JP2013116945A - Dye and coloring photosensitive composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a dye excellent in solubility and heat resistance and a novel compound suitable for the dye, particularly a yellow dye having a maximum absorption wavelength in the range of 400 to 470 nm, a coloring (alkali developability) photosensitive composition using the dye, and an optical filter using the coloring (alkali developability) photosensitive composition and a color filter suitable for an image display such as a liquid crystal display panel without decreasing luminance.SOLUTION: A compound used as the dye is represented by formula (1) (wherein A is a benzene ring, a naphthalene ring or an anthracene ring; these rings may be substituted with halogen, cyano, hydroxyl, nitro or the like; Ris hydrogen, phenyl, nitro, 1-8C alkyl or the like; X is nitrogen, -NR-, oxygen, sulfur, phosphorus, -PR- or the like; R is hydrogen, 1-8C alkyl, 6-20C aryl or 7-20C arylalkyl; alkyl, aryl and arylalkyl may be substituted with halogen, hydroxyl or nitro, and the methylene group in the alkyl group and the arylalkyl group may be interrupted with -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-; and X and A may link to form a ring structure).

Description

  The present invention relates to a dye designed to have a desired hue and improved heat resistance, and a novel compound suitable for the dye. Furthermore, the present invention relates to a colored photosensitive composition that can be polymerized by energy rays using the dye, and a color filter that uses the colored photosensitive composition.

  Compounds having high intensity absorption for specific light include recording layers of optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display devices (LCD), plasma display panels (PDP). ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.

In an optical filter for an image display device such as a liquid crystal display device (LCD), a plasma display panel (PDP), an electroluminescence display (ELD), a cathode ray tube display device (CRT), a fluorescent display tube, a field emission display, etc., 300 Various compounds that absorb light having a wavelength of ˜1100 nm are used as light absorbing materials.
Further, in recent years, a light absorber that selectively absorbs a wavelength of 380 to 500 nm has been demanded in order to ensure sufficient color purity and color separation of the display element and to improve image quality. These light absorbers are required to have particularly steep light absorption, that is, having a small half-value width of λmax and not to lose its function due to light, heat, or the like.

An optical filter mainly used for a liquid crystal display (LCD) includes a color filter. In general, three primary colors of RGB have been used for a color filter, but it is difficult to have a pure RGB hue with a single color material, and a pure RGB hue using a plurality of color materials. Efforts have been made to get closer to. Therefore, color materials such as yellow, orange and purple are required instead of RGB.
Organic and / or inorganic pigments have been used as light absorbers for color filters due to their high heat resistance. However, since they are pigments, there is a problem in that the luminance of a display device is lowered. This problem has been solved by increasing the brightness of the. However, with the trend toward lower power consumption, development of dyes having excellent solubility in solvents and resin compositions and high heat resistance, and development of color filters using the dyes have become active. Patent Documents 1 to 3 disclose dyes using a compound having a specific structure.
However, the dyes (compounds) described in these documents are not satisfactory in terms of solubility and heat resistance.

Japanese Patent No. 2819562 Japanese Patent No. 2844708 Japanese Patent No. 4490042

  Accordingly, an object of the present invention is to provide a dye having excellent solubility and heat resistance and a novel compound suitable for the dye, and in particular, a yellow dye having a maximum absorption wavelength in the region of 400 to 470 nm. Is to provide. Another object of the present invention is to provide a colored (alkali developable) photosensitive composition using the above dye. Another object of the present invention is to provide an optical filter using the above colored (alkali developable) photosensitive composition, particularly a color filter suitable for an image display device such as a liquid crystal display panel without reducing luminance. There is.

  As a result of intensive studies, the present inventor has found that a compound having a specific structure has a maximum absorption wavelength in a region of 400 to 470 nm and that a dye using the compound has excellent solubility and heat resistance. In addition, a colored (alkali developable) photosensitive composition using the above dye does not decrease the luminance of an optical filter (particularly a color filter) and is suitable for a color filter for an image display device such as a liquid crystal display panel. The present invention has been found.

  This invention is made | formed based on the said knowledge, and provides the dye (henceforth a dye (A)) containing at least 1 type of compound represented by following General formula (1).

（式中、Ａは、ベンゼン環、ナフタレン環又はアントラセン環を表し、これらの環は、ハロゲン原子、シアノ基、水酸基、ニトロ基、炭素原子数１〜８のアルキル基、炭素原子数１〜８のアルコキシ基、炭素原子数１〜８のハロゲン化アルキル基又は炭素原子数１〜８のハロゲン化アルコキシ基で置換されていてもよく、
Ｒ¹は、水素原子、フェニル基、ニトロ基、炭素原子数１〜８のアルキル基、炭素原子数１〜８のアルコキシ基、炭素原子数１〜８のハロゲン化アルキル基又は炭素原子数１〜８のハロゲン化アルコキシ基を表し、
Ｘは、窒素原子、−ＮＲ−、酸素原子、硫黄原子、リン原子、−ＰＲ−又は下記一般式（２）で表される有機基を表し、
Ｒは、水素原子、炭素原子数１〜８のアルキル基、炭素原子数６〜２０のアリール基又は炭素原子数７〜２０のアリールアルキル基を表し、該アルキル基、アリール基及びアリールアルキル基は、ハロゲン原子、水酸基又はニトロ基で置換されていてもよく、該アルキル基及びアリールアルキル基中のメチレン基は、−ＣＯＯ−、−Ｏ−、−ＯＣＯ−、−ＮＨＣＯ−、−ＮＨ−又は−ＣＯＮＨ−で中断されていてもよく、ＸとＡは連結して環構造を形成してもよい。）

(In the formula, A represents a benzene ring, a naphthalene ring or an anthracene ring, and these rings are a halogen atom, a cyano group, a hydroxyl group, a nitro group, an alkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. An alkoxy group, a halogenated alkyl group having 1 to 8 carbon atoms, or a halogenated alkoxy group having 1 to 8 carbon atoms,
R ¹ represents a hydrogen atom, a phenyl group, a nitro group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or 1 to 1 carbon atom. 8 represents a halogenated alkoxy group,
X represents a nitrogen atom, -NR-, an oxygen atom, a sulfur atom, a phosphorus atom, -PR- or an organic group represented by the following general formula (2),
R represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group and arylalkyl group are , A halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be —COO—, —O—, —OCO—, —NHCO—, —NH— or — It may be interrupted by CONH-, and X and A may be linked to form a ring structure. )

（式中、Ｘ¹は、−ＣＲ²⁰Ｒ²¹−、−ＮＲ²⁰−、二価の炭素原子数１〜３５の鎖状炭化水素基、二価の炭素原子数３〜３５の脂環式炭化水素基、二価の炭素原子数６〜３５の芳香族炭化水素基、二価の炭素原子数２〜３５の複素環基、更にこれらの基を複数組み合わせた基又は下記（ｘ）、（ｙ）若しくは（ｚ）で表される置換基を表し、上記鎖状炭化水素基、脂環式炭化水素基、芳香族炭化水素基及び複素環基は、−ＣＯＯ−、−Ｏ−、−ＯＣＯ−、−ＮＨＣＯ−、−ＮＨ−、−ＣＯＮＨ−、−Ｏ−ＣＯＮＨ−又は−ＮＨＣＯ−Ｏ−の何れかで中断されていてもよく、
Ｒ²⁰及びＲ²¹は、それぞれ独立に、水素原子、炭素原子数１〜８のアルキル基、炭素原子数６〜２０のアリール基又は炭素原子数７〜２０のアリールアルキル基を表し、
Ｚ¹及びＺ²は、それぞれ独立に、直接結合、−Ｏ−、−Ｓ−、−ＳＯ₂−、−ＳＯ−、−ＮＲ¹⁰−又は−ＰＲ¹⁰−を表し、
Ｒ¹⁰は、水素原子、炭素原子数１〜８のアルキル基、炭素原子数６〜２０のアリール基又は炭素原子数７〜２０のアリールアルキル基を表し、該アルキル基、アリール基及びアリールアルキル基は、ハロゲン原子、水酸基又はニトロ基で置換されていてもよく、該アルキル基及びアリールアルキル基中のメチレン基は、−ＣＯＯ−、−Ｏ−、−ＯＣＯ−、−ＮＨＣＯ−、−ＮＨ−又は−ＣＯＮＨ−で中断されていてもよい。
但し、上記一般式（２）で表される有機基の炭素原子数は、１〜３５の範囲内である。）

(In the formula, X ¹ is —CR ²⁰ R ²¹ —, —NR ²⁰ —, a divalent chain hydrocarbon group having 1 to 35 carbon atoms, and an alicyclic carbon atom having 3 to 35 carbon atoms. A hydrogen group, a divalent aromatic hydrocarbon group having 6 to 35 carbon atoms, a divalent heterocyclic group having 2 to 35 carbon atoms, a group obtained by combining a plurality of these groups, or the following (x), (y ) Or (z), and the chain hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group are -COO-, -O-, -OCO- , -NHCO-, -NH-, -CONH-, -O-CONH- or -NHCO-O-
R ²⁰ and R ²¹ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms,
Z ¹ and Z ² each independently represent a direct bond, —O—, —S—, —SO ₂ —, —SO—, —NR ¹⁰ — or —PR ¹⁰ —,
R ¹⁰ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group, and arylalkyl group May be substituted with a halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be —COO—, —O—, —OCO—, —NHCO—, —NH— or It may be interrupted by -CONH-.
However, the number of carbon atoms of the organic group represented by the general formula (2) is in the range of 1 to 35. )

（式中、Ｚ¹²は水素原子、炭素原子数１〜１０のアルキル基若しくは炭素原子数１〜１０のアルコキシ基により置換されてもよいフェニル基、又は炭素原子数１〜１０のアルキル基若しくは炭素原子数１〜１０のアルコキシ基により置換されてもよい炭素原子数３〜１０のシクロアルキル基を表し、
Ｙ¹は炭素原子数１〜１０のアルキル基、炭素原子数１〜１０のアルコキシ基、炭素原子数２〜１０のアルケニル基又はハロゲン原子を表し、上記アルキル基、アルコキシ基及びアルケニル基はハロゲン原子で置換されていてもよく、
ｄは０〜４の整数である。）

(In the formula, Z ¹² represents a hydrogen atom, a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, or an alkyl group or carbon having 1 to 10 carbon atoms. Represents a cycloalkyl group having 3 to 10 carbon atoms which may be substituted by an alkoxy group having 1 to 10 atoms,
Y ¹ represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom, and the alkyl group, alkoxy group, and alkenyl group are each a halogen atom. May be replaced with
d is an integer of 0-4. )

