JP7532141B2 - Compound and coloring composition - Google Patents

Description

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

Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are manufactured from coloring compositions. In particular, red color filters may be manufactured from coloring compositions that contain a yellow coloring material in addition to a red coloring material, and C.I. Pigment Yellow 185 and the like are known as such yellow coloring materials (Patent Document 1).

JP 2012-203146 A

However, color filters formed from coloring compositions containing the above yellow coloring material may not have sufficient heat resistance. Therefore, the present invention aims to provide a compound and a coloring composition capable of forming a color filter with excellent heat resistance.

［式（Ｉ）中、
Ｒ¹、Ｒ²、Ｒ⁴及びＲ⁵は、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、－ＳＯ₃Ｍ、－ＣＯ₂Ｍ、ＭＭ、炭素数１～４０の１価の炭化水素基又は炭素数１～４０の１価の複素環基を表し、
該１価の炭化水素基及び該１価の複素環基を構成する－Ｃ（－）（－）－は、－Ｓｉ（－）（－）－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ（－）－は、－Ｎ（－）－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ＝は、－Ｎ＝に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ₂－は、－Ｏ－、－Ｓ－、－Ｓ（Ｏ）₂－又は－ＣＯ－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、－ＳＯ₃Ｍ、－ＣＯ₂Ｍ又はＭＭに置き換わっていてもよい。
Ｒ³は、ハロゲン原子または電子供与性基を表す。
Ｒ¹及びＲ²は、互いに結合して環を形成していてもよい。
Ｍは、水素原子、アルカリ金属原子、配位子を有していてもよい金属原子又はＮ（Ｚ¹）（Ｚ²）（Ｚ³）（Ｚ⁴）を表す。
ＭＭは、アルカリ金属原子、配位子を有していてもよい金属原子又はＮ（Ｚ¹）（Ｚ²）（Ｚ³）（Ｚ⁴）を表す。
Ｚ¹～Ｚ⁴は、それぞれ独立して、水素原子、炭素数１～４０の１価の炭化水素基又は炭素数１～４０の１価の複素環基を表し、
該１価の炭化水素基及び該１価の複素環基を構成する－Ｃ（－）（－）－は、－Ｓｉ（－）（－）－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ（－）－は、－Ｎ（－）－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ＝は、－Ｎ＝に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ₂－は、－Ｏ－、－Ｓ－、－Ｓ（Ｏ）₂－又は－ＣＯ－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、－ＳＯ₃Ｍ、－ＣＯ₂Ｍ又はＭＭに置き換わっていてもよい。
Ｑ¹及びＱ²は、それぞれ独立して、２価の炭化水素基又は２価の複素環基を表し、
該２価の炭化水素基及び該２価の複素環基を構成する－Ｃ（－）（－）－は、－Ｓｉ（－）（－）－に置き換わっていてもよく、
該２価の炭化水素基及び該２価の複素環基を構成する－ＣＨ（－）－は、－Ｎ（－）－に置き換わっていてもよく、
該２価の炭化水素基及び該２価の複素環基を構成する－ＣＨ＝は、－Ｎ＝に置き換わっていてもよく、
該２価の炭化水素基及び該２価の複素環基を構成する－ＣＨ₂－は、－Ｏ－、－Ｓ－、－Ｓ（Ｏ）₂－又は－ＣＯ－に置き換わっていてもよく、
該２価の炭化水素基及び該２価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、－ＳＯ₃Ｍ、－ＣＯ₂Ｍ又はＭＭに置き換わっていてもよい。
Ｚ¹～Ｚ⁴、Ｍ及びＭＭがそれぞれ複数存在する場合、それらは互いに同一又は異なっていてよい。］
［２］ 式（Ｉ）におけるＱ¹及びＱ²が、それぞれ独立して、式（ＱＱ１）または式（ＱＱ２）で表される基である［１］に記載の化合物。

［式（ＱＱ１）～式（ＱＱ２）中、
Ｒ^Q1～Ｒ^Q10は、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、－ＳＯ₃Ｍ、－ＣＯ₂Ｍ、ＭＭ、炭素数１～４０の１価の炭化水素基又は炭素数１～４０の１価の複素環基を表し、
該１価の炭化水素基及び該１価の複素環基を構成する－Ｃ（－）（－）－は、－Ｓｉ（－）（－）－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ（－）－は、－Ｎ（－）－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ＝は、－Ｎ＝に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ₂－は、－Ｏ－、－Ｓ－、
－Ｓ（Ｏ）₂－又は－ＣＯ－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、－ＳＯ₃Ｍ、－ＣＯ₂Ｍ又はＭＭに置き換わっていてもよい。
Ｒ^Q1～Ｒ^Q4は、それぞれ互いにＲ^Q1～Ｒ^Q4から選ばれる１つ以上と結合して環を形成してもよく
Ｒ^Q5～Ｒ^Q10は、それぞれ互いにＲ^Q5～Ｒ^Q10から選ばれる１つ以上と結合して環を形成してもよい。
Ｍ及びＭＭは、前記と同一の意味を表す。
※は、結合手を表す。］
［３］ ［１］又は［２］に記載の化合物と、赤色色材とを含む着色組成物。
［４］ さらに、樹脂を含む［３］に記載の着色組成物。
［５］ さらに、重合性化合物及び重合開始剤を含む［３］又は［４］に記載の着色組成物。
［６］ ［３］～［５］のいずれか１項に記載の着色組成物から形成されるカラーフィルタ。
［７］ ［６］に記載のカラーフィルタを含む表示装置。 The gist of the present invention is as follows.
[1] A compound represented by formula (I):

[In formula (I),
R ¹ , R ² , R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms;
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -O-, -S-, -S(O) ₂ - or -CO-;
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by halogen atoms, cyano groups, nitro groups, --SO ₃ M, --CO ₂ M or MM.
^R3 represents a halogen atom or an electron donating group.
R ¹ and R ² may be bonded to each other to form a ring.
M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ).
MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ).
Z ¹ to Z ⁴ each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms;
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -O-, -S-, -S(O) ₂ - or -CO-;
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by halogen atoms, cyano groups, nitro groups, --SO ₃ M, --CO ₂ M or MM.
^Q1 and ^Q2 each independently represent a divalent hydrocarbon group or a divalent heterocyclic group;
-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -Si(-)(-)-;
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -N=,
-CH ₂ - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -O-, -S-, -S(O) ₂ - or -CO-;
The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by halogen atoms, cyano groups, nitro groups, --SO ₃ M, --CO ₂ M or MM.
When a plurality of Z ¹ to Z ⁴ , M and MM are present, they may be the same or different.
[2] The compound according to [1], wherein Q ¹ and Q ² in formula (I) are each independently a group represented by formula (QQ1) or formula (QQ2).

[In formula (QQ1) to formula (QQ2),
R ^Q1 to R ^Q10 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms;
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N=,
The -CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is -O-, -S-,
may be replaced by -S(O) _2- or -CO-;
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by halogen atoms, cyano groups, nitro groups, --SO ₃ M, --CO ₂ M or MM.
R ^Q1 to R ^Q4 may each be bonded to one or more selected from R ^Q1 to R ^Q4 to form a ring, and R ^Q5 to R ^Q10 may each be bonded to one or more selected from R ^Q5 to R ^Q10 to form a ring.
M and MM have the same meanings as defined above.
* represents a bond.
[3] A coloring composition comprising the compound according to [1] or [2] and a red colorant.
[4] The coloring composition according to [3], further comprising a resin.
[5] The colored composition according to [3] or [4], further comprising a polymerizable compound and a polymerization initiator.
[6] A color filter formed from the colored composition according to any one of [3] to [5].
[7] A display device comprising the color filter according to [6].

The compound and coloring composition of the present invention can provide a color filter with improved heat resistance.

[Compound]
The compound according to the present invention is a compound represented by formula (I) (hereinafter, may be referred to as compound (I)). Hereinafter, the present invention will be described in detail using formula (I), but compound (I) also includes its tautomers.

