JP6937110B2 - Compound - Google Patents

Description

The present invention relates to compounds.

Colored resin compositions are used in the manufacture of color filters used in display devices such as liquid crystal displays, electroluminescence display devices, and plasma displays. As such a colored resin composition, a colored resin composition containing a compound represented by the following formula as a colorant is known.

Japanese Unexamined Patent Publication No. 2013-50693

The color filter formed from the conventionally known colored resin composition containing the above compound may not have a sufficiently satisfactory contrast.

［式（１）中、Ｒ¹〜Ｒ⁴は、互いに独立に、水素原子、置換基を有していてもよい炭素数１〜２０の飽和炭化水素基、又は、置換基を有していてもよい炭素数６〜１０の芳香族炭化水素基を表し、少なくとも一つは置換基として複素環基を有する炭素数６〜１０の芳香族炭化水素基を表し、該飽和炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−又は−ＮＲ⁵−に置き換わっていてもよい。Ｒ¹及びＲ²は、一緒になって窒素原子を含む環を形成してもよく、Ｒ³及びＲ⁴は、一緒になって窒素原子を含む環を形成してもよい。Ｒ⁵〜Ｒ⁷は、互いに独立に、水素原子又は炭素数１〜６のアルキル基を表す。］
［２］Ｒ¹が、置換基として複素環基を有する炭素数６〜１０の芳香族炭化水素基を表し、かつ、Ｒ²〜Ｒ⁴が、互いに独立に、置換基を有していてもよい炭素数１〜２０の飽和炭化水素基、又は、水素原子を表すか、あるいは、Ｒ¹及びＲ³が、置換基として複素環基を有する炭素数６〜１０の芳香族炭化水素基を表し、かつ、Ｒ²及びＲ⁴が、互いに独立に、置換基を有していてもよい炭素数１〜２０の飽和炭化水素基、又は、水素原子を表す、［１］記載の化合物。
［３］前記複素環基を有する炭素数６〜１０の芳香族炭化水素基が、式（１ｘ）で表される基である［１］又は［２］記載の化合物。

［式（１ｘ）中、Ｑ¹は、複素環基を表す。＊は窒素原子との結合手を表す。］
［４］前記複素環基が、窒素原子を含む複素環基である［１］〜［３］のいずれか記載の化合物。
［５］［１］〜［４］のいずれか記載の化合物及び樹脂を含む着色樹脂組成物。
［６］［５］記載の着色樹脂組成物から形成されるカラーフィルタ。
［７］［６］記載のカラーフィルタを含む表示装置。 That is, the present invention includes the following inventions.
[1] A compound represented by the formula (1).

[In the formula (1), R ^{1 to} R ⁴ have a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a substituent independently of each other. It represents a good aromatic hydrocarbon group having 6 to 10 carbon atoms, and at least one represents an aromatic hydrocarbon group having 6 to 10 carbon atoms having a heterocyclic group as a substituent and is contained in the saturated hydrocarbon group. −CH ₂ − may be replaced with −O −, −CO− or −NR ^5−. R ¹ and R ² may be combined to form a ring containing a nitrogen atom, and R ³ and R ⁴ may be combined to form a ring containing a nitrogen atom. R ^{5 to} R ⁷ represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other. ]
[2] Even if R ¹ represents an aromatic hydrocarbon group having 6 to 10 carbon atoms having a heterocyclic group as a substituent and R ^{2 to} R ⁴ have substituents independently of each other. It represents a good saturated hydrocarbon group having 1 to 20 carbon atoms or a hydrogen atom, or R ¹ and R ³ represent an aromatic hydrocarbon group having 6 to 10 carbon atoms having a heterocyclic group as a substituent. The compound according to [1], wherein R ² and R ⁴ represent saturated hydrocarbon groups having 1 to 20 carbon atoms or hydrogen atoms which may have substituents independently of each other.
[3] The compound according to [1] or [2], wherein the aromatic hydrocarbon group having 6 to 10 carbon atoms having the heterocyclic group is a group represented by the formula (1x).

[In formula (1x), Q ¹ represents a heterocyclic group. * Represents a bond with a nitrogen atom. ]
[4] The compound according to any one of [1] to [3], wherein the heterocyclic group is a heterocyclic group containing a nitrogen atom.
[5] A colored resin composition containing the compound and resin according to any one of [1] to [4].
[6] A color filter formed from the colored resin composition according to [5].
[7] A display device including the color filter according to [6].

When the colored resin composition contains the compound of the present invention as a colorant, a color filter having excellent contrast can be formed.

The compound of the present invention is represented by the formula (1). Hereinafter, the compound represented by the formula (1) may be referred to as "compound (1)". The compounds of the present invention also include tautomers thereof and salts thereof. In addition, each of the components and functional groups exemplified below can be used alone or in combination.

