JP7053448B2 - Colored resin composition, color filter and display device - Google Patents

Description

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

Color filters used in display devices such as liquid crystal displays, electroluminescence display devices and plasma displays, and solid-state image pickup devices such as CCDs and CMOS sensors are manufactured from colored resin compositions. As such a colored resin composition, a composition containing a compound represented by the following formula as a colorant is known (Patent Document 1).

Japanese Unexamined Patent Publication No. 2014-005451

The color filter formed from the above-mentioned colored resin composition known conventionally may not be sufficiently satisfactory in chemical resistance and contrast.

[1] Containing a colorant, a resin, a polymerizable compound and a polymerization initiator,
A colored resin composition in which the colorant contains a compound represented by the formula (1).

[In equation (1),
R ^101a to R ^101d and R ^102a to R ^102d each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent.
X ¹ and X ² are independently hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, and an aralkyl group which may have a substituent, respectively. Alternatively, it represents a group represented by the formulas (X1) to (X4).

R ²⁰¹ and R ⁴⁰¹ each independently have an alkyl group which may have a substituent, an aryl group which may have a substituent, and an alkoxy group or a substituent which may have a substituent. Represents an aryloxy group that may have.
R ³⁰¹ , R ³⁰² and R ⁵⁰¹ to R ⁵⁰³ each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent.
* In the formulas (X1) to (X4) represents a binding site with an oxygen atom.
The aromatic hydrocarbon ring constituting the aryl group, the aralkyl group, and the aryloxy group represented by X ¹ , X ² , R ²⁰¹ , and R ⁴⁰¹ may be coordinated with a metal atom. ]
[2] A color filter formed from the colored resin composition according to [1].
[3] A display device including the color filter according to [2].

The colored resin composition of the present invention can form a color filter having excellent chemical resistance.
Further, the colored resin composition of the present invention can form a color filter having excellent contrast.

The colored resin composition of the present invention includes a colorant (hereinafter, may be referred to as a colorant (A)), a resin (hereinafter, may be referred to as a resin (B)), and a polymerizable compound (hereinafter, a polymerizable compound (C)). ), And a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)).
In the colored resin composition of the present invention, the coloring agent contains a compound represented by the formula (1) (hereinafter, may be referred to as compound (1)).
The colored resin composition of the present invention preferably further contains a solvent (hereinafter, may be referred to as a solvent (E)).
The colored resin composition of the present invention may contain a leveling agent.
In the present specification, the compounds exemplified as each component may be used alone or in combination of a plurality of kinds unless otherwise specified.

<Colorant (A)>
The compound represented by the formula (1) contained in the colorant (A) is a tetraazaporphyrin compound, the central atom is a silicon atom, and at least one oxygen atom (preferably two oxygen atoms) is a silicon atom. It is a compound that is directly bound.

(In the formula (1), R ^101a to R ^101d and R ^102a to R ^102d each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent. ..
X ¹ and X ² are independently hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, and an aralkyl group which may have a substituent, respectively. Alternatively, it represents a group represented by the formulas (X1) to (X4).

R ²⁰¹ and R ⁴⁰¹ are independently an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or a substituent. Represents an aryloxy group which may have.
R ³⁰¹ , R ³⁰² and R ⁵⁰¹ to R ⁵⁰³ each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent.
* In the formulas (X1) to (X4) represents a binding site with an oxygen atom.
The aromatic hydrocarbon ring constituting the aryl group, the aralkyl group, and the aryloxy group represented by X ¹ , X ² , R ²⁰¹ , and R ⁴⁰¹ may be coordinated with a metal atom. )

As used herein, the term "alkyl group" includes linear, branched and cyclic groups. The same applies to the "alkoxy group".
Further, in the present specification, the "aryl group" represents a group consisting only of an unsubstituted aromatic hydrocarbon ring.

In the above formula (1), R ^101a to R ^101d and R ^102a to R ^102d are groups that bind to the tetraazaporphyrin skeleton.
The four groups R ^101a to R ^101d may be the same or different and are preferably the same, and the four groups R ^102a to R ^102d may be the same or different. Also, preferably the same.
The combinations of R ^101a and R ^102a , R ^101b and R ^102b , R ^101c and R ^102c , and R ^101d and R ^102d may be the same or different.
It is preferable that the combination of R ^101a and R ^102a , the combination of R ^101b and R ^102b , the combination of R ^101c and R ^102c , and the combination of R ^101d and R ^102d are the same.
Then, when the combination of R ^101a and R ^102a , the combination of R ^101b and R ^102b , the combination of R ^101c and R ^102c , and the combination of R ^101d and R ^102d are the same, the two groups in each combination The positional relationship is arbitrary, and compound (1) has four different types of isomers.
The above formula (1) means that all four types of isomers are included. Further, the tetraazaporphyrin compound may contain only one of these isomers, or may contain a plurality of types as a mixture.

R ^101a to R ^101d and R ^102a to R ^102d each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent.

Examples of the alkyl group which may have a substituent as R ^101a to R ^101d and R ^102a to R ^102d of the formula (1) include a linear, branched chain or cyclic alkyl group.
Examples of the linear, branched or cyclic alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-octyl. A linear alkyl group such as a group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group;
Isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-methylbutyl group, 1-methylbutyl group, neopentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, 4-methylpentyl group , 3-Methylpentyl group, 2-Methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1,3-dimethylbutyl group, 2,2-dimethylbutyl group , 1,2-dimethylbutyl group, 1,1-dimethylbutyl group, 3-ethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, 1,1,2-trimethylpropyl group, 1-ethyl-2-methylpropyl Group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 1-ethylpentyl group, 2,4-dimethylpentyl group, 2-ethylhexyl group, 2,5-dimethyl Hexyl group, 2,5,5-trimethylpentyl group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, 1,1-dimethylhexyl group, 3,5,5-trimethylhexyl group, 4 -Ethyloctyl group, 4-ethyl-4,5-dimethylhexyl group, 1,3,5,7-tetramethyloctyl group, 4-butyloctyl group, 6,6-diethyloctyl group, 6-methyl-4- Butyl octyl group, 3,5-dimethylheptadecyl group, 2,6-dimethylheptadecyl group, 2,4-dimethylheptadecyl group, 2,2,5,5-tetramethylhexyl group and other branched chain alkyl groups Cyclic alkyl groups (cycloalkyl groups) such as cyclopentyl group, cyclohexyl group, 1-cyclopentyl-2,2-dimethylpropyl group, 1-cyclohexyl-2,2-dimethylpropyl group;
The number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 15, further preferably 1 to 10, and even more preferably 1 to 5.
Among these, a linear or branched alkyl group having 1 to 10 carbon atoms is preferable, a linear or branched alkyl group having 1 to 5 carbon atoms is more preferable, and a tert-butyl group is further preferable. ..

Examples of the alkyl group having a substituent include those in which a part or all of the hydrogen atom of the alkyl group is substituted with halogen, and examples thereof include a chloromethyl group, a dichloromethyl group, a fluoromethyl group, and a trifluoromethyl group. Examples thereof include a group, a pentafluoroethyl group, a nonafluorobutyl group, a perfluorocyclobutyl group, a perfluorocyclopentyl group and the like.

Examples of the aryl group which may have a substituent as R ^101a to R ^101d and R ^102a to R ^102d in the formula (1) include a phenyl group, a nitrophenyl group, a cyanophenyl group, a hydroxyphenyl group and a carboxyphenyl group. , Methylphenyl group, dimethylphenyl group, trimethylphenyl group, fluorophenyl group, chlorophenyl group, bromophenyl group, methoxyphenyl group, ethoxyphenyl group, trifluoromethylphenyl group, N, N-dimethylaminophenyl group, naphthyl group, Examples thereof include nitronaphthyl group, cyanonaphthyl group, hydroxynaphthyl group, methylnaphthyl group, fluoronaphthyl group, chloronaphthyl group, bromonaphthyl group, trifluoromethylnaphthyl group and the like.
The aryl group has, for example, 6 to 20, preferably 6 to 18, more preferably 6 to 15, and even more preferably 6 to 10.

