Colored resin composition, color filter, and display device

Abstract

To provide a colored resin composition that can form a color filter having excellent heat resistance and light resistance.SOLUTION: This invention relates to a colored resin composition that contains a colorant and an alkali-soluble resin, the colorant containing a terylene compound having 8 or more rings fused together.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a colored resin composition, a color filter, and a display device. [Background technology]

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state image sensors such as CCDs and CMOS sensors, are manufactured from colored resin compositions. Various colorants are used as colored resin compositions for forming these color filters, and for example, an example in which Lumogen® F Orange240, which has a carbon condensed ring structure, is used in the colored composition is known (Patent Document 1).

[0003] [ka] [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2020-79396 [Overview of the project] [Problems that the invention aims to solve]

[0005] However, conventionally known colored compositions containing the above-mentioned compounds sometimes failed to provide sufficient heat resistance and light resistance. Therefore, the present invention aims to provide a colored resin composition capable of forming a color filter with excellent heat resistance and light resistance. [Means for solving the problem]

[0006] The gist of this invention is as follows: [1] A colored resin composition comprising a colorant and an alkali-soluble resin, wherein the colorant comprises a terylene compound having a structure in which eight or more rings are condensed. [2] The colored resin composition according to [1], wherein the terrylene compound is a compound represented by formula (I). [Chemical formula] [In formula (I), R 1 , 18 , 4 , , 17 , 4 , 17 , 17 , 2 , 4 , 17 , , 18 , 1 , 1 , 3 , 17 ~R 4 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxy group or a carboxy group, and the methylene group contained in the hydrocarbon group may be replaced by -O-, -CO- or -N(R 17 ). R 1 and R 4 and R 2 and R 3 may combine with each other to form a ring. R 5 ~R 16 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a hydrogen atom, a halogen atom, a hydroxy group, a carboxy group or a nitro group, and the methylene group contained in the hydrocarbon group may be replaced by -O-, -CO- or -N(R 17 ). R 17 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. When there are a plurality of R 17 , they may be the same or different from each other.] [3] R 1 ~R 4 each independently is -CO-O-R 18 (wherein R 18 represents a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and the methylene group contained in the hydrocarbon group may be replaced by -O-, -CO- or -N(R[[ID=​​​​​​​​​​​​​or R 2 and R 3 A colored resin composition as described in [1] or [2], represented by a bond with [2]. [4] A colored resin composition according to any one of [1] to [3], further comprising a polymerizable compound and a polymerization initiator. A color filter formed from any of the colored resin compositions described in [5][1] to [4]. A display device including the color filter described in [6][5]. [Effects of the Invention]

[0007] According to the present invention, a color filter with excellent heat resistance and light resistance can be provided. [Modes for carrying out the invention]

[0008] The colored resin composition of the present invention may be for use as a photoresist and comprises a coloring agent (hereinafter sometimes referred to as coloring agent (A)) and an alkali-soluble resin (hereinafter sometimes referred to as resin (B)). The colored resin composition of the present invention may contain a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)). The colored resin composition of the present invention may further contain a solvent (hereinafter sometimes referred to as solvent (E)). The colored resin composition of the present invention may further contain a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D1)). The colored resin composition of the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)). In this specification, the compounds exemplified as components may be used individually or in combination, unless otherwise specified.

[0009] <Coloring agent (A)> The coloring agent (A) contains a terylene compound having a structure in which eight or more rings are fused together. The terylene compound is a compound having a tribenzo[de,kl,rst]pentafene skeleton (also called a terylene skeleton). The terylene compound is preferably a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)). Compound (I) may be used alone or in combination of two or more types.

[0010] <<Compound (I)>> [ka]

[0011] [In formula (I), R 1 ~R 4 Each of these independently represents a C1-C20 hydrocarbon group, a halogen atom, a hydroxyl group, or a carboxyl group, which may have substituents, and the methylene group contained in the hydrocarbon group is -O-, -CO-, or -N(R 17 )- may be replaced with this. R 1 and R 4 and R 2 and R 3 These elements may be joined together to form a ring. R 5 ~R 16 Each of these independently represents a C1-C20 hydrocarbon group, a hydrogen atom, a halogen atom, a hydroxyl group, a carboxyl group, or a nitro group, which may have substituents, and the methylene group contained in the hydrocarbon group is -O-, -CO-, or -N(R 17 )- may be replaced with this. R 17 R represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. 17 If multiple instances exist, they may be identical or different from one another.

[0012] R 1 ~R 16 Examples of halogen atoms represented by this formula include fluorine, chlorine, bromine, and iodine atoms.

[0013] R 1 ~R 17Examples of hydrocarbon groups having 1 to 20 carbon atoms represented by include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. Aliphatic hydrocarbon groups may be saturated or unsaturated, and may be linear or alicyclic.

[0014] R 1 ~R 17 The saturated or unsaturated linear hydrocarbon groups represented by 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 eicosyl; isopropyl, (1-methyl)propyl, (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, (1-propyl)butyl, (1-propyl (Tyl)pentyl 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 Examples include branched alkyl groups such as tyl groups, (2-ethyl)nonyl groups, and (1-octyl)nonyl groups; and alkenyl groups such as vinyl groups, 1-propenyl groups, 2-propenyl groups (allyl groups), (1-methyl)ethenyl groups, 2-butenyl groups, 3-butenyl groups, 1,3-butadienyl groups, (1-(2-propenyl))ethenyl groups, (1,2-dimethyl)propenyl groups, and 2-pentenyl groups. The number of carbon atoms in saturated chain hydrocarbon groups is preferably 1 to 18, more preferably 2 to 15, and even more preferably 3 to 12. The number of carbon atoms in unsaturated chain hydrocarbon groups is preferably 2 to 18, more preferably 2 to 15, and even more preferably 3 to 12.

[0015] R1 ~R 17 Examples of saturated or unsaturated alicyclic hydrocarbon groups represented by include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohexa-2-ene, cyclohexa-3-ene), cycloheptenyl, and cyclooctenyl; norbornyl, adamantyl, and bicyclo[2.2.2]octyl groups. The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 15, and more preferably 3 to 12.

[0016] R 1 ~R 17 Examples of aromatic hydrocarbon groups represented by include phenyl group, 1-naphthyl group, 2-naphthyl group, phenanthryl group, anthryl group, pyrenyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 15, and more preferably 6 to 12.

