JP2024014738A - Coloring compositions and compounds - Google Patents

Abstract

An object of the present invention is to provide a colored composition and a coloring agent that can produce a coating film with high transmittance at 630 nm. The coloring composition and colorant of the present invention are characterized by containing a compound represented by formula (I). TIFF2024014738000050.tif2192 [In formula (I), R1 and R3 each independently represent a hydrocarbon group, a heterocyclic group, a cyano group, or a halogen atom, which may have a substituent, and R2, R4 and R5 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, a cyano group, or a halogen atom. X1 represents a substituent or a hydrocarbon group which may have a substituent. n represents an integer from 0 to 4. When n represents an integer of 2 or more and X1 is bonded to adjacent carbon atoms, X1 bonded to adjacent carbon atoms may be bonded to each other to form a ring. -CH2- contained in the ring skeleton may be replaced with -O-, -CO- or -NH-, and -CH= contained in the ring skeleton may be replaced with -N=. good. ] [Selection diagram] None

Description

The present invention relates to a colorant, a coloring composition containing the colorant, a color filter formed from the coloring composition, and a display device containing the color filter.

Color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors are manufactured from colored compositions. It is known to use a compound represented by formula (a-1) and a compound represented by formula (X1) as a colorant used in such a coloring composition (Patent Document 1).

International Publication No. 2022/065357

In color filters, in order to improve color performance, it is required to further increase the transmittance of a target wavelength. For example, as a red color filter, it is preferable that the transmittance at 630 nm is high. Therefore, an object of the present invention is to provide a colorant and a coloring composition that can produce a coating film with high transmittance at 630 nm.

［式（Ｉ）中、
Ｒ¹及びＲ³は、それぞれ独立して、置換基を有していてもよい炭化水素基、複素環基、シアノ基、又はハロゲン原子を表す。
Ｒ²、Ｒ⁴及びＲ⁵は、それぞれ独立して、水素原子、置換基を有していてもよい炭化水素基、複素環基、シアノ基、又はハロゲン原子を表す。
Ｘ¹は、置換基或いは置換基を有していてもよい炭化水素基を表す。
ｎは０～４の整数を表す。ｎが２以上の整数を表す場合、複数のＸ¹は同一であっても異なっていてもよい。ｎが２以上の整数を表し、且つＸ¹が隣接する炭素原子に結合している場合、隣接する炭素原子に結合するＸ¹は互いに結合して環を形成してもよい。該環の骨格に含まれる－ＣＨ₂－は、－Ｏ－、－ＣＯ－又は－ＮＨ－に置き換わっていてもよく、該環の骨格に含まれる－ＣＨ＝は、－Ｎ＝に置き換わっていてもよい。］
［２］ さらに顔料を含む［１］に記載の着色組成物。
［３］ さらにアルカリ可溶性樹脂を含む［１］又は［２］に記載の着色組成物。
［４］ さらに、溶剤、重合性化合物及び重合開始剤を含む［１］～［３］のいずれかに記載の着色組成物。
［５］ ［１］～［４］のいずれかに記載の着色組成物から形成されるカラーフィルタ。
［６］ ［５］に記載のカラーフィルタを含む表示装置。
［７］ 式（Ｉ）で表される化合物。

［式（Ｉ）中、
Ｒ¹及びＲ³は、それぞれ独立して、置換基を有していてもよい炭化水素基、複素環基、シアノ基、又はハロゲン原子を表す。
Ｒ²、Ｒ⁴及びＲ⁵は、それぞれ独立して、水素原子、置換基を有していてもよい炭化水素基、複素環基、シアノ基、又はハロゲン原子を表す。
Ｘ¹は、置換基或いは置換基を有していてもよい炭化水素基を表す。
ｎは０～４の整数を表す。ｎが２以上の整数を表す場合、複数のＸ¹は同一であっても異なっていてもよい。ｎが２以上の整数を表し、且つＸ¹が隣接する炭素原子に結合している場合、隣接する炭素原子に結合するＸ¹は互いに結合して環を形成してもよい。該環の骨格に含まれる－ＣＨ₂－は、－Ｏ－、－ＣＯ－又は－ＮＨ－に置き換わっていてもよく、該環の骨格に含まれる－ＣＨ＝は、－Ｎ＝に置き換わっていてもよい。］ The gist of the invention is as follows.
[1] A colored composition containing a compound represented by formula (I).

[In formula (I),
R ¹ and R ³ each independently represent a hydrocarbon group, a heterocyclic group, a cyano group, or a halogen atom that may have a substituent.
R ² , R ⁴ and R ⁵ each independently represent a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, a cyano group, or a halogen atom.
X ¹ represents a substituent or a hydrocarbon group which may have a substituent.
n represents an integer from 0 to 4. When n represents an integer of 2 or more, the plurality of X ¹ may be the same or different. When n represents an integer of 2 or more and X ¹ is bonded to adjacent carbon atoms, X ¹ bonded to adjacent carbon atoms may be bonded to each other to form a ring. -CH ₂ - contained in the ring skeleton may be replaced with -O-, -CO- or -NH-, and -CH= contained in the ring skeleton may be replaced with -N=. Good too. ]
[2] The colored composition according to [1], further comprising a pigment.
[3] The colored composition according to [1] or [2], further comprising an alkali-soluble resin.
[4] The colored composition according to any one of [1] to [3], further comprising a solvent, a polymerizable compound, and a polymerization initiator.
[5] A color filter formed from the colored composition according to any one of [1] to [4].
[6] A display device including the color filter according to [5].
[7] A compound represented by formula (I).

[In formula (I),
R ¹ and R ³ each independently represent a hydrocarbon group, a heterocyclic group, a cyano group, or a halogen atom that may have a substituent.
R ² , R ⁴ and R ⁵ each independently represent a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, a cyano group, or a halogen atom.
X ¹ represents a substituent or a hydrocarbon group which may have a substituent.
n represents an integer from 0 to 4. When n represents an integer of 2 or more, the plurality of X ¹ may be the same or different. When n represents an integer of 2 or more and X ¹ is bonded to adjacent carbon atoms, X ¹ bonded to adjacent carbon atoms may be bonded to each other to form a ring. -CH ₂ - contained in the ring skeleton may be replaced with -O-, -CO- or -NH-, and -CH= contained in the ring skeleton may be replaced with -N=. Good too. ]

According to the colorant and coloring composition of the present invention, it is possible to increase the transmittance at 630 nm of the resulting coating film. In a preferred embodiment, the colorant and coloring composition of the present invention can reduce foreign matter between line patterns after development.

<Compound (I)>
The compound according to the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)).

［式（Ｉ）中、
Ｒ¹及びＲ³は、それぞれ独立して、置換基を有していてもよい炭化水素基、複素環基、シアノ基、又はハロゲン原子を表す。
Ｒ²、Ｒ⁴及びＲ⁵は、それぞれ独立して、水素原子、置換基を有していてもよい炭化水素基、複素環基、シアノ基、又はハロゲン原子を表す。
Ｘ¹は、置換基或いは置換基を有していてもよい炭化水素基を表す。
ｎは０～４の整数を表す。ｎが２以上の整数を表す場合、複数のＸ¹は同一であっても異なっていてもよい。ｎが２以上の整数を表し、且つＸ¹が隣接する炭素原子に結合している場合、隣接する炭素原子に結合するＸ¹は互いに結合して環を形成してもよい。該環の骨格に含まれる－ＣＨ₂－は、－Ｏ－、－ＣＯ－又は－ＮＨ－に置き換わっていてもよく、該環の骨格に含まれる－ＣＨ＝は、－Ｎ＝に置き換わっていてもよい。］

[In formula (I),
R ¹ and R ³ each independently represent a hydrocarbon group, a heterocyclic group, a cyano group, or a halogen atom that may have a substituent.
R ² , R ⁴ and R ⁵ each independently represent a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, a cyano group, or a halogen atom.
X ¹ represents a substituent or a hydrocarbon group which may have a substituent.
n represents an integer from 0 to 4. When n represents an integer of 2 or more, the plurality of X ¹ may be the same or different. When n represents an integer of 2 or more and X ¹ is bonded to adjacent carbon atoms, X ¹ bonded to adjacent carbon atoms may be bonded to each other to form a ring. -CH ₂ - contained in the ring skeleton may be replaced with -O-, -CO- or -NH-, and -CH= contained in the ring skeleton may be replaced with -N=. Good too. ]

Compound (I) will be described in detail below. Compound (I) has a resonance structure of formula (I), a tautomer of formula (I), and each group in formula (I) This also includes compounds obtained by rotating around the bond axis. Examples of the tautomer of formula (I) include compounds represented by formula (I') below.

［式（Ｉ’）中、Ｒ¹～Ｒ⁵、Ｘ¹及びｎは上記と同じである。］

[In formula (I'), R ¹ to R ⁵ , X ¹ and n are the same as above. ]

The hydrocarbon groups represented by R ¹ to R ⁵ and X ¹ include aliphatic hydrocarbon groups and aromatic hydrocarbon groups, and the aliphatic hydrocarbon groups may be saturated or unsaturated. , may be linear or cyclic (alicyclic hydrocarbon group). Further, the alicyclic hydrocarbon group may be monocyclic or polycyclic.

Saturated chain hydrocarbon groups (hereinafter sometimes referred to as alkyl groups) include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, Linear alkyl groups such as n-octyl group, n-nonyl group, and n-decyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 1,3-dimethylbutyl group, 2-ethylbutyl group and branched alkyl groups such as 2-ethylhexyl group.

Examples of unsaturated chain hydrocarbon groups include alkenyl groups such as ethenyl group, propenyl group (e.g., 1-propenyl group, 2-propenyl group), and butenyl group (e.g., 1-butenyl group, 3-butenyl group); Examples include alkynyl groups such as ethynyl group, propynyl group (eg, 1-propynyl group, 2-propynyl group), butynyl group (eg, 1-butynyl group, 3-butynyl group), and the like.

The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 10, more preferably 1 to 6, and still more preferably 1 to 4.

Examples of the saturated alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and 2-methylcyclohexyl group.

Examples of the unsaturated alicyclic hydrocarbon group include a cyclohexenyl group (e.g., cyclohex-1-en-1-yl group, cyclohex-2-en-1-yl group, cyclohex-3-en-1-yl group); , cycloalkenyl groups such as cycloheptenyl group and cyclooctenyl group.

Examples of alicyclic hydrocarbon groups include polycyclic saturated alicyclic hydrocarbon groups such as norbornyl group, adamantyl group, and bicyclo[2.2.2]octyl group; polycyclic unsaturated alicyclic groups such as norbornenyl group; Also included are cyclic hydrocarbon groups; and the like.

The alicyclic hydrocarbon group preferably has 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and still more preferably 3 to 8 carbon atoms.

Aromatic hydrocarbon groups include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-dimethylphenyl group, 2,6-dimethylphenyl group, 2,4,6-trimethylphenyl group. group, 2,4-diisopropylphenyl group, 2,6-diisopropylphenyl group, 4-vinylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3, Examples include 5-di(tert-butyl)phenyl group, 1-naphthyl group, 2-naphthyl group, and a group obtained by removing one hydrogen atom from tetralin.

The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and still more preferably 6 to 10 carbon atoms.

The hydrocarbon group represented by R ¹ to R ⁵ and X ¹ may be a combination of the hydrocarbon groups listed above, and examples of the combination of hydrocarbon groups include an aralkyl group, Examples thereof include an alkyl group to which an alicyclic hydrocarbon group is bonded, an aromatic hydrocarbon group to which a cycloalkyl group is condensed, and an alkyl group to which an aromatic hydrocarbon group to which a cycloalkyl group is condensed are bonded.

Examples of the aralkyl group include benzyl group, (4-methylphenyl)methyl group, and phenethyl group. The aralkyl group preferably has 7 to 18 carbon atoms, more preferably 7 to 12 carbon atoms, and still more preferably 7 to 10 carbon atoms.

Examples of the alkyl group to which an alicyclic hydrocarbon group is bonded include a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, and an adamantylmethyl group. The number of carbon atoms in the alkyl group to which the alicyclic hydrocarbon group is bonded is preferably 4 to 20, more preferably 4 to 15, and still more preferably 4 to 10.

Examples of aromatic hydrocarbon groups fused with a cycloalkyl group include a group in which one hydrogen atom is removed from the benzene ring in indane, a group in which one hydrogen atom is removed from the benzene ring in 1-methyl-indane, and a group in which one hydrogen atom is removed from the benzene ring in indane, and 2-methyl- Examples include a group obtained by removing one hydrogen atom from the benzene ring in indane.

