JP6824202B2 - Colored resin composition - Google Patents

Description

The present invention relates to a colored resin composition.

Color filters used in display devices such as liquid crystal display devices, electroluminescence display devices and plasma displays, and solid-state image sensors such as CCDs and CMOS sensors are manufactured from colored resin compositions. Although the characteristics required for color filters used in display devices and solid-state image sensors are completely different, a photosensitive resin composition is used in the manufacturing process of printed wiring boards, and this photosensitive resin composition is mycalite. It may be colored with green oxalate or the like (Patent Document 1).

Japanese Unexamined Patent Publication No. 8-152710

Conventionally known colored resin compositions for color filters and photosensitive resin compositions for producing printed wiring boards have not been satisfactory in heat resistance and light resistance. An object of the present invention is to improve the heat resistance and light resistance of the colored resin composition.

The present invention includes the following inventions.
[1] Contains colorants and resins
A colored resin composition in which the colorant contains a compound represented by the formula (Ia).

［式（Ｉａ）中、
Ｒ¹〜Ｒ⁶は、それぞれ独立に、水素原子、置換基を有していてもよい炭素数１〜２０の炭化水素基、ＣＯＯ^-、又はＳ（Ｏ）₂Ｏ^-を表し、Ｒ²とＲ³及びＲ⁴とＲ⁵は、互いに結合して、置換基を有していてもよい芳香族炭化水素環又は置換基を有していてもよい芳香族複素環を形成してもよい。
Ｒ⁷は、置換基を有していてもよい炭素数６〜２０の芳香族炭化水素基又は置換基を有していてもよい炭素数３〜１９の芳香族複素環基を表し、Ｒ³又はＲ⁴と結合して、環を形成してもよい。
Ｒ⁸、Ｒ⁹は、それぞれ独立に、水素原子、置換基を有していてもよい炭素数１〜２０の炭化水素基、ＣＯＯ^-、又はＳ（Ｏ）₂Ｏ^-を表し、Ｒ⁸とＲ⁹は、互いに結合して置換基を有していてもよい環を形成してもよい。
Ｒ¹⁰〜Ｒ¹³は、それぞれ独立に、水素原子、置換基を有していてもよい炭素数１〜２０の脂肪族炭化水素基、置換基を有していてもよい炭素数６〜２０の芳香族炭化水素基又は置換基を有していてもよい炭素数３〜１９の芳香族複素環基を表し、Ｒ¹⁰とＲ¹¹、Ｒ¹²とＲ¹³、Ｒ²とＲ¹⁰及びＲ⁵とＲ¹²は、互いに結合して環を形成してもよい。
ａは、１又は２を表す。
ｂは、０又は１を表す。
Ｘ^ａ-は、ａ価のアニオンを表す。］
［２］ さらに、重合性化合物及び重合開始剤を含む前記［１］記載の着色樹脂組成物。
［３］ 前記［２］記載の着色樹脂組成物から形成されるカラーフィルタ。
［４］ 前記［３］記載のカラーフィルタを含む表示装置。

[In formula (Ia),
R ^{1 to} R ⁶ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, COO ⁻ , or S (O) ₂ O ⁻ , and R ² and R ³ and R ⁴ and R ⁵ may be bonded to each other to form an aromatic hydrocarbon ring which may have a substituent or an aromatic hetero ring which may have a substituent.
R ⁷ represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having ³ to 19 carbon atoms which may have a substituent, and R ³ Alternatively, it may be combined with R ⁴ to form a ring.
R ^8, R ⁹ are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms that may have a substituent group, COO ^-, or S (O) ₂ O ^- represents a R ⁸ R ⁹ may be bonded to each other to form a ring which may have a substituent.
R ^{10 to} R ¹³ independently have a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and 6 to 20 carbon atoms which may have a substituent. Represents an aromatic heterocyclic group having 3 to 19 carbon atoms which may have an aromatic hydrocarbon group or a substituent, and includes R ¹⁰ and R ¹¹ , R ¹² and R ¹³ , R ² and R ¹⁰ and R ⁵ . R ¹² may combine with each other to form a ring.
a represents 1 or 2.
b represents 0 or 1.
^Xa- represents an a-valent anion. ]
[2] The colored resin composition according to the above [1], which further contains a polymerizable compound and a polymerization initiator.
[3] A color filter formed from the colored resin composition according to the above [2].
[4] A display device including the color filter according to the above [3].

According to the colored resin composition of the present invention, a color filter having excellent heat resistance and light resistance can be produced.

The colored resin composition of the present invention contains a colorant and a resin. Hereinafter, the colorant may be referred to as "colorant (A)", and the resin may be referred to as "resin (B)".
(1) Colorant (A)
The colorant (A) contains a compound represented by the formula (Ia). Hereinafter, the compound represented by the formula (Ia) may be referred to as “compound (Ia)”.

[In formula (Ia),
R ^{1 to} R ⁶ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, COO ⁻ , or S (O) ₂ O ⁻ , and R ² and R ³ and R ⁴ and R ⁵ may be bonded to each other to form an aromatic hydrocarbon ring which may have a substituent or an aromatic hetero ring which may have a substituent.
R ⁷ represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having ³ to 19 carbon atoms which may have a substituent, and R ³ Alternatively, it may be combined with R ⁴ to form a ring.
R ^8, R ⁹ are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms that may have a substituent group, COO ^-, or S (O) ₂ O ^- represents a R ⁸ R ⁹ may be bonded to each other to form a ring which may have a substituent.
R ^{10 to} R ¹³ independently have a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and 6 to 20 carbon atoms which may have a substituent. Represents an aromatic heterocyclic group having 3 to 19 carbon atoms which may have an aromatic hydrocarbon group or a substituent, and includes R ¹⁰ and R ¹¹ , R ¹² and R ¹³ , R ² and R ¹⁰ and R ⁵ . R ¹² may combine with each other to form a ring.
a represents 1 or 2.
b represents 0 or 1.
^Xa- represents an a-valent anion. ]

Compound (Ia) is -COO ^- or -S (O) ₂ O ^-, then a the number is 1 in total. -COO ^- or -S (O) ₂ O ^- If the having 1 in total, b is zero. -COO ^- and -S (O) ₂ O ^- If no, b is 1. When b = 1, a becomes 1 or 2.

The hydrocarbon groups having 1 to 20 carbon atoms represented by R ^{1 to} R ⁶ and R ^{8 to} R ⁹ may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be an aliphatic hydrocarbon group. , Saturated or unsaturated, may be chain or alicyclic.
Saturated or unsaturated chain hydrocarbon groups represented by R ^{1 to} R ⁶ and R ^{8 to} R ⁹ include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group and octyl group. , Nonyl group, decyl group, undecyl group, dodecyl group, heptadecyl group, octadecyl group, icosyl group and other linear alkyl groups; isopropyl group, (2-methyl) propyl group, isobutyl group, sec-butyl group, tert -Butyl group, (2-ethyl) butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl) pentyl group, (2-methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group Branched chain alkyl groups such as ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group, and (3-ethyl) heptyl group; vinyl group, 1-propenyl group, etc. 2-Propenyl group (allyl group), isopropenyl group, (1-methyl) ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1- (2-propenyl)) ethenyl group, Alkenyl groups such as (1,2-dimethyl) propenyl group and 2-pentenyl group; and the like. The saturated or unsaturated chain hydrocarbon group preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, still more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 5 carbon atoms.

