JP2022129359A - Colored resin composition, compound, color filter, and display device - Google Patents

Abstract

To provide a compound capable of forming a color filter exhibiting good contrast, and a colored resin composition.SOLUTION: The colored resin composition contains a colorant and a resin, where the colorant comprises a compound represented by formula (I).SELECTED DRAWING: None

Description

TECHNICAL FIELD The present invention relates to a compound useful as a dye, a colored resin composition, a color filter and a display device.

Color filters used in display devices such as liquid crystal display devices, electroluminescence display devices and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors are manufactured from colored resin compositions. A perylenetetracarboxylic acid diimide compound is known as a coloring agent contained in such a colored resin composition (Patent Document 1).

JP 2020-079397 A

However, a color filter formed from a colored resin composition using the conventionally known perylenetetracarboxylic acid diimide compound as a coloring agent has not been sufficiently satisfactory in contrast. Accordingly, an object of the present invention is to provide a compound capable of forming a color filter exhibiting good contrast, and a colored resin composition.

［式（Ｉ）中、
Ｒ¹及びＲ²は、互いに独立に、水素原子、－Ｒ^8a、又は－ＳＯ₂－Ｒ^8bを表す。
Ｒ¹とＲ²とは、各々が結合する窒素原子と一緒になって、置換基を有していてもよい環を形成してもよく、該環を構成する－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ－、－Ｓ（Ｏ）₂－、－ＮＨ－、又は－ＮＲ^8g－に置き換わっていてもよい。
Ｒ³～Ｒ⁷は、互いに独立に、水素原子、－Ｒ^8c、－Ｏ－Ｒ^8d、－ＣＯ－Ｏ－Ｒ^8e、－Ｏ－ＣＯ－Ｒ^8f、ハロゲン原子、ヒドロキシ基、カルボキシ基、スルホ基、又はニトロ基を表す。
Ｒ^8a、Ｒ^8b、Ｒ^8c、Ｒ^8d、Ｒ^8e、Ｒ^8f、及びＲ^8gは、互いに独立に、置換基を有していてもよい炭素数１～２０の炭化水素基を表す。
Ｒ^8a、Ｒ^8b、Ｒ^8c、Ｒ^8d、Ｒ^8e、Ｒ^8f、及びＲ^8gが複数存在する場合、それらは同一であってもよく、異なっていてもよい。］
［２］ 式（Ｉ）におけるＲ¹が－ＳＯ₂－Ｒ^8bであり、且つ
Ｒ²が水素原子、又は－Ｒ^8aである［１］に記載の着色樹脂組成物。
［３］ さらに重合性化合物、及び重合開始剤を含有する［１］又は［２］に記載の着色樹脂組成物。
［４］ ［１］～［３］のいずれかに記載の着色樹脂組成物から形成されるカラーフィルタ。
［５］ ［４］に記載のカラーフィルタを含む表示装置。
［６］ 式（ＩＡ）で表される化合物。

［式（ＩＡ）中、
Ｒ¹¹は、置換基を有していてもよい炭素数１～２０の炭化水素基を表す。
Ｒ²は、水素原子、－Ｒ^8a、又は－ＳＯ₂－Ｒ^8bを表す。
Ｒ³～Ｒ⁷は、互いに独立に、水素原子、－Ｒ^8c、－Ｏ－Ｒ^8d、－ＣＯ－Ｏ－Ｒ^8e、－Ｏ－ＣＯ－Ｒ^8f、ハロゲン原子、ヒドロキシ基、カルボキシ基、スルホ基、又はニトロ基を表す。
Ｒ^8a、Ｒ^8b、Ｒ^8c、Ｒ^8d、Ｒ^8e、及びＲ^8fは、互いに独立に、置換基を有していてもよい炭素数１～２０の炭化水素基を表す。
Ｒ^8c、Ｒ^8d、Ｒ^8e、及びＲ^8fが複数存在する場合、それらは同一であってもよく、異なっていてもよい。］ The gist of the present invention is as follows.
[1] A colored resin composition containing a coloring agent and a resin, wherein the coloring agent contains a compound represented by formula (I).

[in the formula (I),
R ¹ and R ² independently represent a hydrogen atom, -R ^8a or -SO ₂ -R ^8b .
R ¹ and R ² may form an optionally substituted ring together with the nitrogen atom to which they are attached, and —CH ₂ — constituting the ring is —O -, -CO-, -S-, -S(O) ₂ -, -NH-, or -NR ^8g -.
R ³ to R ⁷ each independently represent a hydrogen atom, --R ^8c , --OR ^8d , --CO- ^{OR 8e} , --O--CO--R ^8f , a halogen atom, a hydroxy group, a carboxyl group, a sulfo group, or a nitro group.
R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
When a plurality of R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g are present, they may be the same or different. ]
[2] The colored resin composition according to [1], wherein R ¹ in formula (I) is —SO ₂ —R ^8b and R ² is a hydrogen atom or —R ^8a .
[3] The colored resin composition according to [1] or [2], further comprising a polymerizable compound and a polymerization initiator.
[4] A color filter formed from the colored resin composition according to any one of [1] to [3].
[5] A display device including the color filter described in [4].
[6] A compound represented by formula (IA).

[In the formula (IA),
R ¹¹ represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
R ² represents a hydrogen atom, -R ^8a or -SO ₂ -R ^8b .
R ³ to R ⁷ each independently represent a hydrogen atom, --R ^8c , --OR ^8d , --CO- ^{OR 8e} , --O--CO--R ^8f , a halogen atom, a hydroxy group, a carboxyl group, a sulfo group, or a nitro group.
R ^8a , R ^8b , R ^8c , R ^8d , R ^8e and R ^8f each independently represent an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
When multiple R ^8c , R ^8d , R ^8e and R ^8f are present, they may be the same or different. ]

ADVANTAGE OF THE INVENTION According to this invention, the compound which can form the color filter which shows a favorable contrast, and a colored resin composition can be provided.

The colored resin composition of the present invention contains a coloring agent (hereinafter sometimes referred to as coloring agent (A)) and a resin (hereinafter sometimes referred to as resin (B)).
The colored resin composition of the present invention further contains a polymerizable compound (hereinafter sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as a polymerization initiator (D)). good.
The colored resin composition of the present invention may further contain a solvent (hereinafter sometimes referred to as solvent (E)).
The colored resin composition of the present invention may further contain a polymerization initiation aid (hereinafter sometimes referred to as polymerization initiation aid (D1)).
The colored resin composition of the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)).
In this specification, the compounds exemplified as each component can be used singly or in combination, unless otherwise specified.

<Colorant (A)>
Colorant (A) includes a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)).

［式（Ｉ）中、
Ｒ¹及びＲ²は、互いに独立に、水素原子、－Ｒ^8a、又は－ＳＯ₂－Ｒ^8bを表す。
Ｒ¹とＲ²とは、各々が結合する窒素原子と一緒になって、置換基を有していてもよい環を形成してもよく、該環を構成する－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ－、－Ｓ（Ｏ）₂－、－ＮＨ－、又は－ＮＲ^8g－に置き換わっていてもよい。
Ｒ³～Ｒ⁷は、互いに独立に、水素原子、－Ｒ^8c、－Ｏ－Ｒ^8d、－ＣＯ－Ｏ－Ｒ^8e、－Ｏ－ＣＯ－Ｒ^8f、ハロゲン原子、ヒドロキシ基、カルボキシ基、スルホ基、又はニトロ基を表す。
Ｒ^8a、Ｒ^8b、Ｒ^8c、Ｒ^8d、Ｒ^8e、Ｒ^8f、及びＲ^8gは、互いに独立に、置換基を有していてもよい炭素数１～２０の炭化水素基を表す。
Ｒ^8a、Ｒ^8b、Ｒ^8c、Ｒ^8d、Ｒ^8e、Ｒ^8f、及びＲ^8gが複数存在する場合、それらは同一であってもよく、異なっていてもよい。］ <<Compound (I)>>

[in the formula (I),
R ¹ and R ² independently represent a hydrogen atom, -R ^8a or -SO ₂ -R ^8b .
R ¹ and R ² may form an optionally substituted ring together with the nitrogen atom to which they are attached, and —CH ₂ — constituting the ring is —O -, -CO-, -S-, -S(O) ₂ -, -NH-, or -NR ^8g -.
R ³ to R ⁷ each independently represent a hydrogen atom, --R ^8c , --OR ^8d , --CO- ^{OR 8e} , --O--CO--R ^8f , a halogen atom, a hydroxy group, a carboxyl group, a sulfo group, or a nitro group.
R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
When a plurality of R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g are present, they may be the same or different. ]

Examples of hydrocarbon groups having 1 to 20 carbon atoms represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. be done. Aliphatic hydrocarbon groups may be saturated or unsaturated and may be linear or alicyclic.

Saturated or unsaturated chain hydrocarbon groups represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group and icosyl group. Alkyl group; isopropyl group, (1-ethyl)propyl group, isobutyl group, sec-butyl group, tert-butyl group, (3-methyl)butyl group, (1-methyl)butyl group, (1-ethyl)butyl group , (2-methyl)butyl group, (2-ethyl)butyl group, (1-propyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl)pentyl group, (3-methyl)pentyl group, (1-ethyl)pentyl group, (2-ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, (2-propyl)pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (1-ethyl)hexyl group, (2-ethyl)hexyl group, (1-propyl)hexyl group, (2-propyl)hexyl group , (1-butyl) hexyl group, (2-butyl) hexyl group, (1-pentyl) hexyl group, (2-methyl) heptyl group, (2-ethyl) heptyl group, (3-ethyl) heptyl group, ( 2-propyl)heptyl group, (1-butyl)heptyl group, (2-butyl)heptyl group, (1-pentyl)heptyl group, (2-pentyl)heptyl group, (1-hexyl)heptyl group, (2- methyl) octyl group, (2-ethyl) octyl group, (2-propyl) octyl group, (2-butyl) octyl group, (1-pentyl) octyl group, (2-pentyl) octyl group, (1-hexyl) Octyl group, (2-hexyl) octyl group, (1-heptyl) octyl group, (2-ethyl) nonyl group, (2-propyl) nonyl group, (2-butyl) nonyl group, (2-pentyl) nonyl group , (1-hexyl) nonyl group, (2-hexyl) nonyl group, (1-heptyl) nonyl group, (1-octyl) nonyl group, (2-propyl) decyl group, (2-butyl) decyl group, ( 2-pentyl)decyl group, (2-hexyl)decyl group, (1-heptyl)decyl group, (2-butyl ) branched chain alkyl groups such as undecyl group; vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl) ethenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, alkenyl group such as 2-pentenyl group; and the like. The number of carbon atoms in the saturated chain hydrocarbon group is preferably 1-18, more preferably 1-16, even more preferably 1-15. The unsaturated chain hydrocarbon group preferably has 2 to 18 carbon atoms, more preferably 2 to 16 carbon atoms, and still more preferably 2 to 15 carbon atoms.

Saturated or unsaturated alicyclic hydrocarbon groups represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g include cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group. , cycloheptyl group, cycloalkyl group such as cyclooctyl group; cyclohexenyl group (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl group, cycloalkenyl group such as cyclooctenyl group; norbornyl group, adamantyl group, bicyclo[2.2.2]octyl group and the like. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 16 carbon atoms, and still more preferably 3 to 15 carbon atoms.