Examples of alkyl groups to which an aromatic hydrocarbon group to which a cycloalkyl group is condensed include a group in which an alkyl group having 1 to 4 carbon atoms is bonded to a benzene ring in indane, and a group in which an alkyl group having 1 to 4 carbon atoms is bonded to a benzene ring in 1-methyl-indane. Examples thereof include a group in which 4 alkyl groups are bonded, and a group in which an alkyl group having 1 to 4 carbon atoms is bonded to a benzene ring in 2-methyl-indane.

The hydrocarbon groups represented by R ¹ to R ⁵ and X ¹ may have a substituent. When the hydrocarbon group has a substituent, it may have one type of substituent or two or more types of substituents.

Substituents that the hydrocarbon groups represented by R ¹ to R ⁵ may have (hereinafter sometimes referred to as substituent A) include hydroxy group, alkoxy group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. ~4 alkylsulfanyl groups, carboxy groups, substituted or unsubstituted amino groups, N-acylamino groups, cyano groups, halogen atoms, -SO ₃ H, -SO ₃ M, -SO ₃ T _0.5 , -SO ₂ N ( R ⁶ ) _2, etc., including hydroxy group, alkoxy group having 1 to 4 carbon atoms, alkylsulfanyl group having 1 to 4 carbon atoms, carboxy group, substituted or unsubstituted amino group, N-acylamino group, cyano group, A halogen atom is preferred, and an alkoxy group having 1 to 4 carbon atoms and a halogen atom are more preferred. M represents an alkali metal atom, T represents an alkaline earth metal atom, and R ⁶ represents a hydrogen atom or a hydrocarbon group.

Substituents that the hydrocarbon group represented by X ¹ may have (hereinafter sometimes referred to as substituent B) include substituted or unsubstituted amino groups, N-acylamino groups, carboxy groups, Examples include an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a cyano group, a halogen atom, and a hydroxy group.

The amino groups as substituents A and B may be unsubstituted amino groups or substituted amino groups. Preferably, the substituted amino group is an amino group having one or two hydrocarbon groups. Examples of the hydrocarbon group include groups similar to the hydrocarbon groups represented by R ¹ to R ⁵ and X ¹ , preferably an alkyl group or an aromatic hydrocarbon group, and a group having 1 to 4 carbon atoms. It is more preferably an alkyl group or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms. Examples of the substituted amino group include N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, Examples include N-isopropylamino group, N,N-diisopropylamino group, N-phenylamino group, N,N-diphenylamino group, and N,N-ethylmethylamino group.

The N-acylamino group as substituents A and B means a group represented by -NHCOR ⁷ , where R ⁷ represents a hydrogen atom or a hydrocarbon group. Examples of the hydrocarbon group represented by R ⁷ include the same groups as the hydrocarbon groups represented by R ¹ to R ⁵ and X ¹ described above. R ⁷ is preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms. Examples of the N-acylamino group include N-formylamino group, N-acetylamino group, N-propanoylamino group, N-butanoylamino group, and N-benzoylamino group.

Examples of the alkoxy group as substituents A and B include methoxy group, ethoxy group, propoxy group, n-butoxy group, and tert-butoxy group. The alkoxy group preferably has 1 to 4 carbon atoms, more preferably 1 or 2 carbon atoms.

Examples of the alkylsulfanyl group as substituents A and B include methylsulfanyl group, ethylsulfanyl group, propylsulfanyl group, n-butylsulfanyl group, and the like. The alkylsulfanyl group preferably has 1 to 4 carbon atoms, more preferably 1 or 2 carbon atoms.

Examples of the halogen atom as substituents A and B include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among them, a fluorine atom, a chlorine atom, or a bromine atom is preferable, and a chlorine atom is more preferable. .

Examples of the alkali metal atom represented by M include sodium, potassium, and the like.

Examples of the alkaline earth metal atom represented by T include magnesium, calcium, barium, and the like. When any of R ¹ to R ⁵ is a hydrocarbon group having one -SO ₃ T _0.5 , compound (I) has the following structure.

［式中、Ｒ¹～Ｒ⁵、Ｘ¹、ｎ及びＴは、上記と同じ意味を表す。－ＳＯ₃ ^-は、Ｒ¹～Ｒ⁵で表される炭化水素基が有する水素原子のいずれかを置換している。］

[In the formula, R ¹ to R ⁵ , X ¹ , n and T have the same meanings as above. --SO ₃ ^-- substitutes any hydrogen atom of the hydrocarbon group represented by R ¹ to R ⁵ . ]

R ⁶ represents a hydrogen atom or a hydrocarbon group. The two R ⁶ 's may be the same or different, and preferably one is a hydrogen atom and the other is a hydrocarbon group. Examples of the hydrocarbon group represented by R ⁶ include the groups described above as the hydrocarbon groups represented by R ¹ to R ⁵ and X ¹ , including alkyl groups having 1 to 10 carbon atoms, and 10 cycloalkyl groups, polycyclic saturated alicyclic hydrocarbon groups having 3 to 12 carbon atoms, and aromatic hydrocarbon groups having 6 to 18 carbon atoms.

The heterocyclic group represented by R ¹ to R ⁵ may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a ring constituent. Examples of heteroatoms include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of carbon atoms in the heterocyclic group is preferably 2 to 30, more preferably 3 to 22, and even more preferably 3 to 20.

Examples of heterocycles containing only nitrogen atoms as heteroatoms include monocyclic heterocyclic groups such as pyrrolyl group, imidazolyl group, pyrazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, etc. polycyclic heterocyclic groups such as indolizinyl group, indolyl group, 1H-indazolyl group, isoquinolyl group, quinolyl group, phthalazinyl group, carbazolyl group, acridinyl group, indolinyl group, isoindolinyl group; and the like.
Examples of heterocycles containing only oxygen atoms as heteroatoms include monocyclic heterocyclic groups such as furyl group and pyranyl group; polycyclic heterocyclic groups such as isobenzofuranyl group, chromenyl group, xanthenyl group, and chromanyl group; etc.
Examples of the heterocycle containing only a sulfur atom as a heteroatom include monocyclic heterocyclic groups such as a thienyl group; polycyclic heterocyclic groups such as a benzo[b]thienyl group and a thianthrenyl group; and the like.
Examples of the heterocycle containing a nitrogen atom and an oxygen atom as heteroatoms include polycyclic heterocyclic groups such as a benzimidazolonyl group.
Among these, polycyclic heterocyclic groups are preferred, such as benzo[b]thienyl group, thianthrenyl group, isobenzofuranyl group, chromenyl group, xanthenyl group, indolyl group, 1H-indazolyl group, isoquinolyl group, quinolyl group, phthalazinyl group, More preferred are polycyclic heterocyclic groups having a benzene ring, such as a carbazolyl group, an acridinyl group, a chromanyl group, an indolinyl group, an isoindolinyl group, and a benzimidazolonyl group.

Examples of the halogen atom represented by R ¹ to R ⁵ include fluorine atom, chlorine atom, bromine atom, and iodine atom, among which chlorine atom and fluorine atom are preferred.

The substituent represented by X ¹ (hereinafter sometimes referred to as substituent -4 alkylsulfanyl groups, cyano groups, halogen atoms, etc.

Substituted or unsubstituted amino group, N-acylamino group, alkoxy group having 1 to 4 carbon atoms, alkylsulfanyl group having 1 to 4 carbon atoms as substituent X, and halogen atom as substituents A and B. Substituted or unsubstituted amino groups, N-acylamino groups, alkoxy groups having 1 to 4 carbon atoms, alkylsulfanyl groups having 1 to 4 carbon atoms, and groups similar to those described as halogen atoms can be used.

n represents an integer from 0 to 4. When n represents an integer of 2 or more, the plurality of X ¹ may be the same or different. When n represents an integer of 2 or more, and multiple X ^1s are bonded to adjacent carbon atoms among the carbon atoms constituting the phenylene group, the X ^1s bonded to the adjacent carbon atoms are bonded to each other. may be used to form a ring. -CH ₂ - contained in the ring skeleton may be replaced with -O-, -CO- or -NH-, and -CH= contained in the ring skeleton may be replaced with -N=. Good too. Examples of the ring formed by combining X ¹ with each other include the following. In the formula, * indicates a bond with an adjacent carbon atom on the phenylene group.

R ¹ and R ³ are each independently,
It is preferable that it is a hydrocarbon group that may have a substituent,
An alkyl group having 1 to 10 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 12 carbon atoms which may have a substituent, or a 6 carbon number which may have a substituent It is more preferable that it is an aromatic hydrocarbon group of ~18,
More preferably, it is an alkyl group having 1 to 8 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent.
Examples of the substituent include a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, and a halogen atom. Preferably, a halogen atom is more preferable.

R ² , R ⁴ and R ⁵ are each independently,
It is preferably a hydrogen atom, a hydrocarbon group that may have a substituent, or a halogen atom,
Hydrogen atom, alkyl group having 1 to 10 carbon atoms which may have a substituent, cycloalkyl group having 3 to 12 carbon atoms which may have a substituent, carbon which may have a substituent More preferably, it is an aromatic hydrocarbon group of number 6 to 18, or a halogen atom,
More preferably, it is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent.
Examples of the substituent include a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, and a halogen atom. Preferably, a halogen atom is more preferable.

As X ¹ ,
Alkyl group having 1 to 4 carbon atoms, alkenyl group having 2 to 4 carbon atoms, substituted or unsubstituted amino group, N-acylamino group, carboxy group, alkoxy group having 1 to 4 carbon atoms, alkyl group having 1 to 4 carbon atoms It is preferably a sulfanyl group, a cyano group, or a halogen atom,
More preferably, it is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom,
More preferably, it is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, a chlorine atom, or a fluorine atom.

As n, an integer of 0 to 2 is preferable.

The compound (I) is preferably a compound represented by the following formula (Ia).

［式（Ｉａ）中、
Ｒ^1a及びＲ^3aは、それぞれ独立して、置換基を有していてもよい炭素数１～１０のアルキル基、置換基を有していてもよい炭素数３～１２のシクロアルキル基、又は置換基を有していてもよい炭素数６～１８の芳香族炭化水素基を表す。
Ｒ^2a、Ｒ^4a及びＲ^5aは、それぞれ独立して、水素原子、置換基を有していてもよい炭素数１～１０のアルキル基、置換基を有していてもよい炭素数３～１２のシクロアルキル基、又は置換基を有していてもよい炭素数６～１８の芳香族炭化水素基、又はハロゲン原子を表す。
Ｘ²～Ｘ⁵は、それぞれ独立して、水素原子、炭素数１～４のアルキル基、炭素数２～４のアルケニル基、炭素数１～４のアルコキシ基、シアノ基、又はハロゲン原子を表す。Ｘ²とＸ³、Ｘ⁴とＸ⁵は互いに結合して環を形成してもよい。］

[In formula (Ia),
R ^1a and R ^3a are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 12 carbon atoms which may have a substituent, or Represents an aromatic hydrocarbon group having 6 to 18 carbon atoms that may have a substituent.
R ^2a , R ^4a and R ^5a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, and a carbon number 3 to 12 which may have a substituent. represents a cycloalkyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or a halogen atom.
X ² to X ⁵ each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom . X ² and X ³ and X ⁴ and X ⁵ may be bonded to each other to form a ring. ]

R ^1a is preferably an alkyl group having 1 to 8 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent; It is more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and even more preferably a phenyl group which may have a substituent. A phenyl group which may have a substituent is particularly preferred. Examples of the substituent include a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, and a halogen atom. Preferably, a halogen atom is more preferable.

R ^2a may be a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent. Preferably, it is an alkyl group having 1 to 4 carbon atoms which may have a substituent. Examples of the substituent include a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, and a halogen atom. Preferably, a halogen atom is more preferable.

R ^3a is preferably an alkyl group having 1 to 8 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent; More preferably, it is an alkyl group having 1 to 4 carbon atoms which may have a group. Examples of the substituent include a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, and a halogen atom. Preferably, a halogen atom is more preferable.

R ^4a may be a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent. Preferably, it is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and even more preferably a phenyl group which may have a substituent. A phenyl group which may have a substituent at the para position is particularly preferred. Examples of the substituent include a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, and a halogen atom. Preferably, a halogen atom is more preferable.

