KR102170466B1 - Coloring composition, colored cured film, and display device - Google Patents

Abstract

[화학식 (1)에 있어서, m은 0 내지 5의 정수를 나타내며, R¹ 내지 R⁴는 서로 독립적으로 수소 원자, 치환 또는 비치환된 탄화수소기 등을 나타내며, R⁵는 서로 독립적으로 1가의 기를 나타내되, 단 R¹ 내지 R⁴ 중 하나 이상은 하기의 요건 (ⅰ) 내지 (ⅴ)로부터 선택되는 기임:
(ⅰ) 치환 또는 비치환된 불포화 지방족 탄화수소기이거나, 또는 치환 또는 비치환된불포화 지환식 탄화수소기이되, 단 불포화 지방족 탄화수소기는 C-C 결합 간에 -CO-, -COO- 및 -CONH-로부터 선택되는 연결기를 가질 수도 있음,
(ⅱ) 불포화 지방족 탄화수소기로 치환된 지환식 탄화수소기이거나, 또는 불포화 지방족 탄화수소기 또는불포화 지환식 탄화수소기로 치환된 방향족 탄화수소기임,
(ⅲ) 치환 또는 비치환된 복소환기이거나, 또는 복소환기로 치환된탄화수소기임,
(ⅳ) -CN, -NO₂, -NH₂, -SH 및 -CONH₂로 이루어지는 군으로부터 선택되는 적어도 1종으로 치환된 탄화수소기임,
(ⅴ) 탄소수 11 이상의 치환 또는 비치환된 지방족 탄화수소기임.]An object of the present invention is to provide a colored composition capable of forming a colored cured film that can achieve both good voltage retention, high contrast, and high heat resistance when a dye is used as a colorant.
The solution of the present invention is a coloring composition containing a compound having a structure represented by the following formula (1), (B) a binder resin, and (C) a polymerizable compound.

[In Formula (1), m represents an integer of 0 to 5, R ¹ to R ⁴ independently represent a hydrogen atom, a substituted or unsubstituted hydrocarbon group, and the like, and R ⁵ independently of each other represent a monovalent group It is shown, provided that at least one of R ¹ to R ⁴ is a group selected from the following requirements (i) to (v):
(I) a substituted or unsubstituted unsaturated aliphatic hydrocarbon group, or a substituted or unsubstituted unsaturated alicyclic hydrocarbon group, provided that the unsaturated aliphatic hydrocarbon group is a linking group selected from -CO-, -COO- and -CONH- between CC bonds May have,
(Ii) an alicyclic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group, or an aromatic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group or an unsaturated alicyclic hydrocarbon group,
(Iii) a substituted or unsubstituted heterocyclic group, or a hydrocarbon group substituted with a heterocyclic group,
(Iv) a hydrocarbon group substituted with at least one selected from the group consisting of -CN, -NO ₂ , -NH ₂ , -SH and -CONH ₂ ,
(V) A substituted or unsubstituted aliphatic hydrocarbon group having 11 or more carbon atoms.]

Description

A colored composition, a colored cured film, and a display element TECHNICAL FIELD [COLORING COMPOSITION, COLORED CURED FILM, AND DISPLAY DEVICE}

The present invention relates to a colored composition, a colored cured film, and a display device, and more particularly, used for formation of a colored cured film used for a transmissive or reflective color liquid crystal display device, a solid-state imaging device, an organic EL display device, electronic paper, etc. It relates to a colored composition to be obtained, a colored cured film formed by using the colored composition, and a display element including the colored cured film.

When manufacturing a color filter using a colored radiation-sensitive composition, a pigment-dispersed colored radiation-sensitive composition is applied on a substrate, dried, and then a dried coating film is irradiated with radiation in a desired pattern shape (hereinafter referred to as ``exposure''). A method of obtaining a pixel of each color by developing (see, for example, Patent Documents 1 to 2) is known. In addition, a method of forming a black matrix using a photopolymerizable composition in which carbon black is dispersed (see, for example, Patent Document 3) is also known. Further, a method of obtaining a pixel of each color by an ink jet method using a pigment-dispersed colored resin composition (see, for example, Patent Document 4) is also known.

In recent years, high contrast of a liquid crystal display device and high precision of a solid-state imaging device are strongly demanded, and application of a dye as a colorant has been studied in order to realize these. For example, in Patent Document 5, use of a specific xanthene-based dye is proposed.

Japanese Patent Laid-Open (Hei) 2-144502 Japanese Patent Laid-Open (Hei) 3-53201 Japanese Patent Publication (Hei) 6-35188 Japanese Patent Application Publication No. 2000-310706 Japanese Patent Publication No. 2010-254964

However, when the dye proposed in Patent Document 5 is used, there is a problem that the contrast of the pixel is lowered. On the other hand, when a dye is used, there are many problems that the voltage retention and heat resistance of the color filter are deteriorated. Therefore, there is a strong demand for development of a coloring composition suitable for the production of a color filter that can achieve both good voltage retention, high contrast and high heat resistance.

Accordingly, an object of the present invention is to provide a colored composition capable of forming a colored cured film that can achieve both good voltage retention, high contrast and high heat resistance when a dye is used as a colorant, and applied as a colorant for the colored composition. It is to provide a possible compound. In addition, an object of the present invention is to provide a color filter comprising a colored cured film formed from the colored composition, and a display device including the color filter.

In view of this situation, the present inventors have conducted extensive research and found that the above problems can be solved by using a dye having a specific structure as a colorant, and the present invention has been completed.

That is, the present invention comprises (A) a colorant containing a compound having a structure represented by the following formula (1) (hereinafter also referred to as ``this colorant''), (B) a binder resin, and (C) a polymerizable compound. It is to provide a coloring composition.

[In Formula (1), m represents an integer of 0 to 5, and when m is an integer of 2 or more, a plurality of R ⁵ may be the same or different,

R ¹ to R ⁴ independently of each other represent a hydrogen atom, a substituted or unsubstituted hydrocarbon group, or a substituted or unsubstituted heterocyclic group, provided that the hydrocarbon group is from -CO-, -COO- and -CONH- between CC bonds May have a selected connector,

R ⁵ independently of each other represent a monovalent group,

Provided that at least one of R ¹ to R ⁴ is a group selected from the following requirements (i) to (v):

(I) a substituted or unsubstituted unsaturated aliphatic hydrocarbon group, or a substituted or unsubstituted unsaturated alicyclic hydrocarbon group, provided that the unsaturated aliphatic hydrocarbon group is a linking group selected from -CO-, -COO- and -CONH- between CC bonds May have,

(Ii) an alicyclic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group, or an aromatic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group or an unsaturated alicyclic hydrocarbon group,

(Iii) a substituted or unsubstituted heterocyclic group, or a hydrocarbon group substituted with a heterocyclic group,

(Iv) a hydrocarbon group substituted with at least one selected from the group consisting of -CN, -NO ₂ , -NH ₂ , -SH and -CONH ₂ (hereinafter also referred to as "substituent group α"),

(V) A substituted or unsubstituted aliphatic hydrocarbon group having 11 or more carbon atoms.]

In addition, the present invention is to provide a colored cured film formed using the colored composition, and a display element including the colored cured film. Here, the "colored cured film" means each color pixel, a black matrix, a black spacer, and the like used in a display element or a solid-state imaging element.

In addition, the present invention is to provide a compound having a structure represented by the formula (1).

When the colored composition of the present invention is used, a colored cured film excellent in voltage retention, contrast and heat resistance can be formed.

Therefore, the colored composition of the present invention can be very preferably used in the manufacture of a color liquid crystal display device, an organic EL display device, a display device such as electronic paper, and a solid-state image sensor such as a CMOS image sensor.

Hereinafter, the present invention will be described in detail.

Coloring composition

Hereinafter, the components of the colored composition of the present invention will be described in detail.

-(A) Colorant-

The coloring composition of this invention contains this coloring agent as (A) coloring agent.

Examples of the hydrocarbon group for R ¹ to R ⁴ include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. Further, these hydrocarbon groups may have a linking group selected from -CO-, -COO- and -CONH- between CC bonds.