（式中、Ｙ²及びＺ¹³は、それぞれ独立して、ハロゲン原子で置換されてもよい炭素原子数１〜１０のアルキル基、ハロゲン原子で置換されてもよい炭素原子数６〜２０のアリール基、ハロゲン原子で置換されてもよい炭素原子数６〜２０のアリールオキシ基、ハロゲン原子で置換されてもよい炭素原子数６〜２０のアリールチオ基、ハロゲン原子で置換されてもよい炭素原子数８〜２０のアリールアルケニル基、ハロゲン原子で置換されてもよい炭素原子数７〜２０のアリールアルキル基、ハロゲン原子で置換されてもよい炭素原子数２〜２０の複素環基、更にこれらの基を複数組み合わせた基又はハロゲン原子を表し、該アルキル基及びアリールアルキル基中のメチレン基は不飽和結合、−Ｏ−又は−Ｓ−で中断されていてもよく、Ｚ¹³は、隣接するＺ¹³同士で環を形成していてもよく、
ｅは０〜４の整数を表し、ｆは０〜８の整数を表し、ｇは０〜４の整数を表し、ｈは０〜４の整数を表し、ｇとｈの合計は２〜４の整数である。）

Wherein Y ² and Z ¹³ are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or an aryl having 6 to 20 carbon atoms which may be substituted with a halogen atom. Group, an aryloxy group having 6 to 20 carbon atoms that may be substituted with a halogen atom, an arylthio group having 6 to 20 carbon atoms that may be substituted with a halogen atom, and the number of carbon atoms that may be substituted with a halogen atom An arylalkenyl group having 8 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms which may be substituted with a halogen atom, a heterocyclic group having 2 to 20 carbon atoms which may be substituted with a halogen atom, and these groups; a represents a combination of plural groups or a halogen atom, a methylene group in the alkyl group and the arylalkyl group may be interrupted by an unsaturated bond, -O- or -S-, Z ¹³ , They may form a ring with the adjacent Z ¹³ each other,
e represents an integer of 0 to 4, f represents an integer of 0 to 8, g represents an integer of 0 to 4, h represents an integer of 0 to 4, and the sum of g and h is 2 to 4. It is an integer. )

  The present invention also provides the dye (A), a polymerizable compound (B) having an ethylenically unsaturated bond, a photopolymerization initiator (C), and, if necessary, an inorganic pigment and / or an organic pigment (D). The present invention provides a colored photosensitive composition to be contained.

  The present invention also provides a colored alkali-developable photosensitive composition containing the dye (A), an alkali-developable polymerizable compound (B ′) having an ethylenically unsaturated bond, and a photopolymerization initiator (C). It provides things.

  In addition, the present invention provides a cured product of the colored photosensitive composition or colored alkali-developable photosensitive composition, a color filter for display device comprising at least a part of the cured product, and the color filter for display device A liquid crystal display panel using the above is provided.

  The present invention also provides a novel compound represented by the following general formula (1 ').

（式中、Ａ’は、ベンゼン環、ナフタレン環又はアントラセン環を表し、これらの環は、ハロゲン原子、シアノ基、水酸基、ニトロ基、炭素原子数１〜８のアルキル基、炭素原子数１〜８のアルコキシ基、炭素原子数１〜８のハロゲン化アルキル基又は炭素原子数１〜８のハロゲン化アルコキシ基で置換されていてもよく、
Ｒ^1'は、水素原子、フェニル基、シアノ基、炭素原子数１〜８のアルキル基、炭素原子数１〜８のアルコキシ基、炭素原子数１〜８のハロゲン化アルキル基又は炭素原子数１〜８のハロゲン化アルコキシ基を表し、
Ｘ’は、窒素原子、−ＮＲ’−、酸素原子、硫黄原子、リン原子、−ＰＲ’−又は下記一般式（２’）で表される有機基を表し、
Ｒ’は、水素原子、炭素原子数１〜８のアルキル基、炭素原子数６〜２０のアリール基又は炭素原子数７〜２０のアリールアルキル基を表し、該アルキル基、アリール基及びアリールアルキル基は、ハロゲン原子、水酸基又はニトロ基で置換されていてもよく、該アルキル基及びアリールアルキル基中のメチレン基は、−ＣＯＯ−、−Ｏ−、−ＯＣＯ−、−ＮＨＣＯ−、−ＮＨ−又は−ＣＯＮＨ−の何れかで中断されていてもよく、Ｘ’とＡ’は連結して環構造を形成してもよく、
更に以下の（ｉ）〜（ｉｉｉ）の何れかの条件を満足する。
（ｉ）Ｘ’で表される有機基中に芳香環を有する。
（ｉｉ）Ｘ’で表される有機基中に水酸基を少なくとも２つ以上有する。
（ｉｉｉ）Ｘ’で表される有機基中にアクリル基、メタクリル基、スチリル基又はエポキシ基を少なくとも１つ以上有する。）

(In the formula, A ′ represents a benzene ring, a naphthalene ring or an anthracene ring, and these rings include a halogen atom, a cyano group, a hydroxyl group, a nitro group, an alkyl group having 1 to 8 carbon atoms, and an alkyl group having 1 to 1 carbon atoms. May be substituted with an alkoxy group having 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or a halogenated alkoxy group having 1 to 8 carbon atoms,
R ^{1 ′} is a hydrogen atom, a phenyl group, a cyano group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or 1 carbon atom. Represents a halogenated alkoxy group of ~ 8,
X ′ represents a nitrogen atom, —NR′—, an oxygen atom, a sulfur atom, a phosphorus atom, —PR′— or an organic group represented by the following general formula (2 ′),
R ′ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group, and arylalkyl group May be substituted with a halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be —COO—, —O—, —OCO—, —NHCO—, —NH— or -CONH- may be interrupted, and X 'and A' may be linked to form a ring structure,
Furthermore, any one of the following conditions (i) to (iii) is satisfied.
(I) It has an aromatic ring in the organic group represented by X ′.
(Ii) The organic group represented by X ′ has at least two hydroxyl groups.
(Iii) The organic group represented by X ′ has at least one acrylic group, methacryl group, styryl group or epoxy group. )

（式中、Ｘ^1'は、−ＣＲ^20'Ｒ^21'−、−ＮＲ^20'−、二価の炭素原子数１〜３５の鎖状炭化水素基、二価の炭素原子数３〜３５の脂環式炭化水素基、二価の炭素原子数６〜３５の芳香族炭化水素基、二価の炭素原子数２〜３５の複素環基、更にこれらの基を複数組み合わせた基又は下記（ｘ’）、（ｙ’）又は（ｚ’）で表される置換基を表し、該鎖状炭化水素基は、−ＣＯＯ−、−Ｏ−、−ＯＣＯ−、−ＮＨＣＯ−、−ＮＨ−、−ＣＯＮＨ−、−Ｏ−ＣＯＮＨ−又は−ＮＨＣＯ−Ｏ−の何れかで中断されていてもよく、
Ｒ^20'及びＲ^21'は、それぞれ独立に、水素原子、炭素原子数１〜８のアルキル基、炭素原子数６〜２０のアリール基又は炭素原子数７〜２０のアリールアルキル基を表し、
Ｚ^1'及びＺ^2'は、それぞれ独立に、直接結合、−Ｏ−、−Ｓ−、−ＳＯ₂−、−ＳＯ−、−ＮＲ^10'−又は−ＰＲ^10'−を表し、
Ｒ^10'は、水素原子、炭素原子数１〜８のアルキル基、炭素原子数６〜２０のアリール基又は炭素原子数７〜２０のアリールアルキル基を表し、該アルキル基、アリール基及びアリールアルキル基は、ハロゲン原子、水酸基又はニトロ基で置換されていてもよく、該アルキル基及びアリールアルキル基中のメチレン基は、−ＣＯＯ−、−Ｏ−、−ＯＣＯ−、−ＮＨＣＯ−、−ＮＨ−又は−ＣＯＮＨ−で中断されていてもよい。
但し、上記一般式（２’）で表される有機基の炭素原子数は、１〜３５の範囲内である。）

(In the formula, X ^{1 ′} is —CR ^{20 ′} R ^{21 ′} —, —NR ^{20 ′} —, a divalent chain hydrocarbon group having 1 to 35 carbon atoms, and a divalent carbon atom having 3 to 35 carbon atoms. An alicyclic hydrocarbon group, a divalent aromatic hydrocarbon group having 6 to 35 carbon atoms, a divalent heterocyclic group having 2 to 35 carbon atoms, a group obtained by combining a plurality of these groups, or the following (x '), A substituent represented by (y') or (z '), and the chain hydrocarbon group is -COO-, -O-, -OCO-, -NHCO-, -NH-,- May be interrupted with either CONH-, -O-CONH- or -NHCO-O-
R ^{20 ′} and R ^{21 ′} each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms,
Z ^{1 ′} and Z ^{2 ′} each independently represent a direct bond, —O—, —S—, —SO ₂ —, —SO—, —NR ^{10 ′} — or —PR ^{10 ′} —
R ^{10 ′} represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group, and arylalkyl The group may be substituted with a halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be -COO-, -O-, -OCO-, -NHCO-, -NH-. Or it may be interrupted by -CONH-.
However, the number of carbon atoms of the organic group represented by the general formula (2 ′) is in the range of 1 to 35. )

（式中、Ｚ^12'は水素原子、炭素原子数１〜１０のアルキル基若しくは炭素原子数１〜１０のアルコキシ基により置換されてもよいフェニル基、又は炭素原子数１〜１０のアルキル基若しくは炭素原子数１〜１０のアルコキシ基により置換されてもよい炭素原子数３〜１０のシクロアルキル基を表し、
Ｙ^1'は炭素原子数１〜１０のアルキル基、炭素原子数１〜１０のアルコキシ基、炭素原子数２〜１０のアルケニル基又はハロゲン原子を表し、上記アルキル基、アルコキシ基及びアルケニル基はハロゲン原子で置換されていてもよく、
ｄ’は０〜４の整数である。）

(Wherein Z ^{12 ′} is a hydrogen atom, a phenyl group which may be substituted with an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms, or Represents a cycloalkyl group having 3 to 10 carbon atoms which may be substituted by an alkoxy group having 1 to 10 carbon atoms,
Y ^{1 ′} represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom, and the alkyl group, alkoxy group, and alkenyl group are each a halogen atom. May be substituted with atoms,
d 'is an integer of 0-4. )

（式中、Ｙ^2'及びＺ^13'は、それぞれ独立して、ハロゲン原子で置換されてもよい炭素原子数１〜１０のアルキル基、ハロゲン原子で置換されてもよい炭素原子数６〜２０のアリール基、ハロゲン原子で置換されてもよい炭素原子数６〜２０のアリールオキシ基、ハロゲン原子で置換されてもよい炭素原子数６〜２０のアリールチオ基、ハロゲン原子で置換されてもよい炭素原子数８〜２０のアリールアルケニル基、ハロゲン原子で置換されてもよい炭素原子数７〜２０のアリールアルキル基、ハロゲン原子で置換されてもよい炭素原子数２〜２０の複素環基、更にこれらの基を複数組み合わせた基又はハロゲン原子を表し、該アルキル基及びアリールアルキル基中のメチレン基は不飽和結合、−Ｏ−又は−Ｓ−で中断されていてもよく、Ｚ^13'は、隣接するＺ^13'同士で環を形成していてもよく、
ｅ’は０〜４の整数を表し、ｆ’は０〜８の整数を表し、ｇ’は０〜４の整数を表し、ｈ’は０〜４の整数を表し、ｇ’とｈ’の合計は２〜４の整数である。）

Wherein Y ^{2 ′} and Z ^{13 ′} are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or 6 to 20 carbon atoms which may be substituted with a halogen atom. An aryloxy group having 6 to 20 carbon atoms which may be substituted with a halogen atom, an arylthio group having 6 to 20 carbon atoms which may be substituted with a halogen atom, or a carbon which may be substituted with a halogen atom An arylalkenyl group having 8 to 20 atoms, an arylalkyl group having 7 to 20 carbon atoms which may be substituted with a halogen atom, a heterocyclic group having 2 to 20 carbon atoms which may be substituted with a halogen atom, and these And a methylene group in the alkyl group and arylalkyl group may be interrupted by an unsaturated bond, —O— or —S—, and Z ^{13 '} May form a ring with adjacent Z ^13' ,
e ′ represents an integer of 0 to 4, f ′ represents an integer of 0 to 8, g ′ represents an integer of 0 to 4, h ′ represents an integer of 0 to 4, and g ′ and h ′ The sum is an integer of 2-4. )

  ADVANTAGE OF THE INVENTION According to this invention, the novel compound suitable for the dye excellent in solubility and heat resistance and this dye can be provided. The colored photosensitive composition (colored alkali-developable photosensitive composition) using the dye and the cured product thereof are suitable for color filters for display devices and liquid crystal display panels.