Aromatic hydrocarbon groups represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g include phenyl, 1-naphthyl, 2-naphthyl, phenanthryl and anthryl. groups, pyrenyl groups, and the like. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6-20, more preferably 6-18, even more preferably 6-15.

The hydrocarbon groups represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f , and R ^8g are the chain hydrocarbon groups listed above as long as the upper limit of the number of carbon atoms is 20 or less. , an alicyclic hydrocarbon group, and an aromatic hydrocarbon group.
Such a group may be, for example, a combination of an aromatic hydrocarbon group and at least one group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group and an aromatic hydrocarbon group, In the hydrocarbon group resulting from the combination, a chain hydrocarbon group may be combined as a divalent group (eg, an alkanediyl group). Examples of combined hydrocarbon groups include benzyl, phenethyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 2-naphthylmethyl, diphenylmethyl, 2,2-diphenylethyl, aralkyl groups such as 3,3-diphenylpropyl group and 4,4-diphenylbutyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group); arylalkynyl groups such as phenylethynyl group; -tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group , 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropyl phenyl group, p-isopropylphenyl group, 2,3-diisopropylphenyl group, 2,4-diisopropylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisopropylphenyl group, 3,5-diisopropylphenyl group, 2 , 4,6-triisopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 2,6-di(tert-butyl) phenyl group, 3,5-di(tert-butyl)phenyl group, 3,6-di(tert-butyl)phenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 4-pentylphenyl group, 4 - Alkylaryl groups such as octylphenyl group, 4-(2,4,4-trimethyl-2-pentyl)phenyl group, 2-dodecylphenyl group, 3-dodecylphenyl group and 4-dodecylphenyl group; o-tolylmethyl group , m-tolylmethyl group, p-tolylmethyl group, 2-ethylphenylmethyl group, 3-ethylphenylmethyl group, 4-ethylphenylmethyl group, 2,3-dimethylphenylmethyl group, 2,4-dimethylphenylmethyl group, 2,5-dimethylphenylmethyl group, 2,6-dimethylphenylmethyl group, 3,4-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2,4,6-trimethylphenylmethyl group, 4-vinyl phenylmethyl group, o-isopropylphenylmethyl group, m-isopropylphenylmethyl group, p-isopropylphenyl Alkyl such as methyl group, 2,3-diisopropylphenylmethyl group, 2,4-diisopropylphenylmethyl group, 2,5-diisopropylphenylmethyl group, 2,6-diisopropylphenylmethyl group and 3,5-diisopropylphenylmethyl group Arylalkyl group; 2,3-dihydro-4-indenyl group, 1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 8-methyl-1,2,3,5,6, 7-hexahydro-4-s-indacenyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, 3-methyl-5,6,7 ,8-tetrahydro-2-naphthyl group, 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group and other alkanediyl group-bonded aryl groups; biphenylyl group, aryl group to which one or more aryl groups such as terphenylyl group are bonded; cyclohexylmethylphenyl group, benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group and the like.
The hydrocarbon group may be, for example, a hydrocarbon group formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, examples of which include a 1-methylcyclopropyl group, a 2-methylcyclopentyl group, 3-methylcyclopentyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4- dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3 , 3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 4-cyclohexylcyclohexyl group, and other alicyclic hydrocarbon groups bonded with one or more alkyl groups; cyclopropylmethyl group , a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, an adamantylmethyl group, etc., to which one or more alicyclic hydrocarbon groups are bonded. group, 2-methylcyclopropylmethyl group, 2-methylcyclobutylmethyl group, 3-methylcyclobutylmethyl group, 2-methylcyclopentylmethyl group, 3-methylcyclopentylmethyl group, 2-methylcyclohexylmethyl group, 3-methyl Examples thereof include an alkyl group to which an alicyclic hydrocarbon group to which one or more alkyl groups such as a cyclohexylmethyl group and a 4-methylcyclohexylmethyl group are bonded.
The number of carbon atoms in a group obtained by combining two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups is preferably 4 to 20, more preferably 5 to 18, and even more preferably 6 to 16. .

—SO ₂ —R ^8b includes, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, heptylsulfonyl, octylsulfonyl, nonylsulfonyl and decylsulfonyl groups. , isopropylsulfonyl group, (1-ethyl)propylsulfonyl group, sec-butylsulfonyl group, isobutylsulfonyl group, tert-butylsulfonyl group, (3-methyl)butylsulfonyl group, (1-methyl)butylsulfonyl group, (1 -ethyl)butylsulfonyl group, (2-methyl)butylsulfonyl group, (2-ethyl)butylsulfonyl group, (1-propyl)butylsulfonyl group, isopentylsulfonyl group, neopentylsulfonyl group, tert-pentylsulfonyl group, (2-methyl)pentylsulfonyl group, (3-methyl)pentylsulfonyl group, (1-ethyl)pentylsulfonyl group, (2-ethyl)pentylsulfonyl group, (3-ethyl)pentylsulfonyl group, (1-propyl) pentylsulfonyl group, (1-butyl)pentylsulfonyl group, (2-propyl)pentylsulfonyl group, (2-ethyl)hexylsulfonyl group, cyclopropylsulfonyl group, cyclobutylsulfonyl group, cyclopentylsulfonyl group, cyclohexylsulfonyl group, cyclo heptylsulfonyl group, cyclooctylsulfonyl group, 2-methylcyclopentylsulfonyl group, 3-methylcyclopentylsulfonyl group, 2-methylcyclohexylsulfonyl group, 3-methylcyclohexylsulfonyl group, 4-methylcyclohexylsulfonyl group, cyclopentylmethylsulfonyl group, cyclopentyl ethylsulfonyl group, cyclohexylmethylsulfonyl group, cyclohexylethylsulfonyl group, 2-methylcyclopentylmethylsulfonyl group, 3-methylcyclopentylmethylsulfonyl group, 2-methylcyclohexylmethylsulfonyl group, 3-methylcyclohexylmethylsulfonyl group, 4-methylcyclohexyl methylsulfonyl group, phenylsulfonyl group, benzylsulfonyl group, phenethylsulfonyl group, 1-naphthylmethylsulfonyl group, 2-naphthylmethylsulfonyl group, o-tolylsulfonyl group, m-tolylsulfonyl group, p-tolylsulfonyl group 2,3 -dimethylphenylsulfonyl group, 2,4-dimethylphenylsulfonyl group , 2,5-dimethylphenylsulfonyl group, 2,6-dimethylphenylsulfonyl group, 3,4-dimethylphenylsulfonyl group, 3,5-dimethylphenylsulfonyl group, o-tolylmethylsulfonyl group, m-tolylmethylsulfonyl group , p-tolylmethylsulfonyl group, 2,3-dimethylphenylmethylsulfonyl group, 2,4-dimethylphenylmethylsulfonyl group, 2,5-dimethylphenylmethylsulfonyl group, 2,6-dimethylphenylmethylsulfonyl group, 3, 4-dimethylphenylmethylsulfonyl group, 3,5-dimethylphenylmethylsulfonyl group and the like.

—OR ^8d includes, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group and a heptyloxy group. , octyloxy group, nonyloxy group, decyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyloxy group and the like. .

—CO—O—R ^8e includes, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, and (2-ethyl)hexyl. oxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group and the like.

—O—CO—R ^8f includes, for example, acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, nonanoyloxy group, decanoyloxy group, benzoyloxy group and the like.

Substituents which the hydrocarbon groups having 1 to 20 carbon atoms represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g may have include, for example, halogen atoms ; -O-, -CO-, and at least one selected from the group consisting of a divalent hydrocarbon group (including at least one -O- or -CO-) and a monovalent hydrocarbon group in combination A group; nitrile group; nitro group; amino group; amide group; sulfonamide group; hydroxy group; thiol group; arylthio group having 6 to 20 carbon atoms such as 2-naphthylthio group; sulfoxy group; alkylsulfoxy group having 1 to 15 carbon atoms such as methylsulfoxy group and ethylsulfoxy group; phenylsulfoxy group and 1-naphthyl arylsulfoxy group having 6 to 20 carbon atoms such as sulfoxy group and 2-naphthylsulfoxy group; silyl group; boryl group; monomethylamino group, dimethylamino group, monoethylamino group, diethylamino group and the like. 15 alkylamino groups; arylamino groups having 6 to 20 carbon atoms such as monophenylamino group and diphenylamino group; aralkylamino groups having 7 to 20 carbon atoms such as benzylamino group; N-methylaminosulfonyl group, N, Alkylaminosulfonyl groups having 1 to 15 carbon atoms such as N-dimethylaminosulfonyl group and N-ethylaminosulfonyl group; carboxy group; carbamoyl group; heterocyclic ring having 1 to 20 carbon atoms such as furyl group, pyrrolyl group and thienyl group and the like.

Halogen atoms include fluorine, chlorine, bromine and iodine atoms.

combining at least one selected from the group consisting of -O-, -CO-, and divalent hydrocarbon groups (including at least one -O- or -CO-) and a monovalent hydrocarbon group; Examples of the group include groups represented by the following formulas (Sa) and (Sb).

［式（Ｓａ）、式（Ｓｂ）中、
Ｒ^Sは、炭素数１～２０の炭化水素基を表し、該炭化水素基に含まれメチレン基は、－Ｏ－及び／又は－ＣＯ－に置き換わっていてもよい。
＊は結合手を表す。］

[In formula (Sa) and formula (Sb),
R ^S represents a hydrocarbon group having 1 to 20 carbon atoms, and methylene groups contained in the hydrocarbon group may be replaced with -O- and/or -CO-.
* represents a bond. ]

The hydrocarbon group having 1 to 20 carbon atoms represented by R ^S is the same as the hydrocarbon group represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g above. Examples include:
When the methylene group contained in the hydrocarbon group represented by R ^S is replaced with —O— and/or —CO—, the number thereof may be one, or two or more. When a methylene group contained in a hydrocarbon group is replaced with -O- and/or -CO-, the number of carbon atoms before replacement is the number of carbon atoms in the hydrocarbon group.

Specific examples of the group represented by the formula (Sa) include alkoxy groups having 1 to 15 carbon atoms such as a methoxy group and an ethoxy group; Examples thereof include aryloxy groups having 6 to 20 carbon atoms. Specific examples of groups represented by formula (Sb) include alkylcarbonyl groups having 2 to 15 carbon atoms such as acetyl group and propionyl group; benzoyl group, 1-naphthylcarbonyl group, 2-naphthylcarbonyl group and the like arylcarbonyl group having 7 to 20 carbon atoms; alkoxycarbonyl group having 2 to 15 carbon atoms such as methoxycarbonyl group and ethoxycarbonyl group; carbon such as phenyloxycarbonyl group, 1-naphthyloxycarbonyl group and 2-naphthyloxycarbonyl group Examples include aryloxycarbonyl groups of numbers 7 to 19, and the like.