The aliphatic hydrocarbon group may be saturated or unsaturated, and specific examples thereof include an alkyl group, an alkenyl group, and an alkynyl group. The number of carbon atoms of these aliphatic hydrocarbon groups is preferably 1 to 30, more preferably 1 to 24, and particularly preferably 1 to 20. In addition, these aliphatic hydrocarbon groups may be linear or branched. Specifically as an alkyl group, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, hexyl group, heptyl group, octyl group, nonyl group, de Sil group, undecyl group, 1-methyldecyl group, dodecyl group, 1-methylundecyl group, 1-ethyldecyl group, tridecyl group, tetradecyl group, tert-dodecyl group, pentadecyl group, 1-heptyloctyl group, hexa A decyl group, an octadecyl group, a heneikosan-1-yl group, a docosan-1-yl group, a trichosan-1-yl group, and a tetracosan-1-yl group may be mentioned. As the alkenyl group, for example, ethenyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 1,3-butadienyl group, 1-pentenyl group, 2-pentenyl group, 1- Hexenyl group, 2-ethyl-2-butenyl group, 2-octenyl group, (4-ethenyl)-5-hexenyl group, 2-decenyl group, etc. are mentioned. In addition, as an alkynyl group, for example, an ethynyl group, 1-propynyl group, 1-butynyl group, 1-pentynyl group, 3-pentynyl group, 1-hexynyl group, 2-ethyl-2-butynyl group, 2-octinyl group , (4-ethynyl)-5-hexynyl group, 2-decynyl group, etc. are mentioned. In addition, as a group having a linking group selected from -CO-, -COO- and -CONH- between CC bonds of the aliphatic hydrocarbon group, for example, (meth)acrylethyl group, (meth)acrylpropyl group, (meth)acrylamide Ethyl group, (meth)acrylamide propyl group, etc. are mentioned.

As the alicyclic hydrocarbon group, an alicyclic hydrocarbon group having 3 to 30 carbon atoms is preferable. The alicyclic hydrocarbon group may be saturated or unsaturated, and specific examples thereof include a cycloalkyl group, a cycloalkenyl group, a condensed polycyclic hydrocarbon group, a interchangeable hydrocarbon group, a spiro hydrocarbon group, a cyclic terpene hydrocarbon group, and the like. More specifically, cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, t-butylcyclohexyl group, cycloheptyl group, and cyclooctyl group; Cycloalkenyl groups such as 1-cyclohexenyl group; Condensed polycyclic hydrocarbon groups such as tricyclodecanyl group, decahydro-2-naphthyl group, and adamantyl group; Interchangeable hydrocarbon groups such as tricyclo[5.2.1.0 ^2,6 ]decane-8-yl group, pentacyclopentadecanyl group, isobonyl group, dicyclopentenyl group, and tricyclopentenyl group; Spiro hydrocarbon groups such as spiro[3,4]heptane and a monovalent group in which one hydrogen atom has been removed from spiro[3,4]octane; cyclic terpene hydrocarbon groups such as a monovalent group in which one hydrogen atom has been removed from p-mentane, thujane, and carane. It is more preferable that the cycloalkyl group and the cycloalkenyl group have 3 to 12 carbon atoms.

The aromatic hydrocarbon group is preferably 6 to 20 carbon atoms, and more preferably 6 to 10 carbon atoms. Specific examples of the aromatic hydrocarbon group include an aryl group. Here, in the present specification, the term "aryl group" refers to a monocyclic to tricyclic aromatic hydrocarbon group, and specifically, a phenyl group, a benzyl group, an o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, naphthyl group, An anthryl group, a phenanthryl group, an azulenyl group, and a 9-fluorenyl group.

The heterocyclic group for R ¹ to R ⁴ is not particularly limited as long as it is a monovalent heterocycle, but a 3- to 10-membered monocyclic or condensed bicyclic heterocyclic group is preferable, and specifically an oxiranyl group, an oxetanyl group, Pyrrolidinyl group, imidazolidinyl group, pyrazolidinyl group, morpholinyl group, theomorpholinyl group, piperidyl group, piperidino group, piperazinyl group, homopyrerazinyl group, 1,3-dioxolane Alicyclic heterocyclic groups such as -2-yl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolyl group, isoquinolyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, Imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, thiazolyl group, benzothiazolyl group, oxazolyl group, indolyl group, indazolyl group, benzoimidazolyl group, phthalimide group, thienyl group , Aromatic heterocyclic groups such as furyl group, pyranyl group, and furinyl group.

Among these, as R ¹ to R ^{4, a} hydrocarbon group is preferable. As the hydrocarbon group, an aliphatic hydrocarbon group and an aromatic hydrocarbon group are preferred, and R ¹ to R ⁴ are all aromatic hydrocarbon groups, and R ¹ and R ⁴ are aromatic hydrocarbon groups, and R ² and R ³ are more preferably an aliphatic hydrocarbon group. .

R ⁵ is a monovalent group is not particularly limited, and preferably a monovalent group (s) containing a hetero atom, for example, _{^{-CO 2 -, -CO 2 H,}} -CO 2 M, -CO 2 R 6, -SO 3 ^- , -SO ₃ H, -SO ₃ M, -SO ₃ R ⁷ , -SO ₂ NHR ⁸ , -SO ₂ NR ⁹ R ¹⁰ , -SO ₂ -ON=CR ¹¹ R ¹² , -SO ₂ NHNHR ¹³ ,- SO ₂ SR ¹⁴ and -SO ₂ NHSO ₂ R ¹⁵ . Here, R ⁶ to R ¹¹ and R ¹³ to R ¹⁵ each independently represent a substituted or unsubstituted hydrocarbon group, R ¹² represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group, and M represents a sodium atom or a potassium atom. .

The hydrocarbon group for R ⁶ to R ¹¹ and R ¹³ to R ¹⁴ is preferably an aliphatic hydrocarbon group and an aromatic hydrocarbon group, more preferably an alkyl group having 1 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms. The number of carbon atoms in the alkyl group is preferably 1 to 24, more preferably 1 to 18. The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 10.

As R ^{12, an} aliphatic hydrocarbon group is preferable, an alkyl group having 1 to 24 carbon atoms is more preferable, and an alkyl group having 1 to 12 carbon atoms is still more preferable.

As R ^{15, an} aliphatic hydrocarbon group and an aromatic hydrocarbon group are preferable, and an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 10 carbon atoms are more preferable.

Specific examples of these hydrocarbon groups include those similar to those described above.

The hydrocarbon group for R ¹ to R ⁴ and R ⁶ to R ¹⁵ and the heterocyclic group for R ¹ to R ⁴ may further have a substituent within a range not departing from the gist of the present invention. The position and number of substituents are arbitrary, and when two or more substituents are present, the substituents may be the same or different. Examples of such substituents include halogen atoms, hydroxyl groups, cyano groups, formyl groups, carboxyl groups, nitro groups, amino groups, mercapto groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, N-substituted amino groups, amide groups, and alkylcarbonyl groups. , An alkyloxycarbonyl group, an alkylsulfonyl group, an alkylsulfamoyl group, a trialkylsilyl group, an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a heterocyclic group. These substituents may further have a substituent.

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

Examples of the alkoxy group include C _1-12 alkoxy groups such as methoxy group, ethoxy group, propoxy group, butoxy group, hexyloxy group, 2-ethylhexyloxy group, octyloxy group, dodecyloxy group, and t-dodecyloxy group. have. As an aryloxy group, a phenoxy group, a benzyloxy group, etc. are mentioned.

As the alkylthio group, methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, pentylthio group, isopentylthio group, neopentylthio group, cyclopentylthio group, hexylthio group Silthio group, cyclohexylthio group, heptylthio group, cycloheptylthio group, octylthio group, 2-ethylhexylthio group, cyclooctylthio group, nonylthio group, decanylthio group, tricyclodecanylthio group, methoxypropyl Thio group, ethoxypropylthio group, hexyloxypropylthio group, 2-ethylhexyloxypropylthio group, methoxyhexylthio group, undecylthio group, dodecylthio group, tetradecylthio group, t-dodecylthio group, hexa C _1-20 alkylthio groups, such as a decylthio group and an octadecylthio group, are mentioned. As an arylthio group, a phenylthio group etc. are mentioned.

Examples of the substituent in the N-substituted amino group include a C _1-6 alkyl group and a C _6-10 aryl group, and specific examples include those similar to those described above.

Examples of the alkylcarbonyl group include a C _1-6 alkylcarbonyl group such as a methylcarbonyl group, an ethylcarbonyl group, a propylcarbonyl group, and a butylcarbonyl group.

Examples of the alkyloxycarbonyl group include C such as methyloxycarbonyl group, ethyloxycarbonyl group, propyloxycarbonyl group, butyloxycarbonyl group, hexyloxycarbonyl group, cyclohexyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, dodecylcarbonyl group, and octadecylcarbonyl group. _1-20 alkyloxycarbonyl groups are mentioned.

Examples of the alkylsulfonyl group include methylsulfonyl group, ethylsulfonyl group, hexylsulfonyl group, decanylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, tetradecylsulfonyl group, t-dodecylsulfonyl group, hexadecylsulfo C _1-20 alkylsulfonyl groups, such as a nil group and an octadecylsulfonyl group, are mentioned.

As the alkylsulfamoyl group, methylsulfamoyl group, ethylsulfamoyl group, dimethylsulfamoyl group, propylsulfamoyl group, isopropylsulfamoyl group, butylsulfamoyl group, hexylsulfamoyl group, octylsulfamoyl group, 2-ethylhex C _1-20 alkyl sulfamoyl groups, such as a silsulfamoyl group, an undecylsulfamoyl group, a dodecylsulfamoyl group, and 1-heptyl octylsulfamoyl group, are mentioned.