[0017] R 1 ~R 17The hydrocarbon group represented by may be a group formed by combining two or more of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, as long as the upper limit of the number of carbon atoms is 20 or less. Such a group may be, for example, a group formed by combining an aromatic hydrocarbon group with at least one group selected from chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and in the hydrocarbon group formed by this combination, the chain hydrocarbon group may be combined as a divalent group (for example, an alkanediyl group). Examples of hydrocarbon groups formed by combinations include aralkyl groups such as benzyl group, phenethyl group, 1-methyl-1-phenylethyl group, tert-butylphenyl group, tert-octylphenyl group, tert-butylbenzyl group, and tert-octylbenzyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group); arylalkynyl groups such as phenylethynyl group; o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, and m-isopropylphenyl group. Alkylaryl groups such as p-isopropylphenyl, 2,3-diisopropylphenyl, 2,4-diisopropylphenyl, 2,5-diisopropylphenyl, 2,6-diisopropylphenyl, 2,4,6-triisopropylphenyl, 4-butylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 2,6-di(tert-butyl)phenyl, 3,5-di(tert-butyl)phenyl, 3,6-di(tert-butyl)phenyl, 4-tert-butyl-2,6-dimethylphenyl, 4-pentylphenyl, 4-octylphenyl, 4-(2,4,4-trimethyl-2-pentyl)phenyl, 2-dodecylphenyl, 3-dodecylphenyl, and 4-dodecylphenyl;Examples include aryl groups to which alkanediyl groups such as 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-4-s-indacenyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, 3-methyl-5,6,7,8-tetrahydro-2-naphthyl group, and 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group are attached; aryl groups to which one or more aryl groups such as biphenylyl group and terphenylyl group are attached; and cyclohexylmethylphenyl group, benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group, etc. Furthermore, the above hydrocarbon group may be a hydrocarbon group formed by a combination of a chain hydrocarbon group and an alicyclic hydrocarbon group, for example, 1-methylcyclopropyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6- Alicyclic hydrocarbon groups to which one or more alkyl groups are attached, such as dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 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;Examples include 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 groups combining two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups is preferably 6 to 18, more preferably 6 to 15.

[0018] R 1 ~R 17The substituents that the C1-C20 hydrocarbon group represented by may have include, for example, halogen atoms; nitrile groups; nitro groups; amino groups; hydroxyl groups; alkoxy groups with C1-C20 such as methoxy and ethoxy groups; aryloxy groups with C6-C20 such as phenyloxy, 1-naphthyloxy, and 2-naphthyloxy groups; thiol groups; alkylthio groups with C1-C20 such as methylthio and ethylthio groups; allylthio groups; arylthio groups with C6-C20 such as phenylthio, 1-naphthylthio, and 2-naphthylthio groups; sulfoxy groups; alkylsulfoxy groups with C1-C20 such as methylsulfoxy and ethylsulfoxy groups; arylsulfoxy groups with C6-C20 such as phenylsulfoxy, 1-naphthylsulfoxy, and 2-naphthylsulfoxy groups; silyl groups; boryl groups; monomethylamino groups, dimethyl Examples include alkylamino groups having 1 to 20 carbon atoms, such as diamino groups, trimethylamino groups, monoethylamino groups, diethylamino groups, and triethylamino groups; arylamino groups having 6 to 20 carbon atoms, such as monophenylamino groups, diphenylamino groups, and triphenylamino groups; aralkylamino groups having 7 to 20 carbon atoms, such as benzylamino groups; carboxyl groups; carbamoyl groups; alkylcarbonyl groups having 2 to 20 carbon atoms, such as acetyl groups and propionyl groups; arylcarbonyl groups having 7 to 20 carbon atoms, such as benzoyl groups, 1-naphthylcarbonyl groups, and 2-naphthylcarbonyl groups; alkoxycarbonyl groups having 2 to 20 carbon atoms, such as methoxycarbonyl groups and ethoxycarbonyl groups; and aryloxycarbonyl groups having 7 to 20 carbon atoms, such as phenyloxycarbonyl groups, 1-naphthyloxycarbonyl groups, and 2-naphthyloxycarbonyl groups.

[0019] R 1 ~R 16 The methylene group (-CH2-) contained in the hydrocarbon group with 1 to 20 carbon atoms represented by is -O-, -CO-, or -N(R 17 )- may be replaced with this.

[0020] R 1 ~R 16When the -CH2- contained in the hydrocarbon group represented by is replaced by -O- or -CO-, the number of replacements may be one or two or more. Furthermore, when the -CH2- contained in the hydrocarbon group is replaced by -O- or -CO-, the number of carbon atoms before replacement is considered the number of carbon atoms in the hydrocarbon group. 1 ~R 16 Specifically, groups in which the -CH2- contained in the hydrocarbon group represented by is replaced by -O- or -CO- include the groups represented by formulas (Y-1) to (Y-60) below. * represents a bond.

[0021] [ka]

[0022] [ka]

[0023] [ka]

[0024] R 1 ~R 16 The -CH2- contained in the hydrocarbon group represented by -N(R 17 When replaced by -, the number may be one or two or more. Note that -CH2- contained in the hydrocarbon group may be -N(R 17 When replaced by ), the number of carbon atoms before replacement shall be the number of carbon atoms of the hydrocarbon group. 1 ~R 16 The -CH2- contained in the hydrocarbon group represented by -N(R 17 Specifically, the groups that have been replaced by ) are those represented by the following formulas (Z-1) to (Z-48). * represents a bond.

[0025] [ka]

[0026] [Chemical formula]

[0027] R 1 and R 4 and R 2 and R 3 may be bonded to each other to form a ring.

[0028] R 1 and R 4 and R 2 and R 3 Examples of the ring that may be formed by bonding with each other include *-CO-O-CO-* or *-CO-N(R 17 )-CO-*, etc. R 1 and R 4 R 2 and R 3 Examples of the ring containing *-CO-O-CO-* or *-CO-N(R 17 )-CO-* formed by R 1 and R 4 R 2 and R 3 independently of each other are divalent groups represented by the following formulas (H-1) to (H-16). In formulas (H-1) to (H-16), * represents a bond to the tellurene skeleton possessed by R<t 1 and R 4 R 2 and R 3 .

[0029] [Chemical formula]

[0030] [Chemical formula]

[0031] R 1 ~R 4 are independently of each other -CO-O-R 18 (wherein R 18represents a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and the methylene group contained in the hydrocarbon group may be replaced by -O-, -CO- or -N(R 17 ).), or at least one selected from the group consisting of R 1 and R 4 and R 2 and R 3 is preferably represented by *-CO-N(R 17 )-CO-* (where * represents a bond with R 1 and R 4 or R A 2 and R 3 ).

[0032] The hydrocarbon group having 1 to 18 carbon atoms represented by R 18 may be the same as the hydrocarbon group having 1 to 18 carbon atoms among the hydrocarbon groups having 1 to 20 carbon atoms represented by R 1 to R 17 . <00_{00467}R 1 to R 4 are each independently -CO-O-R 18 , or it is more preferable that R 1 and R 4 and R 2 and R 3 are each independently represented by *-CO-N(R 17 )-CO-*.

[0033] That is, the compound represented by formula (I) may be one or more selected from the group consisting of the compound represented by formula (I-A), the compound represented by formula (I-B), and the compound represented by formula (I-C), and it is preferable that the compound is the compound represented by formula (I-A) and the compound represented by formula (I-C).

[0034]

Chemical formula

[0036] R 18a ~R 18d is the aforementioned R 18 It expresses the same meaning.

[0037] [ka]

[0038] [In the formula, R 5 ~R 17 These two expressions, independently of each other, represent the same meaning as above. 18e and R 18f Each represents a hydrocarbon group having 1 to 18 carbon atoms, which may have substituents, and the methylene group contained in the hydrocarbon group is -O-, -CO-, or -N(R 17 )- may be replaced with R 17a This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents.

