CN108663903B

CN108663903B - Colored resin composition, color filter and display device

Info

Publication number: CN108663903B
Application number: CN201810261036.3A
Authority: CN
Inventors: 芦田徹; 铃木智也
Original assignee: Dongwoo Fine Chem Co Ltd
Current assignee: Dongwoo Fine Chem Co Ltd
Priority date: 2017-03-27
Filing date: 2018-03-27
Publication date: 2023-03-10
Anticipated expiration: 2038-03-27
Also published as: CN108663903A

Abstract

The invention provides a colored resin composition which can form a color filter and a display device with excellent contrast and light resistance. The colored resin composition according to the present invention comprises a colorant and a resin, and is characterized in that the colorant comprises: a salt of an anion derived from a methine dye having an acid group and a metal cation having a valence of 2 or more. Further, a colored resin composition according to the present invention comprises a colorant and a resin, wherein the colorant comprises: a salt derived from an anion of a cyanine compound having an acid group and a metal cation having a valence of 2 or more.

Description

Colored resin composition, color filter and display device

Technical Field

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

Background

Color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors are made of colored resin compositions. As such a colored resin composition, a composition containing a compound represented by formula (3) as a colorant is known (patent document 1).

Further, as a colorant for a colored resin composition, a compound represented by the formula (2-1) is also known.

Documents of the prior art

Patent document

Patent document 1: japanese laid-open patent publication No. 2009-235392

Disclosure of Invention

Problems to be solved by the invention

However, the color filters formed from the above-described colored resin compositions known so far may not sufficiently satisfy contrast and light resistance. Accordingly, the present invention provides a colored resin composition that can form a color filter excellent in contrast and light resistance.

Means for solving the problems

The present invention includes the following inventions.

[1] A colored resin composition comprising a colorant and a resin, the colorant comprising: a salt of an anion derived from a methine dye having an acid group and a metal cation having a valence of 2 or more.

[2] A colored resin composition comprising a colorant and a resin, the colorant comprising: a salt of an anion derived from a cyanine compound having an acid group and a metal cation having a valence of 2 or more.

[3] [1] the colored resin composition according to [1] or [2], wherein the salt is a compound represented by the formula (I).

[ in the formula (I),

ring T ¹ Is represented by having at least a structure containing-N (R) ^a1 )(R ^a2 ) An aromatic hydrocarbon ring having 6 to 20 carbon atoms or an aromatic heterocycle having a substituent.

Ring T ² Represents an optionally substituted ring containing N or N in the constituent atoms thereof ⁺ The nitrogen-containing aromatic heterocycle of (1).

L ¹ And L ² Each independently represents a C1-8 hydrocarbon group having a valence of 2 which may have a substituent.

k represents an integer of 0 to 4 inclusive.

M ⁿ⁺ Represents a metal cation of n valency.

n represents an integer of 2 to 5 inclusive.

r represents M ⁿ⁺ The number of (b) is selected so that the valence of the formula (I) is 0.

R ^a1 And R ^a2 Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms.]

[4][3]The colored resin composition, wherein the ring T is ² Represents an optionally substituted ring containing N in the constituent atoms thereof ⁺ R is 1.

[5] The colored resin composition according to any one of [1] to [4], further comprising a polymerizable compound and a polymerization initiator.

[6] A color filter comprising the colored resin composition according to any one of [1] to [5 ].

[7] A display device comprising the color filter of [6 ].

ADVANTAGEOUS EFFECTS OF INVENTION

According to the present invention, a colored resin composition capable of forming a color filter excellent in contrast and light resistance is provided.

Detailed Description

< colored resin composition >

The colored resin composition of the present invention comprises a colorant (a) and a resin (B), and as the colorant (a), comprises: a salt of an anion derived from a methine dye having an acid group and a metal cation having a valence of 2 or more.

The colored resin composition of the present invention preferably further contains a polymerizable compound (C) and a polymerization initiator (D).

The colored resin composition of the present invention may further comprise a polymerization initiation aid (D1), a solvent (E), and a leveling agent (F).

In the present specification, unless otherwise specified, the compounds exemplified as the respective components may be used alone or in combination of a plurality of them.

< colorant (A) >)

As the colorant (a), the colored resin composition of the present invention comprises: the salt of an anion derived from a methine dye having an acid group and a metal cation having a valence of 2 or more preferably comprises: a salt of an anion derived from a cyanine compound having an acid group and a metal cation having a valence of 2 or more.

The so-called acid group is specifically a substituent of an ionizable hydrogen ion. As the acid group, a-COOH group or a-SO group is preferable ₃ And (4) an H group. The methine dye (preferably a cyanine compound) preferably has 1 to 5, more preferably 1 to 3, and further preferably 1 or 2 of the acid groups.

Methine dyes are dyes having at least one methine group.

Cyanine compounds are dyes belonging to polymethine dyes, meaning in particular that at one or both ends of the methine or polymethine chain conjugated nitrogen atoms or C = N coloring compounds are attached, most preferably one nitrogen atom having a + charge. As for the structure of the cyanine compound, cyanine (Streptocyanines), hemicyanine (Hemicyanines) or Closed cyanine (Closed chain cyanines) may be used, and hemicyanine or Closed chain cyanine is preferable.

The methine dye having an acid group means a compound in which an arbitrary hydrogen atom in a molecule constituting the methine dye is substituted with an acid group.

The cyanine compound having an acid group refers to a compound in which an arbitrary hydrogen atom in the cyanine compound is substituted with an acid group.

