon atoms and R ¹² And R is ¹³ The substituent (A1) which the 2-valent hydrocarbon group having 1 to 15 carbon atoms may have is, for example, a halogen atom; a nitrile group; a nitro group; an amino group; a hydroxyl group; a thiol group; alkylthio groups having 1 to 20 carbon atoms such as methylthio and ethylthio; allylthio; arylthio groups having 6 to 20 carbon atoms such as phenylthio, 1-naphthylthio and 2-naphthylthio; sulfinyl; alkylsulfinyl groups having 1 to 20 carbon atoms such as methylsulfinyl and ethylsulfinyl; arylsulfinyl groups having 6 to 20 carbon atoms such as phenylsulfinyl group, 1-naphthylsulfinyl group and 2-naphthylsulfinyl group; a silyl group; an oxyboronyl group; alkylamino groups having 1 to 20 carbon atoms such as a monomethylamino group, a dimethylamino group, a trimethylamino group, a monoethylamino group, a diethylamino group and a triethylamino group; arylamino groups having 6 to 20 carbon atoms such as a monophenylamino group, a diphenylamino group and a triphenylamino group; aralkylamino groups having 7 to 20 carbon atoms such as benzylamino group; a carboxyl group; carbamoyl, and the like.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of synthesis, chlorine atoms and bromine atoms are preferable.

As R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ The hydrocarbon group having 1 to 30 carbon atoms which may have the substituent (A1) is specifically a group represented by the following formulae (D-1) to (D-37) and (G-1) to (G-24). * Represents the bonding site.

From the viewpoint of improving the light resistance of the obtained color filter, R is ¹ And R is ² It is preferable that each of the groups is independently a saturated chain hydrocarbon group which may have a substituent (A1), a group obtained by combining an aromatic hydrocarbon group which may have a substituent (A1) with a chain hydrocarbon group, or a group obtained by combining a chain hydrocarbon group which may have a substituent (A1) with an alicyclic hydrocarbon group, and it is preferable that-CH contained in the hydrocarbon group is selected from any of the groups ₂ -not substituted by-O-, -CO-, -OCO-, or-COO-. As R ¹ And R is ² More preferably, the groups are independently a saturated chain hydrocarbon group having 1 to 15 carbon atoms, a chain hydrocarbon group having 6 to 12 carbon atoms and a chain hydrocarbon group having 1 to 10 carbon atoms, or a chain hydrocarbon group having 1 to 10 carbon atoms and an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and still more preferably a saturated chain hydrocarbon group having 3 to 13 carbon atoms, a chain hydrocarbon group having 6 to 10 carbon atoms and a chain hydrocarbon group having 1 to 5 carbon atoms, or a chain hydrocarbon group having 1 to 5 carbon atoms and an alicyclic hydrocarbon group having 5 to 10 carbon atoms. Specifically, as R ¹ And R is ² The groups represented by any of the above-mentioned formulae (D-1) to (D-37) are preferable, the groups represented by any of the formulae (D-3) to (D-10) or (D-12) to (D-37) are more preferable, the groups represented by any of the formulae (D-4) to (D-9) or (D-22) to (D-37) are more preferable, and the groups represented by any of the formulae (D-5) to (D-8), the formulae (D-28) to (D-33) or (D-36) are more preferable.

From the viewpoint of improving the solubility of the compound (I) in a solvent, R is the group of ¹ And R is ² The hydrocarbon groups are preferably saturated chain hydrocarbon groups having 1 to 15 carbon atoms, more preferably saturated chain hydrocarbon groups having 3 to 13 carbon atoms, and even more preferably linear alkyl groups having 3 to 13 carbon atoms, independently of each other.

As R ¹ And R is ² May be the same or different, and preferably is different.

From the viewpoint of improving the light resistance of the obtained color filter, R is ³ And R is ⁸ Preferably independently of one another, may have a substituent (A1)The aromatic hydrocarbon group or the group obtained by combining the aromatic hydrocarbon group which may have the substituent (A1) with the chain hydrocarbon group is more preferably a group obtained by combining the aromatic hydrocarbon group which may have the substituent (A1) with the chain hydrocarbon group, still more preferably a group obtained by combining the aromatic hydrocarbon group with the saturated chain hydrocarbon group, still more preferably a group obtained by combining the aromatic hydrocarbon group having 6 to 12 carbon atoms with the saturated chain hydrocarbon group having 1 to 8 carbon atoms, and particularly preferably a group in which saturated chain hydrocarbon groups are bonded to each of the 2 ortho positions of the phenyl group. Specifically, as R ³ And R is ⁸ The groups represented by any of the above-mentioned formulas (G-1) to (G-24) are preferable, the groups represented by any of the formulas (G-1) to (G-15) are more preferable, the groups represented by any of the formulas (G-5) to (G-9), the formulas (G-12) or the formulas (G-14) are more preferable, and the groups represented by the formulas (G-8) are particularly preferable.

In addition, as R ³ And R is ⁸ The same or different, preferably the same.

As R ⁴ 、R ⁵ 、R ⁶ 、R ⁷ 、R ⁹ And R is ¹⁰ Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

As R ⁴ And R is R ⁵ 、R ⁵ And R is R ⁶ And R is ⁶ And R is R ⁷ Formed by bonding with each other by-R ¹² －CO－O－CO－R ¹³ Specifically, the group represented by the following formula (H-1) to formula (H-8) may be mentioned. * R represents ⁴ And R is R ⁵ 、R ⁵ And R is R ⁶ Or R is ⁶ And R is R ⁷ And a bonding site with a benzoperylene skeleton.

As R ⁴ And R is R ⁵ 、R ⁵ And R is R ⁶ And R is ⁶ And R is R ⁷ Formed by bonding with each other by-R ¹² －CO－N(R ¹¹ )－CO－R ¹³ Specifically, the group represented by the following formula (H-9) to formula (H-16) may be mentioned. * R represents ⁴ And R is R ⁵ 、R ⁵ And R is R ⁶ Or R is ⁶ And R is R ⁷ And a bonding site with a benzoperylene skeleton.

The group represented by the formula (H-9) is more specifically a group represented by the following formulas (H-9-1) to (H-9-16). * R represents ⁴ And R is R ⁵ 、R ⁵ And R is R ⁶ Or R is ⁶ And R is R ⁷ And a bonding site with a benzoperylene skeleton.

As R ⁴ 、R ⁵ 、R ⁶ 、R ⁷ 、R ⁹ And R is ¹⁰ Preferably a hydrogen atom. R is R ⁴ 、R ⁵ 、R ⁶ 、R ⁷ 、R ⁹ And R is ¹⁰ The compounds having the desired absorption wavelength and fluorescence wavelength can be obtained by appropriate combinations.

Specific examples of the compound (I) include compounds shown in table 1 below.

TABLE 1

R ¹

R ²

R ³

R4

R ⁵

R ⁶

R ⁷

R ⁸

R ⁹

R ¹⁰

(I-1)

D-5

G-8

H

G-8

H

(I-2)

D-5

D-6

G-8

H

G-8

H

(I-3)

D-5

D-7

G-8

H

G-8

H

(I-4)

D-5

D-8

G-8

H

G-8

H

(I-5)

D-5

D-29

G-8

H

G-8

H

(I-6)

D-5

D-30

G-8

H

G-8

H

(I-7)

D-5

D-31

G-8

H

G-8

H

(I-8)

D-5

D-33

G-8

H

G-8

H

(I-9)

D-5

D-36

G-8

H

G-8

H

(I-10)

D-6

G-8

H

G-8

H

(I-11)

D-6

D-7

G-8

H

G-8

H

(I-12)

D-6

D-8

G-8

H

G-8

H

(I-13)

D-6

D-29

G-8

H

G-8

H

(I-14)

D-6

D-30

G-8

H

G-8

H

(I-15)

D-6

D-31

G-8

H

G-8

H

(I-16)

D-6

D-33

G-8

H

G-8

H

(I-17)

D-6

D-36

G-8

H

G-8

H

(I-18)

D-7

G-8

H

G-8

H

(I-19)

D-7

D-8

G-8

H

G-8

H

(I-20)

D-7

D-29

G-8

H

G-8

H

(I-21)

D-7

D-30

G-8

H

G-8

H

(I-22)

D-7

D-31

G-8

H

G-8

H

(I-23)

D-7

D-33

G-8

H

G-8

H

(I-24)

D-7

D-36

G-8

H

G-8

H

(I-25)

D-8

G-8

H

G-8

H

(I-26)

D-8

D-29

G-8

H

G-8

H

(I-27)

D-8

D-30

G-8

H

G-8

H

(I-28)

D-8

D-31

G-8

H

G-8

H

(I-29)

D-8

D-33

G-8

H

G-8

H

(I-30)

D-8

D-36

G-8

H

G-8

H

(I-31)

D-29

G-8

H

G-8

H

(I-32)

D-29

D-30

G-8

H

G-8

H

(I-33)

D-29

D-31

G-8

H

G-8

H

(I-34)

D-29

D-33

G-8

H

G-8

H

(I-35)

D-29

D-36

G-8

H

G-8

H

(I-36)

D-30

G-8

H

G-8

H

(I-37)

D-30

D-31

G-8

H

G-8

H

(I-38)

D-30

D-33

G-8

H

G-8

H

(I-39)

D-30

D-36

G-8

H

G-8

H

(I-40)

D-31

G-8

H

G-8

H

(I-41)

D-31

D-33

G-8

H

G-8

H

(I-42)

D-31

D-36

G-8

H

G-8

H

(I-43)

D-33

G-8

H

G-8

H

(I-44)

D-33

D-36

G-8

H

G-8

H

(I-45)

D-36

G-8

H

G-8

H

In Table 1, H represents a hydrogen atom, and D-5, D-6, D-7, D-8, D-29, D-30, D-31, D-33, D-36 and G-8 represent groups represented by the above-mentioned formulae (D-5), (D-6), (D-7), (D-8), (D-29), formula (D-30), formula (D-31), formula (D-33), formula (D-36) and formula (G-8), respectively.

From the viewpoint of improving the light resistance of the obtained color filter, the compound (I) is preferably a compound (I-1) to a compound (I-45), more preferably a compound (I-2) to a compound (I-9), a compound (I-11) to a compound (I-17), a compound (I-19) to a compound (I-24), a compound (I-26) to a compound (I-30), a compound (I-32) to a compound (I-35), a compound (I-37) to a compound (I-39), a compound (I-41), a compound (I-42) or a compound (I-44).

< colorant (A) >)

As the colorant (A), at least 2 compounds (I) are contained, and the 2 compounds (I) are at least R of the formula (I) ¹ Compounds different from each other. R of formula (I) of the above 2 compounds (I) ² May be the same as or different from each other. In addition, R of formula (I) of the above 2 compounds (I) ³ ～R ¹⁰ Each independently of the other, and may be the same or different from each other, preferably R ³ ～R ¹⁰ From 4 to 8 of them being identical to one another, more preferably R ³ ～R ¹⁰ From 6 to 8 of them being identical to one another, preferably R ³ ～R ¹⁰ Are identical to each other. The number of the compounds (I) contained in the colorant (a) is preferably 2 to 6, more preferably 2 to 5, and still more preferably 2 to 4.

For the compound (I) of 2 or more kinds contained as the colorant (a), it is preferable that at least 2 kinds of compounds selected from the group consisting of the compound (hereinafter, sometimes referred to as compound (Ia)) represented by the following formula (Ia)) and the compound (hereinafter, sometimes referred to as compound (Ib)), the compound (hereinafter, sometimes referred to as compound (Ib)) represented by the following formula (Ia), the compound (hereinafter, sometimes referred to as compound (Ic)) represented by the following formula (Ic)) and the compound (hereinafter, sometimes referred to as compound (Ic)) are contained.

Compound (Ia), compound (Ib), compound (Ic) >)

[ in formula (Ia), formula (Ib) and formula (Ic),

R ^1a 、R ^2a 、R ^1b and R is ^1c Independently of each other, represents a hydrocarbon group of 1 to 30 carbon atoms which may have a substituent (A5), and the-CH contained in the hydrocarbon group ₂ Can be substituted by-O-, -CO-, -OCO-or-COO-. Wherein R is ^1a And R is R ^2a Different, R ^1b And R is R ^1c Are not identical.

R ³ ～R ¹⁰ The same meaning as described above is indicated.]

2R in formula (Ib) ^1b 2R in formula (Ic) are the same group ^1c Are the same groups.

As R ^1a 、R ^2a 、R ^1b And R is ^1c Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by the formula (I) include R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ The same examples of the hydrocarbon groups are shown, and the preferred ranges of the number of carbon atoms are also the same.

R ^1a 、R ^2a 、R ^1b And R is ^1c Represented by-CH contained in hydrocarbon group ₂ -is replaced by-O-, -CO-; when OCO-or-COO-, the number of the elements may be 1 or 2 or more. the-CH group contained in the hydrocarbon group ₂ -is replaced by-O-, -CO-; when OCO-or-COO-, the number of carbon atoms before substitution is calculated as the number of carbon atoms of the hydrocarbon group. As R ^1a 、R ^2a 、R ^1b And R is ^1c Represented by-CH contained in hydrocarbon group ₂ -a group substituted by-O-, -CO-, -OCO-, or-COO-, R is as follows ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ Represented by-CH contained in hydrocarbon group ₂ -is replaced by-O-, -CO-; the same examples of-OCO-or-COO-groups.

As R ^1a 、R ^2a 、R ^1b And R is ^1c Examples of the substituent (A5) which may be present in the hydrocarbon group having 1 to 30 carbon atoms represented by the formula (I) include R ¹ 、R ² 、R ³ 、R ⁸ And R is ¹¹ Examples of the substituent (A1) which may be present in the hydrocarbon group having 1 to 30 carbon atoms are the same.