Further, in the formula (1), it is preferable that R ^102a to R ^102d are independently represented by the formula (R1).

(In the formula (R1), R ^601a to R ^601e independently have a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, and a substituent, respectively. Represents an aryl group which may have a substituent and an aryloxy group which may have a substituent, and * represents a binding site with a tetraazaporphyrin skeleton.)

As the alkyl group which may have a substituent as R ^601a to R ^601e in the formula (R1), even if it has the substituents mentioned as examples of R ^101a to R ^101d and R ^102a to R ^102d . A good alkyl group is mentioned.
As the aryl group which may have a substituent as R ^601a to R ^601e in the formula (R1), even if it has the substituents mentioned as examples of R ^101a to R ^101d and R ^102a to R ^102d . Good aryl groups are mentioned.
Specifically, a phenyl group, a nitrophenyl group, a cyanophenyl group, a hydroxyphenyl group, a carboxyphenyl group, a methylphenyl group, a dimethylphenyl group, a trimethylphenyl group, a fluorophenyl group, a chlorophenyl group, a bromophenyl group, a methoxyphenyl group, Ethoxyphenyl group, trifluoromethylphenyl group, N, N-dimethylaminophenyl group, naphthyl group, nitronaphthyl group, cyananonaphthyl group, hydroxynaphthyl group, methylnaphthyl group, fluoronaphthyl group, chloronaphthyl group, bromonaphthyl group, Examples thereof include a trifluoromethylnaphthyl group.

Examples of the alkoxy group which may have a substituent as R ^601a to R ^601e in the formula (R1) include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group and sec. -Butoxy group, tert-butoxy group, n-pentyloxy group, isopentyloxy group, neopentyloxy group, n-hexyloxy group, n-dodecyloxy group; cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group , Cyclohexyloxy group.

Assuming that a part or all of the hydrogen atom of the alkoxy group is substituted with halogen, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, 1, 1,2,2-Tetrafluoroethoxy group, 1,1,2-trifluoroethoxy group, 1,2,2-trifluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2-difluoroethoxy group Group, 1,2-difluoroethoxy group, 1,1-difluoroethoxy group, 2-fluoroethoxy group, 1-fluoroethoxy group, 2,2,3,3-tetrafluoro-1-propoxy group, 2,2 3,3,3-Pentafluoro-1-propoxy group, 2,2,3,3,4,4,4-heptafluoro-1-butoxy group, 2,2,3,4,4,4-hexafluoro -1-Butoxy group, 2,2,3,3,4,5,5-octafluoro-1-pentyloxy group, 3,3,4,4,5,5,6,6,6-nonafluoro -1-Hexyloxy group, 4,4,5,5,6,6,7,7,7-nonafluoro-1-heptyloxy group, 2,2,3,3,4,5,5,6 , 6,7,7-Dodecafluoro-1-heptyloxy group, 7,7,8,8,8-pentafluoro-1-octyloxy group, 3,3,4,4,5,5,6 , 7,7,8,8,8-Tridecafluoro-1-octyloxy group, 2,2,3,3,4,5,5,6,6,7,7,8,8,9 , 9-Hexadecafluoro-1-nonyloxy group, 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-1-nonyloxy group, 7,7 , 8,8,9,9,10,10,10-nonafluoro-1-decyloxy group, 3,3,4,4,5,5,6,6,7,7,8,8,9,9, 10,10,10-Heptadecafluoro-1-decyloxy group, 4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-1 -Deciloxy group, 7,7,8,8,9,9,10,10,11,11,12,12,12-Tridecafluoro-1-dodecyloxy group, 3,3,4,5,5 5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluoro-1-dodecyloxy group, 7,7,8,8,9, 9,10,10,11,11,12,12,13,13,14,14,14-heptadecafluoro-1-tetrade Syloxy group, 1H, 1H, 2,5-bis (trifluoromethyl) -3,6-dioxaundecafluoro-1-nonyloxy group, 6- (perfluoro-1-methylethyl) -1-hexyloxy group, 2- (Perfluoro-1-methylbutyl) -1-ethoxy group, 2- (perfluoro-3-methylbutyl) ethoxy group, 2- (perfluoro-7-methyloctyl) ethoxy group, 2H-hexafluoro-2-propoxy group, Examples thereof include 2,2-bis (trifluoromethyl) -1-propoxy group.

Examples of the aryloxy group which may have a substituent as R ^601a to R ^601e in the formula (R1) include an aryloxy group having 6 to 20 carbon atoms.
Specifically, a phenoxy group, a 1-naphthoxy group, a 2-naphthoxy group, a 2-methylphenoxy group, a 4-methylphenoxy group, a 4-tert-butylphenoxy group, a 2-methoxyphenoxy group, a 4-isopropylphenoxy group, etc. Can be mentioned.

The substituent in the aryloxy group which may have a substituent is not particularly limited, and is, for example, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, or a linear chain having 1 to 8 carbon atoms. Examples thereof include a state, a branched chain or cyclic alkoxy group, an amino group, a mono- or di-alkylamino group (the alkyl group has 1 to 8 carbon atoms), a halogen atom, a cyano group, a hydroxy group, a nitro group and the like.

Specific examples of the group represented by the formula (R1) include a phenyl group, a methylphenyl group, a dimethylphenyl group, a trimethylphenyl group, a fluorophenyl group, a chlorophenyl group, a bromophenyl group, a methoxyphenyl group, an ethoxyphenyl group, and a tri. Fluoromethylphenyl group and the like can be mentioned.

Further, it is preferable that at least one of R ^601a to R ^601e of the formula (R1) is a group other than a hydrogen atom.

Further, as the group represented by the formula (R1), at least one of R ^601a , R ^601c and R ^601e is independently a fluorine atom, a chlorine atom, a bromine atom, a methyl group or a trifluoromethyl group. Is preferable.

Specific examples include 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, and 2 , 6-Difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4,6-trifluorophenyl group, 2,3,5,6-tetrafluorophenyl group, 2,3 , 4, 5, 6-Phenyl group such as 6-pentafluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-Dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,4,6-trichlorophenyl group, 2,3,5,6-tetrachlorophenyl group, Phenyl group to which chlorine atom such as 2,3,4,5,6-pentachlorophenyl group is bonded, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2,3-dibromophenyl group, 2 , 4-dibromophenyl group, 2,5-dibromophenyl group, 2,6-dibromophenyl group, 3,4-dibromophenyl group, 3,5-dibromophenyl group, 2,4,6-tribromophenyl group, Phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4 -Methylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethyl Phenyl group to which an alkyl group such as phenyl group, 2,4,6-trimethylphenyl group, 2,3,5,6-tetramethylphenyl group, 2,3,4,5,6-pentamethylphenyl group is bonded, 2-Trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2,3-ditrifluoromethylphenyl group, 2,4-ditrifluoromethylphenyl group, 2,5-ditrifluoro Methylphenyl group, 2,6-ditrifluoromethylphenyl group, 3,4-ditrifluoromethylphenyl group, 3,5-ditrifluoromethylphenyl group, 2,4,6-tritrifluoromethylphenyl group, 2,3 5,6-Tetratrif Examples thereof include a phenyl group to which a fluorinated alkyl group such as a ruolomethylphenyl group and a 2,3,4,5,6-pentafluoromethylphenyl group is bonded.

