JP7680221B2 - colored resin composition - Google Patents

Description

The present invention relates to a colored resin composition.

Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored resin compositions. Various colorants are used as the colored resin compositions for forming the color filters, and for example, there is a known example in which a compound represented by the following formula (x) is used in a colored composition (Patent Document 1).

JP 2020-79396 A

However, when the above-mentioned perylene compounds are used as colored resin compositions, the heat resistance may not be fully satisfactory. Therefore, the present invention aims to provide a colored resin composition capable of forming a color filter having excellent heat resistance.

［式（Ｉ）中、
Ｒ¹～Ｒ¹¹は、互いに独立に、水素原子、－Ｒ^a1、－ＯＲ^a1、ハロゲン原子、ヒドロキシ基、カルボキシ基、－ＣＯ－Ｏ－Ｒ^a1、－Ｏ－ＣＯ－Ｒ^a1、－ＣＯ－Ｒ^a1又はニトロ基を表し、Ｒ⁷とＲ⁸とは互いに結合して環を形成してもよい。
Ｅは、Ｃ－Ｈ、Ｃ－Ｒ^a1又はＮを表す。
Ｒ^a1は、置換基を有していてもよい炭素数１～２０の炭化水素基を表す。］
［２］ さらに重合性化合物及び重合開始剤を含有する［１］に記載の着色樹脂組成物。
［３］ ［１］又は［２］に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］ ［３］に記載のカラーフィルタを含む表示装置。 The gist of the present invention is as follows.
[1] A colored resin composition comprising a colorant and a resin, wherein the colorant contains a compound represented by formula (I).

[In formula (I),
R ¹ to R ¹¹ each independently represent a hydrogen atom, -R ^a1 , -OR ^a1 , a halogen atom, a hydroxy group, a carboxy group, -CO-O-R ^a1 , -O-CO-R ^a1 , -CO-R ^a1 or a nitro group, and R ⁷ and R ⁸ may be bonded to each other to form a ring.
E represents CH, C—R ^a1 or N.
R ^a1 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.]
[2] The colored resin composition according to [1], further comprising a polymerizable compound and a polymerization initiator.
[3] A color filter formed from the colored resin composition according to [1] or [2].
[4] A display device comprising the color filter according to [3].

According to the present invention, it is possible to provide a colored resin composition capable of forming a color filter having excellent heat resistance.

The colored resin composition of the present invention contains a colorant (hereinafter, may be referred to as colorant (A)) and a resin (hereinafter, may be referred to as resin (B)), and the colorant contains a compound represented by formula (I).
The colored resin composition of the present invention may further contain a polymerizable compound (hereinafter, may be referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)).
The colored resin composition of the present invention may further contain a solvent (hereinafter, may be referred to as solvent (E)).
The colored resin composition of the present invention may further contain a polymerization initiation aid (hereinafter, may be referred to as polymerization initiation aid (D1)).
The colored resin composition of the present invention may further contain a leveling agent (hereinafter, may be referred to as leveling agent (F)).
In this specification, the compounds exemplified as each component may be used alone or in combination of two or more kinds, unless otherwise specified.

<Colorant (A)>
The colorant (A) contains a compound represented by formula (I) (hereinafter, may be referred to as compound (I)). A colored resin composition containing compound (I) as a colorant has excellent heat resistance and preferably also excellent light resistance.

［式（Ｉ）中、
Ｒ¹～Ｒ¹¹は、互いに独立に、水素原子、－Ｒ^a1、－ＯＲ^a1、ハロゲン原子、ヒドロキシ基、カルボキシ基、－ＣＯ－Ｏ－Ｒ^a1、－Ｏ－ＣＯ－Ｒ^a1、－ＣＯ－Ｒ^a1又はニトロ基を表し、Ｒ⁷とＲ⁸とは互いに結合して環を形成してもよい。
Ｅは、Ｃ－Ｈ、Ｃ－Ｒ^a1又はＮを表す。
Ｒ^a1は、置換基を有していてもよい炭素数１～２０の炭化水素基を表す。］ <<Compound (I)>>

[In formula (I),
R ¹ to R ¹¹ each independently represent a hydrogen atom, -R ^a1 , -OR ^a1 , a halogen atom, a hydroxy group, a carboxy group, -CO-O-R ^a1 , -O-CO-R ^a1 , -CO-R ^a1 or a nitro group, and R ⁷ and R ⁸ may be bonded to each other to form a ring.
E represents CH, C—R ^a1 or N.
R ^a1 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.]

The hydrocarbon group having 1 to 20 carbon atoms represented by R ^a1 includes an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ^a1 include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and icosyl groups; isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, (1-ethyl)pentyl, (3-ethyl)pentyl, (1-propyl)pentyl, and (1-butyl)pentyl groups. hexyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (1-pentyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (1-hexyl)heptyl group, (2-methyl)octyl group, (2-ethyl)octyl group, (1-heptyl)octyl group Examples of suitable alkyl groups include branched alkyl groups such as (2-ethyl)nonyl and (1-octyl)nonyl; and alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl)ethenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl))ethenyl, (1,2-dimethyl)propenyl and 2-pentenyl. The number of carbon atoms in the saturated chain hydrocarbon group is preferably 1 to 18, more preferably 2 to 15, and even more preferably 3 to 12. The number of carbon atoms in the unsaturated chain hydrocarbon group is preferably 2 to 18, more preferably 2 to 15, and even more preferably 3 to 12.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ^a1 include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group; cycloalkenyl groups such as cyclohexenyl group (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl group, and cyclooctenyl group; norbornyl group, adamantyl group, and bicyclo[2.2.2]octyl group. The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 15, and more preferably 3 to 12.

Examples of the aromatic hydrocarbon group represented by R ^a1 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, etc. The aromatic hydrocarbon group preferably has 6 to 15 carbon atoms, more preferably 6 to 12 carbon atoms.

The hydrocarbon group represented by R ^a1 may be a group in which two or more of the above-mentioned chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups are combined, as long as the upper limit of the carbon number is 20. Such a group may be, for example, a group in which an aromatic hydrocarbon group is combined with at least one group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group, and in such a hydrocarbon group in which the chain hydrocarbon group is combined as a divalent group (for example, an alkanediyl group). Examples of the hydrocarbon groups obtained by the above combinations include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylethenyl (phenylvinyl); arylalkynyl groups such as phenylethynyl; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5 -dimethylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, 2,3-diisopropylphenyl group, 2,4-diisopropylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisopropylphenyl group, 2,4,6-triisopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 2,6-di(tert-butyl)phenyl group, 3,5-di(tert-butyl)phenyl group alkylaryl groups such as 3,6-di(tert-butyl)phenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 4-pentylphenyl group, 4-octylphenyl group, 4-(2,4,4-trimethyl-2-pentyl)phenyl group, 2-dodecylphenyl group, 3-dodecylphenyl group, and 4-dodecylphenyl group; alkenylaryl groups such as 4-vinylphenyl group; 2,3-dihydro-4-indenyl group, 1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 8-methyl-1,2,3,5,6,7-hexahydro Examples of such aryl groups include aryl groups to which an alkanediyl group is bonded, such as a 4-s-indacenyl group, a 5,6,7,8-tetrahydro-1-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a 3-methyl-5,6,7,8-tetrahydro-2-naphthyl group, or a 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group; an aryl group to which one or more aryl groups are bonded, such as a biphenylyl group or a terphenylyl group; a cyclohexylmethylphenyl group, a benzylphenyl group, or a (dimethyl(phenyl)methyl)phenyl group. Furthermore, the above-mentioned hydrocarbon group may be, for example, a hydrocarbon group formed by a combination of a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof include a 1-methylcyclopropyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 1,4-dimethylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 2,4-dimethylcyclohexyl group, a 2,5-dimethylcyclohexyl group, a 2,6-dimethylcyclohexyl group, a 3,4-dimethylcyclohexyl group, a 3,5-dimethylcyclohexyl group, a 2,2-dimethylcyclohexyl group, a 3,3-dimethylcyclohexyl group, Examples of such alkyl groups include alicyclic hydrocarbon groups to which one or more alkyl groups or alicyclic hydrocarbon groups are bonded, such as 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, and 4-cyclohexylcyclohexyl group; and alkyl groups to which one or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group, and adamantylmethyl group. The number of carbon atoms in the group consisting of two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups is preferably 6 to 18, and more preferably 6 to 15.

