JP7441134B2 - Colored curable resin composition, color filter and display device - Google Patents

Description

The present invention relates to a colored curable resin composition, a color filter, and a display device.

Colored resin compositions are used to manufacture color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays. As a colored resin composition, a composition containing a quinophthalone compound represented by the following formula (x) is known (Patent Document 1).

Japanese Patent Application Publication No. 2003-167112

However, color filters formed from the conventionally known colored resin compositions containing the above-mentioned quinophthalone compounds sometimes have insufficient light resistance. Therefore, an object of the present invention is to provide a colored curable resin composition that can form a color filter with excellent light resistance.

［式中、
Ｒ¹～Ｒ⁶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。
Ｒ¹及びＲ²、Ｒ²及びＲ³、Ｒ³及びＲ⁴、Ｒ⁴及びＲ⁶、及びＲ⁶及びＲ⁵は、それぞれ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］ 前記一重項酸素クエンチャーが遷移金属錯体である［１］に記載の着色硬化性樹脂組成物。
［３］ 前記一重項酸素クエンチャーがニッケル錯体、銅錯体及びコバルト錯体から選ばれる少なくとも１種を含む遷移金属錯体である［２］に記載の着色硬化性樹脂組成物。
［４］ 前記式（Ｉ）又は式（ＩＩ）におけるＱ¹及びＱ²が、それぞれ独立して、式（ＱＱ１）又は式（ＱＱ２）で表される基である［１］～［３］のいずれかに記載の着色硬化性樹脂組成物。

［式中、
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。］
［５］ 前記式（Ｉ）又は式（ＩＩ）におけるＱ¹及びＱ²の少なくとも一方が、式（ＱＱ１）で表される基である［４］に記載の着色硬化性樹脂組成物。
［６］ 前記着色剤が式（Ｉ）で表される化合物を含む［１］～［５］のいずれかに記載の着色硬化性樹脂組成物。
［７］ 前記式（Ｉ）におけるＱ¹又はＱ²が、少なくとも１つの－ＣＯ₂Ｈを有する［６］に記載の着色硬化性樹脂組成物。
［８］ ［１］～［７］のいずれかに記載の着色硬化性樹脂組成物から形成されるカラーフィルタ。
［９］ ［８］に記載のカラーフィルタを含む表示装置。 The gist of the invention is as follows.
[1] Contains a colorant, a resin, a polymerizable compound, a polymerization initiator, and a singlet oxygen quencher, and the colorant is selected from a compound represented by formula (I) and a compound represented by formula (II). A colored curable resin composition containing at least one type of.

[In the formula,
R ¹ to R ⁶ are each independently 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 carbon Represents a monovalent heterocyclic group of numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -O-, -S-, -S(O) ₂ - or -CO-,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^{6 , and R 6 and} R ⁵ 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 with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -O-, -S-, -S(O) ₂ - or -CO-,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
Q ¹ and Q ² 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 with -Si(-)(-)-,
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -O-, -S-, -S(O) ₂ - or -CO-,
The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
When a plurality of Z ¹ to Z ⁴ , M and MM exist, they may be the same or different from each other. ]
[2] The colored curable resin composition according to [1], wherein the singlet oxygen quencher is a transition metal complex.
[3] The colored curable resin composition according to [2], wherein the singlet oxygen quencher is a transition metal complex containing at least one selected from a nickel complex, a copper complex, and a cobalt complex.
[4] of [1] to [3], wherein Q ¹ and Q ² in formula (I) or formula (II) are each independently a group represented by formula (QQ1) or formula (QQ2); Colored curable resin composition according to any one of the above.

[In the formula,
R ^Q1 to R ^Q10 are each independently 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 carbon Represents a monovalent heterocyclic group of numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is -O-, -S-,
-S(O) ₂ - or -CO- may be substituted,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
R ^Q1 to R ^Q4 may each be bonded to one or more members selected from R ^Q1 to R ^Q4 to form a ring,
R ^Q5 to R ^Q10 may each be bonded to one or more members selected from R ^Q5 to R ^Q10 to form a ring.
M and MM represent the same meanings as above.
* indicates a bond. ]
[5] The colored curable resin composition according to [4], wherein at least one of Q ¹ and Q ² in formula (I) or formula (II) is a group represented by formula (QQ1).
[6] The colored curable resin composition according to any one of [1] to [5], wherein the colorant contains a compound represented by formula (I).
[7] The colored curable resin composition according to [6], wherein Q ¹ or Q ² in the formula (I) has at least one -CO ₂ H.
[8] A color filter formed from the colored curable resin composition according to any one of [1] to [7].
[9] A display device including the color filter according to [8].

According to the present invention, it is possible to provide a colored curable resin composition that can be used to form a color filter with excellent light resistance.

The colored curable resin composition of the present invention includes a colorant (hereinafter sometimes referred to as colorant (A)), a resin (hereinafter sometimes referred to as resin (B)), and a polymerizable compound (hereinafter referred to as polymerizable compound). (C)), a polymerization initiator (hereinafter sometimes referred to as a polymerization initiator (D)), and a singlet oxygen quencher (hereinafter sometimes referred to as a singlet oxygen quencher (H)). .
The colored curable resin composition of the present invention may further contain a solvent (hereinafter sometimes referred to as solvent (E)).
The colored curable resin composition of the present invention may further contain a polymerization initiation aid (hereinafter sometimes referred to as polymerization initiation aid (D1)).
The colored curable resin composition of the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)).
The colored curable resin composition of the present invention may further contain an antioxidant (hereinafter sometimes referred to as antioxidant (G)).
In this specification, the compounds exemplified as each component can be used alone or in combination, unless otherwise specified.

<Coloring agent (A)>
Colorant (A) is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) and a compound represented by formula (II) (hereinafter sometimes referred to as compound (II)). Contains at least one selected from.

［式中、
Ｒ¹～Ｒ⁶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。
Ｒ¹及びＲ²、Ｒ²及びＲ³、Ｒ³及びＲ⁴、Ｒ⁴及びＲ⁶、及びＲ⁶及びＲ⁵は、それぞれ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。］ <<Compound (I), Compound (II)>>

[In the formula,
R ¹ to R ⁶ are each independently 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 carbon Represents a monovalent heterocyclic group of numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -O-, -S-, -S(O) ₂ - or -CO-,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^{6 , and R 6 and} R ⁵ 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 with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -O-, -S-, -S(O) ₂ - or -CO-,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
Q ¹ and Q ² 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 with -Si(-)(-)-,
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -O-, -S-, -S(O) ₂ - or -CO-,
The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
When a plurality of Z ¹ to Z ⁴ , M and MM exist, they may be the same or different from each other. ]

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom, a chlorine atom, and a bromine atom being preferred, and a chlorine atom being more preferred.

The number of carbon atoms in the monovalent hydrocarbon group represented by R ¹ to R ⁶ and Z ¹ to Z ⁴ is 1 to 40, preferably 1 to 30, more preferably 1 to 20, and Preferably it is 1-18, and even more preferably 1-12.
The monovalent hydrocarbon group having 1 to 40 carbon atoms represented by R ¹ to R ⁶ and Z ¹ to Z ⁴ may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group; The hydrogen group may be saturated or unsaturated, and may be chain or cyclic (alicyclic hydrocarbon group).

The saturated or unsaturated chain hydrocarbon groups represented by R ¹ to R ⁶ and Z ¹ to Z ⁴ include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group. , nonyl group, and linear alkyl group such as decyl group;
Isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, 1,1,3,3-tetramethylbutyl group, 1-methylbutyl group, 1-ethyl group Branched chains such as propyl group, 3-methylbutyl group, neopentyl group, 1,1-dimethylpropyl group, 2-methylpentyl group, 3-ethylpentyl group, 1,3-dimethylbutyl group, and 2-ethylhexyl group Alkyl group;
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) 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, Alkenyl groups such as pentenyl groups (e.g., 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group) and hexenyl groups (e.g., 1-hexenyl group, 5-hexenyl group);
Alkynyl groups such as ethynyl group, propynyl group (e.g., 1-propynyl group, 2-propynyl group), octynyl group (e.g., 1-octynyl group, 7-octynyl group), butynyl group, pentynyl group, and hexynyl group; etc. can be mentioned.

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

The saturated or unsaturated alicyclic hydrocarbon groups represented by R ¹ to R ⁶ and Z ¹ to Z ⁴ include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cycloheptyl group. Cycloalkyl groups such as groups;
Cycloalkenyl groups such as cyclohexenyl group (e.g. cyclohex-1-en-1-yl group, cyclohex-2-en-1-yl group, cyclohex-3-en-1-yl group), cycloheptenyl group and 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, still more preferably 3 to 18, even more preferably 3 to 12. . Among these, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups are particularly preferred.

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

The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, still more preferably 6 to 18 carbon atoms, and still more preferably 6 to 12 carbon atoms.

The hydrocarbon groups represented by R ¹ to R ⁶ and Z ¹ to Z ⁴ may be a combination of the hydrocarbon groups listed above. Examples of the group combining the above-mentioned hydrocarbon groups include a combination of at least one selected from an aromatic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. a group combining a chain hydrocarbon group and an alicyclic hydrocarbon group; and the like.

Examples of the group combining an aromatic hydrocarbon group with at least one selected from an aromatic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group include a benzyl group, (4-methylphenyl) Methyl group and aralkyl group such as phenethyl group; 1-phenylethenyl group, 2-phenylethenyl group (phenylvinyl group), 2,2-diphenylethenyl group, 2-phenyl-2-(1-naphthyl) Arylalkenyl group such as ethenyl group; Arylalkynyl group such as phenylethynyl group; Aryl (preferably phenyl) group to which an arylalkynyl group such as (phenylethynyl)phenyl group is bonded; One or more of biphenylyl group, terphenylyl group, etc. A phenyl group to which a phenyl group is bonded; examples include a cyclohexylmethylphenyl group, a benzylphenyl group, and a (dimethyl(phenyl)methyl)phenyl group. The number of carbon atoms is preferably 7 to 30, more preferably 7 to 20, still more preferably 7 to 18, even more preferably 7 to 15.

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

The monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ¹ to R ⁶ and Z ¹ to Z ⁴ represents a group containing a heteroatom as a ring constituent. In addition, a monovalent heterocyclic group means a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring from a heterocycle. The monovalent heterocyclic group having 1 to 40 carbon atoms may be monocyclic or polycyclic. Examples of heteroatoms include nitrogen atoms, oxygen atoms, and sulfur atoms.

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

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

Examples of the heterocycle containing an oxygen atom include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, and 1,4-dioxane; 1,4-dioxaspiro[4.5]decane; Bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]nonane and 1,4-dioxaspiro[4.4]nonane; α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valero Lactone heterocycles such as lactone and δ-valerolactone; 5-membered unsaturated heterocycles such as furan, 2,3-dimethylfuran, 2,5-dimethylfuran; 2H-pyran, 4H-pyran, etc. 6-membered unsaturated heterocycles such as benzofuran, benzopyran, benzodioxole, 1,3-benzodioxole, benzodioxane, chroman and isochroman; fused bicyclic heterocycles such as xanthene and dibenzofuran; Cyclic heterocycle; etc. are mentioned.

Examples of heterocycles containing a sulfur atom include 5-membered saturated heterocycles such as dithiolane; 6-membered saturated heterocycles such as thiane, 1,3-dithiane, and 2-methyl-1,3-dithiane; thiophene and thiopyran. , 5-membered unsaturated heterocycles and 6-membered unsaturated heterocycles such as benzothiopyran; fused bicyclic heterocycles such as benzothiopyran and benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; etc. can be mentioned.

Examples of the heterocycle containing a nitrogen atom and an oxygen atom include morpholine, 2-pyrrolidone, 1-methyl-2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 1-methyl-2-piperidone and 2-methyl- Monocyclic saturated heterocycles such as 2-piperidone; monocyclic unsaturated heterocycles such as oxazole and isoxazole; fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; Examples include fused tricyclic heterocycles such as phenoxazine.

Examples of the heterocycle containing a nitrogen atom and a sulfur atom include monocyclic heterocycles such as thiazole; fused bicyclic heterocycles such as benzothiazole; and fused tricyclic heterocycles such as phenothiazine.

