KR102456389B1 - Colored resin composition, colored filter and display device - Google Patents

Abstract

As for the color filter formed from the conventionally known colored resin composition, chemical-resistance and contrast may not fully be satisfied. The present invention relates to a colored resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant comprising a compound represented by Formula (1), a color filter formed from the colored resin composition, and a display device. .

Description

Colored resin composition, color filter, and display device TECHNICAL FIELD

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

The color filter used for display apparatuses, such as a liquid crystal display device, an electroluminescent display device, and a plasma display, and solid-state imaging elements, such as a CCD and CMOS sensor, is manufactured from a colored resin composition. As such a colored resin composition, the composition containing the compound represented by a following formula as a coloring agent is known (patent document 1).

[Formula A]

Japanese Patent Application Laid-Open No. 2014-005451

The color filter formed from said colored resin composition known conventionally may not fully be able to satisfy|fill chemical-resistance and contrast.

[1] A colorant, a resin, a polymerizable compound, and a polymerization initiator are included,

The colored resin composition in which a coloring agent contains the compound represented by Formula (1).

[Formula 1]

[in formula (1),

R ^101a to R ^101d and R ^102a to R ^102d each independently represent an optionally substituted alkyl group or an optionally substituted aryl group.

X ¹ and X ² each independently represent a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an aralkyl group which may have a substituent, or a group represented by formulas (X1) to (X4) .

[Formula 3]

R ²⁰¹ and R ⁴⁰¹ each independently represent an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group or an optionally substituted aryloxy group.

R ³⁰¹ , R ³⁰² and R ⁵⁰¹ to R ⁵⁰³ each independently represent an optionally substituted alkyl group or an optionally substituted aryl group.

* in Formulas (X1) to (X4) represents a bonding site with an oxygen atom.

The aromatic hydrocarbon ring constituting the aryl group, aralkyl group, and aryloxy group represented by X ¹ , X ² , R ²⁰¹ , and R ⁴⁰¹ may be positioned at 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 this invention can form the color filter excellent in chemical-resistance.

Moreover, the colored resin composition of this invention can form the color filter excellent in contrast.

The colored resin composition of the present invention includes a colorant (hereinafter, sometimes referred to as a coloring agent (A)), a resin (hereinafter sometimes referred to as a resin (B)), a polymerizable compound (hereinafter, referred to as a polymerizable compound (C)). ), and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)).

In the colored resin composition of this invention, a coloring agent contains the compound (Hereinafter, it may call a compound (1)) represented by Formula (1).

It is preferable that the colored resin composition of this invention contains a solvent (Hereinafter, it may call a solvent (E).) further.

The colored resin composition of this invention may also contain a leveling agent.

In this specification, the compound illustrated as each component can be used individually or in combination of multiple types, unless otherwise indicated.

<Colorant (A)>

The compound represented by 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 directly bonded to the silicon atom. is a compound.

[Formula 1]

(In formula (1), R ^101a to R ^101d and R ^102a to R ^102d each independently represent an optionally substituted alkyl group or an optionally substituted aryl group.

X ¹ and X ² each independently represent a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an aralkyl group which may have a substituent, or a group represented by formulas (X1) to (X4) .

[Formula 2]

R ²⁰¹ and R ⁴⁰¹ each independently represent an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group.

R ³⁰¹ , R ³⁰² and R ⁵⁰¹ to R ⁵⁰³ each independently represent an optionally substituted alkyl group or an optionally substituted aryl group.

* in Formulas (X1) to (X4) represents a bonding site with an oxygen atom.

The aromatic hydrocarbon ring constituting the aryl group, aralkyl group, and aryloxy group represented by X ¹ , X ² , R ²⁰¹ , and R ⁴⁰¹ may be coordinated with a metal atom.)

In this specification, the "alkyl group" includes linear, branched and cyclic groups. In addition, it is the same also about an "alkoxy group."

In addition, in this specification, "aryl group" represents the group which consists only of an unsubstituted aromatic hydrocarbon ring.

In the formula (1), R ^101a to R ^101d and R ^102a to R ^102d are groups bonded to the tetraazaporphyrin skeleton.

The four groups of R ^101a to R ^101d may be the same or different, preferably the same, and the four groups of R ^102a to R ^102d may be the same or different, and preferably the same.

The combination of R ^101a and R ^102a , R ^101b and R ^102b , R ^101c and R ^102c , 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.

And, 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 positional relationship of the two groups in each combination is arbitrary, and four different types of isomers exist in compound (1).

Formula (1) means that all four types of isomers are included. In addition, only one of these isomers may be contained in a tetraazaporphyrin compound, and multiple types may be contained as a mixture.

R ^101a to R ^101d and R ^102a to R ^102d each independently represent an optionally substituted alkyl group or an optionally substituted aryl group.

Examples of the alkyl group which may have a substituent as R ^101a to R ^101d and R ^102a to R ^102d in Formula (1) include a linear, branched or cyclic alkyl group.

Examples of the linear, branched or cyclic alkyl group include a methyl group, an ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, linear alkyl groups such as n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group and 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-dimethylhexyl 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-di Ethyloctyl group, 6-methyl-4-butyloctyl group, 3,5-dimethylheptadecyl group, 2,6-dimethylheptadecyl group, 2,4-dimethylheptadecyl group, 2,2,5,5-tetra Branched alkyl group such as methylhexyl group; Cyclic alkyl group (cycloalkyl group) such as cyclopentyl group, cyclohexyl group, 1-cyclopentyl-2,2-dimethylpropyl group, and 1-cyclohexyl-2,2-dimethylpropyl group );

It is preferable that carbon number of an alkyl group is 1-20, It is more preferable that it is 1-15, It is still more preferable that it is 1-10, It is still more preferable that it is 1-5.

Among these, a C1-C10 linear or branched alkyl group is preferable, a C1-C5 linear or branched alkyl group is more preferable, and a tert-butyl group is still more preferable.

Examples of the alkyl group having a substituent include those in which some or all of the hydrogen atoms of the alkyl group are substituted with halogen, examples of which include a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, and a nonafluoro group. A butyl group, a perfluorocyclobutyl group, a perfluorocyclopentyl group, etc. are mentioned.

Examples of the aryl group which may have a substituent as R ^101a to R ^101d and R ^102a to R ^102d in Formula (1) include a phenyl group, a nitrophenyl group, a cyanophenyl group, a hydroxyphenyl group, a carboxyphenyl group, a methylphenyl group, a dimethylphenyl group, and a trimethylphenyl group. , fluorophenyl group, chlorophenyl group, bromophenyl group, methoxyphenyl group, ethoxyphenyl group, trifluoromethylphenyl group, N,N-dimethylaminophenyl group, naphthyl group, nitronaphthyl group, cyanonaphthyl group, hydroxynaphthyl group , a methylnaphthyl group, a fluoronaphthyl group, a chloronaphthyl group, a bromonaphthyl group, and a trifluoromethylnaphthyl group.

Carbon number of an aryl group is 6-20, Preferably it is 6-18, More preferably, it is 6-15, More preferably, it is 6-10.

