CN111868176B - Compound, colored resin composition, color filter and display device - Google Patents

Abstract

The invention provides a compound and a colored resin composition capable of forming a color filter and a display device with excellent heat resistance.

Description

Compound, colored resin composition, color filter and display device

Technical Field

The present invention relates to a compound.

Background

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

Disclosure of Invention

Technical subject

However, a color filter formed from a colored resin composition containing the above-mentioned compounds, which have been known conventionally, may not sufficiently satisfy heat resistance. Accordingly, the present invention provides a compound capable of forming a color filter having excellent heat resistance.

Means for solving the problems

The present invention includes the following inventions.

[1] A compound represented by formula (IA), formula (IB), or formula (IC):

[ in the formula (IA),

R¹～R⁸each independently represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group having 1 to 20 carbon atoms which may have a substituent;

R^9A～R^12Aeach independently represents a C1-20 hydrocarbon group which may have a substituent, R^9A～R^12AAt least one of which is of-CO₂ ^-A hydrocarbon group having 1 to 20 carbon atoms as a substituent;

QAⁿ⁺a metal ion representing a valence of n;

n represents an integer of 2 or more;

bA denotes QAⁿ⁺The number of (2);

in the reaction of R¹～R⁸And R^9A～R^12AIn the case where the total number of negative charges contained in (a) is kA, aA is (n × bA)/kA.]

[ in the formula (IB),

R¹～R⁸represents the same meaning as previously described;

R^9B～R^12Beach independently represents a C1-20 hydrocarbon group which may have a substituent, R^9B～R^12BAt least one of which is of-SO₃ ^-An aliphatic hydrocarbon group having 1 to 20 carbon atoms as a substituent;

QBⁿ⁺a metal ion representing a hydrogen positive ion or an n-valent metal ion;

n represents an integer of 2 or more;

bB denotes QBⁿ⁺The number of (2);

in the reaction of R¹～R⁸And R^9B～R^12BIn (b) contains-SO₃ ^-When kB are defined as a total of (a), aB is (n × bB)/kB.]

[ in the formula (IC),

R¹～R⁸represents the same meaning as previously described;

R^9C～R^12Ceach independently represents a C1-20 hydrocarbon group which may have a substituent, R^9C～R^12CAt least one of which is of-CONZ¹Z²A C1-20 hydrocarbon group as a substituent, and R^9C～R^12CAt least one of the above groups is an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms;

Z¹and Z²Each independently represents a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent or a hydrogen atom.]

[2] A colored resin composition comprising a colorant and a resin, wherein the colorant comprises at least one selected from the group consisting of the compound represented by the formula (IA), the compound represented by the formula (IB) and the compound represented by the formula (IC) as defined in [1 ].

[3] The colored resin composition according to [2], further comprising a polymerizable compound and a polymerization initiator.

[4] A color filter formed from the colored resin composition according to [2] or [3 ].

[5] A display device comprising the color filter according to [4 ].

Effects of the invention

According to the present invention, a novel compound capable of forming a color filter having excellent heat resistance is provided.

Detailed Description

< Compound >

The compound according to the present invention is a compound represented by formula (IA) (hereinafter, sometimes referred to as compound (IA)), a compound represented by formula (IB) (hereinafter, sometimes referred to as compound (IB)), or a compound represented by formula (IC) (hereinafter, sometimes referred to as compound (IC)). Hereinafter, the present invention will be described in detail using the formula (IA), the formula (IB) or the formula (IC), but the compound (IA), the compound (IB) or the compound (IC) includes a resonance structure of the formula (IA), the formula (IB) or the formula (IC), and further includes a compound obtained by rotating each group in the formula (IA), the formula (IB), the formula (IC) or a resonance structural formula thereof around a bonding axis of a carbon-carbon single bond or a carbon-nitrogen single bond.

Compound (IA)

A compound represented by the formula (IA).

[ in the formula (IA),

R¹～R⁸each independently represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group having 1 to 20 carbon atoms which may have a substituent;

R^9A～R^12Aeach independently represents a C1-20 hydrocarbon group which may have a substituent, R^9A～R^12AAt least one of which is of-CO₂ ^-A hydrocarbon group having 1 to 20 carbon atoms as a substituent;

QAⁿ⁺a metal ion representing a valence of n;

n represents an integer of 2 or more;

bA denotes QAⁿ⁺The number of (2);

in the reaction of R¹～R⁸And R^9A～R^12AIn the case where the total number of negative charges contained in (a) is kA, aA is (n × bA)/kA.]

R¹～R⁸The alkyl group having 1 to 20 carbon atoms may be any of linear, branched and cyclic. Specific examples of the linear or branched alkyl group include: methyl, ethyl, propyl and isobutylAlkyl, butyl, t-butyl, hexyl, heptyl, octyl, nonyl, decyl, heptadecyl, undecyl, and the like. Examples of the cyclic alkyl group include: cyclopropyl, 1-methylcyclopropyl, cyclopentyl, cyclohexyl, 1, 2-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, 4-cyclohexylcyclohexyl and the like.

As R¹～R⁸The substituent of the alkyl group having 1 to 20 carbon atoms includes: halogen atoms such as fluorine atom, chlorine atom, and iodine atom; a hydroxyl group; -NR^aR^b(R^aAnd R^bEach independently represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms); a nitro group; alkoxy groups having 1 to 10 carbon atoms such as methoxy and ethoxy; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl.

As R¹～R⁸Examples of the alkoxy group having 1 to 20 carbon atoms include a group in which-O-is bonded to a bond of the alkyl group having 1 to 20 carbon atoms. Specifically, there may be mentioned: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, pentoxy, hexoxy, heptoxy, octoxy, 2-ethylhexoxy and the like.

As R¹～R⁸The substituent of the alkoxy group having 1 to 20 carbon atoms includes: halogen atoms such as fluorine atom, chlorine atom, and iodine atom; a hydroxyl group; -NR^cR^d(R^cAnd R^dEach independently represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms); a nitro group; alkoxy groups having 1 to 10 carbon atoms such as methoxy and ethoxy; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl.

In the compound (IA), in R¹～R⁸In, R¹～R⁴Particularly preferred is a hydrogen atom. Furthermore, R⁵～R⁸Each independently of the other, is preferably a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group having 1 to 20 carbon atoms which may have a substituent, and more preferably a hydrogen atom or a hydroxyl group.

In the compound (IA), R¹～R⁸(preferably R)⁵～R⁸) 2 to 4 of these are each independently preferably a hydroxyl group.

As R^9A～R^12AExamples of the hydrocarbon group having 1 to 20 carbon atoms include aliphatic hydrocarbon groups having 1 to 20 carbon atoms and aromatic hydrocarbon groups having 6 to 20 carbon atoms.

The aliphatic hydrocarbon group having 1 to 20 carbon atoms may be either saturated or unsaturated, and is preferably saturated. The aliphatic hydrocarbon group having 1 to 20 carbon atoms may be linear, branched or cyclic, and is preferably linear or branched.

Examples of the linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms include: straight aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, vinyl, 1-propenyl, and 2-propenyl (allyl); 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 15 carbon atoms, more preferably 1 to 10 carbon atoms.

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

The methylene group contained in the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be replaced by-O-. Examples of the group in which a methylene group contained in the aliphatic hydrocarbon group is replaced with-O-include groups represented by the following formulae. In the following formulae, a represents a bond.

Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include: phenyl, xylyl, trimethylphenyl, dipropylphenyl, bis (2, 2-dimethylpropyl) phenyl, naphthyl and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 16, more preferably 6 to 12, and still more preferably 6 to 9.