Examples of the substituent that the hydrocarbon group having 1 to 20 carbon atoms represented by R ^a1 may have include a halogen atom, a nitrile group, a nitro group, an amino group, a hydroxy group, an alkoxy group having 1 to 20 carbon atoms, such as a methoxy group or an ethoxy group, an aryloxy group having 6 to 20 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group or a 2-naphthyloxy group, a thiol group, an alkylthio group having 1 to 20 carbon atoms, such as a methylthio group or an ethylthio group, an allylthio group, an arylthio group having 6 to 20 carbon atoms, such as a phenylthio group, a 1-naphthylthio group or a 2-naphthylthio group, a sulfoxy group, an alkylsulfoxy group having 1 to 20 carbon atoms, such as a methylsulfoxy group or an ethylsulfoxy group, an arylsulfoxy group having 6 to 20 carbon atoms, such as a phenylsulfoxy group, a 1-naphthylsulfoxy group or a 2-naphthylsulfoxy group, a silyl group, a boryl group, a monomethylamino group, a dimethyl ... arylamino groups having 6 to 20 carbon atoms, such as a monophenylamino group, a diphenylamino group, and a triphenylamino group; aralkylamino groups having 7 to 20 carbon atoms, such as a benzylamino group; a carboxy group; a carbamoyl group; alkylcarbonyl groups having 2 to 20 carbon atoms, such as an acetyl group and a propionyl group; arylcarbonyl groups having 7 to 20 carbon atoms, such as a benzoyl group, a 1-naphthylcarbonyl group, and a 2-naphthylcarbonyl group; alkoxycarbonyl groups having 2 to 20 carbon atoms, such as a methoxycarbonyl group and an ethoxycarbonyl group; and aryloxycarbonyl groups having 7 to 20 carbon atoms, such as a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group, and a 2-naphthyloxycarbonyl group.

The halogen atom may be a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or the like. From the viewpoint of synthesis, a chlorine atom and a bromine atom are preferred.

Examples of R ^a1 include groups represented by the following formulae (D-1) to (D-47) and (G-1) to (G-22), in which * represents a bond.

Examples of -OR ^a1 represented by R ¹ to R ¹¹ include oxy groups having the above-mentioned R ^a1 , such as alkoxy groups having 1 to 20 carbon atoms and aryloxy groups having 6 to 20 carbon atoms. Specific examples of -OR ^a1 include methoxy groups, ethoxy groups, propoxy groups, butoxy groups, pentyloxy groups, phenoxy groups, and naphthyloxy groups.

Examples of the halogen atom represented by R ¹ to R ¹¹ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, etc. From the viewpoint of synthesis, a chlorine atom and a bromine atom are preferred.

Examples of --CO--O--R ^a1 represented by R ¹ to R ¹¹ include oxycarbonyl groups having the above-mentioned R ^a1 , such as alkoxycarbonyl groups having 2 to 21 carbon atoms and aryloxycarbonyl groups having 7 to 21 carbon atoms. R ^a1 in -CO-O-R ^a1 is preferably a saturated chain hydrocarbon group, a saturated alicyclic hydrocarbon group, a group combining an alicyclic hydrocarbon group with a chain hydrocarbon group, an aromatic hydrocarbon group, or a group combining an aromatic hydrocarbon group with a chain hydrocarbon group, more preferably a saturated chain hydrocarbon group having 1 to 20 carbon atoms, a saturated alicyclic hydrocarbon group having 3 to 15 carbon atoms, a group combining an alicyclic hydrocarbon group having 4 to 15 carbon atoms with a chain hydrocarbon group, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group combining an aromatic hydrocarbon group having 7 to 20 carbon atoms with a chain hydrocarbon group, and even more preferably a saturated chain hydrocarbon group having 3 to 18 carbon atoms, a group combining an alicyclic hydrocarbon group having 4 to 10 carbon atoms with a chain hydrocarbon group, or a group combining an aromatic hydrocarbon group having 7 to 15 carbon atoms with a chain hydrocarbon group. -CO-O-R Specific examples of ^a1 include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a sec-butoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a (1-ethyl)pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, a (1-butyl)heptyloxycarbonyl group, an octyloxycarbonyl group, a (1-heptyl)octyloxycarbonyl group, a nonyloxycarbonyl group, and the like. Examples of such groups include a phenyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a tridecyloxycarbonyl group, a tetradecyloxycarbonyl group, a pentadecyloxycarbonyl group, a hexadecyloxycarbonyl group, a heptadecyloxycarbonyl group, an octadecyloxycarbonyl group, a phenyloxycarbonyl group, a benzyloxycarbonyl group, a cyclohexyloxycarbonyl group, a cyclohexylmethoxycarbonyl group, and an icosyloxycarbonyl group.

Examples of -O-CO-R ^a1 represented by R ¹ to R ¹¹ include carbonyloxy groups having the above-mentioned R ^a1 , such as alkylcarbonyloxy groups having 2 to 21 carbon atoms and arylcarbonyloxy groups having 7 to 21 carbon atoms. Specific examples of -O-CO-R ^a1 include methylcarbonyloxy groups, ethylcarbonyloxy groups, propylcarbonyloxy groups, butylcarbonyloxy groups, pentylcarbonyloxy groups, hexylcarbonyloxy groups, (2-ethyl)hexylcarbonyloxy groups, phenylcarbonyloxy groups, and cyclohexylcarbonyloxy groups.

Examples of -CO-R ^a1 represented by R ¹ to R ¹¹ include carbonyl groups having the above-mentioned R ^a1 , such as alkylcarbonyl groups having 2 to 21 carbon atoms and arylcarbonyl groups having 7 to 21 carbon atoms. Specific examples of -CO-R ^a1 include an acetyl group, a propionyl group, a butyroyl group, a pentanoyl group, a hexanoyl group, a cyclohexanoyl group, and a benzoyl group.

Examples of the ring formed by combining R ⁷ and R ⁸ together include groups represented by the following formulae (H-1) to (H-4).

［式（Ｈ－１）～式（Ｈ－４）中、
Ｒ¹²～Ｒ²⁴は、互いに独立に、水素原子、－Ｒ^a2、－ＯＲ^a2、ハロゲン原子、ヒドロキシ基、カルボキシ基、－ＣＯ－Ｏ－Ｒ^a2、－Ｏ－ＣＯ－Ｒ^a2、－ＣＯ－Ｒ^a2又はニトロ基を表し、Ｒ^a2は、置換基を有していてもよい炭素数１～２０の炭化水素基を表す。
＊はＲ⁷が有する結合手を表し、＊＊はＲ⁸が有する結合手を表す。］

[In formulas (H-1) to (H-4),
R ¹² to R ²⁴ each independently represent a hydrogen atom, -R ^a2 , -OR ^a2 , a halogen atom, a hydroxy group, a carboxy group, -CO-O-R ^a2 , -O-CO-R ^a2 , -CO-R ^a2 or a nitro group, and R ^a2 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
* represents a bond possessed by R ⁷ , and ** represents a bond possessed by R ⁸ .