Among these, a phenyl group, a 2-chlorophenyl group, and a 4-chlorophenyl group to which a fluorine atom such as a 2-fluorophenyl group, a 4-fluorophenyl group, a 2,4-difluorophenyl group, and a 2,6-difluorophenyl group are bonded , 2,4-Dichlorophenyl group, 2,6-dichlorophenyl group and other phenyl groups bonded with chlorine atoms, 2-bromophenyl group, 4-bromophenyl group, 2,4-dibromophenyl group, 2,6-dibromophenyl Phenyl group to which bromine atom such as group is bonded, 2-methylphenyl group, 4-methylphenyl group, 2,4-dimethylphenyl group, phenyl group to which alkyl group such as 2,6-dimethylphenyl group is bonded, 2- A phenyl group to which a fluorinated alkyl group such as a trifluoromethylphenyl group, a 4-trifluoromethylphenyl group, a 2,4-ditrifluoromethylphenyl group, or a 2,6-ditrifluoromethylphenyl group is bonded is preferable.

Examples of the aryl group which may have a substituent, which may have a substituent other than the group represented by the above formula (R1), include a naphthyl group, a nitronaphthyl group, a cyanonaphthyl group, a hydroxynaphthyl group and a methylnaphthyl group. Fluoronaphthyl group, chloronaphthyl group, bromonaphthyl group, trifluoromethylnaphthyl group and the like can be mentioned.

Of the groups attached to the tetraazaporphyrin skeleton, R ^101a to R ^101d are preferably linear or branched alkyl groups each independently which may have a substituent, and have 1 carbon atom. A linear or branched alkyl group of about 10 is preferable, and a linear or branched alkyl group having 1 to 5 carbon atoms is more preferable. In particular, it is preferable that all of R ^101a to R ^101d are tert-butyl groups.

Of the groups attached to the tetraazaporphyrin skeleton, it is preferable that R ^102a to R ^102d are independently represented by the above formula (R1). Further, when R ^102a to R ^102d are groups represented by the above formula (R1), at least one of R ^601a to R ^601e of the formula (R1) may be a group other than a hydrogen atom. Preferably, at least one of R ^601a , R ^601c and R ^601e is independently a fluorine atom, a chlorine atom, a bromine atom, a methyl group or a trifluoromethyl group, and more preferably, a fluorine atom is bonded. It is more preferable that it is a phenyl group, and it is particularly preferable that all of R ^102a to R ^102d are 2-fluorophenyl groups.

In the tetraazaporphyrin compound represented by the above formula (1), the central atom is Si, and two O (oxygen atoms) are bonded to Si as an axial ligand, and X ¹ or X is attached to each O. It has a structure in which ^two are combined.
Hereinafter, an example of a preferable structure of X ¹ and X ² , which is a part of the structure of the axial ligand, will be described.
X ¹ and X ² may be the same group or different groups.

X ¹ and X ² are independently hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, and an aralkyl group which may have a substituent, respectively. Alternatively, it represents a group represented by the following formulas (X1) to (X4).
* In the formulas (X1) to (X4) is a binding site with an oxygen atom.

R ²⁰¹ and R ⁴⁰¹ are independently an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or a substituent. Represents an aryloxy group that may have
R ³⁰¹ , R ³⁰² and R ⁵⁰¹ to R ⁵⁰³ each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent.

Examples of the alkyl group which may have a substituent as X ¹ or X ² and the aryl group which may have a substituent include R ^101a to R ^101d and R ^102a to R ^102d . Examples thereof include an alkyl group which may have a group and an aryl group which may have a substituent.
As the aralkyl group which may have a substituent as X ¹ or X ² , an arcandyl group having 1 to 5 carbon atoms such as a methylene group, an ethylene group and a propylene group is bonded to the group described as the above aryl group. Examples include the groups that have been used.

R ²⁰¹ in the formula (X1) has an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or a substituent. Represents an aryloxy group that may be used. The number of carbon atoms of the alkyl group representing R ²⁰¹ is preferably 1 to 20, more preferably 5 to 20, and even more preferably 5 to 15. The aryl group representing R ²⁰¹ has, for example, 6 to 20, preferably 6 to 18, more preferably 6 to 15, and even more preferably 6 to 10.

The alkyl group which may have a substituent and the aryl group which may have a substituent include the substituents mentioned as examples of R ^101a to R ^101d and R ^102a to R ^102d . Examples thereof include an alkyl group which may have a substituent and an aryl group which may have a substituent.
The alkoxy group which may have a substituent and the aryloxy group which may have a substituent may have the substituents listed as R ^601a to R ^601e of the formula (R1). Examples thereof include an alkoxy group and an aryloxy group which may have a substituent.

As R ²⁰¹ in the formula (X1), an alkyl group which may be substituted, an aryl group which may be substituted is preferable, a linear or branched alkyl group, a phenyl group which may be substituted, and the like. Substituted cyclopentadienyl anions are more preferred, such as 1-ethylpentyl group, phenyl group, 3-nitrophenyl group, 4-carboxyphenyl group, 3-carboxyphenyl group, 4-hydroxyphenyl group, ferrocene and the like. Is even more preferable.

R ³⁰¹ and R ³⁰² in the formula (X2) independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent.
The alkyl group which may have a substituent and the aryl group which may have a substituent include the substituents mentioned as examples of R ^101a to R ^101d and R ^102a to R ^102d . Examples thereof include an alkyl group which may have a substituent and an aryl group which may have a substituent.

R ⁴⁰¹ in the formula (X3) has an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or a substituent. Represents an aryloxy group that may be used.
The alkyl group which may have a substituent and the aryl group which may have a substituent include the substituents mentioned as examples of R ^101a to R ^101d and R ^102a to R ^102d . Examples thereof include an alkyl group which may have a substituent and an aryl group which may have a substituent.
The alkoxy group which may have a substituent and the aryloxy group which may have a substituent may have the substituents listed as R ^601a to R ^601e of the formula (R1). Examples thereof include an alkoxy group and an aryloxy group which may have a substituent.

R ⁵⁰¹ to R ⁵⁰³ in the formula (X4) each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent.
The alkyl group which may have a substituent and the aryl group which may have a substituent include the substituents mentioned as examples of R ^101a to R ^101d and R ^102a to R ^102d . Examples thereof include an alkyl group which may have a substituent and an aryl group which may have a substituent.
Among them, R ⁵⁰¹ to R ⁵⁰³ in the formula (X4) are preferably alkyl groups which may independently have a substituent, and more preferably an alkyl group having 1 to 5 carbon atoms. It is more preferably a methyl group or an ethyl group.

The aryl group which may have a substituent in X ¹ and X ² is preferably a group represented by the following formula (2).

R ⁷⁰¹ in the formula (2) is CO ₂ R ^701a , an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, a halogen atom, a nitro group, a cyano group, a hydroxyl group, and the like. Represents an alkyl group which may have a substituent (for example, a halogen atom) or a nitrogen atom-containing heterocyclic group, n represents an integer of 0 to 5, and R ^701a has a hydrogen atom and a substituent. It represents an alkyl group which may be present or an aryl group which may have a substituent, and * represents a bonding site with an oxygen atom. When n is an integer of 2 or more, the plurality of R ^701s may be the same or different.

Further, in the tetraazaporphyrin compound, in the formula (1), either one of X ¹ and X ² may be a group represented by the formula (2), and the other may be the other group.

N in the equation (2) is an integer of 0 to 5. When n is 0, the formula (2) represents a phenyl group.
When n is an integer of 2 or more, the plurality of R ^701s may be the same or different.
When n is 1, the position of R ⁷⁰¹ is preferably the p-position with respect to the binding site * with the oxygen atom.

When R ⁷⁰¹ is an alkoxy group which may have a substituent or an aryloxy group which may have a substituent, it has an alkoxy group which may have a substituent and a substituent. Examples of the aryloxy group which may be used include an alkoxy group which may have the substituents listed as R ^601a to R ^601e of the formula (R1) and an aryloxy group which may have a substituent. ..