  Hereinafter, the present invention will be described in detail based on preferred embodiments.

First, the dye (A) of the present invention will be described. The compound used for the dye (A) of the present invention is represented by the general formula (1).
Examples of the halogen atom that may substitute the benzene ring, naphthalene ring or anthracene ring represented by A in the general formula (1) include fluorine, chlorine, bromine and iodine.
In the general formula (1), the benzene ring, naphthalene ring or anthracene ring represented by A may be substituted, and the alkyl group having 1 to 8 carbon atoms and the alkyl having 1 to 8 carbon atoms represented by R ^1. The groups include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl, tert-amyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, Groups such as 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-octyl and the like;
Examples of the alkoxy group having 1 to 8 carbon atoms include methyloxy, ethyloxy, iso-propyloxy, butyloxy, sec-butyloxy, tert-butyloxy, iso-butyloxy, amyloxy, iso-amyloxy, tert-amyloxy, hexyloxy, 2 -Hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, iso-heptyloxy, tert-heptyloxy, 1-octyloxy, iso-octyloxy , Tert-octyloxy and the like,
As the halogenated alkyl group having 1 to 8 carbon atoms and the halogenated alkoxy group having 1 to 8 carbon atoms, one or more of the hydrogen atoms of the alkyl group and alkoxy group are substituted with the halogen atom. Group.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R in the general formula (1) include the groups exemplified in the description of R ¹ in the general formula (1).
Examples of the aryl group having 6 to 20 carbon atoms include phenyl, naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-iso-propylphenyl, 4-iso-propylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5- Di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di tert- pentylphenyl, 2,5-di -tert- amyl phenyl, include groups such as 2,4,5-trimethylphenyl,
Examples of the arylalkyl group having 7 to 20 carbon atoms include benzyl, phenethyl, 2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl and the like.

  As the ring structure formed by linking X and A in the general formula (1), a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a benzene ring, a pyrrolidine ring, a pyrrole ring, a piperazine ring, a piperidine ring, a morpholine ring, Examples thereof include 5- to 7-membered rings such as thiomorpholine ring, tetrahydropyridine ring, lactone ring and lactam ring, and condensed rings such as naphthalene ring and anthracene ring.

Examples of the divalent chain hydrocarbon group having 1 to 35 carbon atoms represented by X ¹ in the general formula (2) include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, 1- Methylmethane-1,1-diyl, 1-ethylmethane-1,1-diyl, 1-propylmethane-1,1-diyl, 1-methylethane-1,2-diyl, 1-ethylethane-1,2-diyl, 1-propylethane-1,2-diyl, 1-methylpropane-1,3-diyl, 1-ethylpropane-1,3-diyl, 1-propylpropane-1,3-diyl, 2-methylpropane-1 , 3-diyl, 2-ethylpropane-1,3-diyl, 2-propylpropane-1,3-diyl, 1-methylbutane-1,4-diyl, 1-ethylbutane-1,4- 1-propylbutane-1,4-diyl, 2-methylbutane-1,4-diyl, 2-ethylbutane-1,4-diyl, 2-propylbutane-1,4-diyl, 1-methylpentane-1 , 5-diyl, 1-ethylpentane-1,5-diyl, 1-propylpentane-1,5-diyl, 2-methylpentane-1,5-diyl, 2-ethylpentane-1,5-diyl, 2, -Propylpentane-1,5-diyl, 3-methylpentane-1,5-diyl, 3-ethylpentane-1,5-diyl, 3-propylpentane-1,5-diyl, 1-methylhexane-1 , 6-diyl, 1-ethylhexane-1,6-diyl, 2-methylhexane-1,6-diyl, 2-ethylhexane-1,6-diyl, 3-methylhexane-1,6 -Diyl, 3-ethyl Hexane-1,6-diyl, 1-methylheptane-1,7-diyl, 2-methylheptane-1,7-diyl, 3-methylheptane-1,7-diyl, 4-methylheptane-1,7 Alkanediyl groups such as -diyl, 1-phenylmethane-1,1-diyl, 1-phenylethane-1,2-diyl, 1-phenylpropane-1,3-diyl;
Examples of the divalent alicyclic hydrocarbon group having 3 to 35 carbon atoms include cyclopropylidene, cyclobutylidene, cyclopentylidene, cyclohexylidene, cycloheptylidene, 2,4-dimethylcyclobutylidene, 4 -Groups such as methylcyclohexylidene,
Examples of the divalent aromatic hydrocarbon group having 6 to 35 carbon atoms include groups such as phenylene, naphthylene, and biphenyl.
Examples of the divalent heterocyclic group having 2 to 35 carbon atoms include pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzoimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, Thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinon-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazolidine- A divalent group in which a heterocyclic group such as 3-yl or 2,4-dioxyoxazolidin-3-yl is substituted with Z ^{1 or} Z ² ;
The chain hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group are a halogen atom, a cyano group, a nitro group, or an alkyl group having 1 to 8 carbon atoms represented by R ^1. , Or an optionally substituted alkoxy group having 1 to 8 carbon atoms, —COO—, —O—, —OCO—, —NHCO—, —NH—, —CONH—, —O—CONH—, or — It may be interrupted by NHCO-O-, and may be bonded to an alkylene group having 1 to 4 carbon atoms, a nitrogen atom, -NR-, an oxygen atom, a sulfur atom, a phosphorus atom, -PR- or the like.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R ¹⁰ , R ²¹ and R ²² which are groups in X ¹ in the general formula (2) include those in the description of R ¹ in the general formula (1). Examples thereof include the groups exemplified, and examples of the aryl group having 6 to 20 carbon atoms and the arylalkyl group having 7 to 20 carbon atoms include the groups exemplified in the description of R in the general formula (1).

The alkyl group having 1 to 10 carbon atoms and the alkoxy group having 1 to 10 carbon atoms which may be substituted for the phenyl group represented by Z ¹² in the formula (x) or the cycloalkyl group having 3 to 10 carbon atoms. the, it includes the groups exemplified in the description of R ¹ in the general formula (1).

The cycloalkyl group having 3 to 10 carbon atoms represented by Z ¹² in the formula (x), cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2,4-dimethyl-cyclobutyl, 4- Examples include groups such as methylcyclohexyl.
Examples of the alkyl group having 1 to 10 carbon atoms, the alkoxy group having 1 to 10 carbon atoms and the halogen atom represented by Y ¹ in the above formula (x) are the explanation of A or R ¹ in the above general formula (1). Group exemplified in the above,
Examples of the alkenyl group having 2 to 10 carbon atoms include vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-octenyl group, 1 -Groups such as a decenyl group.

Examples of the alkyl group having 1 to 10 carbon atoms which may be substituted with the halogen atom represented by Y ² and Z ¹³ in the above formula (z) are exemplified in the description of R ¹ in the above general formula (1). Groups,
Examples of the aryl group having 6 to 20 carbon atoms which may be substituted with a halogen atom include an aryl group exemplified in the description of R in the general formula (1) and one or more hydrogen atoms of the aryl group. A group substituted with a halogen atom,
Examples of the arylalkyl group having 7 to 20 carbon atoms which may be substituted with a halogen atom include the arylalkyl group exemplified in the description of R in the general formula (1) and one of the hydrogen atoms of the arylalkyl group, A group in which a plurality is substituted with a halogen atom,
Examples of the heterocyclic group having 2 to 20 carbon atoms which may be substituted with a halogen atom include those having 2 to 20 carbon atoms among the heterocyclic groups exemplified in the description of X ¹ in the general formula (2). Range, and groups in which one or more of the hydrogen atoms of the heterocyclic group are substituted with halogen atoms,
Examples of the ring structure formed by adjacent Z ¹³ include those exemplified as the ring structure formed by linking X and A in the general formula (1).

Examples of the aryloxy group having 6 to 20 carbon atoms which may be substituted with the halogen atom represented by Y ² and Z ¹³ in the above formula (z) include phenoxy, 2-methylphenoxy, 3-methylphenoxy. 4-methylphenoxy, 2,3-dimethylphenoxy, 2,4-dimethylphenoxy, 2,5-dimethylphenoxy, 2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3,5-dimethylphenoxy, 2, 3,4-trimethylphenoxy, 2,3,5-trimethylphenoxy, 2,3,6-trimethylphenoxy, 2,4,5-trimethylphenoxy, 2,4,6-trimethylphenoxy, 3,4,5-trimethyl Phenoxy, 2,3,4,5-tetramethylphenoxy, 2,3,4,6-tetramethylphenoxy, 2,3 5,6-tetramethylphenoxy, pentamethylphenoxy, ethylphenoxy, n-propylphenoxy, isopropylphenoxy, n-butylphenoxy, sec-butylphenoxy, tert-butylphenoxy, n-hexylphenoxy, n-octylphenoxy, n- Decylphenoxy, n-tetradecylphenoxy, 1-naphthoxy, 2-naphthoxy, 1-anthryloxy, 1-phenanthryloxy, o-tolyloxy, m-tolyloxy, p-tolyloxy, 9-fluorenyloxy, 1 -Tetrahydronaphthoxy, 2-tetrahydronaphthoxy, 1-acenaphthenyloxy, 1-indanyloxy, 2-indanyloxy and the like,
Examples of the arylthio group having 6 to 20 carbon atoms which may be substituted with a halogen atom include phenylthio, 2-methylphenylthio, 3-methylphenylthio, 4-methylphenylthio, and 2,3-dimethylphenylthio. 2,4-dimethylphenylthio, 2,5-dimethylphenylthio, 2,6-dimethylphenylthio, 3,4-dimethylphenylthio, 3,5-dimethylphenylthio, 2,3,4-trimethylphenylthio 2,3,5-trimethylphenylthio, 2,3,6-trimethylphenylthio, 2,4,5-trimethylphenylthio, 2,4,6-trimethylphenylthio, 3,4,5-trimethylphenylthio 2,3,4,5-tetramethylphenylthio, 2,3,4,6-tetramethylphenylthio, 2,3,5,6 Tetramethylphenylthio, pentamethylphenylthio, ethylphenylthio, n-propylphenylthio, isopropylphenylthio, n-butylphenylthio, sec-butylphenylthio, tert-butylphenylthio, n-hexylphenylthio, n- Octylphenylthio, n-decylphenylthio, n-tetradecylphenylthio, 1-naphthylthio, 2-naphthylthio, 1-anthrylthio, 1-phenanthrylthio, o-tolylthio, m-tolylthio, p-tolylthio, 9-fluorenylthio 1-tetrahydronaphthylthio, 2-tetrahydronaphthylthio, 1-acenaphthenylthio, 1-indanylthio, 2-indanylthio and the like,
Examples of the arylalkenyl group having 8 to 20 carbon atoms include styryl and 4-fluorostyryl.