Moreover, in Formula (1), it is preferable that R ^102a -R ^102d are each independently group represented by Formula (R1).

[Formula 6]

(in formula (R1), R ^601a to R ^601e are each independently a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, or a substituent represents an aryloxy group that can

Examples of the optionally substituted alkyl group as R ^601a to R ^601e in the formula (R1) include the optionally substituted alkyl group exemplified by R ^101a to R ^101d and R ^102a to R ^102d .

Examples of the optionally substituted aryl group as R ^601a to R ^601e in the formula (R1) include the optionally substituted aryl group exemplified by R ^101a to R ^101d and R ^102a to R ^102d .

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, an ethoxyphenyl group, a trifluoro Methylphenyl group, N,N-dimethylaminophenyl group, naphthyl group, nitronaphthyl group, cyanonaphthyl group, hydroxynaphthyl group, methylnaphthyl group, fluoronaphthyl group, chloronaphthyl group, bromonaphthyl group, trifluoromethyl A naphthyl group etc. are mentioned.

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, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, 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, cyclo A hexyloxy group is mentioned.

Some or all of the hydrogen atoms of the alkoxy group are substituted with halogen, and a fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 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-trifluoro Roethoxy group, 2,2-difluoroethoxy group, 1,2-difluoroethoxy group, 1,1-difluoroethoxy group, 2-fluoroethoxy group, 1-fluoro Ethoxy 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, 2,2,3,3,4,4,5, 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, 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-1-heptyloxy group Tyloxy group, 7,7,8,8,8-pentafluoro-1-octyloxy group, 3,3,4,4,5,5,6,6,7,7,8,8,8-tri Decafluoro-1-octyloxy group, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-1-no nyloxy 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- Decyloxy group, 7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluoro-1-dodecyloxy group, 3,3,4,4,5 ,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-tetradecyloxy group, 1H,1H,2,5-bis( triple Oromethyl)-3,6-dioxaundecafluoro-1-nonyloxy group, 6-(perfluoro-1-methylethyl)-1-hexyloxy group, 2-(perfluoro-1-methyl Butyl)-1-ethoxy group, 2-(perfluoro-3-methylbutyl)ethoxy group, 2-(perfluoro-7-methyloctyl)ethoxy group, 2H-hexafluoro-2-propoxy group, 2,2-bis(trifluoromethyl)-1-propoxy group etc. are mentioned.

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, 1-naphthoxy group, 2-naphthoxy group, 2-methylphenoxy group, 4-methylphenoxy group, 4-tert-butylphenoxy group, 2-methoxyphenoxy group, 4-isopropyl group A phenoxy group etc. are mentioned.

The substituent in the aryloxy group which may have a substituent is not particularly limited, for example, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a linear, branched chain or cyclic alkoxy group having 1 to 8 carbon atoms. group, an amino group, a mono or dialkylamino group (the alkyl group has 1 to 8 carbon atoms), a halogen atom, a cyano group, a hydroxyl 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 trifluoromethylphenyl group. have.

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

Moreover, as a group represented by Formula (R1), it is preferable that at least 1 of ^R601a , ^R601c , and ^R601e is each independently a fluorine atom, a chlorine atom, a bromine atom, a methyl group, or a trifluoromethyl group.

Specific examples include 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2, 6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,4,6-trifluorophenyl group, 2,3,5,6-tetrafluorophenyl group, 2 A phenyl group to which a fluorine atom is bonded, such as a 3,4,5,6-pentafluorophenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2,3-dichlorophenyl group, a 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, 2 ,3,4,5,6-Phenyl group to which chlorine atoms such as pentachlorophenyl group are 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-tribromo A phenyl group to which a bromine atom is bonded, such as a phenyl group, 2,3,5,6-tetrabromophenyl group, 2,3,4,5,6-pentabromophenyl 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-dimethylphenyl group, 2,4,6-trimethyl A phenyl group to which an alkyl group such as a phenyl 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-ditrifluoromethylphenyl group, 2,6-ditrifluoromethylphenyl group Group, 3,4-ditrifluoromethylphenyl group, 3,5-ditrifluoromethylphenyl group, 2,4,6-tritrifluoromethylphenyl group, 2,3,5,6-tetratrifluoromethylphenyl The phenyl group etc. which fluorinated alkyl groups, such as group and 2,3,4,5,6- pentafluoromethylphenyl group, couple|bonded are mentioned.

Among these, a phenyl 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 is bonded, a 2-chlorophenyl group, a 4-chlorophenyl group, 2 , 4-dichlorophenyl group, phenyl group to which chlorine atoms such as 2,6-dichlorophenyl group are bonded, 2-bromophenyl group, 4-bromophenyl group, 2,4-dibromophenyl group, 2,6-dibromophenyl group, etc. A phenyl group, 2-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, to which an alkyl group such as a bromine atom bonded phenyl group, 2-methylphenyl group, 4-methylphenyl group, 2,4-dimethylphenyl group, and 2,6-dimethylphenyl group is bonded , a phenyl group to which a fluorinated alkyl group such as a 2,4-ditrifluoromethylphenyl group or a 2,6-ditrifluoromethylphenyl group is bonded is preferable.

In addition, examples of the aryl group which may have a substituent other than the group represented by the formula (R1) include a naphthyl group, a nitronaphthyl group, a cyanonaphthyl group, a hydroxynaphthyl group, a methylnaphthyl group, a fluoronaphthyl group, A chloronaphthyl group, a bromonaphthyl group, a trifluoromethylnaphthyl group, etc. are mentioned.

Among the groups bonded to the tetraazaporphyrin skeleton, R ^101a to R ^101d are each independently preferably a linear or branched alkyl group which may have a substituent, and a linear or branched alkyl group having 1 to 10 carbon atoms. is preferable, and a C1-C5 linear or branched alkyl group is more preferable. In particular, it is preferable that R ^101a to R ^101d are all tert-butyl groups.

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

In the tetraazaporphyrin compound represented by the formula (1), the central atom is Si, two O (oxygen atom) are bonded to Si as an axial ligand, and X ¹ or X ² is bonded to each O. are being prepared

Hereinafter, examples of preferable structures of X ¹ and X ² which are 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 each independently a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an aralkyl group which may have a substituent, or a group represented by the following formulas (X1) to (X4) indicates.

* in formulas (X1) to (X4) is a bonding site with an oxygen atom.

[Formula 7]

R ²⁰¹ and R ⁴⁰¹ each independently represent 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 an aryloxy group which may have a substituent,

R ³⁰¹ , R ³⁰² and R ⁵⁰¹ to R ⁵⁰³ each independently represent an optionally substituted alkyl group or an optionally substituted aryl group.

Examples of the optionally substituted alkyl group and the optionally substituted aryl group as X ¹ or X ² include the optionally substituted alkyl group and optionally substituted aryl group given as examples of R ^101a to R ^101d and R ^102a to R ^102d . can be lifted

Examples of the aralkyl group which may have a substituent as X ¹ or X ² include groups in which an alkanediyl group having 1 to 5 carbon atoms, such as a methylene group, ethylene group, and propylene group, is bonded to the group described as the aryl group.