[In the formula (1), R ^{1 to} R ⁴ have a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a substituent independently of each other. It represents a good aromatic hydrocarbon group having 6 to 10 carbon atoms, and at least one represents an aromatic hydrocarbon group having 6 to 10 carbon atoms having a heterocyclic group as a substituent and is contained in the saturated hydrocarbon group. −CH ₂ − may be replaced with −O −, −CO− or −NR ^5−. R ¹ and R ² may be combined to form a ring containing a nitrogen atom, and R ³ and R ⁴ may be combined to form a ring containing a nitrogen atom.
R ^{5 to} R ⁷ represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other. ]

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms in R ^{1 to} R ⁴ include a phenyl group, a toluyl group, a xsilyl group, a mesityl group, a propylphenyl group and a butylphenyl group.

The aromatic hydrocarbon group substituent which may have a halogen ^{atom, -R 8, -OH, -OR 8} , -SO 3 -, -SO 3 H, -SO 3 - Z +, - Examples include CO ₂ H, -CO ₂ R ⁸ , -SR ⁸ , -SO ₂ R ⁸ , -SO ₃ R ⁸ , -SO ₂ NR ⁹ R ¹⁰ or heterocyclic groups, and these substituents are aromatic hydrocarbons. It is preferable to replace the hydrogen atom contained in the group. Among them, as the _{^{substituent, -SO 3 -, -SO 3 H}} , -SO 3 - Z + and -SO ₂ NR ⁹ R ¹⁰ is _{^{preferably, -SO 3 - Z +, -SO}} 2 NR 9 R 10 And heterocyclic groups are more preferred. In this case, as −SO ₃ ⁻ Z ⁺ , −SO ₃ ^{− +} N (R ¹¹ ) ₄ is preferable.
However, Z ^{+ _{is, + N (R 11) 4}} , represents Na ⁺ or K ^+, 4 one R ¹¹ may be the same or different.

The heterocyclic group may be a saturated heterocyclic group or an unsaturated heterocyclic group, and may be a monocyclic heterocyclic group or a fused ring heterocyclic group. The heterocyclic group preferably has 2 to 10 carbon atoms, and more preferably 3 to 8 carbon atoms.
Examples of the heterocyclic group include a heterocyclic group containing a nitrogen atom, a heterocyclic group containing an oxygen atom and not containing a nitrogen atom, and a heterocyclic group containing a sulfur atom and not containing a nitrogen atom.

Examples of the heterocyclic group containing a nitrogen atom include a zetidineyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a saturated heterocyclic group containing a nitrogen atom such as a thiomorpholinyl group; a pyrrolyl group, a pyrazolyl group, an imidazolyl group, 1, 2 , 3-triazolyl group, 1,2,4-triazolyl group, pyridinyl group, pyridadinyl group, pyrimidinyl group, pyrazinyl group, 1,3,5-triazinyl group, indolinyl group, isoindolinyl group, indolyl group, indridinyl group, benzoimidazolyl group , Kinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, naphthyldinyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, unsaturated heterocyclic group containing nitrogen atom such as benzothiazolyl group and the like. Be done.

Examples of the heterocycle containing an oxygen atom and not a nitrogen atom include an oxygen atom such as an oxetanyl group, a tetrahydrofuryl group, a tetrahydropyranyl group, a 1,3-dioxanyl group and a 1,4-dioxanyl group, and a nitrogen atom. Saturated heterocyclic group not contained; unsaturated heterocyclic group containing oxygen atom such as frill group, 2H-pyranyl group, 4H-pyranyl group, 1-benzofuryl group, chromanyl group, isochromanyl group and not containing nitrogen atom. Be done.

Examples of the heterocycle containing a sulfur atom and not containing a nitrogen atom include a saturated heterocyclic group containing a sulfur atom such as a thietanyl group, a thiolanyl group, a thianyl group, and a 1,3-dithianyl group and not containing a nitrogen atom; a thienyl group, Examples thereof include unsaturated heterocyclic groups containing a sulfur atom such as a 4H-thiopyranyl group and a benzothienyl group and not containing a nitrogen atom.

Among them, a heterocyclic group containing a nitrogen atom is preferable, and a saturated heterocyclic group containing a nitrogen atom is more preferable.

R ⁸ represents a saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
R ⁹ and R ¹⁰ represent saturated hydrocarbon groups having 1 to 20 carbon atoms which may have hydrogen atoms or substituents independently of each other, and are contained in the saturated aliphatic hydrocarbon groups −CH ₂ −. is, -O -, - CO -, - NH- or -NR ⁸ - may be replaced to, R ⁹ and R ^10, a heterocyclic ring bonded 3- to 10-membered ring containing a nitrogen atom together It may be formed.
R ¹¹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms in R ^{1 to} R ⁴ and R ^{8 to} R ¹¹ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group. , Nonyl group, decyl group, dodecyl group, hexadecyl group, icosyl group and other linear alkyl groups; isopropyl group, isobutyl group, isopentyl group, neopentyl group, 2-ethylhexyl group and other branched chain alkyl groups; cyclopropyl group , Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, tricyclodecyl group and other alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms.
The ^{hydrogen atom contained in the saturated hydrocarbon group in R 1 to} R ⁴ may be substituted with, for example, an aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom as a substituent. As the aromatic hydrocarbon group having 6 to 10 carbon atoms which may substitute the hydrogen atom of the saturated hydrocarbon group of ^{R 1 to} R ⁴ , the aromatic hydrocarbon group having 6 to 10 carbon atoms in ^{R 1 to} R ^{4 is used.} Examples thereof include groups similar to the groups exemplified as the groups.
The ^{hydrogen atom contained in the saturated hydrocarbon group in R 9} and R ¹⁰ may be substituted with, for example, a hydroxy group or a halogen atom as a substituent.