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-, and the monovalent carbonization -CH(-)- constituting the hydrogen group and the monovalent heterocyclic group may be replaced with -N(-)-, and the monovalent hydrocarbon group and the monovalent heterocyclic group Constituent -CH= may be replaced with -N=, and -CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is -O-, -S-, - It may be replaced with S(O) ₂ - or -CO-. Such a base is

-SiH ₃ ;
A silyl group having 1 to 3 hydrocarbon groups such as -Si(CH ₃ ) ₃ , -Si(CH ₂ CH ₃ ) ₃ , -Si(CH ₃ ) ₂ (CH ₂ CH ₃ );
-Si(OH) ₃ , -Si(OCH ₃ ) ₃ , -Si(OCH ₂ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₂ CH ₃ ) ₃ , -SiH ₂ (OH), -Si(CH ₃ ) A silyl group having 1 _to 3 of at least one selected from hydroxy groups, alkoxy groups, and aryloxy groups such as 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-butyl Amino group, N-tert-butylamino group, N,N
-di-tert-butylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N-propylmethylamino group, N,N-isopropylmethylamino group, N , an amino group having one or two hydrocarbon groups such as N-butylmethylamino group, N,N-tert-butylmethylamino group and N,N-phenylmethylamino group;
Methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl)hexyloxy group, phenyloxy oxy groups (alkoxy groups and aryloxy groups) to which a hydrocarbon group such as a group, m-tolyloxy group, and 3,4-xylyloxy group is bonded;
Oxiranyl group;
Formyl group;
Alkanoyl groups such as acetyl group, propanoyl group, butanoyl group, tert-butanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, benzoyl group;
Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, phenyloxycarbonyl group, o-tolyl An oxycarbonyl group to which a hydrocarbon group such as an oxycarbonyl group is bonded;
Mercapto group;
A mercapto group bonded with a hydrocarbon group 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, 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-dipropyls rufamoyl 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, N-tert-butylsulfamoyl group, N,N-di-tert-butylsulfamoyl group Famoyl group, N-phenylsulfamoyl group, N,N-diphenylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethyl One or two hydrocarbon groups such as sulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group and N,N-phenylmethylsulfamoyl group Sulfamoyl group having;
N-formylamino group;
N-acetylamino group, N-propanoylamino group, N-butanoylamino group, N-2,2-dimethylpropanoylamino group, N-pentanoylamino group, N-hexanoylamino group, N-(2 -ethyl) N-alkanoylamino groups such as hexanoylamino groups and N-benzoylamino groups;
Hydroxy group;
Formyloxy group, acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl)hexanoyloxy group, benzoyloxy group Alkanoyloxy groups such as;
Substituted with hydrocarbon groups such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl)hexylsulfonyl group, phenylsulfonyl group and p-tolylsulfonyl group Sulfonyl 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, N-tert-butylcarbamoyl group, N,N-di-tert-butylcarbamoyl group, N-phenylcarbamoyl group, N,N-diphenylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N- Carbonization of one or two propylmethylcarbamoyl groups, N,N-isopropylmethylcarbamoyl groups, N,N-butylmethylcarbamoyl groups, N,N-tert-butylmethylcarbamoyl groups, N,N-phenylmethylcarbamoyl groups, etc. A carbamoyl group having a hydrogen group; etc. can be mentioned.

Further, the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM. .

Examples of the alkali metal atoms represented by M and MM include alkali metal atoms such as lithium atom, sodium atom, and potassium atom.

Examples of the metal atom which may have a ligand represented by M and MM include metal atoms belonging to groups 2 to 15 of the periodic table of elements. The metal atoms are more preferably Mg, Ca, Sr, Ba, Cd, Ni, Zn, Cu, Hg, Fe, Co, Sn, Pb, Mn, Al, Cr, Rh, Ir, Pd, Ti, Zr, Hf, Si, Ge, more preferably Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Sn, Mn, Al, Cr, particularly preferably Mg, Ca, These are 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, NO ₃ , SO ₄ , CH ₃ CO ₂ , OH, etc.
The ligand coordinated to the metal atom and a carbon atom, nitrogen atom, oxygen atom, sulfur atom, etc. 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,
They may form oligomers or polymers.
When the compound (I) or compound (II) contains a metal atom that may have a ligand, the ligand may include a compound excluding the metal atom that may have a ligand ( I) or compound (II).
Compound (I) and compound (II) also include such oligomers or polymers.
However, the charge of compound (I) and compound (II) is 0.

Z ¹ to Z ⁴ may be the same or different, preferably the same.
As Z ¹ to Z ⁴ ,
Each independently is preferably a hydrogen atom or a monovalent hydrocarbon group having 1 to 40 carbon atoms,
Each independently is more preferably a hydrogen atom, or a linear alkyl group or a branched alkyl group (hereinafter sometimes simply referred to as an "alkyl group"),
Each independently is more preferably a hydrogen atom or an alkyl group having 1 to 12 carbon atoms,
Particularly preferred is a hydrogen atom.

Examples of N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ) represented by M and MM include NH ₄ ;NH ₃ (CH ₂ CH ₃ ), NH ₃ ((CH ₂ ) ₇ CH Groups in which three of Z ₁ ^to Z ⁴ are hydrogen atoms and one is an alkyl group such as 3); Z ¹ to Z ⁴ such as NH ₂ (CH ₃ ) ₂ and NH ₂ (CH ₂ CH ₃ ) ₂ A group in which two of them are hydrogen atoms and two are alkyl groups; one of Z ¹ to Z ⁴ such as NH(CH ₃ ) ₃ and NH(CH ₂ CH ₃ ) ₃ is a hydrogen atom and three are Examples include groups that are alkyl groups; groups where all of Z ¹ to Z ⁴ are alkyl groups, such as N(CH ₃ ) ₄ and N(CH ₂ CH ₃ ) ₄ ; among them, NH ₄ is preferred.

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

MM includes an alkali metal atom, Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, and Mg 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, Co which may have a ligand. Al or Cr which may have a ligand is preferred.

R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ^4. and R ⁶ , and R ⁶ and R ⁵ may be bonded to each other to form a ring.

As R ¹ to R ⁶ ,
Each independently is preferably a hydrogen atom, a halogen atom, or a monovalent hydrocarbon group having 1 to 40 carbon atoms,
Each independently is more preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 12 carbon atoms,
Particularly preferred is a hydrogen atom.

Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group. Note that the divalent hydrocarbon group includes a group in which one hydrogen atom directly bonded to a carbon atom constituting the monovalent hydrocarbon group is removed, and a preferable embodiment thereof is the number of carbon atoms explained above. A preferred embodiment of a monovalent hydrocarbon group having 1 to 40 atoms, with one hydrogen atom removed; Examples include a group in which one directly bonded hydrogen atom is removed, and a preferred embodiment thereof is a group in which one hydrogen atom is removed from the preferred embodiment of the monovalent heterocyclic group having 1 to 40 carbon atoms explained above. be.

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

The group replacing the hydrogen atom constituting the divalent hydrocarbon group and the divalent heterocyclic group is preferably a halogen atom, a cyano group, a nitro group, -SO ₃ H, or -CO ₂ M, More preferably a halogen atom, a nitro group, -CO ₂ M, even more preferably a nitro group, -CO ₂ M, even more preferably a nitro group, -CO ₂ H, particularly preferably -CO ₂ H It is.

Q ¹ or Q ² in compound (I) preferably has at least one -CO 2 M by replacing at least one hydrogen atom with -CO ₂ M, and at least one hydrogen atom is replaced with -CO ₂ M. It is more preferable to have at least one --CO ₂ H by being replaced with --CO ₂ H.

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 are each independently any of the groups represented by formulas (QQ1) to (QQ19).

[In the formula,
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 Represents a monovalent heterocyclic group of numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is -O-, -S-,
-S(O) ₂ - or -CO- may be substituted,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
R ^Q1 to R ^Q94 may each be bonded to one or more members selected from R ^Q1 to R ^Q94 to form a ring.
M and MM represent the same meanings as above.
* indicates a bond. ]

Examples of the halogen atom include the same atoms as the halogen atom explained above, and preferred embodiments thereof are also the same.

As the monovalent hydrocarbon group having 1 to 40 carbon atoms and the monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ^Q1 to R ^Q94 , the monovalent monovalent heterocyclic group having 1 to 40 carbon atoms explained above can be used. Examples include the same groups as the hydrocarbon group and the monovalent heterocyclic group having 1 to 40 carbon atoms, and the preferred embodiments thereof are also the same.

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

R ^Q1 to R ^Q94 in compound (I) are:
Each independently is preferably 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,
Each independently is more preferably a hydrogen atom, a nitro group, -CO ₂ M, an alkyl group having 1 to 40 carbon atoms, or an arylalkynyl group having 8 to 40 carbon atoms,
More preferably, each independently is a hydrogen atom, a nitro group, -CO ₂ M, or an arylalkynyl group having 8 to 18 carbon atoms;
Each independently is more preferably a hydrogen atom, a nitro group, -CO ₂ M, or an arylalkynyl group having 8 to 12 carbon atoms;
Each independently is particularly preferably a hydrogen atom, a nitro group, -CO ₂ M, or a phenylethynyl group;
Each independently is more preferably a hydrogen atom, a nitro group, or -CO ₂ M;
Each independently is particularly preferably a hydrogen atom, a nitro group, or -CO ₂ H,
Each independently is most preferably a hydrogen atom or -CO ₂ H.

R ^Q1 to R ^Q94 in compound (II) are:
Each independently is preferably 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,
Each independently is more preferably a hydrogen atom, a nitro group, -CO ₂ M, an alkyl group having 1 to 40 carbon atoms, or an arylalkynyl group having 8 to 40 carbon atoms,
More preferably, each independently is a hydrogen atom, a nitro group, -CO ₂ M, or an arylalkynyl group having 8 to 18 carbon atoms;
Each independently is more preferably a hydrogen atom, a nitro group, -CO ₂ M, or an arylalkynyl group having 8 to 12 carbon atoms;
Each independently is particularly preferably a hydrogen atom, a nitro group, -CO ₂ H, or a phenylethynyl group,
More preferably, each independently is a hydrogen atom or a phenylethynyl group.

For ^Q1 and ^Q2 ,
More preferably, each independently is a group represented by formula (QQ1) to formula (QQ12),
More preferably, each independently is a group represented by formula (QQ1) to formula (QQ5),
More preferably, each group is independently a group represented by formula (QQ1) or formula (QQ2).
Furthermore, as for Q ¹ and Q ² , it is preferable that at least one of Q ¹ and Q ² is a group represented by formula (QQ1), and it is more preferable that Q ² is a group represented by formula (QQ1). Preferably, both Q ¹ and Q ² are groups represented by formula (QQ1).

The group represented by formula (QQ1) in compound (I) is
A group in which any one of R ^Q1 to R ^Q4 is a halogen atom, a cyano group, a nitro group, -CO ₂ M, or a monovalent hydrocarbon group having 1 to 40 carbon atoms, and all the others are hydrogen atoms is preferable. ,
More preferably, any one of R ^Q1 to R ^Q4 is a nitro group, -CO ₂ M, or an arylalkynyl group having 8 to 40 carbon atoms, and all the remaining are hydrogen atoms,
More preferably, any one of R ^Q1 to R ^Q4 is a nitro group, -CO ₂ M, or an arylalkynyl group having 8 to 18 carbon atoms, and all the remaining are hydrogen atoms,
A group in which any one of R ^Q1 to R ^Q4 is a nitro group, -CO ₂ M, or an arylalkynyl group having 8 to 12 carbon atoms, and all the remaining are hydrogen atoms is even more preferable,
Particularly preferred is a group in which any one of R ^Q1 to R ^Q4 is a nitro group, -CO ₂ M, or a phenylethynyl group, and all the remaining are hydrogen atoms,
More preferably, any one of R ^Q1 to R ^Q4 is a nitro group or -CO ₂ M, and all the remaining are hydrogen atoms,
Particularly preferred are groups in which any one of R ^Q1 to R ^Q4 is a nitro group or -CO ₂ H, and all the remaining are hydrogen atoms,
Most preferred is a group in which any one of R ^Q1 to R ^Q4 is -CO ₂ H and all the remaining are hydrogen atoms.

The group represented by formula (QQ1) in compound (II) is
A group in which any one of R ^Q1 to R ^Q4 is a halogen atom, a cyano group, a nitro group, -CO ₂ M, or a monovalent hydrocarbon group having 1 to 40 carbon atoms, and all the others are hydrogen atoms is preferable. ,
More preferably, any one of R ^Q1 to R ^Q4 is a nitro group, -CO ₂ M, or an arylalkynyl group having 8 to 40 carbon atoms, and all the remaining are hydrogen atoms,
More preferably, any one of R ^Q1 to R ^Q4 is a nitro group, -CO ₂ M, or an arylalkynyl group having 8 to 18 carbon atoms, and all the remaining are hydrogen atoms,
A group in which any one of R ^Q1 to R ^Q4 is a nitro group, -CO ₂ M, or an arylalkynyl group having 8 to 12 carbon atoms, and all the remaining are hydrogen atoms is even more preferable,
Particularly preferred is a group in which any one of R ^Q1 to R ^Q4 is a nitro group, -CO ₂ H, or a phenylethynyl group, and all the remaining are hydrogen atoms,
A group in which one of R ^Q1 to R ^Q4 is a phenylethynyl group and all the others are hydrogen atoms is more preferred.

The group represented by formula (QQ2) is
A group in which R ^Q5 to R ^Q10 are all hydrogen atoms; a group in which any one of R ^Q5 to R ^Q10 is a halogen atom, a cyano group, a nitro group, or -CO ₂ M, and the rest are all hydrogen atoms; Preferably,
Particularly preferred is a group in which R ^Q5 to R ^Q10 are all hydrogen atoms.