Saturated or unsaturated alicyclic hydrocarbon groups represented by R ^{1 to} R ⁶ and R ^{8 to} R ⁹ include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and cycloheptyl. Group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2, 2-Dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3 , 3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 4-cyclohexylcyclohexyl group and other cycloalkyl groups; cyclohexenyl groups (eg, cyclohex-2-ene, cyclohexa-3-3) En), cycloalkenyl groups such as cycloheptenyl group, cyclooctenyl group; bridging ring hydrocarbon groups such as norbornan group, adamantyl group, bicyclo [2.2.2] octyl group; cyclopropylmethyl group, cyclopropylethyl group, cyclo An alkyl group to which one or more cycloalkyl groups such as a butylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, and a cyclohexylethyl group are bonded; and the like can be mentioned. The alicyclic hydrocarbon group preferably has 3 to 20 carbon atoms, more preferably 4 to 15 carbon atoms, still more preferably 5 to 15 carbon atoms, and particularly preferably 5 to 10 carbon atoms.

The aromatic hydrocarbon groups represented by R ^{1 to} R ⁶ and R ^{8 to} R ⁹ are phenyl group, o-tolyl group, m-tolyl group, p-tolyl 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, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, mesityl group, 2,6-bis (2-propyl) phenyl group, 2,4 6-trimethylphenyl group, cyclohexylmethylphenyl group, benzylphenyl group, (dimethyl (phenyl) methyl) phenyl group, 1-naphthyl group, 2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, Examples thereof include 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, phenylphenyl group and phenylphenylphenyl group. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 20, and more preferably 6 to 15.

The aromatic hydrocarbon groups represented by R ^{1 to} R ⁶ and R ^{8 to} R ⁹ include at least one of the above-mentioned chain hydrocarbon groups, cyclic hydrocarbon groups, and aromatic hydrocarbon groups. It may be a group combined with the aromatic hydrocarbon group mentioned above, and is an aralkyl group such as a benzyl group, a phenylmethyl group, a 1-methyl-1-phenylethyl group; a phenylethenyl group (phenylvinyl group) and the like. The arylalkenyl group of the above; an arylalkynyl group such as a phenylethynyl group; and the like; the carbon number thereof is preferably 7 to 20, and more preferably 7 to 15.

The hydrocarbon groups represented by R ^{1 to} R ⁶ and R ^{8 to} R ⁹ may have one or more substituents. Examples of the substituent include a halogen ^{atom, -OH, -OR 16, -S (} O) 2 O -, -S (O) 2 OH, -S (O) 2 O - Z +, -C (O) O - , -C (O) OH, -C (O) O ^- Z ⁺ , -C (O) OR ¹⁶ , -C (O) NHR ¹⁶ , -C (O) NR ¹⁶ R ¹⁷ , -SR ¹⁶ , -S (O) ₂ R ¹⁶ , -S (O) ₂ OR ¹⁶ , -S (O) ₂ NH ₂ , -S (O) ₂ NHR ¹⁶ , -S (O) ₂ NR ¹⁶ R ¹⁷ (in the formula, R ¹⁶ And R ¹⁷ each independently represent a hydrocarbon group having 1 to 20 carbon atoms). Among them, as the ^{_{substituent, -S (O) 2 O -}} , -S (O) 2 OH, -S (O) 2 O - Z +, -S (O) 2 NH 2, -S (O ) ₂ NHR ¹⁶ , -SO ₂ NR ¹⁶ R ¹⁷ , preferably -S (O) ₂ O ^- Z ⁺ , -S (O) ₂ NH ₂ , -S (O) ₂ NHR ¹⁶ , -SO ₂ NR ¹⁶ R ¹⁷ is more preferable.

Examples of the halogen atom as the substituent include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and a fluorine atom, a chlorine atom and the like are preferable.

Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R ¹⁶ and R ¹⁷ include the same hydrocarbon groups represented by R ^{1 to} R ⁶ and R ^{8 to} R ⁹ .
As −OR ¹⁶ , methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, icosyloxy group and the like are preferable.

As -C (O) OR ¹⁶ , methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, hexyloxycarbonyl group, icosyloxycarbonyl group and the like are preferable.

-C (O) NHR ¹⁶ includes N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec- Butylcarbamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N- (1-ethylpropyl) carbamoyl group, N- (1,1-dimethylpropyl) carbamoyl group, N- (1,2-dimethyl) Propyl) carbamoyl group, N- (2,2-dimethylpropyl) carbamoyl group, N- (1-methylbutyl) carbamoyl group, N- (2-methylbutyl) carbamoyl group, N- (3-methylbutyl) carbamoyl group, N- Cyclopentyl carbamoyl group, N-hexyl carbamoyl group, N- (1,3-dimethylbutyl) carbamoyl group, N- (3,3-dimethylbutyl) carbamoyl group, N-heptyl carbamoyl group, N- (1-methylhexyl) Carbamoyl group, N- (1,4-dimethylpentyl) carbamoyl group, N-octylcarbamoyl group, N- (2-ethylhexyl) carbamoyl group, N- (1,5-dimethyl) hexylcarbamoyl group, N- (1,5-dimethyl) 1,2,2-tetramethylbutyl) carbamoyl group and the like are preferable.

-C (O) NR ¹⁶ R ¹⁷ includes N, N-dimethylcarbamoyl group, N, N-ethylmethylsulcarbamoyl group, N, N-diethylcarbamoyl group, N, N-propylmethylcarbamoyl group, N, N. -Isopropylmethylcarbamoyl group, N, N-tert-butylmethylcarbamoyl group, N, N-butylethylcarbamoyl group, N, N-bis (1-methylpropyl) carbamoyl group, N, N-heptylmethylcarbamoyl group, etc. preferable.

As −SR ¹⁶ , methylsulfanil group, ethylsulfanil group, butylsulfanil group, hexylsulfanil group, decylsulfanil group, icosylsulfanil group and the like are preferable.

As −S (O) ₂ R ¹⁶ , methyl sulfonyl group, ethyl sulfonyl group, butyl sulfonyl group, hexyl sulfonyl group, decyl sulfonyl group, icosyl sulfonyl group and the like are preferable.
As the −S (O) ₂ OR ¹⁶ , methoxysulfonyl group, ethoxysulfonyl group, propoxysulfonyl group, tert-butoxysulfonyl group, hexyloxysulfonyl group, icosyloxysulfonyl group and the like are preferable.

-S (O) ₂ NHR ¹⁶ includes N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group. , N-isobutylsulfamoyl group, N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl 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- (1,5-dimethyl) hexyl sulfamoyl group, N- (1,1,2,2-tetramethylbutyl) sulfamoyl group and the like are preferable.

-S (O) ₂ NR ¹⁶ R ¹⁷ includes N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-propylmethyl. Sulfamoyl group, N, N-isopropylmethylsulfamoyl group, N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis (1-methylpropyl) ) Sulfamoyl group, N, N-heptylmethylsulfamoyl group and the like are preferable.

Z ⁺ is ⁺ N (R ¹⁸ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ¹⁸ ) ₄ . R ¹⁸ is a hydrocarbon group having 1 to 20 carbon atoms, and is preferably a saturated hydrocarbon group. Four R ¹⁸ that binds to N may be different from each other, of the four R ^18, it is preferred that at least two of a monovalent saturated hydrocarbon group having 5 to 20 carbon atoms. The total number of carbon atoms of the four R ¹⁸ is preferably 20 to 80, 20 to 60 is more preferable.
^{As +} N (R ¹⁸ ) ₄ , the following is preferable.

Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R ⁷ and R ^{10 to} R ¹³ include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, and a xsilyl group (for example, 2). , 4-kisilyl group, 2,6-kisilyl group, etc.), 4-n-butylphenyl group, 4-tert-butylphenyl group, naphthyl group, anthryl group, phenanthryl group, phenylphenyl group, phenylphenylphenyl group, etc. Phenyl group, o-tryl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, 2,6-xylyl group, 4-n-butylphenyl group, 4-tert- Examples thereof include a butylphenyl group, and more preferably a 2,4-xysilyl group, a 4-n-butylphenyl group, and a phenyl group. The number of carbon atoms of the aromatic hydrocarbon groups represented by R ⁷ and R ^{10 to} R ¹³ is preferably 6 to 15, and more preferably 6 to 12.

Examples of the aromatic heterocyclic group having 3 to 19 carbon atoms represented by R ⁷ and R ^{10 to} R ¹³ include a frill group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, a pyridyl group and an indolyl group. Examples thereof include an isoindrill group and an indazolyl group. The number of carbon atoms of the aromatic heterocyclic group represented by R ⁷ and R ^{10 to} R ¹³ is preferably 3 to 12, and more preferably 3 to 8.

The aromatic hydrocarbon group having 6 to 20 carbon atoms and the aromatic heterocyclic group having 3 to 19 carbon atoms represented by R ⁷ and R ^{10 to} R ¹³ have one or more substituents. May be good. Examples of this substituent include substituents similar to those represented by hydrocarbon groups having 1 to 20 carbon atoms represented by R ^{1 to} R ⁶ and R ^{8 to} R ⁹ .

The aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R ^{10 to} R ¹³ may be saturated or unsaturated, or may be a chain or an alicyclic. Saturated or unsaturated chain hydrocarbon groups represented by R ^{10 to} R ¹³ include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and decyl group. , Undecyl group, dodecyl group, heptadecyl group, octadecyl group, linear alkyl group such as icosyl group; isopropyl group, (2-methyl) propyl group, isobutyl group, sec-butyl group, tert-butyl group, (2) -Ethyl) Butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl) pentyl group, (2-methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, isohexyl Branched alkyl groups such as groups, (5-methyl) hexyl groups, (2-ethyl) hexyl groups, and (3-ethyl) heptyl groups; vinyl groups, 1-propenyl groups, 2-propenyl groups (allyl). Group), isopropenyl group, (1-methyl) ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1- (2-propenyl)) ethenyl group, (1,2-dimethyl) ) Alkenyl groups such as propenyl group and 2-pentenyl group; and the like. The saturated or unsaturated chain hydrocarbon group preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, still more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 5 carbon atoms.

Saturated or unsaturated alicyclic hydrocarbon groups represented by R ^{10 to} R ¹³ include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl. Group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl Group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group and 3,3,5,5 -Cycloalkyl groups such as tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 4-cyclohexylcyclohexyl group; cyclohexenyl group (eg, cyclohex-2-ene, cyclohexa-3-ene), cycloheptenyl group, Cycloalkenyl groups such as cyclooctenyl group; norbornan group, adamantyl group, bicyclo [2.2.2] octyl group; cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentyl An alkyl group to which one or more cycloalkyl groups such as an ethyl group, a cyclohexylmethyl group, and a cyclohexylethyl group are bonded; and the like can be mentioned. The alicyclic hydrocarbon group preferably has 3 to 20 carbon atoms, more preferably 4 to 20 carbon atoms, still more preferably 4 to 15 carbon atoms, still more preferably 5 to 15 carbon atoms, and particularly preferably 5 to 15 carbon atoms. It is 5 to 10, and among them, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group are particularly preferable.

The aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R ^{10 to} R ¹³ may have one or two or more substituents. Examples of this substituent include substituents similar to those represented by hydrocarbon groups having 1 to 20 carbon atoms represented by R ^{1 to} R ⁶ and R ^{8 to} R ⁹ .

R ¹⁰ and R ¹¹ are a combination in which both are aliphatic hydrocarbon groups having 1 to 20 carbon atoms which may independently have a substituent (hereinafter referred to as combination 1), and both have an independent substituent. A combination that may be an aromatic hydrocarbon group having 6 to 20 carbon atoms (hereinafter referred to as combination 2), one of which is an aliphatic hydrocarbon group having 1 to 20 carbon atoms that may have a substituent, and the other. Is preferably a combination (hereinafter referred to as combination 3) which becomes an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and combination 1 and combination 3 are more preferable. Also in R ¹² and R ¹³ , combination 1, combination 2, combination 3 and the like are preferable, and combination 1 and combination 3 are more preferable. According to the combination 1, the heat resistance of the compound (Ia) becomes better, and according to the combination 3, the light resistance of the compound (Ia) becomes better.

An aromatic hydrocarbon ring that may have a substituent formed by bonding R ² and R ³ or R ⁴ and R ⁵ to each other and an aromatic heterocycle that may have a substituent include R. ^A ring similar to an aromatic hydrocarbon ring having 6 to 20 carbon atoms which may have a substituent represented by ⁷ and R ^{10 to} R ¹³ , or represented by R ⁷ and R ^{10 to} R ^13. Examples thereof include rings similar to aromatic heterocycles having 3 to 19 carbon atoms which may have a substituent.

The ring formed by combining R ⁷ and R ³ and the ring formed by combining R ⁷ and R ⁴ include a cyclopentane ring, a cyclopentene ring, a cyclopentadiene ring, a cyclohexane ring, a cyclohexene ring, and a cyclohexadiene ring. , Pyran ring, dihydropyrrole ring, pyrrolidine ring, furan ring, dihydrofuran ring, tetrahydrofuran ring, pyran ring, dihydropyran ring, tetrahydropyran ring, dihydropyridine ring, tetrahydropyridine ring, piperidine ring, thiacyclopentene ring, thiacyclopentadiene ring , Thiacyclohexene ring, thiacyclohexadiene ring and the like.

Rings formed by combining R ⁸ and R ⁹ include cyclopentane rings, cyclohexane rings, cycloheptane rings, and other cycloalkane rings having 4 to 8 carbon atoms; aziridine rings, azetidine rings, pyrrolidine rings, piperidine rings, and the like. Nitrogen-containing monocyclic saturated heterocycle with 2 to 6 carbon atoms such as piperazine ring; carbon number of oxylan ring, oxetane ring, tetrahydrofuran ring, tetrahydropyran ring, 1,3-dioxane ring, 1,4-dioxane ring, etc. An oxygen-containing monocyclic saturated heterocycle having a value of 2 to 6; a sulfur-containing monocyclic saturated heterocycle having 2 to 6 carbon atoms such as a tetrahydrothiophene ring and a dithiolane ring can be mentioned.

Examples of the ring formed by connecting R ¹⁰ and R ¹¹ and R ¹² and R ¹³ to each other include the following. In the formula, * represents a bond (single bond or double bond) with a carbon atom to which the identification code of c10 or c2 is assigned in the formula (Ia'). The formula (Ia') is a formula in which an identification code is assigned to the carbon of the compound represented by the formula (Ia).

Examples of the ring formed by combining R ² and R ¹⁰ include the ring represented by the group [a1]. The formula (Ia') has the same meaning as described above. Among the carbon atoms constituting the ring represented by the group [a1], the carbon atom to which the identification code is assigned corresponds to the carbon atom to which the same identification code is assigned in the formula (Ia'). In the formula, * represents a bond.