From the viewpoint of improving the light resistance of the obtained color filter, R is ^1a 、R ^2a 、R ^1b And R is ^1c Preferably, the groups are, independently of each other, a saturated chain hydrocarbon group which may have a substituent (A5), a group obtained by combining an aromatic hydrocarbon group which may have a substituent (A5) with a chain hydrocarbon group, or a group obtained by combining a chain hydrocarbon group which may have a substituent (A5) with an alicyclic hydrocarbon group, and the-CH contained in the hydrocarbon group in any of the groups ₂ All preferably not replaced by-O-; -CO-, -OCO-or-COO-. As R ^1a 、R ^2a 、R ^1b And R is ^1c More preferably, the groups are independently a saturated chain hydrocarbon group having 1 to 15 carbon atoms, a chain hydrocarbon group having 6 to 12 carbon atoms and a chain hydrocarbon group having 1 to 10 carbon atoms, or a chain hydrocarbon group having 1 to 10 carbon atoms and an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and still more preferably a saturated chain hydrocarbon group having 3 to 13 carbon atoms, a chain hydrocarbon group having 6 to 10 carbon atoms and a chain hydrocarbon group having 1 to 5 carbon atoms, or a chain hydrocarbon group having 1 to 5 carbon atoms and an alicyclic hydrocarbon group having 5 to 10 carbon atoms. In addition, from the viewpoint of improving the solubility of the compound (I) in a solvent, R is ^1a 、R ^2a 、R ^1b And R is ^1c The hydrocarbon groups are preferably saturated chain hydrocarbon groups having 1 to 15 carbon atoms, more preferably saturated chain hydrocarbon groups having 3 to 13 carbon atoms, and even more preferably linear alkyl groups having 3 to 13 carbon atoms, independently of each other. Specifically, as R ^1a 、R ^2a 、R ^1b And R is ^1c The groups represented by any of the above-mentioned formulae (D-1) to (D-37) are preferable, the groups represented by any of the formulae (D-3) to (D-10) or (D-12) to (D-37) are more preferable, the groups represented by any of the formulae (D-4) to (D-9) or (D-22) to (D-37) are more preferable, and the groups represented by any of the formulae (D-5) to (D-8), the formulae (D-28) to (D-33) or (D-36) are more preferable.

R in formula (Ia) ^1a And R is ^2a The distinction of (2) is determined according to the following discrimination criteria.

Priority discrimination reference 1: the larger one of the formula weights is defined as R ^1a

Priority 2 discrimination criteria: will-CH ₂ One of a larger number of- ^1a

Priority 3 discrimination criteria: will-CH ₃ One of the larger number of R ^1a

For example, in the case of the above-mentioned compound (I-2), the pentyl group as the group represented by the formula (D-5) is R of the formula (Ia) ^2a The hexyl group as the group represented by the formula (D-6) is R of the formula (Ia) ^1a 。

R in formula (Ib) and formula (Ic) ^1b And R is ^1c The distinction of (2) is determined according to the following discrimination criteria.

Priority discrimination reference 1: the larger one of the formula weights is defined as R ^1b

Priority 2 discrimination criteria: will-CH ₂ One of a larger number of- ^1b

Priority 3 discrimination criteria: will-CH ₃ One of the larger number of R ^1b

For example, in the case of the above-mentioned compound (I-1) and compound (I-10), the pentyl group as the group represented by the formula (D-5) of the compound (I-1) is R of the formula (Ic) ^1c (that is, the compound (I-1) corresponds to the compound (Ic)), and the hexyl group as the group represented by the formula (D-6) of the compound (I-10) is R of the formula (Ib) ^1b (i.e., compound (I-10) corresponds to compound (Ib)).

When at least 2 compounds selected from the group consisting of the compound (Ia), the compound (Ib) and the compound (Ic) are contained as the colorant (a) so as to satisfy at least one of the combination of (i) and the combination of (ii), when the colorant (a) is contained so as to satisfy the combination of (i), R of the formula (Ia) is preferable ^1a R with formula (Ib) ^1b Similarly, when the compounds satisfy the combination of (ii), R of formula (Ia) is preferable ^2a R of formula (Ic) ^1c The same applies.

For example, when the compound (Ia) is the above-mentioned compound (I-2), if the colorant (A) contains a combination of the compound (Ia) and the compound (Ib), the above-mentioned compound (I-10) is preferable as the compound (Ib). In addition, for example, when the compound (Ia) is the above-mentioned compound (I-2), if the colorant (A) contains a combination of (ii) the compound (Ia) and the compound (Ic), the above-mentioned compound (I-1) is preferable as the compound (Ic).

When at least 2 compounds selected from the group consisting of the compound (Ia), the compound (Ib) and the compound (Ic) are contained as the colorant (a) so as to satisfy the combination of the above (i), the content of the compound (Ia) is preferably 45 to 85 mol%, more preferably 50 to 80 mol%, still more preferably 55 to 75 mol% in the total amount of the compound (Ia) and the compound (Ib).

When at least 2 compounds selected from the group consisting of the compound (Ia), the compound (Ib) and the compound (Ic) are contained as the colorant (a) so as to satisfy the combination of the above (ii), the content of the compound (Ia) is preferably 45 to 85 mol%, more preferably 50 to 80 mol%, and even more preferably 55 to 75 mol% in the total amount of the compound (Ia) and the compound (Ic).

When at least 2 compounds selected from the group consisting of the compound (Ia), the compound (Ib) and the compound (Ic) are contained as the colorant (a) so as to satisfy the combination of the above (iii), the content of the compound (Ib) is preferably 35 to 65 mol%, more preferably 40 to 60 mol%, still more preferably 45 to 55 mol% in the total amount of the compound (Ib) and the compound (Ic).

R as the colorant (A) is contained in the formula (I) ¹ From the viewpoint of the colorant (A) of at least 2 compounds (I) different from each other, it is preferable that the compound (Ia), the compound (Ib) and the compound (Ic) each contain at least 1 or more, more preferably R of the formula (Ia) ^1a R with formula (Ib) ^1b R of the same and formula (Ia) ^2a R of formula (Ic) ^1c In the same manner, the compound (Ia), the compound (Ib) and the compound (Ic) each contain at least 1 or more.

In addition, as the colorant (a), it is preferable that the compound (Ia) is not contained and the compound (Ib) and the compound (Ic) are contained in at least 1 or more, respectively, from the viewpoint of easy control of the content of each compound (I) in the colorant (a).

When the compound (Ia), the compound (Ib) and the compound (Ic) are contained in the colorant (a) in an amount of 1 or more, the content of the compound (Ia) is preferably 35 to 65 mol%, more preferably 40 to 60 mol%, still more preferably 45 to 55 mol% based on the total amount of the compound (Ia), the compound (Ib) and the compound (Ic).

When the compound (Ia), the compound (Ib) and the compound (Ic) are contained in 1 or more of the colorant (a), the content of the compound (Ib) and the compound (Ic) is preferably 15 to 35 mol%, more preferably 18 to 32 mol%, and even more preferably 20 to 30 mol% in the total amount of the compound (Ia), the compound (Ib) and the compound (Ic), respectively.

When the compound (Ia), the compound (Ib) and the compound (Ic) are contained in the colorant (a) in an amount of 1 or more, the content ratio of the compound (Ib) to the compound (Ic) (compound (Ib)/compound (Ic)) is preferably 0.80 to 1.20, more preferably 0.85 to 1.15, and even more preferably 0.87 to 1.13 on a molar basis.

As the compound (I), the compound (Ia) is particularly preferable.

The compound (I) can be produced, for example, by reacting a compound represented by the following formula (pt 1) with maleic anhydride in the presence of a dehydrogenation agent to produce a compound represented by the following formula (pt 1-1), and reacting a compound represented by the following formulas (MA 1-1), (MA 2-1) and (MA 2-2) with the compound represented by the following formula (pt 1-1) in a solvent in the presence of a base. R in the following formula ¹ And R is R ² Meanwhile, the compound represented by the formula (I) 'and the compound represented by the formula (I)' may be produced simultaneously with the compound represented by the formula (I). For example, R ¹ Is of formula (I) greater than R ² In the case of the formula (a), the compound represented by the formula (I) corresponds to the above-mentioned compound (Ia), the compound represented by the formula (I)' corresponds to the above-mentioned compound (Ib), and the compound represented by the formula (I) "corresponds to the compound (Ic).

[ typeWherein R is ¹ ～R ¹⁰ The same definition as above. X is X ¹ And X ² Independently of each other, represent a halogen atom.]

As the compound represented by the formula (pt 1), for example, N ¹ ,N ² Bis (2, 6-diisopropylphenyl) perylene-3, 4,9, 10-tetracarboxylic acid diimide, etc.

The amount of maleic anhydride to be used is usually 1 to 1000 moles, preferably 1 to 800 moles, more preferably 1 to 600 moles, still more preferably 1 to 400 moles, based on 1 mole of the compound represented by the formula (pt 1).

The dehydrogenation agent is a substance that causes the hydrogen of the 6-membered ring compound to be released and to be aromatic. The dehydrogenating agent is preferably tetrachloro-p-benzoquinone, 2, 5-dichloro-p-benzoquinone, 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone, tetramethyl-p-benzoquinone, 2, 5-diphenyl-p-benzoquinone, tetrabromo-p-benzoquinone, more preferably tetrachloro-p-benzoquinone, 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone.

The reaction temperature at which maleic anhydride is reacted with the compound represented by the formula (pt 1) is usually-100℃to 300 ℃. The reaction time for reacting maleic anhydride with the compound represented by the formula (pt 1) is usually 0.5 to 500 hours.

As X ¹ And X ² Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a bromine atom or an iodine atom is preferable.

As the compound represented by the formula (MA 1-1), the formula (MA 2-1) may be mentioned, for example, 1-pentanol, 1-hexanol, 2-ethylhexanol, 1-heptanol, 1-octanol, benzyl alcohol, cyclohexane methanol and the like.

Examples of the compounds represented by the formulae (MA 1-2) and (MA 2-2) include 1-bromopentane, 1-iodopentane, 1-bromohexane, 1-iodohexane, 1-bromo-2-ethylhexane, 1-iodo-2-ethylhexane, 1-bromoheptane, 1-iodoheptane, 1-bromooctane, 1-iodooctane, benzyl bromide, benzyl iodide, cyclohexylmethyl bromide, and cyclohexylmethyl iodide.

The amount of the compound represented by the formula (MA 1-1), the formula (MA 1-2), the formula (MA 2-1) and the formula (MA 2-2) to be used is usually 1 to 20 mol, preferably 1 to 10 mol or less, based on 1 mol of the compound represented by the formula (pt 1-1) independently of each other. The total amount of the compounds represented by the formulas (MA 1-1), (MA 1-2), (MA 2-1) and (MA 2-2) is usually 5 to 50 moles, preferably 10 to 35 moles, relative to 1 mole of the compound represented by the formula (pt 1-1).

Examples of the base used in the reaction of the compound represented by the formula (pt 1-1) with the compound represented by the formula (MA 1-1), the formula (MA 1-2), the formula (MA 2-1) and the formula (MA 2-2) include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, piperidine, 1, 8-diazabicyclo [5.4.0] undecene, 1, 5-diazabicyclo [4.3.0] nonene, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium t-butoxide, potassium t-butoxide, organic metal compounds such as methyl lithium, butyl lithium, t-butyl lithium and phenyl lithium, inorganic bases such as sodium hydrogencarbonate, potassium hydrogencarbonate, sodium carbonate, potassium hydroxide, lithium hydroxide, sodium hydroxide and potassium hydroxide, and the like, and organic bases are preferable.

The amount of the base to be used is usually 0.1 to 100 mol, preferably 1 to 40 mol, based on 1 mol of the compound represented by the formula (pt 1-1).

Examples of the solvent in the reaction of the compound represented by the formula (pt 1-1) with the compound represented by the formula (MA 1-1), the formula (MA 1-2), the formula (MA 2-1) and the formula (MA 2-2) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1, 2-dichlorobenzene; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, carboxylic acid solvents such as acetic acid, propionic acid, butyric acid, and the like, imidazole, and the like, are preferably amide solvents, and more preferably N, N-dimethylformamide.

The amount of the solvent to be used is usually 0.1 to 1000 parts by mass based on 1 part by mass of the compound represented by the formula (pt 1-1).

The reaction temperature at which the compound represented by the formula (pt 1-1) is reacted with the compound represented by the formula (MA 1-1), the formula (MA 1-2), the formula (MA 2-1) and the formula (MA 2-2) is usually-100℃to 300 ℃. The reaction time for reacting the compound represented by the formula (pt 1-1) with the compound represented by the formula (MA 1-1), the compound represented by the formula (MA 1-2), the compound represented by the formula (MA 2-1) and the compound represented by the formula (MA 2-2) is usually 0.5 to 500 hours.

After the completion of the reaction, the method for removing the compound (I) is not particularly limited, and it can be removed by various known methods. After removal, the obtained residue may be purified by column chromatography, recrystallization, or the like. The chemical structure of the obtained compound can be analyzed by a known analysis method and conditions thereof. Such an analysis method is not particularly limited, and examples thereof include an X-ray crystal structure analysis method, a mass analysis method (LC), an NMR analysis method, and an elemental analysis method. The X-ray crystallography can be carried out, for example, according to Chemistry of Materials,2012, volume 24, p.4647-4652.