In the case of methine dyes having an acid group (preferably cyanine compounds having an acid group), the hydrogen ions of the acid group ionize to form anions derived from the methine dyes having an acid group (preferably cyanine compounds having an acid group), which anions are capable of forming salts with metal cations having a valence of 2 or more. The salt preferably has a valence of 0, i.e., is electrically neutral. The metal cation having a valence of 2 or more is preferably represented by M ⁿ⁺ And (b) a metal cation having a valence of n (wherein n represents an integer of 2 to 5).

As a salt of an anion derived from the methine dye having an acid group and a metal cation having a valence of 2 or more, preferably a salt of an anion derived from a cyanine compound having an acid group and a metal cation having a valence of 2 or more, a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) is preferable.

[ in the formula (I),

L ¹ And L ² Each independently represents a C1-C8 (valence: 2) hydrocarbon group which may have a substituent.

k represents an integer of 0 to 4 inclusive.

M ⁿ⁺ Represents a metal cation of n valency.

n represents an integer of 2 to 5 inclusive.

As a loop T ¹ Aromatic hydrocarbon rings having 6 to 20 carbon atoms include aromatic monocyclic hydrocarbons such as benzene, toluene, xylene, mesitylene, cumene and isopropyltoluene; pentalene, indene, naphthalene, azulene, heptylene, biphenyl, asymmetric-indacene, symmetric-indacene, acenaphthene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, benzo [9,10]Phenanthrene, pyrene,

Fused polycyclic hydrocarbons such as tetracene, and the like. The number of carbon atoms of the aromatic hydrocarbon ring is preferably 6 to 16, more preferably 6 to 10.

By a ring T ¹ The aromatic hydrocarbon ring having 6 to 20 carbon atoms at least contains-N (R) ^a1 )(R ^a2 ) A substituent of the group.

R ^a1 And R ^a2 Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms. The aliphatic hydrocarbon group having 1 to 8 carbon atoms may be any of straight, branched and cyclic.

Examples of the linear or branched aliphatic hydrocarbon group include linear aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl; branched aliphatic hydrocarbon groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, and 2-ethylhexyl group. The aliphatic hydrocarbon group preferably has 1 to 6 carbon atoms, more preferably 1 to 5 carbon atoms, and still more preferably 1 to 4 carbon atoms.

The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. The number of carbon atoms of the cyclic aliphatic hydrocarbon group is preferably 3 to 8, more preferably 3 to 6.

By a ring T ¹ The aromatic hydrocarbon ring having 6 to 20 carbon atoms represented by (a) may further have a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, a bromine atom, or the like; a nitro group; a cyano group; a hydroxyl group; alkoxy groups having 1 to 6 carbon atoms such as methoxy and ethoxy; a sulfanyl group; alkylsulfanyl groups having 1 to 6 carbon atoms such as methylsulfanyl groups and ethylsulfanyl groups; a carboxyl group; a carbamoyl group; alkoxycarbonyl groups having 1 to 6 carbon atoms such as methoxycarbonyl and ethoxycarbonyl; a sulfo group; an aminosulfonyl group; an alkoxysulfonyl group having 1 to 6 carbon atoms such as a methoxysulfonyl group and an ethoxysulfonyl group.

By a ring T ¹ The aromatic heterocyclic ring represented by (a) contains at least 1 or more hetero atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom as a constituent of the ring, and the ring-forming atom has pi electrons. The aromatic heterocycle may be monocyclic or polycyclic. The aromatic heterocycle preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and still more preferably 3 to 15 carbon atoms. As a loop T ¹ Examples of the aromatic heterocyclic ring include thiophene, pyrrole, furan, thiazole, oxazole, imidazole and pyrazoleAromatic monocyclic heterocycles such as oxazole; fused polycyclic heterocycles such as indole, benzindole, benzofuran, benzothiazole, benzoxazole, benzimidazole, benzopyrazole, and carbazole; hydrides of the above aromatic monocyclic heterocyclic ring, the above condensed polycyclic heterocyclic ring and the like contain carbonyl groups in the ring, and pyridones, pyrazolones and the like also include aromatic heterocyclic rings. By a ring T ¹ The aromatic heterocyclic ring represented by (a) is more preferably a nitrogen-containing aromatic heterocyclic ring containing a nitrogen atom as a constituent of the ring, the nitrogen atom being > N-.

As a ring T ¹ The nitrogen-containing aromatic heterocycle in (1) includes those represented by the formula (T) ¹ -A), formula (T) ¹ -B) and formula (T) ¹ A ring represented by-C), etc.

[ formula (T) ¹ -A), formula (T) ¹ -B) and formula (T) ¹ In (C) of the reaction mixture of (a) and (b),

X ^1a represents-C (R) ^a3 )(R ^a4 )-、-N(R ^a5 ) -, -O-or-S-, preferably-C (R) ^a3 )(R ^a4 )-。

X ^1b is-N = C (R) ^a5 )-。

R ^a3 、R ^a4 And R ^a5 Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent.

Ring T ⁵ Represents an optionally substituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.

ia is 1 or 2.

ib is 0, 1 or 2, preferably 0.]

By a ring T ² Represented by containing N or N in the constituent atoms of the ring ⁺ The nitrogen-containing aromatic heterocyclic ring of (2) is a constituent element of a ring containing a nitrogen atom of-N < or > N ⁺ <, the ring forms a nitrogen-containing aromatic heterocycle having pi electrons as an atom. By a ring T ² Represented by containing N or N in the constituent atoms of the ring ⁺ More preferably, the nitrogen-containing aromatic heterocycle of (2) contains-N < or > C = N ⁺ < as a constituent element of the ring.As a ring T ² Examples of the nitrogen-containing aromatic heterocyclic ring include nitrogen-containing aromatic monocyclic heterocyclic rings such as pyrrole, oxazole, imidazole and pyrazole; nitrogen-containing condensed polycyclic heterocycles such as indole, benzindole, benzoxazole, benzimidazole, benzopyrazole, and carbazole; hydrogenated products of the above nitrogen-containing aromatic monocyclic heterocyclic ring, the above nitrogen-containing condensed polycyclic heterocyclic ring, and the like. Ring T ² Preferably represents an optionally substituted compound containing N in the constituent atoms of the ring ⁺ The nitrogen-containing aromatic heterocycle of (1).