［式（Ｉ）中、
Ｒ¹、Ｒ²、Ｒ⁴及びＲ⁵は、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、－ＳＯ₃Ｍ、－ＣＯ₂Ｍ、ＭＭ、炭素数１～４０の１価の炭化水素基又は炭素数１～４０の１価の複素環基を表し、
該１価の炭化水素基及び該１価の複素環基を構成する－Ｃ（－）（－）－は、－Ｓｉ（－）（－）－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ（－）－は、－Ｎ（－）－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ＝は、－Ｎ＝に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ₂－は、－Ｏ－、－Ｓ－、－Ｓ（Ｏ）₂－又は－ＣＯ－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、－ＳＯ₃Ｍ、－ＣＯ₂Ｍ又はＭＭに置き換わっていてもよい。
Ｒ³は、ハロゲン原子または電子供与性基を表す。
Ｒ¹及びＲ²は、互いに結合して環を形成していてもよい。
Ｍは、水素原子、アルカリ金属原子、配位子を有していてもよい金属原子又はＮ（Ｚ¹）（Ｚ²）（Ｚ³）（Ｚ⁴）を表す。
ＭＭは、アルカリ金属原子、配位子を有していてもよい金属原子又はＮ（Ｚ¹）（Ｚ²）（Ｚ³）（Ｚ⁴）を表す。
Ｚ¹～Ｚ⁴は、それぞれ独立して、水素原子、炭素数１～４０の１価の炭化水素基又は炭素数１～４０の１価の複素環基を表し、
該１価の炭化水素基及び該１価の複素環基を構成する－Ｃ（－）（－）－は、－Ｓｉ（－）（－）－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ（－）－は、－Ｎ（－）－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ＝は、－Ｎ＝に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する－ＣＨ₂－は、－Ｏ－、－Ｓ－、－Ｓ（Ｏ）₂－又は－ＣＯ－に置き換わっていてもよく、
該１価の炭化水素基及び該１価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、－ＳＯ₃Ｍ、－ＣＯ₂Ｍ又はＭＭに置き換わっていてもよい。
Ｑ¹及びＱ²は、それぞれ独立して、２価の炭化水素基又は２価の複素環基を表し、
該２価の炭化水素基及び該２価の複素環基を構成する－Ｃ（－）（－）－は、－Ｓｉ（－）（－）－に置き換わっていてもよく、
該２価の炭化水素基及び該２価の複素環基を構成する－ＣＨ（－）－は、－Ｎ（－）－に置き換わっていてもよく、
該２価の炭化水素基及び該２価の複素環基を構成する－ＣＨ＝は、－Ｎ＝に置き換わっていてもよく、
該２価の炭化水素基及び該２価の複素環基を構成する－ＣＨ₂－は、－Ｏ－、－Ｓ－、－Ｓ（Ｏ）₂－又は－ＣＯ－に置き換わっていてもよく、
該２価の炭化水素基及び該２価の複素環基を構成する水素原子は、ハロゲン原子、シアノ基、ニトロ基、－ＳＯ₃Ｍ、－ＣＯ₂Ｍ又はＭＭに置き換わっていてもよい。
Ｚ¹～Ｚ⁴、Ｍ及びＭＭがそれぞれ複数存在する場合、それらは互いに同一又は異なっていてよい。］

[In formula (I),
R ¹ , R ² , R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms;
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -O-, -S-, -S(O) ₂ - or -CO-;
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by halogen atoms, cyano groups, nitro groups, --SO ₃ M, --CO ₂ M or MM.
^R3 represents a halogen atom or an electron donating group.
R ¹ and R ² may be bonded to each other to form a ring.
M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ).
MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ).
Z ¹ to Z ⁴ each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms;
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -O-, -S-, -S(O) ₂ - or -CO-;
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by halogen atoms, cyano groups, nitro groups, --SO ₃ M, --CO ₂ M or MM.
^Q1 and ^Q2 each independently represent a divalent hydrocarbon group or a divalent heterocyclic group;
-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -Si(-)(-)-;
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -N=,
-CH ₂ - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -O-, -S-, -S(O) ₂ - or -CO-;
The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by halogen atoms, cyano groups, nitro groups, --SO ₃ M, --CO ₂ M or MM.
When a plurality of Z ¹ to Z ⁴ , M and MM are present, they may be the same or different.

Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms, chlorine atoms, and bromine atoms being preferred, and chlorine atoms and fluorine atoms being more preferred.

The monovalent hydrocarbon groups represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ each have 1 to 40 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, even more preferably 1 to 18 carbon atoms, and particularly preferably 1 to 12 carbon atoms.

The monovalent hydrocarbon groups having 1 to 40 carbon atoms represented by ^R1 , ^R2 , ^R4 , ^R5 , and ^Z1 to ^Z4 may be aliphatic hydrocarbon groups or aromatic hydrocarbon groups, and the aliphatic hydrocarbon groups may be saturated or unsaturated and may be linear or cyclic (alicyclic hydrocarbon groups).

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ include linear alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group;
branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1,1-dimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, and 2-ethylhexyl;
alkenyl groups such as ethenyl group (vinyl group), propenyl group (e.g., 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (e.g., 1-butenyl group, 2-butenyl group, 3-butenyl group), 3-methyl-1-butenyl group, 1,3-butadienyl group, 1-(2-propenyl)ethenyl group, 1-(1-methylethenyl)ethenyl group, 1,2-dimethyl-1-propenyl group, pentenyl group (e.g., 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group), and hexenyl group (e.g., 1-hexenyl group, 5-hexenyl group);
Alkynyl groups such as an ethynyl group, a propynyl group (eg, 1-propynyl group, 2-propynyl group), an octynyl group (eg, 1-octynyl group, 7-octynyl group), a butynyl group, a pentynyl group, and a hexynyl group; and the like.

The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 18, and particularly preferably 1 to 12. Of these, a linear or branched alkyl group having 1 to 12 carbon atoms is particularly preferred.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ include cycloalkyl groups such as a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group;
cycloalkenyl groups such as a cyclohexenyl group (for example, a cyclohex-1-en-1-yl group, a cyclohex-2-en-1-yl group, a cyclohex-3-en-1-yl group), a cycloheptenyl group, and a cyclooctenyl group;
Saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl group, norbornenyl group, adamantyl group, and bicyclo[2.2.2]octyl group; and the like.

The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, even more preferably 3 to 18, and particularly preferably 3 to 12. Among these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, or an adamantyl group is particularly preferred.

Examples of the aromatic hydrocarbon groups represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,4-dimethylphenyl group, a 2,6-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 2,4-diisopropylphenyl group, a 2,6-diisopropylphenyl group, a 4-vinylphenyl group, an o-tert-butylphenyl group, an m-tert-butylphenyl group, a p-tert-butylphenyl group, a 3,5-di(tert-butyl)phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 6-methyl-2-naphthyl group, a fluorenyl group, a phenanthryl group, an anthryl group, a perylene group and a pyrenyl group.

The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, even more preferably 6 to 18, and particularly preferably 6 to 12.

The hydrocarbon groups represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ may be groups in which the above-listed hydrocarbon groups are combined. Examples of groups in which the above-listed hydrocarbon groups are combined include a group in which an aromatic hydrocarbon group is combined with at least one selected from an aromatic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group; a group in which a chain hydrocarbon group is combined with an alicyclic hydrocarbon group; and the like.

Examples of groups combining at least one selected from aromatic hydrocarbon groups, linear hydrocarbon groups, and alicyclic hydrocarbon groups with aromatic hydrocarbon groups include aralkyl groups such as benzyl, (4-methylphenyl)methyl, and phenethyl groups; arylalkenyl groups such as 1-phenylethenyl, 2-phenylethenyl (phenylvinyl), 2,2-diphenylethenyl, and 2-phenyl-2-(1-naphthyl)ethenyl groups; arylalkynyl groups such as phenylethynyl groups; aryl (preferably phenyl) groups to which arylalkynyl groups such as (phenylethynyl)phenyl groups are bonded; phenyl groups to which one or more phenyl groups are bonded, such as biphenylyl and terphenylyl groups; cyclohexylmethylphenyl, benzylphenyl, and (dimethyl(phenyl)methyl)phenyl groups. The number of carbon atoms in these groups is preferably 7 to 30, more preferably 7 to 20, even more preferably 7 to 18, and particularly preferably 7 to 15.

In addition, examples of groups that combine a chain hydrocarbon group and an alicyclic hydrocarbon group include alkyl groups to which one or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl)methyl, cyclohexylethyl, and adamantylmethyl groups. The number of carbon atoms in these groups is preferably 4 to 30, more preferably 4 to 20, even more preferably 4 to 18, and particularly preferably 4 to 12.

The monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ represents a group containing a heteroatom as a ring component. The monovalent heterocyclic group means a group obtained by removing one hydrogen atom directly bonded to a carbon atom or heteroatom constituting the ring from a heterocycle. The monovalent heterocyclic group having 1 to 40 carbon atoms may be a monocyclic ring or a polycyclic ring. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

The number of carbon atoms in the heterocyclic group is preferably 3 to 30, more preferably 3 to 20, even more preferably 3 to 18, and particularly preferably 3 to 12.

Examples of heterocycles containing a nitrogen atom include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine, and piperazine; 5-membered unsaturated heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, and 1,2,4-triazole; 6-membered unsaturated heterocycles such as pyridine, pyridazine, pyrimine, pyrazine, and 1,3,5-triazine; condensed bicyclic heterocycles such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline such as 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, and benzopiperidine; and condensed tricyclic heterocycles such as carbazole, acridine, and phenazine.

Heterocycles containing an oxygen atom include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, and 1,4-dioxane; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane, and 1,4-dioxaspiro[4.4]nonane; α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone, and δ- Lactone-based heterocycles such as valerolactone; 5-membered ring-based unsaturated heterocycles such as furan, 2,3-dimethylfuran, 2,5-dimethylfuran, and other furans; 6-membered ring-based unsaturated heterocycles such as 2H-pyran and 4H-pyran; condensed bicyclic heterocycles such as benzofuran, benzopyran, benzodioxole, 1,3-benzodioxole, benzodioxane, chroman, and isochroman; condensed tricyclic heterocycles such as xanthene and dibenzofuran; and the like.

Examples of heterocycles containing a sulfur atom include five-membered saturated heterocycles such as dithiolane; six-membered saturated heterocycles such as thiane, 1,3-dithiane, and 2-methyl-1,3-dithiane; five-membered and six-membered unsaturated heterocycles such as thiophene, thiopyran, and benzothiopyran; condensed bicyclic heterocycles such as benzothiopyran and benzothiophene; and condensed tricyclic heterocycles such as thianthrene and dibenzothiophene.

Heterocycles containing nitrogen and oxygen atoms include monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 1-methyl-2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 1-methyl-2-piperidone, and 2-methyl-2-piperidone; monocyclic unsaturated heterocycles such as oxazole and isoxazole; condensed bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; and condensed tricyclic heterocycles such as phenoxazine.

Heterocycles containing nitrogen and sulfur atoms include monocyclic heterocycles such as thiazole; condensed bicyclic heterocycles such as benzothiazole; and condensed tricyclic heterocycles such as phenothiazine.

The -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -Si(-)(-)-, the -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N(-)-, the -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N=, and the -CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -O-, -S-, -S(O) ₂ - or -CO-. Examples of such groups include:

_-SiH3 ;
silyl groups having 1 _to 3 hydrocarbon groups, such as --Si( _CH3 ) ₃ , --Si( _CH2CH3 ) ₃ , _and --Si( _CH3 ) ₂ ( _CH2CH3 );
a silyl group having ₁ to ₃ groups selected from at least one of a _hydroxy group _, an alkoxy group, and an aryloxy group, such as —Si( _OH ) ₃ , —Si(OCH ₃ ) ₃ , —Si(OCH 2 CH ₃ ) ₃ , —Si ₍ O(CH ₂ ) 2 CH 3 ) 3 , —SiH ₂ (OH), and —Si(CH 3 ) 2 (OCH ₃ );
Amino group;
N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diisopropylamino group, N-butylamino group, N,N-dibutylamino group, N-isobutylamino group, N,N-diisobutylamino group, N-sec-butylamino group, N,N-disec-butylamino group, N-tert-butylamino group, N,N
- an amino group having one or two hydrocarbon groups, such as a di-tert-butylamino group, an N-phenylamino group, an N,N-diphenylamino group, an N,N-ethylmethylamino group, an N,N-propylmethylamino group, an N,N-isopropylmethylamino group, an N,N-butylmethylamino group, an N,N-tert-butylmethylamino group, and an N,N-phenylmethylamino group;
oxy groups having a hydrocarbon group bonded thereto (alkoxy groups and aryloxy groups), such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a (2-ethyl)hexyloxy group, a phenyloxy group, an m-tolyloxy group, and a 3,4-xylyloxy group;
Oxiranyl group;
Formyl group;
Alkanoyl groups such as an acetyl group, a propanoyl group, a butanoyl group, a tert-butanoyl group, a pentanoyl group, a hexanoyl group, a (2-ethyl)hexanoyl group, and a benzoyl group;
an oxycarbonyl group having a hydrocarbon group bonded thereto, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group;
Mercapto group;
a mercapto group having a hydrocarbon group bonded thereto, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, a (2-ethylhexyl)thio group, a phenylthio group, or an o-tolylthio group;
Sulfamoyl group;
N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, N-ethylsulfamoyl group, N,N-diethylsulfamoyl group, N-propylsulfamoyl group, N,N-dipropylsulfamoyl group, N-isopropylsulfamoyl group, N,N-diisopropylsulfamoyl group, N-butylsulfamoyl group, N,N-dibutylsulfamoyl group, N-isobutylsulfamoyl group, N,N-diisobutylsulfamoyl group, N-sec-butylsulfamoyl group, N,N-disec-butylsulfamoyl group sulfamoyl groups having one or two hydrocarbon groups, such as amoyl group, N-tert-butylsulfamoyl group, N,N-di-tert-butylsulfamoyl group, N-phenylsulfamoyl group, N,N-diphenylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group and N,N-phenylmethylsulfamoyl group;
N-formylamino group;
N-alkanoylamino groups such as an N-acetylamino group, an N-propanoylamino group, an N-butanoylamino group, an N-2,2-dimethylpropanoylamino group, an N-pentanoylamino group, an N-hexanoylamino group, an N-(2-ethyl)hexanoylamino group, or an N-benzoylamino group;
Hydroxy group;
alkanoyloxy groups such as a formyloxy group, an acetoxy group, a propanoyloxy group, a butanoyloxy group, a 2,2-dimethylpropanoyloxy group, a pentanoyloxy group, a hexanoyloxy group, a (2-ethyl)hexanoyloxy group, or a benzoyloxy group;
sulfonyl groups substituted with a hydrocarbon group, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl)hexylsulfonyl group, a phenylsulfonyl group, and a p-tolylsulfonyl group;
Carbamoyl group;
N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-ethylcarbamoyl group, N,N-diethylcarbamoyl group, N-propylcarbamoyl group, N,N-dipropylcarbamoyl group, N-isopropylcarbamoyl group, N,N-diisopropylcarbamoyl group, N-butylcarbamoyl group, N,N-dibutylcarbamoyl group, N-isobutylcarbamoyl group, N,N-diisobutylcarbamoyl group, N-sec-butylcarbamoyl group, N,N-disec-butylcarbamoyl group , carbamoyl groups having one or two hydrocarbon groups, such as an N-tert-butylcarbamoyl group, an N,N-di-tert-butylcarbamoyl group, an N-phenylcarbamoyl group, an N,N-diphenylcarbamoyl group, an N,N-ethylmethylcarbamoyl group, an N,N-propylmethylcarbamoyl group, an N,N-isopropylmethylcarbamoyl group, an N,N-butylmethylcarbamoyl group, an N,N-tert-butylmethylcarbamoyl group, and an N,N-phenylmethylcarbamoyl group.

Furthermore, the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by halogen atoms, cyano groups, nitro groups, --SO ₃ M, --CO ₂ M or MM.

The electron donating group represented by ^R3 is a group that has the property of easily donating electrons to the bonding atom side compared to a hydrogen atom. Examples of the electron donating group include those that have a negative value as the substituent constant (σ _p ) of the Hammett rule. The σ _p value of the electron donating group can be, for example, the value described in Table 1 of C. Hansch et al., "A Survey of Hammett Substituent Constants and Resonance and Field Parameters", Chem. Rev., Vol.91, p.165-195 (1991).

The σ _p value of the electron donating group represented by R ³ is, for example, less than 0, preferably −0.10 or less, more preferably −0.20 or less, and may be −0.95 or more, preferably −0.80 or more, more preferably −0.60 or more.