Examples of the hydrocarbon group having 1 to 20 carbon atoms and which may have a substituent, represented by R ^a2 , include the same groups as those described as the hydrocarbon group having 1 to 20 carbon atoms and which may have a substituent, represented by R ^a1 , and preferred embodiments thereof are also the same.

Examples of the halogen atom represented by R ¹² to R ²⁴ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of synthesis, a chlorine atom and a bromine atom are preferred.

Examples of -OR ^a2 , -CO-O-R ^a2 , -O-CO-R ^a2 , and -CO-R ^a2 as R ¹² to R ²⁴ include the groups explained as -OR ^a1 , -CO-O-R ^a1 , -O-CO-R ^a1 , and -CO-R ^a1 in the table for R ¹ to R ¹¹ .

In E, C--H means a carbon atom bonded to a hydrogen atom, C--R ^a1 means a carbon atom bonded to R ^a1 , and N means a nitrogen atom.

R ¹ and R ² are preferably each independently a saturated chain hydrocarbon group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, or a group in which an aromatic hydrocarbon group which may have a substituent and a chain hydrocarbon group are combined. From the viewpoint of improving the solubility of compound (I) in a solvent, the saturated chain hydrocarbon group is preferably a saturated branched chain hydrocarbon group. The number of carbon atoms in the saturated chain hydrocarbon group (preferably a saturated branched chain hydrocarbon group) is preferably 1 to 15, more preferably 3 to 15. The aromatic hydrocarbon group is preferably a phenyl group. The group in which an aromatic hydrocarbon group and a chain hydrocarbon group are combined is preferably a phenyl group to which a chain hydrocarbon group having 1 to 12 carbon atoms (preferably 1 to 10) is bonded, more preferably a phenyl group to which 2 to 3 chain hydrocarbon groups having 1 to 4 carbon atoms are bonded, and even more preferably a phenyl group to which chain hydrocarbon groups having 1 to 4 carbon atoms are bonded to two ortho positions. Among them, R ¹ and R ² are each independently a group represented by the above formula (D-4) to formula (D-14), or formula (G-5) to formula (G-22). It is more preferable that each is independently a group represented by any one of formulas (D-4) to (D-14), (G-5), (G-7), (G-8), (G-11) to (G-13), (G-15), (G-16), (G-19), (G-21), or (G-22). It is particularly preferable that each is independently a group represented by any one of formulas (D-4) to (D-14), (G-7), (G-11), (G-13), (G-15), or (G-16).
It is also preferable that R ¹ and R ² are the same group.

R ³ to R ⁶ are each preferably, independently, a hydrogen atom, a halogen atom, or a hydroxyl group, and more preferably a hydrogen atom.

It is preferable that ^R7 and ^R8 are each independently a hydrogen atom, a halogen atom, or a hydroxyl group, or are bonded to each other to form a ring.
It is more preferable that R ⁷ and R ⁸ are hydrogen atoms, or R ⁷ and R ⁸ are bonded to each other to form any one of the groups represented by the above formulas (H-1) to (H-3),
It is more preferable that R ⁷ and R ⁸ are hydrogen atoms, or that R ⁷ and R ⁸ are bonded to each other to form the above formula (H-1) or formula (H-2).

R ¹² to R ²⁴ are each preferably, independently, a hydrogen atom, --R ^a2 , a halogen atom or a hydroxyl group, and more preferably a hydrogen atom.

R ⁹ to R ¹¹ are each preferably, independently, a hydrogen atom, --R ^a1 , a halogen atom or a hydroxyl group, and more preferably a hydrogen atom.

E is preferably C-H or N.

Specific examples of compound (I) include compounds (I-1) to (I-30) shown in Table 1 below.

In Table 1, H represents a hydrogen atom, and N represents a nitrogen atom.
D-6, D-13, and G-7 respectively represent groups represented by the above formulae (D-6), (D-13), and (G-7).
C--H means a carbon atom having a hydrogen atom attached thereto.
H-1-1, H-2-1, H-3-1, and H-4-1 represent embodiments in which R ⁷ and R ⁸ are bonded to each other to form groups represented by the following formulae (H-1-1), (H-2-1), (H-3-1), and (H-4-1), respectively. In the following formulae, * represents a bond possessed by R ⁷ , and ** represents a bond possessed by R ⁸ .

Compound (I) is preferably compound (I-17) to (I-24), and more preferably compound (I-17) to (I-22).

Compound (I) can be prepared, for example, according to Route 1 or Route 2.
Route 1 comprises step (i) of reacting a compound represented by the following formula (pt-1) with _X2 to obtain a compound represented by formula (pt-2), and step (ii) of reacting a compound represented by formula (pt-2) with a compound represented by formula (MA-1) to obtain compound (I).
Route 2 comprises a step (iii) of reacting a compound represented by the following formula (pt-2) with a compound represented by formula (MA-2) to obtain a compound represented by formula (pt-3), and a step (iv) of converting the compound represented by formula (pt-3) to obtain compound (I).

In the above formulas (pt-1) to (pt-3), R ¹ to R ¹¹ and E have the same meanings as defined above. In formulas (MA-1) and (MA-2), R ^B1 each independently represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a 2,2-dimethylpropyl-1,3-diyl group formed by two R ^B1s to form a ring, a 2,3-dimethylbutyl-2,3-diyl group, a 2-methylpentyl-2,4-diyl group, a 1,2-phenylene group, or the like.

X in _X2 used in step (i) of Route 1 represents a halogen atom, and is preferably a chlorine atom or a bromine atom. The compound represented by formula (pt-2) can be produced by reacting the compound represented by formula (pt-1) with _X2 in a solvent.

Examples of compounds represented by formula (pt-1) include N,N'-bis(2,6-diisopropylphenyl)-3,4,9,10-perylenetetracarboxylic acid diimide.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid, with methylene chloride and chloroform being more preferred.

The amount of _X2 used is usually 1 mole or more and 5 moles or less, more preferably 1 mole or more and 2.5 moles or less, and even more preferably 1 mole or more and 1.25 moles or less, relative to 1 mole of the compound represented by formula (pt-1).

The amount of the solvent used is usually 1 to 1,000 parts by mass per part by mass of the compound represented by formula (pt-1).

The reaction temperature is usually between -100°C and 300°C.

In step (ii), compound (I) can be produced by reacting a compound represented by formula (pt-2) (sometimes referred to as compound (pt-2)) with a compound represented by formula (MA-1) in a solvent in the presence of a catalyst, a phosphine ligand, and a base.

The catalyst includes tris(dibenzylideneacetone)dipalladium(0), bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, palladium(II) chloride, sodium tetrachloropalladate(II), palladium(II)(π-cinnamyl)chloride (dimer), allylpalladium(II) chloride dimer, bis(benzonitrile)palladium(II) dichloride, and bis(acetonitrile)palladium(II) dichloride, with palladium(II) acetate and bis(dibenzylideneacetone)palladium(0) being more preferred.