Among the compounds represented by the general formula (1), those in which R ¹ is a hydrogen atom; those in which A is a benzene ring are preferred because the raw materials are easily obtained and manufactured.
Furthermore, it is more preferable that X is a group selected from the following <Group 1> because the raw materials are particularly easily available.
Further, those in which X in the general formula (1) is an asymmetric group or those having 7 or more carbon atoms are particularly preferable because of excellent solubility.
Among the compounds represented by the general formula (1), those having a hydroxyl group or an aromatic ring are preferable because of excellent solubility.
Among the compounds represented by the general formula (1), X in the general formula (1) is an organic group represented by the general formula (2), and X ¹ in the general formula (2). Is a divalent carbon atom interrupted by any of -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH- or -NHCO-O- Those having a chain hydrocarbon group of 1 to 35 are preferable because of their good solubility in organic solvents.

（上記式中、Ｒ¹⁰は、上記一般式（２）におけるＲ¹⁰と同じ基であり、Ｒ¹⁰が基中に二つ以上ある場合、同じであっても異なっていてもよく、Ｒ^10'は、Ｒ¹⁰の１つ以上の水素原子が水酸基で置換されている基であり、Ｚ¹⁰及びＺ¹¹は、下記群Ａから選ばれる２価の基を表し、ｐは１〜３の整数を表し、ｑは１〜３の整数を表し、ｒは１〜１９の整数を表し、ｓは１〜３の整数を表わす。）

(In the formula, R ¹⁰ is the same group as R ¹⁰ in the general formula (2), if R ¹⁰ is two or more in the group may be different even in the same, R ^{10 '} Is a group in which one or more hydrogen atoms of R ¹⁰ are substituted with a hydroxyl group, Z ¹⁰ and Z ¹¹ represent a divalent group selected from the following group A, and p represents an integer of 1 to 3. Q represents an integer of 1 to 3, r represents an integer of 1 to 19, and s represents an integer of 1 to 3.)

（式中、ｑは、群１と同じである。）

(Wherein q is the same as group 1)

  Among the compounds represented by the general formula (1), the compound represented by the following general formula (7) is preferable because it is easy to produce.

（式中Ｒ¹及びＸは上記一般式（１）と同じであり、Ｒ²、Ｒ³、Ｒ⁴及びＲ⁵は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、炭素原子数１〜８のアルキル基、炭素原子数１〜８のアルコキシ基、炭素原子数１〜８のハロゲン化アルキル基又は炭素原子数１〜８のハロゲン化アルコキシ基を表し、Ｒ³とＸ、Ｒ⁴とＸはそれぞれ連結して環構造を形成してもよい。）

(Wherein R ¹ and X are the same as those in the general formula (1), and R ² , R ³ , R ⁴ and R ⁵ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, Represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or a halogenated alkoxy group having 1 to 8 carbon atoms, and R ³ and X , R ⁴ and X may be linked to form a ring structure.)

The halogen atom represented by R ² , R ³ , R ⁴ and R ⁵ in the general formula (7), an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and 1 to 1 carbon atom. Examples of the halogenated alkyl group having 8 and the halogenated alkoxy group having 1 to 8 carbon atoms include the groups exemplified in the description of A or R ¹ in the general formula (1).
Examples of the ring structure formed by connecting R ³ and X or R ⁴ and X include those exemplified as the ring structure formed by connecting X and A in the general formula (1).

  Specific examples of the compound represented by the general formula (1) include the following compound No. 1-No. 71, but the present invention is not limited to these compounds.

The method for producing the compound represented by the general formula (1) is not particularly limited. For example, A is a benzene ring, R ¹ is a hydrogen atom, X is an organic group represented by the general formula (2), A compound in which Z ¹ and Z ² in Formula (2) are —NR— can be produced according to the following reaction formula. That is, reacting N-substituted aniline (a) with phosphorus oxychloride in dimethylformamide (DMF) to obtain an aldehyde (b), and then reacting malononitrile (c) in ethanol in the presence of triethylamine (TEA). Thus, the compound represented by the general formula (1) can be obtained.

（式中、Ｒ及びＸ¹は上記一般式（１）と同じである。）

(In the formula, R and X ¹ are the same as those in the general formula (1).)

  The dye (A) of this invention should just contain the compound represented by the said General formula (1) at least 1 type, and can be used individually or in combination of multiple types. Moreover, it is also possible to use a well-known dye other than the compound represented by the said General formula (1). Known dyes include, for example, azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes, Examples thereof include phthalocyanine dyes and cyanine dyes, and a plurality of these may be used in combination.

  In the dye (A) of the present invention, the content of the compound represented by the general formula (1) is preferably 50 to 100% by mass, more preferably 70 to 100% by mass. When the content of the compound represented by the general formula (1) is less than 50% by mass, the solubility in a solvent may be reduced or the heat resistance may be reduced.

  The dye (A) of the present invention is used as a colored photosensitive composition and a colored alkali-developable photosensitive composition described below, as well as an optical filter used for displays and optical lenses, a silver salt photographic photosensitive material, and a dyed article. , Paints, optical recording dyes and the like.

  Next, the colored photosensitive composition and the colored alkali-developable photosensitive composition of the present invention (hereinafter also simply referred to as the colored composition of the present invention) will be described. In addition, about the point which is not demonstrated especially, the description demonstrated in the dye (A) of this invention is applied suitably.

The coloring composition of the present invention comprises the dye (A) of the present invention, a polymerizable compound (B) having an ethylenically unsaturated bond [a polymerizable compound having an ethylenically unsaturated bond and an ethylenically unsaturated bond (B ′). And a photopolymerization initiator (C), and if necessary, an inorganic pigment and / or an organic pigment (
D).

<Dye (A)>
The dye (A) of the present invention is as described above. In the colored composition of the present invention, the content of the dye (A) of the present invention is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass in the colored composition of the present invention. . If the content of the dye (A) is less than 0.01% by mass, a desired concentration of color may not be obtained in the cured product of the present invention. If the content is more than 50% by mass, the dye (A A) precipitation may occur.

<Polymerizable compound (B) having an ethylenically unsaturated bond>
The polymerizable compound (B) having an ethylenically unsaturated bond is not particularly limited, and those conventionally used in photosensitive compositions can be used. For example, ethylene, propylene, butylene, isobutylene can be used. , Vinyl chloride, vinylidene chloride, vinylidene fluoride, tetrafluoroethylene and other unsaturated aliphatic hydrocarbons; (meth) acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, highmic acid, Crotonic acid, isocrotonic acid, vinyl acetic acid, allyl acetic acid, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl] , Ω-carboxypolycaprolactone mono (meth) acrylate, etc. Mono (meth) acrylate, hydroxyethyl (meth) acrylate malate, hydroxypropyl (meth) acrylate malate, dicyclopentadiene malate or one carboxyl group and two or more (meth) acryloyl groups Unsaturated polybasic acids such as polyfunctional (meth) acrylates having 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate, the following compound No. 121-No. 124, methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (meth) acrylate, (meta ) Ethylhexyl acrylate, (meth) acrylic Phenoxyethyl, tetrahydrofuryl (meth) acrylate, vinyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol Di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, trimethylolethanetri (Meth) acrylate, trimethylolpropane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, pentaerythritol Unsaturated monobasic acids such as tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, tricyclodecane dimethylol di (meth) acrylate, tri [(meth) acryloylethyl] isocyanurate, polyester (meth) acrylate oligomers and the like Esters of polyhydric alcohols or polyphenols; metal salts of unsaturated polybasic acids such as zinc (meth) acrylate and magnesium (meth) acrylate; maleic anhydride, itaconic anhydride, citraconic anhydride, methyl Tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydro Phthalic anhydride-anhydrous Maleic acid adducts, acid anhydrides of unsaturated polybasic acids such as dodecenyl succinic anhydride, methyl hymic anhydride; (meth) acrylamide, methylene bis- (meth) acrylamide, diethylenetriamine tris (meth) acrylamide, xylylene bis (meth) Unsaturated monobasic acids such as acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide and amides of polyvalent amines; unsaturated aldehydes such as acrolein; (meth) acrylonitrile, α-chloroacrylonitrile, cyanide Unsaturated nitriles such as vinylidene and allyl cyanide; styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinyl Unsaturated aromatic compounds such as nylphenol, vinyl sulfonic acid, 4-vinylbenzene sulfonic acid, vinyl benzyl methyl ether, vinyl benzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; vinyl amine, allyl amine, N-vinyl pyrrolidone, vinyl Unsaturated amine compounds such as piperidine; vinyl alcohols such as allyl alcohol and crotyl alcohol; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether, allyl glycidyl ether; maleimide, N-phenylmaleimide, N -Unsaturated imides such as cyclohexylmaleimide; Indenes such as indene and 1-methylindene; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene Macromolecules having a mono (meth) acryloyl group at the end of a polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, polysiloxane, etc .; vinyl chloride, vinylidene chloride, divinyls Cuxinate, diallyl phthalate, triallyl phosphate, triallyl isocyanurate, vinyl thioether, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, hydroxyl group-containing vinyl monomers and vinyl isocyanate compounds of polyisocyanate compounds, hydroxyl groups Hydroxyl-containing polyfunctionals such as vinyl monomers and polyepoxy compounds containing vinyl epoxy compounds, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, etc. Reaction products of polyfunctional isocyanates such as acrylate and tolylene diisocyanate and hexamethylene diisocyanate, hydroxyl-containing polyfunctional acrylates such as pentaerythritol triacrylate and dipentaerythritol pentaacrylate, succinic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, etc. The polyfunctional acrylate which has an acid value which is a reaction product of a dibasic acid anhydride is mentioned.

  These polymerizable compounds can be used alone or in admixture of two or more, and when used in admixture of two or more, they are copolymerized in advance and used as a copolymer. May be.