Examples of the trialkylsilyl group include tri C _1-6 alkylsilyl groups such as trimethylsilyl groups.

Specific examples of the aliphatic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group include those similar to those described above.

m is an integer of 0 to 5, but 0 to 3 are preferable, and 1 or 2 is more preferable.

In addition, at least one of R ¹ to R ⁴ in formula (1) is required to be a group selected from the following requirements (i) to (v).

(I) a substituted or unsubstituted unsaturated aliphatic hydrocarbon group, or a substituted or unsubstituted unsaturated alicyclic hydrocarbon group. However, the unsaturated aliphatic hydrocarbon group may have a linking group selected from -CO-, -COO- and -CONH- between C-C bonds.

(Ii) An alicyclic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group, or an aromatic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group or an unsaturated alicyclic hydrocarbon group.

(Iii) A substituted or unsubstituted heterocyclic group, or a hydrocarbon group substituted with a heterocyclic group.

(Iv) It is a hydrocarbon group substituted with at least 1 type selected from the substituent group α.

(V) A substituted or unsubstituted aliphatic hydrocarbon group having 11 or more carbon atoms.

Examples of the unsaturated aliphatic hydrocarbon group in the requirements (i) and (ii) include those similar to those described above, but among them, an alkenyl group is preferable. 2 to 20 are preferable, as for the carbon number, 2 to 10 are more preferable, and 2 to 6 are particularly preferable.

Examples of the unsaturated alicyclic hydrocarbon group in the requirements (i) and (ii) include those similar to those described above, but among them, a cycloalkenyl group is preferable. As for the carbon number, 4-8 are preferable and 5 or 6 are more preferable.

Examples of the heterocyclic group in the requirement (iii) include those similar to those described above, but an alicyclic heterocyclic group is preferable. Further, as the hydrocarbon group in the requirement (iv), a saturated hydrocarbon group is preferable, and a saturated aliphatic hydrocarbon group is more preferable. The number of carbon atoms in the saturated aliphatic hydrocarbon group is preferably 1 to 20, more preferably 1 to 10, and particularly preferably 2 to 6.

As the substituent group α in the requirement (iv), -CN and -NO ₂ are more preferable. In addition, as the hydrocarbon group in the requirement (iv), an aliphatic hydrocarbon group and an aromatic hydrocarbon group are preferable. The number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 20, more preferably 1 to 10, and particularly preferably 2 to 6.

The aliphatic hydrocarbon group having 11 or more carbon atoms in the requirement (v) may be saturated or unsaturated. Specifically, among those similar to those described above, a saturated aliphatic hydrocarbon group having 11 or more carbon atoms and an unsaturated aliphatic hydrocarbon group are mentioned. The number of carbon atoms of the aliphatic hydrocarbon group is preferably 11 to 20, more preferably 11 to 16. As the substituent in the requirement (v), a halogen atom, a hydroxyl group, a cyano group, a formyl group, a carboxyl group, a nitro group, an amino group, a mercapto group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an N-substituted amino group , An alkylcarbonyl group, an alkyloxycarbonyl group, an alkylsulfonyl group, an alkylsulfamoyl group, a trialkylsilyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a heterocyclic group. Specific examples of these substituents include those similar to those described above.

Among the above requirements (i) to (v), at least one of R ¹ to R ⁴ is a substituted or unsubstituted unsaturated aliphatic hydrocarbon group, an aromatic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group, a hydrocarbon group substituted with a heterocyclic group, and a substituent group α An aliphatic hydrocarbon group or an aromatic hydrocarbon group substituted with at least one selected from, preferably a substituted or unsubstituted aliphatic hydrocarbon group having 11 or more carbon atoms, and an aromatic hydrocarbon substituted with a substituted or unsubstituted unsaturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group An aliphatic hydrocarbon group or an aromatic hydrocarbon group substituted with at least one selected from a group and a substituent group α is preferable.

As a structure represented by general formula (1), the following structures are mentioned, for example. Among them, structural formulas (a1), (a10), (a16), (a17), (a19), (a20), (a22), and (a39) to (a45) are preferable. However, R ^a represents a 2-ethylhexyl group.

When the structure represented by formula (1) is cationic, the compound having the structure represented by formula (1) has an anion so that it is electrically neutral. As this anion, a halogen ion, a boron anion, a phosphate anion, a carboxylic acid anion, a sulfate anion, an organic sulfonic acid anion, a nitrogen anion, a methide anion, etc. are mentioned, for example. More specifically, the anion described in Japanese Patent Publication No. 2007-503477 is mentioned, for example.

When the structure represented by formula (1) is anionic, the compound having the structure represented by formula (1) has a cation so that it is electrically neutral. As this cation, a metal cation, an onium cation, etc. are mentioned, for example. Examples of the metal cations include monovalent metal cations such as lithium ions, sodium ions, and potassium ions, and divalent metal cations such as magnesium ions and calcium ions. Examples of the onium cation include an ammonium cation and a phosphonium cation. Examples of the ammonium cation include tetramethylammonium, tetraethylammonium, monostearyltrimethylammonium, distearyldimethylammonium, tristearylmonomethylammonium, cetyltrimethylammonium, trioctylmethylammonium, dioctyldimethylammonium, Monolauryltrimethylammonium, dilauryldimethylammonium, trilaurylmethylammonium, triamylbenzylammonium, trihexylbenzylammonium, trioctylbenzylammonium, trilaurylbenzylammonium, benzyldimethylstearylammonium, benzyldimethyloctylammonium, di And alkyl (alkyl is C14 to C18) dimethyl ammonium. Examples of the phosphonium cation include tetraalkylphosphonium such as methyltrioctylphosphonium, octyltributylphosphonium, dodecyltributylphosphonium, hexadecyltributylphosphonium, dihexyldioctylphosphonium, and benzyltri Aryltrialkylphosphonium such as butylphosphonium, dialkyldiarylphosphonium such as dibutyldiphenylphosphonium, alkyltriphenylphosphonium such as butyltriphenylphosphonium, and tetraarylphosphonium such as benzyltriphenylphosphonium And the like.

Although this colorant can be produced by an appropriate method, for example, a method similar to Example 3 of JP 2010-254964 A and JP 2013-011869 A can be mentioned. . This colorant thus obtained is soluble in various organic solvents including ketones such as cyclohexanone, and has excellent heat resistance.

In the present invention, this colorant can be used alone or in combination of two or more.

The coloring composition of the present invention may further contain other coloring agents together with the present coloring agent as a coloring agent. The other colorants are not particularly limited, and colors and materials can be appropriately selected depending on the application.

As the other colorant, any of a pigment, a dye other than the present colorant, and a natural colorant can be used, but in the sense of obtaining a pixel having high luminance and color purity, organic pigments and organic dyes are preferable, and organic pigments are particularly preferable.

Examples of the organic pigment include compounds classified as pigments in the color index (C. I.; issued by The Society of Dyers and Colourists), that is, those with the following color index (C. I.) numbers.

C. I. Pigment Red 166, C. I. Pigment Red 177, C. I. Pigment Red 224, C. I. Pigment Red 242, C. I. Pigment Red 254, C. I. Pigment Red 264;

C. I. Pigment Green 7, C. I. Pigment Green 36, C. I. Pigment Green 58;

C. I. Pigment Blue 15:6, C. I. Pigment Blue 16, C. I. Pigment Blue 80;

CI Pigment Yellow 83, CI Pigment Yellow 129, CI Pigment Yellow 138, CI Pigment Yellow 139, CI Pigment Yellow 150, CI Pigment Yellow 179, CI Pigment Yellow 180, CI Pigment Yellow 185, CI Pigment Pigment yellow 211, CI pigment yellow 215;

C. I. Pigment Orange 38;

C. I. Pigment Violet 23.

Other Japanese Patent Application Publication No. 2001-081348, Japanese Patent Application Publication No. 2010-026334, Japanese Patent Application Publication No. 2010-237384, Japanese Patent Application Publication No. 2010-237569, Japanese Patent Application Publication No. 2011-006602 Lake pigments described in Japanese Unexamined Patent Application Publication No. 2011-145346 and the like can be mentioned.

Further, as the dye, triarylmethane dyes, anthraquinone dyes, azo dyes and the like are preferable. More specifically, International Publication No. 10/123071, Japanese Patent Application No. 2011-116803, Japanese Patent Application No. 2011-117995, Japanese Patent Application No. 2011-133844, Japanese Patent Application No. 2011-174987 The organic dyes described in the publications and the like are mentioned.