[0039] R 18e ~R 18f is the aforementioned R 18 It expresses the same meaning. R 17a is the aforementioned R 17 It expresses the same meaning.

[0040] [ka]

[0041] [In the formula, R 5 ~R 17 These two expressions, independently of each other, represent the same meaning as above. 17b and R 17c These terms independently represent hydrocarbon groups having 1 to 20 carbon atoms, which may have substituents.

[0042] R 17b ~R 17c is the aforementioned R 17 It expresses the same meaning.

[0043] R in equation (I) 1 ~R 4 -CO-OR may be represented as 18 R possessed 18 , the -CO-OR of formula (IA) 18a ~-CO-OR 18d R possessed 18a ~R 18d , formula (IB) -CO-OR 18e ~-CO-OR 18f R possessed 18e ~R 18f For example, the above R 1 ~R 17 Among the hydrocarbon groups having 1 to 20 carbon atoms represented by , those having 1 to 18 carbon atoms are mentioned, and it is preferable that they are saturated chain hydrocarbon groups, saturated alicyclic hydrocarbon groups, groups combining alicyclic hydrocarbon groups and chain hydrocarbon groups, aromatic hydrocarbon groups, or groups combining aromatic hydrocarbon groups and chain hydrocarbon groups. It is more preferable that they are saturated chain hydrocarbon groups having 1 to 18 carbon atoms, saturated alicyclic hydrocarbon groups having 3 to 15 carbon atoms, groups combining alicyclic hydrocarbon groups having 4 to 15 carbon atoms and chain hydrocarbon groups, aromatic hydrocarbon groups having 6 to 18 carbon atoms, or groups combining aromatic hydrocarbon groups having 7 to 18 carbon atoms and chain hydrocarbon groups. It is even more preferable that they are saturated chain hydrocarbon groups having 3 to 18 carbon atoms, groups combining alicyclic hydrocarbon groups having 4 to 10 carbon atoms and chain hydrocarbon groups, or groups combining aromatic hydrocarbon groups having 7 to 15 carbon atoms and chain hydrocarbon groups. These substituents are R 1 ~R 17 This has the same meaning as a substituent that may be present on a hydrocarbon group having 1 to 20 carbon atoms, represented by [the symbol].

[0044] Also, R in equation (I) 1 ~R 4 -CO-OR may be represented as 18 , the -CO-OR of formula (IA)18a ~-CO-OR 18d , formula (IB) -CO-OR 18e ~-CO-OR 18f For example, the above R 1 ~R 17 Examples include oxycarbonyl groups having 1 to 18 carbon atoms among hydrocarbon groups having 1 to 20 carbon atoms represented by , as well as alkoxycarbonyl groups having 1 to 18 carbon atoms and aryloxycarbonyl groups having 1 to 18 carbon atoms.

[0045] R in equation (I) 1 ~R 4 -CO-OR may be represented as 18 , the -CO-OR of formula (IA) 18a ~-CO-OR 18d , formula (IB) -CO-OR 18e ~-CO-OR 18f Specifically, these include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, (1-methyl)propoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, (1-ethyl)pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxycarbonyl group, (1-butyl)heptyloxycarbonyl group, octyloxycarbonyl group, and (1-heptyl)octyloxy Examples include carbonyl groups, nonyloxycarbonyl groups, decyloxycarbonyl groups, undecyloxycarbonyl groups, dodecyloxycarbonyl groups, tridecyloxycarbonyl groups, tetradecyloxycarbonyl groups, pentadecyloxycarbonyl groups, hexadecyloxycarbonyl groups, heptadecyloxycarbonyl groups, octadecyloxycarbonyl groups, phenyloxycarbonyl groups, benzyloxycarbonyl groups, cyclohexyloxycarbonyl groups, cyclohexylmethoxycarbonyl groups, and eicosyloxycarbonyl groups.

[0046] Among these, methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, (1-methyl)propoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, (1-ethyl)pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, and octyloxycarbonyl group are preferred, with ethoxycarbonyl group and propoxycarbonyl group being preferred. Bonyl group, (1-methyl)propoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, and octyloxycarbonyl group are more preferred, and ethoxycarbonyl group, (1-methyl)propoxycarbonyl group, butoxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, and octyloxycarbonyl group are even more preferred.

[0047] The aforementioned *-CO-N(R 17 The ring containing )-CO-* has R 17 , the aforementioned *-CO-N(R 17a The ring containing )-CO-* has R 17a , the aforementioned *-CO-N(R 17b The ring containing )-CO-* has R 17b , the aforementioned *-CO-N(R 17c The ring containing )-CO-* has R 17c Examples include the same C1-C20 hydrocarbon groups that may have substituents as described above, and are preferably saturated chain hydrocarbon groups that may have substituents, aromatic hydrocarbon groups that may have substituents, or groups that are a combination of an aromatic hydrocarbon group that may have substituents and a chain hydrocarbon group. More preferably are saturated chain hydrocarbon groups that may have substituents, aromatic hydrocarbon groups that may have substituents, or groups that are a combination of an aromatic hydrocarbon group that may have substituents and a chain hydrocarbon group. Even more preferably are saturated chain hydrocarbon groups that have substituents and a chain hydrocarbon group, or groups that are a combination of an aromatic hydrocarbon group that may have substituents and a chain hydrocarbon group. These substituents are R 1 ~R 17 This has the same meaning as a substituent that may be present on a hydrocarbon group having 1 to 20 carbon atoms, represented by [the symbol].

[0048] Also, R in equation (I) 17 R in equation (IB) 17a R in equation (IC) 17b ~R 17c Examples of carbon-hydrogen groups with 1 to 20 carbon atoms represented by the following formulas (D-1) to (D-47) and (G-1) to (G-24). * represents a bond.

[0049] [ka]

[0050] [ka]

[0051] R 1 and R 4 And / or R 2 and R 3 *-CO-N(R) may be formed. 17 )-CO-*, *-CO-N(R 17a )-CO-*, *-CO-N(R 17b )-CO-*, *-CO-N(R 17c )-CO-* is preferably a group represented by formula (H-9). Specifically, examples of groups represented by formula (H-9) include the groups represented by formulas (H-9-1) to (H-9-16) below. In formulas (H-9-1) to (H-9-16), * is R 1 and R 4 , R 2 and R 3 This represents the bonding relationship with the terylene skeleton that it possesses. In particular, formulas (H-9-7) to (H-9-12) are preferred, and formula (H-9-9) is especially preferred.