As a ring T ² The nitrogen-containing aromatic heterocycle in (1) includes those represented by the formula (T) ² -A), formula (T) ² -B) and formula (T) ² A ring represented by-C), etc.

[ formula (T) ² -A), formula (T) ² -B) and formula (T) ² In (C) of the reaction mixture of (a) and (b),

X ^2a represents-C (R) ^a6 )(R ^a7 )-、-N(R ^a8 ) -, -O-or-S-, preferably-C (R) ^a6 )(R ^a7 )-。

X ^2b is-N = C (R) ^a8 )-。

R ^a6 、R ^a7 And R ^a8 Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms and which may have a substituent.

Ring T ⁶ Represents an optionally substituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.

ja is 0 or 1.

jb is 0, 1 or 2, preferably 0.]

From R ^a3 ～R ^a8 The aliphatic hydrocarbon group having 1 to 8 carbon atoms may be any of straight chain, branched chain and cyclic.

From R ^a3 ～R ^a8 The aliphatic hydrocarbon group having 1 to 8 carbon atoms is preferably a hydrogen atom or a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, more preferably a hydrogen atom or a linear alkyl group having 1 to 4 carbon atoms, and still more preferably a methyl group or an ethyl group.

As a loop T ⁵ And T ⁶ Aromatic hydrocarbon rings having 6 to 20 carbon atoms include aromatic monocyclic hydrocarbons such as benzene, toluene, xylene, mesitylene, cumene and isopropyltoluene; pentalene, indene, naphthalene, azulene, heptalene, biphenyl, asymmetric-indacene, symmetric-indacene, acenaphthene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, benzo [9,10]Phenanthrene, pyrene,

Ring T ⁵ And T ⁶ Each independently is preferably benzene, naphthalene, phenalene or anthracene, more preferably benzene or naphthalene.

Ring T ⁵ And T ⁶ May be the same or different.

By a ring T ¹ An aromatic heterocyclic ring represented by the formula ² Represented by containing N or N in the constituent atoms of the ring ⁺ And a nitrogen-containing aromatic heterocycle of ⁵ And T ⁶ The aromatic hydrocarbon ring having 6 to 20 carbon atoms may have a substituent. Examples of the substituent include an oxo group; halogen atoms such as fluorine atom, chlorine atom, iodine atom, and bromine atom; a nitro group; a cyano group; -N (R) ^a1 )(R ^a2 ) Radical (in the formula, R ^a1 And R ^a2 The same as above); a hydroxyl group; first of allAlkoxy groups having 1 to 6 carbon atoms such as an oxy group and an ethoxy group; a sulfanyl group; alkylsulfanyl groups having 1 to 6 carbon atoms such as methylsulfanyl groups and ethylsulfanyl groups; a carboxyl group; a carbamoyl group; alkoxycarbonyl groups having 1 to 6 carbon atoms such as methoxycarbonyl and ethoxycarbonyl; a sulfo group; an aminosulfonyl group; an alkoxysulfonyl group having 1 to 6 carbon atoms such as a methoxysulfonyl group and an ethoxysulfonyl group.

In the formula (I), ring T ¹ At the ring T ¹ A part in which 2 hydrogen atoms are removed from any hydrogen atom contained in (1) and L ¹ To carbon atoms, ring T ² At the ring T ² A part in which 2 hydrogen atoms are removed from any hydrogen atom contained in (1) and L ² And carbon atoms.

Ring T ¹ And T ² May be the same or different.

From L ¹ And L ² The 2-valent hydrocarbon group having 1 to 8 carbon atoms is a 2-valent group derived by removing 2 arbitrary hydrogen atoms from a hydrocarbon having 1 to 8 carbon atoms, and includes a 2-valent aliphatic hydrocarbon group having 1 to 8 carbon atoms or a 2-valent aromatic hydrocarbon group having 6 to 8 carbon atoms.

Examples of the aliphatic hydrocarbon group having a valence of 2 include a chain hydrocarbon group having a valence of 2 and having 1 to 8 carbon atoms and an alicyclic hydrocarbon group having a valence of 2 and having 3 to 8 carbon atoms.

Examples of the chain aliphatic hydrocarbon group having a valence of 2 include alkylene groups such as methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl and octane-1,8-diyl.

Examples of the alicyclic hydrocarbon group having a valence of 2 include cyclopropane-1,1-diyl, cyclopropane-1,2-diyl, cyclobutane-1,1-diyl, cyclobutane-1,2-diyl, cyclobutane-1,3-diyl, cyclopentane-1,1-diyl, cyclopentane-1,2-diyl, cyclopentane-1,3-diyl, cyclohexane-1,1-diyl, cyclohexane-1,2-diyl, cyclohexane-1,3-diyl, cyclohexane-1,4-diyl, and groups represented by the formulae (L-a 1) to (L-a 6).

The 2-valent aromatic hydrocarbon group having 6 to 8 carbon atoms is preferably a 2-valent aromatic monocyclic hydrocarbon group having 6 to 8 carbon atoms, and examples of the 2-valent aromatic monocyclic hydrocarbon group include o-phenylene, m-phenylene, p-phenylene, and groups represented by formulae (L-b 1) to (L-b 6).