It is preferable to use the coloring composition of this invention for formation of a blue pixel. In this case, as the colorant (A), it is preferable to include at least one selected from the group consisting of a blue pigment, a blue dye, a violet pigment, and a violet dye as another colorant together with the present colorant. In this case, the content ratio of the present colorant is preferably 0.1 to 80% by mass, more preferably 1 to 80% by mass, still more preferably 5 to 60% by mass, and particularly preferably 10 to 40% by mass of the total colorant. Do.

In the present invention, other pigments to be mixed arbitrarily may be purified and used by a recrystallization method, a reprecipitation method, a solvent washing method, a sublimation method, a vacuum heating method, or a combination thereof. In addition, these pigments may be used by modifying the surface of their particles with a resin as necessary. Examples of the resin for modifying the surface of the pigment particles include vehicle resins disclosed in Japanese Patent Laid-Open No. 2001-108817 or various commercially available resins for dispersing pigments. As a resin coating method on the surface of carbon black, for example, the method described in Japanese Patent Laid-Open (Hei) 9-71733, Japanese Patent Laid-Open (Hei) 9-95625, Japanese Patent Laid-Open (Hei) 9-124969, etc. Can be adopted. In addition, the organic pigment may be used by micronizing the primary particles by so-called salt milling. As the method of salt milling, for example, a method disclosed in Japanese Patent Laid-Open No. 08-179111 can be adopted.

Further, in the present invention, a known dispersing agent and a dispersing aid may be further contained together with other colorants to be mixed arbitrarily. Known dispersants include, for example, urethane dispersants, polyethyleneimine dispersants, polyoxyethylene alkyl ether dispersants, polyoxyethylene alkylphenyl ether dispersants, polyethylene glycol diester dispersants, sorbitan fatty acid ester dispersants, polyester systems. Dispersing agents, acrylic dispersants, etc. are mentioned, and pigment derivatives etc. are mentioned as a dispersion aid.

Such dispersants can be obtained commercially, for example, as acrylic dispersants, Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116, BYK-LPN21324 (manufactured by BYK), etc. As such, Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 (manufactured by BYK), Solspur 76500 (manufactured by Lubrizol Corporation), etc. , Solsperse 24000 (manufactured by Lubrizol Co., Ltd.) as a polyethyleneimine-based dispersant, and Azisper PB821, Azisper PB822, Azisper PB880, Azisper PB881 (above Ajinomoto Fine Techno Co., Ltd.) Inc.) and the like, respectively.

Further, specific examples of the pigment derivative include copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivatives of quinophthalone.

In the present invention, other colorants may be used alone or in combination of two or more.

In the case of containing other colorants, the content ratio of the other colorants is preferably 99.9% by mass or less, more preferably 99% by mass or less, further 95% by mass or less, and particularly preferably 90% by mass or less based on the total content of the colorants. . The lower limit value is not particularly limited and may be 0.01% by mass or more.

(A) The content rate of the colorant is usually 5 to 70% by mass, preferably in the solid content of the coloring composition, in terms of forming a pixel having excellent color purity due to high heat resistance and luminance, or a black matrix having excellent light-shielding property, and a black spacer. It is 5 to 60 mass %, More preferably, it is 10 to 40 mass %. Here, the solid content is a component other than the solvent mentioned later.

-(B) binder resin-

Although it does not specifically limit as (B) binder resin in this invention, It is preferable that it is a resin which has acidic functional groups, such as a carboxyl group and a phenolic hydroxyl group. Among them, a polymer having a carboxyl group (hereinafter, also referred to as a ``carboxyl group-containing polymer'') is preferable, and for example, ethylene which can be copolymerized with an ethylenically unsaturated monomer having at least one carboxyl group (hereinafter also referred to as ``unsaturated monomer (b1)'') A copolymer of a sexually unsaturated monomer (hereinafter also referred to as "unsaturated monomer (b2)") is mentioned.

Examples of the unsaturated monomer (b1) include (meth)acrylic acid, maleic acid, maleic anhydride, succinic acid mono[2-(meth)acryloyloxyethyl], ω-carboxypolycaprolactone mono(meth)acrylate and p-vinylbenzoic acid.

These unsaturated monomers (b1) can be used alone or in combination of two or more.

In addition, as the unsaturated monomer (b2), for example

N-position substituted maleimide such as N-phenylmaleimide and N-cyclohexylmaleimide;

Aromatic vinyl compounds such as styrene, α-methylstyrene, p-hydroxystyrene, p-hydroxy-α-methylstyrene, p-vinylbenzyl glycidyl ether, and acenaphthylene;

Methyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, allyl (meth)acrylate, benzyl (meth)acrylate , Polyethylene glycol (polymerization degree 2 to 10) methyl ether (meth) acrylate, polypropylene glycol (polymerization degree 2 to 10) methyl ether (meth) acrylate, polyethylene glycol (polymerization degree 2 to 10) mono (meth) acrylate, poly Propylene glycol (polymerization degree 2 to 10) mono(meth)acrylate, cyclohexyl(meth)acrylate, isobornyl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl(meth) Acrylate, dicyclopentenyl (meth) acrylate, glycerol mono (meth) acrylate, 4-hydroxyphenyl (meth) acrylate, ethylene oxide-modified (meth) acrylate of paracumylphenol, glycidyl ( Meth)acrylate, 3,4-epoxycyclohexylmethyl(meth)acrylate, 3-[(meth)acryloyloxymethyl]oxetane, 3-[(meth)acryloyloxymethyl]-3-ethyl (Meth)acrylic acid esters such as oxetane;

Cyclohexyl vinyl ether, isobornyl vinyl ether, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl vinyl ether, pentacyclopentadecanyl vinyl ether, 3-(vinyloxymethyl)-3-ethyloxetane Vinyl ethers such as;

Macromonomers having a mono(meth)acryloyl group at the terminal of a polymer molecular chain such as polystyrene, polymethyl (meth)acrylate, poly-n-butyl (meth)acrylate, and polysiloxane, and the like.

These unsaturated monomers (b2) can be used alone or in combination of two or more.

In the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2), the copolymerization ratio of the unsaturated monomer (b1) in the copolymer is preferably 5 to 50% by mass, more preferably 10 to 40% by mass. By copolymerizing the unsaturated monomer (b1) in such a range, a colored composition excellent in alkali developability and storage stability can be obtained.

Specific examples of the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2) include, for example, Japanese Patent Application Laid-open (Hei) 7-140654, Japanese Patent Laid-Open (Hei) 8-259876, and Japanese Patent Laid-Open (Hei). )10-31308, Japanese Patent Laid-Open (Hei) 10-300922, Japanese Patent Laid-Open (Hei) 11-174224, Japanese Patent Laid-Open (Hei) 11-258415, Japanese Patent Laid-Open No. 2000-56118 Copolymers disclosed in Japanese Patent Application Laid-Open No. 2004-101728 and the like can be mentioned.

In the present invention, for example, Japanese Patent Laid-Open (HEI) 5-19467, Japanese Patent Laid-Open (Hei) 6-230212, Japanese Patent Laid-Open (Hei) 7-207211, Japanese Patent Laid-Open ( As disclosed in Hei) 9-325494, Japanese Patent Laid-Open No. 11-140144, Japanese Patent Laid-Open No. 2008-181095, etc., polymerizable unsaturated bonds such as (meth)acryloyl groups in the side chain A carboxyl group-containing polymer having a can also be used as the binder resin.

The binder resin in the present invention has a weight average molecular weight (Mw) in terms of polystyrene measured by gel permeation chromatography (hereinafter referred to as GPC) (elution solvent: tetrahydrofuran) is usually 1,000 to 100,000, preferably 3,000 to 50,000. to be. By setting it as such an aspect, the film residual film rate, pattern shape, heat resistance, electrical property, and resolution of a film are further improved, and the generation|occurrence|production of dry foreign matter at the time of application|coating can be suppressed to a high level.

In addition, the ratio (Mw/Mn) of the weight average molecular weight (Mw) and number average molecular weight (Mn) of the binder resin in the present invention is preferably 1.0 to 5.0, more preferably 1.0 to 3.0. In addition, Mn here refers to the number average molecular weight in terms of polystyrene measured by GPC (elution solvent: tetrahydrofuran).

Although the binder resin in the present invention can be produced by a known method, for example, Japanese Patent Laid-Open No. 2003-222717, Japanese Patent Laid-Open No. 2006-259680, International Publication No. 07/029871, etc. The structure, Mw, and Mw/Mn can also be controlled by the disclosed method.

In the present invention, the binder resin may be used alone or in combination of two or more.

In the present invention, the content of the binder resin is usually 10 to 1,000 parts by mass, preferably 20 to 500 parts by mass, and more preferably 50 to 150 parts by mass based on 100 parts by mass of the (A) colorant. By setting it as such an aspect, alkali developability, storage stability of a colored composition, and chromaticity characteristics can be further improved.