R ²⁰¹ in formula (X1) represents an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group. Carbon number of the alkyl group which represents R ²⁰¹ becomes like this. Preferably it is 1-20, More preferably, it is 5-20, More preferably, it is 5-15. Carbon number of the aryl group which represents R ²⁰¹ is, for example, 6-20, Preferably it is 6-18, More preferably, it is 6-15, More preferably, it is 6-10.

Examples of the optionally substituted alkyl group and the optionally substituted aryl group include the optionally substituted alkyl group and optionally substituted aryl group given as examples of R ^101a to R ^101d and R ^102a to R ^102d . .

Examples of the optionally substituted alkoxy group and the optionally substituted aryloxy group include the optionally substituted alkoxy group listed as R ^601a to R ^601e in the formula (R1), and the optionally substituted aryloxy group. have.

R ²⁰¹ in formula (X1) is preferably an optionally substituted alkyl group or optionally substituted aryl group, a linear or branched alkyl group, optionally substituted phenyl group, or optionally substituted cyclopentadienyl anion. These are more preferable, and 1-ethylpentyl group, a phenyl group, 3-nitrophenyl group, 4-carboxyphenyl group, 3-carboxyphenyl group, 4-hydroxyphenyl group, ferrocene, etc. are still more preferable.

R ³⁰¹ and R ³⁰² in the formula (X2) each independently represent an optionally substituted alkyl group or an optionally substituted aryl group.

Examples of the optionally substituted alkyl group and the optionally substituted aryl group include the optionally substituted alkyl group and optionally substituted aryl group given as examples of R ^101a to R ^101d and R ^102a to R ^102d . .

R ⁴⁰¹ in formula (X3) represents an optionally substituted alkyl group, optionally substituted aryl group, optionally substituted alkoxy group, or optionally substituted aryloxy group.

Examples of the optionally substituted alkyl group and the optionally substituted aryl group include the optionally substituted alkyl group and optionally substituted aryl group given as examples of R ^101a to R ^101d and R ^102a to R ^102d . .

Examples of the optionally substituted alkoxy group and the optionally substituted aryloxy group include the optionally substituted alkoxy group listed as R ^601a to R ^601e in the formula (R1), and the optionally substituted aryloxy group. have.

R ⁵⁰¹ to R ⁵⁰³ in formula (X4) each independently represent an optionally substituted alkyl group or an optionally substituted aryl group.

Examples of the optionally substituted alkyl group and the optionally substituted aryl group include the optionally substituted alkyl group and optionally substituted aryl group given as examples of R ^101a to R ^101d and R ^102a to R ^102d . .

Among them, R ⁵⁰¹ to R ⁵⁰³ in formula (X4) are each independently preferably an optionally substituted alkyl group, more preferably an alkyl group having 1 to 5 carbon atoms, furthermore a methyl group or an ethyl group desirable.

It is preferable that the aryl group which may have a substituent in X< ¹ > and X< ² > is group represented by following formula (2).

[Formula 8]

R ⁷⁰¹ in Formula (2) is CO ₂ R ^701a , an optionally substituted alkoxy group, an optionally substituted aryloxy group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a substituent (eg, halogen atom) or a nitrogen atom-containing heterocyclic group, n represents an integer from 0 to 5, R ^701a is a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group and * indicates a bonding site with an oxygen atom. When n is an integer of 2 or more, a plurality of R ⁷⁰¹ may be the same or different, respectively.

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

n in Formula (2) is an integer of 0-5. When n is 0, Formula (2) represents a phenyl group.

When n is an integer of 2 or more, some R ⁷⁰¹ may be same or different. When n is 1, the position of R ⁷⁰¹ is preferably p-position with respect to the bonding site * with an oxygen atom.

When R ⁷⁰¹ is an optionally substituted alkoxy group or an optionally substituted aryloxy group, as the optionally substituted alkoxy group and optionally substituted aryloxy group, R ^601a to R ^601e in formula (R1) An alkoxy group which may have a substituent and the aryloxy group which may have a substituent are mentioned as mentioned.

When R ⁷⁰¹ is an optionally substituted alkyl group, examples of the optionally substituted alkyl group include the optionally substituted alkyl group exemplified by R ^101a to R ^101d and R ^102a to R ^102d .

The nitrogen atom-containing heterocyclic group is preferably a piperazinyl group, a piperidinyl group, a pyrrolidinyl group, an imidazolidinyl group, a pyrazolidinyl group or the like, and among these, a piperadinyl 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 when R ^701a is an alkyl group which may have a substituent or an aryl group which may have a substituent, CO ₂ R ^701a is an acyl group It represents an oxycarbonyl group.

When R ^701a is an alkyl group which may have a substituent or an aryl group which may have a substituent, examples of R ^101a to R ^101d and R ^102a to R ^102d as an alkyl group which may have a substituent and 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 are mentioned as mentioned.

Among these groups, as group represented by Formula (2), 4-carboxyphenyl group, phenyl group, 3-hydroxyphenyl group, 3,5-dihydroxyphenyl group, 3,5-difluorophenyl group, 4-piperadinylphenyl 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 is 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 preferred.

The aromatic hydrocarbon ring constituting the aryl group, aralkyl group, and 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, etc., and is preferably a cyclopentadienyl anion ring.

The metal atom may be Fe, Cu, Cr, Co or the like, and Fe is preferable.

The fact that it may be coordinated to a metal atom indicates that a sandwich-type metal complex may be formed together with the aromatic hydrocarbon ring.

In Formula (1), X ¹ and X ² are at least one of a hydrogen atom, an optionally substituted aryl group, an optionally substituted aralkyl group, and a group represented by Formula (X1) (preferably R ²⁰¹ ). is preferably an alkyl group which may have a substituent, an aryl group which may have a substituent), a group represented by formula (X4) (preferably an alkyl group in which R ⁵⁰¹ to R ⁵⁰³ may have a substituent), and both are each Independently, a hydrogen atom, an aryl group which may have a substituent, an aralkyl group which may have a substituent, a group represented by 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 represented by formula (X4) (preferably an alkyl group in which R ⁵⁰¹ to R ⁵⁰³ may have a substituent) is more preferable.

In addition, in Formula (1), it is preferable that at least one of the aryl groups which may have a substituent of X ¹ and X ² is a group represented by Formula (2), and both are each independently represented by Formula (2) It is more preferable that it is a group.