Specific examples of the electron-donating group represented by R ³ include linear or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; cycloalkyl groups such as cyclopropyl, cyclobutyl, and cyclopentyl; alkenyl groups such as vinyl, allyl, and 1-propenyl; cycloalkenyl groups such as 1-cyclopentenyl and 1-cyclohexenyl; aryl groups such as phenyl; aralkyl groups such as benzyl and phenethyl; alkoxy groups such as methoxy, ethoxy, propoxy, and butoxy; aryloxy groups such as phenyloxy; hydroxy groups; amino groups; amino groups having one or two alkyl groups such as methylamino, ethylamino, n-propylamino, dimethylamino, and diethylamino; amino groups having one or two aryl groups such as phenylamino; and hydroxyamino groups.

The number of carbon atoms in the linear or branched alkyl group, alkoxy group, and alkyl group that may be contained in the amino group is preferably 1 to 20, more preferably 1 to 12, even more preferably 1 to 8, and particularly preferably 1 to 4.

The number of carbon atoms in the cycloalkyl group is preferably 3 or more and 20 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 8 or less.

The number of carbon atoms in the alkenyl group is preferably 2 to 20, more preferably 2 to 12, and even more preferably 2 to 8.

The number of carbon atoms in the cycloalkenyl group is preferably 4 to 20, more preferably 4 to 12, and even more preferably 4 to 8.

The number of carbon atoms in the aryl group, aryloxy group, and aryl group that the amino group may have is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6 to 10.

The number of carbon atoms in the aralkyl group is preferably 7 to 20, more preferably 7 to 12.

The electron-donating group represented by ^R3 is preferably a linear or branched alkyl group, an alkoxy group, a hydroxy group, an amino group, or an amino group having one or two alkyl groups, more preferably an alkoxy group, a hydroxy group, or an amino group, and particularly preferably an alkoxy group having 1 to 4 carbon atoms.

Examples of alkali metal atoms represented by M and MM include alkali metal atoms such as lithium, sodium and potassium atoms, with sodium and potassium atoms being preferred.

Metal atoms of the metal atoms that may have ligands represented by M and MM include metal atoms belonging to groups 2 to 15 of the periodic table of elements. More preferred metal atoms are Mg, Ca, Sr, Ba, Cd, Ni, Zn, Cu, Hg, Fe, Co, Sn, Pb, Mn, Al, Cr, Rh, Ir, Pd, Ti, Zr, Hf, Si, and Ge, even more preferred are Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Sn, Mn, Al, and Cr, and particularly preferred are Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Mn, Al, and Cr.

The ligand of the metal atom which may have a ligand is not particularly limited and may be, _for example, a halogen atom, NO, _NO3 , _SO4 , _CH3CO2 , OH, etc.
a ligand coordinated to the metal atom and a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or the like contained in the same ligand may be coordinated to the same metal atom,
A plurality of different ligands may be coordinated to the same metal atom,
An oligomer or a polymer may be formed.
When compound (I) contains a metal atom which may have a ligand, the ligand also includes compound (I) excluding the metal atom which may have a ligand.
Compound (I) also includes such oligomers or polymers.
However, the charge of compound (I) is zero.

Z ¹ to Z ⁴ may be the same or different, and are preferably the same. Z ¹ to Z ⁴ are
each independently preferably represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 40 carbon atoms,
More preferably, each independently represents a hydrogen atom, or a linear or branched alkyl group (hereinafter, sometimes simply referred to as "alkyl group");
It is more preferable that each independently represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms,
A hydrogen atom is particularly preferred.

N(Z ¹ ), (Z ² ), (Z ³ ), and (Z ⁴ ) represented by M and MM are, for example,
_NH4 ;
Groups in which three of Z ¹ to Z ⁴ are hydrogen atoms and one is an alkyl group, such as NH ₃ (CH ₂ CH ₃ ) and NH ₃ ((CH ₂ ) ₇ CH ₃ );
Groups in which two of Z ¹ to Z ⁴ are hydrogen atoms and two are alkyl groups, such as NH ₂ (CH ₃ ) ₂ and NH ₂ (CH ₂ CH ₃ ) ₂ ;
Groups in which one of Z ¹ to Z ⁴ is a hydrogen atom and three of them are alkyl groups, such as NH(CH ₃ ) ₃ and NH(CH ₂ CH ₃ ) ₃ ;
Groups in which all of Z ¹ to Z ⁴ are alkyl groups, such as N(CH ₃ ) ₄ and N(CH ₂ CH ₃ ) ₄ , and the like, and of these, NH ₄ is preferred.

M is preferably a hydrogen atom or an alkali metal atom, and more preferably a hydrogen atom, a sodium atom, or a potassium atom.

As MM, an alkali metal atom, Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, Ni which may have a ligand, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Sn which may have a ligand, Mn which may have a ligand, Al which may have a ligand, or Cr which may have a ligand are preferred.

It is preferable that R ¹ , R ² , R ⁴ , and R ⁵ are each independently a hydrogen atom, a halogen atom, or a monovalent hydrocarbon group having 1 to 40 carbon atoms, more preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 12 carbon atoms, and particularly preferably a hydrogen atom.

^R3 is preferably a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, an amino group, or an amino group having one or two alkyl groups, more preferably a halogen atom, an alkoxy group, a hydroxy group, or an amino group, and particularly preferably a chlorine atom, a fluorine atom, or an alkoxy group having 1 to 4 carbon atoms.

^Q1 and ^Q2 each independently represent a divalent hydrocarbon group or a divalent heterocyclic group. The divalent hydrocarbon group may be a group obtained by removing one hydrogen atom from the monovalent hydrocarbon group, and the divalent heterocyclic group may be a group obtained by removing one hydrogen atom directly bonded to a carbon atom or heteroatom from the monovalent heterocyclic group.

-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -Si(-)(-)-;
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -N=,
-CH ₂ - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by -O-, -S-, -S(O) ₂ - or -CO-;
The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced by halogen atoms, cyano groups, nitro groups, --SO ₃ M, --CO ₂ M or MM.

Q ¹ and Q ² may be the same or different, and are preferably the same.

It is preferable that Q ¹ and Q ² each independently represent any one of the groups represented by formula (QQ1) to formula (QQ19).

[In formulas (QQ1) to (QQ19),
R ^Q1 to R ^Q94 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms, or a carbon atom. represents a monovalent heterocyclic group having a number of 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -Si(-)(-)-;
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by -N=,
The -CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is -O-, -S-,
may be replaced by -S(O) _2- or -CO-;
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced by halogen atoms, cyano groups, nitro groups, --SO ₃ M, --CO ₂ M or MM.
R ^Q1 to R ^Q94 may each be bonded to one or more selected from R ^Q1 to R ^Q94 to form a ring.
M and MM have the same meanings as defined above.
* represents a bond.

Examples of halogen atoms include the same groups as those described above, and the preferred embodiments are also the same.

Examples of the monovalent hydrocarbon group having 1 to 40 carbon atoms and the monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ^{to R} include the same groups as the monovalent hydrocarbon group having 1 to 40 carbon atoms and the monovalent heterocyclic group having 1 to 40 carbon atoms described above, and preferred embodiments thereof are also the same.

M and MM have the same meanings as above, and the preferred embodiments are also the same.

R ^Q1 to R ^Q94 are:
Each of them is preferably independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, CO ₂ M, or a monovalent hydrocarbon group having 1 to 40 carbon atoms;
More preferably, each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 12 carbon atoms,
It is even more preferable that each independently be a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, an ethyl group, or a propyl group;
A hydrogen atom is most preferred.

^Q1 and ^Q2 are
It is more preferable that each of them is independently any one of groups represented by formula (QQ1) to formula (QQ12),
More preferably, each of them is independently any one of groups represented by formula (QQ1) to formula (QQ5),
It is even more preferable that each of them is independently a group represented by formula (QQ1) or formula (QQ2),
In a most preferred embodiment, Q ¹ and Q ² are groups represented by formula (QQ2).

Examples of compound (I) include compounds represented by formulae (Ia1) to (Ia200) shown in Tables 1 and 2 below.

In Tables 1 and 2, Qa1 to Qa5 represent groups represented by the following formulas (* indicates a bond).

As compound (I), compounds represented by formulas (Ia1) to (Ia48) and (Ia73) to (Ia80) are preferred, compounds represented by formulas (Ia1) to (Ia16), (Ia41) to (Ia48) and (Ia73) to (Ia80) are more preferred, and compounds represented by formulas (Ia1) to (Ia16) are even more preferred.

Compound (I) can be produced, for example, by reacting a compound represented by formula (pt1) with a compound represented by formula (pt2) and a compound represented by formula (pt3). Hereinafter, this production method may be referred to as Production Method 1.