[0052] [ka]

[0053] In equations (I), (IA), (IB), and (IC), R 5 ~R 16 These are preferably, independently of each other, a hydrogen atom, a halogen atom, or a C1-C20 hydrocarbon group which may have substituents; more preferably, a hydrogen atom, a halogen atom, or a C6-C20 hydrocarbon group which may have substituents; and even more preferably, a hydrogen atom, a halogen atom, or a C12-C20 carbon-hydrogen group which may have substituents. The methylene group contained in this carbon-hydrogen group may be replaced with -O- or -CO-. In particular, in equation (IA), R 5 ~R 16 It is particularly preferable that these atoms are hydrogen atoms, independently of each other. In equation (IC), R 5 , R 7 , R 8 , R 10 , R 11 , R 13 , R 14 , and R 16 Preferably, each is independently a hydrogen atom, a halogen atom, or a C1-C20 hydrocarbon group which may have substituents; more preferably a hydrogen atom, a halogen atom, or a C6-C20 hydrocarbon group which may have substituents; even more preferably a combination of a hydrogen atom, a halogen atom, or a C6-C19 aromatic hydrocarbon group and a C1-C14 aliphatic hydrocarbon group; even more preferably a combination of a hydrogen atom, a halogen atom, or a phenoxy group or a phenoxy group and a C1-C10 linear alkyl group or branched alkyl group, with a hydrogen atom being particularly preferred. In equation (IC), R 6 , R 9 , R 12 , and R 15Preferably, each is independently a hydrogen atom, a halogen atom, or a C1-C20 hydrocarbon group which may have substituents; more preferably a hydrogen atom, a halogen atom, or a C6-C20 hydrocarbon group which may have substituents; even more preferably a combination of a hydrogen atom, a halogen atom, or a C6-C19 aromatic hydrocarbon group and a C1-C14 aliphatic hydrocarbon group; even more preferably a combination of a hydrogen atom, a halogen atom, or a phenoxy group or a phenoxy group and a C1-C10 linear alkyl group or branched alkyl group; and particularly preferably a combination of a hydrogen atom, a bromine atom, or a phenoxy group and a tert-butyl group or a tert-octyl group (e.g., p-tert-butylphenoxy group, p-tert-octylphenoxy group).

[0054] The compounds represented by formula (I) are preferably those represented by formulas (Ia-1) to (Ia-459), (Ib-1) to (Ib-175), and (Ic-1) to (Ic-185), as shown in Tables 1 to 33.

[0055] [Table 1]

[0056] [Table 2]

[0057] [Table 3]

[0058] [Table 4]

[0059] [Table 5]

[0060] Table 6

[0061] Table 7

[0062] Table 8

[0063] Table 9

[0064] Table 10

[0065] Table 11

[0066] Table 12

[0067] Table 13

[0068] Table 14

[0069] Table 15

[0070] Table 16

[0071] Table 17

[0072] Table 18

[0073] Table 19

[0074] Table 20

[0075] Table 21

[0076] Table 22

[0077] Table 23

[0078] Table 24

[0079] Table 25

[0080] Table 26

[0081] [Table 27]

[0082] [Table 28]

[0083] [Table 29]

[0084] [Table 30]

[0085] [Table 31]

[0086] [Table 32]

[0087] [Table 33]

[0088] In Tables 1-23, *COOEt, *COOPr, *COO(1-MtPr), *COOBu, *COOHex, *COO(2-EtHex), and *COOOct represent an ethoxycarbonyl group, a propoxycarbonyl group, a 1-methylpropoxycarbonyl group, a butoxycarbonyl group, a hexyloxycarbonyl group, a 2-ethylhexyloxycarbonyl group, and an octyloxycarbonyl group, respectively. * indicates a bond with the terylene skeleton. In Tables 19-33, (H-9-7) to (H-9-12) are the same as the structures represented by the above formulas (H-9-7) to (H-9-12). p-tert-Oct-C6H4O*, C6H4O*, and p-tert-Bu-C6H4O* represent the p-tert-octylphenoxy group, phenoxy group, and p-tert-butylphenoxy group, respectively. * indicates a bond with the terylene skeleton.

[0089] Among the compounds represented by formulas (Ia-1) to (Ia-459) above, compounds represented by formulas (Ib-1) to (Ib-175) above, and compounds represented by formulas (Ic-1) to (Ic-185) above, the compounds represented by formula (Ia-14), the compounds represented by formula (Ia-28), the compounds represented by formula (Ia-42), the compounds represented by formula (Ia-56), the compounds represented by formula (Ia-57), the compounds represented by formula (Ia-142), and the compounds represented by formula (Ia-218), Compounds represented by formula (Ib-1), compounds represented by formula (Ib-6), compounds represented by formula (Ib-11), compounds represented by formula (Ib-16), compounds represented by formula (Ib-21), compounds represented by formula (Ib-26), compounds represented by formula (Ib-31), compounds represented by formula (Ib-37), compounds represented by formula (Ib-42), compounds represented by formula (Ib-47), compounds represented by formula (Ib-52), compounds represented by formula (Ib-57), compounds represented by formula (Ib-62), compounds represented by formula (Ib-67), compounds represented by formula (Ib-73), compounds represented by formula (Ib-78), compounds represented by formula (Ib-83), compounds represented by formula (Ib-88), Compounds represented by formula (Ib-93), compounds represented by formula (Ib-98), compounds represented by formula (Ib-103), compounds represented by formula (Ib-109), compounds represented by formula (Ib-114), compounds represented by formula (Ib-119), compounds represented by formula (Ib-124), compounds represented by formula (Ib-129), compounds represented by formula (Ib-134), compounds represented by formula (Ib-139), compounds represented by formula (Ib-145), compounds represented by formula (Ib-150), compounds represented by formula (Ib-155), compounds represented by formula (Ib-160), compounds represented by formula (Ib-165), compounds represented by formula (Ib-170), compounds represented by formula (Ib-175), Compounds represented by formula (Ic-1), formula (Ic-8), formula (Ic-15), formula (Ic-22), formula (Ic-29), formula (Ic-36), formula (Ic-37), formula (Ic-38), formula (Ic-45), formula (Ic-52), formula (Ic-59), formula (Ic-66), formula (Ic-73), formula (Ic-74), formula (Ic-75), formula (Ic-82), formula (Ic-89), formula (Ic-96), formula (Ic-103), formula (Ic-110), and formula (Ic-111) are preferred. Compounds represented by formula (Ia-14) (compound (I-2)), compound represented by formula (Ia-42) (compound (I-6)), compound represented by formula (Ia-56) (compound (I-5)), compound represented by formula (Ia-57) (compound (I-4)), compound represented by formula (Ia-218) (compound (I-7)), compound represented by formula (Ic-15) (compound (I-1)), compound represented by formula (Ic-37) (compound (I-3)), compound represented by formula (Ic-52) (compound (I-8)), compound represented by formula (Ic-74), compound represented by formula (Ic-89), and compound represented by formula (Ic-111) are more preferably used. Compounds represented by formula (Ia-14) (compound (I-2)), compound represented by formula (Ia-42) (compound (I-6)), compound represented by formula (Ia-56) (compound (I-5)), compound represented by formula (Ia-57) (compound (I-4)), compound represented by formula (Ia-218) (compound (I-7)), compound represented by formula (Ic-15) (compound (I-1)), compound represented by formula (Ic-37) (compound (I-3)), compound represented by formula (Ic-52) (compound (I-8)), and compound represented by formula (Ic-89) are even more preferred.