When R ⁷⁰¹ is an alkyl group which may have a substituent, the alkyl group which may have a substituent includes the substituents mentioned as examples of R ^101a to R ^101d and R ^102a to R ^102d . Examples thereof include an alkyl group which may have.

The nitrogen atom-containing heterocyclic group is preferably a piperazinyl group, a piperidinyl group, a pyrrolidinyl group, an imidazolidinyl group, a pyrazoridinyl group or the like, and a piperazinyl group is more preferable.

When R ⁷⁰¹ is CO ₂ R ^701a , when R ^701a is a hydrogen atom, CO ₂ R ^701a represents a carboxyl group, and R ^701a has an alkyl group or a substituent which may have a substituent. CO ₂ R ^701a represents an acyloxycarbonyl group as an aryl group which may be present.
When R ^701a is an alkyl group which may have a substituent or an aryl group which may have a substituent, it has an alkyl group which may have a substituent and a substituent. Examples of the aryl group which may be used include an alkyl group which may have a substituent which is mentioned as an example of R ^101a to R ^101d and R ^102a to R ^102d , and an aryl group which may have a substituent. Be done.

Among these groups, the groups represented by the formula (2) are 4-carboxyphenyl group, phenyl group, 3-hydroxyphenyl group, 3,5-dihydroxyphenyl group, 3,5-difluorophenyl group, and the like. 4-Piperazinylphenyl group, 3,5-dimethyl-4-hydroxyphenyl group, 3,5,6-trimethyl-4-hydroxyphenyl group, 4-t-butylphenyl group, 3-nitrophenyl group, 3- Carboxyphenyl group, 4-cyanophenyl group, 4-trifluoromethylphenyl group are more preferable, 4-carboxyphenyl group, 3,5-difluorophenyl group, 3,5,6-trimethyl-4-hydroxyphenyl group, 4 -T-Butylphenyl group, 3-carboxyphenyl group, 4-cyanophenyl group and 4-trifluoromethylphenyl group are particularly preferable.

The aromatic hydrocarbon ring constituting the aryl group, the aralkyl group, and the aryloxy group represented by X ¹ , X ² , R ²⁰¹ , and R ⁴⁰¹ may be coordinated with a metal atom.
The aromatic hydrocarbon ring is, for example, a benzene ring, a naphthalene ring, a cyclopentadienyl anion ring, or the like, and is preferably a cyclopentadienyl anion ring.
The metal atom may be Fe, Cu, Cr, Co or the like, and Fe is preferable.
Coordination to a metal atom means that a sandwich-type metal complex may be formed together with an aromatic hydrocarbon ring.

In the formula (1), X ¹ and X ² are a hydrogen atom, an aryl group which may have a substituent, an aralkyl group which may have a substituent, and the formula (X1). A group represented by a group (preferably an alkyl group in which R ²⁰¹ may have a substituent, an aryl group in which R 201 may have a substituent) and a group represented by the formula (X4) (preferably R ⁵⁰¹ to R ⁵⁰³ is preferably an alkyl group which may have a substituent), and both independently have a hydrogen atom, an aryl group which may have a substituent, and a substituent. It may be an aralkyl group, a group represented by the formula (X1) (preferably an alkyl group in which R ²⁰¹ may have a substituent, an aryl group which may have a substituent), or a group of the formula (X4). It is more preferably a group represented by (preferably an alkyl group in which R ⁵⁰¹ to R ⁵⁰³ may have a substituent).

Further, in the formula (1), at least one of the aryl groups which may have the substituents of X ¹ and X ² is preferably a group represented by the formula (2), and both of them are each. It is more preferable that the group is independently represented by the formula (2).

In the formula (1), both X ¹ and X ² have a hydrogen atom, an unsubstituted aryl group, an aryl group having a carboxyl group, an aryl group having a hydroxyl group, an aryl group having a halogen atom, and a nitrogen atom-containing heterocycle. An aryl group having an aryl group, an aryl group having an alkyl group, an aryl group having a nitro group, an aryl group having a cyano group, an aryl group having an alkyl group and a hydroxyl group, CF _3- , CF ₃ CF _2- , or CF ₃ CF ₂ CF. It is represented by the formula (X1) in which an aryl group having ₂ −, an aralkyl group forming a sandwich-type metal complex together with an aromatic hydrocarbon ring and a metal atom, and R ²⁰¹ is a linear or branched alkyl group. A group represented by the formula (X1) in which R ²⁰¹ is an aryl group having a carboxyl group or a nitro group, a group represented by the formula (X1) in which R ²⁰¹ is an unsubstituted aryl group, and R ²⁰¹ are aromatic. A group represented by the formula (X1), which is an aryl group forming a sandwich-type metal complex together with a group hydrocarbon ring and a metal atom, and R ⁵⁰¹ to R ⁵⁰³ are linear or branched alkyl groups. It is more preferable that the group is represented by X4).
4-Carboxyphenylcarbonyl group, trimethylsilyl group, 4-carboxyphenyl group, 1-ethylpentylcarbonyl group, phenyl group, phenylcarbonyl group, 3-nitrophenylcarbonyl group, 3-carboxyphenylcarbonyl group, 3-hydroxyphenyl group, 3,5-Dihydroxyphenyl group, 3,5-difluorophenyl group, 4-piperazinylphenyl group, 3,5-dimethyl-4-hydroxyphenyl group, 3,5,6-trimethyl-4-hydroxyphenyl group, Particularly preferably, it is a ferrocenemethyl group, a ferrocenecarbonyl group, a 4-t-butylphenyl group, a 3-nitrophenyl group, a 3-carboxyphenyl group, a 4-cyanophenyl group, or a 4-trifluoromethylphenyl group.
4-carboxyphenyl carbonyl group, trimethylsilyl group, 4-carboxyphenyl group, 3,5-difluorophenyl group, 3,5,6-trimethyl-4-hydroxyphenyl group, 4-t-butylphenyl group, 3-carboxyphenyl A group, 4-cyanophenyl group, 4-trifluoromethylphenyl group or phenyl group is particularly preferable.
When X ¹ and X ² are the above groups, the formed color filter not only has excellent chemical resistance, but also exhibits high contrast.
As X ¹ and X ² exhibiting high contrast, an aryl group which may have a substituent, R ²⁰¹ is an aryl group which forms a sandwich type metal complex together with an aromatic hydrocarbon ring and a metal atom (X 1). ) Is preferable, and a phenyl group, a 4-carboxyphenyl group, a 3-carboxyphenyl group, a 4-cyanophenyl group, a 4-trifluoromethylphenyl group, and a ferrocenecarbonyl group are more preferable.

The compound represented by the formula (1) is usually a compound that absorbs orange light in the vicinity of 590 nm, but its absorption maximum wavelength (λmax) is preferably 570 to 620 nm.
The absorption maximum wavelength of the compound represented by the formula (1) can be changed by changing the substituent attached to the tetraazaporphyrin skeleton of the compound represented by the formula (1). Further, the preferable upper limit value of the absorption maximum wavelength is 620 nm, and the more preferable upper limit value is 615 nm. Further, the preferable lower limit value of the absorption maximum wavelength is 570 nm, and the more preferable lower limit value is 575 nm. The absorption maximum wavelength can be measured by a spectrophotometer.

The compound represented by the formula (1) has a particularly sharp absorption spectrum including the skirt portion, but is absorbed in the absorption spectrum as an index of having a particularly sharp absorption spectrum including the skirt portion. It is preferable that the wavelength width from the rising wavelength of the baseline on the long wavelength side of the maximum wavelength to the absorption maximum wavelength is 40 nm or less, and the half-value width at the absorption maximum wavelength is 20 nm or less.
The rising wavelength of the baseline is defined as a wavelength at which the absorbance at the long wavelength side is 0.01 or more when the absorbance at the absorption maximum wavelength is 1.
Then, the distance (wavelength width) from the rising wavelength to the absorption maximum wavelength is obtained.
In the present specification, the full width at half maximum is the full width at half maximum, and is formed by a straight line parallel to the horizontal axis subtracted by a value of 1/2 of the absorption coefficient value at the absorption maximum wavelength in the absorption spectrum and the peak. It is expressed as the distance (nm) between two intersections.