Examples of the ring formed by combining R ⁵ and R ¹² include the rings represented by the group [a2]. The formula (Ia') has the same meaning as described above. Among the carbon atoms constituting the ring represented by the group [a2], the carbon atom to which the identification code is assigned corresponds to the carbon atom to which the same identification code is assigned in the formula (Ia'). In the formula, * represents a bond.

The anion represented by ^{X a-, F -, Cl -} , Br -, BF 4 -, PF 6 -, anions represented by formula (IIa), the anion represented by the formula (IIb), formula ( Examples thereof include an anion represented by IID (IIc), an anion represented by formula (IId), an anion represented by formula (IIa), an anion represented by formula (IIb), and an anion represented by formula (IIc). Anions, anions represented by formula (IId), are more preferred, and anions represented by formula (IIa) are even more preferred.

（式中、Ｘ¹及びＸ²はそれぞれ独立に、フッ素原子又は炭素数１〜４のフッ化アルキル基を表すか、又はＸ¹とＸ²とが結合して炭素数２〜４のフッ化アルカンジイル基を形成する。）

(In the formula, X ¹ and X ² each independently represent a fluorine atom or an alkyl fluoride group having 1 to 4 carbon atoms, or X ¹ and X ² are bonded to form a fluorine having 2 to 4 carbon atoms. Forming an alkanediyl group.)

（式中、Ｘ³〜Ｘ⁵はそれぞれ独立に、フッ素原子又は炭素数１〜４のフッ化アルキル基を表す。）

(In the formula, X ^{3 to} X ⁵ independently represent a fluorine atom or an alkyl fluoride group having 1 to 4 carbon atoms.)

（式中、Ｙ¹は炭素数１〜４のフッ化アルキル基を表す。）

(In the formula, Y ¹ represents an alkyl fluoride group having 1 to 4 carbon atoms.)

（式中、Ｙ²は炭素数１〜４のフッ化アルカンジイル基を表す。）

(In the formula, Y ² represents an alkanediyl fluoride group having 1 to 4 carbon atoms.)

As the fluoroalkyl group having 1 to 4 carbon atoms represented by X ^{1 to} X ⁵ , respectively in the formulas (IIa) and (IIb), a perfluoroalkyl group is preferable, and for example, -CF ₃ , -CF ₂ CF ₃ , and so on. -CF ₂ CF ₂ CF ₃ , -CF (CF ₃ ) ₂ , -CF ₂ CF ₂ CF ₂ CF ₃ , -CF ₂ CF (CF ₃ ) ₂ , -C (CF ₃ ) _3, etc.

As the fluorinated alkanediyl group having 2 to 4 carbon atoms formed by bonding X ¹ and X ² in the formula (IIa), a perfluoroalkanediyl group is preferable, and for example, −CF ₂ CF ₂ −, −CF. ₂ CF ₂ CF ₂ −, − CF ₂ CF ₂ CF ₂ CF ₂ − and the like can be mentioned.

As the fluoroalkyl group having 1 to 4 carbon atoms represented by Y ¹ in the formula (IIc), a perfluoroalkyl group is preferable, and for example, −CF ₃ , −CF ₂ CF ₃ , −CF ₂ CF ₂ CF ₃ , -CF (CF ₃ ) ₂ , -CF ₂ CF ₂ CF ₂ CF ₃ , -CF ₂ CF (CF ₃ ) ₂ , -C (CF ₃ ) _{3, and the} like.

As the fluorinated alkanediyl group having 1 to 4 carbon atoms represented by Y ² in the formula (IId), a perfluoroalkanediyl group is preferable, and for example, −CF ₂ −, −CF ₂ CF ₂ −, −CF ₂ CF. ₂ CF ₂ −, −C (CF ₃ ) ₂ −, −CF ₂ CF ₂ CF ₂ CF ₂ − and the like can be mentioned.

Examples of the anion represented by the formula (IIa) (hereinafter sometimes referred to as “anion (IIa)”) include the following anions (IIa-1) to (IIa-6).

Examples of the anion represented by the formula (IIb) (hereinafter sometimes referred to as “anion (IIb)”) include the following anion (IIb-1).

Examples of the anion represented by the formula (IIc) (hereinafter sometimes referred to as “anion (IIc)”) include the following anions (IIc-1) to (IIc-4).

Examples of the anion represented by the formula (IId) (hereinafter sometimes referred to as "anion (IId)") include the following anions (IId-1) to (IId-4).

As the compound (Ia), a compound represented by the formula (Ib) (hereinafter, may be referred to as “compound (Ib)”) is preferable, and a compound represented by the formula (Ic) (hereinafter, “Compound (Ic)”). ”) Is more preferable.

(In the formula, R ² , R ⁵ , R ^{8 to} R ¹³ , X ^a- , a, and b are the same as described above. R ³⁰ is an alkyl group having 1 to 6 carbon atoms, a halogen atom, −OH, − _{^{OR 16, -S (O) 2}} O -, -S (O) 2 OH, -S (O) 2 O - Z +, -C (O) O -, -C (O) OH, -C (O ) O ^- Z ⁺ , -C (O) OR ¹⁶ , -C (O) NHR ¹⁶ , -C (O) NR ¹⁶ R ¹⁷ , -SR ¹⁶ , -S (O) ₂ R ¹⁶ , -S (O) ₂ OR ¹⁶ , -S (O) ₂ NH ₂ , -S (O) ₂ NHR ¹⁶ , or -S (O) ₂ NR ¹⁶ R ¹⁷ , and R ¹⁶ , R ¹⁷ , Z ⁺ are the same as above. m represents an integer from 0 to 5. When m is 2 or more, a plurality of R ^30s may be the same or different.)

(Wherein, R ²¹ and R ²² are, independently of one another, a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, C (O) O ^-, or -S (O) ₂ O ^- a representative .R ²³ and R ²⁴ represents an alkyl group having 1 to 4 carbon atoms independently of each other. R ^{25 to} R ²⁸ independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 10 carbon atoms, or 6 to 10 carbon atoms. It represents an aromatic hydrocarbon group, a saturated hydrocarbon group and the aromatic hydrocarbon group represented by the R ²⁵ to R ^{28 are, -C (O) O -,} -C (O) OH, -C (O) O - Z ^{+, -C (O) OR 16} , -C (O) NHR 16, -S (O) 2 O -, -S (O) 2 OH, -S (O) 2 O -
It may have at least one substituent selected from Z ⁺ and −S (O) ₂ NHR ¹⁶ . R ²⁵ and R ²⁶ , and R ²⁷ and R ²⁸ may be combined with each other to form a ring. R ³¹ represents an alkyl group having 1 to 6 carbon ^{atoms, -C (O) O -,} -C (O) OH, -C (O) O - Z +, -C (O) OR 16, -C (O ^{) NHR 16, -S (O)} 2 O - represents a Z ^+, or _{^{-S (O) 2 NHR 16 -}} , -S (O) 2 OH, -S (O) 2 O. ma represents an integer from 0 to 5. When ma is 2 or more, a plurality of R ^31s may be the same or different. X ^a- , a, b, R ¹⁶ , and Z ⁺ are the same as above. )
As R ²¹ and R ²² , hydrogen atom, methyl group, ethyl group, C (O) O ⁻ or −S (O) ₂ O ⁻ is preferable.
As R ²³ and R ²⁴ , a methyl group and an ethyl group are preferable, and R ²³ and R ²⁴ are preferably the same.
Examples of R ^{25 to} R ²⁸ include alkyl groups having 1 to 10 carbon atoms such as hydrogen atom, methyl group, ethyl group, n-propyl group, iso-propyl group and ethylhexyl group; phenyl group, toluyl group, xsilyl group, etc. group having a benzene ring structure, such as ethylphenyl group, and the benzene ring to ^{-C (O) O -, -C} (O) OH, -C (O) O - Z +, -C (O) oR 16, ^{-C (O) NHR 16, -S} (O) 2 O -, -S (O) 2 OH, -S (O) 2 O - Z +, or -S (O) and _a group ₂ NHR ¹⁶ is substituted Substituted or unsubstituted phenyl groups and the like are preferable. Examples of the ring formed by R ²⁵ and R ²⁶ and R ²⁷ and R ²⁸ include the following. In the formula, * represents a bond (single bond or double bond).