The substituent which the hydrocarbon group having 1 to 20 carbon atoms represented by R ^8a and R ^8c may have is selected from the group consisting of —O—, —CO— and a divalent hydrocarbon group. A group obtained by combining at least one (including at least one -O- or -CO-) with a monovalent hydrocarbon group, a carboxy group is preferred, and is represented by the above (Sa) and formula (Sb) more preferably an alkoxy group having 1 to 15 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a carboxy group, an alkylcarbonyl group having 2 to 15 carbon atoms, an arylcarbonyl group having 7 to 20 carbon atoms, An alkoxycarbonyl group having 2 to 15 carbon atoms and an aryloxycarbonyl group having 7 to 19 carbon atoms are more preferable, and a carboxy group, an alkylcarbonyl group having 2 to 15 carbon atoms, an arylcarbonyl group having 7 to 20 carbon atoms, and 2 carbon atoms. An alkoxycarbonyl group having 1 to 15 carbon atoms and an aryloxycarbonyl group having 7 to 19 carbon atoms are more preferable, a carboxy group and an alkoxycarbonyl group having 2 to 15 carbon atoms are more preferable, and an alkoxycarbonyl group having 2 to 10 carbon atoms are more preferable. An alkoxycarbonyl group having 2 to 5 carbon atoms is particularly preferred.

The substituent which the hydrocarbon group having 1 to 20 carbon atoms represented by R ^8b may have is preferably a halogen atom, more preferably a fluorine atom. When the substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R ^8b is a halogen atom, all the hydrogen atoms of the carbon atoms to which the halogen atoms are bonded are substituted with halogen atoms. is preferred.

When the hydrocarbon groups represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g have substituents, the number of substituents may be 1 or 2 or more. and two or more substituents may be the same or different independently of each other. When the hydrocarbon group represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g has two or more halogen atoms as substituents, two or more substituents are preferably the same. When the hydrocarbon groups represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g have substituents, the number of substituents is preferably one.

R ¹ is preferably -R ^8a or -SO ₂ -R ^8b , more preferably -SO ₂ -R ^8b .

R ^8a in R ¹ is an optionally substituted saturated chain hydrocarbon group, an optionally substituted saturated alicyclic hydrocarbon group, or an optionally substituted Aromatic hydrocarbon groups, groups in which aromatic hydrocarbon groups optionally having substituents and chain hydrocarbon groups are combined, chain hydrocarbon groups optionally having substituents and alicyclic groups It is preferably a group combined with a hydrocarbon group, a saturated chain hydrocarbon group optionally having a substituent, a saturated alicyclic hydrocarbon group optionally having a substituent, a substituent A group obtained by combining an aromatic hydrocarbon group which may have a substituent and a chain hydrocarbon group, and a group obtained by combining a chain hydrocarbon group which may have a substituent and an alicyclic hydrocarbon group. It is more preferable to have a saturated chain hydrocarbon group which may have a substituent, a saturated alicyclic hydrocarbon group which may have a substituent, an aromatic which may have a substituent Groups in which a hydrocarbon group and a chain hydrocarbon group are combined are more preferable, and saturated chain hydrocarbon groups, saturated alicyclic hydrocarbon groups, and aromatic hydrocarbon groups which may have a substituent are more preferable. and a chain hydrocarbon group are more preferred. The number of carbon atoms in the saturated chain hydrocarbon group as R ^8a in R ¹ is preferably 1-18, more preferably 1-16, still more preferably 1-15, and even more preferably 2-15. The number of carbon atoms in the saturated alicyclic hydrocarbon group as R ^8a in R ¹ is preferably 3-18, more preferably 3-16, still more preferably 3-15, and even more preferably 3-10. The number of carbon atoms in the aromatic hydrocarbon group as R ^8a in R ¹ is preferably 6-18, more preferably 6-15, even more preferably 6-12, and even more preferably 6-10. The number of carbon atoms in the group obtained by combining an aromatic hydrocarbon group and a chain hydrocarbon group as R ^8a in R ¹ is preferably 4 to 20, more preferably 5 to 18, still more preferably 6 to 16, and 7 to 16 is even more preferred.
Further, from the viewpoint of improving solubility of compound (I) in a solvent and reducing sublimability, the number of carbon atoms in the hydrocarbon group represented by R ^8a in R ¹ is preferably 5 or more, more preferably 9 or more. .

R ^8b in R ¹ is a saturated chain hydrocarbon group optionally having substituent(s), an aromatic hydrocarbon group optionally having substituent(s), an aromatic hydrocarbon group optionally having substituent(s) A group in which a hydrocarbon group and a chain hydrocarbon group are combined is preferable, and a saturated chain hydrocarbon group which may have a substituent, an aromatic hydrocarbon group which may have a substituent and more preferably a saturated chain hydrocarbon group or an aromatic hydrocarbon group. The number of carbon atoms in the saturated chain hydrocarbon group as R ^8b in R ¹ is preferably from 1 to 18, more preferably from 1 to 16, still more preferably from 1 to 15, even more preferably from 1 to 10, and from 1 to 5. Especially preferred. The number of carbon atoms in the aromatic hydrocarbon group as R ^8b in R ¹ is preferably 6 to 20, more preferably 6 to 18, still more preferably 6 to 15, even more preferably 6 to 10, and particularly 6 to 8. preferable. The number of carbon atoms in the group obtained by combining an aromatic hydrocarbon group and a chain hydrocarbon group as R ^8b in R ¹ is preferably 4 to 20, more preferably 5 to 18, still more preferably 6 to 16, and 7 to 16 is even more preferred.

Specific examples of R ¹ include the following formulas (D-1) to (D-69), formulas (E-1) to (E-25), and formulas (G-1) to (G- 31), groups represented by formulas (H-1) to (H-53) are preferable, and formulas (D-1) to (D-18), formulas (D-40) to formulas (D-69 ), formula (E-2) ~ formula (E-4), formula (E-6) ~ formula (E-8), formula (E-10) ~ formula (E-12), formula (E-14) ~ Formula (E-16), Formula (E-18) ~ Formula (E-20), Formula (G-2) ~ Formula (G-27), Formula (H-1) ~ Formula (H-53) Groups represented by formula (H-1) to formula (H-53) are more preferable, and groups represented by formula (H-1) to formula (H-5) and formula (H-19) are more preferable. ~ formula (H-30), formula (H-39) ~ formula (H-53) is more preferably a group represented by formula (H-1) ~ formula (H-5), formula (H-19 ) to formula (H-30) are more preferred. In the formula, * represents a bond.

R ² is preferably a hydrogen atom or -R ^8a , more preferably a hydrogen atom.
R ^8a in R ² is preferably an optionally substituted saturated chain hydrocarbon group, more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, and 1 to 5 saturated chain hydrocarbon groups are more preferred.

The ring formed by R ¹ and R ² together with the nitrogen atoms to which they are bonded may be saturated or unsaturated, and may be monocyclic or polycyclic.

The number of ring members of the ring formed by R ¹ and R ² together with the nitrogen atoms to which they are bonded is preferably 3-15, more preferably 4-12, and even more preferably 5-10.

Specific examples of the ring formed by R ¹ and R ² together with the nitrogen atom to which they are attached include rings represented by the following formulas (J-1) to (J-9). mentioned. In the formula, * represents a bond.

The ring in which —CH ₂ — constituting a ring formed by R ¹ and R ² together with the nitrogen atoms to which they are attached is replaced with —O— is specifically represented by the following formula (Ja -1) to rings represented by formulas (Ja-6). In the formula, * represents a bond.

Specific examples of the ring in which —CO— is substituted for —CH ₂ — forming a ring formed by R ¹ and R ² together with the nitrogen atoms to which they are attached, include the following formula (Jb- 1) to the ring represented by formula (Jb-6). In the formula, * represents a bond.

Specific examples of the ring in which —S— is substituted for —CH ₂ — forming a ring formed by R ¹ and R ² together with the nitrogen atoms to which they are attached, include the following formula (Jc -1) to rings represented by formulas (Jc-6). In the formula, * represents a bond.

Specific examples of the ring in which —S(O) ₂ — is substituted for —CH ₂ — constituting a ring formed by R ¹ and R ² together with the nitrogen atoms to which they are attached, include: Examples include rings represented by the following formulas (Jd-1) to (Jd-6). In the formula, * represents a bond.

Specifically, the ring in which —NH— is substituted for —CH ₂ — constituting a ring formed by R ¹ and R ² together with the nitrogen atom to which they are attached, is represented by the following formula (Je -1) to rings represented by formulas (Je-6). In the formula, * represents a bond.

Specific examples of the ring in which —NR ^8g — is substituted for —CH ₂ — constituting a ring formed by R ¹ and R ² together with the nitrogen atom to which they are attached, include the following formula ( Jf-1) to the rings represented by formulas (Jf-6). In the formula, * represents a bond.

R ^8g is a saturated chain hydrocarbon group optionally having substituent(s), an aromatic hydrocarbon group optionally having substituent(s), an aromatic hydrocarbon group optionally having substituent(s) and a chain hydrocarbon group, a saturated chain hydrocarbon group optionally having a substituent, an aromatic hydrocarbon group optionally having a substituent is more preferable, and saturated chain hydrocarbon groups and aromatic hydrocarbon groups are further preferable. The number of carbon atoms in the saturated chain hydrocarbon group for R ^8g is preferably 1-18, more preferably 1-16, even more preferably 1-15, even more preferably 1-10, and particularly preferably 1-5. The number of carbon atoms in the aromatic hydrocarbon group for R ^8g is preferably 6-20, more preferably 6-18, still more preferably 6-15, even more preferably 6-10, and particularly preferably 6-8. The number of carbon atoms in the group in which an aromatic hydrocarbon group and a chain hydrocarbon group are combined as R ^8g is preferably 4 to 20, more preferably 5 to 18, still more preferably 6 to 16, and more preferably 7 to 16. More preferred.

Specific examples of the ring represented by the above formula (Jf-3) include rings represented by the following formulas (Jf-3-1) to (Jf-3-6). In the formula, * represents a bond.

The ring formed by R ¹ and R ² together with the nitrogen atom to which they are bonded includes the ring represented by the above formula (J-4) and the ring represented by the above formula (J-4). is replaced with -O-, -CO-, -S-, -S(O) ₂ -, _-NH- or -NR ^8g -, and the above formula (J-4 ), formula (Jc-3), formula (Je-3), and formula (Jf-3) are more preferred.

The substituents that the ring formed by R ¹ and R ² together with the nitrogen atoms to which they are bonded may have include R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R The same examples as the substituents that ^8f and R ^8g may have can be mentioned. When the ring formed by R ¹ and R ² together with the nitrogen atom to which each is attached has a substituent, the number of substituents may be 1, 2 or more, or 2 The above substituents may be the same or different independently of each other.

R ³ to R ⁷ are preferably a hydrogen atom or -R ^8c , more preferably a hydrogen atom.
R ^8c is preferably an optionally substituted saturated chain hydrocarbon group, more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms.