R^9A～R^12AThe hydrocarbyl group having 1 to 20 carbon atoms may have a substituent, and examples of the substituent include: -CO₂ ^-(ii) a A carboxyl group; -SO₃ ^-；-CONZ¹Z²(Z¹And Z²Each independently represents a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent or a hydrogen atom); halogen atoms such as fluorine atom, chlorine atom, and iodine atom; alkoxy groups having 1 to 10 carbon atoms such as methoxy and ethoxy; a hydroxyl group; a sulfamoyl group; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl.

substituent-CONZ¹Z²In as Z¹And Z²Examples of the hydrocarbon group having 1 to 10 carbon atoms include aliphatic hydrocarbon groups having 1 to 10 carbon atoms and aromatic hydrocarbon groups having 6 to 10 carbon atoms.

The aliphatic hydrocarbon group having 1 to 10 carbon atoms may be either saturated or unsaturated. The aliphatic hydrocarbon group having 1 to 10 carbon atoms may be any of linear, branched and cyclic.

Specific examples of the aliphatic hydrocarbon group having 1 to 10 carbon atoms and the aromatic hydrocarbon group having 6 to 10 carbon atoms include R^9A～R^12AThe number of carbon atoms in the hydrocarbon group having 1 to 20 carbon atoms is 1 to 10.

substituent-CONZ¹Z²In, Z¹And Z²The hydrocarbon group having 1 to 10 carbon atoms may have a substituent, and examples of the substituent include: halogen atoms such as fluorine atom, chlorine atom, and iodine atom; alkoxy groups having 1 to 10 carbon atoms such as methoxy and ethoxy; a hydroxyl group; a sulfamoyl group; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl.

R^9A～R^12AAt least one of which is of-CO₂ ^-The substituent is a hydrocarbon group having 1 to 20 carbon atoms. The aforesaid has a-CO₂ ^-The substituted hydrocarbon group having 1 to 20 carbon atoms preferably has 1 to 2-CO groups₂ ^-More preferably having 1-CO₂ ^-And a method for producing the same. Further, the aforementioned-CO₂ ^-Preferably bonded to a compound having-CO₂ ^-At least the terminal of a C1-20 hydrocarbon group as a substituent. As such having a-CO₂ ^-Examples of the hydrocarbyl group having 1 to 20 carbon atoms as a substituent include those represented by the following formulae. In the following formulae, a represents a bond.

R^9A～R^12AAt least one of them is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. The optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms is preferably a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group or a bis (2, 2-dimethylpropyl) phenyl group, and more preferably a2, 4-dimethylphenyl group or a2, 4, 6-trimethylphenyl group.

In the compound (IA), preferably, R^9AAnd R^12AEach independently of the other is a compound having-CO₂ ^-A C1-20 hydrocarbon group as a substituent, R^10AAnd R^11AEach independently an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.

As QAⁿ⁺Examples of the n-valent metal ion include: alkaline earth metal ions such as magnesium ions, calcium ions, strontium ions, and barium ions; 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. QAⁿ⁺Preferably an alkaline earth metal ion, more preferably a barium ion.

n is preferably 5 or less, more preferably 4 or less, still more preferably 3 or less, and still more preferably 2.

The compound (IA) is electrically neutral when R is¹～R⁸And R^9A～R^12AIn the case where the total number of negative charges contained in (a) is kA, aA is (n × bA)/kA.

In addition, bA is preferably 1 to 3, more preferably 1 to 2, and further preferably 1.

In addition, in R^9A～R^12AThe hydrocarbon group having 1 to 20 carbon atoms does not have-SO₃ ^-When the substituent(s) is (are), kA means-CO contained in the formula (IA)₂ ^-The total number of (2) is preferably 1 to 5, more preferably 2 to 4, and still more preferably 2.

Examples of the compound (IA) include compounds represented by the formulae (IA-1) to (IA-108) shown in tables 1 to 2.

The compound (IA) is preferably a compound represented by any one of the formulae (IA-1) to (IA-54), more preferably a compound represented by any one of the formulae (IA-1) to (IA-18), and still more preferably a compound represented by any one of the formulae (IA-1) to (IA-3).

[ Table 1]

[ Table 2]

R1～R4

R5

R6

R7

R8

R9A

R10A

R11A

R12A

QAn+

aA

bA

(IA-73)

H

OH

OH

OH

OH

ca5

ph1

ph1

ca5

Ba2+

1

1

(IA-74)

H

H

H

H

H

ca5

ph1

ph1

ca5

Ba2+

1

1

(IA-75)

H

OH

H

H

OH

ca5

ph1

ph1

ca5

Ba2+

1

1

(IA-76)

H

OH

OH

OH

OH

ca5

ph2

ph2

ca5

Ba2+

1

1

(IA-77)

H

H

H

H

H

ca5

ph2

ph2

ca5

Ba2+

1

1

(IA-78)

H

OH

H

H

OH

ca5

ph2

ph2

ca5

Ba2+

1

1

(IA-79)

H

OH

OH

OH

OH

ca5

ph3

ph3

ca5

Ba2+

1

1

(IA-80)

H

H

H

H

H

ca5

ph3

ph3

ca5

Ba2+

1

1

(IA-81)

H

OH

H

H

OH

ca5

ph3

ph3

ca5

Ba2+

1

1

(IA-82)

H

OH

OH

OH

OH

ca5

ph4

ph4

ca5

Ba2+

1

1

(IA-83)

H

H

H

H

H

ca5

ph4

ph4

ca5

Ba2+

1

1

(IA-84)

H

OH

H

H

OH

ca5

ph4

ph4

ca5

Ba2+

1

1

(IA-85)

H

OH

OH

OH

OH

ca5

ph5

ph5

ca5

Ba2+

1

1

(IA-86)

H

H

H

H

H

ca5

ph5

ph5

ca5

Ba2+

1

1

(IA-87)

H

OH

H

H

OH

ca5

ph5

ph5

ca5

Ba2+

1

1

(IA-88)

H

OH

OH

OH

OH

ca5

ph6

ph6

ca5

Ba2+

1

1

(IA-89)

H

H

H

H

H

ca5

ph6

ph6

ca5

Ba2+

1

1

(IA-90)

H

OH

H

H

OH

ca5

ph6

ph6

ca5

Ba2+

1

1

(IA-91)

H

OH

OH

OH

OH

ca6

ph1

ph1

ca6

Ba2+

1

1

(IA-92)

H

H

H

H

H

ca6

ph1

ph1

ca6

Ba2+

1

1

(IA-93)

H

OH

H

H

OH

ca6

ph1

ph1

ca6

Ba2+

1

1

(IA-94)

H

OH

OH

OH

OH

ca6

ph2

ph2

ca6

Ba2+

1

1

(IA-95)

H

H

H

H

H

ca6

ph2

ph2

ca6

Ba2+

1

1

(IA-96)

H

OH

H

H

OH

ca6

ph2

ph2

ca6

Ba2+

1

1

(IA-97)

H

OH

OH

OH

OH

ca6

ph3

ph3

ca6

Ba2+

1

1

(IA-98)

H

H

H

H

H

ca6

ph3

ph3

ca6

Ba2+

1

1

(IA-99)

H

OH

H

H

OH

ca6

ph3

ph3

ca6

Ba2+

1

1

(IA-100)

H

OH

OH

OH

OH

ca6

ph4

ph4

ca6

Ba2+

1

1

(IA-101)

H

H

H

H

H

ca6

ph4

ph4

ca6

Ba2+

1

1

(IA-102)

H

OH

H

H

OH

ca6

ph4

ph4

ca6

Ba2+

1

1

(IA-103)

H

OH

OH

OH

OH

ca6

ph5

ph5

ca6

Ba2+

1

1

(IA-104)

H

H

H

H

H

ca6

ph5

ph5

ca6

Ba2+

1

1

(IA-105)

H

OH

H

H

OH

ca6

ph5

ph5

ca6

Ba2+

1

1

(IA-106)

H

OH

OH

OH

OH

ca6

ph6

ph6

ca6

Ba2+

1

1

(IA-107)

H

H

H

H

H

ca6

ph6

ph6

ca6

Ba2+

1

1

(IA-108)

H

OH

H

H

OH

ca6

ph6

ph6

ca6

Ba2+

1

1

In tables 1 to 2, ph1 to ph6 represent groups represented by the following formulae (— meaning bond).