R ²⁵ and R ²⁶ are a combination in which both are saturated hydrocarbon groups having 1 to 10 carbon atoms which may independently have a substituent (hereinafter referred to as combination 4), and both have an independent substituent. A combination that becomes an aromatic hydrocarbon group having 6 to 10 carbon atoms (hereinafter referred to as combination 5), one is a saturated hydrocarbon group having 1 to 10 carbon atoms that may have a substituent, and the other is substituted. A combination of aromatic hydrocarbon groups having 6 to 10 carbon atoms which may have a group (hereinafter referred to as combination 6) is preferable, and combination 4 and combination 6 are more preferable. Also in R ²⁷ and R ²⁸ , combination 4, combination 5, combination 6, and the like are preferable, and combination 4 and combination 6 are more preferable. According to the combination 4, the heat resistance of the compound (Ia) becomes better, and according to the combination 6, the light resistance of the compound (Ia) becomes better.

ma is preferably 0 or 1.
The R ^31, a methyl group, an ethyl ^{group, -C (O) O -,} -C (O) OH, -C (O) O - Z +, -C (O) OR 16, -S (O) 2 _{^{O -, -S (O) 2}} OH, -S (O) 2 O - Z +, or -S (O) ₂ NHR ¹⁶ are preferred.

Examples of the compound (Ic) include compounds having the groups and anions shown in Tables 1 to 4 in the formula (Id). R ⁴³ and R ⁴⁴ , or R ⁴⁵ and R ⁴⁶ , together with the N to which they bind, represent any of the partial structures represented by (N1) to (N10). R ⁴⁷ represents any partial structure represented by (P1) to (P10). Xx ^- is, Cl ^- represents or (Xx1) any monovalent anion represented by ~ (XX11).

（式中、Ｒ¹〜Ｒ¹³、Ｘ、及びａは前記と同じ。Ｒ^8xは、Ｒ⁸又はＲ⁹から末端メチル基を除いた基と同じであり、Ｒ^8yは、Ｒ⁸又はＲ⁹と同じ。） The compound (Ia) is, for example, compounds represented by the formula (Vc) (hereinafter sometimes referred to as "Compound (Vc)"), a compound capable of generating an anion of R ⁷ (e.g., R ⁷ -MgBr reacting a Grignard reagent) such as, de-OH - ^(including the manner of leaving as water together with a proton) and, optionally X ^- compound capable of generating (e.g., X ^- adding a salt) containing Can be manufactured by. The compound (Vc) is, for example, a compound represented by the formula (Va) (hereinafter, may be referred to as “compound (Va)”) and a compound represented by the formula (Vb) (hereinafter, “compound (Vb)). It can be manufactured by reacting with). In addition, compound (Ia) can also be produced by appropriately referring to the method described in JP-A-2002-543233.

(In the formula, R ^{1 to} R ¹³ , X, and a are the same as above. R ^8x is the same as the group obtained by removing the terminal methyl group from R ⁸ or R ⁹ , and R ^8y is R ⁸ or R ^9. Same as.)

The content of the compound (Ia) is, for example, 1 to 100% by mass, preferably 50 to 100% by mass, based on the total amount of the colorant (A).

The colorant (A) may contain a dye or a pigment as a colorant other than the compound (Ia). Examples of dyes include solvent dyes, acidic dyes, direct dyes, and medium dyes. For example, compounds classified by the Color Index (published by The Society of Dyers and Colorists) as having a hue other than pigments and dyes. Known dyes described in the notebook (Color Dyeing Company) can be mentioned. As the pigment, 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 dyes that can be used include C.I. I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 162;
C. I. Solvent Red 45, 49, 125, 130;
C. I. Solvent Orange 2, 7, 11, 15, 26, 56;
C. I. Solvent Blue 4, 5, 37, 67, 70, 90;
C. I. Solvent Green 1, 4, 5, 7, 34, 35; etc. I. Solvent dye,
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. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 57, 66, 73, 88, 91, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 418, 422, 426;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;
C. I. Acid Violet 6B, 7, 17, 19;
C. I. Acid Blue 1,7,9,15,18,22,29,42,59,60,62,70,72,74,82,83,86,87,90,92,93,100,102,103, 104, 113, 117, 120, 126, 130, 131, 142, 147, 151, 154, 158, 161, 166, 167, 168, 170, 171, 184, 187, 192, 199, 210, 229, 234, 236, 242, 243, 256, 259, 267, 285, 296, 315, 335;
C. I. Acid Green 1, 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, 106, 109; etc. I. Acid dye,
C. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141;
C. I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241 and 243, 246, 250;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C. I. Direct Blue 1,2,6,8,15,22,25,41,57,71,76,78,80,81,84,85,86,90,93,94,95,97,98,99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;
C. I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82; etc. I. Direct dye,
C. I. Disperse Yellow 54, 76; etc. I. Disperse dye,
C. I. Basic Blue 1,3,5,7,9,19,24,25,26,28,29,40,41,54,58,59,64,65,66,67,68;
C. I. Basic Green 1; etc. I. Basic dye,
C. I. Reactive Yellow 2,76,116;
C. I. Reactive Orange 16; etc. I. Reactive dye,
C. I. Modant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modant Red 1,2,4,9,12,14,17,18,19,22,23,24,25,26,30,32,33,36,37,38,39,41,43,45 , 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95;
C. I. Modant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C. I. Modant Violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58;
C. I. Modant Blue 1,2,3,7,9,12,13,15,16,19,20,21,22,26,30,31,39,40,41,43,44,49,53,61 , 74, 77, 83, 84;
C. I. Modant Green 1, 3, 4, 5, 10, 15, 26, 29, 33, 34, 35, 41, 43, 53; etc. I. Mordant dye,
C. I. Bat Green 1; etc. I. Vat dyes, etc. can be mentioned.

Examples of pigments that can be used include
C. I. Pigment Yellow 1 (Hereinafter, the description of CI Pigment Yellow is omitted and only the number is described), 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83. , 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214 and the like;
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, 175, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, etc. Pigment;
C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60, 80 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet color pigments;
C. I. Pigment Green 7, 36, 58 and other green pigments; and the like.