Examples of the ring formed by R ¹ and R ² together and the ring formed by R ³ and R ^{4 together include the following.} In the formula, * represents a bond.

Examples of −OR ⁸ include alkyloxy groups such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group and icosyloxy group. Can be mentioned.

Examples of −CO ₂ R ⁸ include alkyloxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, hexyloxycarbonyl group and icosyloxycarbonyl group.

Examples of −SR ⁸ include alkyl sulfanyl groups such as methyl sulfanyl group, ethyl sulfanyl group, butyl sulfanyl group, hexyl sulfanyl group, decyl sulfanyl group and icosyl sulfanyl group.
Examples of −SO ₂ R ⁸ include alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, butylsulfonyl group, hexylsulfonyl group, decylsulfonyl group and icosylsulfonyl group.
Examples of −SO ₃ R ⁸ include alkyloxysulfonyl groups such as methoxysulfonyl group, ethoxysulfonyl group, propoxysulfonyl group, tert-butoxysulfonyl group, hexyloxysulfonyl group and icosyloxysulfonyl group.

-SO ₂ NR ⁹ R ¹⁰ includes, for example, a sulfamoyl group;
N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butyl sulfamoyl group, N-tert-butyl sulfamoyl group, N-pentyl sulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-methylbutyl) sulfamoyl group, N- (2-methylbutyl) sulfamoyl group, N- (3) -Methylbutyl) sulfamoyl group, N-cyclopentyl sulfamoyl group, N-hexyl sulfamoyl group, N- (1,3-dimethylbutyl) sulfamoyl group, N- (3,3-dimethylbutyl) sulfamoyl group, N- Heptyl sulfamoyl group, N- (1-methylhexyl) sulfamoyl group, N- (1,4-dimethylpentyl) sulfamoyl group, N-octyl sulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- N-1-substituted sulfamoyl groups such as (1,5-dimethylhexyl) sulfamoyl group, N- (1,1,2,2-tetramethylbutyl) sulfamoyl group;
N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-propylmethylsulfamoyl group, N, N-isopropylmethylsulfa Moyl group, N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis (1-methylpropyl) sulfamoyl group, N, N-heptylmethylsulfamoyl Examples thereof include N, N-2 substituted sulfamoyl groups such as groups.

The _{^{R 5, -CO 2 H, -CO}} 2 - Z +, -CO 2 R 8, -SO 3 -, -SO 3 - Z +, -SO 3 H or -SO ₂ NHR ⁹ are preferred, -SO ^{_{3 -, -SO 3 - Z +}} , -SO 3 H or -SO ₂ NHR ⁹ is more preferable.

Examples of the alkyl group having 1 to 6 carbon atoms in R ^{5 to} R ⁷ include those having 1 to 6 carbon atoms among the alkyl groups listed above. Hydrogen atoms are preferable as R ⁶ and R ^7.

Examples of the aralkyl group having 7 to 10 carbon atoms in R ¹¹ include a benzyl group, a phenylethyl group, a phenylbutyl group and the like.

Z ⁺ is ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ¹¹ ) ₄ .
The ⁺ a N (R ¹¹⁾ _4, of the four R ^11, it is preferred that at least two of a saturated hydrocarbon group having 5 to 20 carbon atoms. The total number of carbon atoms of the four R ¹¹ is preferably 20 to 80, 20 to 60 is more preferable.

In compound (1), R ¹ represents an aromatic hydrocarbon group having 6 to 10 carbon atoms having a heterocyclic group as a substituent, and R ^{2 to} R ⁴ have substituents independently of each other. A saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon having 6 to 10 carbon ^{atoms in which R 1} and R ^{3 have a heterocyclic group as a substituent.} It is preferable that R ² and R ⁴ represent a group and independently represent a saturated hydrocarbon group having 1 to 20 carbon atoms or a hydrogen atom which may have a substituent.

As the aromatic hydrocarbon group having 6 to 10 carbon atoms having a heterocyclic group, the group represented by the formula (1x) is preferable.

[In formula (1x), Q ¹ represents a heterocyclic group. * Represents a bond with a nitrogen atom. ]

Examples of the heterocyclic group represented by Q ¹ include the same groups as those exemplified as the substituent of the aromatic hydrocarbon group represented by ^{R 1, and a heterocyclic group containing a nitrogen atom is preferable.} Saturated heterocyclic groups containing a nitrogen atom are more preferred.

The group represented by the formula (1x) is more preferably the group represented by the formula (1x-1).