Compounds (I), in particular containing more than 2R of formula (I) ¹ The mixture of the compounds (I) different from each other has high solubility in a solvent such as propylene glycol monomethyl ether acetate or cyclohexanone (in particular, propylene glycol monomethyl ether acetate), and has good solubility. The solubility can be determined as follows: about 50mg of a compound or a mixture of compounds for measuring solubility (hereinafter, sometimes referred to as a solute) was weighed into a 20mL screw tube, about 500mg of a solvent was added thereto, the total amount of the solute and the solvent was weighed, and after stirring for 30 minutes with a MIX ROTOR, the dissolution was visually confirmed, and the mass of the solute relative to the total mass of the solute and the solvent was obtained from the following formula (h). When dissolution was not confirmed visually, 500mg of the solvent was continuously added each time until dissolution was completed, and stirring was performed with MIX ROTOR for 30 minutes each time of addition, and the solubility was determined from the mass of the solute relative to the total mass of the solute and the solvent when dissolution was confirmed visually, according to the following formula (h).

Solubility (%) = (mass of solute)/(total mass of solute and solvent) ×100 (h)

The solubility of the compound (I) in propylene glycol monomethyl ether acetate at 20 ℃ is preferably 0.5 mass% or more, more preferably 1.0 mass% or more, still more preferably 1.5 mass% or more, and may be 15 mass% or less. When 2 or more kinds of compounds (I) are contained as the colorant, the solubility in the state of a mixture of the contained compounds (I) is preferably in the above-described range.

The content of the compound (I) in the total amount of the colorant (a) may be 100% by mass, and as a lower limit, for example, may be 0.1% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 20% by mass or more, still further preferably 30% by mass or more, and still further preferably 50% by mass or more.

The colorant (A) may further contain 1 or 2 or more perylene compounds. The perylene compound is preferably a compound in which substituents having carbonyl groups are bonded to the 3, 4, 9, and 10 positions. 3. The carbonyl group of the substituent at the 4-position is preferably bonded to form a lactone ring via an oxygen atom or an imide ring via a nitrogen atom. 9. The carbonyl group of the substituent at the 10-position is preferably bonded to form a lactone ring via an oxygen atom or an imide ring via a nitrogen atom. Further, as the perylene compound, compounds in which substituents having an oxy group are bonded independently of each other at 1, 6, 7 and 12 positions are preferable. The perylene compound is preferably a red fluorescent dye. From the viewpoint of improving the solubility in a solvent, the perylene compound represented by formula (II) (hereinafter, sometimes referred to as compound (II)) is particularly preferable.

Compound (II)

In the formula (II),

Ar ²¹ ～Ar ²⁶ independently of each other, represents an aryl group having 6 to 20 carbon atoms which may have a substituent (A3).

R ²¹ ～R ²⁴ Independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A4), a halogen atom or a nitro group.]

As Ar ²¹ ～Ar ²⁶ The aryl groups represented may be independently phenyl, naphthyl, or the like, and are preferably phenyl groups.

As Ar ²¹ ～Ar ²⁶ The substituent (A3) which the aryl group represented may have includes a halogen atom; a nitrile group; a nitro group; an amino group; an amide group; sulfonamide groups; a hydroxyl group; alkyl groups having 1 to 10 carbon atoms such as methyl, ethyl, isopropyl, and tert-butyl; cycloalkyl groups having 1 to 20 carbon atoms such as cyclopropyl and cyclobutyl; alkenyl groups having 2 to 10 carbon atoms such as vinyl group and 1-propenyl group; aryl groups having 6 to 10 carbon atoms such as phenyl group and 1-naphthyl group; aralkyl groups having 7 to 10 carbon atoms such as benzyl and phenethyl; arylalkenyl groups having 8 to 10 carbon atoms such as phenylvinyl (phenylvinyl); alkoxy groups having 1 to 10 carbon atoms such as methoxy and ethoxy; aryloxy groups having 6 to 10 carbon atoms such as a phenyloxy group, a 1-naphthyloxy group and a 2-naphthyloxy group; a thiol group; alkylthio groups having 1 to 10 carbon atoms such as methylthio and ethylthio; allylthio; arylthio groups having 6 to 10 carbon atoms such as phenylthio, 1-naphthylthio and 2-naphthylthio; sulfinyl; alkylsulfinyl groups having 1 to 10 carbon atoms such as methylsulfinyl and ethylsulfinyl; arylsulfinyl groups having 6 to 10 carbon atoms such as phenylsulfinyl, 1-naphthylsulfinyl and 2-naphthylsulfinyl; a silyl group; an oxyboronyl group; alkylamino groups having 1 to 10 carbon atoms such as a monomethylamino group, a dimethylamino group, a trimethylamino group, a monoethylamino group, a diethylamino group and a triethylamino group; arylamino groups having 6 to 10 carbon atoms such as monophenylamino; aralkylamino groups having 7 to 10 carbon atoms such as benzylamino group; alkyl amino sulfonyl groups having 1 to 10 carbon atoms such as N-methyl amino sulfonyl, N-dimethyl amino sulfonyl and N-ethyl amino sulfonyl; a carboxyl group; a carbamoyl group; alkylcarbonyl groups having 2 to 10 carbon atoms such as acetyl and propionyl; arylcarbonyl groups having 7 to 10 carbon atoms such as benzoyl; alkoxycarbonyl groups having 2 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl The method comprises the steps of carrying out a first treatment on the surface of the Aryloxycarbonyl groups having 7 to 20 carbon atoms such as phenoxycarbonyl groups; heterocyclyl groups having 1 to 20 carbon atoms such as furyl, pyrrolyl and thienyl; alkyl groups having 1 to 10 carbon atoms, in which part or all of hydrogen atoms such as chloromethyl, dichloromethyl, fluoromethyl, trifluoromethyl and pentafluoroethyl are substituted with halogen atoms; pentafluorosulfanyl; ethynyl, and the like. Among them, alkyl groups having 1 to 10 carbon atoms and halogen atoms are preferable.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of synthesis, fluorine atoms and chlorine atoms are preferable.

The alkyl group having 1 to 10 carbon atoms is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms.

Ar ²¹ ～Ar ²⁶ The aryl group represented may have 1 or 2 or more substituents (A3), or may not have them.

As Ar ²¹ ～Ar ²⁶ For example, the groups represented by the following formulas (E-1) to (E-27) can be mentioned. * Represents the bonding site.

From the viewpoint of improving solubility in a solvent, ar is used as ²¹ And Ar is a group ²² Preferred are groups represented by any of the formulas (E-5), (E-7), (E-8) or (E-11). From the viewpoint of improving solubility in a solvent, ar is used as ²³ ～Ar ²⁶ Preferred are groups represented by any of formula (E-1), formula (E-4), formula (E-9), formula (E-10), formula (E-17) or formula (E-18).

As Ar ²¹ ～Ar ²⁶ May all be the same or different.

Ar ²¹ With Ar ²² Preferably the same.

As R ²¹ ～R ²⁴ Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) include those not containing 21 or more carbon atoms, and examples thereof include those other than those described above as R ³ 、R ⁶ 、R ⁸ And R is ¹¹ The same examples of hydrocarbon groups are shown.

As R ²¹ ～R ²⁴ Examples of the substituent (A4) which the hydrocarbon group having 1 to 20 carbon atoms may have include the same ones as the substituent (A1) described above.

As R ²¹ ～R ²⁴ Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

As R ²¹ ～R ²⁴ Preferably a hydrogen atom.

Specific examples of the compound (II) include compounds shown in table 2 below.

TABLE 2

Ar ²¹

Ar ²²

Ar ²³

Ar ²⁴

Ar ²⁵

Ar ²⁶

R ²¹

R ²²

R ²³

R ²⁴

(II-1)

E-6

E-1

H

(II-2)

E-6

E-1

E-9

E-1

H

(II-3)

E-7

E-1

H

(II-4)

E-7

E-1

E-9

E-1

H

(II-5)

E-10

E-1

H

(II-6)

E-10

E-1

E-9

E-1

H

(II-7)

E-6

E-17

H

(II-8)

E-6

E-17

E-9

E-17

H

(II-9)

E-7

E-17

H

(II-10)

E-7

E-17

E-9

E-17

H

(II-11)

E-10

E-17

H

(II-12)

E-10

E-17

E-9

E-17

H

(II-13)

E-6

E-18

H

(II-14)

E-6

E-18

E-9

E-18

H

(II-15)

E-7

E-18

H

(II-16)

E-7

E-18

E-9

E-18

H

(II-17)

E-10

E-18

H

(II-18)

E-10

E-18

E-9

E-18

H

(II-19)

E-6

E-19

H

(II-20)

E-6

E-19

E-9

E-19

H

(II-21)

E-7

E-19

H

(II-22)

E-7

E-19

E-9

E-19

H

(II-23)

E-10

E-19

H

(II-24)

E-10

E-19

E-9

E-19

H

In Table 2, H represents a hydrogen atom, and E-1, E-6, E-7, E-10, E-17, E-18, and E-19 each represent a group represented by the above formula (E-1), formula (E-6), formula (E-7), formula (E-10), formula (E-17), formula (E-18), or formula (E-19).

The compound (II) is preferably compounds (II-1) to (II-24), more preferably compounds (II-1) to (II-6), compound (II-9), compound (II-10), compound (II-15), compound (II-16), compound (II-21) or compound (II-22), still more preferably compound (II-3), compound (II-4), compound (II-9), compound (II-10), compound (II-15) or compound (II-16).

The compound (II) can be produced, for example, by reacting a compound represented by the following formula (pt 3) with a compound represented by the following formula (AR 1) and a compound represented by the following formula (AR 2) in a solvent.

[ formula, R ²¹ ～R ²⁴ The same definition as above.]

Ar ^X －NH ₂ (AR1)

Ar ^X －OH (AR2)

[ formula, ar ^X With Ar as described above ²¹ ～Ar ²⁶ Is the same as defined in the following.]

Examples of the compound represented by the formula (pt 3) include 1,6,7, 12-tetrachloroperylene tetracarboxylic dianhydride and the like.

Examples of the compound represented by the formula (AR 1) include 2, 6-diisopropylaniline, aniline, 3, 5-dimethylaniline, 3, 5-di-t-butylaniline, and the like. The compound represented by the formula (AR 1) may be used alone or in an amount of 2 or more.

Examples of the compound represented by the formula (AR 2) include phenol, 4-fluorophenol, 4-chlorophenol, and 4-bromophenol. The compound represented by the formula (AR 2) may be used alone or in an amount of 2 or more.

The total amount of the compound represented by the formula (AR 1) and the compound represented by the formula (AR 2) to be used is usually 1 to 10 moles, preferably 1 to 8 moles, more preferably 1 to 6 moles, and even more preferably 1 to 4 moles, based on 1 mole of the compound represented by the formula (pt 3).

The solvent includes water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1, 2-dichlorobenzene; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, butyric acid, and the like, imidazole, and the like. Preferably N-methylpyrrolidone, imidazole or propionic acid.

The amount of the solvent to be used is usually 1 to 1000 parts by mass based on 1 part by mass of the compound represented by the formula (pt 3).

The reaction temperature is usually-100℃to 300℃or lower, preferably-90℃to 200℃and more preferably-10℃to 150 ℃. The reaction time is usually 0.5 to 500 hours.

After the completion of the reaction, the method for removing the compound (II) is not particularly limited, and it can be removed by various known methods. For example, the compound (II) may be removed by distilling off the solvent. After the solvent is distilled off, the obtained residue may be purified by column chromatography, recrystallization, or the like. After completion of the reaction, the compound (II) may be removed by filtration. After filtration, the obtained residue may be purified by column chromatography, recrystallization, or the like. The chemical structure of the compound (II) obtained can be analyzed by a known analysis method and conditions thereof. Such an analysis method is not particularly limited, and examples thereof include an X-ray crystal structure analysis method, a mass analysis method (LC), an NMR analysis method, and an elemental analysis method. The X-ray crystallography can be carried out, for example, according to Chemistry of Materials,2012, volume 24, p.4647-4652.

When the colorant (a) contains a perylene compound, the content of the perylene compound in the total amount of the colorant (a) is, for example, 0.1 mass% or more, preferably 1 mass% or more, more preferably 3 mass% or more, further preferably 5 mass% or more, further preferably 10 mass% or more, for example, 95 mass% or less, preferably 90 mass% or less, more preferably 85 mass% or less, further preferably 80 mass% or less, and further preferably 75 mass% or less.

When the colorant (a) contains a perylene compound, the content of the perylene compound is, for example, 3 mass% or more, preferably 5 mass% or more, more preferably 10 mass% or more, for example, 95 mass% or less, preferably 90 mass% or less, more preferably 85 mass% or less, based on the total amount of the compound (I) and the perylene compound.

When the colorant (A) contains a compound (I) and a perylene compound, the compound (I) may be used as a sensitizer for the perylene compound.

Colorant (A1)

The colorant (A) of the present invention may contain a dye (hereinafter, sometimes referred to as a dye (A1-1)) and/or a pigment (hereinafter, sometimes referred to as a pigment (A1-2)) other than the compound (I) and the perylene compound (hereinafter, sometimes referred to as a dye (A1-1) and the pigment (A1-2) together, sometimes referred to as a colorant (A1)). These may be used alone or in combination of 2 or more.

The dye (A1-1) is not particularly limited as long as it does not contain the compound (I) and the perylene compound, and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, mordant dyes, and the like. Examples of dyes include compounds classified into dyes by color index (The Society of Dyers and Colourists publication) and known dyes described in dyeing guidelines (color dyeing company). Further, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, and the like can be exemplified. Among them, organic solvent-soluble dyes are preferable.