The group represented by formula (QQ3) is
A group in which R ^Q11 to R ^Q16 are all hydrogen atoms; a group in which any one of R ^Q11 to R ^Q16 is a halogen atom, a cyano group, a nitro group, or -CO ₂ M, and the rest are all hydrogen atoms; Preferably,
Particularly preferred is a group in which R ^Q11 to R ^Q16 are all hydrogen atoms.

The group represented by formula (QQ4) is
A group in which R ^Q17 to R ^Q24 are all hydrogen atoms; a group in which any one of R ^Q17 to R ^Q24 is a halogen atom, a cyano group, a nitro group, or -CO ₂ M, and the rest are all hydrogen atoms; Preferably,
Particularly preferred is a group in which R ^Q17 to R ^Q24 are all hydrogen atoms.

The group represented by formula (QQ5) is
A group in which R ^Q25 to R ^Q30 are all hydrogen atoms; a group in which any one of R ^Q25 to R ^Q30 is a halogen atom, a cyano group, a nitro group, or -CO ₂ M, and the rest are all hydrogen atoms; Preferably,
Particularly preferred is a group in which R ^Q25 to R ^Q30 are all hydrogen atoms.

Compound (I) or compound (II) is at least one selected from a halogen atom, a cyano group, a nitro group, -CO ₂ M, and an arylalkynyl group, preferably a nitro group, -CO ₂ M, and a carbon number. A compound having at least one type selected from 8 to 12 arylalkynyl groups (hereinafter sometimes referred to as modified compound (I) or modified compound (II)) is preferred. According to the colored curable resin composition containing the modified compound (I) or the modified compound (II) as the colorant (A), the light resistance of the resulting color filter can be further improved.

The halogen atom, cyano group, nitro group, -CO ₂ M, and arylalkynyl group can be introduced into modified compounds (I) and (II) as any of R ¹ to R ⁶ and R ^Q1 to R ^Q94 . It is preferably introduced into the modified compound (I) or (II) as any one of R ^Q1 to R ^Q94 .

Examples of compound (I) include compounds (Ia1) to (Ia144) represented by formulas (Ia) shown in Tables 1 to 2 below.

Examples of compound (II) include compounds (IIa1) to (IIa144) represented by formulas (IIa) shown in Tables 3 to 4 below.

In Tables 1 to 4, Qa1 to Qa12 mean groups represented by the following formulas (Qa1) to (Qa12), respectively.

［式中、※は結合手を表す。］

[In the formula, * represents a bond. ]

As compound (I),
Compound (Ia1) to compound (Ia12), compound (Ia90) to compound (Ia100), and compound (Ia123) to compound (Ia144) are preferred,
Compound (Ia1) to Compound (Ia12), Compound (Ia91) to Compound (Ia94), Compound (Ia96), Compound (Ia98) to Compound (Ia100), Compound (Ia124) to Compound (Ia127), Compound (Ia129), Compound (Ia130), compound (Ia132), and compound (Ia133) are more preferred,
More preferred are compound (Ia7), compound (Ia8), compound (Ia10), compound (Ia11), compound (Ia12), compound (Ia91), compound (Ia99), compound (Ia124), and compound (Ia130),
Compound (Ia7), compound (Ia11), and compound (Ia124) are even more preferred,
Compound (Ia11) is particularly preferred.

As compound (II),
Compound (IIa1) to compound (IIa12), compound (IIa90) to compound (IIa100), and compound (IIa123) to compound (IIa133) are preferred,
Compound (IIa1) to Compound (IIa12), Compound (IIa91) to Compound (IIa94), Compound (IIa96), Compound (IIa98) to Compound (IIa100), Compound (IIa124) to Compound (IIa127), Compound (IIa129), More preferred are compound (IIa130), compound (IIa132), compound (IIa133), compound (IIa135) to compound (IIa138), compound (IIa140), compound (IIa141), compound (IIa143), and compound (IIa144),
Compound (IIa7), Compound (IIa8), Compound (IIa10), Compound (IIa11), Compound (IIa12), Compound (IIa91), Compound (IIa99), Compound (IIa124), Compound (IIa130), Compound (IIa99), Compound (IIa124), compound (IIa130), compound (IIa135), compound (IIa141), and compound (IIa144) are more preferred,
Compound (IIa12) is even more preferred.

The method for producing compound (I) is not particularly limited, but for example, compound (I) may be produced by reacting a compound represented by formula (pt1) with a compound represented by formula (pt2) and a compound represented by formula (pt3). can do. Hereinafter, this manufacturing method may be referred to as manufacturing method 1.

［式中、Ｒ¹～Ｒ⁵、Ｑ¹及びＱ²は、前記と同一の意味を表す。］

[In the formula, R ¹ to R ⁵ , Q ¹ and Q ² have the same meanings as above. ]

The amount of the compound represented by formula (pt2) used in the reaction of production method 1 is usually 0.1 to 30 mol, preferably 1 to 1 mol of the compound represented by formula (pt1). ~20 moles, more preferably 1 to 16 moles, even more preferably 1 to 10 moles.

The amount of the compound represented by formula (pt3) used in the reaction of production method 1 is usually 0.1 to 30 mol, preferably 1 to 1 mol of the compound represented by formula (pt1). ~20 moles, more preferably 1 to 16 moles, even more preferably 1 to 10 moles.

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, even more preferably 150 to 200°C. It is.

The reaction time is usually 0.5 to 500 hours.

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

Solvents include water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1 - Alcohol solvents such as 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 carbonization such as hexane Hydrogen solvents; Aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g. 1,3,5-trimethylbenzene), decalin, tetralin; methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g. 1, 3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N- Examples include amide solvents such as methylpyrrolidone; and sulfoxide solvents such as dimethylsulfoxide, among which methyl benzoate is preferred.

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

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; acetic acid. , carboxylic acids such as trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid; etc., preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfone Acids include p-toluenesulfonic acid and carboxylic acids, more preferably carboxylic acids, and even more preferably benzoic acid.

The amount of acid used in the reaction of production method 1 is usually 1 to 90 mol, preferably 1 to 70 mol, more preferably 1 to 50 mol, per 1 mol of the compound represented by formula (pt1). The amount is mol, more preferably 1 to 30 mol.

In addition, when compound (I) has a carboxylic acid and/or ester in its structure, when alcohol, ether, ester, etc. are present as a solvent etc. in the manufacturing process of said compound (I), said compound ( A compound obtained by esterifying and/or transesterifying the carboxylic acid and/or ester of I) may be produced as a mixture with the target compound (I). For example, when using methyl benzoate as a solvent in the step of producing the following compound (Ia11), a compound represented by formula (Ia11-a), a compound represented by formula (Ia11-b), and a compound represented by formula A compound represented by (Ia11-c) may be included together with compound (Ia11).

The method for removing compound (I) from the reaction mixture is not particularly limited, and it can be removed by various known methods.
For example, after the completion of the reaction, the reaction mixture is thoroughly mixed with a solvent such as methanol, in which compound (I) in the reaction mixture may be difficult to dissolve, but compounds other than compound (I) can be easily dissolved. Compound (I) can be taken out by filtration. Furthermore, 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 Alternatively, the resulting residue may be washed with 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 recover compound (I). Furthermore, it may be purified by column chromatography and/or recrystallization.
Alternatively, after the 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, etc.
After the reaction is completed, the reaction mixture may be purified by column chromatography and/or recrystallization.

In addition, the compound represented by formula (I) can be obtained by reacting the compound represented by formula (pt1) with the compound represented by formula (pt2) to form a compound represented by formula (I') (hereinafter referred to as , may be referred to as compound (I')), and then,
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).

［式中、Ｒ¹～Ｒ⁵、Ｑ¹、Ｑ²は、前記と同一の意味を表す。］

[In the formula, R ¹ to R ⁵ , Q ¹ and Q ² have the same meanings as above. ]

In the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), the amount of the compound represented by formula (pt2) to be used is 1 mole of the compound represented by formula (pt1). On the other hand, the amount is usually 0.1 to 60 mol, preferably 1 to 40 mol, more preferably 1 to 32 mol, and still more preferably 2 to 20 mol.

The amount of the compound represented by formula (pt3) used in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is 1 mol of the compound represented by formula (IM1). The amount is usually 0.1 to 30 mol, preferably 1 to 20 mol, more preferably 1 to 16 mol, and still more preferably 1 to 10 mol.

Reaction temperature and reaction time in the reaction of the compound represented by formula (pt1) and the compound represented by formula (pt2), and the reaction temperature and reaction time of the compound represented by formula (IM1) and the compound represented by formula (pt3) The reaction temperature and reaction time in the reaction with the compound are the same as those in Production Method 1, and their preferred embodiments 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 by , carried out in the presence of a solvent. Examples of the solvent include the solvents exemplified in Production Method 1, and preferred embodiments are also the same.

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

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 1000 parts by mass per 1 part by mass of the compound represented by formula (IM1). Part by mass.

In 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), acid It is preferable that the two coexist. Examples of the acid include the acids exemplified in Production Method 1, and preferred embodiments are also the same.

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

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 mol per 1 mol of the compound represented by formula (IM1). The amount is preferably 1 to 70 mol, more preferably 1 to 50 mol, and even more preferably 1 to 30 mol.

In addition, similarly to Production Method 1, when compound (I) has a carboxylic acid and/or ester in its structure, the carboxylic acid and/or ester possessed by compound (I) is esterified and/or transesterified. The compound may be produced as a mixture with the target compound (I).

A method for extracting a compound represented by formula (I') from a reaction mixture in the reaction of a compound represented by formula (pt1) and a compound represented by formula (pt2), and a method for extracting a compound represented by formula (IM1) The method for removing the compound represented by formula (I) from the reaction mixture in the reaction between the compound represented by formula (pt3) and the compound represented by formula (pt3) is not particularly limited, and it can be taken out by various known methods, For example, the method exemplified in Manufacturing Method 1 can be mentioned.

Examples of the base in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base include triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5. 4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, and other organic bases; sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, etc. metal alkoxides, organometallic compounds such as methyllithium, butyllithium, tert-butyllithium, and phenyllithium, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, etc. Inorganic bases are preferred, and potassium hydroxide is more preferred.

The amount of the 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 mol per 1 mol of the compound represented by formula (I'). The amount is preferably 1 to 70 mol, more preferably 2 to 40 mol.

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 per 1 part by mass of the compound represented by formula (I'). The amount is preferably 1 to 200 parts by weight, more preferably 1 to 100 parts by weight, and even more preferably 1 to 50 parts by weight.

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. , more preferably 40 to 100°C, even more preferably 60 to 100°C.

The reaction time in 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. It is 5 to 120 hours, preferably 1 to 72 hours, and more preferably 1 to 24 hours.

The method for removing 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 various known methods can be used to take out the compound represented by formula (IM1). For example, the method exemplified in Manufacturing Method 1 can be mentioned.

The method for producing compound (II) is not particularly limited, but with reference to the method for producing compound (I) described above, the compound represented by formula (pt1) is replaced with the compound represented by formula (pt1') below. can be manufactured.

［式中、Ｒ²～Ｒ⁶は、前記と同一の意味を表す。］

[In the formula, R ² to R ⁶ have the same meanings as above. ]

When the colorant (A) contains the compound (I), the content of the compound (I) may be 100% by mass based on the total amount of the colorant (A), and the lower limit is, for example, 0. It may be 1% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, even more preferably 30% by mass or more, and even more preferably 50% by mass or more.

When the colorant (A) contains the compound (II), the content of the compound (II) may be 100% by mass based on the total amount of the colorant (A), and the lower limit is, for example, 0. It may be 1% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, even more preferably 30% by mass or more, and even more preferably 50% by mass or more.

The colorant (A) preferably contains compound (I), and may contain both compound (I) and compound (II).

When the colorant (A) contains one or more of each of compound (I) and compound (II), the total content of compound (I) and compound (II) is based on the total amount of colorant (A). The lower limit may be, for example, 0.1% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 20% by mass or more. , more preferably 30% by mass or more, and even more preferably 50% by mass or more.

When the colorant (A) contains at least one compound (I) and one or more compounds (II), the content ratio of compound (I) and compound (II) (compound (II)/compound (I)) is , is preferably 0.01 or more and 100 or less, more preferably 0.05 or more and 50 or less on a molar basis.

<<Colorant (A1)>>
The colored curable resin composition of the present invention uses a dye other than compound (I) and compound (II) (hereinafter sometimes referred to as dye (A1-1)) and/or pigment (hereinafter referred to as dye (A1-1)) as the colorant (A). , pigment (A1-2)) (hereinafter, dye (A1-1) and pigment (A1-2) may be collectively referred to as colorant (A1)). These may be used alone or in combination of two or more.

As the dye (A1-1), any known dye can be used as long as it does not contain compound (I) or compound (II), and examples thereof include solvent dyes, acid dyes, direct dyes, mordant dyes, and the like. Examples of the dye include compounds classified as dyes in Color Index (published by The Society of Dyers and Colorists) and known dyes listed in Dyeing Notes (Shirosensha). Also, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline Examples include dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes, and the like.