[0090] Compound (I) can be prepared, for example, according to Route 1 or Route 2. Route 1 consists of the steps of (1-i) reacting a compound represented by formula (pt-1) with a compound represented by formula (MA-1) (hereinafter sometimes referred to as compound (MA-1)) to obtain a compound represented by formula (pt-2), (1-ii) reacting a compound represented by formula (pt-3) and a compound represented by formula (pt-3') with a compound represented by formula (MA-2) to obtain a compound represented by formula (pt-4) and a compound represented by formula (pt-4'), and (1-iii) reacting a compound represented by formula (pt-4) and a compound represented by formula (pt-2) to obtain compound (I). Route 2 consists of the following steps: (2-i) reacting a compound represented by formula (pt-5) with a compound represented by formula (MA-3) to obtain a compound represented by formula (pt-6); (2-ii) reacting a compound represented by formula (pt-7) with a compound represented by formula (MA-4) to obtain a compound represented by formula (pt-8); (2-iii) reacting a compound represented by formula (pt-8) with a compound represented by formula (MA-1) to obtain a compound represented by formula (pt-9); (2-iv) reacting a compound represented by formula (pt-6) with a compound represented by formula (pt-9) to obtain a compound represented by formula (pt-10); and (2-v) reacting a compound represented by formula (pt-10) with a base to obtain compound (I).

[0091] In the following (pt-1) to (pt-10), R 1 ~R 16 This expresses the same meaning as above. In (MA-1), (pt-2), and (pt-9), R B1 These are, independently, 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, and two R groups. B1 Examples of ring-forming groups include 2,2-dimethylpropyl-1,3-diyl group, 2,3-dimethylbutyl-2,3-diyl group, 2-dimethylpentyl-2,4-diyl group, and 1,2-phenylene group. In (MA-1), R B2 These can be independently a hydrogen atom, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, a pianocolatoboryl group, a catecholboryl group, a neopentylglycolatoboryl group, a hexyleneglycolatoboryl group, and so on. (MA-1) is preferably bis(pinacolato)diborone, bis(neopentylglycolato)diborone, or bis(hexyleneglycolato)diborone.

[0092] [ka]

[0093] Examples of compounds (pt-1) include 1,4-dibromonaphthalene.

[0094] The compound (MA-1) used in step (1-i) is preferably bis(pinacolato)diborone, bis(catecorato)diborone, bis(neopentylglycolato)diborone, pinacolborane, catecorborane, neopentyl glycolborane, or 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneisopropoxyboronic acid pinacol, with bis(pinacolato)diborone and pinacolborane being more preferred. The amount of compound (MA-1) used is usually 1 mole to 100 moles, more preferably 1 mole to 10 moles, and even more preferably 1 mole to 5 moles, per mole of the compound represented by formula (pt-1). It is preferable to carry out the reaction in the presence of a catalyst, a base, and a solvent. Examples of catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride and bis(triphenylphosphine)palladium(II) dichloride. Examples of bases include potassium acetate, sodium acetate, and potassium phenoxide. The amount of catalyst used is typically 0.01 moles or more and 1 mole or less per mole of the compound represented by formula (pt-1), more preferably 0.01 moles or more and 0.3 moles or less, and even more preferably 0.01 moles or more and 0.15 moles or less. The amount of base used is typically 1 mole to 50 moles, more preferably 1 mole to 20 moles, and even more preferably 1 mole to 10 moles, per mole of the compound represented by formula (pt-1).

[0095] Examples of the aforementioned solvents include 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, tetrahydrofuran, cyclopentyl methyl ether, and 1,4-dioxane; 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; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole, but dimethyl sulfoxide, N,N-dimethylformamide, and cyclopentyl methyl ether are preferred. The amount of solvent used is, for example, 1 to 1000 parts by mass relative to the compound represented by formula (pt-1).

[0096] The reaction temperature is typically between -100°C and 300°C.

[0097] In step (1-ii), X in the compounds represented by formulas (pt-3) and (pt-3') represents a halogen atom, preferably a chlorine atom and a bromine atom. R in the compounds represented by formulas (pt-4) and (pt-4') 1 ~R 4 However, independently of each other, *-CO-OR 18 Compounds represented by (* represents a bond) (hereinafter, they may be referred to as compound (pt-4-1) and compound (pt-4-1'), respectively) are the same as the compound represented by formula (pt-3) and / or the compound represented by formula (pt-3') and R 18 -OH (sometimes referred to as compound (MA-2-1)), R 18-X (sometimes referred to as compound (MA-2-2)) can be produced by reacting it in a solvent. Compound (MA-2-1) may be used alone or in combination of two or more types, and compound (MA-2-2) may also be used alone or in combination of two or more types. The compound represented by formula (pt-4) and the compound represented by formula (pt-4') are R 1 and R 4 , and R 2 and R 3 However, independently of each other, together, *-CO-N(R 17 Compounds that form a )-CO-* (* represents a bond) (hereinafter, they may be referred to as compound (pt-4-2) and compound (pt-4-2'), respectively) are the compound represented by formula (pt-3) and the compound represented by formula (pt-3') and R 17 It can be produced by reacting -NH2 (sometimes referred to as compound (MA-2-3)) in a solvent.

[0098] Examples of compounds (pt-3) and (pt-3') include 4,5-dibromo-1,8-naphthalenedicarboxylic acid anhydride.

[0099] The total amount used of the compound represented by formula (MA-2-1) and the compound represented by formula (MA-2-2) is usually between 1 mole and 20 moles, preferably between 1 mole and 15 moles, and more preferably between 1 mole and 10 moles, per mole of the total amount of compounds (pt-3) and (pt-3').

[0100] The amount of compound represented by formula (MA-2-3) used is usually 1 mole to 10 moles, preferably 1 mole to 8 moles, more preferably 1 mole to 6 moles, and even more preferably 1 mole to 4 moles, per 1 mole of the total amount of compounds (pt-3) and (pt-3').

[0101] Examples of the aforementioned solvents 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; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole.

[0102] The amount of solvent used is typically 1 to 1000 parts by mass per 1 part by mass of the total amount of compounds (pt-3) and (pt-3'), whether producing compounds (pt-4-1) and (pt-4-1') or compounds (pt-4-2) and (pt-4-2').

[0103] The reaction temperature is typically between -100°C and 300°C, whether producing compound (pt-4-1) or compound (pt-4-2).

[0104] Compound (I) in step (1-iii) can be produced by reacting the compound represented by formula (pt-2) (sometimes referred to as compound (pt-2)), the compound represented by formula (pt-4), and the compound represented by formula (pt-4') in a solvent in the presence of a catalyst, a phosphine ligand, and a base.

[0105] Examples of the catalyst include tris(dibenzylideneacetone)dipalladium(0), bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, palladium(II) chloride, sodium tetrachloropalladium(II)ate, palladium(II)(π-cinnamyl) chloride (dimer), allylpalladium(II) chloride dimer, bis(benzonitrile)palladium(II) dichloride, and bis(acetonitrile)palladium(II) dichloride, with bis(dibenzylideneacetone)palladium(0) being more preferred.