(2) Resin (B)
The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and is at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter, "monomer (B)". A resin having a structural unit derived from (sometimes referred to as "a)") is more preferable. The resin (B) is further 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 “monomer (b)”). The structural unit, the monomer (c) copolymerizable with the monomer (a) (however, it is different from the monomer (a) and the monomer (b)) (hereinafter, “monomer (c)) It is preferable that the copolymer has at least one structural unit selected from the group consisting of a structural unit derived from (may be referred to as) and a structural unit having an ethylenically unsaturated bond in the side chain. A copolymer having a structural unit derived from the body (a) and a structural unit derived from the monomer (b) or a structural unit derived from the monomer (a) and a structure derived from the monomer (c). A copolymer having a unit is more preferable, and a structural unit derived from the monomer (a), a structural unit derived from the monomer (b), and a structural unit derived from the monomer (c) It is more preferable that the copolymer has

Specific examples of the monomer (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic acid anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and oxalic acid mono [2]. -(Meta) acryloyloxyethyl] and the like, preferably acrylic acid, methacrylic acid, maleic anhydride.

The monomer (b) is a single amount 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. The body is preferred.
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 the monomer (b) include glycidyl (meth) acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate, and 3-ethyl. -3- (Meta) acryloyloxymethyloxetane, tetrahydrofurfuryl (meth) acrylate and the like, preferably glycidyl (meth) acrylate, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] Decyl (meth) acrylate, 3-ethyl-3- (meth) acryloyloxymethyloxetane.

Examples of the monomer (c) include methyl (meth) acrylate, butyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, and tricyclo [5.2.1.0 ^2,6. ] (Meta) acrylic acid esters such as decane-8-yl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, etc. N-substituted maleimides; styrenes such as styrene and vinyltoluene; and the like. The monomer (c) is preferably at least one selected from the group consisting of styrenes and N-substituted maleimides.

A resin having a structural unit having an ethylenically unsaturated bond in the side chain has the monomer (b) added to the copolymer of the monomer (a) and the monomer (c), or the monomer. It can be produced by adding the monomer (a) to the copolymer of the monomer (b) and the monomer (c). The resin may be a resin obtained by adding the monomer (a) to a copolymer of the monomer (b) and the monomer (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 mg-KOH / g, and even more preferably 70 to 135 mg-KOH / g in terms of solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titrating with 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. The content of the compound (Ia) is preferably 0.1 to 40 parts by mass, and more preferably 0.5 to 30 parts by mass with respect to 1 part by mass. When the content of the resin (B) is within the above range, not only the developability at the time of forming the color filter is improved, but also the light resistance of the obtained color filter tends to be excellent.

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 or may not contain a polymerizable compound and / or a polymerization initiator. Hereinafter, the colored resin composition containing the polymerizable compound and the polymerization initiator may be referred to as a “colored curable resin composition”. Further, hereinafter, the polymerizable compound may be referred to as "polymerizable compound (C)", and the polymerization initiator may be referred to as "polymerization initiator (D)".

(3) 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.

(4) 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 and the like by the action of light and 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 Examples thereof include biimidazole.

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). It is a part, 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 initiator. Hereinafter, the polymerization initiator may be referred to as "polymerization initiator (D1)".
(5) Polymerization initiator (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).
As the polymerization initiator (D1), 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone, 9,10-dimethoxyanthracene, 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 initiator (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. Hereinafter, the solvent may be referred to as "solvent (E)".

(6) 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 include ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate and γ-butyrolactone (intramolecular). Solvents containing -COO- and not -O-; ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether ( Solvent containing -O- and not -COO- in the molecule); methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate , Ether ester solvent such as diethylene glycol monoethyl ether acetate (solvent containing -COO- and -O- in the molecule); 4-hydroxy-4-methyl-2-pentanone (also known as diacetone alcohol), heptanone, 4- Ketone solvent such as methyl-2-pentanone and cyclohexanone (solvent containing -CO- in the molecule and not containing -COO-); alcohol solvent such as butanol, cyclohexanol, propylene glycol (containing OH in the molecule and not-COO-) Solvents free of O-, -CO- and -COO-); amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone; and the like.

As the solvent, propylene glycol monomethyl ether acetate, diacetone alcohol, 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. ..

(7) Additives other than the above-mentioned components The colored resin composition of the present invention can be used as a leveling agent, a filler, other polymer compounds, an adhesion accelerator, an antioxidant, a light stabilizer, and chain transfer, if necessary. Additives known in the art may be included, such as agents.

(8) Method for Producing Colored Resin Composition The colored resin composition of the present invention comprises a colorant (A), a resin (B), a polymerizable compound (C) used as necessary, and a polymerization initiator (D). , Solvent (E) and other components can be mixed.

(9) Method for Producing Color Filter Examples of the method for producing a colored pattern from the colored resin composition of the present invention include a photolithography method, an inkjet method, a printing method and the like. Of these, the photolithography method is preferable.

According to the colored resin composition of the present invention, a color filter having high contrast can be produced. The color filter is useful as a color filter used in a liquid crystal display device, an organic EL device, a display device such as electronic paper, 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 to these Examples. In the examples,% and parts indicating the content or the amount used are based on mass unless otherwise specified.
In the following, the compounds obtained in the synthetic examples were identified by mass analysis (LC; Agilent 1200 type, MASS; Agilent LC / MSD type).

(Synthesis Example 1)
4.5 parts of 3-bromo-N, N-dimethylaniline (manufactured by Wako Pure Chemical Industries, Ltd.), 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( Aldrich) 4.9 parts, tetrakistriphenylphosphine palladium (0) (Tokyo Chemical Industry Co., Ltd.) 0.01 parts, and potassium carbonate (Kishida Chemical Co., Ltd.) 12.4 parts water 20 parts, It was dissolved in a mixed solution of 40 parts of ethanol (manufactured by Wako Pure Chemical Industries, Ltd.) and 100 parts of toluene (manufactured by Nacalai Tesque Co., Ltd.), and heated and stirred at 85 ° C. for 7 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and the organic layer was concentrated. After concentration, hexane was added and the resulting solid was removed by natural filtration, and the filtrate was concentrated again to obtain 3.1 parts of the compound represented by the formula (1-1). The yield was 86%.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] + 162.5
Exact Mass: +161.1

The compound represented by the formula (1-1) and 4- (dimethylamino) benzyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.) were used in "Angew. Chem. Int. Ed. 2016, 55, 3290-3294". The compound represented by the formula (1-2) was synthesized by the method represented.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] + 309.5
Exact Mass: 308.4

(Synthesis Example 2)
1.0 part of the compound represented by the formula (1-2) was dissolved in 60 parts of tetrahydrofuran (manufactured by Hayashi Junyaku Kogyo Co., Ltd.) under a nitrogen atmosphere, and the mixture was stirred in an ice bath. Subsequently, 8.9 parts of a 1 M tetrahydrofuran solution of phenylmagnesium bromide (manufactured by Kanto Chemical Co., Inc.) was slowly added, and the mixture was returned to room temperature and stirred for 2 hours. After completion of the reaction, a 5% aqueous ammonium chloride solution was added, and then chloroform was added to separate the liquids. After the liquid separation, the organic layer is concentrated and purified by a silica gel column (developing solvent: chloroform → methanol) to obtain 0.63 parts of the compound represented by the formula (1-3) (corresponding to compound number 1 in Table 1). It was. The yield was 47%.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] + 369.5
Exact Mass: +369.5