Further, it is preferable that the compound represented by the formula (1) is a group in which at least one of X ¹ and X ² is represented by the formula (2) in the formula (1).
If at least one of X ¹ and X ² is a group represented by the formula (2), fluorescence emission from the compound represented by the formula (1) can be suppressed, which is unnecessary to affect the color tone. The generation of light is prevented.
The fluorescence intensity can be evaluated by measuring the fluorescence spectrum using the absorption maximum wavelength as the excitation wavelength using a fluorescence spectrophotometer, and it is preferable that the fluorescence intensity is weak.

The compound represented by the formula (1) can be obtained by the following procedure.
First, the diiminoisopyrrole derivative represented by the following formula (5) is obtained from the cis form of the 1,2-dicyanoethylene compound represented by the following formula (4).
As a method for obtaining a cis form of the 1,2-dicyanoethylene compound represented by the formula (4), the method described in JP-A-11-043619 can be used, and the diiminoisopyrrole derivative represented by the formula (5) can be used. As the method for obtaining the above, the method described in JP-A-02-000665 can be used.

(In formulas (4) and (5), R ¹⁰¹ and R ¹⁰² each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent. Specific examples thereof include an alkyl group which may have a substituent and an aryl group which may have a substituent as examples of R ^101a to R ^101d and R ^102a to R ^102d .)

Subsequently, the diiminoisopyrrole derivative represented by the formula (5) is mixed with a Si source (for example, SiCl ₄ ) and heated for a cyclization reaction, and hydrolyzed to have Si as the central atom and Si. A compound in which the axial ligand of the above is an OH group (a compound in which both X ¹ and X ² in the formula (1) are H) is obtained.

X ¹ and X ² can be substituted from a hydrogen atom with another substituent by a method such as adding a compound having a structure for which the axial ligand is desired to be substituted to the compound obtained above and refluxing the compound. can.
For example, the addition of carboxylic acids and phenols causes dehydration condensation between the carboxy group or phenolic hydroxy group and the OH group of the axial ligand of Si, and X ¹ and X ² are separated from the hydrogen atom. Can be substituted with a substituent of.
Alternatively, X ¹ and X ² may be replaced with a silyl group from a hydrogen atom by adding a silylating agent.

Examples of the carboxylic acid and phenol used for the above substitution include aliphatic carboxylic acid, aromatic carboxylic acid, phenol and hydroxycarboxylic acid.
Specific examples thereof include benzoic acid, hydroxybenzoic acid, nitrobenzoic acid, terephthalic acid, isophthalic acid, phenol, ethylcaproic acid and the like.
Examples of the silylating agent include N, O-bis (trimethylsilyl) acetamide, trimethylchlorosilane and the like.

The content of the compound represented by the formula (1) is preferably 0.1% by mass or more and 50% by mass or less, and 0.5% by mass or more and 50% by mass or less, based on the total amount of the colorant (A). It is more preferable that it is 1% by mass or more and 50% by mass or less.

The content of the compound represented by the formula (1) is preferably 0.2% by mass or more and 20% by mass or less, and 0.5% by mass or more and 15% by mass or less with respect to the total solid content. Is more preferable, and it is further preferable that it is 1% by mass or more and 12% by mass or less.
The content of the colorant (A) is preferably 5% by mass or more and 60% by mass or less, more preferably 8% by mass or more and 55% by mass or less, and 10% by mass or more with respect to the total solid content. It is more preferably 50% by mass or less.
Here, the "total amount of solid content" in the present specification means an amount obtained by subtracting the content of the solvent from the total amount of the colored resin composition. The total amount of solid content and the content of each component thereof can be measured by a known analytical means such as, for example, liquid chromatography or gas chromatography.

The colored resin composition of the present invention contains, as the colorant (A), a compound represented by the formula (1) and a colorant other than the compound (1) (hereinafter, may be referred to as a colorant (A1)). You may. The colorant (A1) may contain one kind or two or more kinds of colorants.

The colorant (A1) may be a dye or a pigment. Examples of the dye include known dyes described in the Color Index (published by The Society of Dyers and Colorists) and Dyeing Note (Dyeing Co., Ltd.). According to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridin dyes, styryl dyes, coumarin dyes, quinoline. Examples thereof include dyes, nitro dyes and phthalocyanine dyes. Of these, organic solvent-soluble dyes are preferred. Two or more of these dyes may be used in combination.

Specific examples thereof include dyes having the following color index (CI) numbers. C. I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Reactive Yellow 2,76,116;
C. I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C. I. Disperse Yellow 51, 54, 76;
C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C. I. Reactive orange 16;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;
C. I. Acid Violet 34, 102;
C. I. Disperse Violet 26, 27;
C. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. Acid Blue 25, 27, 40, 45, 78, 80, 112;
C. I. Direct blue 40;
C. I. Disperse Blue 1, 14, 56, 60;
C. I. Solvent Green 1, 3, 5, 28, 29, 32, 33;
C. I. Acid Green 3, 5, 9, 25, 27, 28, 41;
C. I. Basic Green 1;
C. I. Bat green 1st prize.

As the pigment, known pigments can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists). Two or more types may be combined.
Specifically, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 202, 208, 209, 215, 216, 224, 242, 254, 255, 264, Red pigments such as 265, 266, 268, 269, 273, brominated diketopyrrolopyrrole;
C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet color pigments;
C. I. Pigment Green 7, 36, 58, 59 green pigments can be mentioned.

As the colorant (A1), a red pigment and a yellow pigment are preferable, and C.I. I. Pigment Red, 177, 179, 202, 208, 242, 254, 269, C.I. I. Pigment Yellow 138, 139, 150, 185 and brominated diketopyrrolopyrrole are more preferred.

The colorant (A1) is, if necessary, treated with rosin, surface-treated with a colorant derivative having an acidic group or a basic group introduced therein, grafted with a polymer compound or the like onto the surface of a pigment or the like, and sulfate fine particles. It may be subjected to atomization treatment by a chemical conversion method or the like, cleaning treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method or the like. It is preferable that the particle size of the pigment or the like is substantially uniform. The colorant (A1) is uniformly dispersed in the dispersion liquid by containing the dispersant and performing the dispersion treatment.

Examples of the dispersant include a surfactant and the like, and any of a cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples thereof include polyester-based, polyamine-based and acrylic-based surfactants. As another dispersant, the resin (B) described later may be used. These dispersants may be used alone or in combination of two or more. Dispersants include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), and EFKA (registered trademark). (BASF), Azisper (registered trademark) (Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (Big Chemie), BYK (registered trademark) (Big Chemie) and the like.

When a dispersant is used, the amount of the dispersant used is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less, based on 100 parts by mass of the colorant (A1). When the amount of the dispersant used is within the above range, a more uniform dispersed colorant (A1) -containing liquid tends to be obtained.

The content of the colorant (A1) in the colored resin composition is usually 0% by mass or more and 50% by mass or less, preferably 0% by mass or more and 40% by mass or less, and more preferably. It is 0% by mass or more and 30% by mass or less.

<Resin (B)>
The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (a) (hereinafter, “(a)”). A resin having a structural unit derived from) is more preferable. The resin (B) is a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, may be referred to as “(b)”). Structural units derived from the monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)"), and sides. It is preferable to have at least one structural unit selected from the group consisting of structural units having an ethylenically unsaturated bond in the chain.