From L ¹ And L ² The hydrocarbon group having a valence of 2 and having 1 to 8 carbon atoms represented by the formula (I) is preferably an aliphatic hydrocarbon group having a valence of 2 and having 1 to 8 carbon atoms or an aromatic hydrocarbon group having a valence of 2 and having 6 to 8 carbon atoms, more preferably a chain hydrocarbon group having a valence of 2 and having 1 to 8 carbon atoms or an aromatic monocyclic hydrocarbon group having a valence of 2 and having 6 to 8 carbon atoms, further preferably an alkylene group having 1 to 8 carbon atoms or an aromatic monocyclic hydrocarbon group having a valence of 2 and having 6 to 7 carbon atoms, and particularly preferably a linear alkylene group having 1 to 8 carbon atoms or an aromatic monocyclic hydrocarbon group having a valence of 2 and having 6 carbon atoms.

The number of carbon atoms of the 2-valent aliphatic hydrocarbon group is preferably 1 to 6, and more preferably 1 to 4.

L ¹ And L ² The 2-valent hydrocarbon group having 1 to 8 carbon atoms in (b) may have a substituent, and examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom; a nitro group; a cyano group; an amino group; a hydroxyl group; alkoxy groups having 1 to 6 carbon atoms such as methoxy group and ethoxy group; a sulfanyl group; alkylsulfanyl groups having 1 to 6 carbon atoms such as methylsulfanyl groups and ethylsulfanyl groups; a carboxyl group; a carbamoyl group; alkoxycarbonyl groups having 1 to 6 carbon atoms such as methoxycarbonyl and ethoxycarbonyl; a sulfo group; an aminosulfonyl group; an alkoxysulfonyl group having 1 to 6 carbon atoms such as a methoxysulfonyl group and an ethoxysulfonyl group.

The 2-valent hydrocarbon group more preferably has no substituent.

L ¹ And L ² Each independently of the others, preferably a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a group represented by the formulae (L-b 1) to (L-b 6), an o-phenylene group, an m-phenylene group or a p-phenylene group, more preferably a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, an o-phenylene group, an m-phenylene group or a p-phenylene group. Furthermore, L ¹ And L ² May be the same or different, but preferably both are the same.

k is preferably 3 or less, more preferably 2 or less. In the formula (I), the carbon-carbon double bonds represented by the arrows s and t may be in either the E configuration or the Z configuration. That is, the formula (I) is defined to include all geometric isomers resulting from the carbon-carbon double bonds shown by the arrows s and t, and the same applies to the formula (II), the formula (III-A) and the formula (III-B).

As by M ⁿ⁺ Examples of the n-valent metal ion include alkaline earth metal ions such as magnesium ion, calcium ion, strontium ion, and barium ion; transition metal ions such as titanium ions, zirconium ions, chromium ions, manganese ions, iron ions, cobalt ions, nickel ions, and copper ions; typical metal ions such as zinc ions, cadmium ions, aluminum ions, indium ions, tin ions, lead ions, bismuth ions, and the like.

n is preferably 4 or less, more preferably 3 or less, and still more preferably 2.

The valence of compound (I) is 0, i.e. it is a neutral compound, thus M ⁿ⁺ The number r of (a) is selected so that the valence of the compound (I) is 0. r is preferably 1 or 2, more preferably 1.

M ⁿ⁺ More preferably an alkaline earth metal ion or a typical metal ion, further preferably a magnesium ion, a barium ion or an aluminum ion, and still further preferably a barium ion or an aluminum ion.

The compound (I) is preferably a compound represented by the formula (II) (hereinafter sometimes referred to as compound (II)).

[ in the formula (II), L ¹ 、L ² 、k、r、M ⁿ⁺ And n is the same as described above.

Ring T ³ Represents a nitrogen-containing aromatic heterocycle which may have a substituent.

Ring T ⁴ Represents an optionally substituted ring containing N or N in the constituent atoms thereof ⁺ The nitrogen-containing aromatic heterocycle of (1).

L ³ Represents a single bond or-CO-.

L ⁴ Represents a double bond or-CO-.]

By a ring T ³ The nitrogen-containing aromatic heterocyclic ring is a nitrogen-containing aromatic heterocyclic ring containing a nitrogen atom as a constituent of the ring, the nitrogen atom being > N-, the ring-forming atom having pi electrons as a ring T ³ Preferably of the formula (T) ³ -A), formula (T) ³ -B), formula (T) ³ -C) or formula (T) ³ -D) a ring.

By a ring T ⁴ Represented by containing N or N in the constituent atoms of the ring ⁺ The nitrogen-containing aromatic heterocyclic ring of (A) is a constituent containing a nitrogen atom as a ring, the nitrogen atom being-N < or > N ⁺ <, a nitrogen-containing aromatic heterocyclic ring having pi electrons as a ring-forming atom, as the ring T ⁴ Preferably of the formula (T) ⁴ -A), formula (T) ⁴ -B), formula (T) ⁴ -C) or formula (T) ⁴ -D) a ring.

Ring T ³ And T ⁴ May be the same or different.

[ formula (T) ³ -A), formula (T) ³ -B), formula (T) ³ -C), formula (T) ³ -D), formula (T) ⁴ -A), formula (T) ⁴ -B), formula (T) ⁴ -C) and formula (T) ⁴ in-D), X ^1a 、X ^2a 、X ^1b 、X ^2b Ring T ⁵ Ring T ⁶ As described above.

* L means and L ¹ Or L ² C means a bond to a carbon atom.]

Ring T ¹ And ring T ³ More preferably represented by the formula (R) ³ -1) to formula (R) ³ -7), further preferably represented by the formula (R) ³ -1) to formula (R) ³ -3) formula (R) ³ -7) a ring. Ring T ² And ring T ⁴ More preferably represented by the formula (R) ⁴ -1) to formula (R) ⁴ -7), further preferably represented by the formula (R) ⁴ -1) to formula (R) ⁴ -3) formula (R) ⁴ -7) a ring.