[0106] 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-butylphosphine)biphenyl, di-tert-butyl(1,1-diphenyl-1-propen-2-yl)phosphine, isopropyldiphenylphosphine, 2-(dicyclohexylphosphine)-2'-(dimethylamino)biphenyl, 2-(dicyclohexylphosphine)biphenyl, 2-(diphenylphosphine)biphenyl, 2-dicyclohexylphosphine-2'-methylbiphenyl, 2-dicyclohexylphosphine-2',6'-diisopropoxybiphenyl, 2-dicyclohexylphosphine-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, dicyclohexyl(1,Monodentate phosphine ligands such as 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, 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. Preferably, monodentate phosphine ligands are used, more preferably tributylphosphine, tri-tert-butylphosphine, and tricyclohexylphosphine, and most preferably tricyclohexylphosphine.

[0107] Examples of the aforementioned bases include hydroxides, carbonates, bicarbonates, phosphates, carboxylates, and alkoxides of alkali metals or alkaline earth metals, which are inorganic bases. The base used may be in an anhydrous or hydrated form. Preferably, examples include hydroxides, carbonates, bicarbonates, phosphates, and carboxylates of alkali metals or alkaline earth metals, with alkali metal or alkaline earth metal carbonates and phosphates being more preferred. Preferred alkali metal or alkaline earth metal salts include lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, barium carbonate, lithium phosphate, sodium phosphate, and potassium phosphate, with sodium carbonate, potassium carbonate, and potassium phosphate being more preferred.

[0108] Examples of the aforementioned solvents 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; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole, with xylene and toluene being preferred.

[0109] The amount of catalyst used is typically 0.01 moles to 1 mole per mole of compound (pt-2), more preferably 0.01 moles to 0.5 moles, and even more preferably 0.01 moles to 0.25 moles. The amount of phosphine ligand used is typically 0.01 moles to 3 moles, more preferably 0.02 moles to 1 mole, and even more preferably 0.02 moles to 0.5 moles, per mole of the compound represented by formula (pt-1). The amount of base used is typically 1 mole to 50 moles per mole of compound (pt-2), more preferably 1 mole to 25 moles, and even more preferably 1 mole to 15 moles.

[0110] The total amount of compound (pt-4) and compound (pt-4') used is usually 2 moles to 10 moles per mole of compound (pt-2), more preferably 2 moles to 5 moles, and even more preferably 2 moles to 3 moles.

[0111] The amount of solvent used is typically 1 to 1000 parts by mass per 1 part by mass of compound (pt-2).

[0112] The reaction temperature is usually not lower than -100°C and not higher than 300°C.

[0113] In X2 (compound (MA-3)) used in the step (2-i) of Route 2, X is a halogen atom, preferably a chlorine atom or a bromine atom. The compound represented by the formula (pt-6) can be produced by reacting the compound represented by the formula (pt-5) with the compound (MA-3) in a solvent.

[0114] Examples of the compound represented by the formula (pt-5) include dibutyl 3,4-perylenedicarboxylate, N-(2,6-diisopropylphenyl)-3,4-perylenedicarboximide, and the like.

[0115] 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; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid. Methylene chloride and chloroform are more preferred.

[0116] The usage amount of the compound (MA-3) is usually 1 mol or more and 5 mol or less, more preferably 1 mol or more and 2.5 mol or less, and even more preferably 1 mol or more and 1.25 mol or less, relative to 1 mol of the compound represented by the formula (pt-5).

[0117] The usage amount of the solvent is usually 1 to 1000 parts by mass relative to 1 part by mass of the compound represented by the formula (pt-5).

[0118] The reaction temperature is typically between -100°C and 300°C.

[0119] In step (2-ii), the R of the compound represented by formula (pt-8) 1 ~R 4 *-CO-OR 18 The compound represented by (* represents a bond) (hereinafter sometimes referred to as compound (pt-8-1)) and the compound represented by formula (pt-7) (sometimes referred to as compound (pt-7)) are R 18 -OH (compound (MA-4-1)), and / or R 18 -X (compound (MA-4-2)) can be produced by reacting it in a solvent. (MA-4-1) may be used alone or in combination of two or more types, and (MA-4-2) may also be used alone or in combination of two or more types. The R of the compound represented by formula (pt-8) 1 and R 4 , R 2 and R 3 However, independently of each other, together, *-CO-N(R 17 A compound represented by )-CO-* (where * represents a bond) (hereinafter sometimes referred to as compound (pt-8-2)) is a compound (pt-7) and R 17 -NH2 (compound (MA-4-3)) can be produced by reacting it in a solvent.

[0120] Examples of compounds (pt-7) include 4-bromo-1,8-naphthalenedicarboxylic acid anhydride.

[0121] The total amount of compound (MA-4-1) and compound (MA-4-2) used is usually 2 moles to 20 moles, preferably 2 moles to 15 moles, and more preferably 2 moles to 10 moles, per mole of compound (pt-7).

[0122] The amount of compound (MA-4-3) used is usually 1 mole to 10 moles per mole of compound (pt-7), preferably 1 mole to 8 moles, more preferably 1 mole to 6 moles, and even more preferably 1 mole to 4 moles.

[0123] Examples of the aforementioned solvents 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; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole.

[0124] The amount of solvent used is typically 1 to 1000 parts by mass per 1 part by mass of compound (pt-7), whether producing compound (pt-8-1) or compound (pt-8-2).

[0125] The reaction temperature is typically between -100°C and 300°C, whether producing compound (pt-8-1) or compound (pt-8-2).

[0126] The compound (MA-1) used in step (2-iii) is preferably bis(pinacolato)diborone, bis(catecorato)diborone, bis(neopentylglycolato)diborone, pinacolborane, catecorborane, neopentyl glycolborane, or 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneisopropoxyboronic acid pinacol, with bis(pinacolato)diborone and pinacolborane being more preferred. The amount of compound (MA-1) used is usually 1 mole to 100 moles, more preferably 1 mole to 10 moles, and even more preferably 1 mole to 5 moles, per mole of the compound represented by formula (pt-8). It is preferable to carry out the reaction in the presence of a catalyst, a base, and a solvent. [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride and bis(triphenylphosphine)palladium(II) dichloride are preferred catalysts, and potassium acetate, sodium acetate, and potassium phenoxide are preferred bases. The amount of catalyst used is typically 0.01 moles or more and 1 mole or less per mole of the compound represented by formula (pt-8), more preferably 0.01 moles or more and 0.3 moles or less, and even more preferably 0.01 moles or more and 0.15 moles or less. The amount of base used is typically 1 mole to 50 moles, more preferably 1 mole to 20 moles, and even more preferably 1 mole to 10 moles, per mole of the compound represented by formula (pt-8).

[0127] Examples of the aforementioned solvents include 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, tetrahydrofuran, cyclopentyl methyl ether, and 1,4-dioxane; 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; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole, but dimethyl sulfoxide, N,N-dimethylformamide, and cyclopentyl methyl ether are preferred. The amount of solvent used is 1 to 1000 parts by mass relative to the compound represented by formula (pt-8).

[0128] The reaction temperature is typically between -100°C and 300°C.

[0129] The compound represented by formula (pt-10) in step (2-iv) can be produced by reacting the compound represented by formula (pt-6) and the compound represented by formula (pt-9) in a solvent in the presence of a catalyst, a phosphine ligand, and a base.