[In the formula (1x-1), L ¹ represents an alkanediyl group having 3 to 10 carbon atoms, and −CH ₂ − contained in the alkanediyl group is changed to −O−, −S− or −NH−. It may be replaced. ]

The ^{alkanediyl group represented by L 1} is a linear alkanediyl group such as an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, and a pentane-1,5-diyl group. Can be mentioned. The ^{number of carbon atoms of the alkanediyl group represented by L 1} is preferably 3 to 8, and more preferably 4 to 6. As a group in which −CH ₂ − contained in the alkanediyl group is replaced with −O−, −S− or −NH−, * −CH ₂ CH ₂ −O−CH ₂ CH ₂₋ *, * −CH ₂ Examples thereof include _{CH 2-} S-CH ₂ CH _2- * or * -CH ₂ CH _2- NH-CH ₂ CH _{2- *.} However, * represents a bond with a nitrogen atom.
Of these, a group in which −CH ₂₋ contained in the alkanediyl group is replaced with −O− is preferable.

As the compound (1), a compound represented by the formula (2) (hereinafter, may be referred to as “compound (2)”) is preferable. Compound (2) may be a tautomer thereof.

[In the formula (2), R ^{21 to} R ²⁴ represent an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a hydrogen atom, −R ^{26 or a substituent independently of each other, and at least one.} One represents an aromatic hydrocarbon group having 6 to 10 carbon atoms and having a heterocyclic group as a substituent. R ²¹ and R ²² may be combined to form a ring containing a nitrogen atom, and R ²³ and R ²⁴ may be combined to form a ring containing a nitrogen atom.
R ²⁶ represents a saturated hydrocarbon group having 1 to 20 carbon atoms. ]

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms in R ^{21 to} R ²⁴ include the same groups as those mentioned as the aromatic hydrocarbon group in ^{R 1 to} R ^4. Hydrogen atoms contained in the aromatic hydrocarbon _{^{group, -SO 3 -, -SO 3 H}} , -SO 3 - Z1 +, -SO 3 R 26, substituted with -SO ₂ NHR ^26, or a heterocyclic group May be good.
Examples of the heterocyclic group include groups similar to the heterocyclic group exemplified as the substituent of the aromatic heterocyclic group represented by R ^{1, preferably a heterocyclic group containing a nitrogen atom, and saturation containing a nitrogen atom.} Heterocyclic groups are more preferred.
Z1 ⁺ represents ⁺ N (R ²⁷ ) ₄ , Na ⁺ or K ⁺ , and the four R ^27s may be the same or different.
R ²⁷ represents a saturated hydrocarbon group or a benzyl group having 1 to 20 carbon atoms.

As ^{a ring containing a nitrogen atom formed by R 21} and R ²² together, and a ring containing a nitrogen atom formed by R ²³ and R ²⁴ together, R ¹ and R ² are combined. The same as the ring to be formed can be mentioned. Of these, an aliphatic heterocycle is preferable. Examples of the aliphatic heterocycle include the following. In the formula, * represents a bond.

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms in R ²⁶ and R ²⁷ include the same groups as those mentioned as the saturated hydrocarbon group in ^{R 8 to} R ^11.
When R ^{21 to} R ²⁴ are -R ^26, it is preferable that -R ²⁶ is a methyl group or an ethyl group, respectively. As the R ²⁶ in -SO ₃ R ²⁶ and -SO ₂ NHR ^26, preferably branched chain alkyl group having 3 to 20 carbon atoms, more preferably a branched chain alkyl group having 6 to 12 carbon atoms, 2- Ethylhexyl groups are more preferred.

Z1 ⁺ is ⁺ N (R ²⁷ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ²⁷ ) ₄ .
The ⁺ a N (R ²⁷⁾ _4, among the four R ^27, it is preferred that at least two of a saturated hydrocarbon group having 5 to 20 carbon atoms. The total number of carbon atoms of the four R ²⁷ is preferably 20 to 80, 20 to 60 is more preferable.

In compound (2), R ²¹ represents an aromatic hydrocarbon group having 6 to 10 carbon atoms having a heterocyclic group as a substituent, and R ^{22 to} R ²⁴ are hydrogen atoms or −R independently of each other. ²⁶ is represented, or R ²¹ and R ²³ represent aromatic hydrocarbon groups having 6 to 10 carbon atoms having a heterocyclic group as a substituent, and R ²² and R ²⁴ are hydrogen independently of each other. It preferably represents an atom or -R ^26.
As the aromatic hydrocarbon group having 6 to 10 carbon atoms having a heterocyclic group, a group represented by the formula (1x) is preferable, and a group represented by the formula (1x-1) is more preferable.

Further, as the compound (1), a compound represented by the formula (3) (hereinafter, may be referred to as “compound (3)”) is also preferable. Compound (3) may be a tautomer thereof.