-(C) polymerizable compound-

In the present invention, the polymerizable compound refers to a compound having two or more polymerizable groups. As a polymerizable group, an ethylenic unsaturated group, an oxiranyl group, an oxetanyl group, an N-alkoxymethylamino group, etc. are mentioned, for example. In the present invention, the polymerizable compound is preferably a compound having two or more (meth)acryloyl groups or a compound having two or more N-alkoxymethylamino groups.

As specific examples of the compound having two or more (meth)acryloyl groups, polyfunctional (meth)acrylate obtained by reacting an aliphatic polyhydroxy compound with (meth)acrylic acid, caprolactone-modified polyfunctional (meth)acrylate, Alkylene oxide-modified polyfunctional (meth)acrylate, polyfunctional urethane (meth)acrylate obtained by reacting a polyfunctional isocyanate with a (meth)acrylate having a hydroxyl group, and a (meth)acrylate having a hydroxyl group and an acid anhydride The polyfunctional (meth)acrylate etc. which have a carboxyl group obtained by reaction are mentioned.

Here, examples of the aliphatic polyhydroxy compound include divalent aliphatic polyhydroxy compounds such as ethylene glycol, propylene glycol, polyethylene glycol, and polypropylene glycol; And trivalent or higher aliphatic polyhydroxy compounds such as glycerin, trimethylolpropane, pentaerythritol, and dipentaerythritol. Examples of the (meth)acrylate having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, trimethylolpropanedi (meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta (Meth)acrylate, glycerol dimethacrylate, etc. are mentioned. Examples of the polyfunctional isocyanate include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate. As the acid anhydride, for example, anhydrides of dibasic acids such as succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, hexahydrophthalic anhydride, pyromellitic anhydride, biphenyltetracarboxylic dianhydride And tetrabasic acid dianhydrides such as benzophenone tetracarboxylic dianhydride.

Further, examples of the caprolactone-modified polyfunctional (meth)acrylate include compounds described in paragraphs [0015] to [0018] of Japanese Patent Laid-Open No. 11-44955. The alkylene oxide-modified polyfunctional (meth)acrylate is selected from bisphenol A di(meth)acrylate modified by at least one selected from ethylene oxide and propylene oxide, ethylene oxide and propylene oxide. Isocyanuric acid tri(meth)acrylate modified by at least one type, trimethylolpropane tri(meth)acrylate modified by at least one selected from ethylene oxide and propylene oxide, ethylene oxide and propylene Pentaerythritol tetra(meth)acrylate modified with at least one selected from pentaerythritol tri(meth)acrylate, ethylene oxide and propylene oxide modified with at least one selected from oxides, ethylene Dipentaerythritol hexa modified by at least one selected from dipentaerythritol penta (meth) acrylate, ethylene oxide and propylene oxide modified by at least one selected from oxide and propylene oxide ( And meth)acrylate.

Further, examples of the compound having two or more N-alkoxymethylamino groups include compounds having a melamine structure, a benzoguanamine structure, and a urea structure. In addition, the melamine structure and the benzoguanamine structure refer to a chemical structure having one or more triazine rings or phenyl substituted triazine rings as a basic skeleton, and a concept including melamine, benzoguanamine or condensates thereof. Specific examples of the compound having two or more N-alkoxymethylamino groups include N,N,N',N',N",N"-hexa(alkoxymethyl)melamine, N,N,N',N'-tetra( Alkoxymethyl)benzoguanamine, N,N,N',N'-tetra (alkoxymethyl) glycoluril, etc. are mentioned.

Among these polymerizable compounds, polyfunctional (meth)acrylates obtained by reacting trivalent or higher aliphatic polyhydroxy compounds with (meth)acrylic acid, caprolactone-modified polyfunctional (meth)acrylates, and polyfunctional urethane (meth)acrylates , Polyfunctional (meth)acrylate having a carboxyl group, N,N,N',N',N",N"-hexa(alkoxymethyl)melamine, N,N,N',N'-tetra(alkoxymethyl) Benzoguanamine is preferred. Among the polyfunctional (meth)acrylates obtained by reacting trivalent or higher aliphatic polyhydroxy compounds with (meth)acrylic acid, trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, di. Among the polyfunctional (meth)acrylates having a carboxyl group, pentaerythritol hexaacrylate is a compound obtained by reacting pentaerythritol triacrylate and succinic anhydride, and dipentaerythritol pentaacrylate is obtained by reacting succinic anhydride with pentaerythritol triacrylate. The compound is particularly preferable in that the strength of the colored layer is high, the surface smoothness of the colored layer is excellent, and it is difficult to generate background contamination, film residue, etc. on the substrate and the light-shielding layer of the unexposed portion.

In the present invention, the (C) polymerizable compound can be used alone or in combination of two or more.

The content of the (C) polymerizable compound in the present invention is preferably 10 to 1,000 parts by mass, more preferably 20 to 700 parts by mass, still more preferably 30 to 500 parts by mass, and 50 parts by mass per 100 parts by mass of the (A) colorant. Particularly preferably from 150 parts by mass. By setting it as such an aspect, hardenability and alkali developability are further improved, and generation|occurrence|production of background contamination, film residue, etc. can be suppressed to a high level on the board|substrate or light-shielding layer of an unexposed part.

-Photopolymerization initiator-

A photoinitiator can be contained in the coloring composition of this invention. Thereby, radiation-sensitive property can be imparted to the colored composition. The photopolymerization initiator used in the present invention is a compound that generates an active species capable of initiating polymerization of the polymerizable compound by exposure to radiation such as visible light, ultraviolet rays, far ultraviolet rays, electron rays, and X-rays.

Examples of such a photoinitiator include thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, α-diketone compounds, polynuclear quinone compounds, diazo compounds, imide sulfonate compounds, and the like.

In the present invention, the photoinitiator can be used alone or in combination of two or more. As the photoinitiator, at least one selected from the group of thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, and O-acyloxime compounds is preferable.

Specific examples of thioxanthone compounds among the preferred photopolymerization initiators in the present invention include thioxanthone, 2-chloro thioxanthone, 2-methyl thioxanthone, 2-isopropyl thioxanthone, and 4-isopropyl thioxanthone. Santone, 2,4-dichloro thioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, etc. are mentioned.

Further, specific examples of the acetophenone compound include 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4 -Morpholinophenyl)butan-1-one, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one, and the like.

In addition, as a specific example of the biimidazole-based compound, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2' -Bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4,6-trichlorophenyl) -4,4',5,5'-tetraphenyl-1,2'-biimidazole, etc. are mentioned.

In addition, when a biimidazole-based compound is used as the photoinitiator, it is preferable to use a hydrogen donor in combination, since the sensitivity can be improved. The "hydrogen donor" as used herein means a compound capable of donating a hydrogen atom to a radical generated from a non-imidazole-based compound by exposure. Examples of the hydrogen donor include mercaptan-based hydrogen donors such as 2-mercaptobenzothiazole and 2-mercaptobenzooxazole, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(di And amine-based hydrogen donors such as ethylamino)benzophenone. In the present invention, the hydrogen donor may be used alone or in combination of two or more, but the sensitivity can be further improved by using a combination of one or more mercaptan-based hydrogen donors and one or more amine-based hydrogen donors. desirable.

In addition, specific examples of the triazine-based compound include 2,4,6-tris(trichloromethyl)-s-triazine, 2-methyl-4,6-bis(trichloromethyl)-s-triazine, 2-[ 2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(furan-2-yl)ethenyl]-4, 6-bis(trichloromethyl)-s-triazine, 2-[2-(4-diethylamino-2-methylphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxyphenyl)-4,6-bis( Trichloromethyl)-s-triazine, 2-(4-ethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-n-butoxyphenyl)-4 And triazine-based compounds having a halomethyl group such as ,6-bis(trichloromethyl)-s-triazine.

Further, as a specific example of the O-acyloxime compound, 1,2-octanedione, 1-[4-(phenylthio)phenyl]-,2-(O-benzoyloxime), ethanol, 1-[9-ethyl- 6-(2-methylbenzoyl)-9H-carbazol-3-yl]-,1-(O-acetyloxime), ethanone,1-[9-ethyl-6-(2-methyl-4-tetrahydro Furanylmethoxybenzoyl)-9H-carbazol-3-yl]-,1-(O-acetyloxime), ethanone,1-[9-ethyl-6-{2-methyl-4-(2,2- Dimethyl-1,3-dioxolanyl)methoxybenzoyl}-9H-carbazol-3-yl]-,1-(O-acetyloxime), and the like. As commercial products of O-acyloxime compounds, NCI-831, NCI-930 (manufactured by ADEKA Co., Ltd.), DFI-020, DFI-091 (manufactured by Daito Chemicals Co., Ltd.), etc. May be.