  In the colored composition of the present invention, the polymerizable compound (B ′) having an ethylenically unsaturated bond having alkali developability (hereinafter referred to as ethylenic) is used as the polymerizable compound (B) having an ethylenically unsaturated bond. When an alkali-developable compound (B ′) having an unsaturated bond is used, the colored photosensitive composition of the present invention becomes a colored alkali-developable photosensitive composition. Examples of the alkali-developable compound (B ′) having an ethylenically unsaturated bond include (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, and butyl. (Meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, cyclohexyl (meth) acrylate, phenoxyethyl (meth) acrylate, 2-ethylhexyl (meth) (Meth) acrylic acid esters such as acrylate, isobornyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate; N-vinylpyrrolidone; styrene and its Conductors, styrenes such as α-methylstyrene; acrylamides such as (meth) acrylamide, methylol (meth) acrylamide, alkoxymethylol (meth) acrylamide, diacetone (meth) acrylamide; (meth) acrylonitrile, ethylene, propylene, butylene, Other vinyl compounds such as vinyl chloride and vinyl acetate, and macromonomers such as polymethyl methacrylate macromonomer and polystyrene macromonomer, monomethacrylate of tricyclodecane skeleton, N-phenylmaleimide, methacryloyloxymethyl-3-ethyloxetane, etc. And a copolymer of (meth) acrylic acid and an isocyanate compound having an unsaturated bond such as Karenz MOI and AOI manufactured by Showa Denko K.K. Copolymers of silyl acids, novolac epoxy compounds such as phenol and / or cresol novolac epoxy resins, novolak epoxy resins having a biphenyl skeleton and a naphthalene skeleton, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds, and the like A polyphenylmethane type epoxy resin having a functional epoxy group, obtained by allowing an unsaturated monobasic acid to act on an epoxy group such as an epoxy compound represented by the following general formula (I), and further reacting with a polybasic acid anhydride Resins can be used. These monomers can be used individually by 1 type or in mixture of 2 or more types. The alkali-developable compound (B ′) having an ethylenically unsaturated bond preferably contains 0.2 to 1.0 equivalent of an unsaturated group.

（式中、Ｘ⁴¹は直接結合、メチレン基、炭素原子数１〜４のアルキリデン基、炭素原子数３〜２０の脂環式炭化水素基、−Ｏ−、−Ｓ−、−ＳＯ₂−、−ＳＳ−、−ＳＯ−、−ＣＯ−、−ＯＣＯ−又は上記式（ｘ）、（ｙ）若しくは（ｚ）で表される置換基を表し、該アルキリデン基はハロゲン原子で置換されていてもよく、Ｒ⁴¹、Ｒ⁴²、Ｒ⁴³及びＲ⁴⁴は、それぞれ独立に、水素原子、炭素原子数１〜５のアルキル基、炭素原子数１〜８のアルコキシ基、炭素原子数２〜５のアルケニル基又はハロゲン原子を表し、上記アルキル基、アルコキシ基及びアルケニル基はハロゲン原子で置換されていてもよく、ｒは０〜１０の整数である。）

(In the formula, X ⁴¹ is a direct bond, a methylene group, an alkylidene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, —O—, —S—, —SO ₂ —, -SS-, -SO-, -CO-, -OCO- or a substituent represented by the above formula (x), (y) or (z), wherein the alkylidene group may be substituted with a halogen atom R ⁴¹ , R ⁴² , R ⁴³ and R ⁴⁴ are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl having 2 to 5 carbon atoms. Represents a group or a halogen atom, and the alkyl group, alkoxy group and alkenyl group may be substituted with a halogen atom, and r is an integer of 0 to 10.)

Examples of the unsaturated monobasic acid that acts on the epoxy group of the epoxy compound include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl methacrylate / malate, and the like. Examples thereof include hydroxyethyl acrylate / malate, hydroxypropyl methacrylate / malate, hydroxypropyl acrylate / malate, and dicyclopentadiene / malate.
In addition, the polybasic acid anhydride to be acted after the unsaturated monobasic acid is allowed to act is biphenyltetracarboxylic dianhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, trimellitic anhydride , Pyromellitic anhydride, 2,2'-3,3'-benzophenone tetracarboxylic anhydride, ethylene glycol bisanhydro trimellitate, glycerol tris anhydro trimellitate, hexahydro phthalic anhydride, methyl tetrahydro phthalic anhydride Acid, nadic anhydride, methyl nadic anhydride, trialkyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2- Dicarboxylic anhydride, trialkyltetrahydrophthalic anhydride Maleic anhydride adduct, dodecenyl succinic anhydride, and anhydride and methyl high Mick acid.

The reaction molar ratio of the epoxy compound, the unsaturated monobasic acid and the polybasic acid anhydride is preferably as follows. That is, in the epoxy adduct having a structure in which 0.1 to 1.0 carboxyl groups of the unsaturated monobasic acid are added to one epoxy group of the epoxy compound, the hydroxyl group of the epoxy adduct is 1 It is preferable that the acid anhydride structure of the polybasic acid anhydride has a ratio of 0.1 to 1.0.
Reaction of the said epoxy compound, the said unsaturated monobasic acid, and the said polybasic acid anhydride can be performed in accordance with a conventional method.

  In order to improve the developability of the colored alkali-developable photosensitive composition of the present invention by adjusting the acid value, a monofunctional or polyfunctional epoxy compound may be used together with the alkali-developable compound having an ethylenically unsaturated bond. it can. The alkali-developable compound having an ethylenically unsaturated bond preferably has a solid content acid value in the range of 5 to 120 mgKOH / g, and the use amount of the monofunctional or polyfunctional epoxy compound satisfies the acid value. It is preferable to select as follows.

  Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl. Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, hexadecyl glycidyl ether, 2-ethylhexyl glycidyl ether, Allyl glycidylate , Propargyl glycidyl ether, p-methoxyethyl glycidyl ether, phenyl glycidyl ether, p-methoxy glycidyl ether, p-butylphenol glycidyl ether, cresyl glycidyl ether, 2-methyl cresyl glycidyl ether, 4-nonylphenyl glycidyl ether, benzyl glycidyl ether Ether, p-cumylphenyl glycidyl ether, trityl glycidyl ether, 2,3-epoxypropyl methacrylate, epoxidized soybean oil, epoxidized linseed oil, glycidyl butyrate, vinylcyclohexane monooxide, 1,2-epoxy-4-vinyl Cyclohexane, styrene oxide, pinene oxide, methyl styrene oxide, cyclohexene oxide, propylene oxide, the above compound No.122 and no. 123 etc. are mentioned.

It is preferable to use one or more selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers as the polyfunctional epoxy compound because a colored alkali-developable photosensitive composition with better characteristics can be obtained. As the bisphenol type epoxy compound, an epoxy compound represented by the above general formula (I) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used. Examples of the glycidyl ethers include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (glycidyloxymethyl) methane, 1,1,1,1- tetra (glycidyloxymethyl) include methane.
Other novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxies such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; heterocyclic epoxy compounds such as 1,3-diglycidyl-5,5-dimethylhydantoin and triglycidyl isocyanurate; Dioxide compounds such as cyclopentadiene dioxide; naphthalene type epoxy compounds, triphenylmethane type epoxy compounds, dicyclopentadiene type epoxy compounds and the like can also be used.

  In the colored composition of the present invention, the content of the polymerizable compound (B) having the ethylenically unsaturated bond (including the alcal developable compound (B ′) having the ethylenically unsaturated bond) is the content of the present invention. In a coloring composition, 30-99 mass%, Especially 60-95 mass% is preferable. If the content of the polymerizable compound (B) having an ethylenically unsaturated bond is less than 30% by mass, the mechanical strength of the cured product is insufficient and cracks occur, or if it has alkali developability, development failure occurs. If it is larger than 99% by mass, curing due to exposure becomes insufficient and tackiness occurs, and if it has alkali developability, the development time becomes long and the cured part may be damaged by alkali. There is a case.

<Photopolymerization initiator (C)>
As the photopolymerization initiator (C), conventionally known compounds can be used. For example, benzophenone, phenylbiphenyl ketone, 1-hydroxy-1-benzoylcyclohexane, benzoin, benzyldimethyl ketal, 1-benzyl- 1-dimethylamino-1- (4′-morpholinobenzoyl) propane, 2-morpholyl-2- (4′-methylmercapto) benzoylpropane, thioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, diethylthioxanthone, ethyl Anthraquinone, 4-benzoyl-4′-methyldiphenyl sulfide, benzoin butyl ether, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2- (4′-isopropyl) benzoylpropane, 4-butyl Benzoyltrichloromethane, 4-phenoxybenzoyldichloromethane, methyl benzoylformate, 1,7-bis (9′-acridinyl) heptane, 9-n-butyl-3,6-bis (2′-morpholinoisobutyroyl) carbazole, 2 -Methyl-4,6-bis (trichloromethyl) -s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2-naphthyl-4,6-bis (trichloromethyl) -s -Triazine, 2,2-bis (2-chlorophenyl) -4,5,4 ', 5'-tetraphenyl-1-2'-biimidazole, 4,4-azobisisobutyronitrile, triphenylphosphine, Examples include camphorquinone and benzoyl peroxide, and commercially available products include N-1414, N-1717, N-1919, PZ-4. 8, (manufactured by (Corporation) ADEKA Corporation) NCI-831, NCI-930, IRGACURE369, IRGACURE907, IRGACURE OXE 01, IRGACURE OXE02 (BASF (Co.) Co., Ltd.).

  Among these photopolymerization initiators (C), 1-benzyl-1-dimethylamino-1- (4′-morpholinobenzoyl) propane and 2-morpholyl-2- (4′-methylmercapto) are preferable from the viewpoint of curing speed. Benzoylpropane, IRGACURE 369, IRGACURE 907, IRGACURE OXE 01, IRGACURE OXE 02 are preferred.

  In the colored composition of the present invention, the content of the photopolymerization initiator (C) is preferably 0.1 to 30% by mass, particularly preferably 0.5 to 10% by mass in the colored composition of the present invention. When the content of the photopolymerization initiator (C) is less than 0.1% by mass, curing by exposure may be insufficient. When the content is more than 30% by mass, the initiator (C) is contained in the resin composition. May precipitate.

<Inorganic pigment and / or organic pigment (D)>
The coloring composition of the present invention may further contain an inorganic pigment and / or an organic pigment (D). These pigments can be used alone or in admixture of two or more.

Examples of the inorganic pigment and / or organic pigment (D) include nitroso compounds, nitro compounds, azo compounds, diazo compounds, xanthene compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, isoindoline. Compounds, quinacridone compounds, anthanthrone compounds, perinone compounds, perylene compounds, diketopyrrolopyrrole compounds, thioindigo compounds, dioxazine compounds, triphenylmethane compounds, quinophthalone compounds, naphthalene tetracarboxylic acids; azo dyes, metal complex compounds of cyanine dyes; lakes Pigment: Carbon black obtained by furnace method, channel method, thermal method, or carbon black such as acetylene black, ketjen black or lamp black The carbon black prepared and coated with an epoxy resin, the carbon black previously dispersed with a resin in a solvent and adsorbed 20 to 200 mg / g of the resin, the carbon black is acidic or alkaline Surface treatment, average particle size of 8 nm or more, DBP oil absorption of 90 ml / 100 g or less, CO in volatile matter at 950 ° C., total oxygen calculated from CO ₂ is 9 mg per 100 m ^{2 of} carbon black surface area Above, graphite, graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon aerogel, fullerene; aniline black, pigment black 7, titanium black; hydrophobic resin, chromium oxide green, Milori blue, cobalt green, koval Blue, manganese, ferrocyanide, phosphate ultramarine, bitumen, ultramarine, cerulean blue, pyridian, emerald green, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, synthetic An inorganic content such as iron black or amber or an organic pigment can be used. These pigments can be used alone or in combination.