Examples of the compound (I) include compounds represented by the following formula (Ii), wherein the combination of R ¹ and R ² is any one of Tables 1 to 9 below, and compounds represented by the following formula (III) in the compounds wherein R ¹² (the ring formed by R ¹ and R ² in formula (I) together with the nitrogen atom to which each is attached) is any one of the compounds shown in Table 10 below. . In Tables 1 to 10, H is a hydrogen atom, Me is a methyl group, Et is an ethyl group, IBu is an isobutyl group, D-1 to D-69, E-1 to E-25, G -1 to G-31, H-1 to H-53 are respectively the above formulas (D-1) to (D-69), formulas (E-1) to formulas (E-25), formulas (G -1) ~ formula (G-31), the groups represented by formula (H-1) ~ formula (H-53), J-4, J-7, J-9, Ja-3, Jb-3 , Jc-3, Jd-3, Je-3, Jf-3-1 to Jf-3-6 are respectively the above formulas (J-4), formulas (J-7), formulas (J-9), Formula (Ja-3), Formula (Jb-3), Formula (Jc-3), Formula (Jd-3), Formula (Je-3), Formula (Jf-3-1) ~ Formula (Jf-3- It means a ring represented by 6).

［式（Ｉｉｉ）中、Ｒ¹²は、Ｒ¹とＲ²とが、各々が結合する窒素原子と一緒になって形成する環を表す。］

[In formula (Iii), R ¹² represents a ring formed by R ¹ and R ² together with the nitrogen atom to which they are bonded. ]

Compound (I) is preferably compound (I-1) to compound (I-326), more preferably compound (I-1) to compound (I-163), compound (I-1) to compound (I -18), compound (I-40) to compound (I-69), compound (I-71) to compound (I-73), compound (I-75) to compound (I-77), compound (I- 79) ~ Compound (I-81), Compound (I-83) ~ Compound (I-85), Compound (I-87) ~ Compound (I-89), Compound (I-96) ~ Compound (I-121 ), more preferably compound (I-126) to compound (I-163), still more preferably compound (I-126) to compound (I-163), compound (I-126) to compound (I-130) , compounds (I-144) to (I-155) are more preferred.

Further, as the compound (I),
Compounds (I-1) to (I-726) are preferred,
Compound (I-1) to compound (I-163), compound (I-327) to compound (I-667), compound (I-713) to compound (I-726) are more preferred,
Compound (I-1) ~ Compound (I-18), Compound (I-40) ~ Compound (I-69), Compound (I-71) ~ Compound (I-73), Compound (I-75) ~ Compound (I-77), compound (I-79) to compound (I-81), compound (I-83) to compound (I-85), compound (I-87) to compound (I-89), compound ( I-95) ~ compound (I-121), compound (I-126) ~ compound (I-163), compound (I-327) ~ compound (I-344), compound (I-366) ~ compound (I -395), compound (I-397) to compound (I-399), compound (I-401) to compound (I-403), compound (I-405) to compound (I-407), compound (I- 409) ~ compound (I-411), compound (I-413) ~ compound (I-415), compound (I-421) ~ compound (I-447), compound (I-452) ~ compound (I-507 ), compound (I-529) ~ compound (I-558), compound (I-560) ~ compound (I-562), compound (I-564) ~ compound (I-566), compound (I-568) ~ compound (I-570), compound (I-572) ~ compound (I-574), compound (I-576) ~ compound (I-578), compound (I-584) ~ compound (I-610), Compounds (I-615) to (I-726) are more preferred,
Compound (I-126) ~ Compound (I-163), Compound (I-653) ~ Compound (I-667) are more preferred,
Compounds (I-126) to (I-130), compounds (I-144) to (I-155), and compounds (I-653) to (I-661) are more preferred.

In one aspect of the present invention, a compound represented by the following formula (IA) in which R ¹ in formula (I) is —SO ₂ —R ^8b (hereinafter sometimes referred to as compound (IA)) For example, a color filter formed from a colored resin composition containing the novel compound can have good contrast.

［式（ＩＡ）中、
Ｒ¹¹は、置換基を有していてもよい炭素数１～２０の炭化水素基を表す。
Ｒ²～Ｒ⁷は、前記と同じ意味を表す。］

[In the formula (IA),
R ¹¹ represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
R ² to R ⁷ have the same meanings as above. ]

Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R ¹¹ include the same examples as the hydrocarbon groups represented by R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g . The same applies to the preferred carbon number range.

Substituents which the hydrocarbon group having 1 to 20 carbon atoms represented by R ¹¹ may have include R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g . Examples are the same as those of the substituent which the hydrocarbon group having 1 to 20 carbon atoms may have. The substituent which the hydrocarbon group having 1 to 20 carbon atoms represented by R ¹¹ may have is preferably a halogen atom, more preferably a fluorine atom. When the substituent possessed by the hydrocarbon group having 1 to 20 carbon atoms represented by R ¹¹ is a halogen atom, all hydrogen atoms possessed by the carbon atoms to which the halogen atoms are bonded are substituted with halogen atoms. is preferred.

R ¹¹ is a saturated chain hydrocarbon group optionally having substituent(s), an aromatic hydrocarbon group optionally having substituent(s), an aromatic hydrocarbon group optionally having substituent(s) and a chain hydrocarbon group, a saturated chain hydrocarbon group optionally having a substituent, an aromatic hydrocarbon group optionally having a substituent is more preferable, more preferably a saturated chain hydrocarbon group or an aromatic hydrocarbon group, a saturated chain hydrocarbon group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms is more preferred, and a saturated linear hydrocarbon group having 1 to 5 carbon atoms and an aromatic hydrocarbon group having 6 to 8 carbon atoms are particularly preferred.

Compound (I) is represented by the following formula (pt2), for example, by reacting a compound represented by the following formula (pt1) (hereinafter sometimes referred to as compound (pt1)) with malononitrile in a solvent. A compound (hereinafter sometimes referred to as compound (pt2)) is produced, and the compound (pt2) is subjected to a condensation reaction in a solvent using a catalyst to obtain a compound represented by the following formula (pt3) (hereinafter, compound ( pt3)), and further reacting the compound (pt3) with a compound represented by the following formula (MA1) (hereinafter sometimes referred to as compound (MA1)) in a solvent. be able to.

［式中、Ｒ¹～Ｒ⁷は、上述の定義と同一である。Ｒ^Aは、水素原子又はハロゲン原子を表す。］

[In the formula, R ¹ to R ⁷ are the same as defined above. ^RA represents a hydrogen atom or a halogen atom. ]

Halogen atoms represented by ^RA include fluorine, chlorine, bromine and iodine atoms. ^RA is preferably a bromine atom or a hydrogen atom, more preferably a hydrogen atom.

Examples of the compound (pt1) include acenaphthenequinone, 6-bromoacenaphthenequinone and the like.

The amount of malononitrile to be used is generally 0.1 mol or more and 500 mol or less, preferably 0.3 mol or more and 400 mol or less, more preferably 0.5 mol or more, per 1 mol of compound (pt1). It is 300 mol or less, more preferably 0.8 mol or more and 200 mol or less.

As the solvent in the reaction between the compound (pt1) and malononitrile, it is preferable to use a solvent (particularly an organic solvent) that has been sufficiently deoxidized and/or dehydrated in order to suppress side reactions, and dehydrated acetonitrile is more preferred.

The amount of the solvent used in the reaction of the compound (pt1) and malononitrile is usually 0.1-1000 parts by mass per 1 part by mass of the compound (pt1).

The reaction temperature for reacting the compound (pt1) with malononitrile is usually -100°C or higher and 300°C or lower. The reaction time for reacting the compound (pt1) with malononitrile is usually 0.5 hours to 300 hours.

Examples of the compound (pt2) include 2-(2-oxo-2H-acenaphthylene-1-ylidene)-malononitrile, 2-(6-bromo-2-oxo-2H-acenaphthylene-1-ylidene)-malononitrile, and the like. mentioned.

Catalysts used for the production of compound (pt3) include tris(dibenzylideneacetone)dipalladium(0), bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, palladium(II) chloride, tetra sodium chloropalladium (II), palladium (II) (π-cinnamyl) chloride (dimer), allyl palladium (II) chloride (dimer), bis (benzonitrile) palladium (II) dichloride, bis (acetonitrile) palladium (II) ) Palladium compounds such as dichloride; triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, N,N-diisopropylethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,5- Organic bases such as diazabicyclo[4.3.0]-5-nonene, 1,8-diazabicyclo[5.4.0]-7-undecene; sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert- Metal alkoxides such as butoxide; sodium acetate, potassium phosphate, lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate, carbonate Inorganic bases such as potassium hydrogen and cesium hydrogen carbonate are included. Preferably, cesium carbonate, potassium carbonate, potassium phosphate, triethylamine, 4-(N,N-dimethylamino)pyridine, N,N-diisopropylethylamine, 1,4-diazabicyclo[2.2.2]octane, tris ( dibenzylideneacetone)dipalladium(0), palladium(II) acetate.

The amount of the catalyst used in the condensation reaction of the compound (pt2) may be a catalytic amount, for example, 0.1 mol or more and 50 mol or less, preferably 0.5 mol or more, relative to 100 mol of the compound (pt2). It is 40 mol or less, more preferably 1.0 mol or more and 30 mol or less.

When using a metal catalyst such as a palladium compound as a catalyst in the condensation reaction of the compound (pt2), a specific ligand may be coordinated to the metal catalyst. Examples of ligands include trimethylphosphine, triethylphosphine, tri(n-butyl)phosphine, tri(isopropyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, diphenyl(methyl)phosphine, triphenylphosphine, 2-dicyclohexylphosphinobiphenyl, 2-dicyclohexylphosphino-2'-methylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 2-dicyclohexylphosphino-2'-(N,N'-dimethyl amino)biphenyl, 2-diphenylphosphino-2'-(N,N'-dimethylamino)biphenyl and the like.

The amount of the ligand used in the condensation reaction of the compound (pt2) is, for example, 0.05 mol or more and 100 mol or less, preferably 0.1 mol or more and 80 mol or less, relative to 1 mol of the metal catalyst, It is more preferably 0.5 mol or more and 50 mol or less, and still more preferably 0.8 mol or more and 30 mol or less.

Solvents in the condensation reaction of the compound (pt2) in the presence of a catalyst include water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, alcohol solvents such as 1-heptanol, 2-ethyl-1-hexanol, 1-octanol and phenol; ether solvents such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and diethylene glycol dimethyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ethyl acetate aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene; N,N-dimethylformamide, N amide solvents such as methylpyrrolidone; sulfoxide solvents such as dimethylsulfoxide; carboxylic acid solvents such as acetic acid, propionic acid and butyric acid; , diethylene glycol dimethyl ether are more preferred, and water and acetonitrile are even more preferred.

The amount of the solvent used in the condensation reaction of compound (pt2) in the presence of a catalyst is usually 0.1 to 1000 parts by mass per 1 part by mass of compound (pt2).

The reaction temperature in the condensation reaction of compound (pt2) in the presence of a catalyst is usually -100°C or higher and 300°C or lower. The reaction time for the condensation reaction of compound (pt2) in the presence of a catalyst is usually 0.5 hours to 300 hours.

Examples of the compound (pt3) include 1-oxo-1H-phenalene-2,3-dicarbonitrile, 6-bromo-1-oxo-1H-phenalene-2,3-dicarbonitrile and the like.

Examples of the compound (MA1) include 1-butylamine, isobutylamine, 2-ethylhexylamine, 1-hexylheptylamine, 1-dodecylamine, 1-tetradecylamine, 3,3-diphenylpropylamine and 1-hexylamine. , cyclopentylamine, cyclohexylamine, 4-methylbenzylamine, 4-(tert-butyl)benzylamine, ethyl 4-aminobutyrate, 1-octylamine, diisobutylamine, piperidine, 1-methylpiperazine, 1-phenylpiperazine, thio morpholine, aniline, N-ethylaniline, methylsulfonamide, phenylsulfonamide, trifluoromethylsulfonamide, tert-butylsulfonamide, benzylsulfonamide, 4-fluorophenylsulfonamide and the like.