[In the formula (3), R ³¹ and R ³² represent saturated hydrocarbon groups having 1 to 10 carbon atoms independently of each other, and the hydrogen atom contained in the saturated hydrocarbon groups of ^{R 31} and R ^{32 is carbon.} It may be substituted with an aromatic hydrocarbon group having a number of 6 to 10 or a halogen atom, and the hydrogen atom contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 3 carbon atoms. is, -O - - the -CH ₂ - contained in the saturated hydrocarbon group R ^31, R ^32, - CO- or -NR ¹¹ - may be replaced with.
R ³³ and R ³⁴ independently represent an alkyl group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 4 carbon atoms or a heterocyclic group, and at least one of them represents. Represents a heterocyclic group.
R ³¹ and R ³³ may be combined to form a ring containing a nitrogen atom, and R ³² and R ³⁴ may be combined to form a ring containing a nitrogen atom.
p and q represent integers 0 to 5 independently of each other. When p is 2 or more, the plurality of R ^33s may be the same or different, and when q is 2 or more, the plurality of R ^34s may be the same or different. However, the total of p and q is 1 or more.
R ¹¹ has the same meaning as above. ]

Examples of the saturated hydrocarbon group having 1 to 10 carbon atoms in R ³¹ and R ³² include a group having 1 to 10 carbon atoms among those ^{in R 8.}
Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms that may have as a substituent include the same group ^{as that in R 1.}
Examples of the alkoxy group having 1 to 3 carbon atoms include a methoxy group, an ethoxy group, a propoxy group and the like.
R ³¹ and R ³² are preferably saturated hydrocarbon groups having 1 to 3 carbon atoms independently of each other.

Examples of the alkyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group and the like.
Examples of the alkylsulfanyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include a methyl sulfanyl group, an ethyl sulfanyl group, a propyl sulfanyl group, a butyl sulfanyl group, an isopropyl sulfanyl group and the like.
Examples of the alkylsulfonyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include a methyl sulfonyl group, an ethyl sulfonyl group, a propyl sulfonyl group, a butyl sulfonyl group and an isopropyl sulfonyl group.
Examples of the heterocyclic group in R ³³ and R ³⁴ include a group similar to the heterocyclic group exemplified as a substituent of the aromatic hydrocarbon group having 6 to 10 carbon atoms represented by ^{R 1, and contains a nitrogen atom.} A heterocyclic group is preferable, and a saturated heterocyclic group containing a nitrogen atom is more preferable.
As R ³³ and R ³⁴ , an alkyl group or a heterocyclic group having 1 to 4 carbon atoms is preferable, and a methyl group or a heterocyclic group is more preferable.

p and q are preferably integers of 0 to 2, preferably 0 or 1.

In compound (3), it is preferable that ^{at least one of R 33} and R ³⁴ is a heterocyclic group, and R ³³ and R ^{34 are heterocyclic groups.}

The compound (3) is preferably a compound represented by the formula (3-1).

[In equation (3-1), R ³¹ and R ³² are synonymous with the above. Q ³¹ and Q ³² represent heterocyclic groups independently of each other. ]

Examples of the heterocyclic group represented by Q ³¹ and Q ³² include a group similar to the heterocyclic group exemplified as a substituent of the aromatic hydrocarbon group represented by ^{R 1, and a heterocyclic group containing a nitrogen atom.} Is preferable, and a saturated heterocyclic group containing a nitrogen atom is more preferable.

The compound (3) is more preferably a compound represented by the formula (3-2).

[In equation (3-2), R ³¹ and R ³² are synonymous with the above. L ³¹ and L ³² independently represent an alkanediyl group having 3 to 10 carbon atoms, and -CH ₂ − contained in the alkanediyl group is replaced with -O-, -S- or -NH-. You may. ]

The ^{alkanediyl group represented by L 31} and L ³² and the group in which −CH ₂ − contained in the alkanediyl group is replaced with −O−, −S− or −NH− are represented by ^{L 1, respectively.} _{Examples of the group in which -CH 2} − contained in the alkanediyl group and the alkanediyl group is replaced with -O-, -S- or -NH- are the same groups as those exemplified, and the -CH contained in the alkanediyl group is included. _{A group in which 2} − is replaced with −O − is preferable. The ^{number of carbon atoms of the alkanediyl group represented by L 31} and L ³² is preferably 3 to 8, and more preferably 4 to 6.

Examples of the compound (1) include compounds (I-1) to (I-252) represented by the formula (I).

However, H represents a hydrogen atom, Me represents a methyl group, Et represents an ethyl group, Pr represents an n-propyl group, iPr represents a 2-propyl group, Bu represents an n-butyl group, and 2EH represents a 2-ethylhexyl group (p1). ~ (P4) represent the following groups, respectively. In the formula, * represents a bond.

(H1) to (h4) represent that R ^3a and R ^4a together form the following ring, respectively. In the formula, * represents a bond.

As the compound (1), compounds (I-1) to (I-7) and compounds (I-29) to (I-83) are preferable.

As a method for producing the compound (1), a compound represented by the formula (1x), a compound represented by the formula (1z-1) and a compound represented by the formula (1z-2) are used as an organic solvent. Examples thereof include a method of reacting in the presence or in the absence of a solvent. The reaction temperature is preferably 30 ° C. to 180 ° C., more preferably 50 ° C. to 110 ° C. The reaction time is preferably 1 to 12 hours, more preferably 3 to 8 hours.