In the present invention, when a photopolymerization initiator other than a biimidazole-based compound such as an acetophenone-based compound is used, a sensitizer may be used in combination. Examples of such sensitizers include 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4-diethylaminoacetophenone, and 4-dimethylaminopropiophenone. , 4-dimethylaminobenzoic acid ethyl, 4-dimethylaminobenzoic acid 2-ethylhexyl, 2,5-bis(4-diethylaminobenzal)cyclohexanone, 7-diethylamino-3-(4-diethylaminobenzoyl ) Coumarin, 4-(diethylamino)chalcone, etc. are mentioned.

In the present invention, the content of the photopolymerization initiator is preferably 0.01 to 120 parts by mass, more preferably 1 to 100 parts by mass, more preferably 10 to 60 parts by mass based on 100 parts by mass of the (C) polymerizable compound. By setting it as such an aspect, curing property and film|film|coat characteristic can be further improved.

-menstruum-

The coloring composition of the present invention contains the components (A) to (C) and other components optionally added, but is usually prepared as a liquid composition by blending a solvent.

As the solvent, components (A) to (C) or other components constituting the colored composition are dispersed or dissolved, and as long as they do not react with these components and have suitable volatility, they can be appropriately selected and used.

Among these solvents, for example

Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n -Propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene Glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tri (Poly) alkylene glycol monoalkyl ethers such as propylene glycol monoethyl ether;

Alkyl lactate esters such as methyl lactate and ethyl lactate;

(Cyclo)alkyl alcohols, such as methanol, ethanol, propanol, butanol, isopropanol, isobutanol, t-butanol, octanol, 2-ethylhexanol, and cyclohexanol;

Keto alcohols such as diacetone alcohol;

Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether (Poly)alkylene glycol monoalkyl ether acetates such as acetate, 3-methoxybutyl acetate, and 3-methyl-3-methoxybutyl acetate;

Other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran;

Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone;

Diacetates such as propylene glycol diacetate, 1,3-butylene glycol diacetate, and 1,6-hexanediol diacetate;

Alkoxycarboxyl, such as 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-ethoxy methyl propionate, 3-ethoxy ethyl propionate, ethoxy ethyl acetate, and 3-methyl-3-methoxybutyl propionate Acid esters;

Ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate , N-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-oxobutanoate, and other esters;

Aromatic hydrocarbons such as toluene and xylene;

Amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, or lactams.

Among these solvents, from the viewpoints of solubility, pigment dispersibility, coating properties, etc., (poly) alkylene glycol monoalkyl ethers, lactic acid alkyl esters, (poly) alkylene glycol monoalkyl ether acetates, other ethers, ketones, Diacetates, alkoxycarboxylic acid esters, and other esters are preferable, and in particular, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether Acetate, 3-methoxybutyl acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, 1,3-butylene glycol diacetate, 1,6- Hexanediol diacetate, ethyl lactate, 3-methoxy ethyl propionate, 3-ethoxy methyl propionate, 3-ethoxy ethyl propionate, 3-methyl-3-methoxybutyl propionate, n-butyl acetate, i- acetate Butyl, n-amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, i-propyl butyrate, n-butyl butyrate, ethyl pyruvate, and the like are preferable.

In the present invention, the solvent may be used alone or in combination of two or more. When used in combination, at least (poly) alkylene glycol monoalkyl ethers, (poly) alkylene glycol monoalkyl ether acetates, (poly) alkylene glycol monoalkyl ether acetates and alkoxycarboxylic acid esters are mixed. It is preferable to use it.

The content of the solvent is not particularly limited, but the total concentration of each component excluding the solvent of the coloring composition is preferably 5 to 50% by mass, and more preferably 10 to 40% by mass. By setting it as such an aspect, it is possible to obtain a coloring agent dispersion having good dispersibility and stability, and a coloring composition having good coating properties and stability.

-additive-

The coloring composition of this invention may contain various additives as needed.

Examples of additives include fillers such as glass and alumina; High molecular compounds such as polyvinyl alcohol and poly(fluoroalkyl acrylate); Surfactants such as fluorine-based surfactants and silicone-based surfactants; Vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl) -3-Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclo Hexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc. Adhesion promoter; 2,2-thiobis(4-methyl-6-t-butylphenol), 2,6-di-t-butylphenol, pentaerythritol tetrakis[3-(3,5-di-t-butyl-4) -Hydroxyphenyl)propionate], 3,9-bis[2-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)-propionyloxy]-1,1-dimethylethyl] Oxidation of -2,4,8,10-tetraoxa-spiro[5.5]undecane, thiodiethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], etc. Inhibitors; Aggregation inhibitors such as sodium polyacrylate; Malonic acid, adipic acid, itaconic acid, citraconic acid, fumaric acid, mesaconic acid, 2-aminoethanol, 3-amino-1-propanol, 5-amino-1-pentanol, 3-amino-1,2-propane Residue improving agents such as diol, 2-amino-1,3-propanediol, and 4-amino-1,2-butanediol; Developability improving agents such as succinate mono[2-(meth)acryloyloxyethyl], phthalic acid mono[2-(meth)acryloyloxyethyl], and ω-carboxypolycaprolactone mono(meth)acrylate, etc. are mentioned. I can. In addition, in the present invention, it is not necessarily necessary to contain ultraviolet absorbers such as benzotriazole, benzophenone, benzoate, and cyanoacrylate.

The coloring composition of the present invention can be produced by an appropriate method, and examples of the production method include methods disclosed in Japanese Patent Laid-Open No. 2008-58642, Japanese Patent Laid-Open No. 2010-132874, and the like. have. In the case of using both a dye and a pigment as a colorant, as disclosed in Japanese Patent Laid-Open No. 2010-132874, after passing the dye solution through the first filter, a dye solution passing through the first filter is separately prepared. It is possible to adopt a method of mixing with one pigment dispersion or the like, and producing the obtained colored composition through a second filter. In addition, after dissolving a dye, components (B) to (C), and other components used as necessary in a solvent, and passing the obtained solution through a first filter, a solution that has passed through the first filter is separately prepared. It is also possible to adopt a method of mixing with one pigment dispersion and producing the obtained colored composition through a second filter. Further, after passing the dye solution through the first filter, the dye solution that has passed through the first filter, the components (B) to (C), and other components used as necessary are mixed and dissolved, and the obtained solution is A method of producing the obtained colored composition by passing through the second filter and mixing the solution passed through the second filter with a separately prepared pigment dispersion, and passing the obtained colored composition through a third filter can also be adopted.

coloring Cured film And its manufacturing method

The colored cured film of the present invention is formed by using the colored composition of the present invention, and specifically means each color pixel, a black matrix, a black spacer, and the like used in a color filter.

Hereinafter, a colored cured film used for a color filter and a method of forming the same will be described.

As a method of manufacturing a color filter, first, the following method can be mentioned. First, a light-shielding layer (black matrix) is formed on the surface of the substrate so as to partition portions for forming pixels as necessary. Subsequently, after applying the liquid composition of the radiation-sensitive coloring composition of the present invention in red, for example, on this substrate, pre-baking is performed to evaporate the solvent to form a coating film. Next, after exposing this coating film to light through a photomask, it is developed using an alkali developer to dissolve and remove the unexposed portion of the coating film. Thereafter, post-baking is performed to form a pixel array in which red pixel patterns (colored cured film) are arranged in a predetermined arrangement.

Next, using each of the green or blue radiation-sensitive coloring compositions, applying, pre-baking, exposure, development, and post-baking each radiation-sensitive coloring composition in the same manner as above, thereby forming a green pixel array and a blue pixel array. It is formed sequentially on the same substrate. Accordingly, a color filter in which pixel arrays of three primary colors of blue, green and red are disposed on a substrate is obtained. However, in the present invention, the order of forming the pixels of each color is not limited to the above.

In addition, the black matrix can be formed by forming a metal thin film such as chromium formed by sputtering or evaporation into a desired pattern using a photolithography method, but the above pixel is formed by using a radiation-sensitive coloring composition in which a black pigment is dispersed. It can also be formed in the same manner as in the case of formation of.

Examples of the substrate used when forming the color filter include glass, silicone, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide.

In addition, these substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum evaporation, or the like, if necessary.

When applying the radiation-sensitive coloring composition to the substrate, a suitable coating method such as spray method, roll coating method, rotation coating method (spin coating method), slit die coating method (slit coating method), bar coating method, etc. can be adopted. In particular, it is preferable to employ a spin coating method or a slit die coating method.

Pre-baking is usually performed by combining drying under reduced pressure and drying by heating. Drying under reduced pressure is usually performed until it reaches 50 to 200 Pa. In addition, the conditions for heat drying are usually about 1 to 10 minutes at 70 to 110°C.

The coating thickness is generally 0.6 to 8 µm, preferably 1.2 to 5 µm, as the film thickness after drying.