The phosphine ligands include tributylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, triphenylphosphine, tri(o-tolyl)phosphine, tri(m-tolyl)phosphine, tri(p-tolyl)phosphine, tris(3-methoxyphenyl)phosphine, tris[3,5-bis(trifluoromethyl)phenyl]phosphine, ethyldiphenylphosphine, tris(2,6-dimethoxyphenyl)phosphine, tris(4-fluorophenyl), diphenylpropylphosphine, di-tert-butylphenylphosphine, tri(2-furyl)phosphine, tri(2-thienyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, methyldiphenylphosphine, 1-[2-(di-tert-butylphosphino)phenyl]-3,5-diphenyl -1H-pyrazole, (4-dimethylaminophenyl)di-tert-butylphosphine, 2-(di-tert-butylphosphino)biphenyl, di-tert-butyl(1,1-diphenyl-1-propen-2-yl)phosphine, isopropyldiphenylphosphine, 2-(dicyclohexylphosphino)-2'-(dimethylamino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, 2-(diphenylphosphine sphino)biphenyl, 2-dicyclohexylphosphino-2'-methylbiphenyl, 2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, dicyclohexyl(1-methyl-2,2-diphenylcyclopropyl)phosphine, di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'- biphenyl]-2-yl)phosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-diphenylphosphino-2'-(N,N-dimethylamino)biphenyl, 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl, dicyclohexyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine monodentate phosphine ligands such as dicyclohexyl(1,1-diphenyl-1-propen-2-yl)phosphine, bis(diphenylphosphino)methane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 4,5-bis(dicyclohexylphosphino )-9,9-dimethylxanthene, 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene, 1',2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-biphenyl, 4,5-bis(diphenylphosphino)-9,9-dimethylxane, 1,3-bis(diphenylphosphino)propane, 1,1'-bis(di-tert-butylphosphino)ferrocene, bis[2-(diphenylphosphino)phenyl]ether, 1,1'-bis(diisopropylphosphino)ferrocene, 1,1'-bis(diphenylphosphino)ferrocene and other bidentate phosphine ligands are included, preferably monodentate phosphine ligands, more preferably triphenylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, and most preferably triphenylphosphine.

The base includes inorganic bases and organic bases.
Examples of inorganic bases include hydroxides, carbonates, hydrogencarbonates, phosphates, carboxylates, alkoxides, etc. of alkali metals or alkaline earth metals. The base used here may be in the form of anhydrous or hydrated substance.
The inorganic base is preferably a hydroxide, carbonate, hydrogen carbonate, phosphate, or carboxylate of an alkali metal or alkaline earth metal, more preferably a carbonate or phosphate of an alkali metal or alkaline earth metal. The salt of an alkali metal or alkaline earth metal is preferably a carbonate such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, or barium carbonate, or a phosphate such as lithium phosphate, sodium phosphate, or potassium phosphate, more preferably sodium carbonate, potassium carbonate, or potassium phosphate.
Examples of the organic base include triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, N,N-diisopropylethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]-5-nonene, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like, and 1,8-diazabicyclo[5.4.0]-7-undecene is more preferable.
As the base, hydroxides, carbonates, hydrogencarbonates, phosphates, and carboxylates of alkali metals or alkaline earth metals, and organic bases are preferred, and carbonates and phosphates of alkali metals or alkaline earth metals, and organic bases are more preferred.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid. N,N-dimethylformamide, N,N-dimethylacetamide, and toluene are preferred.

The amount of the catalyst used is usually 0.01 mol or more and 1 mol or less, more preferably 0.01 mol or more and 0.5 mol or less, and even more preferably 0.01 mol or more and 0.25 mol or less, relative to 1 mol of compound (pt-2).
The amount of the phosphine ligand used is usually 0.01 mol or more and 3 mol or less, more preferably 0.02 mol or more and 1 mol or less, and even more preferably 0.02 mol or more and 0.5 mol or less, relative to 1 mol of compound (pt-2).
The amount of the base used is usually 1 mole or more and 50 moles or less, more preferably 1 mole or more and 25 moles or less, and even more preferably 1 mole or more and 15 moles or less, relative to 1 mole of compound (pt-2).

The amount of the compound represented by formula (MA-1) used is usually 1 mole or more and 10 moles or less, more preferably 1 mole or more and 5 moles or less, and even more preferably 1 mole or more and 2 moles or less, per mole of compound (pt-2).

The amount of solvent used is usually 1 to 1,000 parts by mass per part by mass of compound (pt-2).

The reaction temperature is usually between -100°C and 300°C.

The compound represented by formula (pt-3) in step (iii) of route 2 (sometimes referred to as compound (pt-3)) can be produced by reacting compound (pt-2) with compound represented by formula (MA-2) in a solvent in the presence of a catalyst, a phosphine ligand, and a base. Compound (pt-2) can be produced, for example, by the above-mentioned step (i).

The catalyst includes tris(dibenzylideneacetone)dipalladium(0), bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, palladium(II) chloride, sodium tetrachloropalladate(II), palladium(II)(π-cinnamyl)chloride (dimer), allylpalladium(II) chloride dimer, bis(benzonitrile)palladium(II) dichloride, and bis(acetonitrile)palladium(II) dichloride, with palladium(II) acetate and bis(dibenzylideneacetone)palladium(0) being more preferred.

The phosphine ligands include tributylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, triphenylphosphine, tri(o-tolyl)phosphine, tri(m-tolyl)phosphine, tri(p-tolyl)phosphine, tris(3-methoxyphenyl)phosphine, tris[3,5-bis(trifluoromethyl)phenyl]phosphine, ethyldiphenylphosphine, tris(2,6-dimethoxyphenyl)phosphine, tris(4-fluorophenyl), diphenylpropylphosphine, di-tert-butylphenylphosphine, tri(2-furyl)phosphine, tri(2-thienyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, methyldiphenylphosphine, 1-[2-(di-tert-butylphosphine diphenylphosphine, (4-dimethylaminophenyl)di-tert-butylphosphine, 2-(di-tert-butylphosphino)biphenyl, di-tert-butyl(1,1-diphenyl-1-propen-2-yl)phosphine, isopropyldiphenylphosphine, 2-(dicyclohexylphosphino)-2'-(dimethylamino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, 2-(diphenylphosphino)biphenyl, 2-dicyclohexylphosphino-2'-methylbiphenyl, 2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, dicyclohexyl(1-methyl-2,2-diphenylcyclopropyl)phosphine, di-tert- Monodentate phosphine ligands such as butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-diphenylphosphino-2'-(N,N-dimethylamino)biphenyl, 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl, dicyclohexyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine, dicyclohexyl(1,1-diphenyl-1-propen-2-yl)phosphine, bis(diphenylphosphino)methane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino) 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 4,5-bis(dicyclohexylphosphino)-9,9-dimethylxanthene, 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene, 1',2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-biphenyl, 4,5-bis(diphenylphosphino)-9, Examples of bidentate phosphine ligands include 9-dimethylxane, 1,3-bis(diphenylphosphino)propane, 1,1'-bis(di-tert-butylphosphino)ferrocene, bis[2-(diphenylphosphino)phenyl]ether, 1,1'-bis(diisopropylphosphino)ferrocene, and 1,1'-bis(diphenylphosphino)ferrocene, and preferably, monodentate phosphine ligands.

The base includes inorganic bases such as hydroxides, carbonates, hydrogen carbonates, phosphates, carboxylates, and alkoxides of alkali metals or alkaline earth metals. The base used here may be in the form of anhydrous or hydrated substances. Preferred are hydroxides, carbonates, hydrogen carbonates, phosphates, and carboxylates of alkali metals or alkaline earth metals, and more preferred are carbonates and phosphates of alkali metals or alkaline earth metals. Preferred alkali metal or alkaline earth metal salts are lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, barium carbonate, lithium phosphate, sodium phosphate, and potassium phosphate, and more preferred are sodium carbonate, potassium carbonate, and potassium phosphate.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid. Toluene, xylene, and tetrahydrofuran are preferred.