Specifically, dyes having the following color index (C.I.) numbers may be mentioned.
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 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. 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 Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; I. solvent dye,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 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, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;
C. I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, C. 104, 105, 106, 109; etc. I. acid dye,
C. I. Direct Yellow 2, 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 Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C. I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 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 Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; I. direct dye,
C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse Violet 26, 27;
C. I. C.I. such as Disperse Blue 1, 14, 56, 6;0. I. disperse dye,
C. I. Basic Red 1, 10;
C. I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;
C. I. Basic Violet 2;
C. I. Basic Red 9;
C. I. C. such as Basic Green 1; I. basic dye,
C. I. Reactive Yellow 2, 76, 116;
C. I. Reactive Orange 16;
C. I. C. such as Reactive Red 36; I. reactive dye,
C. I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modern tread 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38 , 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;
C. I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C. I. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;
C. I. Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43 , 44, 48, 49, 53, 61, 74, 77, 83, 84;
C. I. C. mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; I. mordant dye,
C. I. C. bat green 1; etc. I. Vat dye etc.

Further examples include Lumogen (registered trademark), which is a product of BASF, including Lumogen (registered trademark) F Yellow 083 (manufactured by BASF), Lumogen (registered trademark) F Yellow 170 (manufactured by BASF), and Lumogen (registered trademark). Examples include F Orange 240 (manufactured by BASF) and Lumogen (registered trademark) F Red 305 (manufactured by BASF).

As the pigment (A1-2), any known pigment can be used as long as it does not include compound (I) or compound (II), and for example, pigments classified as pigments in Color Index (published by The Society of Dyers and Colorists). Examples of pigments include:

Specifically, pigments classified as pigments include 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, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231;
C. I. Orange pigments such as Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
C. I. 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, Red pigments such as 265, 266, 268, 269, 273;
C. I. Blue pigments such as Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60;
C. I. Violet color pigments such as Pigment Violet 1, 19, 23, 32, 36, 38;
C. I. Green pigments such as Pigment Green 7, 36, 58, 59, 62, 63;
C. I. Brown pigments such as Pigment Brown 23 and 25;
C. I. Examples include black pigments such as Pigment Black 1, 7, 31, and 32.

Colorants (A1) include yellow dyes and yellow pigments (hereinafter, these may be collectively referred to as "yellow colorants"), orange dyes and orange pigments (hereinafter, these are collectively referred to as "orange colorants"). ), red dyes and red pigments (hereinafter collectively referred to as "red colorants"), green dyes and green pigments (hereinafter collectively referred to as "green colorants") A yellow coloring agent and a green coloring agent are more preferable, a yellow pigment and a green pigment are even more preferable, and a green pigment is even more preferable.

Among the above-mentioned dyes, examples of the yellow dye include those whose hue is classified as yellow, and examples of the yellow pigment include those whose hue is classified as yellow among the above-mentioned pigments.
As the yellow coloring agent, yellow dyes and yellow pigments are preferred, yellow pigments are more preferred, quinophthalone pigments, metal-containing pigments, and isoindoline pigments are even more preferred, and C.I. I. Pigment Yellow 129, 138, 139, 150, 185, and 231 are even more preferred, and C.I. I. Pigment Yellow 138, 139, 150, 185, and 231 are particularly preferred.

Among the above-mentioned dyes, examples of the orange dye include those whose hue is classified as orange, and examples of the orange pigment include those whose hue is classified as orange among the above-mentioned pigments.
As the orange colorant, orange dyes and orange pigments are preferred, orange pigments are more preferred, and C.I. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, and 73 are more preferred.

Among the above-mentioned dyes, examples of the red dye include those whose hue is classified as red, and examples of the red pigment include those whose hue is classified as red among the above-mentioned pigments.
As the red coloring agent, red dyes and red pigments are preferred, and include azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, perylene dyes, azo pigments, diketopyrrolopyrrole pigments, anthraquinone pigments, triphenylmethane pigments, and xanthene pigments. , perylene pigments are more preferred; I. Acid Red 52, C. I. Pigment Red 144, 177, 179, 242, 254, and 269 are more preferred.

Furthermore, as the yellow colorant, orange colorant, or red colorant, a xanthene compound described in JP-A-2013-235257, etc. may be used.

Examples of green dyes include those whose hue is classified as green among the above-mentioned dyes, and examples of green pigments include those whose hue is classified as green among the above-mentioned pigments.
The green coloring agent is preferably a green dye or a green pigment, more preferably a green pigment, further preferably a phthalocyanine pigment, even more preferably a halogenated copper phthalocyanine pigment, a halogenated zinc phthalocyanine pigment, or an aluminum halide zinc phthalocyanine pigment. ．． I. Pigment Green 7, 36, 58, 59, 62, and 63 are particularly preferred.

When the colorant (A) further contains a colorant (A1), the lower limit of the total content of compound (I) and compound (II) in the colorant (A) is based on the total amount of the colorant (A). , for example, 1% by mass or more, preferably 10% by mass or more, more preferably 30% by mass or more, still more preferably 50% by mass or more, particularly preferably 60% by mass or more. On the other hand, when the colorant (A) further contains the colorant (A1), the upper limit of the total content of compound (I) and compound (II) in the colorant (A) is determined by the total amount of the colorant (A). In contrast, it is, for example, less than 100% by mass.

When the colored curable resin composition contains a solvent (E), a colored composition containing the colorant (A) and the solvent (E) (hereinafter sometimes referred to as a colorant-containing liquid) is prepared in advance, and then the colored curable resin composition is A colored curable resin composition may be prepared using the colored composition. When the colorant (A) does not dissolve in the solvent (E), for example, when the colorant (A) contains a pigment (A1-2), the coloring composition is prepared by dissolving the colorant (A) in the solvent (E). (The colored composition in this case may be referred to as a colored dispersion hereinafter). The colored composition may contain part or all of the solvent (E) contained in the colored curable resin composition.

The content of solids in the coloring composition is less than 100% by mass, preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.01% by mass or more and 99.99% by mass or less, based on the total amount of the coloring composition. 1% by mass or more and 99.9% by mass or less, more preferably 0.1% by mass or more and 99% by mass or less, even more preferably 1% by mass or more and 90% by mass or less, particularly preferably 1% by mass. It is 80% by mass or less, more preferably 1% by mass or more and 70% by mass or less, particularly preferably 1% by mass or more and 60% by mass or less, and most preferably 1% by mass or more and 50% by mass or less.

The content of the colorant (A) in the coloring composition is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass or less, based on the total amount of solids in the coloring composition. Yes, more preferably 0.001% by mass or more and 99% by mass or less, still more preferably 1% by mass or more and 95% by mass or less, even more preferably 3% by mass or more and 90% by mass or less, particularly preferably It is 5% by mass or more and 90% by mass or less.

The colorant (A) may be treated, if necessary, by rosin treatment, surface treatment using a derivative with an acidic or basic group introduced therein, grafting treatment on the surface of the colorant (A) with a polymer compound, sulfuric acid, etc. Atomization treatment using an atomization method, salt milling method, etc., washing treatment with an organic solvent, water, etc. to remove impurities, removal treatment of ionic impurities by an ion exchange method, etc. may be performed.
In addition, the colorant (A) may be subjected to crystal structure conversion, particle shaping, and/or particle size substantially uniformization treatment, if necessary;
The colorant (A) is mixed with water and/or an organic solvent, stirred and/or heated to obtain a suspension, and then the suspension is filtered to change the crystal structure. Process for obtaining colorant (A);
A process of changing the crystal structure of the colorant (A) by recrystallizing;
The colorant (A) and water, sulfuric acid, or an organic solvent are mixed and stirred and/or heated to obtain a solution or suspension, and then the solution or suspension is mixed with the colorant. (A) is mixed with a poor solvent to obtain a suspension, and then the suspension is filtered to obtain a colorant (A) with a changed crystal structure;
The colorant (A), the derivative, and water and/or organic solvent are mixed and stirred and/or heated to obtain a suspension, and then the suspension is filtered to form crystals. A process for obtaining a mixture containing a colorant (A) with a changed structure and/or a process for mixing a colorant (A) and a derivative;
A process of recrystallizing a mixture of the colorant (A) and the derivative to obtain a mixture containing the colorant (A) with a changed crystal structure, and/or a process of mixing the colorant (A) and the derivative;
The colorant (A), the derivative, and water, sulfuric acid, or an organic solvent are mixed and stirred and/or heated to obtain a solution or suspension. , mixing the colorant (A) with a poor solvent to obtain a suspension, and then filtering the suspension to obtain a mixture containing the colorant (A) with a changed crystal structure and/or coloring. A treatment of mixing the agent (A) and the derivative;
etc. may be applied.
When using multiple types of colorants (A) or derivatives, these treatments may be carried out individually, or a mixture of multiple types may be used.
The particle size of the colorant (A) is preferably substantially uniform.

When the coloring composition contains a derivative, the content of the derivative is 0.01 parts by mass or more and 100 parts by mass or less, and 0.01 parts by mass or more and 70 parts by mass, based on 100 parts by mass of the colorant (A). parts by weight or less, more preferably 0.1 parts by weight or more and 50 parts by weight or less, even more preferably 0.1 parts by weight or more and 30 parts by weight or less, particularly preferably 0.1 parts by weight or more and 20 parts by weight or less.

The colorant (A) can be uniformly dispersed in the solution by containing a dispersant and performing a dispersion treatment. When using a combination of two or more types as the colorant (A), each may be individually dispersed, or a plurality of types may be mixed and dispersed.

Examples of the dispersant include surfactants, which may be cationic, anionic, nonionic, or amphoteric surfactants. Specific examples include polyester-based, polyamine-based, acrylic-based surfactants, and the like. These dispersants may be used alone or in combination of two or more. As a dispersant, the trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Florene (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers (registered trademark) (manufactured by Zeneca Corporation), and EFKA (registered trademark). (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK), BYK (registered trademark) (manufactured by BYK), and the like.

When using a dispersant, the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10,000 parts by mass or less, preferably 5 parts by mass or less, based on 100 parts by mass of the colorant (A) in the coloring composition. Parts by mass or more and 5000 parts by mass or less, more preferably 10 parts by mass or more and 3000 parts by mass or less, still more preferably 15 parts by mass or more and 1000 parts by mass or less, even more preferably 18 parts by mass or more and 500 parts by mass or less. The content is particularly preferably 20 parts by mass or more and 350 parts by mass or less. When the amount of the dispersant used is within the above range, a colored composition with a more uniformly dispersed state tends to be obtained.

When a colored composition containing a colorant (A) and a solvent (E) is prepared in advance and then a colored curable resin composition is prepared using the colored composition, the colored composition is a colored curable resin. A part or all of the resin (B) contained in the composition, preferably a part, may be included in advance. By including the resin (B) in advance, the dispersion stability of the colored composition can be further improved.

When the coloring composition contains a resin (B), the content of the resin (B) is, for example, 0.01 parts by mass or more and 10,000 parts by mass based on 100 parts by mass of the colorant (A) in the coloring composition. 0.01 parts by mass or more and 5000 parts by mass or less, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, still more preferably 0.1 parts by mass or more and 500 parts by mass or less, and 0.1 parts by mass. More preferably, the amount is 300 parts by mass or less.

The content of the colorant (A) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass, based on the total solid content of the colored curable resin composition. or less, more preferably 0.8% by mass or more and 30% by mass or less, even more preferably 1% by mass or more and 20% by mass or less. When the content of the colorant (A) is within the above range, the color density when used as a color filter is sufficient, and the resin (B) can be contained in the required amount in the composition, so that mechanical This is preferred because a pattern with sufficient strength can be formed.
Here, the "total amount of solid content" in this specification refers to the amount obtained by subtracting the solvent content from the total amount of the colored curable resin composition. The total amount of solid content and the content of each component relative to the total amount can be measured by known analytical means such as liquid chromatography or gas chromatography.

<Resin (B)>
The resin (B) is preferably an alkali-soluble resin, and contains at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter referred to as "monomer (a)"). It is more preferable to use a polymer having a structural unit derived from
The resin (B) contains 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 A copolymer having other structural units is preferred.
Other structural units include monomers copolymerizable with monomer (a) (however, they are different from monomer (a) and monomer (b). Hereinafter, "monomer (c)" ), structural units having an ethylenically unsaturated bond, etc.

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

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

Among these, acrylic acid, methacrylic acid, o-, m-, p-vinylbenzoic acid, maleic anhydride, and the like are preferred from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in aqueous alkali solutions.

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

As the monomer (b), for example, a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b1)"), an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b2)"), a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter referred to as "monomer (b3)") ), etc.

As the monomer (b1), for example, a monomer having a structure in which a linear or branched unsaturated aliphatic hydrocarbon is epoxidized (hereinafter referred to as "monomer (b1-1)") ), and a monomer having a structure in which an unsaturated alicyclic 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-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinyl Benzyl 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( glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris( 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2, Examples include 4,6-tris(glycidyloxymethyl)styrene.

Examples of the monomer (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxy Cyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) M100; manufactured by Daicel Corporation) ), a compound represented by formula (BI), a compound represented by formula (BII), and the like.