In tables 1 to 2, ca1 to ca6 represent groups represented by the following formulae (— meaning bond).

Compound (IB)

A compound represented by the formula (IB).

[ in the formula (IB), R¹～R⁸Represents the same meaning as previously described;

R^9B～R^12Beach independently represents a C1-20 hydrocarbon group which may have a substituent, R^9B～R^12BAt least one of which is of-SO₃ ^-An aliphatic hydrocarbon group having 1 to 20 carbon atoms as a substituent;

QBⁿ⁺a metal ion representing a hydrogen positive ion or an n-valent metal ion;

n represents an integer of 2 or more;

bB denotes QBⁿ⁺The number of (2);

in the reaction of R¹～R⁸And R^9B～R^12BIn (b) contains-SO₃ ^-When kB are defined as a total of (a), aB is (n × bB)/kB.]

In the compound (IB), in R¹～R⁸In, R¹～R⁴Particularly preferred is a hydrogen atom. Furthermore, R⁵～R⁸Each independently of the other, is preferably a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group having 1 to 20 carbon atoms which may have a substituent, and more preferably a hydrogen atom or a hydroxyl group.

In the compound (IB), R is preferred¹～R⁸(preferably R)⁵～R⁸) 2 to 4 of which are each independently a hydroxyl group. In particular, R is preferable from the viewpoint of good heat resistance and light resistance⁵And R⁸Is hydroxy，R⁶And R⁷Is a hydrogen atom.

As R^9B～R^12BThe hydrocarbyl group having 1 to 20 carbon atoms is represented by^9A～R^12AThe hydrocarbon groups having 1 to 20 carbon atoms are the same, and the preferable range of the number of carbon atoms is the same.

R^9B～R^12BThe hydrocarbyl group having 1 to 20 carbon atoms may have a substituent, and examples of the substituent include: -SO₃ ^-(ii) a Halogen atoms such as fluorine atom, chlorine atom, and iodine atom; alkoxy groups having 1 to 10 carbon atoms such as methoxy and ethoxy; a hydroxyl group; a sulfamoyl group; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl.

R^9B～R^12BAt least one of which is of-SO₃ ^-An aliphatic hydrocarbon group having 1 to 20 carbon atoms as a substituent. The foregoing has an-SO₃ ^-The aliphatic hydrocarbon group having 1 to 20 carbon atoms as a substituent preferably has 1 to 2-SO₃ ^-More preferably having 1-SO₃ ^-. Further, the aforementioned-SO₃ ^-Preferably bonded to a group having-SO₃ ^-At least the terminal of the aliphatic hydrocarbon group having 1 to 20 carbon atoms as a substituent. As such having-SO₃ ^-Examples of the aliphatic hydrocarbon group having 1 to 20 carbon atoms as a substituent include groups represented by the following formulae. In the following formulae, a represents a bond.

R^9B～R^12BAt least one of the above groups is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. The optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms is preferably a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group or a di (2, 2-dimethylpropyl) phenyl group, and more preferably a2, 4-dimethylphenyl group or a2, 4, 6-trimethylphenyl group.

Among the compounds (IB), preferred is，R^9BAnd R^12BEach independently of the other is substituted with-SO₃ ^-An aliphatic hydrocarbon group having 1 to 20 carbon atoms as a substituent, R^10BAnd R^11BEach independently an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.

As QBⁿ⁺The metal ion having a valence of n is exemplified by QAⁿ⁺The same metal ions having n-valent states are used. QBⁿ⁺Preferably hydrogen positive ions, alkaline earth metal ions or typical metal ions, more preferably hydrogen positive ions, barium ions, magnesium ions, aluminum ions. From the viewpoint of heat resistance and light resistance, hydrogen cations, barium ions, or aluminum ions are preferable.

In addition, in QBⁿ⁺When it is a hydrogen cation, the hydrogen cation is in contact with-SO₃ ^-As a whole as-SO₃H is present.

Preferred ranges of n are the same as described above.

The compound (IB) is electrically neutral when R is¹～R⁸And R^9B～R^12BIn (b) contains-SO₃ ^-When kB are defined as a total of (a), aB is (n × bB)/kB.

Further, bB is preferably 1 to 3, more preferably 1 to 2, and further preferably 1.

Furthermore, kB is preferably 1 to 5, more preferably 2 to 4, and further preferably 2.

Examples of the compound (IB) include compounds represented by the formulae (IB-1) to (IB-432) shown in tables 3 to 8.

The compound (IB) is preferably a compound represented by the formula (IB-1) to the formula (IB-54), the formula (IB-109) to the formula (IB-162), the formula (IB-217) to the formula (IB-270), the formula (IB-325) to the formula (IB-378),

more preferably compounds represented by the formulae (IB-37) to (IB-54), the formulae (IB-145) to (IB-162), the formulae (IB-253) to (IB-270), the formulae (IB-361) to (IB-378),

further preferred are compounds represented by the formulae (IB-37) to (IB-39), the formulae (IB-145) to (IB-147), the formulae (IB-253) to (IB-255), and the formulae (IB-361) to (IB-363).

[ Table 3]

[ Table 4]

[ Table 5]

[ Table 6]

[ Table 7]

[ Table 8]

In tables 3 to 8, ph1 to ph6 represent the same groups as described above.

In tables 3 to 8, su1 to su6 represent groups represented by the following formulae (— denoted by a bond).

Compound (IC)

A compound represented by the formula (IC).

[ in the formula (IC), R¹～R⁸Represents the same meaning as previously described;

R^9C～R^12Ceach independently represents a C1-20 hydrocarbon group which may have a substituent, R^9C～R^12CAt least one of which is of-CONZ¹Z²A C1-20 hydrocarbon group as a substituent, and R^9C～R^12CAt least one of the above groups is an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms;

Z¹and Z²Each independently represents a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent or a hydrogen atom.]

In the compound (IC), R¹～R⁸In, R¹～R⁴Particularly preferred is a hydrogen atom. Furthermore, R⁵～R⁸Each independently of the other, is preferably a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group having 1 to 20 carbon atoms which may have a substituent, and more preferably a hydrogen atom or a hydroxyl group.

In the compound (IC), R is preferred¹～R⁸(preferably R)⁵～R⁸) 2 to 4 of which are each independently a hydroxyl group.

As R^9C～R^12CThe hydrocarbyl group having 1 to 20 carbon atoms is represented by^9A～R^12AThe hydrocarbon groups having 1 to 20 carbon atoms are the same, and the preferable range of the number of carbon atoms is the same.

R^9C～R^12CThe hydrocarbyl group having 1 to 20 carbon atoms may have a substituent, and examples of the substituent include: -CONZ¹Z²(ii) a Halogen atoms such as fluorine atom, chlorine atom, and iodine atom; alkoxy groups having 1 to 10 carbon atoms such as methoxy and ethoxy; a hydroxyl group; a sulfamoyl group; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl.

Z¹And Z²The same meanings as described above are indicated.

Compound (I)In (IC), Z¹And Z²Each independently is preferably a hydrocarbon group having 1 to 5 carbon atoms or a hydrogen atom which may have a substituent, more preferably a hydrocarbon group having 1 to 3 carbon atoms which may have a substituent, and still more preferably a hydrogen atom.

R^9C～R^12CAt least one of which is of-CONZ¹Z²The substituent is a hydrocarbon group having 1 to 20 carbon atoms. The foregoing has the formula-CONZ¹Z²The substituted hydrocarbon group having 1 to 20 carbon atoms preferably has 1 to 2-CONZ groups¹Z²More preferably having 1-CONZ¹Z². Further, the aforementioned-CONZ¹Z²Preferably bonded to a group having-CONZ¹Z²At least the terminal of a C1-20 hydrocarbon group as a substituent. As such having-CONZ¹Z²Examples of the hydrocarbyl group having 1 to 20 carbon atoms as a substituent include those represented by the following formula. In the following formulae, a represents a bond.