The compound (I) and the compound (II) are more preferably a compound represented by the formula (III-A) (hereinafter sometimes referred to as the compound (III-A)) or a compound represented by the formula (III-B) (hereinafter sometimes referred to as the compound (III-B)).

[ in the formula (III-A), ring T ⁵ Ring T ⁶ 、L ¹ 、L ² 、k、r、M ⁿ⁺ And n is the same as described above.]

[ in the formula (III-B), L ¹ 、L ² 、k、r、M ⁿ⁺ And n is the same as described above.]

Examples of the compound (I) include compounds represented by the formulae (I-1) to (I-189) shown in tables 1 to 3. The compound (I) is preferably a compound represented by any one of the formulae (I-1) to (I-63) and (I-127) to (I-168), more preferably a compound represented by any one of the formulae (I-43) to (I-63), formula (I-127) to (I-133) and formula (I-148) to (I-154), and still more preferably a compound represented by any one of the formulae (I-43) to (I-54), formula (I-131) to (I-133) and formula (I-152) to (I-154).

[ TABLE 1]

[ TABLE 2]

[ TABLE 3]

In tables 1 to 3, ring T ¹ Is represented by the formula (R) ³ -a 1) to formula (R) ³ Ring represented by a 4), ring T ² Is represented by the formula (R) ⁴ A 1) to formula (R) ⁴ -a 4) ring. Formula (R) ³ A 1) to formula (R) ³ A 4) and formula (R) ⁴ A 1) to formula (R) ⁴ In-a 4), L and C are the same as described above.

In tables 1 to 3, L ¹ And L ² Represents a 2-valent hydrocarbon group represented by the formulae (L-1) to (L-7). In the formulae (L-1) to (L-7), n means a bonding end to a nitrogen atom, and s means a bonding end to a sulfur atom.

The compound represented by the formula (I) can be produced by reacting the compound represented by the formula (pt 3) with a halide (preferably chloride), hydroxide, acetate, phosphate, sulfate, silicate, cyanide, or the like containing an n-valent metal ion.

In addition, L ¹ And L ² Identical and ring T ¹ And ring T ² In each ring > N-CH < >

＞N ⁺ The same compound represented by the formula (pt 3) except that = C < can be obtained by allowing a compound represented by the formula (pt 1)The compound (b) is reacted with a compound represented by the formula (pt 2) under acidic or basic conditions. In this reaction, the amount of the compound represented by the formula (pt 1) used is preferably 1.5 to 2.5 moles with respect to 1 mole of the compound represented by the formula (pt 2).

[ in the formula (pt 2), R ^c Is a hydrogen atom, a nitro group or a halogen atom. k is the same as described above. In the formulae (pt 1), (pt 3) and (I), the ring T ¹ Ring T ² 、L ¹ 、L ² 、k、M ⁿ⁺ And n is the same as described above.]

The content of the compound (I) is preferably 0.1 to 150 parts by mass, more preferably 1 to 100 parts by mass, and still more preferably 5 to 80 parts by mass, based on 100 parts by mass of the resin (B).

The colored resin composition of the present invention may contain, as the colorant (a), a dye (A1) and a pigment (A2) in addition to the compound (I).

The dye (A1) is not particularly limited, and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of The dye include compounds classified as compounds having a color tone in addition to pigments in The color index (published by The Society of Dyers and Colourists), and known dyes described in dyeing notes (color dyeing company). Further, depending on the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinonimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and the like can be cited. Among these, organic solvent-soluble dyes are preferred.

The pigment (A2) is not particularly limited, and known pigments can be used, and examples thereof include pigments classified as pigments in The Society of Dyers and Colourists publication.

Examples of the pigment include yellow pigments such as c.i. pigment yellow 1,3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, and 214;

orange pigments such as c.i. pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;

red pigments such as c.i. pigment red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265;

c.i. pigment blue 15, 15: 3. 15: 4. 15: 6. 60, and the like cyan pigments; violet pigments such as c.i. pigment violet 1, 19, 23, 29, 32, 36, and 38;

green pigments such as c.i. pigment green 7, 36, 58;

c.i. brown pigments such as pigment brown 23, 25;

and black pigments such as c.i. pigment black 1 and 7.

The content of the colorant (a) is preferably 0.1 to 70% by mass, more preferably 0.5 to 60% by mass, and still more preferably 1 to 50% by mass, based on the total amount of solid components.

The content of the compound (I) in the total amount of the colorant (a) is preferably 50% by mass or more, more preferably 80% by mass or more, and still more preferably 90% by mass or more.

Here, the "total amount of solid components" in the present specification refers to an amount obtained by removing the content of the solvent from the total amount of the colored resin composition. The total amount of the solid components and the contents of the respective components relative thereto can be measured by a known analytical means such as liquid chromatography or gas chromatography.

< resin (B) >

The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably a resin having a structural unit derived from at least 1 type (a) (hereinafter, sometimes referred to as "(a)") selected from unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides. The resin (B) further preferably has a structural unit selected from at least one of the following structural units: a structural unit derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, a structural unit derived from a monomer (c) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)") copolymerizable with (a), and a structural unit having an ethylenically unsaturated bond in a side chain.

Specific examples of (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and mono [2- (meth) acryloyloxyethyl ] succinate, and acrylic acid, methacrylic acid, and maleic anhydride are preferable.

(b) Preferred are monomers having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least 1 selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and a (meth) acryloyloxy group.

In the present specification, "(meth) acrylic acid" means at least 1 selected from acrylic acid and methacrylic acid. The expressions "(meth) acryloyl group" and "(meth) acrylate" and the like also have the same meaning.