［式（ＢＩ）及び式（ＢＩＩ）中、Ｒ^a及びＲ^bは、互いに独立に、水素原子、又は炭素数１～４のアルキル基を表し、該アルキル基に含まれる水素原子は、ヒドロキシ基で置換されていてもよい。
Ｘ^a及びＸ^bは、互いに独立に、単結合、＊－Ｒ^c－、＊－Ｒ^c－Ｏ－、＊－Ｒ^c－Ｓ－又は＊－Ｒ^c－ＮＨ－を表す。
Ｒ^cは、炭素数１～６のアルカンジイル基を表す。
＊は、Ｏとの結合手を表す。］

[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 the hydrogen atom contained in the alkyl group is a hydroxy group. may be replaced with .
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 with O. ]

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

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

Preferred examples of R ^a and R ^b include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferably a hydrogen atom and a methyl group.

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

Preferably, X ^a and X ^b include a single bond, a methylene group, an ethylene group, *-CH ₂ -O-, *-CH ₂ CH ₂ -O-, and more preferably a single bond, *-CH ₂ Examples include CH ₂ -O- (* represents a bond with O).

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

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

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

As the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable.
Examples of the monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, and 3-methyl-3-(meth)acryloyl. Examples include oxyethyloxetane, 3-ethyl-3-(meth)acryloyloxyethyloxetane, and the like.

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

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

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, and 2-ethylhexyl. (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo [5.2. 1.0 ^2,6 ] Decan-8-yl (meth)acrylate (commonly referred to as "dicyclopentanyl (meth)acrylate" in the technical field. Also, "tricyclodecyl (meth)acrylate") ), tricyclo[5.2.1.0 ^2,6 ]decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth) ) acrylate (commonly referred to as “dicyclopentenyl (meth)acrylate” in the technical field), tricyclo[5.2.1.0 ^2,6 ]decen-9-yl (meth)acrylate, dicyclopentenyl (meth)acrylate, Cyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate and benzyl (meth)acrylate (Meth)acrylic acid esters such as 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 ester 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, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2 .1] hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2. 1] Hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy -5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2 .2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyl) bicyclounsaturated compounds such as (oxycarbonyl)bicyclo[2.2.1]hept-2-ene;
N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 - dicarbonylimide derivatives such as maleimidopropionate and N-(9-acridinyl)maleimide;
Vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; chloride Halogenated hydrocarbons such as vinyl and vinylidene chloride; Vinyl group-containing amides such as (meth)acrylamide; Esters such as vinyl acetate; Dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene ; etc.
Among these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, tricyclo[5.2.1 .0 ^2,6 ] decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^{2, 6} ] Decen-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, etc. preferable.

Specifically, the resin (B) includes 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-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/9-vinylcarbazole/(meth)acrylic acid copolymer, 3,4-epoxy Tricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/phenyl (meth)acrylate/o-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/phenyl (meth)acrylate/m-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/ Phenyl (meth)acrylate/p-vinylbenzoic 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/vinyltoluene 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)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 JP-A-9-106071, JP-A-2004-29518, and JP-A-2004-361455 Examples include resins described in various publications.
Among these, as the resin (B), a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b) is preferable.

Two or more resins (B) may be used in combination, and in this case, the resin (B) includes at least the following:
It is preferable to include at least one copolymer containing a structural unit derived from monomer (a) and a structural unit derived from monomer (b),
More preferably, it contains at least one copolymer containing a structural unit derived from monomer (a) and a structural unit derived from monomer (b1),
More preferably, it contains at least one copolymer containing a structural unit derived from monomer (a) and a structural unit derived from monomer (b1-2),
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/(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/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/ It is even more preferable to include one or more selected from 2-ethylhexyl (meth)acrylate copolymers.

The weight average molecular weight (Mw) of the resin (B) in terms of polystyrene is preferably 1,000 or more and 100,000 or less, more preferably 2,000 or more and 50,000 or less, and still more preferably 3,000 or more. It is 30,000 or less, and even more preferably 5,000 or more and 30,000 or less. When the weight average molecular weight is within the above range, the solubility of unexposed areas in a developer tends to be high, and the resulting pattern tends to have a high residual film rate and hardness.

The dispersity [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1 or more and 6 or less, more preferably 1 or more and 5 or less, and even more preferably 1 or more and 4 or less. It is.

The acid value (solid content equivalent value) of the resin (B) is preferably 10 mg-KOH/g or more and 300 mg-KOH/g or less, more preferably 20 mg-KOH/g or more and 250 mg-KOH/g or less, More preferably 25 mg-KOH/g or more and 200 mg-KOH/g or less, even more preferably 30 mg-KOH/g or more and 180 mg-KOH/g, particularly preferably 40 mg-KOH/g or more and 150 mg-KOH/g. g or less. The acid value here is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 5 to 90% by mass, more preferably 10 to 80% by mass, even more preferably 13% by mass, based on 100% by mass of the solid content of the colored curable resin composition. 70% by mass, and even more preferably 15 to 60% by mass. When the content of the resin (B) is within the above range, the solubility of the unexposed areas in the developer tends to be high.

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

Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. etc., and the above-mentioned monomers (a), monomers (b) and monomers (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, and triethylene glycol di(meth)acrylate. Examples include (meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

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

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

The content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass, based on the total solid content of the colored curable resin composition. or less, more preferably 10% by mass or more and 80% by mass or less, still more preferably 15% by mass or more and 70% by mass or less.

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids, etc. under the action of light or heat, and any known polymerization initiator can be used.

Examples of the polymerization initiator (D) include oxime compounds (eg, O-acyl oxime 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)octane- 1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetyloxy-1-[ 9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3 ,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-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 and the like. Further, as the O-acyloxime compound, commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (all manufactured by BASF) and N-1919 (manufactured by ADEKA Corporation) may be used. Among them, O-acyloxime compounds include N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl) phenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine , N-acetyloxy-1-{9-ethyl-6-[2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl]-9H-carbazole-3- from the group consisting of N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine At least one selected one is preferred, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine is more preferred.

Examples of alkylphenone compounds include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1- and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. As the alkylphenone compound, commercially available products such as Irgacure (registered trademark) 369, 907, and 379 (all manufactured by BASF) may be used.
Examples of alkylphenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, Mention may also be made of 1-hydroxycyclohexylphenyl 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 (for example, see JP-A-6-75372, 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(dialkoxyphenyl)biimidazole, 2,2' -bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Unexamined Patent Application Publication No. 62-174204, etc.) and 4 , 4', 5, 5'-position phenyl groups are substituted with carbalkoxy groups (for example, see JP-A No. 7-10913, etc.).

As triazine compounds, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)- 1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)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-methyl) phenyl)ethenyl]-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine. .

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

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

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

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

<Singlet oxygen quencher (H)>
The singlet oxygen quencher (H) is not particularly limited as long as it is a compound that can inactivate singlet oxygen by energy transfer from singlet oxygen, and any known singlet oxygen quencher can be used. be able to.

The colored curable resin composition of the present invention contains a singlet oxygen quencher (H) together with a colorant (A) containing at least one selected from compound (I) and compound (II). A color filter with excellent light resistance can be formed. Further, the colored curable resin composition of the present invention does not contain a singlet oxygen quencher (H) but contains a colored antioxidant such as a radical chain inhibitor, a peroxide decomposer, and a metal deactivator. A color filter with better light resistance than a resin composition can be formed.

Singlet oxygen quenchers (H) include transition metal complexes, azides such as sodium azide, antioxidants such as ascorbic acid, isobenzofuran, dihydroquinone, heme-containing transition metals such as hemoglobin, 4-oxo- Examples include 2,2,6,6-tetramethylpiperidine 1-oxyl. Note that the transition metal complexes used as the singlet oxygen quencher (H) do not include those having the structure of the aforementioned compound (I) and/or compound (II).

As the singlet oxygen quencher (H), transition metal complexes are particularly preferred. According to a colored curable resin composition containing a transition metal complex as a singlet oxygen (H) quencher, the light resistance of the formed color filter is further improved. In particular, combining a transition metal complex as singlet oxygen quencher (H) with said modified compound (I) or modified compound (II) as compound (I) or compound (II) forms This is most preferred because the light resistance of the color filter is further improved.

Examples of the central metal atom of the transition metal complex include various metal atoms belonging to Groups 3 to 11 of the periodic table of elements, preferably metal atoms that are first transition elements or third transition elements, and metal atoms that are first transition elements or third transition elements. A metal atom that is a transition element is more preferable, Co, Ni or Cu is even more preferable, Co or Ni is even more preferable, and Co is particularly preferable.

Examples of transition metal complexes include transition metal complexes in which the central metal atom is Co (hereinafter sometimes referred to as cobalt complexes), transition metal complexes in which the central metal atom is Ni (hereinafter sometimes referred to as nickel complexes), and transition metal complexes in which the central metal atom is Co (hereinafter sometimes referred to as cobalt complexes); It is preferable that at least one type selected from transition metal complexes of Cu (hereinafter sometimes referred to as copper complexes) is included.

The ligand of the transition metal complex is a neutral or anionic monodentate ligand that forms at least one type of bond selected from the group consisting of coordinate bonds and covalent bonds with the central metal atom. , or a neutral or anionic polydentate ligand, preferably a neutral or anionic monodentate ligand, or a neutral or anionic bidentate ligand. Examples of the bond between the central metal atom and the ligand include a metal-nitrogen bond, a metal-carbon bond, a metal-oxygen bond, a metal-phosphorus bond, a metal-sulfur bond, and a metal-halogen bond. Preferred are metal-carbon bonds, metal-oxygen bonds, metal-sulfur bonds, or metal-halogen bonds.

Cobalt complexes include 2,4-pentanedionato group, 2,2,6,6-tetramethyl-3,5-heptanedionato group, benzoylacetonato group, 1,3-butanedionato group, 1,1,1-tritridine A complex having a β-diketonato group such as a fluoro-2,4-pentanedionato group as a ligand is preferred, and a complex represented by the following formula (C-x) is more preferred.

［式中、
Ｒ^Co1及びＲ^Co3は、それぞれ独立して、ハロゲン原子又は炭素数１～１５の１価の炭化水素基を表し、
該１価の炭化水素基を構成する－ＣＨ₂－は、－Ｏ－又は－Ｓ－に置き換わっていてもよい。
Ｒ^Co2は、水素原子又は炭素数１～１５の１価の炭化水素基を表し、
該１価の炭化水素基を構成する－ＣＨ₂－は、－Ｏ－又は－Ｓ－に置き換わっていてもよい。］

[In the formula,
R ^Co1 and R ^Co3 each independently represent a halogen atom or a monovalent hydrocarbon group having 1 to 15 carbon atoms,
-CH ₂ - constituting the monovalent hydrocarbon group may be replaced with -O- or -S-.
R ^Co2 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 15 carbon atoms,
-CH ₂ - constituting the monovalent hydrocarbon group may be replaced with -O- or -S-. ]

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

The monovalent hydrocarbon groups having 1 to 15 carbon atoms represented by R ^Co1 to R ^Co3 include the carbonized groups represented by R ¹ to R ⁶ above, except for cases where the number of carbon atoms is 16 or more. The same example as for hydrogen groups can be given.

-CH ₂ - constituting the monovalent hydrocarbon group may be replaced with -O- or -S-.

R ^Co1 and R ^Co3 are preferably monovalent hydrocarbon groups having 1 to 15 carbon atoms, more preferably monovalent hydrocarbon groups having 1 to 10 carbon atoms, and preferably monovalent hydrocarbon groups having 1 to 5 carbon atoms. It is more preferably a straight-chain or branched alkyl group, and even more preferably a straight-chain alkyl group having 1 to 3 carbon atoms.

R ^Co2 is preferably a hydrogen atom.

As the cobalt complex, bis(2,4-pentanedionato)cobalt(II) is particularly preferred.

Nickel complexes include bis(dithiobenzyl)nickel(II), bis(tetrabutylammonium)bis(maleonitriledithiolat)nickel(II), and bis[4,4'-dimethoxy(dithiobenzyl)]nickel(II). , bis(4-dimethylaminodithiobenzyl)nickel(II), tetrabutylammonium bis(1,3-dithiol-2-thione-4,5-dithiolato)nickel(III), tetrabutylammonium bis(maleonitrile dithiolate) ) Nickel(III), Tetrabutylammonium bis(3,6-dichloro-1,2-benzenedithiolat) Nickel(III), Tetramethylammonium bis(3,4,6-trichloro-1,2-benzenedithiolat) ) nickel(III), tetrabutylammonium bis(4-methyl-1,2-benzenedithiolat) nickel(III), and tetramethylammonium bis(3,4,6-trichloro-1,2-benzenedithiolat). ) A dithiolene complex such as nickel (III) is preferred, a complex having a benzenedithiolate ligand is more preferred, and a complex represented by the following formula (Ni-x) is even more preferred.