(Synthesis Example 3)
1.4 parts of the compound represented by the formula (1-3) and 1.2 parts of bis (trifluoromethanesulfonyl) imidelithium (manufactured by Tokyo Chemical Industry Co., Ltd.) are added to 20 parts of methanol (manufactured by Nacalai Tesque Co., Ltd.). It was dissolved and stirred at room temperature for 2 hours. After completion of the reaction, 200 parts of water was added, methanol was distilled off by an evaporator, and then suction filtration was performed. The obtained solid was dried under reduced pressure at 60 ° C. overnight to obtain 1.8 parts of a compound represented by the formula (1-4) (corresponding to compound number 2 in Table 1). The yield was 80%.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] + 369.5
Exact Mass: +369.5

(Synthesis Example 4)
Dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) 10 parts, bromoiodobenzene (manufactured by Tokyo Chemical Industry Co., Ltd.) 21 parts, palladium acetate 0.9 parts (manufactured by Tokyo Chemical Industry Co., Ltd.), t-butoxysodium 7 .9 parts (manufactured by Tokyo Chemical Industry Co., Ltd.), 4, 5'-bis (diphenylphosphino) -9,9'-dimethylxanthene 3.0 parts (manufactured by Tokyo Chemical Industry Co., Ltd.), 120 parts of toluene (manufactured by Tokyo Chemical Industry Co., Ltd.) (Made by Nakaraitesk Co., Ltd.) was added, and the mixture was heated and refluxed for 1 hour. Then, 100 parts of ethyl acetate (manufactured by Nacalai Tesque, Inc.) and 100 parts of water were added to separate the organic layer, and 100 parts of ethyl acetate was added to the aqueous layer to extract the organic layer, and then magnesium sulfate (Wako Pure Chemical Industries, Ltd.) was added. It was dried by Kogyo Co., Ltd. and separated, and the organic layer was concentrated. The obtained reaction mixture was purified by silica gel column chromatography to obtain 24 parts of the compound represented by the formula (2-1).

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] +276.0
Exact Mass: +275.0

(Synthesis Example 5)
15 minutes by adding 3.9 parts of sodium hydride (manufactured by Aldrich, oil dispersion content 60%) and 135 parts of dimethylformamide (manufactured by Nacalai Tesque, Inc.) to 27 parts of the compound represented by the formula (2-1). Stirring was performed. Then, 18.5 parts of ethyl iodide (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 40 ° C. for 30 minutes. After completion of the reaction, the organic layer was extracted with a mixed solution of hexane: ethyl acetate (4: 1), dried over magnesium sulfate and separated, and the organic layer was concentrated to obtain 25 parts of the compound represented by the formula (2-2). .. The yield was 83%.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] +304.0
Exact Mass: +303.0

(Synthesis Example 6)
To 100 parts of dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), 114 parts of potassium carbonate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 100 parts of dimethylformamide (manufactured by Nacalai Tesque Co., Ltd.) were added, and the mixture was stirred for 15 minutes. Then, 128 parts of ethyl iodide (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 40 ° C. for 30 minutes. After completion of the reaction, the organic layer was extracted with a mixed solution of hexane: ethyl acetate (4: 1), dried over magnesium sulfate, separated, and the organic layer was concentrated to add 115 parts of the compound represented by the formula (2-3). Obtained. The yield was 93%.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] + 150.1.
Exact Mass: +149.1

(Synthesis Example 7)
4-Bromobenzyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.) 10 parts, 3,4-dihydropyran (manufactured by Tokyo Chemical Industry Co., Ltd.) 4.6 parts, iodine (manufactured by Tokyo Chemical Industry Co., Ltd.) 0.2 50 parts of methylene chloride (manufactured by Nacalai Tesque, Inc.) were added, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, 100 parts of ethyl acetate and 100 parts of water were added to extract the organic layer, dried over magnesium sulfate and separated, and the obtained organic layer was concentrated to obtain the compound represented by the formula (2-4). I got 5.5 copies.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] + 271.1
Exact Mass: +270.0

(Synthesis Example 8)
5 parts of the compound represented by the formula (2-3), 9.4 parts of the compound represented by the formula (2-4), 0.75 part of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), t-butoxysodium (Manufactured by Tokyo Chemical Industry Co., Ltd.) 6.4 parts, t-butylphosphine 0.1M n-hexane solution (manufactured by Wako Pure Chemical Industries, Ltd.) 6.8 parts, toluene 30 parts (manufactured by Nacalai Tesque Co., Ltd.) ) Was added, and the mixture was heated and refluxed for 1 hour. Then, 50 parts of ethyl acetate and 50 parts of water were added to separate the organic layer, and 50 parts of ethyl acetate was added to the aqueous layer to extract the organic layer, which was then dried over magnesium sulfate, and the organic layer was concentrated. 7.0 parts of the compound represented by (2-5) was obtained. The yield was 61%.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] +340.2
Exact Mass: +339.2

(Synthesis Example 9)
13 parts of the compound represented by the formula (2-5), 130 parts of methanol (manufactured by Nacalai Tesque, Inc.) and 14 parts of a 10 wt% hydrochloric acid aqueous solution were added, and the mixture was heated under reflux for 30 minutes. After completion of the reaction, neutralize with 10 wt% aqueous sodium hydroxide solution to concentrate methanol, add 80 parts of ethyl acetate to extract the organic layer, dry with magnesium sulfate, separate, and concentrate the obtained organic layer to the formula (2). Eleven parts of the compound represented by -6) were obtained.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] + 256.1
Exact Mass: +255.2

(Synthesis Example 10)
17 parts of the compound represented by the formula (2-2), 13 parts of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (manufactured by Aldrich), tetrakistriphenylphosphine palladium (made by Aldrich). Tokyo Chemical Industry Co., Ltd. 3.4 parts, potassium carbonate 18 parts (Tokyo Chemical Industry Co., Ltd.), water 70 parts, ethanol (Nacalai Tesque Co., Ltd.) 150 parts, toluene (Nacalai Tesque Co., Ltd.) (Manufactured) 350 parts were added, and the mixture was heated under reflux for 2 hours. After completion of the reaction, ethyl acetate was added and the organic layer was extracted three times, and the obtained organic layer was washed with saturated brine. Then, it was dried over magnesium sulfate and separated, and the solvent was concentrated. The obtained reaction mixture was washed with hexane, filtered and dried to obtain 12.5 parts of the compound represented by the formula (2-7). The yield was 79.6%.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] +266.2
Exact Mass: +265.2

(Synthesis Example 11)
210 parts of dehydrated methylene chloride (manufactured by Nacalai Tesque, Inc.), 11 parts of the compound represented by the formula (2-6), and 12.5 parts of the compound represented by the formula (2-7) are mixed in an ice bath. , 1.3M Boron trichloride / methylene chloride solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise, and the mixture was stirred at room temperature for 12 hours after completion of the addition. After neutralization with an aqueous sodium hydroxide solution, extraction was performed with ethyl acetate, washed with saturated brine, dried over magnesium sulfate, and then separated to concentrate the solvent. The obtained reaction mixture was purified by silica gel column chromatography to obtain 7.5 parts of the compound represented by the formula (2-8). The yield was 57%.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] +503.3
Exact Mass: +502.3

(Synthesis Example 12)
1.8 parts of the compound represented by the formula (2-8) and 9 parts of polyphosphoric acid (manufactured by Nacalai Tesque, Inc.) were added, and the mixture was heated and stirred at 120 ° C. for 3 hours. After completion of the reaction, the mixture was neutralized with an aqueous sodium hydroxide solution, extracted with methylene chloride (manufactured by Nakaraitesk Co., Ltd.), washed with saturated brine, dried over magnesium sulfate, and the solvent was concentrated. The obtained reaction mixture was dissolved in 28 parts of acetone (manufactured by Nacalai Tesque Co., Ltd.) and cooled in an ice bath, and then 0.4 parts of potassium permanganate (manufactured by Tokyo Chemical Industry Co., Ltd.) was divided into several times. It was charged and stirred for 2 hours. Ethyl acetate was added and the solid was filtered to concentrate the solvent. The obtained reaction mixture was purified by silica gel column chromatography to obtain 0.2 parts of the compound represented by the formula (2-9). The yield was 32%.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] + 517.3
Exact Mass: +516.3