Examples of (b) include glycidyl (meth) acrylate, vinylbenzyl glycidyl ether, 3,4-epoxy tricyclo [5.2.1.0 ] meth (acrylic acid) ^{_, 26} ]Decyl ester, 3-ethyl-3- (meth) acryloyloxymethyloxetane, tetrahydrofurfuryl (meth) acrylate, etc., preferably glycidyl (meth) acrylate, 3,4-epoxytricyclo [5.2.1.0 ] ^{_, 26} ]Decyl ester, 3-ethyl-3- (meth) acryloyloxymethyl oxetane.

Examples of (c) include methyl (meth) acrylate, butyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, and tricyclo [5.2.1.0 ] meth) acrylate ^{_, 26} ]Decane-8-yl ester, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene and the like, with styrene, vinyltoluene, 2-hydroxyethyl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide and the like being preferred.

The resin having a structural unit having an ethylenically unsaturated bond in a side chain can be produced by adding (b) to a copolymer of (a) and (c) or adding (a) to a copolymer of (b) and (c). The resin may be a resin obtained by reacting a copolymer of (b) and (c) with (a) and further with a carboxylic acid anhydride.

The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3000 to 100000, more preferably 5000 to 50000, and still more preferably 5000 to 30000.

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

The acid value of the resin (B) is preferably 20 to 170mg-KOH/g, more preferably 30 to 150mg-KOH/g, and still more preferably 40 to 135mg-KOH/g in terms of solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1g of the resin (B), and can be determined by titration with an aqueous potassium hydroxide solution, for example.

The content of the resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 55% by mass, based on the total amount of solid components.

The colored resin composition of the present invention may contain a polymerizable compound (C) and a polymerization initiator (D). Hereinafter, the colored resin composition containing the polymerizable compound (C) and the polymerization initiator (D) may be referred to as a "colored curable resin composition".

< polymerizable Compound (C) >)

The polymerizable compound (C) is a compound polymerizable by an active radical and/or an acid generated by the polymerization initiator (D), and examples thereof include a compound having a polymerizable ethylenically unsaturated bond, and a (meth) acrylate compound is preferable.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (meth) acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2900 or less, and more preferably 250 or more and 1500 or less.

When the polymerizable compound (C) is contained, the content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 55% by mass, based on the total amount of the solid content.

< polymerization initiator (D) >)

The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate an active radical, an acid, or the like by the action of light or heat and initiate polymerization, and a known polymerization initiator can be used. Examples of the polymerization initiator generating an active radical include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propane-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-one, 1-hydroxycyclohexylphenylketone, 2,4-bis (trichloromethyl) -6-piperonyl-32 zxft 3732-triazine, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 4325 ' -bis (2-chlorophenyl) -4,4', 3926 ' -tetraphenylimidazole, and the like.

When the polymerization initiator (D) is contained, the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be high and the exposure time tends to be short, so that the productivity of the color filter tends to be improved.

The colored resin composition of the present invention may contain a polymerization initiation aid (D1).

< polymerization initiation assistant (D1) >)

The polymerization initiation aid (D1) is a compound or a sensitizer used for promoting polymerization of a polymerizable compound whose polymerization is initiated by a polymerization initiator. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D).

Examples of the polymerization initiator aid (D1) include 4,4 '-bis (dimethylamino) benzophenone (Nami' er's ketone), 4,4' -bis (diethylamino) benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, and N-phenylglycine.

When the polymerization initiation aid (D1) is used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the amount of the polymerization initiating assistant (D1) is within this range, a colored pattern can be further formed with high sensitivity, and the productivity of the color filter tends to be improved.

The colored resin composition of the present invention may contain a solvent (E).

< solvent (E) >

The solvent (E) is not particularly limited, and a solvent generally used in this field can be used. <xnotran> ( -COO- -O- ), ( -O- -COO- ), ( -COO- -O- ), ( -CO- -COO- ), ( OH -O-, -CO- -COO- ), , , . </xnotran>

Examples of the solvent include

Ester solvents (solvents containing-COO-and not containing-O-in the molecule) such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate, and γ -butyrolactone;

ether solvents (solvents containing-O-in the molecule and not containing-COO-) such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and the like;

ether ester solvents (containing-COO-and-O-in the molecule) such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and diethylene glycol monoethyl ether acetate;

ketone solvents (solvents containing-CO-and not-COO-in the molecule) such as 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone, and cyclohexanone;

alcohol solvents (containing OH in the molecule and not containing-O-) -CO-and-COO-);

amide solvents such as N, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone, and the like.

As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and ethyl 3-ethoxypropionate are more preferable.

When the solvent (E) is contained, the content of the solvent (E) is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, based on the total amount of the colored resin composition of the present invention. In other words, the total amount of solid components in the colored resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. When the content of the solvent (E) is within the above range, the flatness at the time of coating becomes good, and the color density is not insufficient at the time of forming a color filter, so that the display characteristics tend to become good.

The colored resin composition of the present invention may contain a leveling agent (F).

< leveling agent (F) >

Examples of the leveling agent (F) include a silicone surfactant, a fluorine surfactant, and a silicone surfactant having a fluorine atom. They may have a polymerizable group in a side chain.

Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, TORAY SILICONE DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toriliko-Dow Corning Co., ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by shin-Etsu chemical industry Co., ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, and TSF4460 (manufactured by Mitsugao Hi-Tech materials, japan, ltd.) may be mentioned.

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, examples thereof include FLUORAD (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., ltd.), MEGAFAC (registered trademark) F142D, F, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Co., ltd.), EFTOP (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Synthesis instruments Co., ltd.), SURFON (registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Nitro (Co., ltd.), and E5844 (manufactured by Otsukui Fine chemistry research Co., ltd.).