[In the formula (1x), the formula (1z-1), the formula (1z-2) and the formula (1), R ^{1 to} R ⁷ have the same meanings as described above. ]

Examples of the organic solvent include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; alcohol solvents such as methanol, ethanol and butanol; nitro hydrocarbon solvents such as nitrobenzene; methylisobutyl ketones. Etc., such as a ketone solvent; and an amide solvent such as 1-methyl-2-pyrrolidone; and the like.

The amount of the compound represented by the formula (1z-1) and the compound represented by the formula (1z-2) is preferably 1 mol or more and 8 mol or more with respect to 1 mol of the compound represented by the formula (1x). It is not more than a mole, more preferably 1 mol or more and 5 mol or less. Each may be reacted stepwise or simultaneously.

When the compound (1) is a compound in which ^{any one of R 1 to} R ⁴ is a hydrogen atom (hereinafter, may be referred to as "compound (1a)"), the compound (1a) and the formula (1z-3) are used. ) May be further reacted in the presence of an organic solvent or in the absence of a solvent. The reaction temperature is preferably 30 ° C. to 180 ° C., more preferably 50 ° C. to 110 ° C. The reaction time is preferably 1 to 12 hours, more preferably 3 to 8 hours.

[In the formula (1z-3), R ¹² represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. ]

Examples of the organic solvent include the same solvents as those exemplified as the organic solvent for reacting the compound (1x) with the compounds (1z-1) and (1z-2).

When the compound (1a) and the compound represented by the formula (1z-3) are reacted, a basic substance such as sodium carbonate or potassium carbonate may coexist.

The method for obtaining the target compound (1) from the reaction mixture is not particularly limited, and various known methods can be adopted. For example, the reaction mixture can be mixed with water and the precipitated crystals can be collected by filtration. The temperature at which the reaction mixture and water are mixed is preferably 10 ° C. or higher and 50 ° C. or lower. After that, it is preferable to stir at the same temperature for about 0.5 to 2 hours. It is preferable that the collected crystals are washed with water or the like and then dried. If necessary, it may be further purified by a known method such as recrystallization.

The colored resin composition of the present invention contains compound (1) and a resin.
The content of the compound (1) is preferably 0.1 to 100 parts by mass, more preferably 1 to 50 parts by mass, and 1 to 20 parts by mass with respect to 100 parts by mass of the resin. Is even more preferable.

<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 unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (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 side. 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 anhydride, 3,4,5,6-tetrahydrophthalic anhydride, oxalic acid mono [2- (meth). ) Acryloyloxyethyl] and the like, preferably acrylic acid, methacrylic acid, maleic anhydride and the like.

In (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. ..
In addition, in this specification, "(meth) acrylic acid" represents at least one kind selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth) acryloyl" and "(meth) acrylate" have the same meaning.
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-. Examples thereof include (meth) acryloyloxymethyloxetane, tetrahydrofurfuryl (meth) acrylate, and the like, preferably glycidyl (meth) acrylate, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl ( Examples thereof include meth) acrylate and 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-. Examples thereof include 8-yl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene and the like, preferably. Examples thereof include styrene, vinyl toluene, N-phenylmaleimide, N-cyclohexylmaleimide, and N-benzylmaleimide.

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). 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 dispersity [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, 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 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 55% by mass with respect to the total amount of solids.

<Colorant (A)>
The colored resin composition of the present invention may contain a dye (A1) and a pigment (A2) in addition to the compound (1) as the colorant (A).

The dye (A1) is not particularly limited, and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified by the Color Index (published by The Society of Dyers and Colorists) as having hues other than pigments, and known dyes described in dyeing notes (color dyeing company). Be done. According to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acrydin dyes, styryl dyes, coumarins. Examples include dyes, quinoline dyes and nitro dyes. Of these, organic solvent-soluble dyes are preferred. Further, as the dye, the dyes described in JP-A-2015-28121, JP-A-2013-7032, JP-A-2013-144724, and JP-A-2013-53292 are also preferable.

As the pigment (A2), a known pigment can be used without particular limitation, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists).
Examples of the pigment include 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, 137, 138, 139, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 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, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 and other red pigments;
C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments; C.I. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet color pigments;
And so on.

When the colored resin composition of the present invention is a blue colored resin composition, the pigment is preferably at least one selected from the group consisting of blue pigments and violet colored pigments. When the colored resin composition of the present invention is a red colored resin composition, the pigment is preferably at least one selected from the group consisting of yellow pigments, orange pigments and red pigments.

The content of the colorant (A) is preferably 0.1 to 60% by mass, more preferably 0.5 to 55% by mass, still more preferably 1 to 50% by mass, based on the total amount of solids. %.
The content of the compound (1) is preferably 50% by mass or more, more preferably 80% by mass or more, and further preferably 90% by mass or more, based on the total amount of the colorant (A).
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 solids and the content of each component relative to the total amount can be measured by a known analytical means such as liquid chromatography or gas chromatography.