R^9C～R^12CAt least one of them is an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms. The optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms is preferably a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group or a di (2, 2-dimethylpropyl) phenyl group, and more preferably a2, 4-dimethylphenyl group or a2, 4, 6-trimethylphenyl group.

In the compound (IC), preferably, R^9CAnd R^11CEach independently is a compound having-CONZ¹Z²A C1-20 hydrocarbon group as a substituent, R^10CAnd R^12CEach independently an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.

Examples of the compound (IC) include compounds represented by the formulae (IC-1) to (IC-108) shown in tables 9 to 10.

The compound (IC) is preferably a compound represented by any one of the formulae (IC-1) to (IC-54), more preferably a compound represented by any one of the formulae (IC-1) to (IC-18), and still more preferably a compound represented by any one of the formulae (IC-1) to (IC-3).

[ Table 9]

[ Table 10]

R1～R4

R5

R6

R7

R8

R9C

R10C

R11C

R12C

(IC-73)

H

OH

OH

OH

OH

bm5

ph1

ph1

bm5

(IC-74)

H

H

H

H

H

bm5

ph1

ph1

bm5

(IC-75)

H

OH

H

H

OH

bm5

ph1

ph1

bm5

(IC-76)

H

OH

OH

OH

OH

bm5

ph2

ph2

bm5

(IC-77)

H

H

H

H

H

bm5

ph2

ph2

bm5

(IC-78)

H

OH

H

H

OH

bm5

ph2

ph2

bm5

(IC-79)

H

OH

OH

OH

OH

bm5

ph3

ph3

bm5

(IC-80)

H

H

H

H

H

bm5

ph3

ph3

bm5

(IC-81)

H

OH

H

H

OH

bm5

ph3

ph3

bm5

(IC-82)

H

OH

OH

OH

OH

bm5

ph4

ph4

bm5

(IC-83)

H

H

H

H

H

bm5

ph4

ph4

bm5

(IC-84)

H

OH

H

H

OH

bm5

ph4

ph4

bm5

(IC-85)

H

OH

OH

OH

OH

bm5

ph5

ph5

bm5

(IC-86)

H

H

H

H

H

bm5

ph5

ph5

bm5

(IC-87)

H

OH

H

H

OH

bm5

ph5

ph5

bm5

(IC-88)

H

OH

OH

OH

OH

bm5

ph6

ph6

bm5

(IC-89)

H

H

H

H

H

bm5

ph6

ph6

bm5

(IC-90)

H

OH

H

H

OH

bm5

ph6

ph6

bm5

(IC-91)

H

OH

OH

OH

OH

bm6

ph1

ph1

bm6

(IC-92)

H

H

H

H

H

bm6

ph1

ph1

bm6

(IC-93)

H

OH

H

H

OH

bm6

ph1

ph1

bm6

(IC-94)

H

OH

OH

OH

OH

bm6

ph2

ph2

bm6

(IC-95)

H

H

H

H

H

bm6

ph2

ph2

bm6

(IC-96)

H

OH

H

H

OH

bm6

ph2

ph2

bm6

(IC-97)

H

OH

OH

OH

OH

bm6

ph3

ph3

bm6

(IC-98)

H

H

H

H

H

bm6

ph3

ph3

bm6

(IC-99)

H

OH

H

H

OH

bm6

ph3

ph3

bm6

(IC-100)

H

OH

OH

OH

OH

bm6

ph4

ph4

bm6

(IC-101)

H

H

H

H

H

bm6

ph4

ph4

bm6

(IC-102)

H

OH

H

H

OH

bm6

ph4

ph4

bm6

(IC-103)

H

OH

OH

OH

OH

bm6

ph5

ph5

bm6

(IC-104)

H

H

H

H

H

bm6

ph5

ph5

bm6

(IC-105)

H

OH

H

H

OH

bm6

ph5

ph5

bm6

(IC-106)

H

OH

OH

OH

OH

bm6

ph6

ph6

bm6

(IC-107)

H

H

H

H

H

bm6

ph6

ph6

bm6

(IC-108)

H

OH

H

H

OH

bm6

ph6

ph6

bm6

In tables 9 to 10, ph1 to ph6 represent the same groups as described above.

In tables 9 to 10, bm1 to bm6 represent groups represented by the following formulae (a bond).

A compound represented by the formula (IA), and Qⁿ⁺The compound represented by formula (IB) when the metal ion has a valence of n corresponds to a compound represented by formula (pt5) in the following chemical formula. Further, Qⁿ⁺The compound represented by formula (IB) and the compound represented by formula (IC) when being hydrogen cations correspond to the compound represented by formula (pt4) in the following chemical formula.

The compound represented by the formula (pt5) and the compound represented by the formula (pt4) can be produced by the following methods.

The compound represented by the formula (pt5) can be produced by reacting the compound represented by the formula (pt4) with a halide (preferably chloride), acetate, phosphate, sulfate, silicate, cyanide, or the like containing an n-valent metal ion.

The compound represented by formula (pt4) can be produced by reacting a compound represented by formula (pt1), a compound represented by formula (pt2), and a compound represented by formula (pt 3). In the present reaction, the total amount of the compound represented by the formula (pt1) and the compound represented by the formula (pt2) to be used is preferably 1.5 to 2.5mol based on 1mol of the compound represented by the formula (pt 3).

[ formulae (pt1) to (pt2) and formulae (pt4) to (pt5), R¹～R⁸Same as above, R^9X～R^12XRepresents R^9A～R^12A、R^9B～R^12BOr R^9C～R^12C，QXⁿ⁺Representation QAⁿ⁺、QBⁿ⁺Or QCⁿ⁺aX represents aA, aB or aC, bX represents bA, bB or bC, R^9A～R^12A、R^9B～R^12B、R^9C～R^12CaA, aB, aC, bA, bB and bC are the same as above, R^9aX～R^12aXEach independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.]

< colored resin composition >

The colored resin composition of the present invention comprises a colorant (a) and a resin (B), wherein the colorant (a) comprises at least one selected from the group consisting of a compound represented by formula (IA), a compound represented by formula (IB), and a compound represented by formula (IC).

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

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

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

< colorant (A) >)

The colored resin composition of the present invention contains at least one selected from the group consisting of the compound (IA), the compound (IB), and the compound (IC) as the colorant (a). The content of the compound (IA), the compound (IB) and/or the compound (IC) is preferably 0.1 to 150 parts by mass, more preferably 0.5 to 100 parts by mass, and still more preferably 1 to 80 parts by mass, based on 100 parts by mass of the resin (B).

The content of the total of the compound (IA), the compound (IB), and the compound (IC) 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.

The colored resin composition of the present invention may contain a dye (a1) and a pigment (a2) as the colorant (a) in addition to the compound (IA), the compound (IB), and the compound (IC).

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 dyes having hues other than pigments in The color index (published by The Society of Dyers and Colourists), and known dyes described in The color handbook (color dyeing Co., Ltd.). Further, depending on the chemical structure, there can be enumerated: azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinonimine dyes, methine dyes, azomethine dyes, squarylium dyes (excluding compound (IA), compound (IB), and compound (IC)), acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and the like. Among them, organic solvent-soluble dyes are preferable.

The pigment (a2) is not particularly limited, and known pigments can be used, and examples thereof include pigments classified as pigments by The color index (published by The Society of Dyers and Colourists).

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

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, etc.;

c.i. pigment violet 1, 19, 23, 29, 32, 36, 38 and the like violet pigment;

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 in the colored resin composition.

Here, the "total amount of solid content" in the present specification means an amount obtained by removing the content of the solvent from the total amount of the colored resin composition. The total amount of solid components and the contents of the respective components relative thereto can be measured by a known analytical method 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 one (a) (hereinafter, sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides. The resin (B) further preferably has at least one structural unit selected from the group consisting 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) (wherein (a) and (b) are different) (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, succinic acid mono [2- (meth) acryloyloxyethyl ] ester, and the like, and acrylic acid, methacrylic acid, maleic anhydride are preferable.