Specifically, as (a), for example, acrylic acid, methacrylic acid, maleic anhydride, itaconic acid anhydride, 3,4,5,6-tetrahydrophthalic acid anhydride;
Examples thereof include succinic acid mono [2- (meth) acryloyloxyethyl], and acrylic acid, methacrylic acid, and maleic anhydride are preferable.
In addition, in this specification, "(meth) acrylic acid" represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth) acryloyl" and "(meth) acrylate" have the same meaning.

As (b), a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxylan ring, an oxetane ring and a tetrahydrofuran ring) and a (meth) acryloyloxy group is preferable. ..
Examples of (b) include glycidyl (meth) acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate, and 3-ethyl-3-. (Meta) acryloyloxymethyloxetane, tetrahydrofurfuryl (meth) acrylate and the like can be mentioned, and glycidyl (meth) acrylate, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (preferably). Meta) acrylate, 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 ^2,6 ] decane-8. -Il (meth) acrylate benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene and the like, preferably styrene, Vinyl toluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, 2-hydroxyethyl (meth) acrylate and the like are preferable.

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

The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. ..
The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.

The acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and even more preferably 70 to 135 mg-KOH / g in terms of solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution. ..

The content of the resin (B) is preferably 10 to 70% by mass, more preferably 15 to 65% by mass, and further preferably 20 to 60% by mass with respect to the total solid content.

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, which is preferable. Is a (meth) acrylic acid ester compound.

Above all, 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 tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (dipentaerythritol hexa). Meta) Acrylate and the like can be mentioned.

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

The content of the polymerizable compound (C) is preferably 3 to 60% by mass, more preferably 5 to 50% by mass, and further preferably 11 to 40% by mass with respect to the total solid content. ..

<Polymer Initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids and the like by the action of light or heat, and a known polymerization initiator can be used. Examples of the polymerization initiator that generates an active radical include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl). ) Octane-1-on-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-on-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-1,3,5-triazine, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole And so on.

The polymerization initiator is preferably a polymerization initiator containing at least one selected from the group consisting of a triazine compound, an acylphosphine oxide compound, an alkylphenone compound, an O-acyloxime compound and a biimidazole compound, and preferably contains an O-acyloxime compound. Polymerization initiators are more preferred.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is a mass part. When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, so that the productivity of the color filter is improved.

The content of the O-acyloxime compound is preferably 50% by mass or more, more preferably 80% by mass or more, still more preferably 90% by mass or more, based on the total amount of the polymerization initiator (D). Particularly preferably, it is 95% by mass or more. When the content of the O-acyloxime compound is within the above range, a color filter having high brightness tends to be produced even when the sensitivity and developability at the time of forming the coloring pattern and the content of the coloring agent are high.

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

<Polymerization initiation aid (D1)>
The polymerization initiator (D1) is a compound or a sensitizer used to promote the polymerization of the polymerizable compound initiated by the polymerization initiator. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).
Examples of the polymerization initiation aid (D1) include 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone, 9,10-dimethoxyanthracene, and 2,4-diethylthioxanthone. Examples thereof include N-phenylglycine.

When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is preferably 1 to 20 parts by mass. When the amount of the polymerization initiation aid (D1) is within this range, a coloring pattern can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.

The colored resin composition of the present invention preferably contains a solvent.

<Solvent (E)>
The solvent (E) is not particularly limited, and a solvent usually used in the art can be used. For example, an ester solvent (solvent containing -COO- in the molecule and not containing -O-), an ether solvent (solvent containing -O- in the molecule and not containing -COO-), an ether ester solvent (intramolecular). Solvent containing -COO- and -O-), Ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule, -O-,- CO- and -COO-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide and the like.

Examples of the solvent include ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate and γ-butyrolactone (intramolecular). Solvents containing -COO- and not -O-); ether solvents 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. (Solvent containing -O- and not -COO- in the molecule);
Ether ester solvents such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate (intramolecular-COO- Solvent containing -O-);
Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone, cyclohexanone (solvents containing -CO- and not -COO- in the molecule); butanol, cyclohexanol , Alcohol solvent such as propylene glycol (solvent containing OH in the molecule and not containing -O-, -CO- and -COO-); and the like. Examples thereof include aromatic hydrocarbon solvents such as toluene and xylene. Examples thereof include amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone.

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

The solvent is preferably a mixed solvent containing propylene glycol monomethyl ether acetate. As a solvent to be combined with propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol methyl ether acetate, 3-methoxybutyl acetate, 3- Preference is given to methoxy-1-butanol and 4-hydroxy-4-methyl-2-pentanone, propylene glycol monomethyl ether, dipropylene glycol methyl ether acetate, ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol and 3 -Ethyl ethoxypropionate is more preferred, and ethyl lactate, 4-hydroxy-4-methyl-2-pentanone and propylene glycol monomethyl ether are even more preferred.

The content of the solvent to be combined with propylene glycol monomethyl ether acetate is preferably 1% by mass or more and 50% by mass or less, more preferably 3% by mass or more and 40% by mass or less, and further preferably 5 with respect to the total amount of the solvent. It is by mass% or more and 30% by mass or less.

When the solvent (E) is contained, the content of the solvent (E) is preferably 20 to 80% by mass, more preferably 25 to 75% by mass, based on the total amount of the colored resin composition of the present invention. In other words, the total solid content of the colored resin composition is preferably 5 to 30% by mass, 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 is good, and the color density is not insufficient when the color filter is formed, so that the display characteristics tend to be good. ..

<Other ingredients>
The colored resin composition of the present invention is, if necessary, an addition known in the art such as a leveling agent, a filler, another polymer compound, an adhesion accelerator, an antioxidant, a light stabilizer, a chain transfer agent, and the like. It may contain an agent.

<Manufacturing method of colored resin composition>
The colored resin composition of the present invention is a mixture of a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E) and other components as necessary. Can be prepared by

<Manufacturing method of color filter>
Examples of the method for producing a colored pattern from the colored resin composition of the present invention include a photolithography method, an inkjet method, a printing method and the like. Of these, the photolithography method is preferable. In the photolithography method, a colored coating film which is a cured product of the colored resin composition layer can be formed by not using a photomask at the time of exposure and / or not developing the photomask. The colored pattern and the colored coating film thus formed are the color filters of the present invention.

The colored resin composition can produce a color filter having excellent chemical resistance and contrast. 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, an electronic paper, etc.) and a solid-state image sensor.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited by the following examples as well as the present invention, and appropriate modifications are made to the extent that it can meet the purposes of the preceding and the following. Of course, it is possible to carry out, and all of them are included in the technical scope of the present invention.

[Synthesis Example 1]
(Synthesis of diiminoisopyrrole derivative)
The compound represented by the formula (x) was obtained by the synthetic method described in Japanese Patent No. 3961078. Further, from the compound represented by the formula (x), a compound represented by the formula (y) was obtained in the same manner as in the synthesis method described in JP-A-02-000665.

[Synthesis Example 2]
Quinoline (20 ml) and SiCl ₄ (2.38 g) were charged into a reactor equipped with a cooling tube, a thermometer and a stirrer, and 2.45 g of the compound represented by the formula (y) was added at 120 ° C. to 150 ° C. Was reacted for 3 hours. The reaction mixture was poured into dilute hydrochloric acid at 80 ° C., the precipitate was filtered off, and washed with methanol to obtain 0.8 g of the compound represented by the formula (a-1).

[Synthesis Example 3]
A compound (2.0 g) represented by the formula (a-1), dimethylacetamide (10 ml), and terephthalic acid (1.5 g) were charged in a 25 ml reactor equipped with a cooling tube, a thermometer, and a stirrer for 2 hours. It was refluxed. After allowing to cool, the reaction solution was concentrated and purified by silica gel column chromatography to obtain 0.6 g of the compound represented by the formula (a-2).