The amount of compound (MA1) to be used is generally 0.4 mol or more and 20 mol or less, preferably 0.5 mol or more and 15 mol or less, more preferably 0.6 mol, per 1 mol of compound (pt3). It is more than 10 mol or less.

A catalyst may be used in the reaction between compound (pt3) and compound (MA1). Examples of the catalyst used in the reaction of the compound (pt3) and the compound (MA1) include the same examples as the catalyst used in the production of the compound (pt3), and preferred catalyst embodiments are also the same.

The amount of the catalyst used in the reaction between the compound (pt3) and the compound (MA1) may be a catalytic amount, for example, 0.1 mol or more and 50 mol or less per 100 mol of the compound (pt3), preferably It is 0.5 mol or more and 40 mol or less, more preferably 1.0 mol or more and 30 mol or less.

When a metal catalyst is used in the reaction of compound (pt3) and compound (MA1), a specific ligand may be coordinated to the metal catalyst. Examples of ligands include the same examples of ligands used in the preparation of compound (pt3).

The amount of the ligand used in the reaction between the compound (pt3) and the compound (MA1) is, for example, 0.05 mol or more and 100 mol or less, preferably 0.1 mol or more and 80 mol or more per 1 mol of the metal catalyst. mol or less, more preferably 0.5 mol or more and 50 mol or less, and still more preferably 0.8 mol or more and 30 mol or less.

As the solvent for the reaction of the compound (pt3) and the compound (MA1), water, nitrile solvents and ether solvents are preferable, and water, acetonitrile, ethylene glycol dimethyl ether and diethylene glycol dimethyl ether are more preferable. Further, as the solvent in the reaction of the compound (pt3) and the compound (MA1), a solvent (especially an organic solvent) that has been sufficiently deoxidized and/or dehydrated can be used in order to suppress side reactions. Preferred are dehydrated acetonitrile and dehydrated ethylene glycol dimethyl ether, and more preferred is dehydrated acetonitrile.

The amount of the solvent used in the reaction of compound (pt3) and compound (MA1) is generally 0.1 to 1000 parts by mass per 1 part by mass of compound (pt3).

In the reaction between the compound (pt3) and the compound (MA1), a base may coexist in order to efficiently proceed the reaction. The base may be an organic base or an inorganic base. Bases are preferred, trimethylamine, triethylamine, tri-n-propylamine, tri-n-butylamine, diisopropylethylamine, tri-n-octylamine, tri-n-decylamine, triphenylamine, N,N-dimethylaniline, N, Tertiary amines such as N,N',N'-tetramethylethylenediamine, N-methylpyrrolidine and 4-dimethylaminopyridine are more preferred.

When a base is used in the reaction of compound (pt3) and compound (MA1), the amount of the base to be used is generally 0.1 mol or more and 50 mol or less, preferably 1 mol of compound (pt3). It is 0.5 mol or more and 30 mol or less.

The reaction temperature for reacting the compound (pt3) and the compound (MA1) is usually -100°C or higher and 300°C or lower. The reaction time for reacting the compound (pt3) and the compound (MA1) is usually 0.5 hours to 300 hours.

After the completion of each of the above reactions, the method for taking out the target compound is not particularly limited, and it can be taken out by various known methods. After taking out, the resulting residue may be purified by column chromatography, recrystallization, or the like. The chemical structure of the obtained compound can be analyzed by a known analytical technique and its conditions. Examples of such analysis techniques include, but are not limited to, X-ray crystallography, mass spectrometry (LC), NMR analysis, and elemental analysis. X-ray crystal structure analysis is described, for example, in Chemistry of Materials, 2012, Vol. 24, p. 4647-4652.

Compound (IA) can be produced by using the following compound (MA1-1) as compound (MA1) in the production process of compound (I) above.

［式中、Ｒ²及びＲ¹¹は、上述の定義と同一である。］

[In the formula, R ² and R ¹¹ are the same as defined above. ]

The content of compound (I) may be 100% by mass with respect to the total amount of colorant (A), and the lower limit may be, for example, 0.1% by mass or more, or 5% by mass or more. is preferable, 10% by mass or more is more preferable, 20% by mass or more is still more preferable, 30% by mass or more is still more preferable, and 50% by mass or more is still more preferable.

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

As the dye (A1-1), known dyes can be used as long as they do not contain the compound (I), and examples thereof include solvent dyes, acid dyes, direct dyes, mordant dyes and the like. Dyes include, for example, compounds classified as dyes in the Color Index (published by The Society of Dyers and Colorists) and known dyes described in Dye Note (Shikisensha). Also, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinolines Dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes and the like. Among these, organic solvent-soluble dyes are preferred.

Specific examples include dyes with the following Color Index (C.I.) numbers.
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 dyes,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 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, 104, 105, 106, 109; 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; I. disperse dyes,
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. Basic Green 1; I. basic dye,
C. I. Reactive Yellow 2, 76, 116;
C. I. Reactive Orange 16;
C. I. C.I. Reactive Red 36; I. reactive dyes,
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. Modant 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. Modant 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. such as C.I. I. modant dye,
C. I. Bat Green 1; I. Vat dye, etc.

As the pigment (A1-2), a known pigment can be used as long as it does not contain the compound (I). mentioned.

Pigments classified as pigments include C.I. 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. black pigments such as Pigment Black 1, 7, 31, 32;

When the coloring agent (A) contains the coloring agent (A1), the content of the coloring agent (A1) in the coloring agent (A) is, for example, 0.1% by mass with respect to the total amount of the coloring agent (A). It is 99.9% by mass or more, preferably 1% by mass or more and 50% by mass or less.

When the colored resin composition contains the solvent (E), a coloring composition containing the coloring agent (A) and the solvent (E) (hereinafter sometimes referred to as a coloring agent-containing liquid) is prepared in advance, and then the coloring composition is prepared. may be used to prepare the colored resin composition. When the colorant (A) does not dissolve in the solvent (E), for example, when the colorant (A) contains the pigment (A1-2), the coloring composition contains the colorant (A) and the solvent (E). It can be prepared by dispersing and mixing. The colored composition may contain part or all of the solvent (E) contained in the colored 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 0.99% by mass or less, relative to 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, still more preferably 1% by mass or more and 90% by mass or less, and particularly preferably 1% by mass 80 mass % or less, more preferably 1 mass % or more and 70 mass % or less, particularly preferably 1 mass % or more and 60 mass % or less, and most preferably 1 mass % or more and 50 mass % or less.

The content of the coloring agent (A) in the coloring composition is 100% by mass or less, preferably 0.001% by mass or more and 99.999% by mass or less, relative to the total amount of solids in the coloring composition. , more preferably 0.01% by mass or more and 99% by mass or less, still more preferably 0.1% by mass or more and 95% by mass or less, and even more preferably 0.5% by mass or more and 90% by mass or less. , Particularly preferably, it is 1.0% by mass or more and 80% by mass or less.

The coloring agent (A) may optionally be subjected to rosin treatment, surface treatment using a derivative having an acidic or basic group introduced therein, grafting treatment to the surface of the coloring agent (A) with a polymer compound or the like, sulfuric acid It may be subjected to atomization treatment by an atomization method, salt milling method or the like, washing treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method or the like, and the like. It is preferable that the particle size of the colorant (A) is substantially uniform.

The coloring agent (A) can be uniformly dispersed in the solution by adding a dispersing agent and performing a dispersion treatment. When two or more types are used in combination as the colorant (A), each of them may be subjected to dispersion treatment alone, or a plurality of types may be mixed and subjected to dispersion treatment.

Examples of dispersing agents include surfactants, and cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples include surfactants such as polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. As the dispersant, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), and EFKA (registered trademark). (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.) and Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and the like. .

When a dispersant is used, the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10000 parts by mass or less, preferably 5 parts by mass, per 100 parts by mass of the colorant (A) in the coloring composition. It is from 10 parts by mass to 3000 parts by mass, and more preferably from 15 parts by mass to 1000 parts by mass. When the amount of the dispersant used is within the above range, there is a tendency to obtain a colored composition in a more uniformly dispersed state.

After preparing a coloring composition containing a coloring agent (A) and a solvent (E) in advance, when preparing a coloring resin composition using the coloring composition, the coloring composition is contained in the coloring resin composition A part or all, preferably a part, of the resin (B) to be used may be included in advance. By containing the resin (B) in advance, the dispersion stability of the coloring composition can be further improved.

When the coloring composition contains the resin (B), the content of the resin (B) is, for example, 0.01 parts by mass or more and 10000 parts by mass with respect to 100 parts by mass of the coloring agent (A) in the coloring composition. 0.01 to 8,000 parts by mass is preferable, 0.01 to 5,000 parts by mass is more preferable, and 0.1 to 3,000 parts by mass is even more preferable.

The content of the coloring agent (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 or less, based on the total solid content of the colored resin composition. more preferably 1.0% by mass or more and 30% by mass or less, and even more preferably 1.5% by mass or more and 20% by mass or less. When the content of the coloring agent (A) is within the above range, the color density of the color filter is sufficient, and the necessary amount of the resin (B) can be contained in the composition. It is preferable 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 content of the solvent from the total amount of the colored resin composition. The total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography.

The content ratio (resin (B)/colorant (A)) of the colorant (A) and the resin (B) described later in the colored resin composition is, for example, preferably 2.0 or more on a mass basis. It is more preferably 3.0 or more, still more preferably 4.0 or more, and preferably 12 or less, more preferably 10 or less, still more preferably 8.0 or less.

<Resin (B)>
The resin (B) is not particularly limited as long as it is used for forming a photoresist, unlike a thermoplastic resin, but is an alkali-soluble resin, preferably an alkali-soluble resin having a carboxylic acid.

Examples of the resin (B) include the following resins [K1] to [K6].
Resin [K1]; at least one monomer (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter referred to as "(a)" or "monomer (a)" a monomer (b) (hereinafter referred to as “(b)” or “monomer (b )” may be referred to)) and a copolymer having a structural unit derived from;
Resin [K2]; a structural unit derived from (a), a structural unit derived from (b), and a monomer (c) copolymerizable with (a) (where (a) and (b) are different) (hereinafter sometimes referred to as "(c)" or "monomer (c)") and a structural unit derived from;
Resin [K3]; a copolymer having a structural unit derived from (a) and a structural unit derived from (c);
Resin [K4]; a copolymer having a structural unit obtained by adding (b) to a structural unit derived from (a) and a structural unit derived from (c);
Resin [K5]; a copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and a structural unit derived from (c);
Resin [K6]: A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic anhydride, and a structural unit derived from (c).