The amount of the catalyst used is usually 0.01 mol or more and 1 mol or less, more preferably 0.01 mol or more and 0.5 mol or less, and even more preferably 0.01 mol or more and 0.25 mol or less, relative to 1 mol of compound (pt-2).
The amount of the phosphine ligand used is usually 0.01 mol or more and 3 mol or less, more preferably 0.02 mol or more and 1 mol or less, and even more preferably 0.02 mol or more and 0.5 mol or less, relative to 1 mol of compound (pt-2).
The amount of the base used is usually 1 mole or more and 50 moles or less, more preferably 1 mole or more and 25 moles or less, and even more preferably 1 mole or more and 15 moles or less, relative to 1 mole of compound (pt-2).

The amount of the compound represented by formula (MA-2) used is usually 1 mole or more and 10 moles or less, more preferably 1 mole or more and 5 moles or less, and even more preferably 1 mole or more and 2 moles or less, per mole of compound (pt-2).

The amount of solvent used is usually 1 to 1,000 parts by mass per part by mass of compound (pt-2).

The reaction temperature is usually between -100°C and 300°C.

In step (iv) of route 2, compound (I) can be produced by reacting a compound represented by formula (pt-3) (sometimes referred to as compound (pt-3)) in a solvent by irradiating it with light.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid, with dichloromethane and chloroform being preferred.

The light source used for light irradiation is not limited, and examples include sunlight, a xenon lamp, a fluorescent lamp, a light-emitting diode (LED), a low-pressure mercury lamp, a high-pressure mercury lamp, a metal hydride lamp, etc.

The amount of solvent used is usually 1 to 1,000 parts by mass per part by mass of compound (pt-3).

The reaction temperature is usually between -100°C and 300°C.

Also, compound (I) in step (iv) can be produced by reacting compound (pt-3) with compound (MA-3) in a solvent.

Examples of compound (MA-3) include metal chlorides, with iron(III) chloride, zinc chloride, and aluminum chloride being preferred.

The amount of compound (MA-3) used is usually 0.01 mol or more and 10 mol or less, more preferably 0.1 mol or more and 5 mol or less, per 1 mol of compound (pt-3).

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and nitro solvents such as nitromethane and nitrobenzene. Dichloromethane, chloroform, and nitromethane are preferred.

The amount of solvent used is usually 1 to 1,000 parts by mass per part by mass of compound (pt-3).

The reaction temperature is usually between -100°C and 300°C.

<<Colorant (A1)>>
The colored resin composition of the present invention may contain, as the colorant (A), a dye other than the compound (I) (hereinafter, sometimes referred to as dye (A1-1)) and/or a pigment (hereinafter, sometimes referred to as pigment (A1-2)). Hereinafter, the dye (A1-1) and the pigment (A1-2) may be collectively referred to as colorant (A1). These may be used alone or in combination of two or more kinds.

As long as the dye (A1-1) does not contain compound (I), it is not particularly limited and known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used according to their chemical structure include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Of these, organic solvent-soluble dyes are preferred.

Specific examples of the dye (A1-1) include:
C.I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;
C.I. Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;
C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C.I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C.I. Solvent dyes such as C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35;
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, 1 57, 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, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 18 2, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 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, 149, 162, 169, 173;
C.I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;
C.I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90: 1, 91, 92, 93, 93: 1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;
C. I. Acid dyes such as C. I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109;
C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C.I. 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, 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, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 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 dyes such as C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82;
C.I. Disperse Yellow 51, 54, 76;
C.I. Disperse Violet 26, 27;
C.I. Disperse dyes such as C.I. Disperse Blue 1, 14, 56, 6;0,
C.I. Basic Red 1, 10;
C.I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;
C.I. Basic Violet 2;
C.I. Basic Red 9;
C.I. Basic dyes such as C.I. Basic Green 1;
C.I. Reactive Yellow 2, 76, 116;
C.I. Reactive Orange 16;
C.I. Reactive dyes such as C.I. Reactive Red 36;
C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C.I. Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;
C.I. Mordant 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. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;
C.I. Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84;
C.I. Mordant dyes such as C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53;
and the like.

The pigment (A1-2) is not particularly limited, and any known pigment can be used as long as it does not contain compound (I). Examples of the pigment include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).
Examples of pigments classified as C.I. Pigment include yellow pigments such as C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231;
Orange pigments such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
red pigments such as C.I. Pigment Red 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273;
blue pigments such as C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60;
Violet pigments such as C.I. Pigment Violet 1, 19, 23, 32, 36, 38;
green pigments such as C.I. Pigment Green 7, 36, 58, 59, 62, 63;
Brown pigments such as C.I. Pigment Brown 23 and 25;
C.I. Pigment Black 1, 7 and other black pigments.

As the colorant (A1), yellow, red or green dyes and pigments are preferred.

The colorant (A1) may be subjected to, as necessary, a rosin treatment, a surface treatment using a derivative having an acidic or basic group introduced therein, a grafting treatment to the surface of the colorant (A1) using a polymer compound, a micronization treatment using a sulfuric acid micronization method, a washing treatment using an organic solvent or water to remove impurities, a removal treatment of ionic impurities using an ion exchange method, etc. It is preferable that the particle size of the colorant (A1) is approximately uniform.

When colorant (A) further contains colorant (A1), the content of compound (I) is, for example, 1 mass% or more, preferably 2 mass% or more, more preferably 10 mass% or more, even more preferably 25 mass% or more, and particularly preferably 50 mass% or more, based on the total amount of colorant (A). When colorant (A) further contains colorant (A1), the content of compound (I) is, for example, less than 100 mass% based on the total amount of colorant (A).

When the colored resin composition contains a solvent (E), a colorant-containing liquid (sometimes called a colored composition) containing the colorant (A) and the solvent (E) may be prepared in advance, and then the colored resin composition may be prepared using the colorant-containing liquid. When the colorant (A) is not soluble in the solvent (E), for example, when the colorant (A) contains a pigment (A1-2), the colorant-containing liquid can be prepared by dispersing the colorant (A) in the solvent (E) and mixing. The colorant-containing liquid may contain a part or all of the solvent (E) contained in the colored resin composition.

The solid content in the colorant-containing liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, even more preferably 0.1% by mass or more and 99% by mass or less, still more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1% by mass or more and 50% by mass or less, based on the total amount of the colorant-containing liquid.

The colorant (A) may be dispersed uniformly in the solution by adding a dispersant. When two or more types of colorant (A) are used in combination, each may be dispersed alone, or multiple types may be mixed and dispersed.

Examples of dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more. Examples of dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLORENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.). Resin (B), which will be described later, may be used as the dispersant.

When a dispersant is used, the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10,000 parts by mass or less, preferably 5 parts by mass or more and 5,000 parts by mass or less, more preferably 10 parts by mass or more and 1,000 parts by mass or less, and even more preferably 15 parts by mass or more and 800 parts by mass or less, per 100 parts by mass of colorant (A). When the amount of the dispersant used is within the above range, a colorant-containing liquid in a more uniformly dispersed state tends to be obtained.

The content of the colorant (A) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass or less, and even more preferably 1% by mass or more and 30% by mass or less, based on the total amount of solids in the colored resin composition. When the content of the colorant (A) is within the above range, the color density when made into a color filter is sufficient, and the necessary amount of the resin (B) can be contained in the composition, so that a pattern with sufficient mechanical strength can be formed, which is preferable.
Here, the "total amount of solids" in this specification refers to the 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 thereto can be measured by a known analytical means such as liquid chromatography or gas chromatography.