[Synthesis Example 4]
A compound (1 g) represented by the formula (a-1), pyridine (3 ml), and N, O-bis (trimethylsilyl) acetamide (1 g) were charged into a reactor equipped with a cooling tube, a thermometer, and a stirrer. The mixture was stirred at 90 ° C. for 1 hour. The reaction solution was discharged into water, the precipitated solid was filtered off, and purified by silica gel column chromatography to obtain 0.5 g of the compound represented by the formula (a-3).

[Synthesis Example 5]
A compound (2.0 g) represented by the formula (a-1), mesitylene (10 ml), and 4-hydroxybenzoic acid (1.5 g) are charged in a 25 ml reactor equipped with a cooling tube, a thermometer, and a stirrer. It was refluxed for 2 hours. After allowing to cool, the reaction solution was concentrated and purified by silica gel column chromatography to obtain 1.2 g of the compound represented by the formula (a-4).

[Synthesis Example 6]
1.6 g of the compound represented by the formula (a-5) was obtained in the same manner except that 4-hydroxybenzoic acid in Synthesis Example 5 was changed to 2-ethylhexanoic acid.

[Synthesis Example 7]
1.0 g of the compound represented by the formula (a-6) was obtained in the same manner except that 4-hydroxybenzoic acid in Synthesis Example 5 was changed to phenol.

[Synthesis Example 8]
A compound (2.0 g) represented by the formula (a-1), mesitylene (10 ml), and benzoic acid (1.5 g) were charged in a 25 ml reactor equipped with a cooling tube, a thermometer, and a stirrer, and refluxed for 2 hours. I let you. After allowing to cool, the reaction solution was concentrated and purified by silica gel column chromatography to obtain 1.2 g of the compound represented by the formula (a-7).

[Synthesis Example 9]
In the same manner except that the benzoic acid in Synthesis Example 8 was changed to 3-nitrobenzoic acid (1.5 g), 1.4 g of the compound represented by the formula (a-8) was obtained.

[Synthesis Example 10]
0.5 g of the compound represented by the formula (a-9) was obtained in the same manner except that the benzoic acid in Synthesis Example 8 was changed to isophthalic acid and mesitylene was changed to dimethylacetamide.

[Synthesis Example 11]
From the compound represented by the formula (x), the compound represented by the formula (b-1) was obtained by the synthetic method described in Japanese Patent No. 3961078.

[Synthesis Example 12]
An appropriate amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the nitrogen atmosphere, 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 85 ° C. with stirring. Then 38 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] deca-8-ylacrylate and 3,4-epoxytricyclo [5.2.2.10 ^{2, 6} ] A mixed solution of 25 parts of a mixture of deca-9-ylacrylate (content ratio 1: 1), 137 parts of cyclohexylmaleimide, 50 parts of 2-hydroxyethylmethacrylate, and 338 parts of propylene glycol monomethyl ether acetate is added dropwise over 5 hours. bottom. On the other hand, a mixed solution prepared by dissolving 5 parts of 2,2-azobisisobutyronitrile in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropping, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to prepare a copolymer (resin (B-1)) solution having a B-type viscosity (23 ° C.) of 23 mPa · s and a solid content of 25.6%. Obtained. The weight average molecular weight Mw of the produced copolymer was 8000, the solid content acid value was 111 mg-KOH / g, and the dispersity was 2.1. The resin (B-1) has the following structural units.

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

[Synthesis Example 13]
A compound (0.20 g) represented by the formula (a-1), diglyme (5.5 g), and resorcinol (0.23 g) were charged in a 25 ml reactor equipped with a cooling tube, a thermometer, and a stirrer, and the temperature was 150 ° C. Was stirred for 2 hours. After allowing to cool, the reaction solution was added dropwise to 30 g of 20% saline solution, and the precipitated solid was collected by filtration and washed with water. The solid was dispersed and washed with water and then dried in a vacuum oven at 40 ° C. to obtain 0.23 g of the compound represented by the formula (a-10).

[Synthesis Example 14]
0.24 g of the compound represented by the formula (a-11) was obtained in the same manner except that resorcinol in Synthesis Example 13 was changed to phloroglucinol.

[Synthesis Example 15]
0.20 g of the compound represented by the formula (a-12) was obtained in the same manner except that resorcinol in Synthesis Example 13 was changed to 3,5-difluorophenol.

[Synthesis Example 16]
0.23 g of the compound represented by the formula (a-13) was obtained in the same manner except that resorcinol in Synthesis Example 13 was changed to 1- (4-hydroxyphenyl) piperazine.

[Synthesis Example 17]
0.20 g of the compound represented by the formula (a-14) was obtained in the same manner except that resorcinol in Synthesis Example 13 was changed to 2,6-dimethylhydroquinone.

[Synthesis Example 18]
0.21 g of the compound represented by the formula (a-15) was obtained in the same manner except that resorcinol in Synthesis Example 13 was changed to trimethylhydroquinone.

[Synthesis Example 19]
0.20 g of the compound represented by the formula (a-16) was obtained in the same manner except that resorcinol in Synthesis Example 13 was changed to hydroxymethylferrocene.

[Synthesis Example 20]
0.29 g of the compound represented by the formula (a-17) was obtained in the same manner except that resorcinol in Synthesis Example 13 was changed to ferrocenecarboxylic acid.

[Synthesis Example 21]
A compound (9.0 g) represented by the formula (a-1), toluene (20 ml), and 4-t-butylphenol (8.1 g) were charged in a 50 ml reactor equipped with a cooling tube, a thermometer, and a stirrer. The mixture was stirred at 100 ° C. for 3 hours. Purification with a silica gel column gave 6.3 g of the compound represented by the formula (a-18).

[Synthesis Example 22]
A compound (1.5 g) represented by the formula (a-1), toluene (20 ml), and 3-nitrophenol (2.8 g) were charged into a 50 ml reactor equipped with a cooling tube, a thermometer, and a stirrer, and 100 The mixture was stirred at ° C. for 0.5 hours. Purification with a silica gel column gave 1.0 g of the compound represented by the formula (a-19).

[Synthesis Example 23]
A compound (1.9 g) represented by the formula (a-1), toluene (10 ml), and 3-hydroxybenzoic acid (3.3 g) were charged in a 25 ml reactor equipped with a cooling tube, a thermometer, and a stirrer. The mixture was stirred under reflux for 0.5 hours. After releasing to water / ethyl acetate, the precipitate is filtered out, dissolved in N, N-dimethylformamide, and white clay and silica gel are added to treat the compound represented by the formula (a-20). I got 5g.

[Synthesis Example 24]
A compound (1.5 g) represented by the formula (a-1), toluene (15 ml), and 4-cyanophenol (3.0 g) were charged into a 50 ml reactor equipped with a cooling tube, a thermometer, and a stirrer, and 100 was charged. The mixture was stirred at ° C for 20 minutes. After cooling to room temperature, the insoluble material was removed by filtration and purified by a silica gel column to obtain 0.7 g of the compound represented by the formula (a-21).

[Synthesis Example 25]
A compound (1.5 g) represented by the formula (a-1), toluene (15 ml), and 4-trifluoromethylphenol (3.0 g) are charged in a 50 ml reactor equipped with a cooling tube, a thermometer, and a stirrer. , Stirred at 100 ° C. for 20 minutes. After cooling to room temperature, the insoluble material was removed by filtration and purified by a silica gel column to obtain 1.6 g of the compound represented by the formula (a-22).

[Synthesis Example 26]
The compound represented by the formula (c-1) was obtained by the synthetic method described in JP-A-2016-27075.

<Preparation of colored resin composition>
[Example 1]
A colored resin composition was obtained by mixing the following components.
Compound (1): Compound represented by the formula (a-1) Three-part resin (B): Resin (B-1) (in terms of solid content) 65-part polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD) (Registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 35 parts Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-on-2-imine (Irgacure (registered) Trademark) OXE01; manufactured by BASF; O-acyloxime compound) 7.0 parts Solvent (E): propylene glycol monomethyl ether acetate 501 parts
Ethyl lactate 38 parts Leveling agent (H): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.10 parts

[Example 2]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-2) was used instead of the compound represented by the formula (a-1).