(b) Preferably a monomer having a cyclic ether structure of 2 to 4 carbon atoms (for example, at least one 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" means at least one selected from the group consisting of 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, and 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decyl ester, 3-ethyl-3- (meth) acryloyloxymethyloxetane, tetrahydrofurfuryl (meth) acrylate, etc., preferably glycidyl (meth) acrylate, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)^2,6]Decyl ester, 3-ethyl-3- (meth) acryloyloxymethyloxetane.

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^2,6]Decyl-8-yl ester, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene and the like, and preferably styrene, vinyltoluene, 2-hydroxyethyl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide and the like.

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 adding (a) to the copolymer of (b) and (c) and then further reacting a carboxylic acid anhydride.

The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000.

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 further 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 necessary for neutralizing 1g of the resin (B), and can be determined, for example, by titration using an aqueous solution of potassium hydroxide.

The content of the resin (B) is preferably 30 to 99.9% by mass, more preferably 50 to 99.5% by mass, and still more preferably 70 to 99% by mass, based on the total amount of solid components in the colored resin composition.

When the colored resin composition of the present invention contains the polymerizable compound (C) and the polymerization initiator (D), 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 in the colored 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 compounds having a polymerizable ethylenically unsaturated bond, and (meth) acrylate compounds are preferable.

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

The weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.

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 to initiate polymerization, and a known polymerization initiator can be used. Examples of the polymerization initiator that generates active radicals include: n-benzoyloxy-1- (4-phenylmercaptophenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylmercaptophenyl) octan-1-one-2-imine, N-benzoyloxy-1- (4-phenylmercaptophenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- (4-phenylmercaptophenyl) -3-cyclohexylpropane-1-one-2-imine, 2-methyl-2-morpholino-1- (4-methylhydrothiophenyl) propane-1-one, N-benzoyloxy-1- (4-phenylmercaptophenyl) octane-1-one-2-imine, N-benzoyloxy-1- (4-phenylmercaptophenyl) propane-1-one, N-benzoyloxy-1- (4-phenylmercaptophenyl) propane-2-imine, N-benzoyloxy-1- (4-phenylmercaptophenyl) propane-1-one, N-methyl-2-imine, N-methyl-2-methyl-morpholino-1-one, N-methyl-1-2-imine, N-benzoyloxy-1- (4-phenylthiophenyl) propane-imine, N-methyl-1-imine, N-methyl-2-imine, N-2-methyl-morpholino-1-imine, N, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, 1-hydroxycyclohexylphenyl ketone, 2, 4-bis (trichloromethyl) -6-piperonyl-1, 3, 5-triazine, 2,4, 6-trimethylbenzoyldiphenylphosphine oxide, 2' -bis (2-chlorophenyl) -4,4',5,5' -tetraphenylbenzimidazole 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). When 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 shortened, so that the productivity of the color filter is improved.

< polymerization initiation assistant (D1) >)

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

Examples of the polymerization initiation aid (D1) include: 4,4' -bis (dimethylamino) benzophenone (known as Michler's ketone), 4' -bis (diethylamino) benzophenone, 9, 10-dimethoxyanthracene, 2, 4-diethylthioxanthone, N-phenylglycine, and the like.

When the polymerization initiator 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). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.

< solvent (E) >

The solvent (E) is not particularly limited, and a solvent generally used in this field can be used. Examples thereof include: an ester solvent (a solvent containing-COO-but not containing-O-in the molecule), an ether solvent (a solvent containing-O-but not containing-COO-, in the molecule), an ether ester solvent (a solvent containing-COO-and-O-in the molecule), a ketone solvent (a solvent containing-CO-but not containing-COO-, in the molecule), an alcohol solvent (a solvent containing OH but not containing-O-, -CO-, and-COO-, in the molecule), an aromatic hydrocarbon solvent, an amide solvent, dimethyl sulfoxide, and the like.

Examples of the solvent include:

ester solvents (solvents containing-COO-but 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-but not-COO-in the molecule) 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, etc.;

ether ester solvents (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-but not-COO-in the molecule) such as 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), heptanone, 4-methyl-2-pentanone, cyclohexanone, and the like;

alcohol solvents (solvents containing OH but not containing-O-, -CO-and-COO-) such as butanol, cyclohexanol and propylene glycol;

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

More preferred examples of the solvent include propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), ethyl lactate, and ethyl 3-ethoxypropionate.

When the solvent (E) is contained, the content of the solvent (E) is preferably 60 to 95% by mass, and more preferably 65 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 40% by mass, and more preferably 8 to 35% 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 does not become insufficient at the time of forming a color filter, so that the display characteristics tend to become good.

< leveling agent (F) >

Examples of the leveling agent (F) include: silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms. 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, there may be mentioned: TORAY SILICONE DC3PA, TORAY SILICONE SH7PA, TORAY SILICONE DC11PA, TORAY SILICONE SH21PA, TORAY SILICONE SH28PA, TORAY SILICONE SH29PA, TORAY SILICONE SH30PA, and TORAY SILICONE SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.); KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by shin-Etsu chemical industries, Ltd.); TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Mitigo high-tech materials, Japan Co., Ltd.), and the like.

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, there may be mentioned: FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Co.); MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC strain); EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352 (made by Mitsubishi Electron Synthesis), SURLON (registered trademark) S381, SURLON S382, SURLON SC101, and SURLON SC105 (made by Asahi Nitroson); and E5844 (manufactured by Dajin Fine Chemicals research institute).

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

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

< other ingredients >

The colored resin composition of the present invention may optionally contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and the like.

< 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 optionally 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 the like. Among them, photolithography is preferable.

The colored resin composition can produce a color filter having particularly excellent heat resistance by containing at least one selected from the group consisting of the compound represented by formula (IA), the compound represented by formula (IB), and the compound represented by formula (IC). The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, electronic paper, or the like) or a solid-state imaging device.

[ examples ]

The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these examples. In the examples, unless otherwise specified,% and part indicating contents and amounts used are on a mass basis.

Hereinafter, the structure of the compound was confirmed by MASS spectrometry (LC, model 1200 manufactured by Agilent; MASS, LC/MSD manufactured by Agilent).

(Synthesis example 1)

100 parts of 1-bromo-3, 5-dimethoxybenzene (manufactured by tokyo chemical industry co.), 55 parts of 2, 4-dimethylaniline (manufactured by tokyo chemical industry co.), 51 parts of potassium hydroxide (manufactured by Wako pure chemical industries co.), 1.5 parts of tetrabutylammonium bromide (manufactured by tokyo chemical industry co.), 2.3 parts of bis (tri-tert-butylphosphine) palladium (manufactured by Aldrich co.), 100 parts of water and 1000 parts of toluene (manufactured by Kanto chemical Co., Ltd.) were mixed and heated at 90 ℃ for 1 hour with stirring. After the reaction was completed, the organic layer was separated by separation with water and ethyl acetate. Then, the organic layer was dried over magnesium sulfate, and the solvent was distilled off by an evaporator to obtain 113 parts of a compound represented by formula (1A-1).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +258.2

Exact Mass (Exact Mass): +257.1

(Synthesis example 2)

70 parts of the compound represented by the formula (1A-1), 53 parts of methyl 4-chloro-4-oxobutyrate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 700 parts of toluene (manufactured by Kanto Kasei Co., Ltd.) were mixed and heated at 100 ℃ for 16 hours with stirring. After the reaction was completed, the solvent was distilled off, 700 parts of hexane (manufactured by kanto chemical corporation) was added to the obtained crude product, and the mixture was stirred for 2 hours, and the solid was separated by filtration to obtain 90 parts of the compound represented by formula (1A-2).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +372.2

Exact Mass (Exact Mass): +371.1

(Synthesis example 3)