<Resin (B)>
Resin (B) is not particularly limited, but is preferably a resin used for forming a photoresist, different from a thermoplastic resin. Among them, resin (B) is more preferably an alkali-soluble resin, and more preferably an alkali-soluble resin having a carboxylic acid. The colored resin composition using an alkali-soluble resin as resin (B) can be suitably used for photoresist applications.

Examples of the resin (B) include the following resins [K1] to [K6].
Resin [K1]: a copolymer having a structural unit derived from at least one member (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond;
Resin [K2]: a copolymer having a structural unit derived from (a), a structural unit derived from (b), and a structural unit derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, may be referred to as "(c)");
Resin [K3]: a copolymer having a structural unit derived from (a) and a structural unit derived from (c);
Resin [K4]: a copolymer having a structural unit derived from (a) to which (b) has been added, and a structural unit derived from (c);
Resin [K5]: a copolymer having a structural unit derived from (b) to which (a) has been added, and a structural unit derived from (c);
Resin [K6]: A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride, and a structural unit derived from (c).

Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid;
Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid;
Bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;
carboxylic acid anhydrides such as the anhydrides of the above unsaturated dicarboxylic acids except fumaric acid and mesaconic acid;
Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate;
Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid; and the like.
Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the standpoint of copolymerization reactivity and solubility of the resulting resin in an aqueous alkaline solution.
In this specification, the term "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

Monomer (b) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

Examples of monomer (b) include a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b2)"), and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b3)").

Examples of monomer (b1) include a monomer having a structure in which an unsaturated aliphatic hydrocarbon is epoxidized (hereinafter, sometimes referred to as "monomer (b1-1)") and a monomer having a structure in which an unsaturated alicyclic hydrocarbon is epoxidized (hereinafter, sometimes referred to as "monomer (b1-2)").

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable. Specific examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis( glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, etc.

Examples of monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) M100; manufactured by Daicel Corporation), compounds represented by formula (BI) and compounds represented by formula (BII).

In formula (BI) and formula (BII), R ^a and R ^b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a hydroxy group.
X ^a and X ^b each independently represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S- or *-R ^c -NH-.
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* represents a bond to O.

Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl groups.

Examples of alkyl groups in which a hydrogen atom is replaced with a hydroxyl include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.

R ^a and R ^b are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl groups.

^Xa and ^Xb are preferably a single bond, a methylene group, an ethylene group, a * _-CH2 -O- (* represents a bond to O) group, or a * _-CH2CH2 - _O- group, and more preferably a single bond or a * _{-CH2CH2 -} O- group (* represents a bond to O).

Examples of compounds represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among them, compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9) and (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9) and (BI-15) are more preferred.

Compounds represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15), and among these, compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15) are preferred, and compounds represented by formulas (BII-1), (BII-7), (BII-9), and (BII-15) are more preferred.

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone, or the compound represented by formula (BII) may be used in combination. When these are used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20, on a molar basis.

As the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. Examples of the monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, and 3-ethyl-3-(meth)acryloyloxyethyloxetane.

As the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate (commonly known in the art as "dicyclopentanyl (meth)acrylate" and sometimes referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 ^2,6 ]decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 (meth)acrylic acid esters such as tricyclo[ ^{5.2.1.0 2,6} ]decen-8-yl(meth)acrylate (commonly referred to in the technical field as "dicyclopentenyl (meth)acrylate"), tricyclo[5.2.1.0 ^2,6 ]decen-9-yl(meth)acrylate, dicyclopentanyloxyethyl(meth)acrylate, isobornyl(meth)acrylate, adamantyl(meth)acrylate, allyl(meth)acrylate, propargyl(meth)acrylate, phenyl(meth)acrylate, naphthyl(meth)acrylate, and benzyl(meth)acrylate;
Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;
dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate;
Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene chloro[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene bicyclounsaturated compounds such as ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;
dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide;
Examples of the vinyl group-containing aromatic compounds include styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; and dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene.
Of these, from the viewpoints of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-9-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-9-yl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, benzyl(meth)acrylate, and the like are preferred.

In the resin [K1], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K1] is as follows:
Structural units derived from (a): 2 to 60 mol%
Structural units derived from (b): 40 to 98 mol%
It is preferred that
Structural units derived from (a): 10 to 50 mol %
Structural units derived from (b): 50 to 90 mol%
It is more preferable that:
When the ratio of the structural unit of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter tend to be excellent.

Resin [K1] can be produced, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and the references cited in said literature.

Specific examples include a method in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, and the mixture is heated and kept warm while stirring. The polymerization initiator and solvent used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and solvents that dissolve each monomer are sufficient, and examples of the solvent include the solvents described below as the solvent (E) of the colored resin composition of the present invention.

The copolymer obtained may be used as it is in the solution after the reaction, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. In particular, by using a solvent contained in the colored resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is in the preparation of the colored resin composition of the present invention, and the manufacturing process of the colored resin composition of the present invention can be simplified.

In the resin [K2], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K2] is as follows:
Structural units derived from (a): 2 to 45 mol%
Structural units derived from (b): 2 to 95 mol%
Structural units derived from (c): 1 to 65 mol%
It is preferred that
Structural units derived from (a): 5 to 40 mol%
Structural units derived from (b): 5 to 80 mol%
Structural units derived from (c): 5 to 60 mol%
It is more preferable that:
When the ratio of the structural unit of the resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained color filter tend to be excellent.

Resin [K2] can be produced, for example, in the same manner as described for producing resin [K1].

In the resin [K3], the ratio of the structural units derived from each of them to all the structural units constituting the resin [K3] is as follows:
Structural units derived from (a): 2 to 60 mol%
Structural units derived from (c): 40 to 98 mol%
It is preferred that
Structural units derived from (a): 10 to 50 mol %
Structural units derived from (c): 50 to 90 mol%
It is more preferable that:
Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and/or carboxylic acid anhydride contained in (a).
First, a copolymer of (a) and (c) is produced in the same manner as described for the production method of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].

Next, a part of the carboxylic acid and/or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b).
Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air instead of nitrogen, and (b) a catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130° C. for 1 to 10 hours, thereby producing the resin [K4].
The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, relative to 100 moles of (a). By setting it within this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. Since the reactivity of the cyclic ether is high and unreacted (b) is unlikely to remain, (b1) is preferable as (b) used in resin [K4], and (b1-1) is more preferable.
The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c).
The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

Resin [K5] is produced in the first step by the same method as that for producing resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the copolymer obtained may be used as it is in the form of a solution after the reaction, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation.
The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are, respectively,
Structural units derived from (b): 5 to 95 mol%
Structural units derived from (c): 5 to 95 mol%
It is preferred that
Structural units derived from (b): 10 to 90 mol%
Structural units derived from (c): 10 to 90 mol%
It is more preferable that:

Furthermore, under the same conditions as in the production method of resin [K4], resin [K5] can be obtained by reacting a cyclic ether derived from (b) contained in a copolymer of (b) and (c) with a carboxylic acid or carboxylic anhydride contained in (a).
The amount of (a) to be reacted with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) for use in resin [K5], and (b1-1) is more preferred.

Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride is reacted with the carboxylic acid anhydride.
Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of the amount of (a) used.