In formulae (pt1) to (pt3), R ¹ to R ⁵ , Q ¹ and Q ² have the same meanings as defined above.

In the reaction of Production Method 1, the amount of the compound represented by formula (pt2) used is usually 0.1 to 30 moles, preferably 1 to 20 moles, more preferably 1 to 16 moles, and even more preferably 1 to 10 moles, per mole of the compound represented by formula (pt1).

In the reaction of Production Method 1, the amount of the compound represented by formula (pt3) used is usually 0.1 to 30 moles, preferably 1 to 20 moles, more preferably 1 to 16 moles, and even more preferably 1 to 10 moles, per mole of the compound represented by formula (pt1).

The reaction temperature is usually -100 to 300°C, preferably 0 to 280°C, more preferably 50 to 250°C, even more preferably 100 to 230°C, and particularly preferably 150 to 200°C.

The reaction time is usually 0.5 to 500 hours.

The reaction in Production Method 1 is usually carried out in the presence of a solvent.

Solvents include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; toluene and trimethylbenzene Examples of suitable solvents include aromatic hydrocarbon solvents such as 1,3,5-trimethylbenzene, decalin, and tetralin; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide, with methyl benzoate being preferred.

The amount of the solvent used is usually 1 to 1000 parts by mass per part by mass of the compound represented by formula (pt1) in the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2) and the compound represented by formula (pt3).

In the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2) and the compound represented by formula (pt3), it is preferable that an acid coexist.

Examples of acids include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid, and tartaric acid; and the like. Of these, hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acids are preferred, carboxylic acids are more preferred, and benzoic acid is even more preferred.

The amount of acid used in the reaction of Production Method 1 is usually 1 to 90 moles, preferably 1 to 70 moles, more preferably 1 to 50 moles, and even more preferably 1 to 30 moles, per mole of the compound represented by formula (pt1).

The method for isolating compound (I) from the reaction mixture is not particularly limited, and it can be isolated by various known methods.
For example, after the reaction is completed, the compound (I) in the reaction mixture may be difficult to dissolve, but the compound other than the compound (I) is easily dissolved in a solvent such as methanol, and the reaction mixture is thoroughly mixed and then filtered to obtain the compound (I). Furthermore, the residue obtained may be washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/or an acidic aqueous solution such as hydrochloric acid, and then washed with water, a low-boiling alcohol such as methanol, or a mixed solvent thereof to obtain the compound (I). Furthermore, the compound may be purified by column chromatography and/or recrystallization, etc.
Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the resulting residue may be purified by column chromatography and/or recrystallization, or
After completion of the reaction, the reaction mixture may be purified by column chromatography and/or recrystallization.

The compound represented by formula (I) can be produced by reacting a compound represented by formula (pt1) with a compound represented by formula (pt2) to produce a compound represented by formula (I') (hereinafter, sometimes referred to as compound (I')), followed by:
Compound (I') is hydrolyzed in the presence of a base to produce a compound represented by formula (IM1) (hereinafter, sometimes referred to as compound (IM1)), and further
It can be produced by reacting compound (IM1) with a compound represented by formula (pt3).

In the formulae (pt1), (pt2), (pt3), (I') and (IM1), ^R1 to ^R5 , ^Q1 and ^Q2 have the same meanings as defined above.

In the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2), the amount of the compound represented by formula (pt2) used is usually 0.1 to 60 moles, preferably 1 to 40 moles, more preferably 1 to 32 moles, and even more preferably 2 to 20 moles, per mole of the compound represented by formula (pt1).

In the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt3) used is usually 0.1 to 30 moles, preferably 1 to 20 moles, more preferably 1 to 16 moles, and even more preferably 1 to 10 moles, per mole of the compound represented by formula (IM1).

The reaction temperature and reaction time in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), and the reaction temperature and reaction time in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) are the same as the reaction temperature and reaction time in production method 1, and the preferred aspects thereof are also the same.

The reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), and the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) are usually carried out in the presence of a solvent. Examples of the solvent include the solvents exemplified in Production Method 1, and the same applies to the preferred embodiments.

The amount of solvent used in the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2) is usually 1 to 1,000 parts by mass per part by mass of the compound represented by formula (pt1).

The amount of solvent used in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is usually 1 to 1,000 parts by mass per part by mass of the compound represented by formula (IM1).

In the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), and in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3), it is preferable that an acid coexist. Examples of the acid include the acids exemplified in Production Method 1, and the preferred embodiments are the same.

The amount of acid used in the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2) is usually 1 to 90 moles, preferably 1 to 70 moles, more preferably 1 to 50 moles, and even more preferably 1 to 30 moles, per mole of the compound represented by formula (pt1).

The amount of acid used in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is usually 1 to 90 moles, preferably 1 to 70 moles, more preferably 1 to 50 moles, and even more preferably 1 to 30 moles, per mole of the compound represented by formula (IM1).

The method for extracting the compound represented by formula (I') from the reaction mixture in the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2), and the method for extracting the compound represented by formula (I) from the reaction mixture in the reaction of the compound represented by formula (IM1) with the compound represented by formula (pt3) are not particularly limited, and the compound can be extracted by various known methods, such as the method exemplified in Production Method 1.

Examples of bases that can be used in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5.4.0]undec-7-ene, and 1,5-diazabicyclo[4.3.0]non-5-ene; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organometallic compounds such as methyllithium, butyllithium, tert-butyllithium, and phenyllithium; and inorganic bases such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, and potassium hydroxide. Inorganic bases are preferred, and potassium hydroxide is particularly preferred.

The amount of base used in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 0.1 to 100 moles, preferably 1 to 70 moles, and more preferably 2 to 40 moles, per mole of the compound represented by formula (I').

The amount of water used in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 1 to 1000 parts by mass, preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, and even more preferably 1 to 50 parts by mass, per part by mass of the compound represented by formula (I').

The reaction temperature in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 0 to 100°C, preferably 5 to 100°C, more preferably 20 to 100°C, even more preferably 40 to 100°C, and particularly preferably 60 to 100°C.

The reaction time for the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is preferably continued until disappearance of the compound represented by formula (I') is confirmed, and is usually 0.5 to 120 hours, preferably 1 to 72 hours, and more preferably 1 to 24 hours.

The method for extracting the compound represented by formula (IM1) from the reaction mixture in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is not particularly limited, and the compound can be extracted by various known methods, such as the method exemplified in Production Method 1.

A coloring composition containing compound (I) can produce a darker color filter.

[Coloring composition]
The coloring composition of the present invention contains the compound (I) and a red coloring material. The compound (I) and the red coloring material can be used as a colorant (hereinafter, sometimes referred to as colorant (A)).
The coloring composition of the present invention may contain at least one selected from a resin (hereinafter sometimes referred to as resin (B)), a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)), a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)), a solvent (hereinafter sometimes referred to as solvent (E)), and a leveling agent (hereinafter sometimes referred to as leveling agent (F)). It is more preferable to contain at least one selected from a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E), and it is even more preferable to contain at least one selected from a resin (B), a polymerizable compound (C), and a polymerization initiator (D). In addition, when the coloring composition contains a polymerizable compound (C), it is preferable to also contain a polymerization initiator (D).
In this specification, the compounds exemplified as each component may be used alone or in combination, unless otherwise specified.

[Colorant (A)]
The colorant (A) contains the compound (I) and a red colorant. The colorant (A) contains the compound (I) and a red colorant, so that a color filter having good heat resistance can be obtained. In addition, the compound (I) can have a maximum absorption on the longer wavelength side (for example, around 500 nm) compared with conventional yellow colorants, so that when the compound (I) is combined with a red colorant to form a red color filter, the color filter can be made thin and dark in color, which is preferable.

[[Compound (I)]]
Compound (I) is a compound represented by the above formula (I), and preferred embodiments thereof are also the same.

The content of compound (I) is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, and is preferably 50% by mass or less, more preferably 30% by mass or less, even more preferably 20% by mass or less, and particularly preferably 15% by mass or less, based on the total amount of colorant (A). When the content of compound (I) is within the above range, the heat resistance of the color filter when made into a color filter is good.

[Red color material]
The red coloring material may be a red dye or a red pigment, but is preferably a red pigment.