Examples of 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-vinyl phthalic acid, 4-vinyl phthalic 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-6-methylbicyclo[2.2.1]hept-2-ene and 5-carboxy-6-ethylbicyclo [2.2.1] Bicyclounsaturated compounds containing a carboxy group such as hept-2-ene;
Carboxylic acid anhydrides such as the anhydrides of the above unsaturated dicarboxylic acids except fumaric acid and mesaconic acid;
Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate kind;
unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid;
Among these, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferable from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in an alkaline aqueous solution.
In this specification, "(meth)acrylic acid" represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

The monomer (b) has a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. A polymerizable compound having 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 "(b1)" or "monomer (b1)"), an oxetanyl group and a monomer having an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)" or "monomer (b2)"), a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)" or "monomer (b3)") and the like.

As the monomer (b1), for example, a monomer having a structure obtained by epoxidizing an unsaturated aliphatic hydrocarbon (hereinafter referred to as "(b1-1)" or "monomer (b1-1)" ), and a monomer having a structure obtained by epoxidizing an unsaturated alicyclic hydrocarbon (hereinafter sometimes referred to as "(b1-2)" or "monomer (b1-2)"). .

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferred. Specific examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3 -bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4 -tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene , 2,4,6-tris(glycidyloxymethyl)styrene and the like.

Examples of the monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (eg, Celloxide (registered trademark) 2000; manufactured by Daicel Corporation), and 3,4-epoxycyclohexylmethyl. (Meth)acrylate (eg, Cychromer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (eg, Cychromer (registered trademark) M100; manufactured by Daicel Corporation) , a compound represented by the formula (BI), a compound represented by the formula (BII), and the like.

[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 substituted 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 alkyl groups 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.

Alkyl groups in which a hydrogen atom is substituted with hydroxy include, for example, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1 -hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like.

R ^a and R ^b preferably include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, 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, A hexane-1,6-diyl group and the like can be mentioned.

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

Examples of the compound represented by formula (BI) include compounds represented by any one 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 preferable.

Examples of the compound represented by formula (BII) include compounds represented by any one of formulas (BII-1) to (BII-15), and among them, preferably formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and compounds represented by 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 the formula (BI) and the compound represented by the formula (BII) may be used alone, or the compound represented by the formula (BI) and the compound represented by the formula (BII) may be used in combination. You may When these are used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10: on a molar basis. 90 to 90:10, 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, 3-methyl-3-(meth)acryloyl 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 preferred. 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.

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2. 1.0 ^2,6 ]decane-8-yl (meth)acrylate (in the technical field, it is commonly referred to as “dicyclopentanyl (meth)acrylate”. Also, “tricyclodecyl (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 (commonly referred to as “dicyclopentenyl (meth)acrylate” in the technical field), tricyclo[5.2.1.0 ^2,6 ]decen-9-yl (meth)acrylate, di 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 acrylates;
Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate 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 oxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclounsaturated compounds;
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 and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; vinyl chloride and vinylidene chloride, etc. 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; .
Among these, styrene, vinyl toluene, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (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, 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 and benzyl(meth)acrylate are preferred.

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

The resin [K1] is, for example, the method described in the document "Experimental Method for Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin, 1st edition, 1st edition, published on March 1, 1972) and the literature It can be manufactured with reference to the cited document described in .

Specifically, predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and, for example, by replacing oxygen with nitrogen, a deoxygenated atmosphere is created, and while stirring, A method of heating and keeping warm can be mentioned. The polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2′-azobisisobutyronitrile, 2,2′-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.). As the solvent, any solvent can be used as long as it dissolves each monomer, and examples thereof include the solvents described later as the solvent (E) for the colored resin composition of the present invention.

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

In the resin [K2], the ratio of the structural units derived from each of the total structural units constituting the resin [K2] is
Structural unit derived from (a); 2 to 45 mol%
Structural unit derived from (b); 2 to 95 mol%
Structural unit derived from (c); 1 to 65 mol%
is preferably
Structural unit derived from (a); 5 to 40 mol%
Structural unit derived from (b); 5 to 80 mol%
Structural unit derived from (c); 5 to 60 mol%
is more preferable.
When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored resin composition, developability when forming a colored pattern, and the solvent resistance and heat resistance of the resulting optical filter are improved. And tend to be excellent in mechanical strength.

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

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

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

Next, part of the carboxylic acid and/or carboxylic anhydride derived from (a) in the copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms of (b).
Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced from nitrogen to air, and (b) a reaction catalyst (e.g., tris ( dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (e.g., hydroquinone, etc.) are placed in a flask and reacted at, for example, 60 to 130° C. for 1 to 10 hours to produce resin [K4]. can.
The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By setting this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the solvent resistance, heat resistance, mechanical strength and sensitivity balance of the resulting pattern tend to be good. be. Since the cyclic ether has high reactivity and unreacted (b) hardly remains, (b1) is preferable as the (b) used in the resin [K4], and (b1-1) is more preferable.
The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor to be used is preferably 0.001 to 5 parts by weight per 100 parts by weight of the total amount of (a), (b) and (c).
Reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by polymerization, and the like. As with the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, and the like.

For resin [K5], in the first step, a copolymer of (b) and (c) is obtained in the same manner as in the method for producing resin [K1] described above. In the same manner as described above, the obtained copolymer may be used as a solution after the reaction as it is, or may be used as a concentrated or diluted solution. You may use what was taken out as.
The ratio of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer is, respectively,
Structural unit derived from (b); 5 to 95 mol%
Structural unit derived from (c); 5 to 95 mol%
is preferably
Structural unit derived from (b); 10 to 90 mol%
Structural unit derived from (c); 10 to 90 mol%
is more preferable.

Furthermore, under the same conditions as in the method for producing resin [K4], the cyclic ether derived from (b) in the copolymer of (b) and (c) is added to the carboxylic acid or carboxylic anhydride of (a). Resin [K5] can be obtained by reacting substances.
The amount of (a) to be reacted with the copolymer is preferably 5 to 80 mol per 100 mol of (b). Since the cyclic ether has high reactivity and unreacted (b) does not easily remain, (b1) is preferable as (b) used in resin [K5], and (b1-1) is more preferable.

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

Specific resins (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] Resin [K1] such as decyl 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 acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[ 5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyl Resins such as oxetane/(meth)acrylic acid/styrene copolymer [K2]; resins such as benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer [K3] ; Resin obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymer Resins such as acrylate-added resins and resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer [K4]; tricyclodecyl (Meth)acrylate/glycidyl (meth)acrylate copolymer reacted with (meth)acrylic acid, tricyclodecyl (meth)acrylate/styrene/glycidyl (meth)acrylate copolymer (meth)acrylic Resin [K5] such as acid-reacted resin; tricyclodecyl (meth) acrylate/glycidyl (meth) acrylate copolymer reacted with (meth)acrylic acid and further reacted with tetrahydrophthalic anhydride resin [K6] such as a resin obtained by

Resin (B) is more preferably resin [K1] or resin [K2], and particularly preferably resin [K1].

The polystyrene equivalent weight average molecular weight (Mw) of the resin (B) 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. 30,000 or less. When the weight-average molecular weight is within the above range, the unexposed area tends to have high solubility in a developer, 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 1.001 or more and 5 or less, and still more preferably 1.00. 01 or more and 4 or less.

The acid value (solid content conversion 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, still more preferably 30 mg-KOH/g or more and 150 mg-KOH/g or less, particularly preferably 60 mg-KOH/g or more and 135 mg-KOH/g g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin, and can be determined by titration with an aqueous potassium hydroxide solution, for example.

The content of the resin (B) is preferably 5 to 90% by mass, more preferably 5 to 50% by mass, and still more preferably 10 to 40% by mass in 100% by mass of the solid content of the colored resin composition. and more preferably 15 to 35% by mass. When the content of the resin (B) is within the above range, the solubility of the unexposed area in the developer tends to be high.

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by an active radical and/or an acid generated from the polymerization initiator (D). 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., as well as monomers (a), (b) and (c) described above.

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

Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol 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 4,000 or less, more preferably 70 or more and 3,500 or less, still more preferably 100 or more and 3,000 or less, and still more preferably is 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 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 or less, relative to the total solid content of the colored resin composition. , more preferably 10% by mass or more and 80% by mass or less, and still more preferably 20% 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 capable of initiating polymerization by generating active radicals, acids, etc. by the action of light or heat, and known polymerization initiators can be used.

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

Alkylphenone compounds include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1- and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one and the like. Commercially available products such as Irgacure (registered trademark) 369, 907, 379 (manufactured by BASF) may be used as the alkylphenone compound.
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, Also included are 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone and benzyl dimethyl ketal.

Biimidazole compounds include, for example, 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetraphenylbiimidazole, 2,2′-bis(2,3-dichlorophenyl)-4 ,4′,5,5′-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 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, JP-B-48-38403, JP-A-62-174204, etc.) and 4 , 4′,5,5′-positioned phenyl groups are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).

Triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine and 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, etc. .

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

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

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

The content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass with respect to 100 parts by mass of the total amount of the total resin (B) and the polymerizable compound (C) contained in the colored resin composition. part or less, more preferably 1 part by mass or more and 20 parts by mass or less. When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, thereby improving the productivity of the color filter.

<Polymerization initiation aid (D1)>
The polymerization initiation aid (D1) is a compound or a sensitizer used to accelerate 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, 4- 2-ethylhexyl dimethylaminobenzoate, N,N-dimethylp-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis( ethylmethylamino)benzophenone and the like, preferably 4,4'-bis(diethylamino)benzophenone. As the amine compound, a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) may be used.

Alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxy and anthracene and 2-ethyl-9,10-dibutoxyanthracene.

Thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone and 1-chloro-4-propoxythioxanthone.

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 is preferably 0 with respect to 100 parts by mass of the total amount of all resins (B) and polymerizable compounds (C) contained in the colored resin composition. .1 to 30 parts by mass, more preferably 1 to 20 parts by mass.

<Solvent (E)>
The solvent (E) is not particularly limited, and solvents commonly used in the field can be used.
The solvent (E) is, for example, an ester solvent (a solvent containing -COO- in the molecule but not containing -O-), an ether solvent (a solvent containing -O- in the molecule but not containing -COO-), Ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule but not containing -COO-), alcohol solvents (containing OH in the molecule , —O—, —CO— and —COO—-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like. These solvents may be used in combination of two or more.

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, and propylene glycol monoethyl ether. , propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, methylanisole and the like.

Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, 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 Ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate and the like.

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

Alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerin.

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

Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

Preferred solvents (E) are propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and cyclohexanone.

When the solvent (E) is included, the content of the solvent (E) is usually 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, relative to the total amount of the colored resin composition, It is more preferably 50% by mass or more and 95% by mass or less, still more preferably 70% by mass or more and 95% by mass or less, and even more preferably 75% by mass or more and 90% by mass or less. In other words, the total solid content of the colored resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 50% by mass or less. , more preferably 5% by mass or more and 30% by mass or less, and even more preferably 10% by mass or more and 25% by mass or less. When the content of the solvent (E) is within the above range, the flatness at the time of coating is improved, and when a color filter is formed, the color density is not insufficient, so the display characteristics tend to be improved. .

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

Examples of silicone-based surfactants include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, Toray SH7PA, Toray DC11PA, Toray SH21PA, Toray SH28PA, Toray SH29PA, Toray SH30PA, Toray SH8400 (trade name: 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), etc. .

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

Examples of fluorine atom-containing silicone-based surfactants include surfactants having siloxane bonds and fluorocarbon chains in the molecule. Specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, F477 and F443 (manufactured by DIC Corporation) and the like can be mentioned.