R ^5a may be a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent. Preferably, it is an alkyl group having 1 to 4 carbon atoms which may have a substituent. Examples of the substituent include a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a carboxy group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, and a halogen atom. Preferably, a halogen atom is more preferable.

X ² to X ⁵ are each independently preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom; , an ethoxy group, a cyano group, a chlorine atom, or a fluorine atom.

The phenylene group to ^which X ² to It is more preferable that it be any of the groups represented by formulas (ph1) to (ph11). Note that * and ** indicate bonds.

Examples of compound (I) include compounds (I-1) to (I-336) shown in Tables 1 to 4.

In Tables 1 to 4, r1 to r2 represent groups represented by the following formulas (r1) to (r2), respectively. Note that * indicates a bond.

In Tables 1 to 4, Me represents a methyl group, Et represents an ethyl group, Pr represents an n-propyl group, and CF ₃ represents a trifluoromethyl group.

In Tables 1 to 4, the column Ph indicates the embodiment of the group represented by the following formula (Ph) in formula (I). In Tables 1 to 4, Ph1 to Ph7 represent groups represented by the following formulas (Ph1) to (Ph7), respectively. Note that * indicates a bond with a nitrogen atom in an atomic group having R ¹ to R ³ , and ** indicates a bond with a nitrogen atom in an atomic group having R ⁴ to R ⁵ .

Compound (I) can be produced, for example, by the method below. First, an amine represented by formula (pt1) is diazotized to produce a diazonium salt represented by formula (q1). A compound represented by formula (q2) is produced by diazo coupling of the obtained diazonium salt represented by formula (q1) and a compound represented by formula (pt2). Subsequently, the compound represented by formula (q2) is diazotized to produce a diazonium salt represented by formula (q3), and then the diazonium salt represented by formula (q3) and the compound represented by formula (pt3) are combined. Compound (I) can be produced by diazo coupling with a compound. The method for obtaining Compound (I), which is the target compound, from the reaction mixture is not particularly limited, and various known methods can be employed. Further, if necessary, it may be further purified by known techniques such as recrystallization. Note that the above-mentioned diazotization and diazo coupling may be carried out by any known method.

In the above formula, R ¹ to R ⁵ , X ¹ and n have the same meanings as above. Q ¹ and Q ² represent arbitrary anions constituting the diazonium salt. The anion may be an inorganic anion or an organic anion. Inorganic anions include fluoride ions, chloride ions, bromide ions, iodide ions, perchlorate ions, hypochlorite ions, etc., and organic anions include CH ₃ COO ^- , C ₆ H ₅ COO ^- etc.

<Colored composition>
The colored composition of the present invention contains compound (I). Compound (I) can be used as a coloring agent (hereinafter sometimes referred to as coloring agent (A)) in a colored composition.
It is preferable that the colored composition of the present invention further contains a resin (hereinafter sometimes referred to as resin (B)).
The coloring composition of the present invention further contains a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)). You can stay there.
The colored composition of the present invention may further contain a solvent (hereinafter sometimes referred to as solvent (E)).
The colored composition of the present invention may further contain a leveling agent (hereinafter, leveling agent (F)).
In this specification, the compounds exemplified as each component can be used alone or in combination, unless otherwise specified.

1. Colorant (A)
Colorant (A) contains compound (I). When the colorant (A) contains the compound (I), it becomes possible to increase the transmittance at 630 nm of the resulting coating film. Moreover, when the colorant (A) contains the compound (I), it is possible to preferably reduce foreign matter between the line patterns after development.

The colorant (A) may contain, in addition to the compound (I), a colorant different from the compound (I). The coloring agent different from compound (I) may be either a pigment (hereinafter sometimes referred to as pigment (A1)) or a dye (hereinafter sometimes referred to as dye (A2)), and compound (I) A different colorant may contain one or both of these pigments (A1) and dyes (A2). When the pigment (A1) is used as the colorant (A), the viscosity of the resulting colored composition may increase; however, the colorant (A) contains the compound (I) together with the pigment (A1). This allows the viscosity of the resulting colored composition to be reduced.
Compound (I), pigment (A1) and dye (A2) will be explained in order below.

1-1. Compound (I)
Compound (I) is a compound represented by the above formula (I), and its preferred embodiments are also the same.

The content of compound (I) is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably is 5% by mass or more, and may be 8% by mass or more. Further, the content of compound (I) may be 100% by mass based on the total amount of colorant (A), but is preferably 80% by mass or less, more preferably 60% by mass or less, still more preferably 40% by mass or less. % by mass or less.

1-2. Pigment (A1)
As the pigment (A1), any known pigment can be used without particular limitation as long as it does not include the compound (I), and for example, it is classified as a pigment in the Color Index (published by The Society of Dyers and Colourists). Examples include pigments.
Examples of pigments include C.I. I. Pigment Yellow 1, 3, 10, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 74, 81, 83, 86, 93, 94, 109, 110, 117, 125, 128, Yellow pigments such as 129, 137, 138, 139, 147, 148, 150, 153, 154, 165, 166, 173, 185, 194, 214, 231, 233;
C. I. Orange pigments such as Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 62, 64, 65, 71, 72, 73;
C. I. Pigment Red 3, 9, 97, 105, 122, 123, 144, 149, 166, 168, 170, 176, 177, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 244, Red pigments such as 254, 255, 264, 265, 266, 268, 269, 273, 291, 295, 296;
C. I. Blue pigments such as Pigment Blue 15, 15:3, 15:4, 15:6, 60;
C. I. Violet color pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;
C. I. Green pigments such as Pigment Green 7, 36, 58, 59, 62, 63;
C. I. Brown pigments such as Pigment Brown 23 and 25;
C. I. Examples include black pigments such as Pigment Black 1 and 7.

The pigment (A1) is preferably an orange pigment or a red pigment, and more preferably a red pigment. When the colorant (A) contains the compound (I) together with an orange pigment or a red pigment, the transmittance of the resulting coating film at 630 nm can be further increased.

According to the chemical structure, the pigment (A1) is preferably an azo pigment other than compound (I), a quinophthalone pigment, a diketopyrrolopyrrole pigment, a phthalocyanine pigment, a squarylium pigment, a perylene pigment, a xanthene pigment, or an isoindoline pigment. , and quinacridone pigments, etc., with azo pigments or diketopyrrolopyrrole pigments being more preferred, and azo pigments being even more preferred. Moreover, as the pigment (A1), it is preferable that it is a red pigment among the above-mentioned pigments.

When the pigment (A1) contains an azo pigment, the azo pigment in the pigment (A1) (preferably a compound represented by the following formula (A1-1), more preferably a compound represented by the following formula (A1-1a)) The content of compound) is preferably 50% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, particularly preferably 100% by mass. .
Further, when the pigment (A1) contains an azo pigment, the azo pigment (preferably a compound represented by the following formula (A1-1), more preferably a compound represented by the following formula (A1-1a)) per 1 part by mass of compound (I) The content of the represented compound) is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, even more preferably 1 part by mass or more, and preferably 30 parts by mass or less, more preferably is 20 parts by mass or less, more preferably 12 parts by mass or less.
By adjusting the content of the azo pigment (preferably a compound represented by the following formula (A1-1), more preferably a compound represented by the following formula (A1-1a)) to the above range, the above transmittance can be achieved. The improvement effect and viscosity reduction effect can be further enhanced.

The azo pigment is a pigment other than compound (I) that has an azo group in its molecule. Note that the "pigment having an azo group in the molecule" also includes a pigment having an azo group due to tautomerism. The azo pigment is preferably a monoazo compound having one azo group in one molecule or a disazo compound having two azo groups in one molecule, and more preferably a disazo compound.
More specifically, as the azo pigment, C.I. I. Pigment Red 269 and a compound represented by the following formula (A1-1), preferably at least one selected from the group consisting of C. I. More preferably, it is at least one selected from the group consisting of Pigment Red 269 and a compound represented by the following formula (A1-1a).

Specifically, as the monoazo compound, C. I. Pigment Yellow 3, 74, 165 and other yellow pigments; C.I. I. Pigment Red 3, 170, 269, and other red pigments; among them, C. I. Pigment Red 269 is preferred.

As the disazo compound, a compound represented by formula (A1-1) is preferred.

［式（Ａ１－１）中、
Ｌ²は、置換基を有していてもよいフェニレン基又はビフェニレン基であり、
Ａ及びＢは、それぞれ独立して、式（ｔ１）～式（ｔ５）で表される基のいずれかである。］

［式（ｔ１）～式（ｔ５）中、Ｒ¹¹～Ｒ²⁶はそれぞれ独立して、水素原子、置換基を有していてもよい炭化水素基、複素環基、シアノ基、又はハロゲン原子を表す。＊はＬ²との結合手を表す。］

[In formula (A1-1),
L ² is a phenylene group or biphenylene group which may have a substituent,
A and B are each independently any of the groups represented by formulas (t1) to (t5). ]

[In formulas (t1) to (t5), R ¹¹ to R ²⁶ each independently represent a hydrogen atom, a hydrocarbon group that may have a substituent, a heterocyclic group, a cyano group, or a halogen atom. represent. * represents a bond with L ² . ]

In formula (A1-1), L ² is a phenylene group or a biphenylene group which may have a substituent, and is preferably a phenylene group which may have a substituent.

The substituent that the phenylene group and biphenylene group in L ² may have (hereinafter sometimes referred to as substituent C) includes an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted amino group, an N- Examples include an acylamino group, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, a cyano group, and a halogen atom.

The alkyl group having 1 to 4 carbon atoms in substituent C is preferably a methyl group or an ethyl group, more preferably a methyl group.

Substituted or unsubstituted amino group, N-acylamino group, alkoxy group having 1 to 4 carbon atoms, alkylsulfanyl group having 1 to 4 carbon atoms, and halogen atom as substituent A are substituted or unsubstituted in substituent A. Examples include those explained as substituted amino groups, N-acylamino groups, alkoxy groups having 1 to 4 carbon atoms, alkylsulfanyl groups having 1 to 4 carbon atoms, and halogen atoms, and their preferred ranges are also the same.

The substituent C is preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom, such as a methyl group, ethyl group, methoxy group, ethoxy group, cyano group, or chlorine atom. , or a fluorine atom is more preferable.

The number of substituents C is preferably 1 to 4, more preferably 1 or 2. When having a plurality of substituents C, the plurality of substituents C may be the same or different, but are preferably the same.

The positions of the two bonds in the phenylene group and the biphenylene group are not particularly limited, but from the viewpoint of availability of raw materials, the positions of the two bonds in the phenylene group and the 4,4' positions in the case of the phenylene group and the 4,4' positions in the case of the biphenylene group are Preferably, it has a bond.

L ² is preferably any of the groups represented by formulas (ph3-1) to (ph3-12), more preferably groups represented by formulas (ph3-1) to (ph3-8). and more preferably any of the groups represented by formulas (ph3-1) to (ph3-7). In the formula, * represents a bond.

In formula (A1-1), A and B are each independently any of the groups represented by formula (t1) to formula (t5), and are represented by formula (t1) to formula (t4). It is more preferable that it is any of the groups represented by formula (t1) to formula (t3), and it is particularly preferable that it is any of the groups represented by formula (t1). preferable. A and B may be the same or different, but are preferably the same.

Examples of the hydrocarbon groups represented by R ¹¹ to R ²⁶ include the groups described above as the hydrocarbon groups represented by R ¹ to R ⁵ and X ¹ . Among these, preferred are alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and aromatic hydrocarbon groups having 6 to 12 carbon atoms; More preferred are cycloalkyl groups and aromatic hydrocarbon groups having 6 to 10 carbon atoms.

Examples of the substituents that the hydrocarbon groups represented by R ¹¹ to R ²⁶ may have include the same groups as substituent A, and preferred embodiments are also the same.

Examples of the heterocyclic group represented by R ¹¹ to R ²⁶ include the groups described above as the heterocyclic group represented by R ¹ to R ⁵ , and preferred embodiments thereof are also the same.

Examples of the halogen atoms represented by R ¹¹ to R ²⁶ include those explained as the halogen atoms for substituent A and substituent B, and among them, chlorine atom and fluorine atom are preferred.

R ¹¹ is preferably an aromatic hydrocarbon group that may have a substituent, more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms that may have a substituent, and even more preferably is a phenyl group which may have a substituent.

R ¹² is preferably an alkyl group that may have a substituent, more preferably an alkyl group that may have a halogen atom, and even more preferably an alkyl group that may have a halogen atom. 1 to 4 alkyl groups.