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

When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, based on the total amount of the colored resin composition. Note that the content does not include the content of the pigment dispersant. If the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

< other ingredients >

The colored resin composition of the present invention may contain, if necessary, additives known in the art, such as a filler, another polymer compound, an adhesion promoter, an antioxidant, a light stabilizer, and a chain transfer agent.

< method for producing colored resin composition >

The colored resin composition of the present invention can be prepared by mixing the colorant (a) and the resin (B), and if necessary, the polymerizable compound (C), the polymerization initiator (D), the polymerization initiation aid (D1), the solvent (E), the leveling agent (F), and other components.

< method for manufacturing color filter >

Examples of the method for producing a colored pattern from the colored resin composition of the present invention include photolithography, ink jet printing, and printing. Among them, photolithography is preferable.

By including the compound (I) as a colorant in the colored resin composition, a color filter particularly excellent in contrast and light resistance can be produced. The color filter can be used as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state imaging element.

Examples

The colored resin composition of the present invention will be described in more detail below with reference to examples. In the examples, "%" and "part(s)" are% by mass and part(s) by mass unless otherwise specified.

Example 1

9.2 parts of the compound represented by the formula (1-1) and 5.5 parts of the compound represented by the formula (1-2) were added to 18 parts of acetic anhydride, and mixed at room temperature. Then, 8 parts of triethylamine was added thereto, and the mixture was stirred at 40 ℃ for 5 hours. After the reaction, 100 parts of ethyl acetate was added to precipitate crystals, which were then filtered. The residue was washed 3 times with 80 parts of ethyl acetate, and the crystals were dried under reduced pressure at 60 ℃ to give 8.4 parts of a compound represented by the formula (1-3).

A liquid (aqueous solution 1) in which the compound represented by formula (1-3) was dissolved was prepared by adding 11 parts of the compound represented by formula (1-3) to 100 parts of water. Further, a liquid (aqueous solution 2) in which 19.5 parts of barium chloride dihydrate was dissolved in 80 parts of water was prepared, and the aqueous solution 2 was dropped into the aqueous solution 1 at 40 ℃ over 2 hours, followed by stirring for 4 hours. After cooling, filtration was carried out, washing was carried out 2 times with 100 parts of ion-exchanged water, and the crystals were dried under reduced pressure at 100 ℃ to obtain 18 parts of a compound represented by the formula (I-52).

Example 2

A liquid (aqueous solution 1) in which the compound represented by formula (2-1) was dissolved was prepared by adding 5.2 parts of the compound represented by formula (2-1) to 100 parts of water. Further, a liquid (aqueous solution 2) in which 7.1 parts of aluminum hydroxide was dissolved in 80 parts of water was prepared, and the aqueous solution 2 was dropped into the aqueous solution 1 at 40 ℃ over 2 hours and then stirred for 4 hours. After cooling, filtration was carried out, and the crystals were washed 2 times with 100 parts of ion-exchanged water, and dried under reduced pressure at 100 ℃ to obtain 1.8 parts of a compound represented by the formula (I-152).

Example 3

A liquid (aqueous solution 1) in which the compound represented by formula (2-1) was dissolved was prepared by adding 5.2 parts of the compound represented by formula (2-1) to 100 parts of water. Further, a liquid (aqueous solution 2) in which 12.2 parts of barium chloride dihydrate was dissolved in 80 parts of water was prepared, and the aqueous solution 2 was dropped into the aqueous solution 1 at 40 ℃ for 2 hours and then stirred for 4 hours. After cooling, filtration was carried out, and the crystals were washed 2 times with 100 parts of ion-exchanged water, and dried under reduced pressure at 100 ℃ to obtain 5.9 parts of a compound represented by the formula (I-131).

[ Synthesis example 1]

In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, an appropriate amount of nitrogen was introduced to make a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was charged, and the mixture was heated to 80 ℃ with stirring. Next, 38 parts of acrylic acid, 3,4-epoxy tricyclo [5.2.1.0 ] was added dropwise to the flask using a dropping pump over about 5 hours ^{_, 26} ]Decan-8-yl ester and acrylic acid 3,4-epoxytricyclo [5.2.1.0 ^2,6 ]A solution of 289 parts of a mixture of decane-9-yl esters (trade name "E-DCPA", manufactured by Dailuo Co., ltd.) dissolved in 125 parts of propylene glycol monomethyl ether acetate. On the other hand, 33 parts of a polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise to the flask using an additional dropping pump over about 6 hours. After completion of the dropwise addition, the mixture was held at the same temperature for 4 hours and then cooled to room temperature, whereby a copolymer (resin (B-2)) having a solid content of 35.1% was obtained. The weight-average molecular weight Mw of the obtained copolymer was 9200, the degree of dispersion was 2.08, and the acid value in terms of solid content was 77mg-KOH/g. The resin (B-2) has the following structural unit.

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by Gel Permeation Chromatography (GPC) under the following conditions.

The device comprises the following steps: HLC-8120GPC (manufactured by Tosoh corporation)

Column: TSK-GELG2000HXL

Column temperature: 40 deg.C

Solvent: THF (tetrahydrofuran)

Flow rate: 1.0mL/min

Concentration of solid content in liquid to be detected: 0.001 to 0.01 mass%

Injection amount: 50 μ L

A detector: RI (Ri)

Calibration standard substance: TSK STANDARD POLYSTYRENE

F-40、F-4、F-288、A-2500、A-500

(manufactured by Tosoh corporation)

The ratio (Mw/Mn) of the weight average molecular weight to the number average molecular weight in terms of polystyrene obtained above was defined as the degree of dispersion.