In formula (1), X ¹ and X ² are both 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. 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 ₂ - An aralkyl group forming a sandwich-type metal complex together with an aryl group, an aromatic hydrocarbon ring and a metal atom, a group represented by the formula (X1) in which R ²⁰¹ is a linear or branched alkyl group, R ²⁰¹ having a carboxyl group or a nitro group The group represented by the formula (X1) which is an aryl group, the group represented by the formula (X1) wherein R ²⁰¹ is an unsubstituted aryl group, and the formula (X1) wherein R ²⁰¹ is an aryl group that forms a sandwich-type metal complex together with an aromatic hydrocarbon ring and a metal atom It is more preferable that the group represented by R ⁵⁰¹ to R ⁵⁰³ is a group represented by the formula (X4) which is a linear or branched alkyl group,

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-piperadinylphenyl group, 3,5-dimethyl-4-hydroxyphenyl group, 3,5,6-trimethyl-4-hydroxyphenyl group, Ferrocenemethyl group, ferrocenecarbonyl group, 4-t-butylphenyl group, 3-nitrophenyl group, 3-carboxyphenyl group, 4-cyanophenyl group, 4-trifluoromethylphenyl group are particularly preferable,

4-carboxyphenylcarbonyl group, trimethylsilyl group, 4-carboxyphenyl group, 3,5-difluorophenyl group, 3,5,6-trimethyl-4-hydroxyphenyl group, 4-t-butylphenyl group, 3-carboxyphenyl group , 4-cyanophenyl group, 4-trifluoromethylphenyl group or phenyl group is particularly preferable.

When X< ¹ > and X< ² > are said groups, the formed color filter is not only excellent in chemical-resistance, but also shows high contrast.

As X ¹ and X ² representing high contrast, an aryl group which may have a substituent, R ²⁰¹ is an aryl group that forms a sandwich-type metal complex together with an aromatic hydrocarbon ring and a metal atom, a group represented by the formula (X1) is preferable, A phenyl group, 4-carboxyphenyl group, 3-carboxyphenyl group, 4-cyanophenyl group, 4-trifluoromethylphenyl group, and ferrocenecarbonyl group are more preferable.

Although the compound represented by Formula (1) is a compound which normally absorbs the light which shows the orange color of 590 nm vicinity, it is preferable that the absorption maximum wavelength ((lambda)max) is 570-620 nm.

The absorption maximum wavelength of the compound represented by Formula (1) can be changed by changing the substituent couple|bonded with the tetraazaporphyrin skeleton of the compound represented by Formula (1). Moreover, a preferable upper limit of absorption maximum wavelength is 620 nm, and a more preferable upper limit is 615 nm. Moreover, a preferable lower limit of absorption maximum wavelength is 570 nm, and a more preferable lower limit is 575 nm. The absorption maximum wavelength can be measured with a spectrophotometer.

The compound represented by the formula (1) has a particularly sharp absorption spectrum including the base portion, but is an indicator of having a particularly sharp absorption spectrum including the bottom portion. It is preferable that the wavelength width from a rising wavelength to an absorption maximum wavelength is 40 nm or less, and it is preferable that the half-width in an absorption maximum wavelength is 20 nm or less.

The rising wavelength of the baseline is determined as a wavelength at which the absorbance becomes 0.01 or more when viewed from the long wavelength side when the absorbance at the absorption maximum wavelength is set to 1.

Then, the distance (wavelength width) from the rising wavelength to the absorption maximum wavelength is calculated.

In the present specification, the half width refers to the full width at half maximum, and in the absorption spectrum, two intersection points formed by a straight line parallel to the horizontal axis drawn at a value of 1/2 of the extinction coefficient value at the maximum absorption wavelength and the peak It is expressed as the distance (nm) between

Moreover, it is preferable that the compound represented by Formula (1) is group in which at least one of X< ¹ > and X2 is represented by Formula ( ² ) in Formula (1).

When at least one of X ¹ and X ² is a group represented by Formula (2), fluorescence emission from the compound represented by Formula (1) can be suppressed, so that unnecessary light affecting color tone is prevented from being generated.

The fluorescence intensity can be evaluated by measuring the fluorescence spectrum using a fluorescence spectrophotometer with the absorption maximum wavelength as the excitation wavelength, and the weaker fluorescence intensity is preferable.

The compound represented by Formula (1) is obtained with 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).

The method of obtaining the cis form of the 1,2-dicyanoethylene compound represented by Formula (4) can use the method described in Unexamined-Japanese-Patent No. 11-043619, and obtaining the diiminoisopyrrole derivative represented by Formula (5) As the method, the method described in Japanese Patent Application Laid-Open No. Hei 02-000665 can be used.

[Formula 9]

[Formula 10]

(In formulas (4) and (5), R ¹⁰¹ and R ¹⁰² each independently represent an optionally substituted alkyl group or an optionally substituted aryl group. Specifically, R ^101a to R ^101d and Examples of R ^102a to R ^102d include an optionally substituted alkyl group and an optionally substituted aryl group.)

Next, the diiminoisopyrrole derivative represented by the formula (5) is mixed with a Si source (for example, SiCl ₄ ), cyclized by heating, and hydrolyzed, so that the central atom is Si and the axial ligand of Si is an OH group. (a compound in which both X ¹ and X ² in Formula (1) are H) is obtained.

With respect to the compound obtained above, X ¹ and X ² can be substituted from a hydrogen atom to another substituent by a method such as adding a compound having a structure to which the axial ligand is to be substituted and refluxing.

For example, by adding carbonic acid or phenols, dehydration condensation occurs between a carboxy group or a phenolic hydroxyl group and an OH group of the axial ligand of Si, and X ¹ and X ² can be replaced with other substituents from hydrogen atoms. have.

In addition, you may substitute a silyl group from a hydrogen atom for X< ¹ > and X< ² > by adding a silylating agent.

Examples of the carboxylic acid and phenols used for the substitution include aliphatic carboxylic acids, aromatic carboxylic acids, phenols, and hydroxycarboxylic acids.

Specific examples thereof include benzoic acid, hydroxybenzoic acid, nitrobenzoic acid, terephthalic acid, isophthalic acid, phenol, and ethylhexanoic acid.

Examples of the silylating agent include N,O-bis(trimethylsilyl)acetamide and trimethylchlorosilane.

It is preferable that the content rate of the compound represented by Formula (1) is 0.1 mass % or more and 50 mass % or less with respect to coloring agent (A) whole quantity, It is more preferable that they are 0.5 mass % or more and 50 mass % or less, 1 mass % or more and 50 mass % or less % or less is more preferable.

It is preferable that the content rate of the compound represented by Formula (1) is 0.2 mass % or more and 20 mass % or less with respect to solid content whole quantity, It is more preferable that they are 0.5 mass % or more and 15 mass % or less, It is 1 mass % or more and 12 mass % or less more preferably.

The content rate of the colorant (A) is preferably 5 mass % or more and 60 mass % or less, more preferably 8 mass % or more and 55 mass % or less, and still more preferably 10 mass % or more and 50 mass % or less with respect to the total solid content. .

Here, "solid content whole quantity" in this specification means the quantity remove|excluding content of the solvent from colored resin composition whole quantity. The solid content whole amount and content of each component with respect to this can be measured by well-known analytical means, such as liquid chromatography or gas chromatography, for example.

The colored resin composition of this invention may contain the coloring agent (henceforth a coloring agent (A1)) other than the compound and compound (1) represented by Formula (1) as a coloring agent (A). The coloring agent (A1) may contain 1 type, or 2 or more types of coloring agents.

The coloring agent (A1) may be a dye or a pigment may be sufficient as it. Examples of the dye include known dyes described in Color Index (published by The Society of Dyers and Colorists) and dyeing notes (color dyeing yarn). In addition, according to the chemical structure, azo dye, anthraquinone dye, triphenylmethane dye, xanthene dye, cyanine dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine dye , styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Among these, organic solvent-soluble dyes are preferable. These dyes may use 2 or more types together.