[0130] Examples of the catalyst include tris(dibenzylideneacetone)dipalladium(0), bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, palladium(II) chloride, sodium tetrachloropalladium(II)ate, 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.

[0131] Examples of the phosphine ligands include monodentate phosphine ligands such as tributylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, tri(o-tolyl)phosphine, tri(m-tolyl)phosphine, tri(p-tolyl)phosphine, tris(3-methoxyphenyl)phosphine, tris[3,5-bis(trifluoromethyl)phenyl]phosphine, ethyldiphenylphosphine, tri(2-furyl)phosphine, tri(2-thienyl)phosphine, tris(2,6-dimethoxyphenyl)phosphine, diphenylpropylphosphine, di-tert-butylphenylphosphine, tris(4-fluorophenyl), tris(4-methoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, triphenylphosphine, 4-(dimethylamino)phenyldiphenylphosphine, and dicyclohexylphenylphosphine, with tri-tert-butylphosphine, tricyclohexylphosphine, and triphenylphosphine being preferred.

[0132] Examples of the aforementioned bases include hydroxides, carbonates, bicarbonates, phosphates, carboxylates, and alkoxides of alkali metals or alkaline earth metals, which are inorganic bases. The base used may be in an anhydrous or hydrated form. Preferably, examples include hydroxides, carbonates, bicarbonates, phosphates, and carboxylates of alkali metals or alkaline earth metals, with alkali metal or alkaline earth metal carbonates and phosphates being more preferred. Preferred alkali metal or alkaline earth metal salts include lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, barium carbonate, lithium phosphate, sodium phosphate, and potassium phosphate, with sodium carbonate, potassium carbonate, and potassium phosphate being more preferred.

[0133] 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 and xylene; 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, carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid, and imidazole. Toluene and xylene are preferred.

[0134] 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, per 1 mol of the compound represented by the formula (pt-6). 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, per 1 mol of the compound represented by the formula (pt-6). The amount of the base used is usually 1 mol or more and 50 mol or less, more preferably 1 mol or more and 25 mol or less, and even more preferably 1 mol or more and 15 mol or less, per 1 mol of the compound represented by the formula (pt-6).

[0135] The total amount of the compound represented by the formula (pt-9) used is usually 1 mol or more and 5 mol or less, more preferably 1 mol or more and 2.5 mol or less, and even more preferably 1 mol or more and 1.5 mol or less, per 1 mol of the compound represented by the formula (pt-6).

[0136] The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the compound represented by the formula (pt-6).

[0137] The reaction temperature is typically between -100°C and 300°C.

[0138] Compound (I) in step (2-v) can be produced by reacting the compound represented by formula (pt-10) in a solvent in the presence of a base.

[0139] Examples of the aforementioned bases include hydroxides, carbonates, bicarbonates, phosphates, carboxylates, and alkoxides of alkali metals or alkaline earth metals, which are inorganic bases. The base used may be in an anhydrous form or a hydrated form. Preferably, alkali metal hydroxides and carbonates are preferred. As alkali metal hydroxides, lithium hydroxide, sodium hydroxide, potassium hydroxide, and cesium hydroxide are preferred, and as alkali metal hydroxides, lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate are more preferred, with potassium carbonate and cesium carbonate being even more preferred.

[0140] Examples of the aforementioned solvents 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, phenol, ethylene glycol, diethylene glycol, and ethanolamine; 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; 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 diethylene glycol and ethanolamine being preferred.

[0141] The amount of base used is typically 1 mole to 200 moles, more preferably 5 moles to 100 moles, and even more preferably 10 moles to 70 moles, per mole of the compound represented by formula (pt-6).

[0142] The amount of solvent used is typically 1 to 1000 parts by mass per 1 part by mass of the compound represented by formula (pt-6).

[0143] The reaction temperature is typically between -100°C and 300°C.

[0144] After the reaction is complete, the method for extracting compound (I) is not particularly limited and can be extracted by various known methods. After extraction, the obtained residue may be purified by column chromatography or recrystallization. The chemical structure of the obtained compound can be analyzed by known analytical methods and conditions. Such analytical methods are not particularly limited, but examples include X-ray crystallography, mass spectrometry (LC), NMR analysis, and elemental analysis. X-ray crystallography can be performed, for example, in accordance with Chemistry of Materials, 2012, Vol. 24, pp. 4647-4652.

[0145] <<Coloring agent (A1)>> The colored resin composition of the present invention may contain, as a colorant (A), a dye other than a terylene compound (hereinafter sometimes referred to as dye (A1-1)) and / or a pigment (hereinafter sometimes referred to as pigment (A1-2)) (hereinafter, dye (A1-1) and pigment (A1-2) together may be referred to as colorant (A1)). These may be used individually or in combination of two or more.

[0146] The dye (A1-1) is not particularly limited as long as it does not contain a terylene compound, and any known dye 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 listed in the Dyeing Notes (Irozome-sha). In addition, based on chemical structure, examples 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.

[0147] The pigment (A1-2) is not particularly limited and any known pigment can be used, as long as it does not contain a terylene compound. Examples include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments classified as pigments include yellow pigments such as CI 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; CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and other orange pigments; CI 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, and other red pigments; CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, and other blue pigments; CI Pigment Violet 1, 19, 23, 32, 36, 38, and other violet color pigments; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; CI Pigment Brown 23, 25, and other brown pigments; Examples include black pigments such as CI Pigment Black 1 and 7.

[0148] As the coloring agent (A1), yellow, red, or green dyes and pigments are preferred.

[0149] The coloring agent (A1) may be subjected to rosin treatment, surface treatment using derivatives into which acidic or basic groups have been introduced, graft treatment of the surface of the coloring agent (A1) with polymer compounds, atomization treatment by sulfuric acid atomization method, washing treatment with organic solvents or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc. The particle size of the coloring agent (A1) is preferably substantially uniform.

[0150] When colorant (A) further contains colorant (A1), the lower limit of the total amount of terylene compounds in colorant (A) is, for example, 1% by mass or more, preferably 2% by mass or more, more preferably 10% by mass or more, even more preferably 25% by mass or more, and particularly preferably 50% by mass or more, relative to the total amount of colorant (A). On the other hand, when colorant (A) further contains colorant (A1), the upper limit of the total amount of terylene compounds in colorant (A) is, for example, less than 100% by mass, relative to the total amount of colorant (A).

[0151] If the colored resin composition contains a solvent (E), a colorant-containing liquid (sometimes referred to as a colored composition) containing the colorant (A) and solvent (E) may be prepared in advance, and then the colored resin composition may be prepared using the colorant-containing liquid. If the colorant (A) does not dissolve in the solvent (E), for example, if the colorant (A) contains pigments (A1-2), the colorant-containing liquid can be prepared by dispersing the colorant (A) in the solvent (E) and mixing it. The colorant-containing liquid may contain some or all of the solvent (E) contained in the colored resin composition.

[0152] The solid content in the coloring agent-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, even 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, relative to the total amount of the coloring agent-containing liquid.

[0153] The coloring agent (A) can be uniformly dispersed in solution by dispersing it with a dispersant. When using two or more coloring agents (A) in combination, each may be dispersed individually, or multiple types may be mixed and dispersed together.