34 parts of the compound represented by the formula (1A-2) was dissolved in 340 parts of methylene chloride (manufactured by Kanto chemical Co., Ltd.), cooled to 0 ℃ and 92 parts of boron tribromide (manufactured by Tokyo chemical Co., Ltd.) was added dropwise. After the completion of the dropwise addition, the temperature was raised to 10 ℃ and the mixture was stirred for 3 hours, then water was added to extract an organic layer, and the solvent was distilled off to obtain 89 parts of a crude product A. The crude product A contained 44% of the compound represented by the formula (1A-3) and 53% of the compound represented by the formula (1A-3-1).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +344.2

Exact Mass (Exact Mass): +343.1 type (1A-3)

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +330.2

Exact Mass (Exact Mass): +329.1 formula (1A-3-1)

(Synthesis example 4)

89 parts of the crude product a was dissolved in 370 parts of methanol (manufactured by kanto chemical corporation), cooled to 0 ℃, and then 51 parts of thionyl chloride (manufactured by tokyo chemical industry corporation) was added thereto. After completion of the reaction, water was added to the reaction mixture, the solvent was distilled off, and the obtained crude product was purified by silica gel column chromatography to obtain 53 parts of a compound represented by formula (1A-3).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +344.2

Exact Mass (Exact Mass): +343.1

(Synthesis example 5)

53 parts of the compound represented by the formula (1A-3) was dissolved in 530 parts of tetrahydrofuran (manufactured by Kanto Kagaku K.K.), and after cooling to 0 ℃ 460 parts of a borane 1M tetrahydrofuran solution (manufactured by Kanto Kagaku K.K.) was added dropwise, and after completion of the dropwise addition, the mixture was stirred at 20 ℃ for 5 hours. After the reaction was completed, water was added to distill off the solvent, and the obtained crude product was separated and purified by column chromatography to obtain 25 parts of the compound represented by formula (1A-4).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +330.3

Exact Mass (Exact Mass): +329.2

4 parts of the compound represented by the formula (1A-4), 2.5 parts of lithium hydroxide monohydrate (manufactured by Wako pure chemical industries, Ltd.), 20 parts of methanol (manufactured by Kanto Kagaku Co., Ltd.), and 20 parts of tetrahydrofuran (manufactured by Kanto Kagaku Co., Ltd.) were added, and the mixture was stirred at room temperature of 23 ℃ for 5 hours. After the completion of the reaction, the solvent was distilled off, and the obtained crude product was purified by silica gel column chromatography to obtain 1.7 parts of a compound represented by formula (1A-5).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +316.1

Exact Mass (Exact Mass): +315.2

(Synthesis example 6)

1.7 parts of the compound represented by the formula (1A-5) and 0.3 part of 3, 4-dihydroxy-3-cyclobutene-1, 2-dione (manufactured by Wako pure chemical industries, Ltd.) were dissolved in 65 parts of toluene (manufactured by Kanto chemical Co., Ltd.) and 17 parts of n-butanol (manufactured by Kanto chemical Co., Ltd.) and heated at 120 ℃ for 2 hours with stirring. After the completion of the reaction, the solvent was distilled off, and the obtained crude product was purified by silica gel column chromatography to obtain 0.85 part of the compound represented by formula (1A-6).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +709.3

Exact Mass (Exact Mass): +708.3

[ example 1]

Aqueous solution 1 was prepared by dissolving 1.0 part of the compound represented by formula (1A-6) in 25 parts of a 0.8% aqueous sodium hydroxide solution. Further, a liquid (aqueous solution 2) in which 1.7 parts of barium chloride dihydrate (manufactured by Wako pure chemical industries, Ltd.) was dissolved in 10 parts of water was prepared, and the aqueous solution 2 was slowly added to the aqueous solution 1 at room temperature of 23 ℃ and then stirred for 30 minutes. After the reaction was completed, the solid obtained by suction filtration was washed with water and acetone. The washed solid was dried under reduced pressure at 60 ℃ for 12 hours to obtain 1.2 parts of a compound represented by the formula (1A-7).

Synthesis example 7

26.0 parts of 2, 4-dimethylaniline (manufactured by Tokyo chemical industry Co., Ltd.) and 9.8 parts of 1, 4-butanesultone (manufactured by Tokyo chemical industry Co., Ltd.) were dissolved in 5.0 parts of toluene (manufactured by Kanto chemical Co., Ltd.) under a nitrogen atmosphere, and the mixture was heated at 100 ℃ for 3 hours with stirring. After completion of the reaction, toluene was distilled off by an evaporator, and 50 parts of a 10% aqueous sodium hydroxide solution was added to precipitate a solid. After obtaining a solid by suction filtration, the solid was washed with water and hexane. Drying was carried out at 60 ℃ under reduced pressure for 12 hours to obtain 20.0 parts of a compound represented by the formula (1B-1). The yield thereof was found to be 99%.

And (3) identification: (mass analysis) ionization mode-ESI-: m/z ═ M-Na ] +256.2

Exact Mass (Exact Mass): +279.09

(Synthesis example 8)

12.8 parts of the compound represented by the formula (1B-1), 10.0 parts of 1-bromo-3, 5-dimethoxybenzene (manufactured by Tokyo chemical industry Co., Ltd.), 0.3 parts of palladium acetate (manufactured by Tokyo chemical industry Co., Ltd.), and 0.47 parts of tri-tert-butylphosphine 1.0M hexane solution (manufactured by Wako pure chemical industries Co., Ltd.) were dissolved in 200 parts of toluene (manufactured by Tokyo chemical industry Co., Ltd.), and stirred at room temperature for 10 minutes under a nitrogen atmosphere. To this was added 9.0 parts of sodium tert-butoxide (Tokyo chemical industry Co., Ltd.), and the mixture was heated at 110 ℃ for 4 hours with stirring. After completion of the reaction, the reaction solution was neutralized with hydrochloric acid, and then separated into liquid and organic layer by water and ethyl acetate. Then, the organic layer was dried over magnesium sulfate, and ethyl acetate was distilled off by an evaporator to obtain 6.1 parts of a compound represented by formula (1B-2). The yield thereof was found to be 32%.

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +394.5

Exact Mass (Exact Mass): 393.16

(Synthesis example 9)

9.8 parts of the compound represented by the formula (1B-2) was dissolved in 27.0 parts of acetic acid (Wako pure chemical industries, Ltd.) and 27.0 parts of hydrobromic acid (Wako pure chemical industries, Ltd.) under a nitrogen atmosphere, and the mixture was stirred at 50 ℃ for 5 hours. After the reaction, acetic acid and hydrobromic acid were distilled off by an evaporator. The organic layer was separated by liquid separation using ethyl acetate and water, and then the organic layer was concentrated to obtain 9.0 parts of the compound represented by formula (1B-3). The yield thereof was found to be 98%.

And (3) identification: (Mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +366.2

Exact Mass (Exact Mass): +365.13

[ example 2]

7.0 parts of the compound represented by the formula (1B-3) and 1.0 part of 3, 4-dihydroxy-3-cyclobutene-1, 2-dione (manufactured by Wako pure chemical industries, Ltd.) were dissolved in 70 parts of 1-butanol (manufactured by Kanto chemical Co., Ltd.) and 49 parts of toluene (manufactured by Kanto chemical Co., Ltd.) and stirred at 110 ℃ for 3 hours. After completion of the reaction, 49 parts of hexane was added to precipitate a solid, and then the mixture was filtered by suction to obtain a solid. The obtained solid was dried under reduced pressure at 60 ℃ for 12 hours to obtain 4.0 parts of a compound represented by the formula (1B-4). The yield thereof was found to be 27%.