Specific examples of the resin (B) include resins [K1] such as 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene copolymer, and other resins [K2]; benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer, and other resins [K3]; resins obtained by adding glycidyl (meth)acrylate to a benzyl (meth)acrylate/(meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to a tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, tricyclodecyl Resins [K4] such as a resin obtained by adding glycidyl (meth)acrylate to a (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer; resins [K5] such as a resin obtained by reacting a tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate copolymer with (meth)acrylic acid, a resin obtained by reacting a tricyclodecyl (meth)acrylate/styrene/glycidyl (meth)acrylate copolymer with (meth)acrylic acid; and resins [K6] such as a resin obtained by reacting a tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate copolymer with (meth)acrylic acid and further reacting the resulting resin with tetrahydrophthalic anhydride.

Resin (B) is more preferably resin [K1] or resin [K2], and particularly preferably resin [K1].

The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably from 1,000 to 100,000, more preferably from 2,000 to 50,000, and even more preferably from 3,000 to 30,000. When the weight average molecular weight is within the above range, the solubility of the unexposed portion in a developer is high, and the residual film rate and hardness of the obtained pattern also tend to be high.
The dispersity of the resin (B) [weight average molecular weight (Mw)/number average molecular weight (Mn)] is preferably 1 or more and 6 or less, more preferably 1.001 or more and 4 or less, and even more preferably 1.01 or more and 4 or less.

The acid value of resin (B) (converted to solid content) is preferably 10 mg-KOH/g to 300 mg-KOH/g, more preferably 20 mg-KOH/g to 250 mg-KOH/g, even more preferably 25 mg-KOH/g to 200 mg-KOH/g, even more preferably 30 mg-KOH/g to 150 mg-KOH/g, and particularly preferably 60 mg-KOH/g to 135 mg-KOH/g. The acid value here is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin, and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

The content of resin (B) is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and even more preferably 15 to 30% by mass, based on 100% by mass of the solid content of the colored resin composition. When the content of resin (B) is within the above range, the unexposed portion tends to have high solubility in the developer.

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

Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the above-mentioned monomers (a), (b), and (c).

Examples of polymerizable compounds having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

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, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylenediaminetetraacet ... Examples of the dipentaerythritol hexa(meth)acrylate include ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate, and caprolactone modified dipentaerythritol hexa(meth)acrylate, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 70 or more and 3,500 or less, even more preferably 100 or more and 3,000 or less, even more preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

The content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, and even more preferably 20% by mass or more and 70% by mass or less, based on the total amount of solids in the colored resin composition.

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and any known polymerization initiator can be used.

Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

Examples of O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1-[ 9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine. In addition, as the O-acyloxime compound, commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (both manufactured by BASF) and N-1919 (manufactured by ADEKA Corporation) may be used. Among them, as the O-acyloxime compound, at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferred, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine is more preferred.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercially available alkylphenone compounds such as Irgacure (registered trademark) 369, 907, and 379 (all manufactured by BASF Corporation) may also be used.
Alkylphenone compounds also include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.

Examples of biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).

Triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-( 5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

Further examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.
These are preferably used in combination with a polymerization initiation aid (D1) (particularly an amine compound) described below.

The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

The content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass or less, and more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition. 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, thereby improving the productivity of the color filter.

<Polymerization Initiator Auxiliary Agent (D1)>
The polymerization initiation aid (D1) is a compound used to promote the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D), or a sensitizer. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D).

Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, and preferably 4,4'-bis(diethylamino)benzophenone. In addition, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used as the amine compound.

Examples of alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

Thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

Examples of carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

When these polymerization initiator aids (D1) are used, the content is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition.

<Solvent (E)>
The solvent (E) is not particularly limited, and any solvent commonly used in the relevant field can be used.
Examples of the solvent (E) include ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. Two or more of these solvents may be used in combination.

Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2-ethoxy-2-methylpropionate, Examples of such ether acetates include ethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

Aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene, etc.

Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

The solvent (E) is preferably a solvent containing at least one selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and cyclohexanone.

The content of the solvent (E) is usually 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 95% by mass or less, even more preferably 70% by mass or more and 95% by mass or less, and even more preferably 75% by mass or more and 90% by mass or less, based on the total amount of the colored resin composition. In other words, the total amount of solids in the colored resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 50% by mass or less, even more preferably 5% by mass or more and 30% by mass or less, and even more preferably 10% by mass or more and 25% by mass or less. When the content of the solvent (E) is within the above range, the flatness during application is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics tend to be good.

<Leveling Agent (F)>
Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms, which may have a polymerizable group in the side chain.

Examples of silicone surfactants include surfactants having a siloxane bond in the molecule. Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (product names: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).

Examples of fluorosurfactants include surfactants having a fluorocarbon chain in the molecule. Specific examples include Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), EF-TOP (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by AGC Corporation), and E5844 (manufactured by Daikin Fine Chemicals Research Institute Ltd.).

Examples of silicone surfactants having fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in the molecule. Specific examples include Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and even more preferably 0.005% by mass or more and 0.1% by mass or less, based on the total amount of the colored resin composition. Note that this content does not include the content of the dispersant described above. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Other ingredients>
The colored resin composition may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, and chain transfer agents, as necessary.

<Method of producing colored resin composition>
The colored resin composition can be prepared by mixing the colorant (A), the resin (B), and the polymerizable compound (C), the polymerization initiator (D), the polymerization initiator aid (D1), the solvent (E), the leveling agent (F), and other components that are used as needed. The mixing can be performed using known or conventional equipment and conditions.
The colorant (A) may be mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size is about 0.2 μm or less, and is preferably used in a dispersed state. In this case, the dispersant and a part or all of the resin (B) may be blended as necessary. The colorant (A) may also be used in a state in which it is dissolved in a part or all of the solvent (E) in advance. The remaining components are mixed into the colorant-containing liquid obtained in this way to a predetermined concentration, thereby preparing the desired colored resin composition.

<Color Filter Manufacturing Method>
A color filter, which may be a color conversion layer, can be formed from the colored resin composition of the present invention. Methods for forming a colored pattern include photolithography, inkjet, and printing. Among them, photolithography is preferred. The photolithography is a method in which the colored resin composition is applied to a substrate, dried to form a colored resin composition layer, and the colored resin composition layer is exposed through a photomask and developed. In the photolithography method, a colored coating film, which is a cured product of the colored resin composition layer, can be formed by not using a photomask during exposure and/or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.

The thickness of the color filter to be produced is not particularly limited and can be adjusted appropriately depending on the purpose and application, and is, for example, 0.1 μm to 30 μm, preferably 0.1 μm to 20 μm, and more preferably 0.5 μm to 6 μm.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass with a silica-coated surface, resin plates such as polycarbonate, polymethylmethacrylate, and polyethylene terephthalate, silicon, and the above substrates on which thin films of aluminum, silver, silver/copper/palladium alloy, etc. are formed may be used. On these substrates, other color filter layers, resin layers, transistors, circuits, etc. may be formed.

The formation of each color pixel by photolithography can be carried out using known or conventional devices and conditions. For example, the pixel can be produced as follows.
First, the colored resin composition is applied onto a substrate, and then dried by heating and drying (prebaking) and/or drying under reduced pressure to remove volatile components such as solvents, thereby obtaining a smooth colored resin composition layer.
Examples of the coating method include spin coating, slit coating, and slit and spin coating.
The temperature when drying by heating is preferably from 30° C. to 120° C., and more preferably from 50° C. to 110° C. The heating time is preferably from 10 seconds to 60 minutes, and more preferably from 30 seconds to 30 minutes.
When drying under reduced pressure is performed, it is preferable to perform the drying under a pressure of 50 Pa or more and 150 Pa or less at a temperature range of 20° C. or more and 25° C. or less.
The thickness of the colored resin composition layer is not particularly limited, and may be appropriately selected depending on the intended thickness of the color filter.