The pigment (A1-2) is not particularly limited as long as it does not contain a perylene compound, and known pigments can be used, and examples thereof include pigments classified as pigments (pigment) in the color index (The Society of Dyers and Colourists publication).

Examples of pigments classified as pigments (pigments) include yellow pigments such as 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, 185, 194, 214, 231;

Orange pigments such as c.i. pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;

c.i. pigment red 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273;

c.i. pigment blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc. blue pigments;

c.i. violet pigments such as violet 1, 19, 23, 32, 36, 38;

green pigments such as c.i. pigment green 7, 36, 58, 59, 62, 63;

brown pigments such as pigment brown 23, 25;

black pigments such as c.i. pigment black 1 and 7.

When the colorant (a) further contains the colorant (A1), the lower limit of the total content of the compound (I) and the perylene compound in the colorant (a) is, for example, 1 mass% or more, preferably 2 mass% or more, more preferably 10 mass% or more, still more preferably 25 mass% or more, and particularly preferably 50 mass% or more, relative to the total amount of the colorant (a). On the other hand, when the colorant (a) further contains the colorant (A1), the upper limit of the total content of the compound (I) and the perylene compound in the colorant (a) is smaller than 100% by mass, for example, relative to the total amount of the colorant (a).

The colorant (a) may be subjected to a rosin treatment, a surface treatment using a derivative having an acidic group or a basic group introduced therein, a grafting treatment to the surface of the colorant (a) based on a polymer compound or the like, a micronization treatment based on a sulfuric acid micronization method or the like, a washing treatment based on an organic solvent, water or the like for removing impurities, a removal treatment based on an ion exchange method or the like for ionic impurities, or the like, as required. The particle size of the colorant (a) is preferably substantially uniform.

< coloring resin composition >

The colored resin composition of the present invention contains a colorant (a) and a resin (hereinafter, sometimes referred to as a resin (B)).

The colored resin composition of the present invention may further contain a polymerizable compound (hereinafter, sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (D)).

The colored resin composition of the present invention may further contain a solvent (hereinafter, may be referred to as a solvent (E)).

The colored resin composition of the present invention may further contain a polymerization initiator aid (hereinafter, may be referred to as a polymerization initiator aid (D1)).

The colored resin composition of the present invention may further contain a leveling agent (hereinafter, may be referred to as leveling agent (F)).

In the present specification, the compounds exemplified as the respective components may be used singly or in combination unless otherwise specified.

When the colored resin composition contains the solvent (E), the colored resin composition may be prepared by preparing a colored composition (also sometimes referred to as a colorant-containing liquid) containing the colorant (a) and the solvent (E) in advance and then using the colored composition. When the colorant (a) is insoluble in the solvent (E), for example, when the colorant (a) contains the pigment (A1-2), the coloring composition can be prepared by dispersing and mixing the colorant (a) in the solvent (E). The coloring composition may contain a part or all of the solvent (E) contained in the coloring resin composition.

The content of the colorant (a) in the coloring composition is preferably 0.001 to 99% by mass, more preferably 0.01 to 95% by mass, still more preferably 0.1 to 90% by mass, and still more preferably 0.1 to 50% by mass, based on the total amount of the coloring composition.

The colorant (a) can be dispersed in a solution by dispersing the colorant (a) with a dispersant. When the colorant (a) is used in combination of 2 or more kinds, the dispersion treatment may be performed alone or in combination of two or more kinds.

Examples of the dispersant include surfactants, and any of cationic, anionic, nonionic, and amphoteric surfactants may be used. Specifically, examples thereof include surfactants such as polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of 2 or more. Examples of the dispersant include KP (manufactured by Xinyue chemical industry Co., ltd.), FLOWLEN (manufactured by Kyowa chemical Co., ltd.), solsperse (registered trademark) (manufactured by Zeneca Co., ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Weisu Fine chemical Co., ltd.), disperbyk (registered trademark) (manufactured by BYK-Chemie Co., ltd.), BYK (registered trademark) (manufactured by BYK-Chemie Co., ltd.), and the like when expressed by trade names. As the dispersant, a resin (B) described later can be used.

When a dispersant is used, the amount of the dispersant (solid content) to be used is usually 1 to 10000 parts by mass, preferably 5 to 5000 parts by mass, more preferably 10 to 3000 parts by mass, and even more preferably 20 to 1000 parts by mass, based on 100 parts by mass of the colorant (a). When the amount of the dispersant is within the above range, a coloring composition in a more uniform dispersion state tends to be obtained.

The content of the colorant (a) is preferably 0.1 to 50% by mass, more preferably 0.5 to 40% by mass, and even more preferably 1 to 30% by mass, based on the total amount of the solid components of the colored resin composition. When the content of the colorant (a) is within the above range, the color density is sufficient when a color filter is produced, and the resin (B) can be contained in a desired amount in the composition, so that a pattern having sufficient mechanical strength can be formed, which is preferable.

Here, the "total amount of solid components" in the present specification means an amount obtained by subtracting the content of the solvent from the total amount of the colored resin composition. The total amount of the solid components and the content of each component relative to the total amount can be measured by a known analytical method such as liquid chromatography or gas chromatography.

< resin (B) >)

The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably a polymer having a structural unit derived from at least 1 monomer (hereinafter, sometimes referred to as "monomer (a)") selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride.

The resin (B) is preferably a copolymer having a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (B)") and/or other structural units.

Examples of the other structural unit include a structural unit derived from a monomer copolymerizable with the monomer (a) (wherein the monomer is different from the monomer (a) and the monomer (b): hereinafter, sometimes referred to as "monomer (c)"), a structural unit having an ethylenically unsaturated bond, and the like.

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

unsaturated dicarboxylic acids such as 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, dimethyltetrahydrophthalic acid and 1, 4-cyclohexanedicarboxylic acid;

carboxyl group-containing bicyclic unsaturated compounds such as methyl-5-norbornene-2, 3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5, 6-dicarboxyibicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo [2.2.1] hept-2-ene and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;

carboxylic anhydrides such as anhydrides of the above-mentioned unsaturated dicarboxylic acids excluding fumaric acid and mesaconic acid;

Unsaturated mono- [ (meth) acryloyloxyalkyl ] esters of polycarboxylic acids having 2 or more members such as succinic acid mono- [ 2- (meth) acryloyloxyethyl ] ester and phthalic acid mono- [ 2- (meth) acryloyloxyethyl ] ester;

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

Among them, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an aqueous alkali solution.

In the present specification, "(meth) acrylic acid" means at least 1 kind selected from acrylic acid and methacrylic acid. The same meaning applies to the "(meth) acryl" and "(meth) acrylate" and the like.

When the resin (B) is a copolymer having a structural unit derived from the monomer (a), the ratio of the structural unit derived from the monomer (a) in the copolymer is preferably 2 to 60 mol% in all the constituent units of the copolymer.

The monomer (b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least 1 selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring (an oxolane ring)) and an ethylenically unsaturated bond.

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

Examples of the monomer (b) include a monomer having an oxirane group and an ethylenic unsaturated bond (hereinafter, sometimes referred to as "monomer (b 1)"), a monomer having an oxetane group and an ethylenic unsaturated bond (hereinafter, sometimes referred to as "monomer (b 2)"), a monomer having a tetrahydrofuranyl group and an ethylenic unsaturated bond (hereinafter, sometimes referred to as "monomer (b 3)"), and the like.

Examples of the monomer (b 1) include a monomer having a structure in which a linear or branched unsaturated aliphatic hydrocarbon is epoxidized (hereinafter, referred to as "monomer (b 1-1)") and a monomer having a structure in which an unsaturated alicyclic hydrocarbon is epoxidized (hereinafter, referred to as "monomer (b 1-2)").

As the monomer (b 1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable.

Examples of the monomer (b 1-1) include glycidyl (meth) acrylate, β -methyl glycidyl (meth) acrylate, β -ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α -methyl-o-vinylbenzyl glycidyl ether, α -methyl-m-vinylbenzyl glycidyl ether, α -methyl-p-vinylbenzyl glycidyl ether, 2, 3-bis (glycidoxymethyl) styrene, 2, 4-bis (glycidoxymethyl) styrene, 2, 5-bis (glycidoxymethyl) styrene, 2, 6-bis (glycidoxymethyl) styrene, 2,3, 4-tris (glycidoxymethyl) styrene, 2,3, 5-tris (glycidoxymethyl) styrene, 2,3, 6-tris (glycidoxymethyl) styrene, 3,4, 5-tris (glycidoxymethyl) styrene, and 2, 6-tris (glycidoxymethyl) styrene.

Examples of the monomer (b 1-2) include vinylcyclohexene monooxide, 1, 2-epoxy-4-vinylcyclohexane (for example, celloxide (registered trademark) 2000, (product of Daicel), 3, 4-epoxycyclohexylmethyl (meth) acrylate (for example, cyclomer (registered trademark) A400, (product of Daicel), 3, 4-epoxycyclohexylmethyl (meth) acrylate (for example, cyclomer (registered trademark) M100, (product of Daicel)), a compound represented by the formula (BI), and a compound represented by the formula (BII).

[ formula (BI) and formula (BII), R ^a And R is ^b Independently of each other, represents 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 hydroxyl group.

X ^a And X ^b Independently of each other, represents 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 site to O. ]

Examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl and the like.

Examples of the alkyl group having a hydrogen atom substituted with a hydroxyl group include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, and 4-hydroxybutyl group.

As R ^a And R is ^b The hydrogen atom, methyl group, hydroxymethyl group, 1-hydroxyethyl group and 2-hydroxyethyl group are preferable, and the hydrogen atom and methyl group are more preferable.

Examples of the alkanediyl group include methylene, ethylene, propane-1, 2-diyl, propane-1, 3-diyl, butane-1, 4-diyl, pentane-1, 5-diyl and hexane-1, 6-diyl.

As X ^a And X ^b A single bond, methylene, ethylene, or-CH may be preferably mentioned ₂ －O－、*－CH ₂ CH ₂ O-, more preferably a single bond, -CH ₂ CH ₂ -O- (x) represents a bonding site to O).

The compound represented by the formula (BI) may be a compound represented by any one of the formulas (BI-1) to (BI-15), or the like. Among them, preferred are compounds represented by the formulas (BI-1), (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) and formulas (BI-11) to (BI-15), and more preferred are compounds represented by the formulas (BI-1), formula (BI-7), formula (BI-9) and formula (BI-15).

The compound represented by the formula (BII) may be a compound represented by any one of the formulas (BII-1) to (BII-15), and among them, the compounds represented by the formulas (BII-1), (BII-3), the formulas (BII-5), the formulas (BII-7), the formulas (BII-9) and the formulas (BII-11) to (BII-15) may be preferable, and the compounds represented by the formulas (BII-1), the formulas (BII-7), the formulas (BII-9) and the formulas (BII-15) may be more preferable.

The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used singly or in combination of 2 or more. The compound represented by the formula (BI) and the compound represented by the formula (BII) may also be used in combination. When the compound represented by the formula (BI) and the compound represented by the formula (BII) are used in combination, the content ratio of the compound represented by the formula (BI) to the compound represented by the formula (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, still more preferably 20:80 to 80:20 on a molar basis.

As the monomer (b 2) having an oxetanyl group and an ethylenic unsaturated bond, a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable.

Examples of the monomer (b 2) include 3-methyl-3- (meth) acryloyloxymethyl oxetane, 3-ethyl-3- (meth) acryloyloxymethyl oxetane, 3-methyl-3- (meth) acryloyloxyethyl oxetane, and 3-ethyl-3- (meth) acryloyloxyethyl oxetane.

As the monomer (b 3) having a tetrahydrofuranyl group and an ethylenic unsaturated bond, a monomer having a tetrahydrofuranyl group and a (meth) acryloyloxy group is more preferable.

Examples of the monomer (b 3) include tetrahydrofurfuryl acrylate (for example, viscoat V#150, manufactured by Osaka organic chemical industry Co., ltd.), and tetrahydrofurfuryl methacrylate.

When the resin (B) is a copolymer having a structural unit derived from the monomer (B), the ratio of the structural unit derived from the monomer (B) in the copolymer is preferably 2 to 98 mol% based on all the constituent units of the copolymer.

Examples of the monomer (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, and cyclopentyl (meth) acrylate) Cyclohexyl acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo (meth) acrylate [5.2.1.0 ² ^,6 ]Decane-8-yl ester (which is known as dicyclopentyl (meth) acrylate ". Additionally, it is sometimes referred to as tricyclodecyl (meth) acrylate"), [5.2.1.0 ] tricyclo (meth) acrylate, as a conventional name in this technical field) ^2,6 ]Decane-9-yl ester, tricyclo [5.2.1.0 (meth) acrylic acid ^2,6 ]Decen-8-yl ester (known as dicyclopentenyl (meth) acrylate "as a conventional name in this technical field), tricyclo (meth) acrylate [5.2.1.0 ] ^2,6 ](meth) acrylic esters such as decen-9-yl ester, dicyclopentyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, and benzyl (meth) acrylate;

hydroxy group-containing (meth) acrylates such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;

(meth) acrylic esters containing a halogen atom such as 2,3, 4, 5-octafluoropentyl (meth) acrylate;

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

bicyclo [2.2.1] hept-2-ene, 5-methyl-bicyclo [2.2.1] hept-2-ene, 5-ethyl-bicyclo [2.2.1] hept-2-ene, 5-hydroxy-bicyclo [2.2.1] hept-2-ene, 5- (2 '-hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5-methoxy-bicyclo [2.2.1] hept-2-ene, 5-ethoxy-bicyclo [2.2.1] hept-2-ene, 5, 6-dihydroxy-bicyclo [2.2.1] hept-2-ene, 5, 6-di (hydroxymethyl) bicyclo [2.2.1] hept-2-ene, 5, 6-di (2' -hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5, 6-dimethoxy-bicyclo [ 2.1] hept-2-ene, 5, 6-diethoxy-bicyclo [ 2.1] hept-2-ene, 5-diethoxy-2.1 ] bicyclo [ 2.1] hept-2-ene, 5-ethoxy-2.1 ] bicyclohexa-2-ene, 5-hydroxy-2-carbonyl-2.1-ene, 5-dihydroxy-bicyclo [2.2.1] hept-ene, 5-hydroxy-2.1 ] bicyclooxy-carbonyl-2-ene, 5-hydroxy-bicyclo [ 2.1.1 ] bicyclooxy-2.1 ] hept-ene;

Dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3-maleimide propionate and N- (9-acridinyl) maleimide;

vinyl-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole, and p-methoxystyrene; vinyl-containing nitriles such as (meth) acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl-containing amides such as (meth) acrylamide; esters such as vinyl acetate; dienes such as 1, 3-butadiene, isoprene and 2, 3-dimethyl-1, 3-butadiene.