Specifically, the dye of the following color index (C.I.) numbers is mentioned. 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 etc.

As a pigment, a well-known pigment can be used, For example, the pigment classified into the pigment by the color index (The Society of Dyers and Colorists publication) is mentioned. You may combine 2 or more types.

Specifically, 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, Yellow pigments, such as 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214;

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

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 , 265, 266, 268, 269, 273, and red pigments such as brominated diketopyrrolopyrrole;

C.I. Blue pigments, such as pigment blue 15, 15:3, 15:4, 15:6, 60;

C.I. Violet pigments, such as pigment violet 1, 19, 23, 29, 32, 36, 38;

C.I. The green pigment of Pigment Green 7, 36, 58 and 59 is mentioned.

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

The colorant (A1) is, if necessary, treated with rosin, surface treatment using a colorant derivative into which an acidic group or basic group is introduced, grafting treatment to the surface such as a pigment with a high molecular compound, etc., atomization treatment by sulfuric acid atomization method, etc., impurities A washing treatment with an organic solvent or water for removal, a removal treatment with an ion exchange method of ionic impurities, etc. may be performed. It is preferable that the particle diameters of a pigment etc. are respectively substantially uniform. The coloring agent (A1) will be in the state disperse|distributed uniformly in a dispersion liquid by containing a dispersing agent and performing a dispersion process.

Surfactants etc. are mentioned as a dispersing agent, Any surfactant of cationic type, anionic type, nonionic type, and amphoteric type may be sufficient. Specifically, surfactants, such as a polyester type, a polyamine type, and an acryl type, etc. are mentioned. As another dispersing agent, you may use resin (B) mentioned later. These dispersants may be used individually or in combination of 2 or more types. As a dispersing agent, if it shows by a brand name, KP (Shin-Etsu Chemical Co., Ltd. product), Florene (Kyoeisha Chemical Co., Ltd. product), Solsperse (trademark) (Zeneca Co., Ltd. product), EFKA (trademark) (made by BASF), Addisper (trademark) (made by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (trademark) (made by Bikchemi), BYK (trademark) (made by Bikchemi), etc. are mentioned.

When using a dispersing agent, Preferably the usage-amount of a dispersing agent is 100 mass parts or less with respect to 100 mass parts of coloring agents (A1), More preferably, they are 5 mass parts or more and 50 mass parts or less. When the usage-amount of a dispersing agent exists in the said range, there exists a tendency for the coloring agent (A1) containing liquid in a more uniformly dispersed state to be obtained.

In a colored resin composition, content of a coloring agent (A1) is 0 mass % or more and 50 mass % or less normally in the total amount of solid content, Preferably they are 0 mass % or more and 40 mass % or less, More preferably, they are 0 mass % or more. 30 mass % or less.

<Resin (B)>

Although resin (B) is not specifically limited, It is preferable that it is alkali-soluble resin, At least 1 type (a) (hereinafter referred to as "(a)") selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic acid anhydride A resin having a structural unit derived from ) is more preferable. The resin (B) further has a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, a structural unit derived from a monomer (b) (hereinafter sometimes referred to as “(b)”), (a) Structural unit derived from monomer (c) copolymerizable with and (however, (a) and (b) are different.) (hereinafter sometimes referred to as "(c)"), and an ethylenically unsaturated bond in the side chain It is preferable to have at least one kind of structural unit selected from the group consisting of structural units having.

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], etc. are mentioned, Preferably, they are acrylic acid, methacrylic acid, and maleic anhydride.

In addition, in this specification, "(meth)acrylic acid" shows at least 1 sort(s) chosen from the group which consists of acrylic acid and methacrylic acid. Notations, such as "(meth)acryloyl" and "(meth)acrylate", also have the same meaning.

(b) is a monomer having a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and a (meth)acryloyloxy group is preferable

As (b), for example, glycidyl (meth)acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate, 3-ethyl -3-(meth)acryloyloxymethyloxetane, tetrahydrofurfuryl(meth)acrylate, etc. are mentioned, Preferably, glycidyl (meth)acrylate, 3,4-epoxytricyclo[ 5.2.1.0 ^2,6 ] It is decyl (meth)acrylate and 3-ethyl-3- (meth)acryloyloxymethyloxetane.

As (c), for example, methyl (meth) acrylate, butyl (meth) acrylate cyclohexyl (meth) acrylate, 2-methyl cyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] Decan-8-yl (meth) acrylate benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, N-phenyl maleimide, N-cyclohexyl maleimide, N-benzyl maleimide, styrene, vinyltoluene etc. are mentioned, Preferably, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, 2-hydroxyethyl (meth)acrylate, etc. 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 adding (a) to the copolymer of (b) and (c). It can be manufactured by The resin may be a resin in which (a) is added to the copolymer of (b) and (c) and further reacted with carboxylic acid anhydride.

The weight average molecular weight of resin (B) in terms of polystyrene becomes like this. Preferably it is 3,000-100,000, More preferably, it is 5,000-50,000, More preferably, it is 5,000-30,000.

The molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)] of resin (B) becomes like this. Preferably it is 1.1-6, More preferably, it is 1.2-4.

The acid value of the resin (B) is preferably 50 to 170 mg-KOH/g in terms of solid content, more preferably 60 to 150 mg-KOH/g, and still more preferably 70 to 135 mg-KOH/g. Here, an acid value is a value measured as the quantity (mg) of potassium hydroxide required in order to neutralize 1 g of resin (B), For example, it can obtain|require by titrating using potassium hydroxide aqueous solution.

To [ the content rate of resin (B) ] with respect to solid content whole quantity, Preferably it is 10-70 mass %, More preferably, it is 15-65 mass %, More preferably, it is 20-60 mass %.

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized with an active radical and/or an acid generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, preferably Preferably, it is a (meth)acrylic acid ester compound.

Especially, it is preferable that a polymeric compound (C) is a polymeric compound which has three or more ethylenically unsaturated bonds. Examples of such a polymerizable compound include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and dipentaerythritol penta(meth)acrylate. and dipentaerythritol hexa(meth)acrylate.

The weight average molecular weight of a polymeric compound (C) becomes like this. Preferably it is 150 or more and 2,900 or less, More preferably, they are 250 or more and 1,500 or less.

It is preferable that the content rate of a synthetic compound (C) is 3-60 mass % with respect to solid content whole quantity, More preferably, it is 5-50 mass %, More preferably, it is 11-40 mass %.

<Polymerization Initiator (D)>

A polymerization initiator (D) will not be specifically limited if it is a compound which generate|occur|produces an active radical, an acid, etc. by the action|action of light or heat, and can initiate polymerization, A well-known polymerization initiator can be used. Examples of the polymerization initiator generating active radicals include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfur). Panylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine 2-methyl-2-morphol No-1-(4-methylsulfanylphenyl)propan-1-one, 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-trimethylbenzoyl diphenylphosphine oxide, 2,2'-bis (2- chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, etc. are mentioned.