  As said inorganic pigment and / or organic pigment (D), a commercially available pigment can also be used, for example, pigment red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41. 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59 , 60, 61, 62, 64, 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 3, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185; Pigment Green 7, 10, 36; Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 22, 24, 56, 60, 61, 62, 64; Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50, and the like.

  In the colored composition of the present invention, the content of the inorganic pigment and / or organic pigment (D) is preferably 0 to 350 with respect to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond. Part by mass, more preferably 0 to 250 parts by mass. When it exceeds 350 parts by mass, the light transmittance of the colored composition of the present invention, particularly the cured product using the colored alkali-developable photosensitive composition, and the color filter for display device is lowered, and the luminance of the display device is lowered. Therefore, it is not preferable.

<Solvent (E)>
A solvent (E) can be further added to the colored composition of the present invention. As the solvent, usually, a solvent capable of dissolving or dispersing each of the above components (the dye (A) of the present invention) as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, Ketones such as methyl isobutyl ketone, cyclohexanone, 2-heptanone; ether solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether; methyl acetate, acetic acid Ester solvents such as ethyl, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; cellos such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether Rub solvent; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2 -Ether ester solvents such as acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethoxyethyl propionate; BTX solvents such as benzene, toluene, xylene; hexane, heptane, octane, cyclohexane, etc. Terpene hydrocarbon oils such as turpentine oil, D-limonene, pinene, etc .; mineral spirits, swazol # 310 (Cosmo Matsuyama Oil Co., Ltd.), Sol Paraffin solvents such as osso # 100 (Exxon Chemical Co., Ltd.); Halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, and 1,2-dichloroethane; Halogenated aroma such as chlorobenzene Group hydrocarbon solvents; carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, water, etc. These solvents can be used as one or a mixture of two or more. Among these, ketones, ether ester solvents, and the like, particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, and the like are preferable because the compatibility of the resist and the photopolymerization initiator is good in the photosensitive composition.

  In the colored composition of the present invention, the amount of the solvent (E) used is preferably such that the concentration of the composition other than the solvent (E) is 5 to 30% by mass, It is difficult to increase the thickness and it is not preferable because it cannot sufficiently absorb light of a desired wavelength. When the amount exceeds 30% by mass, the storage stability of the composition due to the precipitation of the composition is decreased, and the viscosity is improved. Is unfavorable because of lowering.

  The coloring composition of the present invention can further contain an inorganic compound. Examples of the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Among these, titanium oxide, silica, layered clay mineral, silver and the like are preferable. In the colored composition of the present invention, the content of the inorganic compound is preferably 0.1 to 50 parts by mass, more preferably 100 parts by mass with respect to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond. It is 0.5-20 mass parts, and these inorganic compounds can use 1 type (s) or 2 or more types.

  These inorganic compounds are used, for example, as fillers, antireflection agents, conductive agents, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink repellents, and the like.

  In the coloring composition of the present invention, when a pigment and / or an inorganic compound is used, a dispersant can be added. As the dispersant, any pigment or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie, Inc. can be used. Polymer dispersant made of ether, polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g Are preferably used.

  In addition, the coloring composition of the present invention includes, if necessary, thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; plasticizer; adhesion promoter; filler; Conventional additives such as an agent, a leveling agent, a surface conditioner, an antioxidant, an ultraviolet absorber, a dispersion aid, a coagulation inhibitor, a catalyst, an effect accelerator, a cross-linking agent, and a thickener can be added.

  In the colored composition of the present invention, optional components other than the dye (A) of the present invention, the polymerizable compound (B) having an ethylenically unsaturated bond, and the photopolymerization initiator (C) (however, inorganic pigment and / or organic) The content of the pigment (D) and the solvent (E) is appropriately selected depending on the purpose of use and is not particularly limited, but is preferably 100 masses of the polymerizable compound (B) having an ethylenically unsaturated bond. 50 parts by mass or less in total with respect to parts.

Moreover, the characteristic of the hardened | cured material which consists of a coloring composition of this invention can also be improved by using another organic polymer with the polymeric compound (B) which has the said ethylenically unsaturated bond. Examples of the other organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid- Methyl methacrylate copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide , Saturated polyester, phenol resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, etc., among these, polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, epoxy resin It is preferred.
When using another organic polymer, the usage-amount is preferably 10-500 mass parts with respect to 100 mass parts of polymeric compounds (B) which have the said ethylenically unsaturated bond.

  The colored composition of the present invention can further contain a monomer having an unsaturated bond, a chain transfer agent, a sensitizer, a surfactant, a silane coupling agent, a melamine compound, and the like.

  Examples of the monomer having an unsaturated bond include: 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, isobutyl acrylate, n-octyl acrylate, isooctyl acrylate, isononyl acrylate, stearyl acrylate, acrylic acid Methoxyethyl, dimethylaminoethyl acrylate, zinc acrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, butyl methacrylate, methacrylic acid Tertiary butyl, cyclohexyl methacrylate, trimethylolpropane trimethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentae Thritol tetraacrylate, pentaerythritol triacrylate, bisphenol A diglycidyl ether (meth) acrylate, bisphenol F diglycidyl ether (meth) acrylate, bisphenol Z diglycidyl ether (meth) acrylate, tripropylene glycol di (meth) acrylate, etc. Can be mentioned.

  As the chain transfer agent or sensitizer, a sulfur atom-containing compound is generally used. For example, thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N- (2-mercaptopropionyl) glycine, 2-mercaptonicotinic acid, 3- [N- (2-mercaptoethyl) carbamoyl] propionic acid, 3- [N- (2-mercaptoethyl) amino] propionic acid, N- (3-mercaptopropionyl) alanine, 2-mercaptoethanesulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2 -Propanediol, 1-mercapto-2-propyl Panol, 3-mercapto-2-butanol, mercaptophenol, 2-mercaptoethylamine, 2-mercaptoimidazole, 2-mercaptobenzimidazole, 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, mercaptoacetic acid, trimethylolpropane tris Mercapto compounds such as (3-mercaptopropionate) and pentaerythritol tetrakis (3-mercaptopropionate), disulfide compounds obtained by oxidizing the mercapto compound, iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2 -Iodinated alkyl compounds such as iodoethanesulfonic acid and 3-iodopropanesulfonic acid, trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-methyl Captoisobutyrate), hexanedithiol, decanedithiol, 1,4-dimethylmercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, Butanediol bisthiopropionate, trimethylolpropane tristhiopropionate, trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, Compound No. 125, aliphatic polyfunctional thiol compounds such as trimercaptopropionic acid tris (2-hydroxyethyl) isocyanurate, Karenz MT BD1, PE1, NR1 manufactured by Showa Denko KK and the like.

  Examples of the surfactant include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.

  As the silane coupling agent, for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, KBE-9007, KBM-502, KBE-403 and the like, silane cups having isocyanate group, methacryloyl group, epoxy group A ring agent is preferably used.

Examples of the melamine compound include all or part of active methylol groups (CH ₂ OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified. Here, examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other. Moreover, the methylol group which is not alkyletherified may be self-condensed within one molecule, or may be condensed between two molecules, and as a result, an oligomer component may be formed. Specifically, hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used. Among these, alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.

  The coloring composition of the present invention is a known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc. It can be applied on the supporting substrate. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base | substrate, There is no restriction | limiting in the application method.

  Moreover, as the light source of the active light used when curing the colored composition of the present invention, one that emits light having a wavelength of 300 to 450 nm can be used, for example, ultrahigh pressure mercury, mercury vapor arc, carbon arc. Xenon arc or the like can be used.

  Furthermore, by using laser light as the exposure light source, the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy. As the laser light, light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs the region from visible to infrared is added.

  The colored composition of the present invention (or its cured product) is a photocurable paint or varnish, a photocurable adhesive, a printed circuit board, or a color display liquid crystal display such as a color TV, PC monitor, portable information terminal, digital camera, etc. Color filters in panels, color filters for CCD image sensors, electrode materials for plasma display panels, powder coatings, printing inks, printing plates, adhesives, dental compositions, resin for stereolithography, gel coats, photoresists for electronics , Electroplating resist, etching resist, both liquid and dry film, solder resist, structure for manufacturing color filters for various display applications or in the manufacturing process of plasma display panel, electroluminescent display device and LCD A composition for encapsulating resist, electrical and electronic components -Resist, magnetic recording materials, micromechanical parts, waveguides, optical switches, plating masks, etching masks, color test systems, glass fiber cable coatings, stencils for screen printing, materials for producing 3D objects by stereolithography Holographic recording material, image recording material, fine electronic circuit, decoloring material, decoloring material for image recording material, decoloring material for image recording material using microcapsules, photoresist material for printed wiring board, UV and visible It can be used for various applications such as a photoresist material for a laser direct image system, a photoresist material used for forming a dielectric layer in the sequential lamination of printed circuit boards, or a protective film, and the application is not particularly limited.

  The colored composition of the present invention (particularly the colored alkali-developable photosensitive composition) is used for the purpose of forming pixels of a color filter, and in particular, forms a color filter for a display device for an image display device such as a liquid crystal display panel. It is useful as a photosensitive composition.

  The color filter for display device includes (1) a step of forming a coating film of the colored composition of the present invention (particularly a colored alkali-developable photosensitive composition) on a substrate, and (2) a predetermined pattern shape on the coating film. Preferably formed by a step of irradiating actinic light through a mask having, (3) a step of developing a film after exposure with a developer (particularly an alkali developer), and (4) a step of heating the film after development. Is done. The colored composition of the present invention is also useful as an inkjet type colored composition without a development step.

  Next, the novel compound of the present invention will be described. In addition, about the point which is not demonstrated especially, the description demonstrated in the dye (A) of this invention is applied suitably.

The novel compound of the present invention corresponds to the compound represented by the general formula (1 ′) among the compounds used in the above-described dye (A) of the present invention. That is, the novel compound of the present invention is a compound that satisfies any of the following conditions (i) to (iii) in addition to the conditions defined in the general formula (1).
(I) It has an aromatic ring in the organic group represented by X ′.
(Ii) The organic group represented by X ′ has at least two hydroxyl groups.
(Iii) The organic group represented by X ′ has at least one acrylic group, methacryl group, styryl group or epoxy group.

Examples of the organic group having an aromatic ring represented by X 'in conditions of (i), for example, benzene, naphthalene, anthracene, fluorene, biphenylene, Z ¹ and Z groups such terphenylene is in the general formula (2) ^And a divalent group substituted with ² or a group selected from the following [Chemical 27].

The organic group having at least two or more hydroxyl groups represented by X ′ under the condition (ii) is a divalent carbon chain having 1 to 35 carbon atoms represented by X ¹ in the general formula (2). A hydrogen group, a divalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 35 carbon atoms, and a heterocyclic group having 2 to 35 carbon atoms are Z ¹ and In the divalent group substituted with Z ² , in addition to those in which two or more hydrogen atoms are substituted with a hydroxyl group, the above divalent chain hydrocarbon group having 1 to 35 carbon atoms, a divalent carbon atom A C3-C35 alicyclic hydrocarbon group, a divalent C6-C35 aromatic hydrocarbon group are bonded to -NR-, and R has a hydroxyl group, and the like.
Examples of the organic group having at least one acrylic group, methacryl group, styryl group, and epoxy group represented by X ′ under the condition (iii) include a divalent carbon represented by X ¹ in the general formula (2). A chain hydrocarbon group having 1 to 35 atoms, a divalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 35 carbon atoms, and 2 to 2 carbon atoms In the divalent group in which 35 heterocyclic groups are substituted with Z ¹ and Z ² , 1 to 5 hydrogen atoms are each independently substituted with an epoxy group, a 4-vinylphenyl group, an acryloyloxy group or a methacryloyloxy group. And the like.