R ¹³ and R ¹⁴ are each independently preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aromatic hydrocarbon group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a carbon It is a cycloalkyl group of number 3 to 8 or a phenyl group. Preferably, R ¹³ and R ¹⁴ are the same.

R ¹⁵ is preferably an alkyl group which may have a substituent or a hydrogen atom, more preferably an alkyl group, still more preferably an alkyl group having 1 to 4 carbon atoms.

R ¹⁶ is preferably an alkyl group or a cyano group that may have a substituent, more preferably an alkyl group or a cyano group that may have a halogen atom, and even more preferably an alkyl group or a cyano group that may have a halogen atom. It is an alkyl group or a cyano group having 1 to 4 carbon atoms, which may have 1 to 4 carbon atoms.

R ¹⁷ is preferably an alkyl group that may have a substituent, more preferably an alkyl group that may have a halogen atom, and even more preferably an alkyl group that may have a halogen atom. 1 to 4 alkyl groups.

R ¹⁸ is preferably an alkyl group which may have a substituent, more preferably an alkyl group having 1 to 4 carbon atoms.

R ¹⁹ is preferably an alkyl group which may have a substituent or a hydrogen atom, more preferably an alkyl group having 1 to 4 carbon atoms or a hydrogen atom.

R ²⁰ is preferably an aromatic hydrocarbon group or a heterocyclic group which may have a substituent, more preferably a phenyl group or a benzene ring-containing heterocyclic group which may have a substituent. and more preferably a phenyl group or a benzimidazolonyl group which may have a halogen atom.

R ²¹ to R ²⁶ are each independently preferably an alkyl group or a hydrogen atom that may have a substituent, more preferably an alkyl group or a hydrogen atom that may have a halogen atom, More preferably, it is an alkyl group having 1 to 4 carbon atoms, which may have a halogen atom, or a hydrogen atom.

As the disazo compound, a compound represented by formula (A1-1a) is more preferable.

［式（Ａ１－１ａ）中、
Ｒ^1a～Ｒ^4aは、それぞれ独立して、水素原子、置換基を有していてもよい炭素数１～１０のアルキル基、置換基を有していてもよい炭素数３～１０のシクロアルキル基、又は置換基を有していてもよい炭素数６～１２の芳香族炭化水素基を表す。
Ｌ^2aは、炭素数１～４のアルキル基、炭素数１～４のアルコキシ基、ハロゲン原子、及びシアノ基からなる群から選択される少なくとも１種の置換基を有していてもよいフェニレン基又はビフェニレン基を表す。］

[In formula (A1-1a),
R ^1a to R ^4a each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, and an optionally substituted cycloalkyl group having 3 to 10 carbon atoms; group, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent.
L ^2a is a phenylene group optionally having at least one substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, and a cyano group; Or represents a biphenylene group. ]

Examples of the alkyl group, cycloalkyl group, and aromatic hydrocarbon group represented by R ^1a to R ^4a include the alkyl group, cycloalkyl group, and aromatic hydrocarbon group represented by R ¹ to R ⁵ and X ¹ described above. Examples include the groups explained as . Further, as the substituent that the alkyl group, cycloalkyl group, and aromatic hydrocarbon group represented by R ^1a to R ^4a may have, the same groups as substituent A can be mentioned, and the preferred embodiments are also the same. It is.

R ^1a is preferably an aromatic hydrocarbon group that may have a substituent, more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms that may have a substituent, and Preferred is a phenyl group which may have a substituent.
R ^2a is preferably an alkyl group that may have a substituent, more preferably an alkyl group that may have a halogen atom, and even more preferably a carbon group that may have a halogen atom. It is an alkyl group of numbers 1 to 4.
R ^3a is preferably an aromatic hydrocarbon group that may have a substituent, more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms that may have a substituent, and Preferred is a phenyl group which may have a substituent.
R ^4a is preferably an alkyl group that may have a substituent, more preferably an alkyl group that may have a halogen atom, and even more preferably a carbon group that may have a halogen atom. It is an alkyl group of numbers 1 to 4.
R ^1a and R ^3a may be the same or different, but are preferably the same, and R ^2a and R ^4a may be the same or different, but are preferably the same.

L ^2a may have at least one substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, and a cyano group. , 4-phenylene group or 4,4'-biphenylene group, selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, and a cyano group. More preferred is a 1,4-phenylene group which may have at least one substituent. Specifically, it is preferably any of the groups represented by the above formulas (ph3-1) to (ph3-12), and the groups represented by the above formulas (ph3-1) to (ph3-8). It is more preferable to be any of the groups represented by the formulas (ph3-1) to (ph3-7) described above.

Examples of the compound represented by formula (A1-1a) include the following No. 1 in formula (A1-1a). Examples include compounds having groups represented by 1 to 55.

In Table 5, r-1 and r-2 represent groups represented by the following formulas (r-1) and (r-2), respectively. Note that * indicates a bond.

In Table 5, Me represents a methyl group, and CF ₃ represents a trifluoromethyl group.

In Table 5, l-1 to l-8 represent groups represented by the following formulas (1-1) to (1-8), respectively. Note that * indicates a bond with a nitrogen atom in an atomic group having R ^1a and R ^2a , and ** indicates a bond with a nitrogen atom in an atomic group having R ^3a and R ^4a .

The quinophthalone pigment is a pigment having a quinophthalone structure in its molecule, and specifically, C.I. I. Pigment Yellow 138, 231, 233 and the like.

The diketopyrrolopyrrole pigment is a pigment having a diketopyrrolopyrrole structure in its molecule, and is preferably a compound represented by formula (A1-3).

［式（Ａ１－３）中、
Ｘ³¹及びＸ³²はそれぞれ独立して、置換基を有していてもよい炭化水素基、ハロゲン原子、又はシアノ基を表し、
ｎ３１及びｎ３２はそれぞれ独立して、０～５の整数を表し、ｎ３１が２以上の整数を表す場合、複数のＸ³¹は同一であっても異なっていてもよく、ｎ３２が２以上の整数を表す場合、複数のＸ³²は同一であっても異なっていてもよい。］

[In formula (A1-3),
X ³¹ and X ³² each independently represent a hydrocarbon group, a halogen atom, or a cyano group that may have a substituent,
n31 and n32 each independently represent an integer from 0 to 5; when n31 represents an integer of 2 or more, multiple X ^31s may be the same or different; When expressed, multiple X ^32s may be the same or different. ]

The hydrocarbon group which may have a substituent represented by X ³¹ and X ³² is explained as a hydrocarbon group which may have a substituent represented by R ¹ to R ⁵ and X ¹ Examples include groups similar to the above groups. X ^{31 and} It is preferably a hydrogen group, more preferably an alkyl group having 1 to 4 carbon atoms which may have a substituent, or a phenyl group which may have a substituent, and which has a halogen atom. It is more preferably an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, or a phenyl group which may have a halogen atom, and particularly preferably a trifluoromethyl group or a phenyl group.

Examples of the halogen atom represented by X ³¹ and X ³² include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

It is preferable that X ³¹ and X ³² are the same group.

It is preferable that n31 and n32 are each independently an integer of 1 to 3, and more preferably 1. In particular, when n31 and n32 are 1, the substitution positions of X ³¹ and X ³² are preferably para-position or meta-position, and X ³¹ and X ³² are optionally substituted hydrocarbon groups or When it is a halogen atom, it is more preferable that it is bonded to the para position, and when X ³¹ and X ³² are cyano groups, it is more preferable that it is bonded to the meta position.

Examples of diketopyrrolopyrrole pigments include C.I. I. Pigment Red 254, 255, 264, 272, 291, C. I. Pigment Orange 71, 73, and the like.

The phthalocyanine pigment is a pigment having a phthalocyanine structure in its molecule, and specifically, C.I. I. Pigment Green 7, 36, 58, 59, C. I. Pigment Blue 15, 15:3, 15:4, 15:6 and the like.

The squarylium pigment is a pigment having a squarylium structure in its molecule, and is preferably a compound represented by formula (A1-5).

［式（Ａ１－５）中、
Ｒ⁵¹～Ｒ⁵⁴はそれぞれ独立して、水素原子又はヒドロキシ基を表し、
Ｒ⁵⁵～Ｒ⁵⁸はそれぞれ独立して、置換基を有していてもよい炭化水素基を表し、該炭化水素基に含まれる－ＣＨ₂－は、－Ｏ－、－ＣＯ－又は－ＮＨ－に置き換わっていてもよい。］

[In formula (A1-5),
R ⁵¹ to R ⁵⁴ each independently represent a hydrogen atom or a hydroxy group,
R ⁵⁵ to R ⁵⁸ each independently represent a hydrocarbon group which may have a substituent, and -CH ₂ - contained in the hydrocarbon group is -O-, -CO- or -NH- may be replaced by ]

It is preferable that R ⁵¹ to R ⁵⁴ are all hydroxy groups, or R ⁵¹ and R ⁵⁴ are hydroxy groups, and R ⁵² and R ⁵³ are hydrogen atoms.

The hydrocarbon group which may have a substituent represented by R ⁵⁵ to R ⁵⁸ is explained as a hydrocarbon group which may have a substituent represented by R ¹ to R ⁵ and X ¹ Examples include groups similar to the above groups. R ⁵⁵ to R ⁵⁸ are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, or a carbonized aromatic group having 6 to 12 carbon atoms which may have a substituent. It is preferably a hydrogen group, more preferably an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, such as a methyl group, ethyl group, o-tolyl group, m-tolyl group. or p-tolyl group is more preferable. In particular, R ⁵⁵ to R ⁵⁸ are alkyl groups having 1 to 4 carbon atoms, or R ⁵⁵ and R ⁵⁸ are aromatic hydrocarbon groups having 6 to 10 carbon atoms, and R ⁵⁶ and R ⁵⁷ are carbon atoms Preferably, it is an alkyl group having 1 to 4 atoms.

The perylene pigment is a pigment having a perylene structure in its molecule, and specifically, C.I. I. Pigment Red 179, 190, 224 and the like.

The xanthene pigment is a pigment having a xanthene structure in its molecule, and is preferably a compound represented by formula (A1-7).

［式（Ａ１－７）中、Ｒ⁷¹～Ｒ⁷⁴はそれぞれ独立して、水素原子または置換基を有していてもよい炭化水素基を表し、該炭化水素基に含まれる－ＣＨ₂－は、－Ｏ－、－ＣＯ－又は－ＮＨ－に置き換わっていてもよい。］

[In formula (A1-7), R ⁷¹ to R ⁷⁴ each independently represent a hydrogen atom or a hydrocarbon group which may have a substituent, and -CH ₂ - contained in the hydrocarbon group is , -O-, -CO- or -NH-. ]

The hydrocarbon group which may have a substituent represented by R ⁷¹ to R ⁷⁴ is explained as a hydrocarbon group which may have a substituent represented by R ¹ to R ⁵ and X ¹ Examples include groups similar to the above groups. R ⁷¹ to R ⁷⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or a C 6 to 12 alkyl group which may have a substituent. It is preferably an aromatic hydrocarbon group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, such as a hydrogen atom, a methyl group, or an ethyl group. , o-tolyl group, 2,4-dimethylphenyl group, 2,6-dimethylphenyl group, or 2,4,6-trimethylphenyl group. In particular, it is preferable that R ⁷¹ and R ⁷⁴ are aromatic hydrocarbon groups having 6 to 10 carbon atoms, and that R ⁷² and R ⁷³ are hydrogen atoms.

The isoindoline pigment is a pigment having an isoindoline skeleton in its molecule, and specifically, C.I. I. Pigment Yellow 110, 139, 185 and the like.

The quinacridone pigment is a pigment having a quinacridone structure in its molecule, and is preferably a compound represented by formula (A1-8).