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 an O-acyloxime A polymerization initiator containing a compound is more preferable.

To [ content of a polymerization initiator (D) / 100 mass parts of total amounts of resin (B) and a polymeric compound (C)), Preferably it is 0.1-30 mass parts, More preferably, it is 1-20 mass parts. When content of a polymerization initiator (D) exists in said range, since there exists a tendency for it to become highly sensitive and exposure time to shorten, productivity of a color filter improves.

The content of the O-acyl oxime compound is preferably 50 mass % or more, more preferably 80 mass % or more, still more preferably 90 mass % or more, with respect to the total amount of the polymerization initiator (D), particularly preferably Preferably, it is 95 mass % or more. When the content of the O-acyloxime compound is within the above range, there is a tendency that a color filter with high brightness can be produced even when the sensitivity and developability at the time of forming a colored pattern and the content of the colorant are high.

The colored resin composition of this invention may contain the polymerization initiation adjuvant.

<Polymerization initiation aid (D1)>

A polymerization initiation adjuvant (D1) is a compound used in order to accelerate|stimulate superposition|polymerization of the polymeric compound which superposition|polymerization was started by a polymerization initiator, or a sensitizer. When a polymerization initiator auxiliary (D1) is included, it is used in combination with a polymerization initiator (D) normally.

Examples of the polymerization initiation auxiliary (D1) include 4,4'-bis(dimethylamino)benzophenone (common name Mihirazketone), 4,4'-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone N-phenylglycine etc. are mentioned.

When using these polymerization initiation adjuvant (D1), the content is with respect to 100 mass parts of total amounts of resin (B) and a polymeric compound (C), Preferably it is 0.1-30 mass parts, More preferably, it is 1-20 mass parts. is the mass part. When the amount of the polymerization initiation auxiliary (D1) is within this range, a coloring pattern can be formed with a higher sensitivity, and the productivity of the color filter tends to be improved.

It is preferable that the colored resin composition of this invention contains a solvent.

<Solvent (E)>

The solvent (E) is not specifically limited, The solvent normally used in this field|area can be used. For example, ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether esters Solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -COO- in the molecule), alcohol solvents (containing OH in the molecule, - solvents not containing O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

Examples of the solvent include ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate and γ-butyrolactone ( Solvent containing -COO- and not containing -O- in the molecule); Ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol ether solvents such as dimethyl ether and diethylene glycol methyl ethyl ether (solvents containing -O- in the molecule and not containing -COO-);

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

Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone, and cyclohexanone (with -CO- in the molecule and without -COO- Solvent); Alcohol solvents, such as butanol, cyclohexanol, and propylene glycol (The solvent which contains OH in a molecule|numerator and does not contain -O-, -CO-, and -COO-); etc. are mentioned. Aromatic hydrocarbon solvents, such as toluene and xylene, are mentioned. and 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-methoxy-1-butanol and 4-hydroxy-4-methyl-2-pentanone are preferable, propylene glycol monomethyl ether, dipropylene glycol methyl ether acetate, ethyl lactate, 3- Methoxybutyl acetate, 3-methoxy-1-butanol and ethyl 3-ethoxypropionate are more preferable, and ethyl lactate, 4-hydroxy-4-methyl-2-pentanone and propylene glycol monomethyl ether are more preferable. do.

The content rate of the solvent in combination with propylene glycol monomethyl ether acetate is preferably 1 mass % or more and 50 mass % or less, more preferably 3 mass % or more and 40 mass % or less, further preferably with respect to the total amount of the solvent. They are 5 mass % or more and 30 mass % or less.

To [ the content rate of a solvent (E) ] when a solvent (E) is included with respect to the colored resin composition whole quantity of this invention, Preferably it is 20-80 mass %, More preferably, it is 25-75 mass %. In other words, solid content whole quantity of a colored resin composition becomes like this. Preferably it is 5-30 mass %, More preferably, it is 8-25 mass %. When the content rate of the solvent (E) is within the above range, flatness at the time of application becomes favorable, and since color density does not run short when a color filter is formed, there exists a tendency for a display characteristic to become favorable.

<Other ingredients>

As needed, the colored resin composition of this invention may contain well-known additives in the said technical field, such as a leveling agent, a filler, another high molecular compound, an adhesion promoter, antioxidant, a light stabilizer, and a chain transfer agent.

<The manufacturing method of a colored resin composition>

The colored resin composition of this invention can be prepared by mixing a coloring agent (A), resin (B), a polymeric compound (C), a polymerization initiator (D), and a solvent (E) and other components as needed.

<The manufacturing method of a color filter>

As a method of manufacturing a colored pattern from the colored resin composition of this invention, the photolithographic method, the inkjet method, the printing method, etc. are mentioned. Especially, the photolithographic method is preferable. In the photolithography method, the colored coating film which is the hardened|cured material of the said colored resin composition layer can be formed by not using a photomask at the time of exposure and/or not developing. The colored pattern and colored coating film thus formed are the color filters of the present invention.

A colored resin composition can produce the color filter excellent in chemical-resistance and contrast. The color filter is useful as a color filter used for a display device (eg, a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state image sensor.

Example

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 from the beginning, and it is also carried out with appropriate changes within the range that can be suitable for the gist of the preceding and latter period. Of course, it is possible, and they are all included in the technical scope of the present invention.

[Synthesis Example 1]

(Synthesis of diiminoisopyrrole derivatives)

The compound represented by Formula (x) was obtained by the synthesis method described in patent 3961078. Moreover, from the compound represented by Formula (x), it carried out similarly to the synthesis method described in Unexamined-Japanese-Patent No. 02-000665, and obtained the compound represented by Formula (y).

[Formula 11]

[Synthesis Example 2]

In a reactor equipped with a cooling tube, a thermometer and a stirrer, quinoline (20 ml) and SiCl ₄ (2.38 g) were put, and 2.45 g of a compound represented by the formula (y) was added at 120° C., and reacted at 150° C. for 3 hours. The reaction solution was poured into diluted hydrochloric acid at 80°C, the precipitate was separated by filtration, washed with methanol, and 0.8 g of a compound represented by the formula (a-1) was obtained.

[Formula 12]

[Synthesis Example 3]

In a 25 ml reactor equipped with a cooling tube, a thermometer and a stirrer, the compound (2.0 g) represented by the formula (a-1), dimethylacetamide (10 ml), and terephthalic acid (1.5 g) were put, and refluxed for 2 hours. It stood to cool, the reaction liquid was concentrated, it refine|purified by silica gel column chromatography, and 0.6g of the compound represented by Formula (a-2) was obtained.

[Formula 13]

[Synthesis Example 4]

In a reactor equipped with a cooling tube, a thermometer, and a stirrer, the compound (1 g) represented by the formula (a-1), pyridine (3 ml), and N,O-bis(trimethylsilyl)acetamide (1 g) were put, and 90° C. was stirred for 1 hour. The reaction solution was discharged into water, and the precipitated solid was separated by filtration and purified by silica gel column chromatography to obtain 0.5 g of a compound represented by the formula (a-3).