(Synthesis Example 13)
0.5 part of the compound represented by the formula (2-9) is dissolved in 10 parts of tetrahydrofuran (manufactured by Nacalai Tesque, Inc.), cooled to 0 ° C., and a 1.0 M phenylmagnesium bromide / tetrahydrofuran solution (Wako Pure Chemical Industries, Ltd.). 2.7 parts (manufactured by Yakuhin Kogyo Co., Ltd.) was added dropwise. After completion of the dropping, the temperature was raised to room temperature, the mixture was stirred for 2 hours, quenched with an aqueous ammonium chloride solution, the solvent was concentrated, and then extracted with chloroform three times. The obtained organic layer was washed with a saturated aqueous salt solution, dried over magnesium sulfate, separated, and the solvent was concentrated. The obtained reaction mixture was purified by silica gel chromatography to obtain 0.2 parts of the compound represented by the formula (2-10) (corresponding to compound number 11 in Table 1). The yield was 20%.

Identification: (Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] + 613.3
Exact Mass: +612.3

(Synthesis Example 14)
An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the nitrogen atmosphere, 371 parts of propylene glycol monomethyl ether acetate was placed therein, and the mixture was heated to 85 ° C. with stirring. Then, in the flask, 54 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8-ylacrylate and 3,4-epoxytricyclo [5.2. 1.0 ^2,6 ] 225 parts of decane-9-ylacrylate mixture (trade name "E-DCPA", manufactured by Daicel Co., Ltd.), 81 parts of vinyltoluene (isomer mixture), 80 parts of propylene glycol monomethyl ether acetate The mixed solution of was added dropwise over 4 hours. On the other hand, a solution prepared by dissolving 30 parts of the polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the dropping of the initiator solution is completed, the copolymer is kept at the same temperature for 4 hours, cooled to room temperature, and has a solid content of 37.5% and a viscosity of 246 mPa · s by a B-type viscometer (23 ° C.). (B-1)) A solution was obtained. The acid value of the resin (B-1) in terms of solid content was 115 mg-KOH / g, the weight average molecular weight Mw was 10600, and the dispersity [Mw / Mn] was 2.01. The resin (B-1) has the following structural units.

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
Equipment; HLC-8120GPC (manufactured by Tosoh Corporation)
Column; TSK-GELG2000HXL
Column temperature; 40 ° C
Solvent; THF
Flow velocity; 1.0 mL / min
Test solution solid content concentration; 0.001 to 0.01% by mass
Injection volume; 50 μL
Detector; RI
Calibration standard material; TSK STANDARD POLYSTYRENE
F-40, F-4, F-288, A-2500, A-500
(Made 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 1 to 3 and Comparative Example 1]
[Preparation of colored resin composition]
Each component was mixed in the number of copies shown in Table 5 to obtain a colored resin composition. The number of copies of the resin (B-1) indicates the value in terms of solid content.

<Preparation of colored coating film 1>
A colored resin composition was applied on a 5 cm square glass substrate (Eagle XG; manufactured by Corning Inc.) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to form a colored composition layer. After allowing to cool, the colored composition layer formed on the substrate was exposed to light at an exposure amount of 150 mJ / cm ² (365 nm standard) under an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). A colored coating was obtained by irradiation and then post-baking in an oven at 150 ° C. for 30 minutes.

<Film thickness measurement>
The film thickness of the obtained colored coating film was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.). The results are shown in Table 6.

<Heat resistance evaluation>
In the preparation of the colored coating film 1, the spectroscopy of the colored coating film before and after post-baking was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the CIE was used using the characteristic function of the C light source. The xy chromaticity coordinates (x, y) and the stimulus value Y in the XYZ colorimetric system are measured, and the color difference ΔEab * is obtained from the measured values by the method described in JIS Z 8730: 2009 (7. Color difference calculation method). Was calculated. If the heat resistance of the colored coating film is good, it can be said that the colored pattern produced from the same colored resin composition also has good heat resistance.

<Preparation of colored coating film 2>
A colored resin composition was applied on a 5 cm square glass substrate (Eagle XG; manufactured by Corning Inc.) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to form a colored composition layer. After allowing to cool, the colored composition layer formed on the substrate was exposed to light at an exposure amount of 150 mJ / cm ² (365 nm standard) under an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). By irradiating, a colored coating film was obtained.

<Measurement of maximum absorption value>
The maximum absorption wavelength λmax of the colored coating film obtained in Preparation 2 of the colored coating film was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation).
<Light resistance evaluation>
Ultraviolet ray cut filter (COLORED) on the colored coating film obtained in Preparation 2 of the colored coating film
OPTICAL GLASS L38; manufactured by Hoya Co., Ltd .; cuts light of 380 nm or less. ) Was placed, and xenon lamp light was irradiated for 48 hours with a light resistance tester (Suntest CPS +: manufactured by Toyo Seiki Co., Ltd.). The spectroscopic measurement of the colored coating film before and after irradiation was performed using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity in the CIE XYZ color system was measured using the characteristic function of the C light source. The coordinates (x, y) and the stimulus value Y were measured, and the color difference ΔEab * was calculated from the measured values by the method described in JIS Z 8730: 2009 (7. Color difference calculation method). The results are shown in Table 6. If the light resistance of the colored coating film is good, it can be said that the colored pattern produced from the same colored resin composition also has good light resistance.

According to the colored resin composition of the present invention, a color filter having excellent heat resistance and light resistance can be formed, and the color filter is useful for a display device and a solid-state image sensor.

Claims (4)

Contains colorants and resins
A colored resin composition in which the colorant contains a compound represented by the formula (Ia).

[In formula (Ia),
R ^{1 to} R ⁶ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, COO ⁻ , or S (O) ₂ O ⁻ , and R ² and R ³ and R ⁴ and R ⁵ may be bonded to each other to form an aromatic hydrocarbon ring which may have a substituent or an aromatic hetero ring which may have a substituent.
R ⁷ represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having ³ to 19 carbon atoms which may have a substituent, and R ³ Alternatively, it may be combined with R ⁴ to form a ring.
R ^8, R ⁹ are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms that may have a substituent group, COO ^-, or S (O) ₂ O ^- represents a R ⁸ R ⁹ may be bonded to each other to form a ring which may have a substituent.
R ^{10 to} R ¹³ independently have a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and 6 to 20 carbon atoms which may have a substituent. Represents an aromatic heterocyclic group having 3 to 19 carbon atoms which may have an aromatic hydrocarbon group or a substituent, and includes R ¹⁰ and R ¹¹ , R ¹² and R ¹³ , R ² and R ¹⁰ and R ⁵ . R ¹² may combine with each other to form a ring.
a represents 1 or 2.
b represents 0 or 1.
^Xa- represents an a-valent anion. ] The colored resin composition according to claim 1, further comprising a polymerizable compound and a polymerization initiator. A color filter formed from the colored resin composition according to claim 2. A display device including the color filter according to claim 3.