［式（Ａ１－８）中、
Ｒ⁸¹及びＲ⁸²はそれぞれ独立して、水素原子または置換基を有していてもよい炭化水素基を表し、該炭化水素基に含まれる－ＣＨ₂－は、－Ｏ－、－ＣＯ－又は－ＮＨ－に置き換わっていてもよい。
Ｘ⁸¹～Ｘ⁸⁸はそれぞれ独立して、水素原子、ハロゲン原子、または置換基を有していてもよい炭化水素基を表し、該炭化水素基に含まれる－ＣＨ₂－は、－Ｏ－、－ＣＯ－又は－ＮＨ－に置き換わっていてもよい。］

[In formula (A1-8),
R ⁸¹ and R ⁸² each independently represent a hydrogen atom or a hydrocarbon group which may have a substituent, and -CH ₂ - contained in the hydrocarbon group is -O-, -CO- or -NH- may be substituted.
X ⁸¹ to X ⁸⁸ each independently represent a hydrogen atom, a halogen atom, or a hydrocarbon group which may have a substituent, and -CH ₂ - contained in the hydrocarbon group represents -O-, It may be replaced with -CO- or -NH-. ]

Hydrocarbon groups which may have substituents represented by R ⁸¹ to R ⁸² and X ⁸¹ to X ⁸⁸ include those which may have substituents represented by R ¹ to R ⁵ and X ¹ . Examples of good hydrocarbon groups include groups similar to those described above.
Examples of the halogen atom represented by X ⁸¹ to X ⁸⁸ include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like, with a chlorine atom being preferred.

R ⁸¹ and R ⁸² are each independently preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent; More preferably, it is an alkyl group having 1 to 4 carbon atoms.

X ⁸¹ to X ⁸⁸ are each independently preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms which may have a substituent; More preferably, it is an alkyl group having 1 to 4 carbon atoms which may have a substituent. In ^particular , an embodiment in ^which all of X ⁸¹ to X ⁸⁸ are hydrogen atoms; ^{X 82 and} ~An embodiment in which X ⁸⁵ , X ⁸⁷ and X ⁸⁸ are hydrogen atoms; X ⁸³ and X ⁸⁷ are a halogen atom or an alkyl group having 1 to 4 carbon atoms which may have ^a substituent, ^and , ^an embodiment in ^which X ⁸⁴ to X ⁸⁶ and X ⁸⁸ are hydrogen atoms; or an embodiment in which ^{X 81 ,} The preferred embodiment is that X ⁸² , X ⁸⁴ , X ⁸⁶ , and X ⁸⁸ are hydrogen atoms.

The content of the pigment (A1) is preferably 20% by mass or more, more preferably 40% by mass or more, even more preferably 60% by mass or more, and 99% by mass or less, based on the total amount of the colorant (A). The content is preferably 97% by mass or less, and even more preferably 95% by mass or less.

The content of pigment (A1) per 1 part by mass of compound (I) is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, still more preferably 1 part by mass or more, and 30 parts by mass or more. It is preferably at most parts by mass, more preferably at most 20 parts by mass, even more preferably at most 12 parts by mass.

The total amount of compound (I) and pigment (A1) is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, based on the total amount of colorant (A). , particularly preferably 98% by mass or more, and may be 100% by mass.

Compound (I) and pigment (A1) can be treated, if necessary, by rosin treatment, surface treatment using a pigment derivative into which an acidic group or basic group has been introduced, grafting treatment on the pigment surface with a polymer compound, etc. Atomization treatment using a sulfuric acid atomization method or the like, a cleaning treatment using an organic solvent, water, etc. to remove impurities, or a removal treatment using an ion exchange method or the like for ionic impurities may be performed.
Compound (I) and pigment (A1) preferably have uniform particle sizes. By containing a pigment dispersant and performing a dispersion treatment, a colored composition in which compound (I) and pigment (A1) are uniformly dispersed in the solution can be obtained. In addition, when using the compound (I) and the pigment (A1) as a colorant, the colored composition is prepared by dispersing the compound (I) and the pigment (A1) and then mixing the treated products obtained. Alternatively, a colorant containing compound (I) and pigment (A1) may be subjected to a dispersion treatment.

Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Pigment dispersants include trade names such as KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by CIBA), and Ajisper (manufactured by Ajinomoto Fine Co., Ltd.). (manufactured by Techno Co., Ltd.), Disperbyk (manufactured by BYK), BYK LPN (manufactured by BYK), and the like.
When using a pigment dispersant, the amount used is preferably 1% by mass or more and 100% by mass or less, more preferably 5% by mass or more and 80% by mass, based on the total amount of compound (I) and pigment (A1). % or less. When the amount of the pigment dispersant used is within the above range, a uniformly dispersed colored composition tends to be obtained.

1-3. Dye (A2)
The dye (A2) is not particularly limited and any known dye can be used, such as solvent dyes, acid dyes, direct dyes, mordant dyes, and the like. Examples of dyes include compounds that are classified as having hues other than pigments in the Color Index (published by The Society of Dyers and Colourists), and known dyes listed in Dyeing Notes (Shirosensha). It will be done. Furthermore, according to the chemical structure, azo dyes other than compound (I), cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine Examples include dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Among these, organic solvent soluble dyes are preferred.

Specifically, C. I. Solvent Yellow 4 (hereinafter, the description of C.I. Solvent Yellow will be omitted and only the numbers will be described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99 , 117, 162, 163, 167, 189;
C. I. Solvent red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;
C. I. Solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. C.I. such as Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. I. solvent dye,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;
C. I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;
C. I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;
C. I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, C. 104, 105, 106, 109, etc. I. acid dye,
C. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141;
C. I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C. I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;
C. I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, etc. I. direct dye,
C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse Violet 26, 27;
C. I. C.I. such as Disperse Blue 1, 14, 56, 60, etc. I. disperse dye,
C. I. Basic Red 1, 10;
C. I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;
C. I. Basic Violet 2;
C. I. Basic Red 9;
C. I. C. such as Basic Green 1; I. basic dye,
C. I. Reactive Yellow 2,76,116;
C. I. Reactive Orange 16;
C. I. C. such as Reactive Red 36; I. reactive dye,
C. I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modern tread 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38 , 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;
C. I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C. I. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;
C. I. Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43 , 44, 48, 49, 53, 61, 74, 77, 83, 84;
C. I. C. mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. I. mordant dye,
C. I. Bat green 1st class C. I. Examples include vat dye.

The content of the dye (A2) is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 2% by mass or less, particularly preferably 1% by mass or less, based on the total amount of the colorant (A). It is less than or equal to 0% by mass, and may be 0% by mass.

The content of the colorant (A) is preferably 0.1% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 60% by mass or less, and even more preferably It is 8% by mass or more and 50% by mass or less. When the content of the colorant (A) is within the above range, the color density when used as a color filter is sufficient, and the composition contains the necessary amount of the resin (B) and the polymerizable compound (C). Therefore, a pattern with sufficient mechanical strength can be formed.

Here, the "total amount of solid content" in this specification refers to the amount obtained by subtracting the solvent content from the total amount of the coloring composition. The total amount of solid content and the content of each component relative to the total amount can be measured by known analytical means such as liquid chromatography or gas chromatography.

2. Resin (B)
Preferably, the resin (B) is an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6].
Resin [K1]; a structural unit derived from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides; , a copolymer having a structural unit derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond;
Resin [K2]: Structural units derived from (a), structural units derived from (b), and monomer (c) copolymerizable with (a) (however, (a) and (b) are ) (hereinafter sometimes referred to as "(c)");
Resin [K3]; copolymer having a structural unit derived from (a) and a structural unit derived from (c);
Resin [K4]; a copolymer having a structural unit in which (b) is added to a structural unit derived from (a) and a structural unit derived from (c);
Resin [K5]; a copolymer having a structural unit in which (a) is added to a structural unit derived from (b) and a structural unit derived from (c);
Resin [K6]: A copolymer having a structural unit derived from (b) with (a) added thereto and a carboxylic acid anhydride further added thereto, and a structural unit derived from (c).

As (a), specifically, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[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] Bicyclounsaturated compounds containing a carboxyl group such as hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;
Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Unsaturated dicarboxylic acid anhydrides such as tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;
Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyhydric carboxylic acids such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate. Class;
Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid.
Among these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferred from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in an aqueous alkali solution.

In addition, in this specification, "(meth)acrylic acid" represents at least one type selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth)acryloyl" and "(meth)acrylate" have similar meanings.

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

Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond, Monomer (b2) (hereinafter sometimes referred to as "(b2)"), monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), etc. Can be mentioned.

As (b1), for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as "(b1-1)") monomer (b1-2) (hereinafter sometimes referred to as "(b1-2)") has a structure in which an alicyclic unsaturated hydrocarbon is epoxidized.

(b1-1) includes glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, -Vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis(glycidyloxymethyl)styrene , 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene , 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris Examples include (glycidyloxymethyl)styrene.

Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (R1) and formula (R2) Examples include compounds represented by:

[In formula (R1) and formula (R2), R ^ra and R ^rb represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with a hydroxy group. It's okay.
X ^ra and X ^rb represent a single bond, *-R ^rc -, *-R ^rc -O-, *-R ^rc -S- or *-R ^rc -NH-.
R ^rc represents an alkanediyl group having 1 to 6 carbon atoms.
* represents a bond with O. ]

Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group.
Examples of alkyl groups in which hydrogen atoms are substituted with hydroxy 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, 4-hydroxybutyl group and the like.
Preferred examples of R ^ra and R ^rb include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferably a hydrogen atom and a methyl group.

Examples of alkanediyl groups include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, and hexane-1,5-diyl group. Examples include 1,6-diyl group.
X ^ra and X ^rb are preferably a single bond, a methylene group, an ethylene group, *-CH ₂ -O- and *-CH ₂ CH ₂ -O-, and more preferably a single bond, *-CH ₂ Examples include CH ₂ -O- (* represents a bond with O).

Examples of the compound represented by formula (R1) include compounds represented by any of formulas (R1-1) to (R1-15). Among them, formula (R1-1), formula (R1-3), formula (R1-5), formula (R1-7), formula (R1-9) or formula (R1-11) to formula (R1-15) Compounds represented by formula (R1-1), formula (R1-7), formula (R1-9) or formula (R1-15) are more preferred.

Examples of the compound represented by formula (R2) include compounds represented by any of formulas (R2-1) to (R2-15). Among them, formula (R2-1), formula (R2-3), formula (R2-5), formula (R2-7), formula (R2-9) or formula (R2-11) to formula (R2-15) Compounds represented by formula (R2-1), formula (R2-7), formula (R2-9) or formula (R2-15) are more preferred.

The compound represented by formula (R1) and the compound represented by formula (R2) may be used alone or in combination of two or more. When the compound represented by formula (R1) and the compound represented by formula (R2) are used together, their content ratio [compound represented by formula (R1): compound represented by formula (R2)] is On a molar basis, the ratio is preferably 5:95 to 95:5, more preferably 20:80 to 80:20.

As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. As (b2), 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane , 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like.

As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V #150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

As for (b), (b1) is preferable in that the reliability of heat resistance, chemical resistance, etc. of the color filter obtained can be made higher. Furthermore, (b1-2) is more preferred in that the coloring composition has excellent storage stability.

Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate. Acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ] Decan-8-yl (meth)acrylate (commonly referred to as "dicyclopentanyl (meth)acrylate" in the technical field. Also, when referred to as "tricyclodecyl (meth)acrylate") ), tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate (commonly referred to as "dicyclopentenyl (meth)acrylate" in the technical field). ), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylic acid esters such as (meth)acrylate;
Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconate;
Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5- Hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1] Hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[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-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy -5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2 .2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyl) Bicyclounsaturated compounds such as (oxycarbonyl)bicyclo[2.2.1]hept-2-ene;
N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 - Dicarbonylimide derivatives such as maleimidopropionate and N-(9-acridinyl)maleimide;
Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene , isoprene, 2,3-dimethyl-1,3-butadiene, and the like.
Among these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, 2 -Hydroxyethyl (meth)acrylate and the like are preferred.

In resin [K1], the ratio of structural units derived from each is as follows among all structural units constituting resin [K1]:
Structural unit derived from (a); 2 to 60 mol%
Structural unit derived from (b); 40 to 98 mol%
It is preferable that
Structural unit derived from (a); 10 to 50 mol%
Structural unit derived from (b); 50 to 90 mol%
It is more preferable that
When the ratio of the structural units of the resin [K1] is within the above range, the storage stability of the colored composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent. .

Resin [K1] can be used, for example, by the method described in the document "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published on March 1, 1972) and the literature. It can be manufactured by referring to the cited literature described in .

Specifically, predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, and a deoxidized atmosphere is created by replacing oxygen with nitrogen, for example, and while stirring, Examples include methods of heating and keeping warm. Note that the polymerization initiator, solvent, etc. used here are not particularly limited, and those commonly used in the field can be used. For example, as a polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) Examples of the solvent include those that can dissolve each monomer, and examples of the solvent (E) of the colored composition of the present invention include the solvents described below.