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

<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.

Among them, 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 (). 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.

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

<Polymerization 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, etc. 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-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl). ) Octane-1-on-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, 2-methyl-2-morpholino-1-( 4-Methylsulfanylphenyl) Propane-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-one, 1-hydroxycyclohexylphenylketone, 2,4-bis (trichloromethyl) ) -6-Piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoyldiphenylphosphenyl oxide, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenyl Biimidazole and the like can be mentioned.

When the polymerization initiator (D) is contained, the content of the polymerization initiator (D) is preferably 0.1 to 30% by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Parts, more preferably 1 to 20 parts by mass. 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 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 a polymerizable compound whose polymerization has been 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 initiator (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. , N-Phenylglycine and the like.

When these polymerization initiators (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, based on 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 (E).

<Solvent (E)>
The solvent (E) is not particularly limited, and a solvent usually used in the art can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule and not containing -COO-), ether ester solvent (solvent in the molecule). 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 (E) 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. (Solvent containing -COO- in the molecule 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. (containing -O- in the molecule and not containing -COO-) solvent);
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- in the molecule and not -COO-);
Alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents containing OH in the molecule and not containing -O-, -CO-, and -COO-);
Examples thereof include amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone.

As the solvent (E), propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, N-methylpyrrolidone and ethyl 3-ethoxypropionate are more preferable.

When the solvent (E) is contained, the content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored resin composition of the present invention. .. In other words, the total 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 display characteristics tend to be good because the color density is not insufficient when the color filter is formed. ..

<Other ingredients>
The colored fat composition of the present invention is, if necessary, an addition known in the art such as a leveling agent, a filler, other polymer compounds, 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 contains a colorant (A), a resin (B), and a polymerizable compound (C), a polymerization initiator (D), a solvent (E), and other components used as necessary. It can be prepared by mixing.

<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. Above all, the photolithography method is preferable.

When the colored resin composition contains the compound of the present invention as a colorant, a color filter having particularly excellent contrast can be produced. 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 be adapted to the gist of the above 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.
In the following, unless otherwise specified, "part" means "part by mass" and "%" means "% by mass".

Example 1
5.1 parts of the compound represented by the formula (1x-1) and 4.9 parts of 4-morpholinoaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to 30 parts of N-methyl-2-pyrrolidone at 70 ° C. The mixture was stirred for 5 hours. After cooling the above reaction solution to room temperature, 100 parts of water was added, and the mixture was stirred for 1 hour. The precipitated crystals were suction-filtered, washed 3 times with 100 parts of water, and the crystals were dried under reduced pressure to obtain 6.0 parts of the compound represented by the formula (I-1).

Next, 4.1 parts of the compound represented by the formula (I-1), 4.4 parts of 1-bromopropane (manufactured by Tokyo Chemical Industry Co., Ltd.) and 5.0 parts of potassium carbonate were added to N-methyl-2-pyrrolidone. It was added to 30 parts and stirred at 80 ° C. for 4 hours. After cooling the above reaction solution to room temperature, 100 parts of water was added, and the mixture was stirred for 1 hour. The precipitated crystals were suction-filtered, washed 3 times with 100 parts of water, and the crystals were dried under reduced pressure to obtain 4.5 parts of the compound represented by the formula (I-4).

Example 2
50.0 parts of the compound represented by the formula (1x-1) and 350 parts of isopropyl alcohol are mixed at room temperature, and 18.1 parts of diethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) is added to the mixture at a temperature not exceeding 20 ° C. Was added dropwise, and the mixture was stirred at 20 ° C. for 3 hours. The reaction solution was added to 2100 parts of 10% hydrochloric acid. The obtained precipitate was obtained as a residue of suction filtration, washed and dried with 373 parts of ion-exchanged water, and 23.6 parts of the compound represented by the formula (1y-1) was obtained.

Next, 6.6 parts of the compound represented by the formula (1y-1), 5.0 parts of 4-morpholinoaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), and 10.4 parts of potassium carbonate were added to N-methyl-2-. It was added to 30 parts of pyrrolidone and stirred at 80 ° C. for 5 hours. After cooling the above reaction solution to room temperature, 100 parts of water was added, and the mixture was stirred for 1 hour. The precipitated crystals were suction-filtered, washed 3 times with 100 parts of water, and the crystals were dried under reduced pressure to obtain 6.0 parts of the compound represented by the formula (I-30).

Further, 4.1 parts of the compound represented by the formula (I-30), 2.6 parts of 1-bromopropane (manufactured by Tokyo Chemical Industry Co., Ltd.) and 2.9 parts of potassium carbonate are added to N-methyl-2-pyrrolidone. It was added to 30 parts and stirred at 80 ° C. for 1 hour. After cooling the above reaction solution to room temperature, 100 parts of water was added, and the mixture was stirred for 1 hour. The precipitated crystals were suction-filtered, washed 3 times with 100 parts of water, and the crystals were dried under reduced pressure to obtain 4.0 parts of the compound represented by the formula (I-54).