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +809.2

Exact Mass (Exact Mass): +808.23

[ example 3]

1.0 part of the compound represented by the formula (1B-4) was added to 6.0 parts of methanol to prepare a liquid (solution 3) in which the compound represented by the formula (1B-4) was dissolved. Further, a liquid (solution 4) was prepared by dissolving 7.5 parts of barium chloride dihydrate (manufactured by Wako pure chemical industries, Ltd.) in 20 parts of water, and the solution 4 was slowly added to the solution 3 at room temperature, followed by stirring for 30 minutes. After the reaction was completed, the solid obtained by suction filtration was washed with water and acetone. Drying was carried out at 60 ℃ under reduced pressure for 12 hours to obtain 1.0 part of the compound represented by the formula (1B-5). The yield thereof was found to be 75%.

[ example 4]

1.3 parts of a compound represented by formula (1B-6) was obtained in the same manner as in example 3, except that 10.6 parts of aluminum sulfate tetradecaheptadec hydrate (manufactured by Wako pure chemical industries, Ltd.) was used in example 3 instead of barium chloride dihydrate. The yield thereof was found to be 99%.

(Synthesis example 10)

In synthesis example 8, 9.9 parts of a compound represented by formula (1B-7) was obtained in the same manner as in synthesis example 8, except that 8.0 parts of 3-bromophenol (manufactured by tokyo chemical industries, ltd.) was used instead of 1-bromo-3, 5-dimethoxybenzene. The yield thereof was found to be 52%.

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +350.5

Exact Mass (Exact Mass): 349.13

[ example 5]

5.7 parts of a compound represented by the formula (1B-8) was obtained in the same manner as in example 2, except that 8.0 parts of the compound represented by the formula (1B-7) was used in place of the compound represented by the formula (1B-3) in example 2. The yield thereof was found to be 68%.

And (3) identification: (Mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +777.5

Exact Mass (Exact Mass): +776.2

[ example 6]

0.7 parts of a compound represented by the formula (1B-9) was obtained in the same manner as in example 3, except that 1.0 part of the compound represented by the formula (1B-8) was used in place of the compound represented by the formula (1B-4) in example 3. The yield thereof was found to be 51%.

[ example 7]

In example 6, 0.7 part of a compound represented by formula (1B-10) was obtained in the same manner as in example 6, except that 2.3 parts of aluminum sulfate tetradecaheptadec hydrate (manufactured by wako pure chemical industries, ltd.) was used instead of barium chloride dihydrate. The yield thereof was found to be 52%.

[ example 8]

In example 6, 0.3 part of a compound represented by formula (1B-11) was obtained in the same manner as in example 6, except that 1.2 parts of magnesium chloride (manufactured by wako pure chemical industries, ltd.) was used instead of barium chloride dihydrate. The yield thereof was found to be 22%.

(Synthesis example 11)

20.0 parts of 1-bromo-3, 5-dimethoxybenzene (manufactured by Tokyo chemical industry Co., Ltd.), 11.2 parts of 2, 4-dimethylaniline (manufactured by Tokyo chemical industry Co., Ltd.), 10.3 parts of potassium hydroxide, 0.47 parts of bis (tri-tert-butylphosphine) palladium (0), and 0.30 parts of tetrabutylammonium bromide were dissolved in 200 parts of toluene (manufactured by Kanto chemical Co., Ltd.) and 20 parts of water under a nitrogen atmosphere, and the mixture was heated at 90 ℃ for 16 hours while stirring. After the reaction was completed, the organic solvent was distilled off by an evaporator to obtain 25 parts of the compound represented by formula (1C-1).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +258.2

Exact Mass (Exact Mass): +257.1

(Synthesis example 12)

25 parts of the compound represented by the formula (1C-1) and 19.0 parts of monomethyl succinyl chloride succinate (manufactured by Tokyo chemical industries, Ltd.) were dissolved in 250 parts of toluene (manufactured by Kanto Chemicals, Ltd.) under a nitrogen atmosphere, and the mixture was heated at 100 ℃ for 16 hours with stirring. After the reaction, water was added to separate an organic layer, which was concentrated by an evaporator and then purified by silica gel column chromatography to obtain 22 parts of a compound represented by formula (1C-2).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +372.2

Exact Mass (Exact Mass): +371.2

(Synthesis example 13)

21.0 parts of the compound represented by the formula (1C-2) was dissolved in 210 parts of dichloromethane (manufactured by Kanto chemical Co., Ltd.) under a nitrogen atmosphere, 280 parts of boron tribromide 1M dichloromethane solution (manufactured by Tokyo chemical Co., Ltd.) was added at 0 ℃ and then the temperature was raised to 10 ℃ and stirred for 6 hours. After the reaction was completed, water was added to separate an organic layer, which was dried over magnesium sulfate and concentrated by an evaporator to obtain a crude product B. The crude product B contained 49% of the compound represented by the formula (1C-3) and 34% of the compound represented by the formula (1C-3-1).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +344.2

Exact Mass (Exact Mass): +343.1 type (1C-3)

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +330.2

Exact Mass (Exact Mass): +329.1 formula (1C-3-1)

(Synthesis example 14)

23 parts of the crude product B was added to 200 parts of methanol (manufactured by kanto chemical corporation) under a nitrogen atmosphere, cooled to 0 ℃, and 18 parts of thionyl chloride was added dropwise. After the completion of the dropwise addition, the temperature was raised to room temperature, and the mixture was stirred for 5 hours. After the reaction, water was added to separate an organic layer. The reaction mixture was dried over magnesium sulfate, the solvent was distilled off by an evaporator, and the product was separated and purified by silica gel column chromatography to obtain 16 parts of a compound represented by formula (1C-3).

(Synthesis example 15)

16.0 parts of the compound represented by the formula (1C-3) was dissolved in 160 parts of tetrahydrofuran (manufactured by Kanto chemical Co., Ltd.) under a nitrogen atmosphere, cooled to 0 ℃ and then 140 parts of a borane-1M tetrahydrofuran solution (manufactured by Tokyo chemical industry Co., Ltd.) was added dropwise. After the dropwise addition, the temperature is raised to 20 ℃ and the mixture is stirred for 5 hours. After water was added, the organic layer was separated, concentrated over magnesium sulfate, and then the solvent was distilled off by an evaporator and separated and purified by silica gel column chromatography to obtain 6 parts of a compound represented by formula (1C-4).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +330.3

Exact Mass (Exact Mass): +329.2

(Synthesis example 16)

5 parts of the compound represented by the formula (1C-4) was dissolved in 5 parts of tetrahydrofuran (manufactured by Kanto chemical Co., Ltd.), 20 parts of an ammonia 4M methanol solution was added, and the mixture was heated in an autoclave at 60 ℃ for 48 hours with stirring. After the reaction, the solvent was concentrated by an evaporator and separated and purified by silica gel column chromatography to obtain 3 parts of a compound represented by formula (1C-5).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +315.2

Exact Mass (Exact Mass): +314.2

[ example 9]

3 parts of a compound represented by the formula (1C-5) and 0.5 part of 3, 4-dihydroxy-3-cyclobutene-1, 2-dione (manufactured by Wako pure chemical industries, Ltd.) were dissolved in 20 parts of toluene (manufactured by Kanto chemical Co., Ltd.) and 5 parts of 1-butanol (manufactured by Kanto chemical Co., Ltd.) under a nitrogen atmosphere, and the mixture was heated at 120 ℃ for 2 hours while stirring. After the reaction was completed, the solvent was distilled off by an evaporator, 40 parts of tetrahydrofuran was added thereto, and after stirring for 1 hour, filtration and drying were performed to obtain 2.4 parts of a compound represented by formula (1C-6).