[Example 3]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-3) was used instead of the compound represented by the formula (a-1).

[Example 4]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-4) was used instead of the compound represented by the formula (a-1).

[Example 5]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-5) was used instead of the compound represented by the formula (a-1).

[Example 6]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-6) was used instead of the compound represented by the formula (a-1).

[Example 7]
A colored resin composition is obtained in the same manner as in Example 1 except that the compound represented by the formula (a-7) is used instead of the compound represented by the formula (a-1).

[Example 8]
A colored resin composition is obtained in the same manner as in Example 1 except that the compound represented by the formula (a-8) is used instead of the compound represented by the formula (a-1).

[Example 9]
A colored resin composition is obtained in the same manner as in Example 1 except that the compound represented by the formula (a-9) is used instead of the compound represented by the formula (a-1).

[Preparation of dispersion liquid 1]
C. I. Pigment Red 254 (pigment) 14 parts, acrylic pigment dispersant 4.9 parts, resin (B-1) (solid content equivalent) 4.2 parts, propylene glycol monomethyl ether acetate 74 parts and ethyl lactate 2.5 parts. The mixture was mixed and the pigment was sufficiently dispersed using a bead mill to prepare a dispersion liquid 1.

[Example 10]
A colored resin composition was obtained by mixing the following components.
Compound (1): Compound represented by the formula (a-1) 5 parts Colorant (A1): Dispersion 1 422 parts Resin (B): Resin (B-1) (solid content equivalent) 40 parts polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 35 parts Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane- 1-ON-2-imine (Irgacure (registered trademark) OXE01; manufactured by BASF; O-acyloxime compound) 7.0 parts Solvent (E): propylene glycol monomethyl ether acetate 553 parts
Ethyl lactate 22 parts Leveling agent (H): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.10 parts

[Example 11]
A colored resin composition was obtained in the same manner as in Example 10 except that the compound represented by the formula (a-3) was used instead of the compound represented by the formula (a-1).

[Comparative Example 1]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (b-1) was used instead of the compound represented by the formula (a-1).

<Preparation of color filter (colored coating film) 1>
A colored resin composition was applied onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Inc.) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to form a colored resin composition layer. After allowing to cool, light was irradiated with an exposure amount of 60 mJ / cm ² (based on 365 nm) under an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). Then, in an oven, post-baking was performed at 230 ° C. for 20 minutes to obtain a color filter.

[Example 12]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-10) was used instead of the compound represented by the formula (a-1).

[Example 13]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-11) was used instead of the compound represented by the formula (a-1).

[Example 14]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-12) was used instead of the compound represented by the formula (a-1).

[Example 15]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-13) was used instead of the compound represented by the formula (a-1).

[Example 16]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-14) was used instead of the compound represented by the formula (a-1).

[Example 17]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-15) was used instead of the compound represented by the formula (a-1).

[Example 18]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-16) was used instead of the compound represented by the formula (a-1).

[Example 19]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-17) was used instead of the compound represented by the formula (a-1).

[Example 20]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-18) was used instead of the compound represented by the formula (a-1).

[Example 21]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-19) was used instead of the compound represented by the formula (a-1).

[Example 22]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-20) was used instead of the compound represented by the formula (a-1).

[Example 23]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-21) was used instead of the compound represented by the formula (a-1).

[Example 24]
A colored resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-22) was used instead of the compound represented by the formula (a-1).

[Example 25]
A colored resin composition was obtained by mixing the following components.
Compound (1): Compound represented by formula (a-1) Five-part colorant (A1): Compound represented by formula (c-1) 24 parts Resin (B): Resin (B-1) (solid) 40 parts polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 35 parts Polymerization initiator (D): N-benzoyloxy-1- ( 4-Phenylsulfanylphenyl) Octane-1-on-2-imine (Irgacure (registered trademark) OXE01; manufactured by BASF; O-acyloxime compound) 7.0 parts Solvent (E): propylene glycol monomethyl ether acetate 553 parts
Ethyl lactate 22 parts Leveling agent (H): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.10 parts

[Example 26]
A colored resin composition was obtained in the same manner as in Example 25 except that the compound represented by the formula (a-3) was used instead of the compound represented by the formula (a-1).

[Example 27]
A colored resin composition was obtained in the same manner as in Example 25 except that the compound represented by the formula (a-5) was used instead of the compound represented by the formula (a-1).

[Example 28]
A colored resin composition was obtained in the same manner as in Example 25 except that the compound represented by the formula (a-7) was used instead of the compound represented by the formula (a-1).

[Example 29]
A colored resin composition was obtained in the same manner as in Example 25 except that the compound represented by the formula (a-16) was used instead of the compound represented by the formula (a-1).

[Example 30]
A colored resin composition was obtained in the same manner as in Example 25 except that the compound represented by the formula (a-17) was used instead of the compound represented by the formula (a-1).

[Comparative Example 2]
A colored resin composition was obtained in the same manner as in Example 25 except that the compound represented by the formula (b-1) was used instead of the compound represented by the formula (a-1).

<Chemical resistance test>
Preparation of Color Filter The color filter obtained by the method 1 was immersed in N-methylpyrrolidone whose temperature was adjusted to 40 ° C. for 30 minutes. For the color filter before and after immersion, the spectral spectrum at a wavelength of 400 to 780 nm was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the rate of change in absorbance at the maximum absorption wavelength λmax (after immersion). Absorbance / absorbance before immersion) was calculated. The lower the rate of change in absorbance, the better the chemical resistance. The results are shown in Tables 1 and 2.

<Preparation of color filter (colored coating film) 2>
After applying the colored resin composition on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Inc.) by the spin coating method, a vacuum dryer (manufactured by VCD Microtech Co., Ltd.) is used to reach an ultimate pressure of 66 Pa. The colored resin composition layer was formed by drying under reduced pressure. After allowing to cool, light was irradiated with an exposure amount of 60 mJ / cm ² (based on 365 nm) under an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). Then, in an oven, post-baking was performed at 100 ° C. for 3 minutes to obtain a color filter.

<Contrast measurement>
Fabrication of color filter Regarding the color filter obtained by the method 2, contrast meter (CT-1; Tsubosaka Electric Co., Ltd., color difference meter BM-5A; Topcon Co., Ltd., light source; F-10, polarizing film; Tsubosaka The contrast was measured with a blank value of 30,000 using (manufactured by Denki Co., Ltd.). The results are shown in Tables 3 and 4. The contrast of the color filter tends to depend on the fluorescence intensity, and the lower the fluorescence intensity, the higher the contrast.

Claims (3)

Contains colorants, resins, polymerizable compounds and polymerization initiators
A colored resin composition in which the colorant contains a compound represented by the formula (1).

[In equation (1),
R ^101a to R ^101d each independently represent a tert-butyl group.
R ^102a to R ^102d each independently represent a group represented by the formula (R1) .

Each of R ^601a to R ^601e may independently have a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, and a substituent. It represents an aryloxy group which may have an aryl group or a substituent, and at least one of R ^601a , R ^601c , and R ^601e represents a fluorine atom, and * represents a binding site with a tetraazaporphyrin skeleton. show.
X ¹ and X ² each independently represent an aryl group which may have a substituent or a group represented by the formula (X1 ) .

R 201 represents an aryl group that forms ^a sandwich-type metal complex together with an aromatic hydrocarbon ring and a metal atom .
* In the formula (X1 ) represents a binding site with an oxygen atom.
The aromatic hydrocarbon ring constituting the aryl group represented by X ¹ and X ² may be coordinated to a metal atom. ] A color filter formed from the colored resin composition according to claim 1. A display device including the color filter according to claim 2.