Next, the colored resin composition layer is exposed through a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended use is used. In addition, it is preferable to use an exposure device such as a mask aligner or stepper, since it is possible to uniformly irradiate the entire exposed surface with parallel light and to accurately align the photomask with the substrate on which the colored resin composition layer is formed. When a colored coating film is formed, exposure can be performed without using a photomask.

The light source used for exposure is preferably a light source that generates light with a wavelength of 250 nm or more and 450 nm or less. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

The colored resin composition layer after exposure is brought into contact with a developer and developed to form a colored pattern on the substrate. The unexposed portion of the colored resin composition layer is dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may contain a surfactant.
The developing method may be any of a puddle method, a dipping method, a spray method, etc. Furthermore, the substrate may be inclined at an arbitrary angle during the developing.
After development, the substrate is preferably washed with water.

Furthermore, it is preferable to perform post-baking on the obtained colored pattern or colored coating film. The post-baking temperature is preferably 150°C or more and 250°C or less, and more preferably 160°C or more and 240°C or less. The post-baking time is preferably 1 minute or more and 120 minutes or less, and more preferably 10 minutes or more and 60 minutes or less.

<Display device>
The color filter is useful as a color filter for use in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices, particularly as a color filter for use in organic EL devices.

The present invention will be explained in more detail below with reference to examples. However, the present invention is not limited to the following examples, and it is of course possible to carry out the invention with appropriate modifications within the scope of the purpose described above and below, and all such modifications are included in the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass."

In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC: Agilent Model 1200, MASS: Agilent Model LC/MSD6130).

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions.
Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG2000HXL
Column temperature: 40°C
Solvent: tetrahydrofuran Flow rate: 1.0 mL/min Solids concentration of analytical sample: 0.001 to 0.01% by mass
Injection volume: 50μL
Detector: RI
Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
The ratio of the weight average molecular weight and the number average molecular weight (Mw/Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

[Synthesis Example 1]
Preparation of Compound I-19
Compound (I-19) was synthesized according to the description in Chemical Communications 2005, 4045-4046.

Identification of Compound I-19
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 875
Exact Mass: 874

[Synthesis Example 2]
Preparation of Compound I-17
Compound (I-17) was synthesized according to the description in European Journal of Organic Chemistry, 2014, 5178-5195.

Identification of Compound I-17
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 801
Exact Mass: 800

[Synthesis Example 3]
Preparation of Compound I-22
Compound (I-22) was synthesized according to the description in Organic Letters, 2010, Vol. 12, pp. 228-231.

Identification of Compound I-22
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 877
Exact Mass: 876

[Synthesis Example 4]
Preparation of Compound I-18
Compound (I-18) was synthesized according to the description in Organic Letters, 2010, Vol. 12, pp. 228-231.

Identification of Compound I-18
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 802
Exact Mass: 801

Lumogen (registered trademark) F Orange 240 (a compound represented by the following formula (x)) was obtained from Tokyo Chemical Industry Co., Ltd.

[Synthesis Example 5]
A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C while stirring. Next, a mixed solution of 38 parts of acrylic acid, 289 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-yl acrylate (content ratio: 1:1 by molar ratio), and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition was completed, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution having a solid content of 35.1% and a viscosity of 125 mPa·s measured with a Brookfield viscometer (23°C). The weight average molecular weight Mw of the copolymer produced was 9.2×10 ³ , the degree of dispersion was 2.08, and the acid value calculated as solid content was 77 mg-KOH/g. Resin B1 has the following structural units.

Example 1
(1) Preparation of Colored Resin Composition The components were mixed in the following ratio to obtain Colored Resin Composition 1.
(A) Colorant: Compound represented by formula (I- 19 ): 2.6 parts (B) Resin: Resin B1 solution: 54 parts (E) Solvent: Propylene glycol monomethyl ether acetate: 420 parts

(2) Preparation of Colored Curable Resin Composition Next, the components were mixed in the following ratio to obtain colored curable resin composition 1.
Colored resin composition 1 478 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate
(Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 2 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.15 parts

(3) Preparation of colored coating film (color filter) A colored curable resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle XG; manufactured by Corning) so that the film thickness after post-baking was 2 μm, and then pre-baked at 100 ° C. for 3 minutes to form a colored composition layer. After cooling, the colored composition layer formed on the substrate was irradiated with light at an exposure dose of 80 mJ / cm ² (based on 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). After light irradiation, post-baking was performed in an oven at 230 ° C. for 30 minutes to obtain a colored coating film.
The thickness of the resulting colored coating film was measured using DEKTAK3 (manufactured by Japan Vacuum Technology Co., Ltd.) and found to be 2 μm.
The chromaticity of the colored coating film was evaluated by measuring the spectrum using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) and measuring the xy chromaticity coordinates (x, y) and the stimulus value Y in the CIE XYZ color system using the characteristic function of the C light source.

(4) Heat resistance test The obtained colored coating film was heated in an oven under an atmospheric atmosphere at 230°C for 120 minutes. The color difference ΔE ^* ab was calculated from the xy chromaticity coordinates (x, y) and Y measurement value before and after the test by the method described in JIS Z 8730:2009 (7. Calculation method of color difference). The smaller the color difference ΔE ^* ab, the smaller the color change, and if ΔE ^* ab is 5 or less, the colored coating film can be said to have no practical problems as a color filter. In addition, if the heat resistance of the colored coating film is good, it can be said that the heat resistance of a colored pattern made from the same colored curable resin composition is also good. The results are shown in Table 2.

(5) Light resistance test An ultraviolet cut filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co., Ltd.; cuts light of 380 nm or less) was placed on the obtained colored coating film, and xenon lamp light was irradiated for 48 hours using a light resistance tester (SUNTEST CPS+: manufactured by Toyo Seiki Co., Ltd.). The color difference ΔE*ab was calculated by the method described in ^{JIS Z 8730:2009 (7. Calculation method of color difference) from the xy chromaticity coordinates (x, y) and Y measurement values before and after the test. The smaller the color difference ΔE* ab} , the smaller the color change, and if ΔE ^* ab is 5 or less, the colored coating film can be said to have no practical problems as a color filter. In addition, if the light resistance of the colored coating film is good, it can be said that the colored pattern made from the same colored curable resin composition also has good light resistance. The results are shown in Table 2.

<Examples 2 to 4 and Comparative Example 1>
Instead of 2.6 parts of compound (I-19),
2.6 parts of compound (I-17) (Example 2),
2.6 parts of compound (I-22) (Example 3),
A colored curable resin composition was obtained in the same manner as in Example 1, except that 2.6 parts of compound (I-18) (Example 4) or 2.6 parts of Lumogen (registered trademark) F Orange 240 (Comparative Example 1) was used as the colorant. Furthermore, a colored coating film was prepared in the same manner as in Example 1, and the above-mentioned heat resistance test and light resistance test were performed. The results are shown in Table 2.

Claims (4)

A colored resin composition comprising a colorant and a resin, the colorant comprising a compound represented by formula (I).

[In formula (I),
R ¹ to R ¹¹ each independently represent a hydrogen atom, -R ^a1 , -OR ^a1 , a halogen atom, a hydroxy group, a carboxy group, -CO-O-R ^a1 , -O-CO-R ^a1 , -CO-R ^a1 or a nitro group, and R ⁷ and R ⁸ may be bonded to each other to form a ring.
E represents CH, C—R ^a1 or N.
R ^a1 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.] 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 1 or 2. A display device including the color filter according to claim 3.