The obtained copolymer may be used as it is as a solution after the reaction, or may be used as a concentrated or diluted solution, or may be taken out as a solid (powder) by a method such as reprecipitation. You may use something. In particular, by using the solvent contained in the colored composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for preparing the colored composition of the present invention. The manufacturing process of the colored composition can be simplified.

In resin [K2], the ratio of structural units derived from each is as follows among all structural units constituting resin [K2]:
Structural unit derived from (a); 2 to 45 mol%
Structural unit derived from (b); 2 to 95 mol%
Structural unit derived from (c); 1 to 75 mol%
It is preferable that
Structural unit derived from (a); 5 to 40 mol%
Structural unit derived from (b); 5 to 80 mol%
Structural unit derived from (c); 5 to 70 mol%
It is more preferable that
When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and Tends to have excellent mechanical strength.

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

In resin [K3], the ratio of structural units derived from each is as follows among all structural units constituting resin [K3]:
Structural unit derived from (a); 2 to 60 mol%
Structural unit derived from (c); 40 to 98 mol%
It is preferable that
Structural unit derived from (a); 10 to 50 mol%
Structural unit derived from (c); 50 to 90 mol%
It is more preferable that
Resin [K3] can be produced, for example, in the same manner as the method described as the production method for resin [K1].

Resin [K4] is obtained by obtaining a copolymer of (a) and (c), and a carboxylic acid and/or carboxylic acid anhydride in which (a) has a cyclic ether having 2 to 4 carbon atoms in (b). It can be manufactured by adding it to.
First, a copolymer of (a) and (c) is produced in the same manner as described as the method for producing resin [K1]. In this case, the ratio of structural units derived from each is preferably the same as that listed for resin [K3].

Next, a portion of the carboxylic acid and/or carboxylic acid anhydride derived from (a) in the copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms contained in (b).
Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b) a reaction catalyst between a carboxylic acid or carboxylic acid anhydride and a cyclic ether (for example, Tris ( Resin [K4] can be produced by putting dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (e.g., hydroquinone, etc.) into a flask and reacting at 60 to 130°C for 1 to 10 hours. can.
The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). By keeping it in this range, the storage stability of the coloring composition, the developability when forming a pattern, and the resulting pattern tend to have a good balance among solvent resistance, heat resistance, mechanical strength, and sensitivity. . Since the cyclic ether has high reactivity and unreacted (b) is unlikely to remain, (b1) is preferable as (b) used in resin [K4], and (b1-1) is more preferable.
The amount of the reaction catalyst used is preferably 0.001 to 5 parts by weight based on 100 parts by weight of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by weight based on 100 parts by weight of the total amount of (a), (b) and (c).
Reaction conditions such as the charging method, reaction temperature and time can be adjusted as appropriate in consideration of manufacturing equipment, the amount of heat generated by polymerization, and the like. Note that, similarly to the polymerization conditions, the charging method and reaction temperature can be adjusted as appropriate, taking into account the manufacturing equipment, the amount of heat generated by polymerization, and the like.

As a first step, resin [K5] is obtained as a copolymer of (b) and (c) in the same manner as the method for producing resin [K1] described above. Similarly to the above, the obtained copolymer may be used as it is as a solution after the reaction, a concentrated or diluted solution may be used, or it may be converted into a solid (powder) by a method such as reprecipitation. You may use the one taken out.
The ratio of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the above copolymer is, respectively,
Structural unit derived from (b); 5 to 95 mol%
Structural unit derived from (c); 5 to 95 mol%
It is preferable that
Structural unit derived from (b); 10 to 90 mol%
Structural unit derived from (c); 10 to 90 mol%
It is more preferable that

Furthermore, under the same conditions as in the manufacturing method of resin [K4], the cyclic ether derived from (b) contained in the copolymer of (b) and (c) is added to the carboxylic acid or carboxylic acid anhydride contained in (a). Resin [K5] can be obtained by reacting the substances.
The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Since the reactivity of the cyclic ether is high and unreacted (b) is unlikely to remain, (b) used in resin [K5] is preferably (b1), and more preferably (b1-1).

Resin [K6] is a resin obtained by reacting resin [K5] with a carboxylic acid anhydride. A carboxylic acid anhydride is reacted with a hydroxy group generated by the reaction of a cyclic ether and a carboxylic acid or a carboxylic acid anhydride.
Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 , 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, and the like. The amount of carboxylic acid anhydride used is preferably 0.5 to 1 mol per 1 mol of (a).

Specifically, the resin (B) includes 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] Resin such as decyl acrylate/(meth)acrylic acid copolymer [K1]; glycidyl(meth)acrylate/benzyl(meth)acrylate/(meth)acrylic acid copolymer, glycidyl(meth)acrylate/styrene/(meth) ) Acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] Decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl(meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxy Resins such as methyl oxetane/(meth)acrylic acid/styrene copolymers [K2]; Resins such as benzyl (meth)acrylate/(meth)acrylic acid copolymers, styrene/(meth)acrylic acid copolymers [K3] ]; Resin in which glycidyl (meth)acrylate is added to benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate added to tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymer. ) Resins to which acrylate has been added, resins such as resins to which glycidyl (meth)acrylate has been added to tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer [K4]; Tricyclo A resin made by reacting a copolymer of decyl (meth)acrylate/glycidyl (meth)acrylate with (meth)acrylic acid, a copolymer of tricyclodecyl (meth)acrylate/styrene/glycidyl (meth)acrylate (meth) Resin [K5], such as a resin made by reacting acrylic acid; A resin made by reacting a copolymer of tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate with (meth)acrylic acid, and further adding tetrahydrophthalic anhydride. Examples include resin [K6] such as a reacted resin.
Among these, as the resin (B), resin [K1] and/or resin [K2] are preferable, and resin [K1] is particularly preferable.

The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 or more and 100,000 or less, more preferably 5,000 or more and 50,000 or less, and still more preferably 5,000 or more and 30,000 or less. It is as follows. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed area in the developer is good, and the resolution of the colored pattern tends to be improved.

The dispersity [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 or more and 6 or less, more preferably 1.2 or more and 4 or less.

The acid value of the resin (B) is preferably 50 mg-KOH/g or more and 170 mg-KOH/g or less, more preferably 60 mg-KOH/g or more and 150 mg-KOH/g or less, and even more preferably It is 70 mg-KOH/g or more and 135 mg-KOH/g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution. .

The content of the resin (B) is preferably 7% by mass or more and 85% by mass or less, more preferably 13% by mass or more and 80% by mass or less, and even more preferably 20% by mass, based on the total solid content. The content is 70% by mass or less. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to improve.

3. Polymerizable compound (C)
The polymerizable compound (C) is a compound that can be polymerized by active radicals and/or acids generated from the polymerization initiator (D), and includes, for example, a compound having a polymerizable ethylenically unsaturated bond. is a (meth)acrylic acid ester compound.

Among these, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol 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, Examples include caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, and the like.
Among these, at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate is preferred.

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

The content of the polymerizable compound (C) is preferably 5% by mass or more and 75% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably It is 15% by mass or more and 50% by mass or less. When the content of the polymerizable compound (C) is within the above range, the residual film rate during colored pattern formation and the chemical resistance of the color filter tend to improve.

4. Polymerization initiator (D)
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids, etc. under the action of light or heat, and any known polymerization initiator can be used. Examples of the polymerization initiator that generates active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

The O-acyloxime compound is a compound having a partial structure represented by formula (d1). Hereinafter, * represents a bond.

Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane -1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6- (2-Methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2, 4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole -3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane- Examples include 1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and the like. Commercial products such as Irgacure OXE01, OXE02 (manufactured by BASF), N-1919 (manufactured by ADEKA), and TR-PBG-327 (manufactured by Changzhou Strong Electronics New Materials Co., Ltd.) may be used. Among them, O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1 -one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)- 3-cyclopentylpropan-1-one-2-imine is preferred, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetyloxy-1-(4-phenyl More preferred is sulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine. These O-acyloxime compounds tend to provide color filters with high brightness.

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

Examples of compounds having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4 -morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one etc. Commercial products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may be used.
Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2 -Hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenylketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxy Examples include acetophenone and benzyl dimethyl ketal.
From the viewpoint of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

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-methoxy) styryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4 -bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-) 2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, etc. can be mentioned.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)- 4,4',5,5'-tetraphenylbiimidazole (for example, see JP-A-6-75372, JP-A-6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4 , 4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis (2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(tri- alkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Laid-open No. 62-174204, etc.), in which the phenyl group at the 4,4'5,5'-position is substituted with a carbalkoxy group. Examples include imidazole compounds (see, for example, JP-A-7-10913).

Furthermore, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Examples include quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiation aid (D1) (especially amines) described below.

Examples of acid generators include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, and 4-acetoxyphenyl methyl sulfonate. Onium salts such as benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyl tosylate, Examples include benzointosylates.

The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and O-acyloxy A polymerization initiator containing a rubber compound is more preferred.

The content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably The amount is 1 part by mass or more and 20 parts by mass or less. When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, so that the productivity of the color filter is improved.

5. Polymerization initiation aid (D1)
The colored composition of the present invention may contain a polymerization initiation aid (D1). The polymerization initiation aid (D1) is a compound or a sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. The polymerization initiation aid (D1) is usually used in combination with the polymerization initiator (D).
Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

The amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, -2-ethylhexyl dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis Examples thereof include (ethylmethylamino)benzophenone, and among them, 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) may also be used.

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

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

The carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, Examples include N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

When using these polymerization initiation aids (D1), the content thereof is preferably 0.1 parts by mass or more and 30 parts by mass based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). The content is preferably 1 part by mass or more and 20 parts by mass or less. When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with even higher sensitivity, and the productivity of color filters tends to improve.

6. Solvent (E)
The solvent (E) is not particularly limited, and any solvent commonly used in the field can be used. For example, ester solvents (solvents that contain -COO- but no -O- in the molecule), ether solvents (solvents that contain -O- but no -COO- in the molecule), and ether ester solvents (solvents that contain -O- but no -COO- in the molecule). solvents containing -COO- and -O-), ketone solvents (solvents containing -CO- in the molecule but not -COO-), alcohol solvents (solvents containing OH in the molecule, -O-, - (CO- and -COO--free solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone, with ethyl lactate being preferred.

Ether solvents 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, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl Examples include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, and methylanisole, with propylene glycol monomethyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, and diethylene glycol monoethyl ether being preferred.

Ether ester solvents include methyl methoxy acetate, ethyl methoxy acetate, butyl methoxy acetate, methyl ethoxy acetate, ethyl ethoxy acetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propionate, 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 Examples include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate, with propylene glycol monomethyl ether acetate and ethyl 3-ethoxypropionate being preferred, and propylene glycol monomethyl ether acetate being particularly preferred.

Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, and cyclopentanone. Examples include non, cyclohexanone and isophorone, with 4-hydroxy-4-methyl-2-pentanone being preferred.

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

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

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

As the solvent (E), at least one selected from the group consisting of ester solvents, ether solvents, ether ester solvents, ketone solvents, and amide solvents is more preferable, and the group consisting of ester solvents, ether ester solvents, and ketone solvents is more preferable. More preferably, at least one selected from the following.

Further, from the viewpoint of coating properties and drying properties, the above-mentioned solvent is preferably selected from those having a boiling point of 120° C. or more and 180° C. or less at 1 atm. Examples of solvents that satisfy this boiling point condition include propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Hydroxy-4-methyl-2-pentanone and N,N-dimethylformamide are preferred, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2 -Pentanone is more preferred.

The content of the solvent (E) is preferably 55% by mass or more and 95% by mass or less, more preferably 60% by mass or more and 92% by mass or less, based on the total amount of the colored composition of the present invention. In other words, the total solid content of the coloring composition is preferably 5% by mass or more and 45% by mass or less, more preferably 8% by mass or more and 40% by mass or less. When the content of the solvent (E) is within the above range, flatness during coating will be good, and display characteristics will tend to be good since the color density will not be insufficient when forming a color filter. .

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

Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC). .

Examples of the above-mentioned fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule. Specifically, Florado (registered trademark) FC430, Florado FC431 (manufactured by Sumitomo 3M Ltd.), Megafac (registered trademark) F142D, Florado (registered trademark) F171, Florado F172, Florado F173, Florado F177, Florado F183, Florado F554, Megafac (registered trademark) R30, RS-718-K (manufactured by DIC Corporation), EFTOP (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Examples include S382, SC101, SC105 (manufactured by AGC Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Research Institute).

Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, Megafac (registered trademark) BL20, Megafac (registered trademark) F475, Megafac (registered trademark) F477, and Megafac (registered trademark) F443 (manufactured by DIC Corporation) may be mentioned.

The content of the leveling agent (F) is preferably 0.001% by mass or more and 0.2% by mass or less, more preferably 0.002% by mass or more and 0.1% by mass, based on the total amount of the coloring composition. The content is preferably 0.005% by mass or more and 0.05% by mass or less. Note that this content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

8. Other components The coloring composition of the present invention may optionally contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, etc. May include.

<Method for producing colored composition>
The colored composition of the present invention includes, for example, a coloring agent (A) containing compound (I), a resin (B) used as necessary, a polymerizable compound (C), a polymerization initiator (D), a polymerization initiator It can be prepared by mixing the auxiliary agent (D1), the solvent (E), the leveling agent (F), and other components. Mixing can be performed using known or conventional equipment and conditions.

The colorant (A) may be mixed in advance with part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle diameter becomes about 0.2 μm or less. At this time, part or all of the dispersant and resin (B) may be blended as necessary. It is preferable to prepare the desired colored composition by mixing the remaining components with the dispersion obtained in this manner so as to have a predetermined concentration. When using a bead mill, the diameter of the beads is preferably 0.05 mm or more and 0.5 mm or less, and examples of the material of the beads include glass, ceramic, and metal.

<Production method of color filter>
Examples of the method for producing a colored pattern of a color filter from the colored composition of the present invention include a photolithography method, an inkjet method, and a printing method. Among these, photolithography is preferred. The photolithography method is a method of forming a colored pattern by applying the colored composition to a substrate, drying it to form a composition layer, exposing the composition layer through a photomask, and developing it. It is. In the photolithography method, by not using a photomask and/or not developing during exposure, a colored coating film that is a cured product of the composition layer can be formed. The colored pattern and colored coating film thus formed are the color filter of the present invention.

The film thickness of the color filter is not particularly limited, and can be adjusted as appropriate depending on the purpose and use, for example, from 0.1 μm to 30 μm, preferably from 0.1 μm to 20 μm, more preferably from 0.1 μm to 20 μm. is 0.5 μm or more and 6 μm or less.

Examples of substrates include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass whose surface is coated with silica, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, and the like. A material on which a thin film of aluminum, silver, silver/copper/palladium alloy, etc. is formed is used. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates. Alternatively, a substrate obtained by performing HMDS treatment on a silicon substrate may be used.

Formation of each color pixel by photolithography can be performed using known or conventional equipment and conditions. For example, it can be produced as follows. First, a colored composition is applied onto a substrate, and volatile components such as a solvent are removed by heating drying (prebaking) and/or vacuum drying to obtain a smooth composition layer. Examples of the coating method include spin coating, slit coating, slit and spin coating, and the like. The temperature when performing heat drying is preferably 30°C or more and 120°C or less, more preferably 50°C or more and 110°C or less. The heating time is preferably 10 seconds or more and 60 minutes or less, more preferably 30 seconds or more and 30 minutes or less. When drying under reduced pressure is performed, it is preferably carried out under a pressure of 50 to 150 Pa and at a temperature of 20 to 25°C. The thickness of the composition layer is not particularly limited, and may be appropriately selected depending on the thickness of the intended color filter.

Next, the composition layer is exposed through a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern depending on the intended use is used. The light source used for exposure is preferably a light source that generates light with a wavelength of 250 to 450 nm. For example, light of less than 250 nm can be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm can be selectively extracted using a band pass filter that extracts these wavelength ranges. You can also Specific examples include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like. Because it is possible to uniformly irradiate parallel light over the entire exposure surface and to accurately align the photomask and substrate, it is possible to use reduction projection exposure equipment or proximity exposure equipment such as mask aligners and steppers. preferable.

By bringing the exposed composition layer into contact with a developer and developing it, a colored pattern is formed on the substrate. By development, the unexposed areas of the composition layer are dissolved in a developer and removed. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may contain a surfactant. The developing method may be any of the paddle method, dipping method, spray method, etc. Furthermore, the substrate may be tilted at an arbitrary angle during development.
After development, it is preferable to wash with water.

Furthermore, it is preferable to post-bake the obtained colored pattern and colored coating film. The post-bake temperature is preferably 80°C or higher and 250°C or lower, more preferably 100°C or higher and 245°C or lower. The post-bake time is preferably 1 minute or more and 120 minutes or less, more preferably 2 minutes or more and 30 minutes or less.

The colored pattern and colored coating film thus obtained are useful as color filters, and the color filters can be used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state image sensors, etc. It is useful as a color filter.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited by these Examples. In the Examples and Comparative Examples, % and parts representing the content or amount used are based on mass unless otherwise specified.

In the following examples, the structure of the compound was confirmed using a 400 MHz superconducting Fourier transform nuclear magnetic resonance apparatus (Varian 400-MR; manufactured by Agilent) and mass spectrometry (LC; model 1200 manufactured by Agilent, MASS; LC/MSD 6130 type manufactured by Agilent). did.

[Compound synthesis example]
<Synthesis of compound (I-1)>
90 parts of methanol, 60 parts of acetic acid, 194 parts of 35% hydrochloric acid, and 150 parts of water were added to 30 parts of 2,5-dichloro-1,4-phenylenediamine and stirred. Under ice cooling, an aqueous solution prepared by dissolving 14 parts of sodium nitrite in 21 parts of water was added to the reaction solution and stirred for 2 hours to obtain a suspension containing a diazonium salt. On the other hand, 105 parts of methanol was added to 30 parts of 3-methyl-1-phenyl-5-pyrazolone, and then 412 parts of a 25% aqueous sodium hydroxide solution was added and stirred under ice cooling. A suspension containing the diazonium salt was added dropwise thereto. After the dropwise addition was completed, the mixture was further stirred at room temperature for 1 hour to obtain an orange suspension. The orange solid obtained by filtration was dried at 60° C. under reduced pressure to obtain a compound represented by formula (1).

Next, 120 parts of methanesulfonic acid and 118 parts of 98% sulfuric acid were added to 30 parts of the compound represented by formula (1) and stirred. Under ice-cooling, an aqueous solution prepared by dissolving 5.7 parts of sodium nitrite in 9.0 parts of water was added to the reaction solution and stirred for 2 hours to obtain a suspension containing a diazonium salt. On the other hand, 104 parts of methanol and 467 parts of a 25% aqueous sodium hydroxide solution were added to 14 parts of antipyrine and stirred. The suspension containing the diazonium salt was added dropwise thereto under ice cooling, and the mixture was further stirred at room temperature for 1 hour to obtain a red suspension. After dispersing and washing the red solid obtained by filtration with water and methanol, the azo compound represented by formula (I-1) (hereinafter referred to as compound (I -1)) 9.7 parts (yield 21%) were obtained.
(Mass spectrometry) Ionization mode = ESI-: m/z = 560.8 [MH] ^-

<Synthesis of compound (a-1)>
A compound represented by formula (a-1) (hereinafter referred to as compound (a-1)) was synthesized according to the content described in Dyes and Pigments 80 (2009) 245-253.

<Synthesis of compound (X1)>
A compound represented by formula (X1) was synthesized according to the content described in JP-A-2002-179979.

<Synthesis of compound (X2)>
56 parts of water, 22 parts of acetic acid, 45 parts of methanol, and 78 parts of 98% sulfuric acid were added to 22 parts of 2,5-dichloro-4-nitroaniline and stirred. Under ice cooling, an aqueous solution prepared by dissolving 15 parts of sodium nitrite in 22 parts of water was added to the reaction solution and stirred for 2 hours to obtain a suspension containing a diazonium salt. On the other hand, 67 parts of methanol was added to 17 parts of 3-methyl-1-phenyl-5-pyrazolone, and then 234 parts of a 25% aqueous sodium hydroxide solution was added and stirred under ice cooling. A suspension containing the diazonium salt was added dropwise thereto. After the dropwise addition was completed, the mixture was further stirred at room temperature for 1 hour to obtain an orange suspension. The orange solid obtained by filtration was dried at 60° C. under reduced pressure to obtain a compound represented by formula (x-1).

Subsequently, 129 parts of water, 16 parts of sodium hydrogen carbonate, and 47 parts of sodium sulfide nonahydrate were added to 38 parts of the compound represented by formula (x-1), and the mixture was stirred at 85°C for 2 hours. After cooling the reaction solution to room temperature, the reaction solution was neutralized to pH 6 with 35% hydrochloric acid, and the precipitated solid was collected by filtration. The obtained solid was washed with water and filtered, and the obtained red solid was dried at 60° C. under reduced pressure to obtain a compound represented by formula (x-2).

Next, 4.1 parts of N-methyl-2-pyrrolidone, 1.5 parts of acetic acid, and 20 parts of 80% sulfuric acid were added to 1.0 parts of the compound represented by formula (x-2) and stirred. Under ice-cooling, an aqueous solution of 0.2 parts of sodium nitrite dissolved in 0.4 parts of water was added to the reaction solution and stirred for 2 hours, then 0.1 part of sulfamic acid was added to 0.5 parts of water, 5 parts of acetic acid. One part of the aqueous solution was added to the reaction solution and stirred to obtain a suspension containing the diazonium salt. Meanwhile, 15 parts of N-methyl-2-pyrrolidone and 41 parts of water were added to 0.7 parts of 3-methyl-1-(4-sulfophenyl)-2-pyrazolin-5-one, and the mixture was stirred for 30 minutes. A suspension containing the diazonium salt and 23 parts of 25% aqueous ammonia were added dropwise thereto under ice cooling, and the mixture was further stirred at room temperature for 1 hour to obtain a red suspension. The red solid obtained by filtration was dispersed and washed with water and methanol for 30 minutes each, collected by filtration, and dried at 60°C under reduced pressure to obtain an azo compound represented by formula (X2) (hereinafter referred to as compound (X2)). )) 0.5 part (yield 27%) was obtained.
¹ H-NMR (DMSO-d6): δ2.34 (s, 3H), δ2.35 (s, 3H),
δ6.94-7.32 (br, 4H), δ7.23 (t, 1H), δ7.46 (t, 2H
), δ7.69 (d, 2H), δ7.86 (d, 2H), δ7.88 (m, 2H), δ7.99 (s, 1H), δ8.00 (s, 1H), δ13.50 (br, 2H)

<Resin synthesis example 1>
In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, the atmosphere was replaced with nitrogen, and 280 parts of propylene glycol monomethyl ether acetate was placed therein, and the flask was heated to 80° C. with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2, A mixed solution of 289 parts of a mixture of decane-9-yl acrylate (content ratio: 1:1 in molar ratio) and ¹²⁵ parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition was completed, the mixture was held at 80°C for 4 hours, then cooled to room temperature, and a copolymer (resin B-1)) solution was obtained. The weight average molecular weight (Mw) of the obtained copolymer was 9.2×10 ³ , the molecular weight distribution (Mw/Mn) was 2.08, and the acid value (in terms of solid content) was 77 mg-KOH/g. Resin (B-1) has the following structural units.

The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin in terms of polystyrene were measured by GPC method under the following conditions.
Equipment: HLC-8120GPC (manufactured by Tosoh Corporation)
Column; TSK-GELG2000HXL
Column temperature: 40℃
Solvent: THF
Flow rate: 1.0mL/min
Test liquid solid content concentration: 0.001 to 0.01% by mass
Injection volume: 50μL
Detector; RI
Calibration standard material ;TSK STANDARD POLYSTYRENE
F-40, F-4, F-288, A-2500, A-500
(manufactured by Tosoh Corporation)
The ratio of the weight average molecular weight and number average molecular weight (Mw/Mn) in terms of polystyrene obtained above was defined as the degree of dispersion.

<Resin synthesis example 2>
A suitable amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere, and 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added thereto and heated to 85° C. with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^{2, [6} ] A mixed solution of 25 parts of a mixture of decane-9-yl acrylate (content ratio 1:1 in molar ratio), 137 parts of N-cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added. The mixture was added dropwise over 5 hours. Meanwhile, a solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition was completed, the temperature was maintained at 85°C for 4 hours, and then cooled to room temperature. A copolymer (resin (B- 2)) A solution was obtained. The weight average molecular weight Mw of the produced copolymer was 8.0×10 ³ , the degree of dispersion was 2.1, and the acid value in terms of solid content was 109 mg-KOH/g. Resin (B-2) has the following structural units.