［式中、
Ｒ^Ni1～Ｒ^Ni8は、それぞれ独立して、水素原子、ハロゲン原子又は炭素数１～１５の１価の炭化水素基を表し、
該１価の炭化水素基を構成する－ＣＨ₂－は、－Ｏ－又は－Ｓ－に置き換わっていてもよい。
Ｒ^Ni1～Ｒ^Ni4は、それぞれ互いにＲ^Ni1～Ｒ^Ni4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^Ni5～Ｒ^Ni8は、それぞれ互いにＲ^Ni5～Ｒ^Ni8から選ばれる１つ以上と結合して環を形成してもよい。
Ｙ⁺はカチオンを表す。］

[In the formula,
R ^Ni1 to R ^Ni8 each independently represent a hydrogen atom, a halogen atom, or a monovalent hydrocarbon group having 1 to 15 carbon atoms,
-CH ₂ - constituting the monovalent hydrocarbon group may be replaced with -O- or -S-.
R ^Ni1 to R ^Ni4 may be bonded to each other with one or more selected from R ^Ni1 to R ^Ni4 to form a ring,
R ^Ni5 to R ^Ni8 may each be bonded to one or more members selected from R ^Ni5 to R ^Ni8 to form a ring.
Y ⁺ represents a cation. ]

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a chlorine atom being preferred.

The monovalent hydrocarbon groups having 1 to 15 carbon atoms represented by R ^Ni1 to R ^Ni8 include the carbonized groups represented by R ¹ to R ⁶ above, except for cases where the number of carbon atoms is 16 or more. The same example as for hydrogen groups can be given.

-CH ₂ - constituting the monovalent hydrocarbon group may be replaced with -O- or -S-.

R ^Ni1 to R ^Ni4 may be bonded to each other with one or more selected from R ^Ni1 to R ^Ni4 to form a ring,
R ^Ni5 to R ^Ni8 may each be bonded to one or more members selected from R ^Ni5 to R ^Ni8 to form a ring.

R ^Ni1 to R ^Ni8 are preferably hydrogen atoms, halogen atoms, or monovalent hydrocarbon groups having 1 to 10 carbon atoms, and hydrogen atoms, halogen atoms, or linear or branched chains having 1 to 5 carbon atoms. It is more preferably a alkyl group, even more preferably a hydrogen atom or a halogen atom, even more preferably a hydrogen atom or a chlorine atom.

As for R ^Ni1 to R ^Ni8 , it is preferable that 2 to 8 of R ^Ni1 to R ^Ni8 are halogen atoms and all the remaining are hydrogen atoms, and 4 to 8 of R ^Ni1 to R ^Ni8 are halogen atoms. , it is more preferable that all the remaining are hydrogen atoms, 2 to 4 of R ^Ni1 to R ^Ni4 are halogen atoms, and 2 to 4 of R ^Ni5 to R ^Ni8 are halogen atoms, and all the remaining are hydrogen atoms. More preferably, they are atoms, and 2 to 4 of R ^Ni1 to R ^Ni4 are chlorine atoms, and 2 to 4 of R ^Ni5 to R ^Ni8 are chlorine atoms, and all the remaining are hydrogen atoms. Even more preferred.

Examples of the cation represented by Y ⁺ include ammonium cations and phosphonium cations, with ammonium cations being preferred.

Examples of ammonium cations include pyridinium ion, N,N-dimethylaminopyridinium ion, triethylammonium ion, tetramethylammonium ion, tetraethylammonium cation, piperidinium ion, N-methylpiperidinium ion, morpholinium ion, etc. and tetramethylammonium ion is preferred.

Examples of the phosphonium cation include tetraethylphosphonium ion, tetrabutylphosphonium ion, tetraphenylphosphonium ion, and the like.

As the nickel complex, tetramethylammonium bis(3,4,6-trichloro1,2-benzenedithiolat)nickel(III) is particularly preferred.

As the copper complex, a complex having as a ligand a carbene compound containing heteroatoms such as a nitrogen atom, an oxygen atom, and a sulfur atom is preferable. A complex having a compound as a ligand is more preferable, and a complex having a carbene compound as a ligand having a structure in which a hetero ring is formed by including a carbene carbon atom and hetero atoms on both sides thereof is more preferable. A complex having an N-heterocyclic carbene compound containing as a hetero atom as a ligand is even more preferred, and a complex represented by the following formula (Cu-x) is particularly preferred.

［式中、
Ｒ^Cu1～Ｒ^Cu4は、それぞれ独立して、水素原子、ハロゲン原子又は炭素数１～２０の１価の炭化水素基を表し、
該１価の炭化水素基を構成する－ＣＨ₂－は、－Ｏ－又は－Ｓ－に置き換わっていてもよい。
Ｒ^Cu1～Ｒ^Cu4は、それぞれ互いにＲ^Cu1～Ｒ^Cu4から選ばれる１つ以上と結合して環を形成してもよい。
Ｘ^Cuはハロゲン原子を表す。］

[In the formula,
R ^Cu1 to R ^Cu4 each independently represent a hydrogen atom, a halogen atom, or a monovalent hydrocarbon group having 1 to 20 carbon atoms,
-CH ₂ - constituting the monovalent hydrocarbon group may be replaced with -O- or -S-.
R ^Cu1 to R ^Cu4 may each be bonded to one or more members selected from R ^Cu1 to R ^Cu4 to form a ring.
X ^Cu represents a halogen atom. ]

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a chlorine atom being preferred.

The monovalent hydrocarbon groups having 1 to 20 carbon atoms represented by R ^Cu1 to R ^Cu4 include the carbonized groups represented by R ¹ to R ⁶ above, except for cases where the number of carbon atoms is 21 or more. The same example as for hydrogen groups can be given.

-CH ₂ - constituting the monovalent hydrocarbon group may be replaced with -O- or -S-.

R ^Cu1 to R ^Cu4 may each be bonded to one or more members selected from R ^Cu1 to R ^Cu4 to form a ring.

R ^Cu1 and R ^Cu4 are preferably monovalent hydrocarbon groups having 6 to 20 carbon atoms, and phenyl groups bonded with at least one linear or branched alkyl group having 1 to 10 carbon atoms. More preferably, it is a phenyl group in which two or more linear or branched alkyl groups having 1 to 10 carbon atoms are bonded, and more preferably a phenyl group having two or more bonded linear or branched alkyl groups having 1 to 5 carbon atoms. A phenyl group in which two or more groups are bonded is even more preferred, and a 2,4,6-trimethylphenyl group or a 2,6-diisopropylphenyl group is particularly preferred.

R ^Cu2 and R ^Cu3 are preferably a hydrogen atom or a monovalent hydrocarbon group having 1 to 5 carbon atoms, and more preferably a hydrogen atom.

X ^Cu is preferably a chlorine atom.

As the copper complex, chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I) is particularly preferred.

The content of the singlet oxygen quencher (H) is preferably 1 part by mass or more and 500 parts by mass or less, based on 100 parts by mass of the total polymerization initiator (D) contained in the colored curable resin composition, and more preferably Preferably 10 parts by mass or more and 400 parts by mass or less, more preferably 20 parts by mass or more and 300 parts by mass or less, even more preferably 25 parts by mass or more and 250 parts by mass or less, particularly preferably 30 parts by mass or more and 230 parts by mass or less. Parts by mass or less.
The content of the singlet oxygen quencher (H) is preferably 0.05% by mass or more and 25% by mass or less, more preferably 0.10% by mass or less, based on the total solid content of the colored curable resin composition. The content is at least 20% by mass, more preferably at least 0.50% by mass and at most 15% by mass, even more preferably at least 1.0% by mass and at most 12% by mass.

<Polymerization initiation aid (D1)>
The polymerization initiation aid (D1) is a compound or a sensitizer used to promote the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D). When the polymerization initiation aid (D1) is included, it is usually used in combination with the polymerization initiator (D).
Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, and 4-dimethylaminobenzoate. 2-ethylhexyl dimethylaminobenzoate, N,N-dimethylpara-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis( Examples include ethylmethylamino)benzophenone, and preferably 4,4'-bis(diethylamino)benzophenone. Furthermore, as the amine compound, a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) may be used.

Examples of alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxy Examples include anthracene and 2-ethyl-9,10-dibutoxyanthracene.

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

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

When using these polymerization initiation aids (D1), the content thereof is preferably 100 parts by mass in total of the resin (B) and the polymerizable compound (C) contained in the colored curable resin composition. The amount is 0.01 parts by mass or more and 30 parts by mass or less, more preferably 0.1 parts by mass or more and 20 parts by mass or less.

<Solvent (E)>
The solvent (E) is not particularly limited, and any solvent commonly used in the field can be used.
Solvent (E) is, for example, an ester solvent (a solvent that contains -CO-O- in the molecule but does not contain -O-), an ether solvent (a solvent that contains -O- and -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), alcohols Examples include solvents (solvents containing OH in the molecule but not containing -O-, -CO-, and -CO-O-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

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

Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether. , propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl Examples include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, and methylanisole.

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

Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone (commonly known as diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclo Examples include pentanone, cyclohexanone and isophorone.

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

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

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

Two or more of these solvents may be used in combination.

Among the above-mentioned solvents, organic solvents having a boiling point of 120° C. or more and 180° C. or less at 1 atm are preferred from the viewpoint of coating properties and drying properties. As a solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone. , cyclohexanone and N,N-dimethylformamide are preferred, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, 4-hydroxy-4-methyl-2-pentanone and cyclohexanone are more preferred.

When containing a solvent (E), the content of the solvent (E) is usually less than 100% by mass, preferably 99.99% by mass or less, and more preferably 99.99% by mass or less, based on the total amount of the colored curable resin composition. is 1% by mass or more and 99.9% by mass or less, more preferably 10% by mass or more and 99% by mass or less, even more preferably 20% by mass or more and 97% by mass or less, particularly preferably 30% by mass or more. The content is 95% by mass or less, more preferably 40% by mass or more and 95% by mass or less, particularly preferably 50% by mass or more and 95% by mass or less. When the content of the solvent (E) is within the above range, flatness during coating will be good, and display characteristics will tend to be good since the color density will not be insufficient when forming a color filter. .

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

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

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

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

When containing a leveling agent (F), the content of the leveling agent (F) is preferably 0.00001 to 3 mass%, more preferably 0.00001 to 3 mass%, based on the total amount of the colored curable resin composition. The content is 0.0001% by mass or more and 1% by mass or less, more preferably 0.0005% by mass or more and 0.5% by mass or less. Note that this content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Antioxidant (G)>
The antioxidant (G) is not particularly limited as long as it is an antioxidant commonly used industrially, and examples thereof include radical chain inhibitors, peroxide decomposers, and metal deactivators, and are preferred. is a radical chain inhibitor or a peroxide decomposer, more preferably a radical chain inhibitor. Note that the antioxidant (G) does not include the singlet oxygen quencher (H) described above. Examples of these antioxidants (G) include phenolic antioxidants, amine antioxidants, phosphorus antioxidants, and sulfur antioxidants.

Phenolic antioxidants are antioxidants that have a phenolic hydroxy group in the molecule, such as pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octadecyl -3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate 3,3',3'',5,5',5''-hexa-tert-butyl-a,a',a ''-(mesitylene-2,4,6-tolyl)tri-p-cresol, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5- Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-xylyl)methyl]-1,3,5 -triazine-2,4,6(1H,3H,5H)-trione, thiodiethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octyl-3,5-di -tert-butyl-4-hydroxy-hydrocinnic acid, 4,6-bis(octylthiomethyl)-o-cresol, 1,3,5-tris{2-[3-(3,5-di-tert- Butyl-4-hydroxyphenyl)propanoyloxy]ethyl}hexahydro-1,3,5-triazine-2,4,6-trione, 2,4-bis(n-octylthio)-6-(4-hydroxy3' ,5'-di-tert-butylanilino)-1,3,5-triazine, 3,9-bis{2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]- Examples include 1,1-dimethylethyl}-2,4,8,10-tetraoxaspiro(5,5)undecane, and vitamin E.

Commercially available products may be used as the phenolic antioxidant, and specific examples include Irganox (registered trademark) 565, 1010, 1035, 1076, 1135, 1330, 1520L, 3114, and Irganox (registered trademark). 3125, 3790 (manufactured by BASF), Adekastab (registered trademark) AO-80 (manufactured by ADEKA Corporation), Sumilizer (registered trademark) BHT, GA-80, GS (manufactured by Sumitomo Chemical Co., Ltd.) ), Cyanox (registered trademark) 1790 (manufactured by Cytec Co., Ltd.), and the like.

From the viewpoint of further improving the light resistance of the resulting color filter, the phenolic antioxidant is preferably a compound having 1 to 10 phenol skeletons, more preferably a compound having 1 to 5 phenol skeletons. Preferably, a compound having one or two phenol skeletons is more preferable, and a compound having two phenol skeletons is even more preferable. Further, the phenolic antioxidant is preferably a compound having at least one phenol skeleton in which the ortho position of the phenolic hydroxy group is an alkyl group, and one of the two ortho positions of the phenolic hydroxy group has 3 to 5 carbon atoms. It is more preferable to use a compound having at least one phenol skeleton in which the other is a branched alkyl group and the other is a straight-chain alkyl group having 1 to 3 carbon atoms, and one of the two ortho positions of the phenolic hydroxy group is a carbon More preferred is a compound having two phenol skeletons, one of which is a branched alkyl group with 3 to 5 carbon atoms and the other is a linear alkyl group with 1 to 3 carbon atoms.