[Formula 14]

[Synthesis Example 5]

In a 25 ml reactor equipped with a cooling tube, a thermometer, and a stirrer, the compound (2.0 g) represented by the formula (a-1), mesitylene (10 ml), and 4-hydroxybenzoic acid (1.5 g) were put, and refluxed for 2 hours. . It stood to cool, the reaction liquid was concentrated, it refine|purified by silica gel column chromatography, and 1.2g of compounds represented by Formula (a-4) were obtained.

[Formula 15]

[Synthesis Example 6]

Except having changed 4-hydroxybenzoic acid in the synthesis example 5 into 2-ethylhexanoic acid, it carried out similarly, and 1.6g of compounds represented by Formula (a-5) were obtained.

[Formula 16]

[Synthesis Example 7]

Except having changed the 4-hydroxybenzoic acid in the synthesis example 5 into the phenol, it carried out similarly, and 1.0g of the compound represented by Formula (a-6) was obtained.

[Formula 17]

[Synthesis Example 8]

In a 25 ml reactor equipped with a cooling tube, a thermometer, and a stirrer, the compound (2.0 g) represented by the formula (a-1), mesitylene (10 ml), and benzoic acid (1.5 g) were put, and refluxed for 2 hours. It stood to cool, the reaction liquid was concentrated, it refine|purified by silica gel column chromatography, and 1.2g of compounds represented by Formula (a-7) were obtained.

[Formula 18]

[Synthesis Example 9]

Except having changed the benzoic acid in Synthesis Example 8 into 3-nitrobenzoic acid (1.5 g), it carried out similarly, and obtained 1.4g of the compound represented by Formula (a-8).

[Formula 19]

[Synthesis Example 10]

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

[Formula 20]

[Synthesis Example 11]

From the compound represented by Formula (x), the compound represented by Formula (b-1) was obtained by the synthesis method described in patent 3961078.

[Formula 21]

[Synthesis Example 12]

In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was flowed into the flask, replaced with a nitrogen atmosphere, 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were placed, and the mixture was heated to 85° C. while stirring. Subsequently, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]deca-8-ylacrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]deca-9-ylacrylic A mixed solution of 25 parts of the mixture (content is 1:1), 137 parts of cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was dripped over 5 hours. On the other hand, the mixed solution which melt|dissolved 5 parts of 2, 2- azobisisobutyronitrile in 88 parts of propylene glycol monomethyl ether acetate was dripped over 6 hours. After completion|finish of dripping, it stored at the same temperature for 4 hours, it cooled to room temperature, and obtained the copolymer (resin (B-1)) solution with a B type viscosity (23 degreeC) 23 mPa*s, and solid content 25.6%. The resulting copolymer had a weight average molecular weight Mw of 8000, a solid content acid value of 111 mg-KOH/g, and a dispersion degree of 2.1. Resin (B-1) has the following structural unit.

[Formula 22]

The measurement of the polystyrene conversion weight average molecular weight (Mw) and number average molecular weight (Mn) of resin was performed on condition of the following by GPC method.

Device; HLC-8120GPC (manufactured by Tosoh Corporation)

Column; TSK-GELG2000HXL

Column temperature; 40°C

solvent; THF

Flow rate; 1.0 mL/min

Test solution solid content concentration; 0.001 to 0.01 mass%

Injection volume; 50 μL

detector; RI

Standard material for calibration　；TSK　STANDARD　POLYSTYRENE

F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

Ratio (Mw/Mn) of the polystyrene conversion weight average molecular weight and number average molecular weight obtained above was made into the dispersion degree.

[Synthesis Example 13]

In a 25 ml reactor equipped with a cooling tube, thermometer, and stirrer, the compound represented by formula (a-1) (0.20 g), digrim (5.5 g), and resorcinol (0.23 g) were put into it, and 2 hours at 150 ° C. stirred. It stood to cool, and the reaction liquid was dripped at 30 g of 20% saline, the precipitated solid was collected by filtration, and it flowed out with water. After dispersion-washing solid with water, it dried in 40 degreeC vacuum oven, and obtained 0.23g of the compound represented by Formula (a-10).

[Formula 23]

[Synthesis Example 14]

0.24 g of the compound represented by Formula (a-11) was obtained in the same manner except that resorcinol in Synthesis Example 13 was changed to chloroglucinol.

[Formula 24]

[Synthesis Example 15]

0.20 g of the compound represented by Formula (a-12) was obtained similarly except having changed resorcinol in Synthesis Example 13 into 3,5-difluorophenol.

[Formula 25]

[Synthesis Example 16]

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

[Formula 26]

[Synthesis Example 17]

0.20 g of the compound represented by Formula (a-14) was obtained similarly except having changed the resorcinol in Synthesis Example 13 into 2,6-dimethylhydroquinone.

[Formula 27]

[Synthesis Example 18]

0.21 g of the compound represented by Formula (a-15) was obtained similarly except having changed the resorcinol in Synthesis Example 13 into trimethylhydroquinone.

[Formula 28]

[Synthesis Example 19]

0.20 g of the compound represented by Formula (a-16) was obtained similarly except having changed the resorcinol in Synthesis Example 13 into hydroxymethylferrocene.

[Formula 29]

[Synthesis Example 20]

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

[Formula 30]

[Synthesis Example 21]

In a 50 ml reactor equipped with a cooling tube, a thermometer, and a stirrer, the compound (9.0 g) represented by the formula (a-1), toluene (20 ml), and 4-t-butylphenol (8.1 g) were put, and 3 at 100 ° C. time was stirred. It refine|purified with the silica gel column, and obtained 6.3g of compounds represented by Formula (a-18).

[Formula 31]

[Synthesis Example 22]

In a 50 ml reactor equipped with a cooling tube, a thermometer and a stirrer, the compound (1.5 g) represented by the formula (a-1), toluene (20 ml), and 3-nitrophenol (2.8 g) were put, and stirred at 100° C. for 0.5 hours. did it It refine|purified with the silica gel column and obtained 1.0g of the compound represented by Formula (a-19).

[Formula 32]

[Synthesis Example 23]

In a 25 ml reactor equipped with a cooling tube, a thermometer and a stirrer, the compound (1.9 g) represented by the formula (a-1), toluene (10 ml), and 3-hydroxybenzoic acid (3.3 g) were put, and stirred under reflux for 0.5 hours did it The mixture was discharged into water/ethyl acetate, and the precipitate was collected by filtration, dissolved in N,N-dimethylformamide, and treated with clay and silica gel to obtain 1.5 g of a compound represented by the formula (a-20).

[Formula 33]

[Synthesis Example 24]

In a 50 ml reactor equipped with a cooling tube, a thermometer, and a stirrer, the compound (1.5 g) represented by the formula (a-1), toluene (15 ml), and 4-cyanophenol (3.0 g) were put, and 20 minutes at 100 ° C. stirred. After cooling to room temperature, the insoluble matter was removed by filtration, and it refine|purified by the silica gel column, and 0.7g of the compound represented by Formula (a-21) was obtained.