As the red dye, known red dyes can be used, and examples thereof include known red dyes described in the Color Index (published by The Society of Dyers and Colourists) and Dyeing Notes (Shikisensha).
C.I. Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
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, 18 2, 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. 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. Basic Red 1, 9, 10;
C.I. Reactive Red 36;
C.I. Modant Red 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; and the like.

As a red dye, Lumogen (registered trademark) F Red 305 (manufactured by BASF), a product of BASF, may be used.

As the red pigment, known red pigments can be used, for example, red pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Specific examples include C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, 291, etc., and among them, at least one red pigment selected from C.I. Pigment Red 177, 254, and 291 is preferable, and at least one red pigment selected from C.I. Pigment Red 177 and 291 is particularly preferable.

The content of the red colorant is preferably 50% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more, based on the total amount of colorant (A), and is preferably 99% by mass or less, and more preferably 95% by mass or less.

The total amount of compound (I) and the red colorant is preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, particularly preferably 95% by mass or more, based on the total amount of colorant (A), and may be 100% by mass.

By dispersing compound (I) in a solvent containing a dispersant, a dispersion liquid in which compound (I) is more uniformly dispersed in the solution can be obtained.

The content of compound (I) in the dispersion is preferably 1% by mass or more, more preferably 3% by mass or more, and is preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less.

The solvent may be any of the solvents listed below as solvent (E).

Examples of the dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. Examples of the dispersant include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Lubrizol Corporation), EFKA (manufactured by CIBA Corporation), AJISPER (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (manufactured by BYK), and BYK (manufactured by BYK).

When a dispersant is used, the amount used is preferably 0.1 parts by mass or more and 5 parts by mass or less, and more preferably 0.5 parts by mass or more and 2.5 parts by mass or less, per part by mass of compound (I). When the amount of the dispersant used is within the above range, a dispersion in a uniformly dispersed state tends to be obtained.

[[Colorant (A1)]]
The colorant (A) may contain a colorant other than the compound (I) and the red colorant (sometimes referred to as colorant (A1)).

The colorant (A1) may be a dye or a pigment, so long as it is a colorant other than compound (I) and a red colorant. As the dye, known dyes can be used, for example, known dyes described in Color Index (published by The Society of Dyers and Colourists) and Dyeing Notes (Shikisensha). In addition, according to the chemical structure, examples of known dyes include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes, etc.

Specifically, dyes having the following Color Index (C.I.) numbers are included.
C.I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;
C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;
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, 38, 44, 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. Solvent dyes such as C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35,
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, 1 57,160,161,163,168,169,172,177,178,179,184,190,193,196,197,199,202,203,204,205,207,212,214,220,221,228,230,232,235,238,24 0, 242, 243, 251;
C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 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, 126,127,129,130,131,138,140,142,143,147,150,151,154,158,161,166,167,168,170,171,175,182,183,184,187,192,199,203,204,205,2 10, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;
C.I. Acid dyes such as 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, 104, 105, 106, 109,
C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C.I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 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 dyes such as C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82,
C.I. Disperse Yellow 51, 54, 76;
C.I. Disperse Violet 26, 27;
C.I. Disperse dyes such as C.I. Disperse Blue 1, 14, 56, 60, etc.
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 dyes such as C.I. Basic Green 1;
C.I. Reactive Yellow 2, 76, 116;
C.I. Reactive dyes such as C.I. Reactive Orange 16;
C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
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. Mordant dyes such as C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53,
Examples include C.I. Vat dyes such as C.I. Vat Green 1.

Further examples include Lumogen®, a product of BASF, such as Lumogen® F Yellow 083 (manufactured by BASF), Lumogen® F Yellow 170 (manufactured by BASF), and Lumogen® F Orange 240 (manufactured by BASF).

Further examples include a compound represented by formula (z) and a compound represented by formula (z1).

As the pigment, any known pigment can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).
Specifically, yellow pigments such as C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231;
Orange pigments such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
blue pigments such as C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60;
Violet pigments such as C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38;
green pigments such as C.I. Pigment Green 7, 36, 58, 59, 62, 63;
Brown pigments such as C.I. Pigment Brown 23 and 25;
Black pigments such as C.I. Pigment Black 1, 7, 31, and 32: and the like.

The pigment may be subjected, as necessary, to a rosin treatment, a surface treatment using a pigment derivative into which an acidic group or a basic group has been introduced, or the like, a grafting treatment onto the pigment surface using a polymer compound or the like, a particle size reduction treatment using a sulfuric acid atomization method or the like, a washing treatment using an organic solvent or water for removing impurities, a removal treatment of ionic impurities using an ion exchange method or the like, or the like.
The pigment preferably has a uniform particle size. By carrying out a dispersion treatment in the presence of a dispersant, it is possible to obtain a dispersion in which the pigment is more uniformly dispersed in the solution.

The dispersant may be any of those described above.

When a dispersant is used, the amount used is preferably 0.1 parts by weight to 5 parts by weight, and more preferably 0.2 parts by weight to 2.5 parts by weight, per 1 part by weight of pigment. When the amount of dispersant used is within the above range, a dispersion in a uniformly dispersed state tends to be obtained.

The content of colorant (A) is preferably 5% by mass or more and 60% by mass or less, more preferably 8% by mass or more and 55% by mass or less, and even more preferably 10% by mass or more and 50% by mass or less, based on the total amount of solids in the coloring composition. When the content of colorant (A) is within the above range, the color density when made into a color filter is sufficient, and the composition can contain the necessary amounts of resin (B) and polymerizable compound (C), so that a pattern with sufficient mechanical strength can be formed.

In this specification, the "total amount of solids" refers to the total amount of the coloring composition excluding the solvent content. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

[Resin (B)]
Resin (B) is preferably an alkali-soluble resin, and more preferably a polymer having a structural unit derived from at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "monomer (a)").
Resin (B) is preferably a copolymer having, in addition to the structural unit derived from monomer (a), a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b)"), and/or other structural units.
Examples of the other structural unit include a structural unit derived from a monomer copolymerizable with the monomer (a) (however, different from the monomer (a) and the monomer (b). Hereinafter, this may be referred to as "monomer (c)"), a structural unit having an ethylenically unsaturated bond, and the like.

In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid;
Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid;
Bicyclounsaturated compounds containing a carboxy group, such as 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]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;
Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;
Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate;
Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid;
etc.

Among these, acrylic acid, methacrylic acid, o-, m-, and p-vinylbenzoic acid, maleic anhydride, and the like are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in an alkaline aqueous solution.

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

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

Examples of monomer (b1) include a monomer having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter, sometimes referred to as "monomer (b1-1)") and a monomer having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter, sometimes referred to as "monomer (b1-2)").

The monomer (b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond.
Examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl)ether, Examples of such styrene include 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, and 2,4,6-tris(glycidyloxymethyl)styrene.

Examples of monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) M100; manufactured by Daicel Corporation), compounds represented by formula (BI) and compounds represented by formula (BII).

In formula (BI) and formula (BII), R ^a and R ^b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a hydroxy group.
X ^a and X ^b each independently represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S- or *-R ^c -NH-.
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* represents a bond to O.

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

Examples of alkyl groups in which hydrogen atoms are replaced with hydroxy include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, and 4-hydroxybutyl groups.

R ^a and R ^b are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

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

X ^a and X ^b 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 CH ₂ --O-- (* represents a bond to O).

Examples of compounds represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among them, compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9) and (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9) and (BI-15) are more preferred.

Examples of compounds represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15), and among these, preferred are compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15), and more preferred are compounds represented by formulas (BII-1), (BII-7), (BII-9), and (BII-15).

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more kinds. The compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio thereof [compound represented by formula (BI): compound represented by formula (BII)] is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20 on a molar basis.

As the monomer (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable.
Examples of the monomer (b2) include 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 3-ethyl-3-acryloyloxyethyloxetane.

As the monomer (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

As the monomer (b), the monomer (b1) is preferable in that it can further increase the reliability of the heat resistance, chemical resistance, etc. of the obtained color filter. Furthermore, the monomer (b1-2) is more preferable in that the storage stability of the colored composition is excellent.

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decene-8-yl (meth)acrylate,
(meth)acrylic acid esters such as acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;
Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;
Halogen atom-containing (meth)acrylic acid esters such as 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate;
dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and 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, chloro[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 bicyclounsaturated compounds such as 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 and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;
dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide;
Examples of the vinyl group-containing aromatic compounds include styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; and dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene.