And (3) identification: (mass analysis) ionization mode ═ ESI +: m/z ═ M + H ] +707.4

Exact Mass (Exact Mass): +706.3

(resin Synthesis example 1)

An appropriate amount of nitrogen was passed through a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and replaced with a nitrogen atmosphere, and 371 parts of propylene glycol monomethyl ether acetate was added thereto and heated to 85 ℃ while stirring. Subsequently, 54 parts of acrylic acid and 225 parts of acrylic acid 3, 4-epoxytricyclo [5.2.1.0 ] were added dropwise over 4 hours^2,6]Decyl-8-yl ester and acrylic acid 3, 4-epoxy tricyclo [5.2.1.0^2,6]A mixture of decan-9-yl ester (mixing ratio 1:1), 81 parts of vinyltoluene (isomer mixture), 80 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution prepared by dissolving 30 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile), which is a polymerization initiator, in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After completion of the dropwise addition of the initiator solution, the flask was kept at 85 ℃ for 4 hours, and then cooled to room temperature to obtain a B-type copolymer (resin (B-1)) solution having a viscosity of 246 mPas (23 ℃) and a solid content of 37.5%. Weight average molecular weight of the resulting copolymerThe molecular weight Mw was 10600, the dispersity was 2.01, and the acid value of the solid content was 115 mg-KOH/g. The resin (B-1) has the following structural units.

(resin Synthesis example 2)

An appropriate amount of nitrogen was passed through a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and the atmosphere was replaced with nitrogen, and 280 parts of propylene glycol monomethyl ether acetate was added thereto and heated to 80 ℃ while stirring. Then, 38 parts of acrylic acid and 289 parts of acrylic acid 3, 4-epoxytricyclo [5.2.1.0 ] were added dropwise over 5 hours^2,6]Decyl-8-yl ester and acrylic acid 3, 4-epoxy tricyclo [5.2.1.0^2,6]A mixture of decan-9-yl esters (mixing ratio 1:1), 125 parts of propylene glycol monomethyl ether acetate. On the other hand, a mixed solution of 33 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the flask was kept at 80 ℃ for 4 hours, and then cooled to room temperature to obtain a B-type copolymer (resin (B-2)) solution having a viscosity (23 ℃) of 125 mPas and a solid content of 35.1%. The weight-average molecular weight Mw of the resulting copolymer was 9200, the dispersity was 2.08, and the acid value of the solid portion was 77 mg-KOH/g. The resin (B-2) has the following structural units.

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by 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

Solid component concentration of the liquid to be detected: 0.001 to 0.01% by mass

Injection amount: 50 μ L

A detector: RI (Ri)

Calibration standard substance: TSK STANDARD POLYSTYRENE (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 and the number average molecular weight in terms of polystyrene obtained above was defined as the degree of dispersion.

Preparation of Dispersion (P-1)

5 parts of the compound represented by the formula (1A-7), 5 parts of a dispersant, 4 parts (solid content) of the resin (B-1), 76 parts of propylene glycol monomethyl ether acetate and 10 parts of diacetone alcohol were mixed, 300 parts of zirconia beads having a diameter of 0.2 μm were put therein, and the mixture was shaken for 3 hours using a paint conditioner (manufactured by LAU) to remove the zirconia beads, thereby preparing a dispersion (P-1).

Dispersions (P-2) to (P-9) were prepared in the same manner as in the preparation of dispersion (P-1) with the compositions shown in Table 11.

[ Table 11]

In table 11, each component represents the following compound.

Colorant (A-1): a compound represented by the formula (1A-7)

Colorant (a-2): a compound represented by the formula (1B-4)

Colorant (a-3): a compound represented by the formula (1B-5)

Colorant (a-4): a compound represented by the formula (1B-6)

Colorant (a-5): a compound represented by the formula (1B-8)

Colorant (a-6): a compound represented by the formula (1B-9)

Colorant (a-7): a compound represented by the formula (1B-10)

Colorant (a-8): a compound represented by the formula (1B-11)

Colorant (a-9): a compound represented by the formula (1C-6)

Resin (B-1): resin (B-1) (conversion of solid content)

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

Solvent (E-2): diacetone alcohol

Dispersant (G-1): acrylic acid-based dispersant

Examples 10 to 18 and comparative example 1

[ preparation of colored resin composition ]

The respective components were mixed so as to have the compositions shown in table 12, to obtain colored resin compositions.

[ Table 12]

In table 12, each component represents the following compound.

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

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

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

Solvent (E-2): diacetone alcohol

Solvent (E-3): chloroform

Leveling agent (F-1): polyether modified Silicone oil ("TORAY SILICONE SH 8400" manufactured by DONGLIDAOCHANNING corporation)

< production of color Filter (colored coating film) 1 >

A colored resin composition was applied to a 5cm square glass substrate (Eagle 2000, manufactured by Corning corporation) by spin coating, and then baked at 100 ℃ for 3 minutes to obtain a colored coating film.

< determination of color >

The chromaticity of the colored coating film was determined as xy chromaticity coordinates (x, Y) and stimulus value Y in the XYZ color system of the CIE based on the spectral distribution measured by using a colorimeter (OSP-SP-200, manufactured by Olympus, ltd.) and the characteristic function of the C light source.

< evaluation of Heat resistance >

The obtained colored coating film was heated in an oven at 230 ℃ for 2 hours. The chromaticity was measured before and after heating, and based on the measured value, the mass ratio was measured in accordance with JIS Z8730: 2009(7. method for calculating color difference) the color difference Δ Eab was calculated, and the results are shown in table 13. Smaller Δ Eab means smaller color change. Further, when the heat resistance of the colored coating film is good, the heat resistance of a colored pattern made of the same colored resin composition is also considered to be good.

[ Table 13]

[ examples 19 to 25]

[ preparation of colored resin composition ]

The respective components were mixed so as to have the compositions shown in table 14, to obtain colored resin compositions.

[ Table 14]

In table 14, each component represents the following compound.

Polymerizable compound (C-1): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA, manufactured by Nippon Kagaku Co., Ltd.)

Polymerization initiator (D-1): n-acetoxy-1- (4-phenylmercaptophenyl) -3-cyclohexylpropane-1-one-2-imine (PBG-327, oxime Compound, manufactured by Changzhou powerful New electronic Material Co., Ltd.)

The other symbols represent the same ones as described above.

< production of color Filter (colored coating film) 2 and evaluation of Heat resistance >

A colored resin composition was applied onto a 5cm square glass substrate (Eagle 2000, manufactured by Corning Ltd.) by spin coatingAfter the compounding, the composition was prebaked at 100 ℃ for 3 minutes to form a colored composition layer. After leaving to cool, the colored composition layer formed on the substrate was exposed to 100mJ/cm in an atmosphere of an exposure machine (TME-150RSK, manufactured by Topukang Co., Ltd.)²The exposure amount (365nm basis) of (1) was irradiated with light. After the light irradiation, the resultant was postbaked at 230 ℃ for 30 minutes in an oven to obtain a colored coating film.

The measurement of the chromaticity was carried out before and after the postbaking, and based on the measurement value, the following measurement was carried out in accordance with JIS Z8730: 2009(7. method for calculating color difference) the color difference Δ Eab was calculated, and the results are shown in table 15.

[ Table 15]

Industrial applicability

According to the compound of the present invention, a color filter having excellent heat resistance can be formed.

Claims (5)

1. A compound represented by formula (IA):

in the formula (IA),

R¹～R⁴represents a hydrogen atom;

R⁵～R⁸each independently represents a hydrogen atom or a hydroxyl group, and is represented by R⁵～R⁸In the above formula, 2 to 4 are hydroxyl groups;

R^9Aand R^12AEach independently represents a compound having-CO₂ ^-A hydrocarbon group having 1 to 20 carbon atoms as a substituent;

R^10Aand R^11AEach independently represents an aromatic hydrocarbon group having 6 to 20 carbon atoms;

QAⁿ⁺represents an alkaline earth metal ion;

n represents an integer of 2 or more;

bA denotes QAⁿ⁺The number of (2);

in the reaction of R¹～R⁸And R^9A～R^12AIn the case where the total number of negative charges contained in (a) is kA, aA is (n × bA)/kA.

2. A colored resin composition comprising a colorant and a resin, the colorant comprising a compound represented by the formula (IA) according to claim 1.

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

4. A color filter formed from the colored resin composition according to claim 2 or 3.

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