As a light source of radiation used to form at least one selected from pixels and black matrices, for example, xenon lamps, halogen lamps, tungsten lamps, high pressure mercury lamps, ultra high pressure mercury lamps, metal halide lamps, medium pressure mercury lamps, low pressure mercury lamps, etc. And laser light sources such as a lamp light source, an argon ion laser, a YAG laser, an XeCl excimer laser, and a nitrogen laser. An ultraviolet LED can also be used as an exposure light source. The wavelength is preferably radiation in the range of 190 to 450 nm.

In general, the exposure dose of radiation is preferably 10 to 10,000 J/m ² .

In addition, as the alkali developer, for example, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo-[5.4.0]-7-undecene, An aqueous solution, such as 1,5-diazabicyclo-[4.3.0]-5-nonene, is preferable.

An appropriate amount of a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like may be added to the alkali developer. In addition, after alkali development, it is usually washed with water.

As the developing treatment method, a shower developing method, a spray developing method, a dip (immersion) developing method, a puddle (liquid storage) developing method, or the like can be applied. Development conditions are preferably 5 to 300 seconds at room temperature.

Post-baking conditions are usually about 10 to 60 minutes at 180 to 280°C.

The film thickness of the pixel thus formed is usually 0.5 to 5 µm, preferably 1.0 to 3 µm.

In addition, as a second method of manufacturing a color filter, a method of obtaining pixels of each color is adopted by the inkjet method disclosed in Japanese Patent Laid-Open (HEI) 7-318723, Japanese Patent Laid-Open No. 2000-310706, and the like. can do. In this method, first, a partition wall serving as a light-shielding function is formed on the surface of the substrate. Next, after discharging the liquid composition of the thermosetting coloring composition of the present invention in blue color, for example, into the formed partition wall by an ink jet apparatus, prebaking is performed to evaporate the solvent. Subsequently, after exposing this coating film as necessary, it is hardened by post-baking, and a blue pixel pattern is formed.

Next, each green or red thermosetting coloring composition is used, and a green pixel pattern and a red pixel pattern are sequentially formed on the same substrate in the same manner as above. Accordingly, a color filter in which pixel patterns of three primary colors of blue, green and red are disposed on a substrate is obtained. However, in the present invention, the order of forming the pixels of each color is not limited to the above.

In addition, since the partition wall has a function of not only shielding light but also a function of preventing mixing of the thermosetting coloring composition of each color discharged into the partition, the film thickness is thicker compared to the black matrix used in the first method. Therefore, the partition wall is usually formed using a black radiation-sensitive composition.

The substrate used when forming the color filter, the light source of radiation, and the method and conditions of pre-baking or post-baking are the same as those of the first method described above. The film thickness of the pixel formed by the inkjet method in this way is about the same as the height of the partition wall.

After forming a protective film as necessary on the pixel pattern thus obtained, a transparent conductive film is formed by sputtering. After the transparent conductive film is formed, a spacer may be further formed to form a color filter. The spacer is usually formed using a radiation-sensitive composition, but can also be used as a light-shielding spacer (black spacer). In this case, a colored radiation-sensitive composition in which a black colorant is dispersed is used, but the colored composition of the present invention can be preferably used also for formation of such a black spacer.

The colored composition of the present invention can be preferably used in the formation of any colored cured film such as each color pixel, black matrix, and black spacer used in the color filter.

The color filter including the colored cured film of the present invention thus formed has very high luminance and coloring power, and is therefore very useful for a color liquid crystal display device, a color image tube device, a color sensor, an organic EL display device, an electronic paper, and the like. In addition, the display element described later may have at least one or more colored cured films formed by using the colored composition of the present invention.

Display element

The display element of the present invention is provided with the colored cured film of the present invention. As a display element, a color liquid crystal display element, an organic EL display element, electronic paper, etc. are mentioned.

The color liquid crystal display device provided with the colored cured film of the present invention may be a transmissive type or a reflective type, and may adopt an appropriate structure. For example, by forming a color filter on a separate substrate from the driving substrate on which the thin film transistor (TFT) is disposed, the driving substrate and the substrate on which the color filter are formed can adopt a structure in which the substrate for driving and the substrate on which the color filter is formed are opposed to each other via a liquid crystal layer. In addition, a substrate having a color filter formed on the surface of a driving substrate on which a thin film transistor (TFT) is disposed, and an ITO (tin-doped indium oxide) electrode or an IZO (a mixture of indium oxide and zinc oxide) electrode are formed. It is also possible to adopt a structure in which the substrate faces through the liquid crystal layer. The latter structure has the advantage that the aperture ratio can be remarkably improved, and a bright and highly precise liquid crystal display element is obtained. Further, in the case of adopting the latter structure, the black matrix or the black spacer may be formed on either the side of the substrate on which the color filter is formed and the side of the substrate on which the ITO electrode or IZO electrode is formed.

The color liquid crystal display device having the colored cured film of the present invention may include a backlight unit using a white LED as a light source in addition to a cold cathode fluorescent lamp (CCFL). As a white LED, for example, a red LED, a green LED, and a blue LED are combined to obtain white light by a mixture color, a blue LED, a red LED and a green phosphor are combined to obtain white light by a mixture color, and a blue LED, red White LED, blue LED, white LED, orange light-emitting phosphor, and green light-emitting phosphor are combined to produce white light by a mixture color of white LED, blue LED, and YAG-based phosphor. And white LEDs obtained by mixing white LEDs, ultraviolet LEDs, red light-emitting phosphors, and green light-emitting phosphors and blue light-emitting phosphors to obtain white light by mixing.

The color liquid crystal display device having the colored cured film of the present invention includes a TN (Twisted Nematic) type, a STN (Super Twisted Nematic) type, an IPS (In-Planes Switching) type, a VA (Vertical Alignment) type, and an OCB (Optically Compensated Birefringence) type. Appropriate liquid crystal modes such as mold can be applied.

In addition, the organic EL display device provided with the colored cured film of the present invention can have an appropriate structure, for example, a structure disclosed in Japanese Patent Laid-Open No. 11-307242.

Further, the electronic paper provided with the colored cured film of the present invention can have an appropriate structure, and for example, a structure disclosed in Japanese Patent Laid-Open No. 2007-41169 is mentioned.

<Example>

Hereinafter, the embodiment of the present invention will be described more specifically by way of examples. However, the present invention is not limited to the following examples.

<Synthesis of this colorant>

Synthesis Example 1

20 parts by mass of a compound represented by the following formula (1) and 200 parts by mass of N-dodecylaniline (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were mixed under light-shielding conditions, and the resulting solution was stirred at 110°C for 6 hours. After cooling the obtained reaction solution to room temperature, it was added to a mixed solution of 800 parts by mass of water and 50 parts by mass of 35% hydrochloric acid, followed by stirring at room temperature for 1 hour. The precipitated crystals were suction filtered, and the obtained residue was dried to obtain 24 parts by mass of the compound represented by the general formula (A-1). It was confirmed by MS spectrum that the obtained red solid was a compound represented by the following formula (A-1). The obtained compound is referred to as a coloring agent (A-1).

Comparative Synthesis Example 1

According to the description of Synthesis Example 1 of Japanese Patent Laid-Open No. 2010-254964, a mixture of compounds represented by the following formulas (a-1-1) to (a-1-5) was synthesized. The mixture of the obtained compound is used as the coloring agent (a-1).

Comparative Synthesis Example 2

According to the description of Synthesis Example 2 in Japanese Patent Laid-Open No. 2012-181505, a compound represented by the following formula (a-2) was synthesized. The obtained compound is referred to as the coloring agent (a-2).

<Preparation and evaluation of dye solution>

Manufacturing Example 1

5 parts by mass of the coloring agent (A-1) and 95 parts by mass of cyclohexanone as a solvent were mixed to prepare a dye solution (A-1).

Preparation Examples 2 to 7

Dye solutions (A-2) to (A) in the same manner as in Production Example 1, except that the colorant represented by the following formulas (A-2) to (A-14) was used instead of the colorant (A-1) in Production Example 1. -14) was prepared.

Preparation Examples 15 to 16

In Production Example 1, the dye solution (a-1) to the dye solution (a-2) was carried out in the same manner as in Production Example 1 except that the coloring agent (a-1) to the coloring agent (a-2) were used instead of the coloring agent (A-1). ) Was prepared.

<Preparation of pigment dispersion>

Manufacturing Example 17

15 parts by mass of CI Pigment Blue 15:6 as a coloring agent, 12.5 parts by mass of BYK-LPN21116 (manufactured by BYK) as a dispersant (40% by mass of solid content concentration), 72.5 parts by mass of propylene glycol monomethyl ether acetate as a solvent And treated with a bead mill to prepare a pigment dispersion (a-3).