Among them, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyl toluene, tricyclo (meth) acrylate [5.2.1.0 ] are preferable ^2,6 ]Decane-8-yl ester, tricyclo [5.2.1.0 (meth) acrylic acid ^2,6 ]Decane-9-yl ester, tricyclo [5.2.1.0 (meth) acrylic acid ^2,6 ]Decen-8-yl ester, tricyclo (meth) acrylate [5.2.1.0 ^2,6 ]Decen-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1]Hept-2-ene and benzyl (meth) acrylate, and the like.

When the resin (B) is a copolymer having a structural unit derived from the monomer (c), the ratio of the structural unit derived from the monomer (c) in the copolymer is preferably 1 to 98 mol% in all the constituent units of the copolymer.

Specific examples of the resin (B) include 3, 4-epoxycyclohexane (meth) acrylateMethyl ester/(meth) acrylic acid copolymer, 3, 4-epoxytricyclo [5.2.1.0 (meth) acrylic acid ^2,6 ]Decyl ester/(meth) acrylic acid copolymer, glycidyl (meth) acrylate/(meth) acrylic acid benzyl ester/(meth) acrylic acid copolymer, glycidyl (meth) acrylate/styrene/(meth) acrylic acid copolymer, 3, 4-epoxytricyclo (meth) acrylic acid [5.2.1.0 ^2,6 ]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide copolymer, 3, 4-epoxytricyclo (meth) acrylic acid [5.2.1.0 ² ^,6 ]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide/(meth) acrylic acid 2-hydroxyethyl ester copolymer, 3, 4-epoxytricyclo (meth) acrylic acid 5.2.1.0 ^2,6 ]Decyl ester/(meth) acrylic acid/vinyltoluene copolymer, 3, 4-epoxytricyclo (meth) acrylic acid [5.2.1.0 ^2,6 ]Decyl ester/(meth) acrylic acid benzyl ester/(meth) acrylic acid copolymer, 3, 4-epoxytricyclo [5.2.1.0 (meth) acrylic acid ^2,6 ]Decyl ester/(meth) acrylic acid 2-ethylhexyl (meth) acrylate copolymer, 3, 4-epoxytricyclo (meth) acrylate [5.2.1.0 ^2,6 ]Decyl ester/tricyclo (meth) acrylate [5.2.1.0 ^2,6 ]Decenyl ester/(meth) acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3- (meth) acryloyloxymethyl oxetane/(meth) acrylic acid/styrene copolymer, benzyl (meth) acrylate/(meth) acrylic acid copolymer, styrene/(meth) acrylic acid copolymer, resins described in each of Japanese patent application laid-open No. 9-106071, japanese patent application laid-open No. 2004-29518 and Japanese patent application laid-open No. 2004-361455, and the like.

Among them, the resin (B) is preferably a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (B).

In the copolymer containing the structural unit derived from the monomer (a) and the structural unit derived from the monomer (b), the ratio of the structural units derived from the respective monomers is preferably in the following range among all the structural units constituting the copolymer.

Structural units derived from monomer (a): 2 to 60 mol% (more preferably 10 to 50 mol%)

Structural units derived from monomer (b): 40 to 98 mol% (more preferably 50 to 90 mol%)

When the ratio of the structural units derived from the monomers (a) and (b) is in the above range, there is a tendency that the storage stability of the colored resin composition, the developability upon forming a colored pattern, and the solvent resistance of the obtained color filter are excellent.

The resin (B) may be combined with 2 or more kinds, in which case the resin (B) is at least

Preferably at least 1 copolymer comprising structural units derived from monomer (a) and structural units derived from monomer (b),

more preferably at least 1 copolymer comprising structural units derived from monomer (a) and structural units derived from monomer (b 1),

further preferably at least 1 copolymer comprising structural units derived from the monomer (a) and structural units derived from the monomer (b 1-2),

even more preferably 3, 4-epoxytricyclo [5.2.1.0 ] selected from (meth) acrylic acid ^2,6 ]Decyl ester/(meth) acrylic acid copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] of (meth) acrylic acid ^2,6 ]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide/(meth) acrylic acid 2-hydroxyethyl ester copolymer, 3, 4-epoxytricyclo (meth) acrylic acid 5.2.1.0 ^2,6 ]Decyl ester/(meth) acrylic acid/vinyltoluene copolymer, 3, 4-epoxytricyclo (meth) acrylic acid [5.2.1.0 ^2,6 ]More than 1 kind of decyl ester/(methyl) acrylic acid 2-ethylhexyl ester copolymer.

The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably 1000 to 100000, more preferably 2000 to 50000, and even more preferably 3000 to 30000. When the weight average molecular weight is within the above range, the solubility of the unexposed portion in the developer tends to be high, and the residual film rate and hardness of the obtained pattern tend to be also high.

The dispersity [ weight average molecular weight (Mw)/number average molecular weight (Mn) ] of the resin (B) is preferably 1 to 6, more preferably 1 to 5, still more preferably 1 to 4.

The acid value (solid content conversion value) of the resin (B) is preferably 10mg-KOH/g to 300mg-KOH/g, more preferably 20mg-KOH/g to 250mg-KOH/g, still more preferably 25mg-KOH/g to 200mg-KOH/g, still more preferably 30mg-KOH/g to 150mg-KOH/g, particularly preferably 40mg-KOH/g to 135mg-KOH/g. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1g of the resin, and can be obtained by, for example, titration using an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 5 to 80% by mass, more preferably 10 to 60% by mass, still more preferably 15 to 50% by mass, and still more preferably 15 to 45% by mass, based on 100% by mass of the solid content of the colored resin composition. When the content of the resin (B) is within the above range, the solubility of the unexposed portion in the developer tends to be high.

< polymerizable Compound (C) >)

The polymerizable compound (C) is a compound polymerizable by a living radical and/or an acid generated by the polymerization initiator (D), and examples thereof include a compound having a polymerizable ethylenically unsaturated bond, and the like, and is preferably a (meth) acrylate compound.

Examples of the polymerizable compound having 1 ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the like, and the above-mentioned monomer (a), monomer (b), and monomer (c).

Examples of the polymerizable compound having 2 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 3 or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra (meth) acrylate, ethylene glycol-modified dipentaerythritol hexa (meth) acrylate, 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.

The weight average molecular weight of the polymerizable compound (C) is preferably 50 to 4000, more preferably 70 to 3500, still more preferably 100 to 3000, still more preferably 150 to 2900, particularly preferably 250 to 1500.

When the polymerizable compound (C) is contained, the content of the polymerizable compound (C) may be, for example, 1 to 99% by mass, preferably 5 to 90% by mass, more preferably 10 to 80% by mass, and even more preferably 20 to 70% by mass, based on the total amount of the solid components of the colored resin composition.

Polymerization initiator (D) >)

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

Examples of the polymerization initiator (D) include oxime compounds (e.g., O-acyl oxime compounds), alkylbenzene ketone compounds, biimidazole compounds, triazine compounds, and acyl phosphine oxide compounds.

As the O-acyl oxime compound, for example, examples thereof include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl ] ethane-1-imine, N-acetoxy-1- [ 9-ethyl-6- { 2-methyl-4- (3, 3-dimethyl-2, 4-dioxacyclopentylmethoxy) benzoyl } -9H-carbazole-3-yl ] ethane-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-1-one-imine, N-acetoxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl ] ethane-1-imine, N-acetoxy-1- [ 9-ethyl-6- { 2-methyl-4- (3, 3-dioxacyclopentylmethoxy) benzoyl-1-imine, and the like. As the O-acyl oxime compound, commercially available products such as Irgacure OXE01, OXE02 (both of them are manufactured by BASF) and N-1919 (manufactured by ADEKA) can be used. Among them, as the O-acyloxime compound, at least 1 selected from the group consisting of N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine is more preferable.

Examples of the alkylbenzene ketone compound include 2-methyl-2-morpholino-1- (4-methylsulfanyl phenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, and 2- (dimethylamino) -2- [ (4-methylphenyl) methyl ] -1- [4- (4-morpholinyl) phenyl ] butan-1-one. As the alkylbenzene ketone compound, commercially available products such as Irgacure 369, 907 and 379 (all of which are manufactured by BASF) can be used.

Examples of the alkylbenzene ketone compound include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] propan-1-one, 1-hydroxycyclohexylphenyl ketone, an oligomer of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, α -diethoxyacetophenone and benzildimethyl ketal.

Examples of the bisimidazole compound include 2,2' -bis (2-chlorophenyl) -4,4', 5' -tetraphenylbisimidazole and 2,2' -bis (2, 3-dichlorophenyl) -4,4', 5' -tetraphenylbisimidazole (for example, reference is made to Japanese patent application laid-open No. 6-75372, japanese patent application laid-open No. 6-75373, etc.), 2' -bis (2-chlorophenyl) -4,4', 5' -tetra (alkoxyphenyl) bisimidazole, 2' -bis (2-chlorophenyl) -4,4', and 5,5' -tetrakis (dialkoxyphenyl) biimidazole, 2' -bis (2-chlorophenyl) -4,4', 5' -tetrakis (trialkoxyphenyl) biimidazole (for example, refer to Japanese patent publication No. 48-38403, japanese patent application laid-open No. 62-174204, etc.), biimidazole compounds in which phenyl groups at the 4,4', 5' -positions are substituted with carboalkoxy groups (for example, refer to Japanese patent application laid-open No. 7-10913, etc.), and the like.

Examples of the triazine compound include 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6-piperonyl-1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (5-methylfuran-2-yl) vinyl ] -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (furan-2-yl) vinyl ] -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (4-diethylamino-2-methylphenyl) vinyl ] -1,3, 5-triazine, and 2, 4-bis (trichloromethyl) -6- [ 2- (3, 4-dimethoxyphenyl) vinyl ] -1,3, 5-triazine.

Examples of the acylphosphine oxide compound include 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide and the like. Commercial products such as Irgacure 819 (registered trademark) manufactured by BASF corporation can be used.

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 compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4 ' -methyldiphenyl sulfide, 3', 4' -tetrakis (t-butylperoxycarbonyl) benzophenone, and 2,4, 6-trimethylbenzophenone; quinone compounds such as 9, 10-phenanthrenequinone, 2-ethylanthraquinone, camphorquinone, etc.; 10-butyl-2-chloroacridone, benzil, methyl benzoylformate, a titanocene compound, and the like.

These are preferably used in combination with a polymerization initiator (D1) described later, particularly an amine.

The polymerization initiator (D) is preferably a polymerization initiator containing at least 1 selected from the group consisting of an alkylbenzene compound, a triazine compound, an acylphosphine oxide compound, an oxime compound and a biimidazole compound, more preferably a polymerization initiator containing an oxime compound, and still more preferably a polymerization initiator containing an O-acyloxime compound.

When the polymerization initiator (D) is contained, the content of the polymerization initiator (D) is preferably 0.01 to 30 parts by mass, more preferably 0.1 to 20 parts by mass, relative to 100 parts by mass of the total amount of all the resins (B) and the polymerizable compounds (C) contained in the colored resin composition. When the content of the polymerization initiator (D) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, so that the productivity of the color filter is improved.

Polymerization initiation aid (D1) >, polymerization initiation aid

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

Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, carboxylic acid compounds, and the like.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N-dimethyl-p-toluidine, 4' -bis (dimethylamino) benzophenone (known as Michaelis ' ketone), 4' -bis (diethylamino) benzophenone, and 4,4' -bis (ethylmethylamino) benzophenone, and 4,4' -bis (diethylamino) benzophenone may be preferably used. As the amine compound, commercially available products such as EAB-F (manufactured by Baogu chemical Co., ltd.) can be used.

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

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

Examples of the carboxylic acid compound include phenylthioalkyl acetic acid, methylphenylsulfanyl acetic acid, ethylphenylthioalkyl acetic acid, methylethylphenylsulfanyl acetic acid, dimethylphenylsulfanyl acetic acid, methoxyphenylthioalkyl acetic acid, dimethoxyphenylthioalkyl acetic acid, chlorophenyl thioalkyl acetic acid, dichlorophenylthioalkyl acetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthyloxyacetic acid.

When these polymerization initiator additives (D1) are used, the content thereof is preferably 0.01 to 30 parts by mass, more preferably 0.1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition.

Solvent (E) >, solvent (E)

The solvent (E) is not particularly limited, and solvents generally used in this field can be used.