  Hereinafter, although an example etc. are given and the present invention is explained still in detail, the present invention is not limited to these examples.

Examples 1-1 to 1-3 show synthesis examples of the novel compound of the present invention (the dye of the present invention). In Evaluation Example 1, the novel compound of the present invention obtained in Examples 1-1 to 1-3 was obtained. The absorption wavelength characteristics of the compound and the comparative compound were evaluated. In Evaluation Example 2, the solubility of the novel compound of the present invention and the comparative compound obtained in Examples 1-1 to 1-3 was evaluated.
Examples 2-1 and 2-2 and Comparative Example 2-1 show preparation examples of the present invention and a comparative colored alkali-developable photosensitive composition. In Evaluation Examples 3, 4 and Comparative Evaluation Example 1, The heat resistances of the present invention and comparative colored alkali-developable photosensitive compositions obtained in 2-1, 2-2 and Comparative Example 2-1 were evaluated.

[Examples 1-1 to 1-3] Compound No. Synthesis of 1 to 3 DMF was placed in a 300 ml four-necked flask and cooled with ice, and phosphorus oxychloride was added dropwise and reacted for 1 hour under ice cooling. Thereafter, a DMF solution of the corresponding N-substituted aniline was added dropwise under ice cooling, and after the addition, the temperature was raised to 80 ° C. and reacted at 80 ° C. for 2 hours. After cooling to room temperature, the reaction solution was dropped into an aqueous sodium acetate solution and extracted with chloroform. The organic layer was evaporated under reduced pressure to obtain an aldehyde form.
The obtained aldehyde, TEA and ethanol were mixed, and malononitrile was added dropwise with stirring. After dropping, the reaction solution was heated to reflux and reacted for 2 hours. After the reaction, the mixture was cooled, and the precipitated solid was collected by filtration, washed and dried to obtain a yellow solid. It was confirmed by ¹ H-NMR and IR that the obtained yellow crystals were the target product. The results are shown in the following [Table 1] to [Table 3].

[Evaluation Example 1] Evaluation of absorption wavelength characteristics Compound Nos. Obtained in Examples 1-1 to 1-3. 1-3 and the following comparative compound No.1. The absorption wavelength characteristic of 1 was evaluated with a CHCl ₃ solution. The results are shown in [Table 4] below.

  From the results of the above [Table 4], it is clear that the dye comprising the compound represented by the general formula (1) of the present invention has an appropriate absorption wavelength.

[Evaluation Example 2] Solubility Evaluation Compound Nos. Obtained in Examples 1-1 to 1-3. 1 to 3 and the comparative compound No. 1 above. 1 DMF solubility was evaluated. The solubility was evaluated by adding DMF with stirring to 0.1 g of the compound while stirring to completely dissolve the compound. The results are shown in [Table 5] below.

  From the results of the above [Table 5], it is clear that the dye comprising the compound represented by the general formula (1) of the present invention is excellent in solubility.

[Example 2-1] Colored alkali-developable photosensitive composition No. Preparation of Step 1 <Step 1> Alkali-developable photosensitive composition No. 1 Preparation of 1 30.33 g of ACA Z250 (manufactured by Daicel Cytec) and 11.04 g of Aronix M-450 (manufactured by Toagosei Co., Ltd.) as component (B) and 1 of Irgacure 907 (manufactured by BASF) as component (C) .93 g, 36.60 g of PGMEA as component (E) and 20.08 g of cyclohexanone, and 0.01 g of FZ2122 (manufactured by Toray Dow Corning) as other components were mixed and stirred until insoluble matter disappeared, Developable photosensitive composition No. 1 was obtained.

<Step 2> Dye solution No. 1
As the component (A), the compound No. obtained in Example 1-1 was used. To 1.10 g of No. 1 was added 1.90 g of dimethylacetamide, dissolved by stirring, and dye solution No. 1 was added. It was set to 1.
<Step 3> Colored alkali-developable photosensitive composition No. Preparation of alkali-developable photosensitive composition No. 1 obtained in Step 1 1 and 5.0 g of the dye solution No. obtained in Step 2. 1 was mixed with 1.0 g and stirred until uniform, and the colored alkali-developable photosensitive composition No. 1 was mixed. 1 was obtained.

[Example 2-2] Colored alkali-developable photosensitive composition No. Preparation of the compound (A) in Step 2 of Example 2-1 was prepared as Compound No. 2 obtained in Example 1-2. Except for the change to 2, the colored alkali-developable photosensitive composition No. 1 was prepared in the same manner as Example 2-1. 2 was obtained.

[Comparative Example 2-1] Comparative colored alkali-developable photosensitive composition No. Preparation of Component 1 The compound of component (A) in Step 2 of Example 2-1 was compared with the above comparative compound No. 1. The comparative colored alkali-developable photosensitive composition No. 1 was prepared in the same manner as in Example 2-1, except that it was changed to 1. 1 was obtained.

[Evaluation Example 3]
The colored alkali-developable photosensitive composition No. obtained in Example 2-1. 1 was coated on a glass substrate under the condition of 410 rpm × 7 sec, and dried on a hot plate (90 ° C., 90 sec). The obtained coating film was exposed (150 mJ / cm ² ) with an ultra-high pressure mercury lamp and then post-baked at 230 ° C. for 30 minutes to prepare an evaluation sample film. A heat resistance test at 230 ° C. for 30 minutes was performed on the prepared sample film, and the color difference (ΔEab *) before and after the heat resistance test was examined. The results are shown in [Table 6].

[Evaluation Example 4 and Comparative Evaluation Example 1]
In the same manner as in Evaluation Example 3, the colored alkali-developable photosensitive composition No. obtained in Example 2-2 was used. 2 and comparative colored alkali-developable photosensitive composition No. 2 obtained in Comparative Example 2-1. An evaluation sample film was prepared using 1 and a heat resistance test was performed. The results are shown in [Table 6].

  From the results of [Table 6] above, it is clear that the colored alkali-developable photosensitive composition of the present invention has high heat resistance.

  From the above results, it is clear that the dye of the present invention has absorption in an appropriate wavelength region, and it is clear that the colored alkali-developable photosensitive composition using the dye and its cured product have high heat resistance. is there. Therefore, the dye and coloring composition of the present invention are useful for color filters for display devices and liquid crystal display panels using the same.

Claims (11)

A dye comprising at least one compound represented by the following general formula (1).

(In the formula, A represents a benzene ring, a naphthalene ring or an anthracene ring, and these rings are a halogen atom, a cyano group, a hydroxyl group, a nitro group, an alkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. An alkoxy group, a halogenated alkyl group having 1 to 8 carbon atoms, or a halogenated alkoxy group having 1 to 8 carbon atoms,
R ¹ represents a hydrogen atom, a phenyl group, a nitro group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or 1 to 1 carbon atom. 8 represents a halogenated alkoxy group,
X represents a nitrogen atom, -NR-, an oxygen atom, a sulfur atom, a phosphorus atom, -PR- or an organic group represented by the following general formula (2),
R represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group and arylalkyl group are , A halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be —COO—, —O—, —OCO—, —NHCO—, —NH— or — It may be interrupted by CONH-, and X and A may be linked to form a ring structure. )

(In the formula, X ¹ is —CR ²⁰ R ²¹ —, —NR ²⁰ —, a divalent chain hydrocarbon group having 1 to 35 carbon atoms, and an alicyclic carbon atom having 3 to 35 carbon atoms. A hydrogen group, a divalent aromatic hydrocarbon group having 6 to 35 carbon atoms, a divalent heterocyclic group having 2 to 35 carbon atoms, a group obtained by combining a plurality of these groups, or the following (x), (y ) Or (z), and the chain hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group are -COO-, -O-, -OCO- , -NHCO-, -NH-, -CONH-, -O-CONH- or -NHCO-O-
R ²⁰ and R ²¹ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms,
Z ¹ and Z ² each independently represent a direct bond, —O—, —S—, —SO ₂ —, —SO—, —NR ¹⁰ — or —PR ¹⁰ —,
R ¹⁰ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group, and arylalkyl group May be substituted with a halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be —COO—, —O—, —OCO—, —NHCO—, —NH— or It may be interrupted by -CONH-.
However, the number of carbon atoms of the organic group represented by the general formula (2) is in the range of 1 to 35. )

(In the formula, Z ¹² represents a hydrogen atom, a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, or an alkyl group or carbon having 1 to 10 carbon atoms. Represents a cycloalkyl group having 3 to 10 carbon atoms which may be substituted by an alkoxy group having 1 to 10 atoms,
Y ¹ represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom, and the alkyl group, alkoxy group, and alkenyl group are each a halogen atom. May be replaced with
d is an integer of 0-4. )

Wherein Y ² and Z ¹³ are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or an aryl having 6 to 20 carbon atoms which may be substituted with a halogen atom. Group, an aryloxy group having 6 to 20 carbon atoms that may be substituted with a halogen atom, an arylthio group having 6 to 20 carbon atoms that may be substituted with a halogen atom, and the number of carbon atoms that may be substituted with a halogen atom An arylalkenyl group having 8 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms which may be substituted with a halogen atom, a heterocyclic group having 2 to 20 carbon atoms which may be substituted with a halogen atom, and these groups; a represents a combination of plural groups or a halogen atom, a methylene group in the alkyl group and the arylalkyl group may be interrupted by an unsaturated bond, -O- or -S-, Z ¹³ , They may form a ring with the adjacent Z ¹³ each other,
e represents an integer of 0 to 4, f represents an integer of 0 to 8, g represents an integer of 0 to 4, h represents an integer of 0 to 4, and the sum of g and h is 2 to 4. It is an integer. ) X in the general formula (1) is an organic group represented by the general formula (2), and X ¹ in the general formula (2) is —COO—, —O—, —OCO—, —NHCO. It is a divalent chain hydrocarbon group having 1 to 35 carbon atoms interrupted by any of-, -NH-, -CONH-, -O-CONH- or -NHCO-O-. The dye according to claim 1. The dye according to claim 1 or 2, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (7).

(Wherein R ¹ and X are the same as those in the general formula (1), and R ² , R ³ , R ⁴ and R ⁵ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, Represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or a halogenated alkoxy group having 1 to 8 carbon atoms, and R ³ and X , R ⁴ and X may be linked to form a ring structure.) A colored photosensitive composition comprising a dye (A) comprising at least one compound represented by the following general formula (1), a polymerizable compound (B) having an ethylenically unsaturated bond, and a photopolymerization initiator (C). .