<(B) Synthesis of binder resin>

Synthesis Example 2

100 parts by mass of propylene glycol monomethyl ether acetate was added to a flask equipped with a cooling tube and a stirrer, followed by nitrogen substitution. Heated to 80°C, and at the same temperature, 100 parts by mass of propylene glycol monomethyl ether acetate, 20 parts by mass of methacrylic acid, 10 parts by mass of styrene, 5 parts by mass of benzyl methacrylate, 15 parts by mass of 2-hydroxyethyl methacrylate , 23 parts by mass of 2-ethylhexyl methacrylate, 12 parts by mass of N-phenylmaleimide, 15 parts by mass of succinate mono (2-acryloyloxyethyl) and 2,2'-azobis (2,4-dimethylvale) A mixed solution of 6 parts by mass of ronnitrile) was added dropwise over 1 hour, and polymerization was performed for 2 hours while maintaining this temperature. Thereafter, the temperature of the reaction solution was raised to 100°C, and polymerization was performed for an additional hour to obtain a binder resin solution (solid content concentration of 33% by mass). The obtained binder resin had an Mw of 12,200 and a Mn of 6,500. Let this binder resin be "binder resin (B1)".

<Preparation and evaluation of colored composition>

Example 1

Pigment dispersion (a-3) 46.0 parts by mass, dye solution (A-1) 24.3 parts by mass, 24.6 parts by mass of the binder resin (B1) solution as a binder resin, M-402 (dipentaeryte) manufactured by Toa Kosei Co., Ltd. as a crosslinking agent Mixture of ritolhexaacrylate and dipentaerythritol pentaacrylate) 7.1 parts by mass, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one (Ciba· Specialty Chemicals, brand name IRGACURE369) 2.1 parts by mass, Megaface F-554 (manufactured by DIC Corporation) as a surfactant, 0.05 parts by mass, and ethyl lactate as a solvent to prepare a colored composition having a solid content concentration of 20% by mass. Was prepared.

After applying the obtained colored composition on a glass substrate using a spin coater, pre-baking was performed on a hot plate at 80°C for 10 minutes to form three coating films having different film thicknesses.

Subsequently, after cooling this substrate to room temperature, a high-pressure mercury lamp was used, and without a photomask interposed, radiation including each wavelength of 365 nm, 405 nm and 436 nm was exposed to the coating film at an exposure amount of 2,000 J/m ² . . In this way, a blue cured film for evaluation was formed on the substrate.

Contrast evaluation

Insert the substrate on which the cured film was formed with two deflecting plates, rotate the deflecting plate on the front side while irradiating with a fluorescent lamp (wavelength range 380 to 780 nm) from the rear side, and use a luminance meter LS-100 (manufactured by Minolta). The maximum and minimum values of the transmitted light intensity were measured. And the value obtained by dividing the maximum value by the minimum value for each cured film was taken as the contrast ratio. The contrast ratio at the chromaticity coordinate value y=0.080 was obtained from the measurement result. Table 1 shows the evaluation results. In addition, the higher the value, the better the contrast ratio.

Heat resistance evaluation

Using a color analyzer (MCPD2000 manufactured by Otsuka Denshi Co., Ltd.), the substrate on which the cured film was formed was measured with a C light source, a 2-degree field of view, and chromaticity coordinate values (x, y) and stimulation values (Y) in the CIE color system. I did.

Subsequently, after 1 hour post-baking in a 230°C clean oven, chromaticity coordinate values (x, y) and stimulation values (Y) were measured, and the color change before and after additional baking, that is, ΔE ^* _ab was evaluated. As a result, the case where ΔE ^* _ab was less than 3.0 was evaluated as "◎", the case of 3.0 or more and less than 5.0 was evaluated as "○", and the case of 5.0 or more was evaluated as "x". Table 1 shows the evaluation results.

Evaluation of voltage retention

A SiO ₂ film preventing elution of sodium ions was formed on the surface, and the obtained colored composition was spin-coated on a soda glass substrate on which an ITO (indium-tin oxide alloy) electrode was deposited in a predetermined shape, and then hot at 100°C. Pre-baking was performed on the plate for 1 minute to form a coating film having a thickness of 2.0 µm. Subsequently, the coating film was exposed at an exposure amount of 700 J/m ² without interposing a photomask. Thereafter, the substrate was developed by immersing the substrate in a developer containing a 0.04 mass% potassium hydroxide aqueous solution at 23° C. for 1 minute, washed with ultrapure water, air-dried, and post-baked at 230° C. for 30 minutes, and the coating film was cured. To form a permanent cured film. Subsequently, the substrate on which the permanent cured film was formed and the substrate on which only the ITO electrode was deposited in a predetermined shape were bonded to each other with a sealing agent in which 1.8 mm of glass beads were mixed, and then a liquid crystal manufactured by Melk (MLC6608) was injected to prepare a liquid crystal cell. Next, the liquid crystal cell was put in a constant temperature layer at 60°C, and the voltage retention of the liquid crystal cell was measured by a liquid crystal voltage retention measuring system (VHR-1A type, Toyo Technica). The applied voltage at this time was a square wave of 5.5 V, and the measurement frequency was set to 60 Hz. Here, the voltage retention is a value obtained by (the liquid crystal cell potential difference after 16.7 milliseconds/voltage immediately after application). If the voltage retention rate of the liquid crystal cell is 90% or less, it means that the liquid crystal cell cannot maintain the applied voltage at a predetermined level for a time of 16.7 milliseconds, and it is not possible to sufficiently align the liquid crystal, and there is a risk of causing "burning" such as an afterimage. have.

Examples 2 to 14 and Comparative Examples 1 to 2

In Example 1, a colored composition was prepared in the same manner as in Example 1, except that the types and amounts of the pigment dispersion and dye solutions were changed as shown in Table 1. And the obtained colored composition was evaluated in the same manner as in Example 1. Table 1 shows the evaluation results.

Claims (7)

(A) A coloring composition containing a compound having a structure represented by the following general formula (1), (B) a binder resin, and (C) a polymerizable compound.

[In Formula (1), m represents an integer of 0 to 5, and when m is an integer of 2 or more, a plurality of R ⁵ may be the same or different,
R ¹ to R ⁴ independently of each other represent a hydrogen atom, a substituted or unsubstituted hydrocarbon group, or a substituted or unsubstituted heterocyclic group, provided that the hydrocarbon group is from -CO-, -COO- and -CONH- between CC bonds May have a selected connector,
R ⁵ independently of each other represent a monovalent group,
Provided that at least one of R ¹ to R ⁴ is a group selected from the following requirements (i) and (ii):
(I) a substituted or unsubstituted unsaturated aliphatic hydrocarbon group, or a substituted or unsubstituted unsaturated alicyclic hydrocarbon group, provided that the unsaturated aliphatic hydrocarbon group is a linking group selected from -CO-, -COO- and -CONH- between CC bonds May have,
(Ii) An alicyclic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group, or an aromatic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group or an unsaturated alicyclic hydrocarbon group.] The coloring composition according to claim 1, wherein at least one of R ¹ to R ⁴ is a substituted or unsubstituted unsaturated aliphatic hydrocarbon group or an aromatic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group. According to claim 1 or 2, wherein, R ⁵ is _{^{-CO 2 -, -CO 2 H,}} -CO 2 M, -CO 2 R 6, -SO 3 -, -SO 3 H, -SO 3 M, - SO ₃ R ⁷ , -SO ₂ NHR ⁸ , -SO ₂ NR ⁹ R ¹⁰ , -SO ₂ -ON=CR ¹¹ R ¹² , -SO ₂ NHNHR ¹³ , -SO ₂ SR ¹⁴ or -SO ₂ NHSO ₂ R ¹⁵ and ,
R ⁶ to R ¹¹ and R ¹³ to R ¹⁵ are each independently a substituted or unsubstituted hydrocarbon group,
R ¹² is a hydrogen atom or a substituted or unsubstituted hydrocarbon group,
A colored composition in which M is a sodium atom or a potassium atom. The coloring composition according to claim 1 or 2, further comprising at least one selected from the group consisting of a blue pigment, a blue dye, a purple pigment, and a purple dye as a colorant. A colored cured film formed by using the colored composition of claim 1 or 2. A display element comprising the colored cured film of claim 5. A compound having a structure represented by the following formula (1).

[In Formula (1), m represents an integer of 0 to 5, and when m is an integer of 2 or more, a plurality of R ⁵ may be the same or different,
R ¹ to R ⁴ independently of each other represent a hydrogen atom, a substituted or unsubstituted hydrocarbon group, or a substituted or unsubstituted heterocyclic group, provided that the hydrocarbon group is from -CO-, -COO- and -CONH- between CC bonds May have a selected connector,
R ⁵ independently of each other represent a monovalent group,
Provided that at least one of R ¹ to R ⁴ is a group selected from the following requirements (i) and (ii):
(I) a substituted or unsubstituted unsaturated alicyclic hydrocarbon group,
(Ii) An alicyclic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group, or an aromatic hydrocarbon group substituted with an unsaturated aliphatic hydrocarbon group or an unsaturated alicyclic hydrocarbon group.]