The molecular weight of the phenolic antioxidant is preferably 400 or more and 1200 or less, more preferably 500 or more and 1000 or less, and still more preferably 600 or more and 900 or less.

As a phenolic antioxidant, 3,9-bis{2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethyl}-2,4 ,8,10-tetraoxaspiro(5,5)undecane is particularly preferred.

Amine-based antioxidants are antioxidants having an amino group in the molecule, and examples include hindered amine-based antioxidants and aromatic amine-based antioxidants, with hindered amine-based antioxidants being preferred as amine-based antioxidants.

Examples of hindered amine antioxidants include sebacate bis(2,2,6,6-tetramethyl-4-piperidyl) ester, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, poly{[ 6-(1,1,3,3-tetramethylbutyl)amino-1,3,5-triazine-2,4-diyl][(2,2,6,6-tetramethyl-4-piperidyl)imino] -1,6-hexamethylene [(2,2,6,6-tetramethyl-4-piperidyl)imino]} and the like.

Commercially available products may be used as the hindered amine antioxidant, and specific examples include ADEKA STAB (registered trademark) LA series (manufactured by ADEKA Corporation) and Tinuvin (registered trademark) series (manufactured by BASF). .

From the viewpoint of improving the light resistance of the obtained color filter, the hindered amine antioxidant is preferably a compound having an acryloyl group or a methacryloyl group in the molecule, such as 2,2,6,6-tetramethyl-4-piperidyl methacrylate. is particularly preferred.

Examples of aromatic amine antioxidants include 1-naphthylamine, phenyl-1-naphthylamine, N,N'-diisopropyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, N- 1,3-dimethylbutyl-N'-phenyl-p-phenylenediamine, diphenylamine, N-phenyl-p-toluidine, bis-p-tolylamine, p,p'-dioctyldiphenylamine, phenyl-α-naphthylamine, Examples include phenothiazine.

The phosphorus-based antioxidant is an antioxidant having a phosphorus atom in its molecule, and includes phosphite-based, phosphine-based, etc., and phosphine-based antioxidants are preferred as the phosphorus-based antioxidant.

Examples of phosphite-based antioxidants include triphenyl phosphite, diphenylnonyl phosphite, diphenyl (2-ethylhexyl) phosphite, tris (2,4-di-tert-butylphenyl) phosphite, and tris nonylphenyl phosphite. phyto, diphenylisooctylphosphite, 2,2'-methylenebis(4,6-di-tert-butylphenyl)octylphosphite, diphenylisodecylphosphite, diphenylmono(tridecyl)phosphite, phenyldiisodecylphosphite, phenyldi (tridecyl) phosphite, tris (2-ethylhexyl) phosphite, tris (isodecyl) phosphite, tris (tridecyl) phosphite, dibutyl hydrogen phosphite, trilauryl trithiophosphite, tetrakis (2,4-di-tert) -butylphenyl)-4,4'-biphenylene diphosphonite, 4,4'-isopropylidene diphenol dodecyl phosphite, 4,4'-isopropylidene diphenol tridecyl phosphite, 4,4'-isopropylidene diphenol dodecyl phosphite Phenol tetradecyl phosphite, 4,4'-isopropylidene diphenol pentadecyl phosphite, 4,4'-butylidene bis(3-methyl-6-tert-butylphenyl) ditridecyl phosphite, 1,1,3-tris (2-Methyl-4-tridecylphosphite-5-tert-butylphenyl)butane, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, 3,4,5,6-dibenzo- Examples include 1,2-oxaphosphane-2-oxide.

Examples of phosphine antioxidants include triphenylphosphine, diphenylbutylphosphine, diphenyloctadecylphosphine, tris(p-tolyl)phosphine, tris(p-nonylphenyl)phosphine, tris(naphthyl)phosphine, diphenyl(hydroxymethyl) Phosphine, diphenyl(acetoxymethyl)phosphine, diphenyl(β-ethylcarboxyethyl)phosphine, tris(p-chlorophenyl)phosphine, tris(p-fluorophenyl)phosphine, diphenylbenzylphosphine, diphenyl-β-cyanoethylphosphine, diphenyl(p- -hydroxyphenyl)phosphine, diphenyl-1,4-dihydroxyphenyl-2-phosphine, phenylnaphthylbenzylphosphine, and the like.

From the viewpoint of further improving the light resistance of the resulting color filter, phosphine antioxidants include compounds in which three phenyl groups, which may have substituents, are bonded to a phosphorus atom (compounds having three substituents). The optional phenyl groups may be the same or different, and examples of the substituents include halogen atoms, hydrocarbon groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, etc. ) are preferred, and triphenylphosphine is particularly preferred.

Sulfur-based antioxidants are antioxidants that have a sulfur atom in the molecule, and include, for example, dialkylthiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl, and distearyl; tetrakis[methylene(3-dodecylthio)propionate] ] β-alkylmercaptopropionic acid ester compounds of polyols such as methane; and the like.

The antioxidant (G) is preferably an antioxidant containing at least one selected from the group consisting of phenolic antioxidants, amine antioxidants, and phosphorus antioxidants, and more preferably phenolic antioxidants. The antioxidant contains at least one of a phenolic antioxidant and a phosphorous antioxidant, and more preferably an antioxidant containing a phenolic antioxidant.

The content of the antioxidant (G) is preferably 1 part by mass or more and 500 parts by mass or less, more preferably The content is 10 parts by mass or more and 400 parts by mass or less, more preferably 15 parts by mass or more and 300 parts by mass or less, even more preferably 20 parts by mass or more and 250 parts by mass or less.
The content of the antioxidant (G) is preferably 0.05% by mass or more and 25% by mass or less, more preferably 0.10% by mass, based on the total solid content of the colored curable resin composition. It is 20% by mass or less, more preferably 0.50% by mass or more and 15% by mass or less, even more preferably 1.0% by mass or more and 10% by mass or less.

<Other ingredients>
The colored curable resin composition may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as necessary. good.

<Method for producing colored curable resin composition>
The colored curable resin composition includes a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a singlet oxygen quencher (H), and a polymerization agent used as necessary. It can be prepared by mixing the initiation aid (D1), the solvent (E), the leveling agent (F) and/or other components. Mixing can be performed using known or conventional equipment and conditions.
The colorant (A) may be mixed in advance with part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle diameter becomes about 0.2 μm or less. At this time, part or all of the dispersant and resin (B) may be blended as necessary. The diameter of beads used in a bead mill is preferably 0.05 mm or more and 0.5 mm or less, and examples of the material of the beads include glass, ceramic, and metal.
The colorant (A) may be used in the form of a solution (coloring composition) in which the colorant (A) is dissolved in part or all of the solvent (E) in advance.
A desired colored curable resin composition can be prepared by mixing the remaining components to the colored composition obtained as described above to a predetermined concentration.

<Color filter>
Examples of the method for forming a colored pattern from the colored curable resin composition of the present invention include a photolithography method, an inkjet method, and a printing method. Among these, photolithography is preferred. The photolithography method is a method in which the colored curable resin composition is applied to a substrate, dried to form a composition layer, and the composition layer is exposed to light through a photomask and developed. In the photolithography method, by not using a photomask during exposure and/or not developing, it is possible to form a colored coating film that is a cured product of the composition layer. The colored pattern and colored coating film thus formed are the color filter of the present invention.

The film thickness of the color filter to be produced is not particularly limited and can be adjusted as appropriate depending on the purpose and use. For example, it is preferably 30 μm or less, more preferably 20 μm or less, and 6 μm or less. It is more preferable that it is, even more preferably that it is 3 μm or less, and the lower limit is not particularly limited, but it is usually 0.1 μm or more.

Examples of substrates include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass whose surface is coated with silica, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, and the like. A material on which a thin film of aluminum, silver, silver/copper/palladium alloy, etc. is formed is used. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates. Alternatively, a silicon substrate treated with HMDS (1,1,1,3,3,3-hexamethyldisilazane) may be used.

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

Next, the composition layer is exposed through a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern depending on the intended use is used. The light source used for exposure is preferably a light source that generates light with a wavelength of 250 nm or more and 450 nm or less. For example, light of less than 350 nm can be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm can be selectively extracted using a band pass filter that extracts these wavelength ranges. You can also Specific examples include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like. In addition, it is possible to uniformly irradiate the entire exposure surface with parallel light and to accurately align the photomask and the substrate on which the composition layer is formed, so it is possible to use a stepper (reduction projection exposure machine), proximity It is preferable to use an exposure device (mask aligner) such as an exposure machine.

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

Furthermore, it is preferable to post-bake the obtained colored pattern. The post-bake temperature is preferably 80°C or higher, more preferably 100°C or higher, preferably 250°C or lower, and more preferably 245°C or lower. The post-bake time is preferably 1 minute or more, more preferably 2 minutes or more, preferably 120 minutes or less, more preferably 60 minutes or less, and even more preferably 30 minutes or less.
The color filter, which is the colored pattern or colored coating film thus obtained, may be further subjected to surface coating treatment in order to impart various properties.

<Display device>
The color filter is used as a color filter for display devices (e.g., liquid crystal display devices, organic EL display devices, etc.), electronic paper, solid-state image sensors, etc., and is compliant with high color gamut standards such as the DCI (Digital Cinema Initiatives) standard. It is useful as a color filter used in display devices compliant with .

According to the colored curable resin composition of the present invention, it is possible to form a color filter with excellent light resistance.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited by the Examples below, and modifications may be made as appropriate within the scope of the spirit of the preceding and following. Of course, other implementations are also possible, and all of them are included within the technical scope of the present invention. In the following, unless otherwise specified, "part" means "part by mass" and "%" means "% by mass."

In the following synthesis examples, the structure of the compound was confirmed by mass spectrometry (LC; Model 1200 manufactured by Agilent; MASS; Model LC/MSD6130 manufactured by Agilent).

(Synthesis example 1)
[Preparation of compound represented by formula (Ia11)]
4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) 4.04 parts, trimellitic acid anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 10.8 parts, benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) (manufactured by Tokyo Chemical Industry Co., Ltd.) and 92.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed.
This mixture was stirred for 5 hours while being maintained at 167°C.
To this mixture, 40.2 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added.
This mixture was stirred for 9 hours while being maintained at 167°C.
To this mixture, 28.0 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added.
This mixture was stirred for 11 hours while being maintained at 170°C.
This mixture was cooled to room temperature, and 2000 parts of methanol was added to this mixture.
This mixture was stirred at room temperature.
173 parts of methanol was added to the resulting mixture.
This mixture was filtered, and the resulting residue was washed once with 124 parts of methanol, once with 160 parts, and once with 400 parts.
The obtained residue was dried under reduced pressure at 60° C. to obtain a compound represented by formula (Ia11) (dry weight: 9.91 parts; hereinafter sometimes referred to as colorant (Ia11)).

<Identification of compound represented by formula (Ia11)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 507
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 505
Exact Mass: 506

(Synthesis example 2)
[Preparation of compound represented by formula (Ia7)]
5.23 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 14.2 parts of 3-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) ) and 119 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed.
This mixture was stirred for 12 hours while being maintained at 168°C.
To this mixture were added 7.12 parts of 3-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 10.3 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). 16.0 parts (manufactured by) were added.
This mixture was stirred for 26 hours while being maintained at 170°C.
The mixture was cooled to room temperature, and 2400 parts of methanol was added to the mixture.
The resulting mixture was stirred at room temperature and then filtered.
The obtained residue was washed five times with 400 parts of methanol.
The obtained residue was dried under reduced pressure at 60° C. to obtain 13.0 parts of a compound represented by formula (Ia7) (hereinafter sometimes referred to as colorant (Ia7)).

<Identification of compound represented by formula (Ia7)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 509
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 507
Exact Mass: 508

(Synthesis example 3)
[Preparation of compound represented by formula (Ia124)]
4-Amino-2-methylquinoline (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 3.02 parts, 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 8.33 parts, benzoic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (manufactured by Kogyo Co., Ltd.) and 66.7 parts of methyl benzoate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were mixed.
This mixture was stirred for 9 hours while being maintained at 170°C.
To this mixture, 13.6 parts of 2,3-naphthalenedicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 22.9 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added. 66.4 parts (manufactured by Co., Ltd.) were added.
This mixture was stirred for 49 hours while being maintained at 170°C.
To this mixture, 8.32 parts of 2,3-naphthalenedicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 11.7 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added. 43.5 parts (manufactured by Co., Ltd.) were added.
This mixture was stirred for 28 hours while being kept at 170°C.
The mixture was cooled to room temperature, and 1300 parts of methanol was added to the mixture.
This mixture was stirred at room temperature and then filtered, and the resulting residue was washed seven times with 400 parts of methanol.
The obtained residue was dried under reduced pressure at 60°C.
To this residue was added 875 parts of N,N-dimethylformamide.
The mixture was stirred at room temperature and then filtered, and the resulting residue was washed three times with the same volume of N,N-dimethylformamide as the resulting residue.
This residue was washed three times with 200 parts of methanol.
The obtained residue was dried under reduced pressure at 60°C to obtain 7.25 parts of a compound represented by formula (Ia2).