When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.0005% by mass or more and 1% by mass or less, relative to the total amount of the colored resin composition. 001% by mass or more and 0.5% by mass or less, more preferably 0.005% by mass or more and 0.1% by mass or less. 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.

<Other ingredients>
The colored resin composition, if necessary, contains additives known in the art such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, etc. It's okay.

<Method for producing colored resin composition>
The colored resin composition contains a coloring agent (A), a resin (B), a polymerizable compound (C) that is used as necessary, a polymerization initiator (D), a solvent (E), a leveling agent (F) and other It can be prepared by mixing the ingredients. Mixing can be performed by a known or commonly used device and conditions.
The colorant (A) may be mixed with part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size is about 0.2 μm or less. It is preferable to use it in a state in which it is folded. At this time, if necessary, a part or all of the dispersant and resin (B) may be blended. Further, the coloring agent (A) may be dissolved in the solvent (E) in part or in its entirety before use. The desired colored resin composition can be prepared by mixing the colorant-containing liquid thus obtained with the remaining components so as to have a predetermined concentration.

<Manufacturing method of color filter>
A color filter, which may be a color conversion layer, can be formed from the colored resin composition. A photolithography method, an inkjet method, a printing method, and the like can be used as a method for forming a colored pattern. Among them, the photolithographic method is preferred. The photolithographic method is a method in which the colored resin composition is applied to a substrate, dried to form a colored resin composition layer, exposed through a photomask, and developed. In the photolithographic method, a colored coating film, which is a cured product of the colored resin composition layer, can be formed by not using a photomask during exposure and/or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.

The film thickness of the color filter to be produced is not particularly limited, and can be appropriately adjusted according to the purpose and application. More preferably, it is 0.5 μm or more and 6 μm or less.

Examples of the substrate 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; A thin film of aluminum, silver, silver/copper/palladium alloy, etc., is formed on the substrate. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates.

The formation of each color pixel by the photolithographic method can be carried out using a known or commonly used apparatus and conditions. For example, it can be produced as follows.
First, a colored resin composition is applied onto a substrate, dried by heating (pre-baking) and/or dried under reduced pressure to remove volatile components such as solvents, and dried to obtain a smooth colored resin composition layer.
Examples of coating methods include a spin coating method, a slit coating method, a slit and spin coating method, and the like.
The temperature for heat drying is preferably 30° C. or higher and 120° C. or lower, more preferably 50° C. or higher and 110° C. or lower. The heating time is preferably 10 seconds or more and 60 minutes or less, more preferably 30 seconds or more and 30 minutes or less.
When drying under reduced pressure, it is preferable to carry out under a pressure of 50 Pa or more and 150 Pa or less in a temperature range of 20° C. or more and 25° C. or less.
The thickness of the colored resin composition layer is not particularly limited, and may be appropriately selected according to the desired thickness of the color filter.

Next, the colored resin composition layer is exposed through a photomask to form a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern suitable for the intended use is used. In addition, since it is possible to uniformly irradiate the entire exposure surface with parallel light rays and to accurately align the photomask and the substrate on which the colored resin composition layer is formed, the exposure apparatus such as a mask aligner and a stepper can be used. is preferably used.

A light source used for exposure is preferably a light source that emits light having a wavelength of 250 nm or more and 450 nm or less. For example, light of less than 350 nm is cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm is selectively extracted using a bandpass filter that extracts these wavelength ranges. You can Specifically, mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, and the like can be used.

A colored pattern is formed on the substrate by contacting the exposed colored resin composition layer with a developer for development. By development, the unexposed portion of the colored resin composition layer is dissolved in the developer and removed. As the developer, for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate, tetramethylammonium hydroxide and the like are 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 a puddle method, a dipping method, a spray method, and the like. Further, the substrate may be tilted at any 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-baking temperature is preferably 150° C. or higher and 250° C. or lower, more preferably 160° C. or higher and 240° C. or lower. The post-baking time is preferably 1 minute or more and 120 minutes or less, more preferably 10 minutes or more and 60 minutes or less.

<Display device>
The color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices, especially as a color filter used in organic EL devices.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited by the following examples, and can be modified appropriately within the scope that can conform to the gist of the above and later descriptions. It is of course possible to implement them, and all of them are included in the technical scope of the present invention. In the following description, "parts" means "parts by mass" and "%" means "% by mass" unless otherwise specified.

In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC; Model 1200 manufactured by Agilent, MASS; Model LC/MSD6130 manufactured by Agilent).

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

(Synthesis example 1)
42 parts of acenaphthenequinone (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 15 parts of malononitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and 672 parts of dehydrated acetonitrile (manufactured by Kanto Chemical Co., Ltd.) were mixed and heated at 82° C. for 6 hours. Stirred. The resulting mixture was cooled to 0° C. resulting in an orange-red precipitate. The mixture containing this orange-red precipitate was filtered, and the filtered residue was washed with 200 parts of acetonitrile and 400 parts of water. The resulting residue was dried under reduced pressure at 60° C. to obtain 48 parts of the compound represented by the formula (pt2-1) (hereinafter sometimes referred to as compound (pt2-1)) (yield 90%).

<Identification of compound (pt2-1)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 231
Exact Mass: 230

(Synthesis example 2)
25 parts of the compound (pt2-1) obtained in Synthesis Example 1, 1.5 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), 312 parts of acetonitrile (manufactured by Kanto Chemical Co., Ltd.), and 2 parts of water were mixed. , 80° C., and stirred for 5 hours. Cooling to 0° C. produced a brown precipitate. The mixture containing this brown precipitate was filtered, and the filtered residue was washed with 400 parts of water and 50 parts of acetonitrile. The resulting residue was dried under reduced pressure at 60 ° C., purified by silica gel column (solvent: chloroform / ethyl acetate = 10/1, vol / vol), yellowish brown compound represented by formula (pt3-1) (hereinafter sometimes referred to as compound (pt3-1)) was obtained in 17 parts (yield 68%).

<Identification of compound (pt3-1)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 231
Exact Mass: 230

(Synthesis Example 3)
3.0 parts of the compound (pt3-1) obtained in Synthesis Example 2, 1-butylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.0 parts, and 21 parts of dehydrated acetonitrile (manufactured by Kanto Chemical Co., Ltd.) were mixed. and stirred at 25° C. for 4 hours. The reaction solution was concentrated, and the resulting residue was dried under reduced pressure at 60° C. and purified with a neutral alumina column (solvent: chloroform to acetonitrile gradient), resulting in a brown formula (I-4) with metallic luster. 1.3 parts of the represented compound (hereinafter sometimes referred to as compound (I-4)) was obtained (yield 33%).

<Identification of compound (I-4)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 302
Exact Mass: 301

(Synthesis Example 4)
A compound represented by formula (I-40) (hereinafter , sometimes referred to as compound (I-40)) was obtained (yield 41%).

<Identification of compound (I-40)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 302
Exact Mass: 301

(Synthesis Example 5)
A compound represented by formula (I-48) in the same manner as in Synthesis Example 3, except that 1.0 parts of 1-butylamine was replaced with 1.9 parts of 2-ethylhexylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) (hereinafter sometimes referred to as compound (I-48)) was obtained (yield 37%).

<Identification of compound (I-48)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 358
Exact Mass: 357

(Synthesis Example 6)
Represented by formula (I-34) in the same manner as in Synthesis Example 3, except that 1.0 parts of 1-butylamine was replaced with 2.9 parts of 1-hexylheptylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) 0.40 parts of a compound (hereinafter sometimes referred to as compound (I-34)) was obtained (yield 7%).

<Identification of compound (I-34)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 428
Exact Mass: 427

(Synthesis Example 7)
A compound represented by formula (I-12) in the same manner as in Synthesis Example 3, except that 1.0 parts of 1-butylamine was replaced with 2.7 parts of 1-dodecylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) (hereinafter sometimes referred to as compound (I-12)) was obtained (19% yield).

<Identification of compound (I-12)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 414
Exact Mass: 413

(Synthesis Example 8)
Represented by formula (I-14) in the same manner as in Synthesis Example 3, except that 1.0 parts of 1-butylamine was replaced with 3.1 parts of 1-tetradecylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.5 parts of a compound (hereinafter sometimes referred to as compound (I-14)) was obtained (yield 26%).

<Identification of compound (I-14)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 442
Exact Mass: 441

(Synthesis Example 9)
Except for replacing 1.0 parts of 1-butylamine with 3.0 parts of 3,3-diphenylpropylamine (manufactured by Tokyo Kasei Kogyo Co., Ltd.), in the same manner as in Synthesis Example 3, represented by formula (I-112) 0.55 parts of a compound (hereinafter sometimes referred to as compound (I-112)) was obtained (yield 10%).

<Identification of compound (I-112)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 440
Exact Mass: 439

(Synthesis Example 10)
A compound represented by formula (I-6) in the same manner as in Synthesis Example 3, except that 1.0 parts of 1-butylamine was replaced with 1.0 parts of 1-hexylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) (hereinafter sometimes referred to as compound (I-6)) was obtained (yield 2%).

<Identification of compound (I-6)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 330
Exact Mass: 329

(Synthesis Example 11)
A compound represented by formula (I-114) (hereinafter , sometimes referred to as compound (I-114)) was obtained (yield 32%).

<Identification of compound (I-114)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 314
Exact Mass: 313

(Synthesis Example 12)
A compound represented by formula (I-118) (hereinafter , sometimes referred to as compound (I-118)) was obtained (yield 26%).

<Identification of compound (I-118)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 328
Exact Mass: 327

(Synthesis Example 13)
A compound represented by formula (I-104) (hereinafter referred to as 1.3 parts of compound (I-104) was obtained (yield 29%).

<Identification of compound (I-104)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 350
Exact Mass: 349

(Synthesis Example 14)
Represented by formula (I-109) in the same manner as in Synthesis Example 3, except that 1.0 parts of 1-butylamine was replaced with 2.3 parts of 4-(tert-butyl)benzylamine (manufactured by Aldrich) 0.45 parts of a compound (hereinafter sometimes referred to as compound (I-109)) was obtained (yield 9%).

<Identification of compound (I-109)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 392
Exact Mass: 391

(Synthesis Example 15)
Represented by formula (I-80) in the same manner as in Synthesis Example 3, except that 1.0 parts of 1-butylamine was replaced with 1.9 parts of ethyl 4-aminobutyrate (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.1 parts of a compound (hereinafter sometimes referred to as compound (I-80)) was obtained (yield 24%).

<Identification of compound (I-80)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 360
Exact Mass: 359

(Synthesis Example 16)
A compound represented by formula (I-8) in the same manner as in Synthesis Example 3, except that 1.0 parts of 1-butylamine was replaced with 1.8 parts of 1-octylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) (hereinafter sometimes referred to as compound (I-8)) was obtained in 3.3 parts (yield 71%).

<Identification of compound (I-8)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 358
Exact Mass: 357

(Synthesis Example 17)
A compound represented by formula (I-529) (hereinafter , sometimes referred to as compound (I-529)) was obtained (yield 1.7%).

<Identification of compound (I-529)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 358
Exact Mass: 357

(Synthesis Example 18)
A compound represented by formula (I-713) (hereinafter referred to as 0.75 parts of compound (I-713) was obtained (yield 18%).