For the solvent (E), for example, an ester solvent (a solvent containing-CO-O-and not containing-O-in the molecule), an ester solvent ether solvents (solvents containing-O-and not-CO-O-in the molecule), ether ester solvents (solvents containing-CO-O-and-O-in the molecule), and the like an ether solvent (a solvent containing-O-and not-CO-O-in the molecule) ether ester solvents (solvents containing-CO-O-and-O-in the molecule).

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and gamma-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 glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, and 1, 4-di-nAlkyl, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methylanisole 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 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 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 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-methyl-2-pentanone, cyclopentanone, cyclohexanone, isophorone, and the like.

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

Examples of the hydrocarbon solvent include benzene, toluene, xylene, cyclohexane, methylcyclohexane, ethylcyclohexane, n-hexane, styrene, and mesitylene.

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

These solvents may be used in combination of 2 or more.

The solvent is preferably propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol, or cyclohexanone, more preferably propylene glycol monomethyl ether acetate or cyclohexanone, and still more preferably propylene glycol monomethyl ether acetate.

When the solvent (E) is contained, the content of the solvent (E) is usually less than 100% by mass, preferably 99.99% by mass or less, more preferably 1% by mass to 99.9% by mass, still more preferably 10% by mass to 99% by mass, still more preferably 20% by mass to 97% by mass, particularly preferably 30% by mass to 95% by mass, still more preferably 40% by mass to 95% by mass, and particularly preferably 50% by mass to 95% by mass, relative to the total amount of the colored resin composition. When the content of the solvent (E) is within the above range, flatness at the time of coating becomes good, and further, since the color density is not insufficient at the time of forming a color filter, display characteristics tend to become good.

< leveling agent (F) >)

Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms. They may have a polymerizable group in a side chain.

Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, toray Silicone DC PA, toray Silicone SH PA, toray Silicone DC11PA, toray Silicone SH PA, toray Silicone SH PA, toray Silicone SH29PA, toray Silicone SH PA, toray Silicone SH8400 (trade name: dow Corning Toray, manufactured by Mitsui chemical Co., ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Xinyue chemical Co., ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, TSF4460 (manufactured by Momentive Performance Materials Japan contract Co., ltd.) and the like are exemplified.

The fluorine-based surfactant may be a surfactant having a fluorocarbon chain in the molecule. Specifically, examples thereof include FLUORAD FC430, FLUORAD FC431 (manufactured by Sumitomo 3M (Inc.), MEGAFAC F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC (Inc.), F-top EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi (Inc.), surflon S381, surflon S382, surflon SC101, surflon SC105 (manufactured by Asahi Nitro) and E5844 (manufactured by Mitsubishi gold fine chemical corporation).

Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, there are exemplified MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, MEGAFAC F443 (DIC corporation), and the like.

When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005 mass% to 3 mass%, more preferably 0.001 mass% to 1 mass%, and even more preferably 0.005 mass% to 0.5 mass% of the total amount of the colored resin composition. The content of pigment dispersant is not included in the content. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

< other Components >)

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

Process for producing colored resin composition

The colored resin composition can be prepared by mixing the colorant (a) and the resin (B), and if necessary, the polymerizable compound (C), the polymerization initiator (D), the polymerization initiator auxiliary (D1), the solvent (E), the leveling agent (F) and/or other components. The mixing may be carried out by using known or conventional devices and conditions.

The colorant (A) may be used by mixing it with a part or the whole of the solvent (E) in advance and dispersing it in a state of having an average particle diameter of about 0.2 μm or less by a bead mill or the like. In this case, the dispersant and part or all of the resin (B) may be blended as necessary.

The colorant (a) may be used in a state of being dissolved in part or all of the solvent (E) in advance.

The remaining components are mixed into the coloring composition (colorant-containing liquid) obtained as described above so as to reach a prescribed concentration, whereby a target colored resin composition can be prepared.

Method for producing color filter

The color filter which may be the color conversion layer may be formed of a colored resin composition.

The colored resin composition is applied to a substrate, and the volatile components such as a solvent are removed and dried, thereby forming a colored coating film. The colored coating film thus formed is included in the color filter of the present invention.

Examples of the method for forming the colored pattern include photolithography, inkjet method, and printing method. Among them, photolithography is preferable. Photolithography is a method of forming a colored composition layer by applying the colored resin composition to a substrate and drying the same, exposing the colored composition layer to light through a photomask, and developing the same. In the photolithography, a colored coating film which is a cured product of the colored composition layer can be formed without using a photomask and/or without developing during exposure. The colored pattern and the colored coating film thus formed are the color filter of the present invention.

The film thickness of the color filter to be produced is not particularly limited and may be appropriately adjusted depending on the purpose, application, and the like, and is, for example, preferably 30 μm or less, more preferably 20 μm or less, still more preferably 6 μm or less, still more preferably 3 μm or less, and the lower limit is not particularly limited, and is usually 0.1 μm or more.

As the substrate, a glass plate such as quartz glass, borosilicate glass, aluminosilicate glass, or soda lime glass coated with silica on the surface, a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, or the like, silicon, a substrate having aluminum, silver/copper/palladium alloy thin films formed on the substrate, or the like can be used. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates.

The formation of each color pixel by photolithography can be performed by using a known or conventional apparatus and conditions. For example, the production can be performed as follows.

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

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

The temperature at the time of heat drying is preferably 30 to 120 ℃, more preferably 50 to 110 ℃. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

In the case of drying under reduced pressure, it is preferable to carry out the drying under a pressure of 50 to 150Pa at a temperature of 20 to 25 ℃.

The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected according to the film thickness of the target color filter.

Next, the coloring composition layer is exposed to light through a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the intended use is used. The light source used for exposure is preferably a light source that generates light having a wavelength of 250 to 450 nm. For example, light of less than 350nm may be cut off using a filter that cuts off this wavelength region, or light of around 436nm, around 408nm, or around 365nm may be selectively extracted using a band-pass filter that extracts these wavelength regions. Specifically, mercury lamps, light emitting diodes, metal halide lamps, and halogen lamps are cited. In order to uniformly irradiate the entire exposure surface with parallel light and accurately align the photomask and the substrate on which the coloring composition layer is formed, it is preferable to use an exposure device (mask aligner) such as a stepper (reduction projection exposure machine) or a proximity exposure machine.

The exposed coloring composition layer is developed by contacting with a developer, thereby forming a coloring pattern on the substrate. The unexposed portions of the colored composition layer are removed by development by dissolution in a developer. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is preferable. The concentration of these alkali compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The developer may contain a surfactant.

The developing method may be any of spin-coating immersing method, spraying method, and the like. Further, the substrate can be inclined at an arbitrary angle during development.

The substrate after development is preferably washed with water.

The resulting colored pattern is preferably further post-baked. The post-baking temperature is preferably 100℃or higher, more preferably 150℃or higher, further preferably 160℃or higher, preferably 250℃or lower, further preferably 240℃or lower. The post-baking time is preferably 1 minute or more, more preferably 2 minutes or more, further preferably 10 minutes or more, preferably 120 minutes or less, further preferably 60 minutes or less.

The color filter thus obtained as a colored pattern or a colored coating film may be further subjected to a surface coating treatment in order to impart various properties.

< display device >)

The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL display device, electronic paper, or the like) or a solid-state imaging element, and is useful as a color filter used in an organic EL display device using an OLED (organic light emitting diode ) or the like. Since the organic EL display device does not require a backlight, it is light-weighted and thin compared with a liquid crystal display device or the like, and it is possible to achieve high image quality such as high response speed and high contrast, and it is also possible to bend the device, and therefore it is used in various fields such as mobile phones, portable information terminals, televisions, and the like.

According to the colored resin composition containing the colorant (a) of the present invention, a color filter excellent in light resistance can be formed. In the present invention, the term "good light resistance" means that the change in color before and after the light irradiation test is small, or the change in fluorescence intensity before and after the light irradiation test is small (that is, the maintenance rate of fluorescence intensity is high). Further, according to the colored resin composition containing the colorant (a) of the present invention, a color filter having high fluorescence intensity and excellent brightness can be formed as compared with a colored resin composition containing a conventional perylene compound as a colorant. Further, according to the colored resin composition containing the colorant (a) of the present invention, a color filter excellent in heat resistance can be formed. In the present invention, good heat resistance means that the change in color before and after the heating test is small or the change in fluorescence intensity before and after the heating test is small (that is, the maintenance rate of fluorescence intensity is high). The fluorescence intensity can be measured, for example, using a fluorescence spectrophotometer (FluoMAX-3; manufactured by horiba corporation).

Examples

The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to the following examples, and it is needless to say that appropriate modifications may be added within the scope of the present invention as appropriate to the gist described above and the gist described below, and these modifications are included in the technical scope of the present invention. Hereinafter, "parts" means "parts by mass" and "%" means "% by mass" unless otherwise specified.

In the examples below, the structure of the compounds was confirmed by MASS analysis (LC; model 1200 by Agilent; model LC/MSD6130 by Agilent).

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

The device comprises: HLC-8120GPC (manufactured by Tosoh Co., ltd.)

Column: TSK-GELG2000HXL

Column temperature: 40 DEG C

y: tetrahydrofuran (THF)

Flow rate: 1.0 mL/min

Concentration of solid content of the analysis sample: 0.001 to 0.01 mass%

Injection amount: 50 mu L

A detector: RI (RI)

Calibration standard substance: TSK STANDARD PolySTYRENE F-40, F-4,F-288, A-2500, A-500 (manufactured by Tosoh Corp.)

The dispersion was defined as the ratio (Mw/Mn) of the weight average molecular weight to the number average molecular weight in terms of polystyrene obtained above.

Synthesis example 1

< preparation of Compound (IV) >)

Adding N ¹ ,N ² 20 parts of bis (2, 6-diisopropylphenyl) perylene-3, 4,9, 10-tetracarboxylic acid diimide (manufactured by Tokyo chemical industries, ltd.), 788 parts of maleic anhydride (manufactured by Tokyo chemical industries, ltd.) and 12 parts of tetrachloro-p-benzoquinone (manufactured by Tokyo chemical industries, ltd.) were stirred at 170℃for 25 hours. While maintaining the obtained mixture at 70℃or lower, 800 parts of 1mol/L hydrochloric acid (manufactured by Kanto Kagaku Co., ltd.) and 300 parts of acetone (manufactured by Kagaku Co., ltd.) were added to each other, and as a result, a yellow precipitate was formed. The mixture containing the yellow precipitate was filtered, and the residue after filtration was washed with 400 parts of water and 200 parts of methanol. Drying the obtained residue at 60deg.C under reduced pressure to obtain N represented by formula (IV) ¹ ,N ² -bis (2, 6-diisopropylphenyl) benzo [ ghi ]]Perylene-2,3,8,9,11,12-hexacarboxylic acid-2, 3,8, 9-bisimide-11, 12-anhydride (asHereinafter, sometimes referred to as compound (IV)) 15 parts (yield 75%).

< identification of Compound (IV) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 805

Accurate quality: 804

Example 1

< Compound (I-27), compound (I-25) and Compound (I-36); preparation of colorant 1

Addition of N obtained in EXAMPLE 1 ¹ ,N ² -bis (2, 6-diisopropylphenyl) benzo [ ghi ]]5.0 parts of perylene-2,3,8,9,11,12-hexacarboxylic acid-2, 3,8, 9-bisimide-11, 12-anhydride, 3.5 parts of 2-ethylhexanol (manufactured by Tokyo chemical Co., ltd.), 4.3 parts of 1-bromo-2-ethylhexane (manufactured by Tokyo chemical Co., ltd.), 3.5 parts of 1-octanol (manufactured by Tokyo chemical Co., ltd.), 4.3 parts of 1-bromooctane (manufactured by Tokyo chemical Co., ltd.), and 70 parts of N, N-dimethylformamide (manufactured by Kanto chemical Co., ltd.) were stirred at 23℃for 1 hour. Further dropwise adding 1, 8-diazabicyclo [5.4.0]4.6 parts of 7-undecene (manufactured by Tokyo chemical industry Co., ltd.) were stirred at 70℃for 6 hours. The resulting mixture was concentrated, and 30 parts of methanol was added, resulting in a yellow precipitate. The mixture containing the yellow precipitate was filtered, and the residue after filtration was washed with 5 parts of methanol. The obtained residue was dried under reduced pressure at 60℃and subjected to column purification on silica gel (solvent: chloroform), whereby 4.3 parts (yield 66%) of a mixture (colorant 1) of the compounds represented by the formulae (I-27), (I-25) and (I-36) (hereinafter, the compound represented by the formula (I-27) may be referred to as compound (I-27), the compound represented by the formula (I-25) as compound (I-25), and the compound represented by the formula (I-36) as compound (I-36)) was obtained. According to ¹ H NMR spectrum, the ratio of Compound (I-27), compound (I-25) and Compound (I-36) was 53:23:24. In the colorant 1, the compound (I-27) corresponds to the compound (Ia) of the present invention, and the compound (I-25) corresponds toThe compound (Ib) of the present invention corresponds to the compound (Ic) of the present invention.