Among these, from the viewpoints of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-9-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decene-8-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decene-9-yl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, phenyl (meth)acrylate, 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate, 9-vinylcarbazole, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate are preferred.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl(meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/benzyl(meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/9-vinylcarbazole/(meth)acrylic acid copolymer, and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/
Phenyl (meth)acrylate/o-vinyl benzoic acid copolymer, 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ] Decyl (meth)acrylate/phenyl (meth)acrylate/m-vinyl benzoic acid copolymer, 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]
Decyl (meth)acrylate/phenyl (meth)acrylate/p-vinyl benzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/phenyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/2,2,3,3,4,4,
5,5-Octafluoropentyl (meth)acrylate/(meth)acrylic acid copolymer, 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 (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] decyl (meth)acrylate/(meth)acrylic acid/vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic acid / 2-ethylhexyl (meth) acrylate copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / tricyclo [5.2.1.0 ^2,6 ] decenyl (meth) acrylate / (meth)
Examples of the resins include acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer, and resins described in JP-A-9-106071, JP-A-2004-29518, and JP-A-2004-361455.

Among these, the resin (B) is preferably a copolymer containing structural units derived from monomer (a) and structural units derived from monomer (b).

Resin (B) may be a combination of two or more kinds. In this case, resin (B) is at least
It is preferable that the composition contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b),
It is more preferable that the copolymer contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1),
It is more preferable that the copolymer contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1-2),
Particularly preferred is one or more selected from 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyl toluene copolymer, and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer.

The polystyrene-equivalent weight average molecular weight of resin (B) is preferably 3,000 or more and 100,000 or less, more preferably 5,000 or more and 50,000 or less, and even more preferably 5,000 or more and 30,000 or less. 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 parts in the developer is good, and the resolution of the colored pattern tends to be improved.

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

In terms of solid content, it is preferably 50 mg-KOH/g or more and 170 mg-KOH/g or less, more preferably 60 mg-KOH/g or more and 160 mg-KOH/g or less, and even more preferably 70 mg-KOH/g or more and 150 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 with an aqueous potassium hydroxide solution.

The content of resin (B) is preferably 7% by mass or more and 65% by mass or less, more preferably 13% by mass or more and 60% by mass or less, and even more preferably 17% by mass or more and 55% by mass or less, based on the total amount of solids. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and remaining film rate of the colored pattern tend to be improved.

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

Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the above-mentioned monomers (a), (b), and (c).

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

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more 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, ethyl Examples of the dipentaerythritol hexa(meth)acrylate include ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate, and caprolactone modified dipentaerythritol hexa(meth)acrylate, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

The content of the polymerizable compound (C) is preferably 5% by mass or more and 65% by mass or less, more preferably 7% by mass or more and 60% by mass or less, even more preferably 8% by mass or more and 55% by mass or less, and particularly preferably 10% by mass or more and 40% by mass or less, based on the total amount of solids in the coloring composition. When the content of the polymerizable compound (C) is within the above range, the residual film rate during color pattern formation and the chemical resistance of the color filter tend to be improved.

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

Examples of O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1- [9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine are mentioned. In addition, as the O-acyloxime compound, commercially available products such as PBG-327 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), Irgacure OXE01, OXE02 (both manufactured by BASF), and N-1919 (manufactured by ADEKA Corporation) may be used. Among them, the O-acyloxime compound is preferably at least one selected from the group consisting of N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and more preferably at least one selected from the group consisting of N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercially available alkylphenone compounds such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used.
Alkylphenone compounds also include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.

Examples of biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, phenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).

Examples of the triazine compounds 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, and 2,4-bis(trichloromethyl)-6-(4
-Methoxystyryl)-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 and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

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

Further examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.
These are preferably used in combination with a polymerization initiator aid. Examples of the polymerization initiator aid include amine compounds such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.), alkoxyanthracene compounds such as 9,10-dimethoxyanthracene and 2-ethyl-9,10-dimethoxyanthracene, thioxanthone compounds such as 2-isopropylthioxanthone, 4-isopropylthioxanthone and 2,4-diethylthioxanthone, and carboxylic acid compounds such as phenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid and methoxyphenylsulfanylacetic acid.

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 oxime compound, and a biimidazole compound, more preferably a polymerization initiator containing an oxime compound, and even more preferably a polymerization initiator containing an O-acyloxime compound.

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 1 part by mass or more and 25 parts by mass or less, and even more preferably 3 parts by mass or more and 25 parts by mass or less, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). 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, thereby improving the productivity of the color filter.

[Solvent (E)]
The solvent (E) is not particularly limited, and any solvent commonly used in the relevant field can be used.
Examples of the solvent (E) include ester solvents (solvents containing -CO-O- but not -O- in the molecule), ether solvents (solvents containing -O- but not -CO-O- in the molecule), ether ester solvents (solvents containing -CO-O- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -CO-O- in the molecule), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO- and -CO-O-), aromatic hydrocarbon solvents, amide solvents and dimethyl sulfoxide.

Examples of 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.

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 ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2-ethoxy-2-methylpropionate, Examples of such ether acetates include ethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

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

Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

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

Among the above solvents, from the viewpoint of coatability and drying property, organic solvents having a boiling point of 120°C or more and 180°C or less at 1 atm are preferred. Preferred examples of the solvent 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, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide, and more preferred examples include propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone.

The content of the solvent (E) is preferably 70% by mass or more and 95% by mass or less, more preferably 75% by mass or more and 92% by mass or less, based on the total amount of the coloring composition of the present invention. In other words, the total content of the solid content of the coloring composition is preferably 5% by mass or more and 30% by mass or less, more preferably 8% by mass or more and 25% by mass or less. When the content of the solvent (E) is within the above range, the flatness during application is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics tend to be good.

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

Examples of silicone surfactants include surfactants having a siloxane bond in the molecule. Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (product names: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and 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 fluorosurfactants include surfactants having a fluorocarbon chain in the molecule. Specific examples include Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), EF-TOP (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemicals Research Institute, Ltd.).

Examples of silicone surfactants having fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in the molecule. Specific examples include Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

When the leveling agent (F) is contained, its content 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 or less, and even more preferably 0.01% by mass or more and 0.05% by mass or less, based on the total amount of the coloring composition. Note that this content does not include the content of the dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[Other ingredients]
The colored composition of the present invention may contain additives known in the art, such as a polymerization initiator aid, a filler, another polymer compound, an adhesion promoter, a light stabilizer, and a chain transfer agent, as necessary.

[Method of producing colored composition]
The colored composition of the present invention can be prepared, for example, by mixing the compound (I) and the colorant (A) containing a red coloring material, and the resin (B), polymerizable compound (C), polymerization initiator (D), solvent (E), leveling agent (F) and other components used as necessary. The mixing can be performed using known or conventional devices and conditions.

The colorant (A) may be mixed in advance with a part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle size is about 0.2 μm or less. In this case, the dispersant and/or the resin (B) may be mixed in part or all as necessary. The remaining components are preferably mixed with the dispersion thus obtained to a predetermined concentration to prepare the desired coloring composition. When using a bead mill, the diameter of the beads is preferably 0.05 mm or more and 0.5 mm or less, and the material of the beads may be glass, ceramic, metal, or the like.

[Color filter]
Examples of methods for producing a colored pattern of a color filter from the colored composition of the present invention include a photolithography method, an inkjet method, a printing method, and the like. Among these, the photolithography method is preferred. The photolithography method is a method in which the colored composition is applied to a substrate, dried to form a composition layer, and the composition layer is exposed through a photomask and developed. In the photolithography method, a colored coating film, which is a cured product of the composition layer, can be formed by not using a photomask during exposure and/or not developing.

The thickness of the color filter (cured film) is, for example, 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and more preferably 0.5 μm or more and 6 μm or less.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass with a silica-coated surface, resin plates such as polycarbonate, polymethylmethacrylate, and polyethylene terephthalate, silicon, and the above substrates on which aluminum, silver, and silver/copper/palladium alloy thin films are formed may be used. On these substrates, other color filter layers, resin layers, transistors, circuits, and the like may be formed. A silicon substrate that has been subjected to HMDS treatment may also be used.