<Identification of compound represented by formula (Ia2)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 519
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 517
Exact Mass: 518

1 mole of the compound represented by formula (Ia2) and a mixture of 20 moles of potassium hydroxide and water in an amount 10 times the weight of 1 mole of the compound represented by formula (Ia2) were mixed.
This mixture was stirred while maintaining the temperature at 90° C. until the compound represented by formula (Ia2) disappeared.
This mixture was mixed with 36% hydrochloric acid to neutralize it.
This mixture was filtered.
The resulting residue was washed with water.
This residue was purified by column chromatography to obtain a compound represented by formula (IM1-1).

<Identification of compound represented by formula (IM1-1)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 339
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 337
Exact Mass: 338

1 mol of the compound represented by formula (IM1-1), 8 mol of trimellitic acid anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 21 mol of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and formula (IM1-1) ) was mixed with methyl benzoate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) in an amount 73 times the weight of 1 mole of the compound represented by .
This mixture was stirred for 120 hours while being maintained at 170°C.
The mixture was cooled to room temperature and 13 times the weight of methanol was added to the mixture.
The resulting mixture was stirred at room temperature and then filtered.
The obtained residue was washed with methanol.
The obtained residue was purified by column chromatography to obtain a compound represented by formula (Ia124) (hereinafter sometimes referred to as colorant (Ia124)).

<Identification of compound represented by formula (Ia124)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 513
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 511
Exact Mass: 512

(Synthesis example 4)
[Preparation of compound represented by formula (IIa12)]
8-Amino-2-methylquinoline (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 1.01 parts, 4-phenylethynylphthalic anhydride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 3.49 parts, benzoic acid (Tokyo Kasei Kogyo Co., Ltd.) (manufactured by Tokyo Chemical Industry Co., Ltd.) and 28.7 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed.
This mixture was stirred for 20 hours while being maintained at 170°C.
To this mixture were added 0.476 parts of 4-phenylethynylphthalic anhydride (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 1.32 parts of benzoic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and methyl benzoate (manufactured by Tokyo Kasei Kogyo Co., Ltd.). 3.3 parts (manufactured by Co., Ltd.) were added.
This mixture was stirred for 10 hours while being maintained at 170°C.
To this mixture were added 0.801 parts of 4-phenylethynylphthalic anhydride (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 2.90 parts of benzoic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and methyl benzoate (manufactured by Tokyo Kasei Kogyo Co., Ltd.). 9.13 parts (manufactured by Co., Ltd.) were added.
This mixture was stirred for 29 hours while being maintained at 170°C.
This mixture was cooled to room temperature, 400 parts of methanol was added to this mixture, and the mixture was stirred for 1 hour.
This mixture was filtered, and the resulting residue was washed six times with 140 parts of methanol.
The obtained residue was dried under reduced pressure at 60° C. to obtain 3.12 parts of a compound represented by formula (IIa12) (hereinafter sometimes referred to as colorant (IIa12)).

<Identification of compound represented by formula (IIa12)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 619
(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 617
Exact Mass: 618

(Synthesis example 5)
[Preparation of resin B-1]
A suitable amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added thereto, and the flask was heated to 80° C. with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2, A mixed solution of 289 parts of a mixture of decane-9-yl acrylate (content ratio: 1:1 in molar ratio) and ¹²⁵ parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the temperature was maintained at 80°C for 4 hours, and then cooled to room temperature to prepare a copolymer (resin B-1) solution with a solid content of 35.1% and a viscosity of 125 mPas measured with a B-type viscometer (23°C). I got it. The weight average molecular weight (Mw) of the obtained copolymer was 9.2×10 ³ , the degree of dispersion was 2.08, and the acid value in terms of solid content was 77 mg-KOH/g. Resin B-1 has the following structural units.

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

(Synthesis example 6)
[Preparation of colored dispersion (CD-1)]
The components were mixed in the following proportions, 300 parts of zirconia beads with a diameter of 0.2 mm were added, and the mixture was shaken. The zirconia beads were removed by filtration to prepare a colored dispersion (CD-1).
Colorant (A): Colorant (Ia11) 4 parts;
Dispersant: DISPERBYK-161 (manufactured by BYK; solid content equivalent) 7.5 parts;
Resin (B): Resin B-1 (solid content equivalent) 4 parts;
Solvent (E): 84.5 parts of propylene glycol monomethyl ether acetate;

(Synthesis example 7)
[Preparation of colored dispersion (CD-2)]
The components were mixed in the following proportions, 300 parts of zirconia beads with a diameter of 0.2 mm were added, and the mixture was shaken. The zirconia beads were removed by filtration to prepare a colored dispersion (CD-2).
Colorant (A): 4 parts of colorant (Ia7);
Dispersant: BYK-LP N 21324 (manufactured by BYK; solid content equivalent) 7.5 parts;
Resin (B): Resin B-1 (solid content equivalent) 4 parts;
Solvent (E): 84.5 parts of propylene glycol monomethyl ether acetate;

(Synthesis example 8)
[Preparation of colored dispersion (CD-3)]
The components were mixed in the following proportions, 300 parts of zirconia beads with a diameter of 0.1 mm were added, and the mixture was shaken. The zirconia beads were removed by filtration to prepare a colored dispersion (CD-3).
Colorant (A): 4 parts of colorant (Ia124);
Dispersant: BYK-LP N 6919 (manufactured by BYK; solid content equivalent) 7.5 parts;
Resin (B): Resin B-1 (solid content equivalent) 4 parts;
Solvent (E): 84.5 parts of propylene glycol monomethyl ether acetate;

(Synthesis example 9)
[Preparation of colored dispersion (CD-4)]
The components were mixed in the following proportions, 300 parts of zirconia beads with a diameter of 0.2 mm were added, and the mixture was shaken. The zirconia beads were removed by filtration to prepare a colored dispersion (CD-4).
Colorant (A): 4 parts of colorant (IIa12);
Dispersant: DISPERBYK-161 (manufactured by BYK; solid content equivalent) 7.5 parts;
Resin (B): Resin B-1 (solid content equivalent) 4 parts;
Solvent (E): 84.5 parts of propylene glycol monomethyl ether acetate;

(Synthesis example 10)
[Preparation of resin B-2]
A suitable amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere, and 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added thereto and heated to 85° C. with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^{2, [6} ] A mixed solution of 25 parts of a mixture of decane-9-yl acrylate (content ratio 1:1 in molar ratio), 137 parts of N-cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added. The mixture was added dropwise over 5 hours. Meanwhile, a solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition was completed, the temperature was maintained at 85°C for 4 hours, and then cooled to room temperature to create a copolymer (resin B-2) solution with a viscosity of 23 mPas and a solid content of 25.6% as measured with a B-type viscometer (23°C). I got it. The weight average molecular weight (Mw) of the obtained copolymer was 8.0×10 ³ , the degree of dispersion was 2.1, and the acid value in terms of solid content was 109 mg-KOH/g. Resin B-2 has the following structural units.

(Examples 1 to 6, Comparative Examples 1 to 4)
[Preparation of colored curable resin composition]
Each component was mixed to have the composition shown in Table 5 to obtain each colored curable resin composition.

In Table 5, each component represents the following compound.
Singlet oxygen quencher (Cu-1): chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I)
Singlet oxygen quencher (Ni-1): Tetramethylammonium bis(3,4,6-trichloro-1,2-benzenedithiolat)nickel Singlet oxygen quencher (Co-1): Bis(2,4-pentane) dionato) cobalt Resin (B-2): Resin B-2 (solid content equivalent)
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; Changzhou Strong Electronics New Materials ( Co., Ltd.)
Solvent (E-1): Propylene glycol monomethyl ether acetate Solvent (E-2): Cyclohexane Solvent (E-3): Diacetone alcohol Leveling agent (F-1): Polyether-modified silicone oil (Toray Dow Corning Co., Ltd. ) manufactured by Toray Silicone SH8400)

[Preparation of color filter (colored coating film)]
A colored curable resin composition was applied onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Inc.) using a spin coating method so that the film thickness after post-baking was 2.0 μm, and then coated at 100° C. for 3 minutes. A composition layer was formed by prebaking. After cooling, the composition layer formed on the substrate was irradiated with light at an exposure dose of 100 mJ/cm ² (365 nm standard) in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). did. After the light irradiation, post-baking was performed at 230° C. for 30 minutes in an oven to obtain a colored coating film. The thickness of the obtained colored coating film was measured using a film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Technology Co., Ltd.), and it was confirmed to be 2.0 μm.

[Lightfastness evaluation]
A UV cut filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co., Ltd.; cuts light of 380 nm or less) was placed on the colored coating film obtained, and a xenon lamp was placed in a light resistance tester (SUNTEST CPS+; manufactured by Toyo Seiki Co., Ltd.). Light was irradiated for 48 hours.
The chromaticity was measured before and after the light fastness test, and the color difference ΔEab ^* was calculated from the measured values by the method described in JIS Z 8730:2009 (7. Color difference calculation method). Note that the smaller the color difference ΔEab ^* , the smaller the color change, and the higher the light resistance. The results are shown in Table 6.

According to the colored curable resin composition of the present invention, a color filter having excellent light resistance can be formed.

Claims (8)

contains a colorant, a resin, a polymerizable compound, a polymerization initiator, and a singlet oxygen quencher, the colorant contains a compound represented by formula (I), and Q ¹ or Q ² in formula (I). is a colored curable resin composition containing at least one --CO ₂ H.

[In the formula,
R ¹ to 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 carbon Represents a monovalent heterocyclic group of numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -O-, -S-, -S(O) ₂ - or -CO-,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ 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 with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -O-, -S-, -S(O) ₂ - or -CO-,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
Q ¹ and Q ² 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 with -Si(-)(-)-,
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -O-, -S-, -S(O) ₂ - or -CO-,
The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
When a plurality of Z ¹ to Z ⁴ , M and MM exist, they may be the same or different from each other. ] The colored curable resin composition according to claim 1, wherein the singlet oxygen quencher is a transition metal complex. The colored curable resin composition according to claim 2, wherein the singlet oxygen quencher is a transition metal complex containing at least one selected from a nickel complex, a copper complex, and a cobalt complex. The colored curable resin according to any one of claims 1 to 3, wherein Q ¹ and Q ² in the formula (I) are each independently a group represented by the formula (QQ1) or the formula (QQ2). Composition.

[In the formula,
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 carbon Represents a monovalent heterocyclic group of numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH ₂ - constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -O-, -S-, -S(O) ₂ - or -CO-,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM.
R ^Q1 to R ^Q4 may each be bonded to one or more members selected from R ^Q1 to R ^Q4 to form a ring,
R ^Q5 to R ^Q10 may each be bonded to one or more members selected from R ^Q5 to R ^Q10 to form a ring.
M and MM represent the same meanings as above.
* indicates a bond. ] The colored curable resin composition according to claim 4, wherein at least one of ^Q1 and ^Q2 in the formula (I) is a group represented by the formula (QQ1). At least one compound containing a colorant, a resin, a polymerizable compound, a polymerization initiator, and a singlet oxygen quencher, wherein the colorant is selected from a compound represented by formula (I) and a compound represented by formula (II). A colored curable resin composition containing seeds.

[In the formula,
R ¹ ～R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM represents 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 with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH constituting the monovalent hydrocarbon group and the monovalent heterocyclic group ₂ - is -O-, -S-, -S(O) ₂ - or -CO- may be substituted,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group are halogen atoms, cyano groups, nitro groups, -SO ₃ M, -CO ₂ It may be replaced with M or MM.
R ¹ and R ² ,R ² and R ³ ,R ³ and R ^Four ,R ^Four and R ⁶ , and R ⁶ and R ^Five may be bonded to each other to form a ring.
M is a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ^Four ) represents.
MM is an alkali metal atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ^Four ) represents.
Z ¹ ～Z ^Four each independently represents 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 with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
-CH constituting the monovalent hydrocarbon group and the monovalent heterocyclic group ₂ - is -O-, -S-, -S(O) ₂ - or -CO- may be substituted,
The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group are halogen atoms, cyano groups, nitro groups, -SO ₃ M, -CO ₂ It may be replaced with M or MM.
Q ¹ represents a divalent hydrocarbon group or a divalent heterocyclic group,
-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N=,
-CH constituting the divalent hydrocarbon group and the divalent heterocyclic group ₂ - is -O-, -S-, -S(O) ₂ - or -CO- may be substituted,
The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group are halogen atoms, cyano groups, nitro groups, -SO ₃ M, -CO ₂ It may be replaced with M or MM.
Q ² represents a group represented by formula (Qa12).

[In the formula, * represents a bond. ]
Z ¹ ～Z ^Four , M, and MM, they may be the same or different from each other. ] A color filter formed from the colored curable resin composition according to any one of claims 1 to 6 . A display device comprising the color filter according to claim 7 .