Synthesis example 1
Nitrogen was flowed at 0.02 L / min into a flask equipped with a stirrer, a thermometer, a reflux condenser, and a dropping funnel to create a nitrogen atmosphere, and 305 parts of propylene glycol monomethyl ether acetate was added and heated to 70 ° C. with stirring. bottom. Next, 60 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decylacrylate (compound represented by the formula (I-1) and represented by the formula (II-1)). The compounds are mixed at a molar ratio of 50:50.) 440 parts were dissolved in 140 parts of propylene glycol monomethyl ether acetate to prepare a solution, and the solution was prepared using a dropping funnel over 4 hours. The mixture was dropped into a flask kept warm at 70 ° C.

On the other hand, a solution prepared by dissolving 30 parts of the polymerization initiator 2,2'-azobis (2,4-dimethylvaleronitrile) in 225 parts of propylene glycol monomethyl ether acetate was placed in a flask over 4 hours using another dropping funnel. Dropped. After the addition of the solution of the polymerization initiator is completed, 4 hours, kept at 70 ° C., then cooled to room temperature, and the weight average molecular weight (Mw), 9.1 × 10 ^3, the degree of dispersion 2.16, A resin B1 solution having a solid content of 34.8% and an acid value of 81 mg-KOH / g in terms of solid content was obtained. Resin B1 has the structural units shown below.

The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin obtained in the synthetic example were measured by using the GPC method under the following conditions.
Equipment: K2479 (manufactured by Shimadzu Corporation)
Column; SHIMADZU Shima-pack GPC-80M
Column temperature; 40 ° C
Solvent; THF (tetrahydrofuran)
Flow velocity; 1.0 mL / min
Detector; Standard material for RI calibration; 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.

Examples 3 and 4 and Comparative Example 1
(Preparation of colored resin composition)
Each component was mixed with the following composition to obtain a colored resin composition.

In Table 1, each component represents the following compound.
(A-1): Compound represented by formula (I-4) (A-2): Compound represented by formula (I-54) (A-3): Represented by formula (1-x) Compound

(B-1): Resin B1 (in terms of solid content)
(C-1): Dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)
(D-1): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE 01; manufactured by BASF)
(E-1): N-methylpyrrolidone (E-2): Propylene glycol monomethyl ether acetate

<Making a colored pattern>
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 obtain a colored composition layer. After allowing to cool, the distance between the substrate on which the colored composition layer was formed and the quartz glass photomask was set to 100 μm, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used in an air atmosphere at 150 mJ / cm. Light was irradiated with an exposure amount of ^{2 (based on 365 nm).} As the photomask, a photomask having a 100 μm line-and-space pattern formed was used. The colored composition layer after light irradiation is immersed and developed in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 24 ° C. for 60 seconds, washed with water, and then in an oven at 230. Post-baking was performed at ° C. for 20 minutes to obtain a coloring pattern.

<Light resistance evaluation>
An ultraviolet cut filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co., Ltd .; cuts light of 380 nm or less) is placed on the colored patterns obtained in Examples 3 and 4 and Comparative Example 1, and a light resistance tester (SUNTEST) is placed. CPS +: manufactured by Toyo Seiki Co., Ltd.) was irradiated with xenon lamp light for 24 hours.
The chromaticity of the coloring pattern after irradiation was measured, and the color difference before and after irradiation was determined. The results are shown in Table 7.

<Contrast evaluation>
Contrast meter (CT-1; manufactured by Tsubosaka Electric Co., Ltd., color difference meter BM-5A; manufactured by Topcon, light source; F-10, polarized light) for the coloring patterns obtained in Examples 3 and 4 and Comparative Example 1. The contrast was measured using a film (manufactured by Tsubosaka Electric Co., Ltd.) with a blank value of 30,000. The results are shown in Table 7.

By containing the compound of the present invention as a colorant, a color filter having particularly excellent contrast can be produced. 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.

Claims (4)

A compound represented by the formula (1).

[In equation (1),
R ¹ represents any one group selected from the group consisting of the following (p1) to (p4), and R ^{2 to} R ⁴ may have substituents independently of each other. Represents a saturated hydrocarbon group of number 1 to 20 or a hydrogen atom, or
R ¹ and R ³ represent any one group selected from the group consisting of the following (p1) to (p4) independently of each other ^{, and R 2} and R ^{4 independently represent substituents.} Represents a saturated hydrocarbon group having 1 to 20 carbon atoms or a hydrogen atom which may have a hydrogen atom.
_{-CH 2} − contained in the saturated hydrocarbon group may be replaced with −O −, −CO− or −NR ^5−.
R ³ and R ⁴ may be combined to form a ring containing a nitrogen atom.
R ^{5 to} R ⁷ represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other. ]

[In the formula, * represents a bond. ] Colored resin composition containing the compound and a resin according to claim 1. A color filter formed from the colored resin composition according to claim 2. A display device including the color filter according to claim 3.