<Identification of compound (I-713)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 314
Exact Mass: 313

(Synthesis Example 19)
A compound represented by formula (I-721) in the same manner as in Synthesis Example 3, except that 1.0 parts of 1-butylamine was replaced with 1.4 parts of 1-methylpiperazine (manufactured by Tokyo Chemical Industry Co., Ltd.) (hereinafter sometimes referred to as compound (I-721)) was obtained (yield: 15%).

<Identification of compound (I-721)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 329
Exact Mass: 328

(Synthesis Example 20)
A compound represented by formula (I-724) in the same manner as in Synthesis Example 3, except that 1.0 parts of 1-butylamine was replaced with 2.5 parts of 1-phenylpiperazine (manufactured by Tokyo Chemical Industry Co., Ltd.) (hereinafter sometimes referred to as compound (I-724)) was obtained (yield 12%).

<Identification of compound (I-724)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 391
Exact Mass: 390

(Synthesis Example 21)
A compound represented by formula (I-718) (hereinafter , sometimes referred to as compound (I-718)) was obtained (yield 23%).

<Identification of compound (I-718)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 332
Exact Mass: 331

(Synthesis Example 22)
20 parts of acenaphthenequinone (manufactured by Tokyo Chemical Industry Co., Ltd.) and 78 parts of bromine (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.) were mixed and stirred under reflux for 2 hours. The resulting mixture was cooled to 20° C. and 300 parts of a 2M aqueous sodium sulfite solution was added to produce a brownish yellow precipitate. The mixture containing this brown-yellow precipitate was filtered, and the filtered residue was washed with 500 parts of water. The resulting residue was dried under reduced pressure at 60° C. to obtain 26 parts of the compound represented by the formula (pt1-2) (hereinafter sometimes referred to as compound (pt1-2)) (yield 90%).

<Identification of compound (pt1-2)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 261
Exact Mass: 260

(Synthesis Example 23)
The compound represented by formula (pt2-2) (hereinafter referred to as compound (pt2-2)) was obtained (yield 58%).

<Identification of compound (pt2-2)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 309
Exact Mass: 308

(Synthesis Example 24)
A compound represented by formula (pt3-2) ( 17 parts of compound (pt3-2) was obtained (yield: 50%).

<Identification of compound (pt3-2)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 309
Exact Mass: 308

(Synthesis Example 25)
18 parts of the compound (pt3-2) obtained in Synthesis Example 24, aniline (manufactured by Tokyo Chemical Industry Co., Ltd.) 12 parts, palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) 0.65 parts, 2-dicyclohexylphosphino -2',6'-Dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.0 parts, tert-butoxysodium (manufactured by Tokyo Chemical Industry Co., Ltd.) 28 parts, and dehydrated ethylene glycol dimethyl ether (Kanto Chemical Co., Ltd.) ) were mixed and stirred at 70°C for 6 hours. After the reaction mixture was filtered through celite, the filtrate was concentrated, and the resulting residue was dried under reduced pressure at 60° C. and purified by a neutral alumina column (solvent: chloroform to acetonitrile gradient) to give a brown color with metallic luster. 11 parts of the compound represented by the formula (I-95) (hereinafter sometimes referred to as compound (I-95)) was obtained (yield 59%).

<Identification of compound (I-95)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 322
Exact Mass: 321

(Synthesis Example 26)
A compound represented by formula (I-421) (hereinafter referred to as compound (I -421)) was obtained (yield 70%).

<Identification of compound (I-421)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 350
Exact Mass: 349

(Example 1)
10 parts of the compound (pt3-1) obtained in Synthesis Example 2, 4.5 parts of methanesulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.), N,N,N',N'-tetramethylethylenediamine (Tokyo Chemical Industry Co., Ltd. Co., Ltd.) and 21 parts of dehydrated acetonitrile (Kanto Kagaku Co., Ltd.) were mixed and stirred at 35° C. for 18 hours. The reaction solution was concentrated, the resulting residue was dried under reduced pressure at 60 ° C., and purified with a neutral alumina column (solvent: chloroform to acetonitrile gradient), resulting in a blue-purple formula (I-126). 3.0 parts of a compound (hereinafter sometimes referred to as compound (I-126)) was obtained (yield 21%).

<Identification of compound (I-126)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 324
Exact Mass: 323

(Example 2)
Compound represented by formula (I-144) in the same manner as in Example 1 except that 4.5 parts of methanesulfonamide was replaced with 7.5 parts of phenylsulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.) ( 3.1 parts of compound (I-144) was obtained (yield: 19%).

<Identification of compound (I-144)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 386
Exact Mass: 385

(Example 3)
Formula (I-656) in the same manner as in Example 1 except that 4.5 parts of methanesulfonamide was replaced with 7.1 parts of trifluoromethylsulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.4 parts of a compound (hereinafter sometimes referred to as compound (I-656)) was obtained (yield 9%).

<Identification of compound (I-656)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 378
Exact Mass: 377

(Example 4)
Represented by formula (I-653) in the same manner as in Example 1, except that 4.5 parts of methanesulfonamide was replaced with 7.1 parts of tert-butylsulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.) 2.2 parts of a compound (hereinafter sometimes referred to as compound (I-653)) were obtained (yield 14%).

<Identification of compound (I-653)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 366
Exact Mass: 365

(Example 5)
Compound represented by formula (I-150) in the same manner as in Example 1 except that 4.5 parts of methanesulfonamide was replaced with 8.2 parts of benzylsulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.) ( 2.4 parts of compound (I-150) was obtained (yield: 14%).

<Identification of compound (I-150)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 400
Exact Mass: 399

(Example 6)
Represented by formula (I-659) in the same manner as in Example 1, except that 4.5 parts of methanesulfonamide was replaced with 8.4 parts of 4-fluorophenylsulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.) 0.90 parts of a compound (hereinafter sometimes referred to as compound (I-659)) was obtained (yield 5%).

<Identification of compound (I-659)>
(mass spectrometry) ionization mode = ESI+: m/z = [M+H] ⁺ 404
Exact Mass: 403

(Synthesis Example 27)
A compound represented by the following formula (x) (hereinafter sometimes referred to as compound (x)) was synthesized according to the description in Synthesis Example 2 of JP-A-2020-079397.

(Synthesis Example 28)
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. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^{2, 6} ] A mixed solution of 289 parts of a mixture of decane-9-yl acrylate (content ratio is 1:1 in molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition was completed, it was held at 80° C. for 4 hours, then cooled to room temperature, and a copolymer (resin B1) solution with a solid content of 35.1% and a viscosity of 125 mPa·s measured with a Brookfield viscometer (23° C.) was obtained. got The resulting copolymer had a weight average molecular weight Mw of 9.2×10 ³ , a dispersity of 2.08, and an acid value of 77 mg-KOH/g in terms of solid content. Resin B1 has the following structural units.

<Example 7>
(1) Preparation of Coloring Composition The following components were mixed to obtain a coloring composition 1.
(A) Colorant: Compound (I-4) 2.6 parts (B) Resin: Resin B1 solution 54 parts (E) Solvent: Propylene glycol monomethyl ether acetate 420 parts (2) Preparation of colored resin composition Then, the following A colored resin composition 1 was obtained by mixing the components.
Coloring composition 1 478 parts (C) polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) polymerization initiator: N-benzoyloxy-1- (4-Phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 2 parts (F) Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400: Toray Dow Corning Corporation) 0.15 parts

(3) Preparation of colored coating film (color filter) On a 5 cm square glass substrate (Eagle XG; manufactured by Corning), the colored resin composition is spin-coated so that the film thickness after post-baking is 2 μm. After coating, it was pre-baked at 100° C. for 3 minutes to form a colored resin composition layer. After allowing to cool, the colored resin composition layer formed on the substrate was exposed using an exposure machine (TME-150RSK; manufactured by Topcon Corporation) in an air atmosphere at an exposure amount of 80 mJ/cm ² (365 nm standard). irradiated with light. After light irradiation, post-baking was performed in an oven at 230° C. for 30 minutes to obtain a colored coating film.
The thickness of the colored coating film was measured using DEKTAK3 (manufactured by Nippon Vacuum Engineering Co., Ltd.). Table 11 shows the results.

(4) Contrast evaluation Contrast meter (CT-1: manufactured by Tsubosaka Electric Co., Ltd., color difference meter BM-5A: manufactured by Topcon Corporation, light source: F-10, polarizing film: Tsubosaka Denki Co., Ltd.) was used to measure the contrast. The blank value at the time of measurement is 30,000. If the contrast of the colored coating film is good, it can be said that the colored pattern produced from the same colored resin composition also has a good contrast. Table 11 shows the results.

<Examples 8 to 22, Comparative Example 1>
A colored composition and a colored resin composition were prepared in the same manner as in Example 7 except that the compound (I-4) of Example 7 was replaced with a compound shown in Table 11, and the contrast was evaluated. gone. Table 11 shows the results.

Compound (I-4) of Example 7, compound (I-529), compound (I-713), compound (I-721), compound (I-724), compound (I-718), compound (I -95), compound (I-421), compound (I-656), compound (I-653), compound (I-150), or compound (I-659) in the same manner as in Example 7. A colored coating film is produced by adjusting the coloring composition and the colored resin composition, and a contrast evaluation is performed to show a good contrast.

Claims (6)

A colored resin composition containing a coloring agent and a resin, wherein the coloring agent contains a compound represented by formula (I).

[in the formula (I),
R ¹ and R ² independently represent a hydrogen atom, -R ^8a or -SO ₂ -R ^8b .
R ¹ and R ² may form an optionally substituted ring together with the nitrogen atom to which they are attached, and —CH ₂ — constituting the ring is —O -, -CO-, -S-, -S(O) ₂ -, -NH-, or -NR ^8g -.
R ³ to R ⁷ each independently represent a hydrogen atom, --R ^8c , --OR ^8d , --CO- ^{OR 8e} , --O--CO--R ^8f , a halogen atom, a hydroxy group, a carboxyl group, a sulfo group, or a nitro group.
R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
When a plurality of R ^8a , R ^8b , R ^8c , R ^8d , R ^8e , R ^8f and R ^8g are present, they may be the same or different. ] 2. The colored resin composition according to claim 1, wherein R ¹ in formula (I) is --SO ₂ --R ^8b and R ² is a hydrogen atom or --R ^8a . The colored resin composition according to claim 1 or 2, further comprising a polymerizable compound and a polymerization initiator. A color filter formed from the colored resin composition according to any one of claims 1 to 3. A display device comprising the color filter according to claim 4 . A compound represented by formula (IA).

[In the formula (IA),
R ¹¹ represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
R ² represents a hydrogen atom, -R ^8a or -SO ₂ -R ^8b .
R ³ to R ⁷ each independently represent a hydrogen atom, --R ^8c , --OR ^8d , --CO- ^{OR 8e} , --O--CO--R ^8f , a halogen atom, a hydroxy group, a carboxyl group, a sulfo group, or a nitro group.
R ^8a , R ^8b , R ^8c , R ^8d , R ^8e and R ^8f each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
When multiple R ^8c , R ^8d , R ^8e and R ^8f are present, they may be the same or different. ]