The 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, the coloring composition is applied onto a substrate, and volatile components such as the solvent are removed by heating and drying (pre-baking) and/or drying under reduced pressure to obtain a smooth composition layer. Examples of application methods include spin coating, slit coating, and slit and spin coating. The temperature when drying by heating is preferably 30°C or higher and 120°C or lower, and more preferably 50°C or higher and 110°C or lower. The heating time is preferably 10 seconds or higher and 60 minutes or lower, and more preferably 30 seconds or higher and 30 minutes or lower. When drying under reduced pressure, it is preferably performed under a pressure of 50 to 150 Pa and at a temperature range of 20 to 25°C. The film thickness of the composition layer is not particularly limited and may be appropriately selected according to the film thickness of the desired 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 according to 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 less than 350 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. It is preferable to use a reduced projection exposure device or a proximity exposure device such as a mask aligner and a stepper, since it is possible to uniformly irradiate the entire exposure surface with parallel light rays and to accurately align the photomask and the substrate.

The composition layer after exposure is brought into contact with a developer and developed to form a colored pattern on the substrate. The unexposed portion of the composition layer is dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. 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 development method may be any of a paddle method, a dipping method, and a spray method. Furthermore, the substrate may be tilted at any angle during development.
After development, it is preferable to wash with water.

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

The colored patterns and colored coating films thus obtained are useful as color filters, which are useful as color filters for use in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc.

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

In the following synthesis examples, the structures of the compounds were confirmed by mass spectrometry (LC: Agilent 1200 model, MASS: Agilent LC/MSD6130 model).

[Example 1]
4-amino-6-fluoro-2-methylquinoline (Sigma-Aldrich Japan, LLC) 1 mol,
2,3-naphthalenedicarboxylic anhydride (Tokyo Chemical Industry Co., Ltd.) 8 moles,
21 moles of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 73 times the weight of 1 mole of 4-amino-6-fluoro-2-methylquinoline, of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.)
were mixed.
The mixture was stirred for 120 hours while being maintained at 170°C.
The mixture was cooled to room temperature, and to the mixture was added methanol in an amount 13 times the weight of the mixture.
The resulting mixture was stirred at room temperature and then filtered.
The resulting residue was washed with methanol.
The resulting residue was purified by column chromatography to obtain the compound represented by formula (I-1).

<Identification of the compound represented by formula (I-1)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 537
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 535
Exact Mass: 536

[Example 2]
4-amino-6-methoxy-2-methylquinoline (Sigma-Aldrich Japan, LLC) 1 mol,
2,3-naphthalenedicarboxylic anhydride (Tokyo Chemical Industry Co., Ltd.) 8 moles,
21 moles of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 73 times the weight of 1 mole of 4-amino-6-methoxy-2-methylquinoline, of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.)
were mixed.
The mixture was stirred for 120 hours while being maintained at 170°C.
The mixture was cooled to room temperature, and to the mixture was added methanol in an amount 13 times the weight of the mixture.
The resulting mixture was stirred at room temperature and then filtered.
The resulting residue was washed with methanol.
The resulting residue was purified by column chromatography to obtain the compound represented by formula (I-2).

<Identification of the compound represented by formula (I-2)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 549
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 547
Exact Mass: 548

(Example of dye synthesis)
The following compound (I-3) was synthesized according to the method described in JP-A-2002-179979.

(Resin Synthesis Example 1)
A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C while stirring. Next, a mixed solution of 38 parts of acrylic acid, 289 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-yl acrylate (content ratio: 1:1 by 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 kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (Resin B-1) solution having a solid content of 35.1% and a viscosity of 125 mPas measured with a Brookfield viscometer (23°C). The weight average molecular weight Mw of the produced copolymer was 9.2 x 10 ³ , the dispersity was 2.08, and the acid value calculated as solid content was 77 mg-KOH/g. Resin B-1 has the following structural units.

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions.
Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG2000HXL
Column temperature: 40°C
Solvent: THF
Flow rate: 1.0mL/min
Test liquid solid content concentration: 0.001 to 0.01% by mass
Injection volume: 50 μL
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 the number average molecular weight (Mw/Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

(Colored dispersion preparation example 1)
[Preparation of Colored Dispersion (P-1)]
The compound represented by formula (I-2), the compound represented by formula (I-3), the dispersant, the resin B-1, and the solvent E-1 were added so as to obtain the composition shown in Table 3, and the mixture was mixed with zirconia beads. The mixture was shaken and the zirconia beads were removed by filtration to prepare a colored dispersion (P-1).

(Colored dispersion preparation example 2)
[Preparation of Colored Dispersion (P-2)]
C.I. Pigment Yellow 185, the compound represented by formula (I-3), the dispersant, the resin B-1, and the solvent E-1 were added so as to obtain the composition shown in Table 3, and zirconia beads were added and the mixture was shaken. The zirconia beads were then removed by filtration to prepare a colored dispersion (P-2).

In Table 3, each component represents the following compound.
Compound (I-2): Compound represented by formula (I-2) PY185: C.I. Pigment Yellow 185
Compound (I-3): Compound represented by formula (I-3) Dispersant (solid content): BYK-LP N 6919 (manufactured by BYK Corporation)
Resin (B-1) (solid content): Resin B-1
Solvent (E-1): Propylene glycol monomethyl ether acetate Zirconia beads: diameter 0.1 mm

(Colored dispersion preparation example 3)
[Preparation of Colored Dispersion (P-3)]
The components were mixed in the following ratio to obtain a colored dispersion (P-3).
C. I. Pigment Red 291 12.0%
Dispersant (solid content) 3.5%
Resin (solid content): 5.0%
Propylene glycol monomethyl ether acetate 79.5%

(Colored dispersion preparation example 4)
[Preparation of Colored Dispersion (P-4)]
The components were mixed in the following ratio to obtain a colored dispersion (P-4).
C. I. Pigment Red 177 13.0%
Dispersant (solids) 4.6%
Resin (solid content) 4.6%
Propylene glycol monomethyl ether acetate 77.8%

[Example 3, Comparative Example 1]
(Preparation of Coloring Composition)
The components were mixed so as to obtain the compositions shown in Table 4.

In Table 4, each component represents the following compound.
Resin (B-1): Resin B-1 (solid content)
Polymerizable compound (C-1): Dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)
Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine (PBG-327; oxime compound; manufactured by Changzhou Strong Electronic New Materials Co., Ltd.)
Solvent (E-1): Propylene glycol monomethyl ether acetate Solvent (E-2): Diacetone alcohol Leveling agent (F-1): Polyether modified silicone oil (solid content) ("Toray Silicone SH8400" manufactured by Toray Dow Corning Co., Ltd.)

(Production of color filters (colored coatings))
The colored composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; Corning Incorporated), and then prebaked at 100°C for 3 minutes to form a colored composition layer. After cooling, the colored composition layer formed on the substrate was irradiated with light at an exposure dose of 100 mJ/ ^cm2 (based on 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; Topcon Corporation). After the light irradiation, post-baking was performed in an oven at 230°C for 30 minutes to obtain a colored coating film.

(Color change evaluation)
The obtained thin film on the glass substrate was subjected to spectral measurement using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) and Y in the CIE XYZ color system were measured using the color matching function of C light source. The measurement results of the xy chromaticity coordinates are shown in Table 5. Then, additional baking was performed in an oven at 230° C. for 120 minutes. After the additional baking, the xy chromaticity coordinates and Y were measured again, and the color difference ΔEab ^* before and after heating was calculated from the measured values by the method described in JIS Z 8730:2009 (7. Calculation method of color difference). The results are shown in Table 5. The smaller the color difference ΔEab ^* , the smaller the color change.

The compound and colored composition of the present invention can provide a color filter with improved heat resistance, and the color filter formed from the compound and colored composition of the present invention is useful as a color filter for use in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices.

Claims (6)

A compound represented by formula (I).

[In formula (I),
R ¹ , R ² , R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 12 carbon atoms .
^R3 represents a halogen atom or an alkoxy group having 1 to 4 carbon atoms .
^Q1 and ^Q2 each independently represent a group represented by formula (QQ1) or formula (QQ2) .

[In formula (QQ1) to formula (QQ2),
R ^Q1 to R ^Q10 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 12 carbon atoms.
* represents a bond. A coloring composition comprising the compound according to claim 1 and a red colorant. The coloring composition according to claim 2 , further comprising a resin. The colored composition according to claim 2 or 3 , further comprising a polymerizable compound and a polymerization initiator. A color filter formed from the coloring composition according to any one of claims 2 to 4 . A display device comprising the color filter according to claim 5 .