< identification of Compound (I-27) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1047

Accurate quality: 1046

< identification of Compound (I-25) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1047

Accurate quality: 1046

< identification of Compound (I-36) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1047

Accurate quality: 1046

Example 2

< Compound (I-14), compound (I-36) and Compound (I-10); preparation of colorant 2

5.1 parts (yield 81%) of a mixture (colorant 2) of the compounds represented by the formulas (I-14), (I-36) and (I-10) (hereinafter, the compound represented by the formula (I-14) may be referred to as the compound (I-14)) and the compound represented by the formula (I-10) may be referred to as the compound (I-10)) were obtained in the same manner as in example 1 except that 3.5 parts of 1-octanol was replaced with 2.7 parts of 1-hexanol (manufactured by Tokyo chemical industry Co., ltd.), and 4.3 parts of 1-bromooctane (manufactured by Tokyo chemical industry Co., ltd.) were replaced with 3.7 parts of 1-bromohexane (manufactured by Tokyo chemical industry Co., ltd.). According to ¹ H NMR spectrum, ratio of compound (I-14), compound (I-36) and compound (I-10) was 47:28:25. In the colorant 2, the compound (I-14) corresponds to the compound (Ia) of the present invention, the compound (I-36) corresponds to the compound (Ib) of the present invention, and the compound (I-10) corresponds to the compound (Ic) of the present invention.

< identification of Compound (I-14) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1019

Accurate quality: 1018

< identification of Compound (I-36) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1047

Accurate quality: 1046

< identification of Compound (I-10) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 991

Accurate quality: 990

Example 3

< compound (I-3), compound (I-18) and compound (I-1); preparation of colorant 3

The same procedure as in example 1 was repeated except that 3.5 parts of 2-ethylhexanol was changed to 3.1 parts of 1-heptanol (manufactured by tokyo chemical industry Co., ltd.), 4.3 parts of 1-bromo-2-ethylhexane (manufactured by tokyo chemical industry Co., ltd.) was changed to 3.9 parts of 1-bromoheptane (manufactured by tokyo chemical industry Co., ltd.), 3.5 parts of 1-octanol (manufactured by 1-pentanol (manufactured by tokyo chemical industry Co., ltd.) was changed to 2.4 parts of 1-bromooctane (manufactured by 1-bromopentane chemical industry Co., ltd.) and 3.4 parts of 1-bromopentane (manufactured by tokyo chemical industry Co., ltd.) was changed to 3.4 parts, and the compound represented by the formula (I-3), the compound represented by the formula (I-18) and the formula (I-1) was sometimes referred to as compound (I-3), the compound represented by the formula (I-18) was referred to as the compound (I-18), and the compound represented by the formula (I-1) was referred to as the compound (I-1)) was changed to 2.3 part, and the mixture (colorant 3) (yield) was 5.1%). According to ¹ H NMR spectrum, ratio of compound (I-3), compound (I-18) and compound (I-1) was 49:27:24. In the colorant 3, the compound (I-3) corresponds to the compound (Ia) of the present invention, the compound (I-18) corresponds to the compound (Ib) of the present invention, and the compound (I-1) corresponds to the compound (Ic) of the present invention.

< identification of Compound (I-3) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 991

Accurate quality: 990

< identification of Compound (I-18) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1019

Accurate quality: 1018

< identification of Compound (I-1) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 963

Accurate quality: 962

Example 4

< Compound (I-4), compound (I-25) and Compound (I-1); preparation of colorant 4

A mixture (colorant 4) of the compounds represented by the formula (I-4), the formula (I-25) and the formula (I-1) (hereinafter, the compound represented by the formula (I-4) may be referred to as the compound (I-4)) was obtained in the same manner as in example 1 (yield 85%) except that 3.5 parts of 2-ethylhexanol was changed to 3.8 parts of 1-octanol (manufactured by tokyo chemical industry Co., ltd.), 4.3 parts of 1-bromo-2-ethylhexane (manufactured by tokyo chemical industry Co., ltd.), 4.3 parts of 1-bromo-3.5 parts of 1-octanol (manufactured by tokyo chemical industry Co., ltd.), and 4.3 parts of 1-bromo-2-ethyl hexane (hereinafter, the compound represented by the formula (I-4) may be referred to as the compound (I-4)) was changed to as 5.1 parts (yield 85%). According to ¹ H NMR spectrum, the ratio of Compound (I-4), compound (I-25) and Compound (I-1) was 50:25:25. In the colorant 4, the compound (I-4) corresponds to the compound (Ia) of the present invention, the compound (I-25) corresponds to the compound (Ib) of the present invention, and the compound (I-1) corresponds to the compound (Ic) of the present invention.

< identification of Compound (I-4) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1005

Accurate quality: 1004

< identification of Compound (I-25) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1047

Accurate quality: 1046

< identification of Compound (I-1) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 963

Accurate quality: 962

Example 5

< Compound (I-39), compound (I-36) and Compound (I-45); preparation of colorant 5

4.2 parts (yield 66%) of a mixture (colorant 5) of the compounds represented by the formulas (I-39), (I-36) and (I-45) (hereinafter, the compound represented by the formula (I-39) may be referred to as the compound (I-39)) was obtained in the same manner as in example 1 except that 3.5 parts of 1-octanol was replaced with 2.9 parts of benzyl alcohol (manufactured by Aldrich) and 4.3 parts of 1-bromooctane was replaced with 3.8 parts of benzyl bromide (manufactured by Tokyo chemical industry Co., ltd.). According to ¹ H NMR spectrum, ratio of compound (I-39), compound (I-36) and compound (I-45) was 47:28:25. In the colorant 5, the compound (I-39) corresponds to the compound (Ia) of the present invention, the compound (I-36) corresponds to the compound (Ib) of the present invention, and the compound (I-45) corresponds to the compound (Ic) of the present invention.

< identification of Compound (I-39) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1025

Accurate quality: 1024

< identification of Compound (I-36) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1047

Accurate quality: 1046

< identification of Compound (I-45) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1003

Accurate quality: 1002

Example 6

< Compound (I-16), compound (I-43) and Compound (I-10); preparation of colorant 6

4.6 parts (yield 74%) of a mixture (colorant 6) of the compounds represented by the formulas (I-16), (I-43) and (I-10) (hereinafter, the compound represented by the formula (I-16) may be referred to as the compound (I-16), and the compound represented by the formula (I-43)) was obtained in the same manner as in example 1, except that 3.5 parts of 2-ethylhexanol (manufactured by Tokyo chemical industry Co., ltd.) was changed to 3.0 parts of cyclohexane methanol (manufactured by Tokyo chemical industry Co., ltd.), 4.3 parts of 1-bromo-2-ethylhexane (manufactured by Tokyo chemical industry Co., ltd.) was changed to 3.9 parts of 1-octanol (manufactured by Tokyo chemical industry Co., ltd.) and 2.7 parts of 1-bromo-octane (4.5 parts of 1-octanol) (hereinafter, the compound represented by the formula (I-16) may be referred to as the compound (I-16)). According to ¹ H NMR spectrum, the ratio of Compound (I-16), compound (I-43) and Compound (I-10) was 50:24:26. In the colorant 6, the compound (I-16) corresponds to the compound (Ia) of the present invention, the compound (I-43) corresponds to the compound (Ib) of the present invention, and the compound (I-10) corresponds to the compound (Ic) of the present invention.

< identification of Compound (I-16) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1003

Accurate quality: 1002

< identification of Compound (I-43) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1015

Accurate quality: 1014

< identification of Compound (I-10) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 991

Accurate quality: 990

Example 7

< Compound (I-43) and Compound (I-10); preparation of colorant 7

Addition of N obtained in EXAMPLE 1 ¹ ,N ² -bis (2, 6-diisopropylphenyl) benzo [ ghi ]]5.0 parts of perylene-2,3,8,9,11,12-hexacarboxylic acid-2, 3,8, 9-bisimide-11, 12-anhydride, 7.8 parts of cyclohexylmethyl bromide (manufactured by Tokyo chemical industries, ltd.), 6.1 parts of cyclohexylmethanol (manufactured by Tokyo chemical industries, ltd.), 70 parts of N, N-dimethylformamide (manufactured by Kanto chemical industries, ltd.) and stirring at 23℃for 1 hour. Further dropwise adding 1, 8-diazabicyclo [5.4.0 ]4.6 parts of 7-undecene (manufactured by Tokyo chemical industry Co., ltd.) were stirred at 60℃for 6 hours. The resulting mixture was concentrated, and 30 parts of methanol was added, resulting in a yellow precipitate. The mixture containing the yellow precipitate was filtered, and the residue after filtration was washed with 5 parts of methanol. Drying the obtained residue at 60deg.C under reduced pressure, and purifying with silica gel column (solvent: chloroform) to obtain N represented by formula (I-43) ¹ ，N ² -bis (2, 6-diisopropylphenyl) benzo [ ghi ]]4.1 parts of perylene-2,3,8,9,11,12-hexacarboxylic acid-2, 3,8, 9-bisimide-11, 12-bis (cyclohexylmethyl ester) (yield 66%).

Addition of N obtained in EXAMPLE 1 ¹ ,N ² -bis (2, 6-diisopropylphenyl) benzo [ ghi ]]5.0 parts of perylene-2,3,8,9,11,12-hexacarboxylic acid-2, 3,8, 9-bisimide-11, 12-anhydride, 7.3 parts of 1-bromohexane (manufactured by Tokyo chemical Co., ltd.), 4.0 parts of 1-hexanol (manufactured by Tokyo chemical Co., ltd.), 70 parts of N, N-dimethylformamide (manufactured by Kanto chemical Co., ltd.) and stirring at 23℃for 1 hour. Further dropwise adding 1, 8-diazabicyclo [5.4.0]4.6 parts of 7-undecene (manufactured by Tokyo chemical industry Co., ltd.) were stirred at 60℃for 6 hours. The resulting mixture was concentrated, and 30 parts of methanol was added, resulting in a yellow precipitate. The mixture containing the yellow precipitate was filtered, and the residue after filtration was washed with 5 parts of methanol. The obtained residue was subjected to a temperature of 60 DEG C Drying under reduced pressure, purifying with silica gel column (solvent: chloroform), and obtaining N represented by formula (I-10) ¹ ,N ² -bis (2, 6-diisopropylphenyl) benzo [ ghi ]]4.3 parts of perylene-2,3,8,9,11,12-hexacarboxylic acid-2, 3,8, 9-bisimide-11, 12-bis (1-hexyl ester) (yield 70%).

10 parts of Compound (I-43), 10 parts of Compound (I-10) and 200 parts of methylene chloride (manufactured by Kabushiki Kaisha) were added and stirred at 23℃for 1 hour. The obtained solution was concentrated to obtain 20 parts of a mixture (colorant 7) of the compound (I-43) and the compound (I-10). In the colorant 7, the compound (I-43) corresponds to the compound (Ib) of the present invention, and the compound (I-10) corresponds to the compound (Ic) of the present invention.

< identification of Compound (I-43) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1015

Accurate quality: 1014

< identification of Compound (I-10) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 991

Accurate quality: 990

Synthesis example 2

< preparation of Lumogen (registered trademark) F Yellow083 >

Lumogen (registered trademark) F Yellow083 represented by the following formula (x) was synthesized in accordance with the description of Japanese patent application laid-open No. 60-203650.

Synthesis example 3

< preparation of Compound INT >

10 parts of 1,6,7, 12-tetrachloro-3, 4,9, 10-perylene dianhydride (Combinatorial Chemistry Co., ltd.), 13 parts of 2, 6-diisopropylaniline (Tokyo chemical industry Co., ltd.) and 188 parts of propionic acid were added, and stirred under reflux for 20 hours. The resulting mixture was kept below 20℃while 50 parts of water was added, resulting in an orange precipitate. The mixture containing the orange precipitate was filtered, and the residue after filtration was washed with 200 parts of water and 100 parts of methanol. The obtained residue was dried under reduced pressure at 60℃to obtain 12 parts of an intermediate compound (hereinafter, sometimes referred to as compound INT) (yield 75%).

< identification of Compound INT >

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 847

Accurate quality: 846

Synthesis example 4

< preparation of Compound (II-16) >)

5.0 parts of the produced compound INT, 1.5 parts of 4-chlorophenol (manufactured by Tokyo chemical Co., ltd.), 3.1 parts of 4-tert-butylphenol (manufactured by Tokyo chemical Co., ltd.), 11 parts of potassium carbonate (manufactured by Kato chemical Co., ltd.), and 295 parts of N-methylpyrrolidone (manufactured by Kato chemical Co., ltd.) were added, and stirred at 130℃for 13 hours. The resulting mixture was kept at 20℃or lower, and 29 parts of 37% hydrochloric acid (manufactured by Kagaku Co., ltd.) and 142 parts of water were added simultaneously, so that a dark red precipitate was formed. The mixture containing the dark red precipitate was filtered, and the residue after filtration was washed with 300 parts of water and 150 parts of methanol. The obtained residue was dried under reduced pressure at 60℃to obtain 6.1 parts (yield: 81%) of a compound represented by the formula (II-16) (hereinafter, sometimes referred to as compound (II-16)).

< identification of Compound (II-16) >)

Ionization mode = ESI +: m/z= [ m+h ]] ⁺ 1237

Accurate quality: 1236

Synthesis example 5

The compound represented by the following formula (II-3) (hereinafter, sometimes referred to as compound (II-3)) is obtained from Tokyo chemical industry Co., ltd.

Synthesis example 6

< preparation of resin B1 >

A flask equipped with a reflux condenser, a dropping funnel and a stirrer was charged with an appropriate amount of nitrogen, the nitrogen atmosphere was replaced with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was added thereto, and the mixture was heated to 80℃while stirring. Next, 38 parts of acrylic acid, 3, 4-epoxytricyclo [5.2.1.0 ] was added dropwise over 5 hours ^2,6 ]Decan-8-yl ester and acrylic acid 3, 4-epoxytricyclo [5.2.1.0 ^2,6 ]Decane-9-yl ester (molar ratio 1:1) 289 parts, propylene glycol monomethyl ether acetate 125 parts. On the other hand, a solution obtained by dissolving 33 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was kept at 80℃for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution having a solid content of 35.1% and a viscosity of 125 mPas measured by a B-type viscometer (23 ℃). The resulting copolymer had a weight average molecular weight Mw of 9.2X10 ³ The dispersity was 2.08, and the acid value in terms of solid content was 77mg-KOH/g. The resin B1 has the following structural units.