(In the formula, A represents a benzene ring, a naphthalene ring or an anthracene ring, and these rings are a halogen atom, a cyano group, a hydroxyl group, a nitro group, an alkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. An alkoxy group, a halogenated alkyl group having 1 to 8 carbon atoms, or a halogenated alkoxy group having 1 to 8 carbon atoms,
R ¹ represents a hydrogen atom, a phenyl group, a nitro group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or 1 to 1 carbon atom. 8 represents a halogenated alkoxy group,
X represents a nitrogen atom, -NR-, an oxygen atom, a sulfur atom, a phosphorus atom, -PR- or an organic group represented by the following general formula (2),
R represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group and arylalkyl group are , A halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be —COO—, —O—, —OCO—, —NHCO—, —NH— or — It may be interrupted by CONH-, and X and A may be linked to form a ring structure. )

(In the formula, X ¹ is —CR ²⁰ R ²¹ —, —NR ²⁰ —, a divalent chain hydrocarbon group having 1 to 35 carbon atoms, and an alicyclic carbon atom having 3 to 35 carbon atoms. A hydrogen group, a divalent aromatic hydrocarbon group having 6 to 35 carbon atoms, a divalent heterocyclic group having 2 to 35 carbon atoms, a group obtained by combining a plurality of these groups, or the following (x), (y ) Or (z), and the chain hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group are -COO-, -O-, -OCO- , -NHCO-, -NH-, -CONH-, -O-CONH- or -NHCO-O-
R ²⁰ and R ²¹ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms,
Z ¹ and Z ² each independently represent a direct bond, —O—, —S—, —SO ₂ —, —SO—, —NR ¹⁰ — or —PR ¹⁰ —,
R ¹⁰ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group, and arylalkyl group May be substituted with a halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be —COO—, —O—, —OCO—, —NHCO—, —NH— or It may be interrupted by -CONH-.
However, the number of carbon atoms of the organic group represented by the general formula (2) is in the range of 1 to 35. )

(In the formula, Z ¹² represents a hydrogen atom, a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, or an alkyl group or carbon having 1 to 10 carbon atoms. Represents a cycloalkyl group having 3 to 10 carbon atoms which may be substituted by an alkoxy group having 1 to 10 atoms,
Y ¹ represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom, and the alkyl group, alkoxy group, and alkenyl group are each a halogen atom. May be replaced with
d is an integer of 0-4. )

Wherein Y ² and Z ¹³ are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or an aryl having 6 to 20 carbon atoms which may be substituted with a halogen atom. Group, an aryloxy group having 6 to 20 carbon atoms that may be substituted with a halogen atom, an arylthio group having 6 to 20 carbon atoms that may be substituted with a halogen atom, and the number of carbon atoms that may be substituted with a halogen atom An arylalkenyl group having 8 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms which may be substituted with a halogen atom, a heterocyclic group having 2 to 20 carbon atoms which may be substituted with a halogen atom, and these groups; a represents a combination of plural groups or a halogen atom, a methylene group in the alkyl group and the arylalkyl group may be interrupted by an unsaturated bond, -O- or -S-, Z ¹³ , They may form a ring with the adjacent Z ¹³ each other,
e represents an integer of 0 to 4, f represents an integer of 0 to 8, g represents an integer of 0 to 4, h represents an integer of 0 to 4, and the sum of g and h is 2 to 4. It is an integer. )   The colored photosensitive composition according to claim 4, further comprising an inorganic pigment and / or an organic pigment (D). A dye (A) comprising at least one compound represented by the following general formula (1), a polymerizable compound (B ′) having an ethylenically unsaturated bond having alkali developability, and a photopolymerization initiator (C
) Containing a colored alkali-developable photosensitive composition.

(In the formula, A represents a benzene ring, a naphthalene ring or an anthracene ring, and these rings are a halogen atom, a cyano group, a hydroxyl group, a nitro group, an alkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. An alkoxy group, a halogenated alkyl group having 1 to 8 carbon atoms, or a halogenated alkoxy group having 1 to 8 carbon atoms,
R ¹ represents a hydrogen atom, a phenyl group, a nitro group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or 1 to 1 carbon atom. 8 represents a halogenated alkoxy group,
X represents a nitrogen atom, -NR-, an oxygen atom, a sulfur atom, a phosphorus atom, -PR- or an organic group represented by the following general formula (2),
R represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group and arylalkyl group are , A halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be —COO—, —O—, —OCO—, —NHCO—, —NH— or — It may be interrupted by CONH-, and X and A may be linked to form a ring structure. )

(In the formula, X ¹ is —CR ²⁰ R ²¹ —, —NR ²⁰ —, a divalent chain hydrocarbon group having 1 to 35 carbon atoms, and an alicyclic carbon atom having 3 to 35 carbon atoms. A hydrogen group, a divalent aromatic hydrocarbon group having 6 to 35 carbon atoms, a divalent heterocyclic group having 2 to 35 carbon atoms, a group obtained by combining a plurality of these groups, or the following (x), (y ) Or (z), and the chain hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group are -COO-, -O-, -OCO- , -NHCO-, -NH-, -CONH-, -O-CONH- or -NHCO-O-
R ²⁰ and R ²¹ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms,
Z ¹ and Z ² each independently represent a direct bond, —O—, —S—, —SO ₂ —, —SO—, —NR ¹⁰ — or —PR ¹⁰ —,
R ¹⁰ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group, and arylalkyl group May be substituted with a halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be —COO—, —O—, —OCO—, —NHCO—, —NH— or It may be interrupted by -CONH-.
However, the number of carbon atoms of the organic group represented by the general formula (2) is in the range of 1 to 35. )

(In the formula, Z ¹² represents a hydrogen atom, a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, or an alkyl group or carbon having 1 to 10 carbon atoms. Represents a cycloalkyl group having 3 to 10 carbon atoms which may be substituted by an alkoxy group having 1 to 10 atoms,
Y ¹ represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom, and the alkyl group, alkoxy group, and alkenyl group are each a halogen atom. May be replaced with
d is an integer of 0-4. )

Wherein Y ² and Z ¹³ are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or an aryl having 6 to 20 carbon atoms which may be substituted with a halogen atom. Group, an aryloxy group having 6 to 20 carbon atoms that may be substituted with a halogen atom, an arylthio group having 6 to 20 carbon atoms that may be substituted with a halogen atom, and the number of carbon atoms that may be substituted with a halogen atom An arylalkenyl group having 8 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms which may be substituted with a halogen atom, a heterocyclic group having 2 to 20 carbon atoms which may be substituted with a halogen atom, and these groups; a represents a combination of plural groups or a halogen atom, a methylene group in the alkyl group and the arylalkyl group may be interrupted by an unsaturated bond, -O- or -S-, Z ¹³ , They may form a ring with the adjacent Z ¹³ each other,
e represents an integer of 0 to 4, f represents an integer of 0 to 8, g represents an integer of 0 to 4, h represents an integer of 0 to 4, and the sum of g and h is 2 to 4. It is an integer. )   The colored photosensitive composition according to claim 6, further comprising an inorganic pigment and / or an organic pigment (D).   A colored photosensitive composition according to claim 4 or 5, or a cured product of the colored alkali-developable photosensitive composition according to claim 6 or 7.   A color filter for a display device, comprising at least a part of the cured product according to claim 8.   A liquid crystal display panel using the display device color filter according to claim 9. A compound represented by the following general formula (1 ′).

(In the formula, A ′ represents a benzene ring, a naphthalene ring or an anthracene ring, and these rings include a halogen atom, a cyano group, a hydroxyl group, a nitro group, an alkyl group having 1 to 8 carbon atoms, and an alkyl group having 1 to 1 carbon atoms. May be substituted with an alkoxy group having 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or a halogenated alkoxy group having 1 to 8 carbon atoms,
R ^{1 ′} is a hydrogen atom, a phenyl group, a cyano group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or 1 carbon atom. Represents a halogenated alkoxy group of ~ 8,
X ′ represents a nitrogen atom, —NR′—, an oxygen atom, a sulfur atom, a phosphorus atom, —PR′— or an organic group represented by the following general formula (2 ′),
R ′ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group, and arylalkyl group May be substituted with a halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be —COO—, —O—, —OCO—, —NHCO—, —NH— or -CONH- may be interrupted, and X 'and A' may be linked to form a ring structure,
Furthermore, any one of the following conditions (i) to (iii) is satisfied.
(I) It has an aromatic ring in the organic group represented by X ′.
(Ii) The organic group represented by X ′ has at least two hydroxyl groups.
(Iii) The organic group represented by X ′ has at least one acrylic group, methacryl group, styryl group or epoxy group. )

(In the formula, X ^{1 ′} is —CR ^{20 ′} R ^{21 ′} —, —NR ^{20 ′} —, a divalent chain hydrocarbon group having 1 to 35 carbon atoms, and a divalent carbon atom having 3 to 35 carbon atoms. An alicyclic hydrocarbon group, a divalent aromatic hydrocarbon group having 6 to 35 carbon atoms, a divalent heterocyclic group having 2 to 35 carbon atoms, a group obtained by combining a plurality of these groups, or the following (x '), A substituent represented by (y') or (z '), and the chain hydrocarbon group is -COO-, -O-, -OCO-, -NHCO-, -NH-,- May be interrupted with either CONH-, -O-CONH- or -NHCO-O-
R ^{20 ′} and R ^{21 ′} each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms,
Z ^{1 ′} and Z ^{2 ′} each independently represent a direct bond, —O—, —S—, —SO ₂ —, —SO—, —NR ^{10 ′} — or —PR ^{10 ′} —
R ^{10 ′} represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, and the alkyl group, aryl group, and arylalkyl The group may be substituted with a halogen atom, a hydroxyl group or a nitro group, and the methylene group in the alkyl group and arylalkyl group may be -COO-, -O-, -OCO-, -NHCO-, -NH-. Or it may be interrupted by -CONH-.
However, the number of carbon atoms of the organic group represented by the general formula (2 ′) is in the range of 1 to 35. )

(Wherein Z ^{12 ′} is a hydrogen atom, a phenyl group which may be substituted with an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms, or Represents a cycloalkyl group having 3 to 10 carbon atoms which may be substituted by an alkoxy group having 1 to 10 carbon atoms,
Y ^{1 ′} represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom, and the alkyl group, alkoxy group, and alkenyl group are each a halogen atom. May be substituted with atoms,
d 'is an integer of 0-4. )

Wherein Y ^{2 ′} and Z ^{13 ′} are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or 6 to 20 carbon atoms which may be substituted with a halogen atom. An aryloxy group having 6 to 20 carbon atoms which may be substituted with a halogen atom, an arylthio group having 6 to 20 carbon atoms which may be substituted with a halogen atom, or a carbon which may be substituted with a halogen atom An arylalkenyl group having 8 to 20 atoms, an arylalkyl group having 7 to 20 carbon atoms which may be substituted with a halogen atom, a heterocyclic group having 2 to 20 carbon atoms which may be substituted with a halogen atom, and these And a methylene group in the alkyl group and arylalkyl group may be interrupted by an unsaturated bond, —O— or —S—, and Z ^{13 '} May form a ring with adjacent Z ^13' ,
e ′ represents an integer of 0 to 4, f ′ represents an integer of 0 to 8, g ′ represents an integer of 0 to 4, h ′ represents an integer of 0 to 4, and g ′ and h ′ The sum is an integer of 2-4. )