[Formula 34]

[Synthesis Example 25]

In a 50 ml reactor equipped with a cooling tube, a thermometer, and a stirrer, the compound (1.5 g) represented by the formula (a-1), toluene (15 ml), and 4-trifluoromethylphenol (3.0 g) were put, and at 100 ° C. Stirred for 20 minutes. After cooling to room temperature, the insoluble matter was removed by filtration, and it refine|purified with the silica gel column, and obtained 1.6g of the compound represented by Formula (a-22).

[Formula 35]

[Synthesis Example 26]

The compound represented by Formula (c-1) was obtained by the synthesis method described in Unexamined-Japanese-Patent No. 2016-27075.

[Formula 36]

<Preparation of colored resin composition>

[Example 1]

By mixing the following components, the colored resin composition was obtained.

Compound (1): 3 parts of compound represented by formula (a-1)

Resin (B): 65 parts of resin (B-1) (in terms of solid content)

Polymeric compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) 　DPHA; manufactured by Nippon Kayaku Co., Ltd.) 　35 parts

Polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE01; manufactured by BASF; O-acyloxime compound) Part 7.0

Solvent (E): 501 parts of propylene glycol monomethyl ether acetate

Ethyl lactate 　38 parts

Leveling agent (H): 0.10 part of polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[Example 2]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-2).

[Example 3]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-3).

[Example 4]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-4).

[Example 5]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-5).

[Example 6]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-6).

[Example 7]

A colored resin composition is obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-7) 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 for using the compound represented by the formula (a-8) 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 for using the compound represented by the formula (a-9) instead of the compound represented by the formula (a-1).

[Preparation of Dispersion 1]

C.I. Pigment Red 254 (pigment) 14 parts, acrylic pigment dispersant 4.9 parts, resin (B-1) (solid content conversion) 4.2 parts, propylene glycol monomethyl ether acetate 74 parts and ethyl lactate 2.5 parts were mixed, and a bead mill was used. Thus, the pigment was sufficiently dispersed to prepare a dispersion liquid 1.

[Example 10]

By mixing the following components, the colored resin composition was obtained.

Compound (1): 5 parts of compound represented by formula (a-1)

Colorant (A1): Dispersion 1 　422 parts

Resin (B): Resin (B-1) (in terms of solid content) 　 40 parts

Polymeric compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) 　DPHA; manufactured by Nippon Kayaku Co., Ltd.) 　35 parts

Polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE01; manufactured by BASF; O-acyloxime compound) Part 7.0

Solvent (E): 553 parts of propylene glycol monomethyl ether acetate

22 parts of ethyl lactate

Leveling agent (H): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 　0.10 parts

[Example 11]

The colored resin composition was obtained like Example 10 except using the compound represented by a formula (a-3) instead of the compound represented by a formula (a-1).

[Comparative Example 1]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (b-1).

<Production 1 of color filter (colored coating film)>

After apply|coating the colored resin composition by the spin coating method on the glass substrate (Eagle 2000; Corning company make) of 5 cm corner, it prebaked at 100 degreeC for 3 minute(s), and the colored resin composition layer was formed. After standing to cool, it was irradiated with light at an exposure amount (365 nm standard) of 60 mJ/cm 2 in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). After that, it post-baked at 230 degreeC in oven for 20 minutes, and obtained the color filter.

[Example 12]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-10).

[Example 13]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-11).

[Example 14]

Instead of using the compound represented by the formula (a-1), the 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.

[Example 15]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-13).

[Example 16]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-14).

[Example 17]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-15).

[Example 18]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-16).

[Example 19]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-17).

[Example 20]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-18).

[Example 21]

The colored resin composition was obtained like Example 1 except having used the compound represented by Formula (a-19) instead of the compound represented by Formula (a-1).

[Example 22]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-20).

[Example 23]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 1 except for using the compound represented by the formula (a-21).

[Example 24]

The colored resin composition was obtained like Example 1 except using the compound represented by Formula (a-22) instead of the compound represented by Formula (a-1).

[Example 25]

By mixing the following components, the colored resin composition was obtained.

Compound (1): 5 parts of compound 　 represented by formula (a-1)

Coloring agent (A1): 24 parts of compounds represented by Formula (c-1)

Resin (B): 40 parts of resin (B-1) (in terms of solid content)

Polymeric compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) 　DPHA; manufactured by Nippon Kayaku Co., Ltd.) 　35 parts

Polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE01; manufactured by BASF; O-acyloxime compound) Part 7.0

Solvent (E): 553 parts of propylene glycol monomethyl ether acetate

22 parts of ethyl lactate

Leveling agent (H): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 　0.10 parts

[Example 26]

The colored resin composition was obtained like Example 25 except having used the compound represented by a formula (a-3) instead of the compound represented by a formula (a-1).

[Example 27]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 25 except for using the compound represented by the formula (a-5).

[Example 28]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 25 except for using the compound represented by the formula (a-7).

[Example 29]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 25 except for using the compound represented by the formula (a-16).

[Example 30]

Instead of using the compound represented by the formula (a-1), the 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.

[Comparative Example 2]

Instead of using the compound represented by the formula (a-1), the colored resin composition was obtained in the same manner as in Example 25 except for using the compound represented by the formula (b-1).

<Chemical resistance test>

Production of color filter The color filter obtained by the method of 1 was immersed in N-methylpyrrolidone temperature-controlled at 40 degreeC for 30 minutes. About the color filter before and after immersion, the spectral spectrum at a wavelength of 400-780 nm was measured using a colorimeter (OSP-SP-200; Olympus Co., Ltd. product), and the absorbance change rate in the maximum absorption wavelength λmax (after immersion) Absorbance/absorbance before immersion) was calculated. The lower the absorbance change rate, the better the chemical resistance. The results are shown in Tables 1 and 2.

<Production 2 of color filter (colored coating film)>

On a 5 cm corner glass substrate (Eagle 2000; manufactured by Corning), the colored resin composition was applied by spin coating, and then, using a vacuum dryer (manufactured by VCD Microtech Co., Ltd.), until the pressure reached 66 Pa. It dried under reduced pressure to form the colored resin composition layer. After standing to cool, it was irradiated with light at an exposure amount (365 nm standard) of 60 mJ/cm 2 in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). After that, it post-baked at 100 degreeC in oven for 3 minutes, and obtained the color filter.

<Contrast measurement>

About the color filter obtained by the method of manufacture 2 of a color filter, Contrast meter (CT-1; Tsubosaka Electric Co., Ltd. make, color difference meter BM-5A; Topcon company make, light source; F-10, Polarizing film; Tsubosaka Corporation) The contrast was measured with the blank value of 30000 using the article). 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)

a colorant, a resin, a polymerizable compound, and a polymerization initiator;
The colored resin composition in which the said coloring agent contains the compound represented by Formula (1).
[Formula 1]

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

In Formula (R1), R ^601a to R ^601e may each independently have a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryl group which may have a substituent or a substituent. represents an aryloxy group with
At least one of R ^601a , R ^601c and R ^601e represents a fluorine atom,
* in formula (R1) represents a binding site with a tetraazaporphyrin skeleton.
In Formula (1), X ¹ and X ² each independently represent an optionally substituted aryl group or group represented by Formula (X1).
[Formula (X1)]

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