Example 8 >

(1) Solubility test of colorant in solvent (propylene glycol monomethyl ether acetate; hereinafter sometimes referred to as PGMEA)

About 50mg of a solute (colorant 1; a mixture of Compound (I-27), compound (I-25) and Compound (I-36)) was weighed into a 20mL screw tube. To this was added about 500mg of solvent (PGMEA), and the total amount of solute and solvent was weighed. After stirring for 30 minutes in a thermostatic bath at 20 ℃, when dissolution was visually confirmed, the solubility was determined as a value calculated from the mass of the solute relative to the total mass of the solute and the solvent. When the solvent was not dissolved, 500mg of the solvent was continuously added until the solvent was dissolved, and the mixture was stirred with a MIX ROTOR in a constant temperature bath at 20℃for 30 minutes at each addition, and the solubility was determined as a value calculated by visually checking the mass of the solute relative to the total mass of the solute and the solvent at the time of dissolution. The results are shown in Table 3.

(2) Preparation of coloring composition

The respective components were mixed in the following proportions to obtain a coloring composition 1.

(A) Coloring agent: colorant 1.6 parts

(B) Resin: 58 parts of resin B1 solution

(E) Solvent: 420 parts of propylene glycol monomethyl ether acetate

(3) Preparation of colored resin composition

Next, the respective components were mixed in the following proportions to obtain a colored resin composition 1.

480.6 parts of coloring composition

(C) Polymerizable compound: dipentaerythritol hexaacrylate

(Kayarad (registered trademark) DPHA; manufactured by Kayarad Co., ltd.) 40 parts

(D) Polymerization initiator: 2 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE 01, manufactured by BASF corporation)

(F) Leveling agent: 0.15 part of polyether modified silicone oil (Toray Silicone SH8400: dow Corning Toray (manufactured by Kyowa Co., ltd.)

(4) Production of colored coating film (color Filter)

The colored resin composition was applied to a 5cm square glass substrate (EAGLE XG; manufactured by Corning) by spin coating so that the film thickness after post-baking became 1.9 to 2.1. Mu.m, and then pre-baked at 100℃for 3 minutes to form a colored composition layer. After the cooling-down of the water tank, the water tank is cooled down,a coloring composition layer formed on a substrate was subjected to an exposure machine (TME-150 RSK; TOPCON Co., ltd.) at 80mJ/cm under an atmospheric atmosphere ² The exposure amount (365 nm reference) of the substrate was irradiated with light. After the light irradiation, post-baking was performed in an oven at 230℃for 30 minutes to obtain a colored coating film.

The chromaticity evaluation of the colored coating film was carried out by measuring the spectrum using a colorimeter (OSP-SP-200; manufactured by Olympus, inc.), and measuring the xy chromaticity coordinates (x, Y) and Y in the XYZ color system of CIE using the characteristic function of the C light source.

(5) Determination of fluorescence intensity

The fluorescence spectrum of the obtained colored coating film was measured using a fluorescence spectrophotometer (FluoMAX-3; horikoshi corporation) (excitation side slit 5nm, fluorescence side slit 10nm, excitation wavelength 460 nm), and the fluorescence intensity at the fluorescence wavelength was obtained. Here, the fluorescence wavelength refers to a wavelength at which the intensity of the fluorescence spectrum is maximum (peak of the fluorescence spectrum). The fluorescence intensity in this test was evaluated by setting the fluorescence intensity of comparative example 1 to 100. If the fluorescence intensity exceeds 100, this means that the fluorescence intensity is higher than that of the colored coating film of comparative example 1. The results are shown in Table 3.

(6) Test of Heat resistance

The resulting colored coating film was heated in an oven at 230℃for 180 minutes under an atmospheric atmosphere. From the xy chromaticity coordinates (x, Y) and Y measured values before and after the test, JIS Z8730 was used: 2009 (7. Method for calculating color difference) calculating color difference ΔE by the method described in ^* ab. Color difference delta E ^* The smaller the value of ab means the smaller the color change, if ΔE ^* If ab is 3 or less, the colored coating film is said to have no practical problem as a color filter. Before and after the heat resistance test, a fluorescence spectrum was measured using a fluorescence spectrophotometer (FluoMAX-3; horiba corporation) (excitation side slit 5nm, fluorescence side slit 10nm, excitation wavelength 460 nm), and the fluorescence intensity maintaining ratio at the fluorescence wavelength was determined. The fluorescence intensity maintenance rate in the present test is a value obtained by setting the fluorescence intensity of the colored coating film before the heat resistance test to 100%. Fluorescence intensity dimensionThe higher the holding ratio, the better the heat resistance. In addition, if the heat resistance of the colored coating film is good, the colored pattern made of the same colored resin composition can also be said to be good in heat resistance. The results are shown in Table 3.

(7) Light fastness test

An ultraviolet cut filter (COLORED OPTICAL GLASS L; manufactured by HOYA Co., ltd., cut off light of 380nm or less) was placed on the obtained colored coating film, and a xenon lamp light was irradiated with a light resistance tester (SUNTEST CPS +: manufactured by Toyo Seisakusho Co., ltd.) for 48 hours. From the xy chromaticity coordinates (x, Y) and Y measured values before and after the test, JIS Z8730 was used: 2009 (7. Method for calculating color difference) calculating color difference ΔE by the method described in ^* ab. Color difference delta E ^* The smaller the value of ab means the smaller the color change, if ΔE ^* If ab is 3 or less, the coating film is said to have no practical problem as a color filter. Before and after the light resistance test, a fluorescence spectrum was measured using a fluorescence spectrophotometer (FluoMAX-3; horiba corporation) (excitation side slit 5nm, fluorescence side slit 10nm, excitation wavelength 460 nm), and the fluorescence intensity maintaining ratio at the fluorescence wavelength was determined. The fluorescence intensity maintenance rate in the present test is a value obtained by setting the fluorescence intensity of the colored coating film before the light resistance test to 100%. The higher the fluorescence intensity maintenance rate means the better the light resistance. In addition, if the light resistance of the colored coating film is good, the colored pattern produced from the same colored resin composition can also be said to be good in light resistance. The results are shown in Table 3.

Examples 9 to 14 and comparative example 1 >

A colored coating film was produced in the same manner as in example 8 except that 2.6 parts of colorant 2 (example 9), 2.6 parts of colorant 3 (example 10), 2.6 parts of colorant 4 (example 11), 2.6 parts of colorant 5 (example 12), 2.6 parts of colorant 6 (example 13), 2.6 parts of colorant 7 (example 14) or 2.6 parts of Lumogen (registered trademark) fyellow 083 (comparative example 1) was used as a colorant in place of 2.6 parts of colorant 1. The solubility in PGMEA of the mixture of the compounds used as colorants in the examples or the compound used in comparative example 1, and the fluorescence intensity measurement results, heat resistance test results and light resistance test results of the respective colored coating films are shown in table 3.

TABLE 3

Comparative example 2 >

When a colored resin composition and a colored coating film were attempted to be produced using 2.6 parts of the compound (I-43) as a colorant instead of 2.6 parts of the colorant 1 of example 8, the compound (I-43) was hardly soluble in PGMEA, and the colored coating film could not be obtained because of the difficulty in PGMEA.

Comparative example 3 >

A colored resin composition was obtained in the same manner as in example 8 except that 2.6 parts of the compound (I-10) was used as a colorant in place of 2.6 parts of the colorant 1. The solubility of the compound (I-10) in PGMEA and the results of the light resistance test of the resulting colored coating film were combined with the results of example 14 and comparative example 2, and are shown in Table 4.

TABLE 4

From the results of example 14, comparative examples 2 and 3, it was found that a colored coating film excellent in light resistance could not be obtained when a colorant containing 1 kind of compound (I) was used, if R containing formula (I) was used ¹ At least 2 kinds of colorants (A) of the compound (I) different from each other, a colored coating film excellent in light resistance is obtained.

Example 15 >

The respective components were mixed in the following proportions to obtain coloring compositions 1 to 2.

(A) Coloring agent: colorant 1.3 parts

2.6 parts of Compound (II-16)

(B) Resin: 54 parts of resin B1 solution

(E) Solvent: 420 parts of propylene glycol monomethyl ether acetate

A colored resin composition was obtained in the same manner as in example 8 except that the colored composition 1-2 was used instead of the colored composition 1, and a colored coating film was produced. The fluorescence intensity measurement results, heat resistance test results and light resistance test results of the obtained colored coating film are shown in table 5.

Examples 16 to 21 and comparative examples 4 and 5 >, respectively

A colored coating film was produced in the same manner as in example 15 except that 1.3 parts of colorant 2 (example 16), 1.3 parts of colorant 3 (example 17), 1.3 parts of colorant 4 (example 18), 1.3 parts of colorant 5 (example 19), 1.3 parts of colorant 6 (example 20), 1.3 parts of colorant 7 (example 21), or 1.3 parts of Lumogen (registered trademark) fyellow 083 (comparative example 4) was used instead of 1.3 parts of colorant 1. The results of the fluorescence intensity measurement, the heat resistance test and the light resistance test of each colored coating film are shown in Table 5.

Example 22 >

The respective components were mixed in the following proportions to obtain coloring compositions 1 to 3.

(A) Coloring agent: colorant 1.3 parts

2.6 parts of Compound (II-3)

(B) Resin: 54 parts of resin B1 solution

(E) Solvent: 420 parts of propylene glycol monomethyl ether acetate

A colored resin composition was obtained in the same manner as in example 8 except that the colored compositions 1 to 3 were used instead of the colored composition 1, and a colored coating film was produced. The fluorescence intensity measurement results, heat resistance test results and light resistance test results of the obtained colored coating film are shown in table 5.

Examples 23 to 24 and comparative example 5 >

A colored coating film was produced in the same manner as in example 22 except that 1.3 parts of colorant 6 (example 23), 1.3 parts of colorant 7 (example 24), or 1.3 parts of Lumogen (registered trademark) fyellow 083 (comparative example 5) was used instead of 1.3 parts of colorant 1. The results of the fluorescence intensity measurement, the heat resistance test and the light resistance test of each colored coating film are shown in Table 5.

TABLE 5

From the above results, it was found that the colored coating film formed from the colored resin composition containing the compound (Ia) or the colorant (a) of the present invention is excellent in light resistance. In addition, it was found that the compound (Ia) and the colorant (a) of the present invention have high solubility in the solvent (PGMEA) and good solubility. Further, it is known that a colored coating film formed from a colored resin composition containing the compound (Ia) or the colorant (a) of the present invention has high fluorescence intensity and excellent heat resistance.

Claims

1. A colorant comprising at least 2 kinds of compounds represented by the formula (I),

the 2 compounds represented by the formula (I) are at least R of the formula (I) ¹ The compounds that are different from each other,

in the formula (I) of the present invention,

R ¹ and R is ² Independently of each other, a hydrocarbon group having 5 to 8 carbon atoms,

R ³ and R is ⁸ Independently of each other, represents a group obtained by combining an aromatic hydrocarbon group having 6 to 12 carbon atoms with a saturated chain hydrocarbon group having 1 to 8 carbon atoms,

R ⁴ 、R ⁵ 、R ⁶ 、R ⁷ 、R ⁹ and R is ¹⁰ Represents a hydrogen atom.

2. The colorant according to claim 1, wherein at least the combination of (I), (ii) or (iii) as the compound represented by the formula (I) contains at least 2 compounds selected from the group consisting of the compound represented by the formula (Ia), the compound represented by the formula (Ib) and the compound represented by the formula (Ic),

(i) A combination of a compound represented by the formula (Ia) and a compound represented by the formula (Ib),

(ii) A combination of a compound represented by the formula (Ia) and a compound represented by the formula (Ic),

(iii) A combination of a compound represented by the formula (Ib) and a compound represented by the formula (Ic),

in formula (Ia), formula (Ib) and formula (Ic),

R ^1a 、R ^2a 、R ^1b and R is ^1c Independently of each other, represents a hydrocarbon group having 5 to 8 carbon atoms, wherein R ^1a And R is R ^2a Different, R ^1b And R is R ^1c The differences are not the same and,

R ³ ～R ¹⁰ the same meaning as described above is indicated.

3. The colorant according to claim 2, wherein at least one of the combination of (i) and the combination of (ii) is satisfied,

4. The colorant according to claim 2 or 3, wherein at least 1 compound represented by the formula (Ia), at least 1 compound represented by the formula (Ib) and at least 1 compound represented by the formula (Ic), respectively,

the content of the compound represented by the formula (Ia) is 35 to 65 mol%,

the content of the compound represented by the formula (Ib) is 15 to 35 mol%,

the content of the compound represented by the formula (Ic) is 15 to 35 mol%.

5. The colorant according to any one of claims 1 to 3, further comprising a perylene compound.

6. A colored resin composition comprising the colorant according to any one of claims 1 to 5 and a resin.

7. The colored resin composition according to claim 6, further comprising a polymerizable compound and a polymerization initiator.

8. The colored resin composition according to claim 6 or 7, further comprising a solvent.

9. A color filter formed from the colored resin composition according to any one of claims 6 to 8.

10. A display device comprising the color filter of claim 9.

11. A compound represented by the formula (Ia),

in the formula (Ia),

R ^1a and R is ^2a Independently of each other, a hydrocarbon group having 5 to 8 carbon atoms,R ^1a and R is R ^2a The differences are not the same and,