<Dispersion liquid preparation example 1>
4.5 parts of compound (a-1), 0.5 parts of compound (I-1), dispersant (BYK-LP N 6919 manufactured by BYK) 3.5 parts (in terms of solid content), resin (B-1) (in terms of solid content), 83 parts of propylene glycol monomethyl ether acetate (hereinafter sometimes referred to as PGMEA), and 5.0 parts of diacetone alcohol (hereinafter sometimes referred to as DAA), and 300 parts of 2 mm zirconia beads were added and shaken, and the zirconia beads were removed by filtration to obtain a dispersion (A-1).

<Dispersion liquid preparation example 2>
4.3 parts of compound (a-1), 0.8 parts of compound (I-1), 3.5 parts of dispersant (BYK-LP N 6919 manufactured by BYK) (in terms of solid content), resin (B-1) Mix 3.5 parts (in terms of solid content), 83 parts of PGMEA, and 5.0 parts of DAA, add 300 parts of 0.2 mm zirconia beads, shake, and remove the zirconia beads by filtration to obtain a dispersion (A-2). I got it.

<Dispersion liquid preparation example 3>
3.8 parts of compound (a-1), 1.3 parts of compound (I-1), 3.5 parts of dispersant (BYK-LP N 6919 manufactured by BYK) (in terms of solid content), resin (B-1) Mix 3.5 parts (in terms of solid content), 83 parts of PGMEA, and 5.0 parts of DAA, add 300 parts of 0.2 mm zirconia beads, shake, and remove the zirconia beads by filtration to obtain a dispersion (A-3). I got it.

<Dispersion liquid preparation example 4>
Compound (a-1) 4.8 parts, compound (I-1) 0.3 parts, dispersant (BYK-LP N 6919 manufactured by BYK) (solid content equivalent) 3.5 parts, resin (B-1) Mix 3.5 parts (in terms of solid content), 83 parts of PGMEA, and 5.0 parts of DAA, add 300 parts of 0.2 mm zirconia beads, shake, and remove the zirconia beads by filtration to obtain a dispersion (A-4). I got it.

<Dispersion liquid preparation example 5>
Compound (I-1) 5.0 parts, dispersant (BYK-LP N 6919 manufactured by BYK) (solid content equivalent) 3.5 parts, resin (B-1) (solid content equivalent) 3.5 parts, PGMEA83 1 part and 5.0 parts of DAA were mixed, 300 parts of 0.2 mm zirconia beads were added, and the mixture was shaken. The zirconia beads were removed by filtration to obtain a dispersion liquid (A-5).

<Dispersion liquid preparation example 6>
C. I. Pigment Orange 13 (hereinafter referred to as PO13) 4.5 parts, compound (I-1) 0.5 parts, dispersant (BYK Corporation BYK-LP N 6919) (solid content equivalent) 3.5 parts, resin (B- 1) Mix 3.5 parts (in terms of solid content), 83 parts of PGMEA, and 5.0 parts of DAA, add 300 parts of 0.2 mm zirconia beads, shake, and remove the zirconia beads by filtration to obtain a dispersion (A- 6) was obtained.

<Dispersion liquid preparation example 7>
C. I. Pigment Red 269 (hereinafter referred to as PR269) 4.5 parts, Compound (I-1) 0.5 parts, dispersant (BYK-LP N 6919 manufactured by BYK) (solid content equivalent) 3.5 parts, resin (B- 1) Mix 3.5 parts (in terms of solid content), 83 parts of PGMEA, and 5.0 parts of DAA, add 300 parts of 0.2 mm zirconia beads, shake, and remove the zirconia beads by filtration to obtain a dispersion (A- 7) was obtained.

<Dispersion liquid preparation example 8>
Compound (a-1) 5.0 parts, dispersant (BYK-LP N 6919 manufactured by BYK) (solid content equivalent) 3.5 parts, resin (B-1) (solid content equivalent) 3.5 parts, PGMEA83 1 part and 5.0 parts of DAA were mixed, 300 parts of 0.2 mm zirconia beads were added thereto, the mixture was shaken, and the zirconia beads were removed by filtration to obtain a dispersion liquid (A-8).

<Dispersion liquid preparation examples 9 to 10>
Dispersion liquid (A-9) to dispersion liquid (A- 10) was obtained.
Dispersion (A-9): Compound (X1)
Dispersion (A-10): Compound (X2)

<Dispersion liquid preparation examples 11 to 12>
Dispersion liquid (A-11) to dispersion liquid (A- 12) was obtained.
Dispersion liquid (A-11): PO13
Dispersion liquid (A-12): PR269

<Dispersion liquid preparation example 13>
A dispersion (A-13) was obtained in the same manner as the dispersion (A-10) except that compound (a-1) in the dispersion (A-10) was changed to PO13.

<Example 1>
(A) Colorant: Dispersion (A-1) 410 parts (B) Resin: Resin (B-2) (solid content equivalent) 100 parts (C) Polymerizable compound: Trimethylolpropane triacrylate (trade name: A -TMPT: Shin-Nakamura Chemical Industry Co., Ltd.) 50 parts (D) Polymerization initiator: N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine (product) Name: TR-PBG-327 (manufactured by Changzhou Strong Electronics New Materials Co., Ltd.) 5 parts (E) Solvent: Propylene glycol monomethyl ether acetate 750 parts (E) Solvent: Ethyl lactate 60 parts (F) Leveling agent: Polyether modified A colored curable resin composition was obtained by mixing 0.12 parts of silicone oil (Toray Silicone SH8400, manufactured by Dow Corning Toray Co., Ltd.).

<Examples 2 to 7 and Comparative Examples 1 to 6>
Colored compositions of Examples 2 to 7 and Comparative Examples 1 to 6 were obtained in the same manner as in Example 1, except that the dispersion liquid (A-1) of Example 1 was changed to the following dispersion liquid. .
Example 2: Dispersion (A-2)
Example 3: Dispersion (A-3)
Example 4: Dispersion (A-4)
Example 5: Dispersion (A-5)
Example 6: Dispersion (A-6)
Example 7: Dispersion (A-7)
Comparative example 1: Dispersion liquid (A-8)
Comparative Example 2: Dispersion (A-9)
Comparative example 3: Dispersion liquid (A-10)
Comparative example 4: Dispersion liquid (A-11)
Comparative Example 5: Dispersion (A-12)
Comparative Example 6: Dispersion (A-13)

<Formation of color filter (colored coating film)>
The colored compositions obtained in Examples 1 to 7 and Comparative Examples 1 to 6 were applied on a 2-inch square glass substrate (Eagle A colored composition layer was obtained. After cooling, it was irradiated with light using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) at an exposure dose of 60 mJ/cm ² (based on 365 nm) in an air atmosphere without using a photomask. A colored coating film was obtained by post-baking the colored composition layer after light irradiation at 230° C. for 20 minutes in an oven. After cooling, the thickness of the obtained colored coating film was measured using a film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Technology Co., Ltd.).

<Red transparency color evaluation>
The colored coating films obtained in Examples 1 to 7 and Comparative Examples 1 to 2, and 4 to 5 were spectrally measured using a colorimeter (LVmicro-Z; manufactured by Lambda Vision Co., Ltd.) to determine the maximum absorption. The height of the transmittance in the red region of 630 nm was evaluated when the wavelength transmittance was set to 1.0% (absorbance conversion 2). The higher the transmittance in the region, the higher the color performance when used as a red color filter. The results are shown in Table 7.

The colored coating film obtained using the compound (I) of the present invention has increased transmittance in the red region of 630 nm. In particular, Examples 1 to 4 in which compound (I) of the present invention was added to compound (a-1), Comparative Example 1 in which compound (I) was not added, and compound (I) in place of compound (I) Compared with Comparative Example 2 in which X1) was added, the transmittance in the red region of 630 nm was increased. In addition, in Example 6 in which Compound (I) was added to PO13, the transmittance in the red region 630 nm was increased compared to Comparative Example 4 in which Compound (I) was not added. Example 7 in which Compound (I) was added also had higher transmittance in the red region of 630 nm compared to Comparative Example 5 in which Compound (I) was not added.

<Foreign substance evaluation>
The colored compositions obtained in Examples 1, 4, and 6 and Comparative Examples 3, 4, and 6 were applied on a 2-inch square glass substrate (Eagle A colored composition layer was obtained by prebaking at ℃ for 3 minutes. After cooling, it was irradiated with light at an exposure dose of 60 mJ/cm ² (based on 365 nm) in an air atmosphere through a photomask having a line pattern using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). . The colored composition layer after light irradiation was developed by immersing it in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 24°C for 60 seconds, and after washing with water, it was developed in an oven for 230 minutes. A colored coating film was obtained by post-baking at ℃ for 20 minutes. After cooling, foreign matter between the obtained line patterns was evaluated using a laser microscope (OLS4100; manufactured by Olympus Corporation). Further, the obtained colored coating film was baked in an oven at 230° C. for 60 minutes (additional baking), and then foreign matter between the obtained line patterns was evaluated. The results are shown in Table 8. The smaller the number in Table 8, the fewer the number of foreign particles, which contributes to the formation of a good pattern. The evaluation criteria are shown below.
1: No foreign matter was found at all. 2: Foreign matter was found between the lines in an amount of approximately 1 to 5 area%, but it was not a problem. 3: Foreign matter was found in an amount of approximately 6 to 15 area% between the lines. However, there is no problem. 4: Foreign matter is found between the lines by approximately 16% or more of the area, and the product cannot be used.

<Viscosity evaluation>
The viscosity (=initial viscosity) of the colored composition immediately after production was measured using a cone plate type (E type) viscometer ("Viscometer TV-25" manufactured by Toki Sangyo Co., Ltd.) at a rotation speed of 100 rpm and a measurement temperature of 23 ° C. It was measured using The results are shown in Table 9. From the results below, it can be seen that compound (I) contributes to lowering the viscosity of the composition containing the pigment.

According to the compound and coloring composition of the present invention, the transmittance of the resulting coating film at 630 nm can be increased, and foreign matter between line patterns after development can be reduced, so that a color filter with excellent properties can be provided. can do. Furthermore, by adding the compound of the present invention to a colored composition, it is possible to lower the viscosity, so it is possible to provide a colored composition with excellent workability during mixing and coating.

Claims (7)

A colored composition containing a compound represented by formula (I).

[In formula (I),
R ¹ and R ³ each independently represent a hydrocarbon group, a heterocyclic group, a cyano group, or a halogen atom that may have a substituent.
R ² , R ⁴ and R ⁵ each independently represent a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, a cyano group, or a halogen atom.
X ¹ represents a substituent or a hydrocarbon group which may have a substituent.
n represents an integer from 0 to 4. When n represents an integer of 2 or more, the plurality of X ¹ may be the same or different. When n represents an integer of 2 or more and X ¹ is bonded to adjacent carbon atoms, X ¹ bonded to adjacent carbon atoms may be bonded to each other to form a ring. -CH ₂ - contained in the ring skeleton may be replaced with -O-, -CO- or -NH-, and -CH= contained in the ring skeleton may be replaced with -N=. Good too. ] The colored composition according to claim 1, further comprising a pigment. The coloring composition according to claim 1, further comprising an alkali-soluble resin. The colored composition according to claim 3, further comprising a solvent, a polymerizable compound, and a polymerization initiator. A color filter formed from the colored composition according to any one of claims 1 to 4. A display device comprising the color filter according to claim 5. A compound represented by formula (I).

[In formula (I),
R ¹ and R ³ each independently represent a hydrocarbon group, a heterocyclic group, a cyano group, or a halogen atom that may have a substituent.
R ² , R ⁴ and R ⁵ each independently represent a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, a cyano group, or a halogen atom.
X ¹ represents a substituent or a hydrocarbon group which may have a substituent.
n represents an integer from 0 to 4. When n represents an integer of 2 or more, the plurality of X ¹ may be the same or different. When n represents an integer of 2 or more and X ¹ is bonded to adjacent carbon atoms, X ¹ bonded to adjacent carbon atoms may be bonded to each other to form a ring. -CH ₂ - contained in the ring skeleton may be replaced with -O-, -CO- or -NH-, and -CH= contained in the ring skeleton may be replaced with -N=. Good too. ]