Example 4

[ preparation of Dispersion (P-1) ]

After 10 parts of the compound represented by the formula (I-52), 4 parts of a solid content of a dispersant BYK-LP N6919 (manufactured by BYK), 5 parts (in terms of solid content) of a resin (B-2) solution (35.0%) and 181 parts of propylene glycol monomethyl ether acetate were weighed, 300 parts of 0.4 μm zirconia beads were placed, and the resulting mixture was shaken for 6 hours using a paint conditioner (manufactured by LAU) to remove the zirconia beads by filtration, thereby preparing a dispersion (P-1).

[ preparation of colored resin composition ]

The respective components were mixed so as to have the compositions shown in table 4, to obtain colored resin compositions.

Comparative example 1

A colored resin composition was obtained in the same manner as in example 4, except that the dispersion liquid (P-1) was changed to the colorant (A-1).

[ TABLE 4]

In table 4, each component represents the following compound.

Colorant (A-1): a compound represented by the formula (3)

Resin (B-2): resin (B-2) (conversion of solid content)

Polymerizable compound (C-1): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Chemicals, inc.)

Polymerization initiator (D-1): n-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01, BASF corporation)

Solvent (E-1): propylene glycol monomethyl ether acetate

Example 5

[ preparation of Dispersion (P-2) ]

A dispersion (P-2) was prepared in the same manner as in example 4, except that the compound represented by the formula (I-52) in example 4 was changed to the compound represented by the formula (I-152).

[ preparation of colored resin composition ]

The respective components were mixed so as to have the compositions shown in table 5, to obtain colored resin compositions.

Example 6

[ preparation of Dispersion (P-3) ]

A dispersion (P-3) was prepared in the same manner as in example 4, except that the compound represented by the formula (I-52) was changed to the compound represented by the formula (I-131) in example 4.

[ preparation of colored resin composition ]

Comparative example 2

A colored resin composition was obtained in the same manner as in example 5, except that the dispersion liquid (P-1) was changed to the colorant (2-1).

[ TABLE 5]

In table 5, each component represents the following compound.

Colorant (2-1): a compound represented by the formula (2-1)

Resin (B-2): resin (B-2) (conversion of solid content)

Solvent (E-1): propylene glycol monomethyl ether acetate

< making of colored patterns >

The colored resin composition was applied to a 5cm square glass substrate (Eagle 2000; manufactured by Corning corporation) by spin coating, and then prebaked at 100 ℃ for 3 minutes to obtain a colored composition layer. After cooling, the substrate on which the colored composition layer was formed and a photomask made of quartz glass were spaced at 100 μm, and the resultant was exposed to an exposure apparatus (TME-150 RSK; manufactured by Topukang Co., ltd.) in an air atmosphere150mJ/cm for ² The exposure amount (365 nm basis) of (A) was irradiated with light. As the photomask, a photomask in which a 100 μm line and gap pattern was formed was used. The colored composition layer after the light irradiation was subjected to immersion development at 24 ℃ for 60 seconds in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide, washed with water, and then baked in an oven at 200 ℃ for 20 minutes to obtain a colored pattern.

< evaluation of contrast >

The contrast was measured for the colored patterns obtained in example 4 and comparative example 1 using a contrast meter (CT-1: manufactured by Kyowa Kagaku K.K., color difference meter BM-5A: manufactured by Topukang K.K., light source: F-10, polarizing film: manufactured by Kyowa Kagaku K.K.) with the blank value of 30000. The results are shown in table 6.

[ TABLE 6]

< evaluation of light resistance >

An ultraviolet cut filter (color OPTICAL GLASS L38; manufactured by HOYA corporation; cut off light at 380nm or less) was placed on the obtained COLORED pattern, and the xenon lamp was irradiated for 48 hours using a light resistance tester (SUNTEST CPS +; manufactured by toyo seiko corporation), and the chromaticity of the COLORED pattern after irradiation was measured, and the measured value was measured in accordance with JIS Z8730: 2009 (7. Method for calculating color difference) the color difference Δ Eab before and after irradiation was determined by the method described in (7). Further, with respect to chromaticity, the spectral content was measured using a colorimeter (OSP-SP-200: manufactured by Olympus corporation), and the xy chromaticity coordinates (x, Y) and stimulus value Y in the XYZ color system of CIE were measured using the isochromatic function of a C illuminant. The results are shown in Table 7.

[ TABLE 7]

Industrial applicability

The colored resin composition of the present invention can be used to produce a color filter having excellent contrast and light resistance.

Claims

1. A colored resin composition comprising a colorant and a resin, the colorant comprising: a compound represented by the formula (I),

in the formula (I), the compound is shown in the specification,

ring T ¹ Is represented by the formula (R) ³ A 1) to formula (R) ³ -any of the rings represented by a 4),

ring T ² Is represented by the formula (R) ⁴ A 1) to formula (R) ⁴ -any of the rings represented by a 4),

L ¹ and L ² Each independently being any one of the groups represented by the formulae (L-1) to (L-7),

k represents an integer of 0 or more and 4 or less,

M ⁿ⁺ represents a metal cation of valency n,

n represents an integer of 2 or more and 5 or less,

r represents M ⁿ⁺ The number of (b) is selected so that the valence of the formula (I) is 0,

formula (R) ³ A 1) to formula (R) ³ A 4) and formula (R) ⁴ A 1) to formula (R) ⁴ In a 4), the term "L" means the same as L ¹ Or L ² C means a bonding end to a carbon atom,

in the formulae (L-1) to (L-7), n means a bonding end to a nitrogen atom, and s means a bonding end to a sulfur atom.

2. The colored resin composition according to claim 1, further comprising a polymerizable compound and a polymerization initiator.

3. A color filter formed from the colored resin composition according to any one of claims 1 to 2.

4. A display device comprising the color filter of claim 3.