[0154] Examples of dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specifically, examples include polyester-based, polyamine-based, and acrylic-based 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.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers® (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA® (registered trademark) (manufactured by BASF Ltd.), Azisper® (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), and Disperbyk® (registered trademark) (manufactured by BIC Chemie Co., Ltd.), BYK® (registered trademark) (manufactured by BIC Chemie Co., Ltd.). A resin (B) described later may also be used as a dispersant.

[0155] When a dispersant is used, the amount of dispersant (solid content) used is usually 1 to 10,000 parts by mass, preferably 5 to 5,000 parts by mass, more preferably 10 to 1,000 parts by mass, and even more preferably 15 to 800 parts by mass, per 100 parts by mass of colorant (A). When the amount of dispersant used is within the above range, a colorant-containing liquid with a more uniform dispersion state tends to be obtained.

[0156] The content of the coloring agent (A) is preferably 0.1% to 50% by mass, more preferably 0.5% to 40% by mass, and even more preferably 1% to 30% by mass, relative to the total amount of solids in the colored resin composition. When the content of the coloring agent (A) is within the above range, the color density when used as a color filter is sufficient, and the required amount of resin (B) can be included in the composition, so it is preferable that a pattern with sufficient mechanical strength can be formed. Herein, "total amount of solids" as used herein refers to the amount obtained by subtracting the solvent content from the total amount of the colored resin composition. The total amount of solids and the content of each component therein can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0157] <Resin (B)> Unlike thermoplastic resins, resin (B) is not particularly limited as long as it is used for forming photoresists, but it is preferably an alkali-soluble resin, and preferably an alkali-soluble resin containing a carboxylic acid.

[0158] Examples of resin (B) include the following resins [K1] to [K6]. Resin [K1]; a copolymer having structural units derived from at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "(a)") and structural units derived from a monomer (b) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)"); Resin [K2]; a copolymer having structural units derived from (a) and structural units derived from (b) and a monomer (c) copolymerizable with (a) (however different from (a) and (b)) (hereinafter sometimes referred to as "(c)"); Resin [K3]; a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]; a copolymer having structural units derived from (a) to which (b) is added and structural units derived from (c); Resin [K5]; a copolymer having structural units derived from (b) to which (a) is added and structural units derived from (c); A copolymer having a structural unit obtained by adding (a) to a resin [K6] and further adding a carboxylic acid anhydride, and a structural unit obtained by adding (c).

[0159] Examples of monomers (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, 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 carboxyl groups, 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, excluding fumaric acid and mesaconic acid; Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate; Examples include unsaturated acrylates containing both a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Of these, acrylic acid, methacrylic acid, and maleic anhydride are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions. In this specification, "(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.

[0160] Monomer (b) refers to a polymerizable compound having a cyclic ether structure with 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. Preferably, monomer (b) is a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0161] Examples of monomer (b) include monomers having an oxyranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b1)"), monomers having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b2)"), and monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b3)").

[0162] Examples of monomers (b1) include monomers having a structure in which unsaturated aliphatic hydrocarbons are epoxidized (hereinafter sometimes referred to as "monomer (b1-1)") and monomers having a structure in which unsaturated alicyclic hydrocarbons are epoxidized (hereinafter sometimes referred to as "monomer (b1-2)").

[0163] As monomer (b1-1), monomers having a glycidyl group and an ethylenically unsaturated bond are preferred. Specifically as monomer (b1-1), glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis( Examples include 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, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0164] Examples of monomers (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide® 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer® A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer® M100; manufactured by Daicel Corporation), compounds represented by formula (BI), and compounds represented by formula (BII).

[0165] [ka]

[0166] [In formulas (BI) and (BII), R a and R bEach of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group. X a and X b These are independent of each other, single bonds, *-R c -, *-R c -O-, *-R c -S- or *-R c Represents -NH- R c This represents an alkanediyl group with 1 to 6 carbon atoms. * represents a bond with O.

[0167] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl groups.

[0168] Examples of alkyl groups in which a hydrogen atom is substituted with hydroxyl include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, and 4-hydroxybutyl group.

[0169] R a and R b Preferably, the group can be 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.

[0170] 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.

[0171] X a and X bPreferably, the bonds include single bonds, methylene groups, ethylene groups, *-CH2-O- (* represents a bond with O) groups, and *-CH2CH2-O- groups, and more preferably, single bonds and *-CH2CH2-O- groups (* represents a bond with O).

[0172] Compounds represented by formula (BI) include those represented by any of formulas (BI-1) to (BI-15). Among these, 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.

[0173] [ka]

[0174] Compounds represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15), among which 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.

[0175] [ka]

[0176] The compound represented by formula (BI) and the compound represented by formula (BII) may be used individually, or the compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When 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 on a molar basis, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

[0177] 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 preferred. Examples of monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyl oxetane, 3-ethyl-3-(meth)acryloyloxymethyl oxetane, 3-methyl-3-(meth)acryloyloxyethyl oxetane, and 3-ethyl-3-(meth)acryloyloxyethyl oxetane.

[0178] 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 preferred. Examples of monomer (b3) include tetrahydrofuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofuryl methacrylate.

[0179] Examples of monomers (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 ] Decane-8-yl(meth)acrylate (in the relevant technical field, it is commonly called "dicyclopentanyl(meth)acrylate". It is also sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 Decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] Decen-8-yl(meth)acrylate (commonly known as "dicyclopentenyl(meth)acrylate" in the relevant art), tricyclo[5.2.1.02,6 (meth)acrylic acid esters such as 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-methoxybic Chlo[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 Bicyclounsaturated compounds such as -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, 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; Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl)maleimide; Examples include vinyl group-containing aromatic compounds such as 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, styrene, vinyltoluene, and tricyclotoluene were selected based on their copolymerization reactivity and heat resistance. [5.2.1.0 2,6 Decane-8-yl(meth)acrylate, tricyclo[5.2.1.0 2,6 Decane-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]hepto-2-ene, and benzyl (meth)acrylate are preferred.

[0180] In resin [K1], the ratio of structural units derived from each is, among all structural units constituting resin [K1], (a) Structural units derived from (a); 2-60 mol% (b) Structural units derived from (b); 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (b) Structural units derived from (b); 50-90 mol% It is preferable that it be so. When the ratio of structural units of resin [K1] falls 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 resulting optical filter tend to be excellent.

[0181] The resin [K1] can be manufactured, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited literature.

[0182] Specifically, a method involves placing predetermined amounts of (a) and (b), a polymerization initiator, and a solvent into a reaction vessel, creating a deoxygenated atmosphere by, for example, replacing oxygen with nitrogen, and heating and maintaining the temperature while stirring. The polymerization initiator and solvent used here are not particularly limited and can be those commonly used in the field. For example, examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and the solvent can be any solvent that dissolves each monomer. Examples of solvents include the solvent (E) of the colored resin composition of the present invention, as described later.

[0183] The resulting copolymer may be used as is after the reaction, or after being concentrated or diluted, or after being extracted as a solid (powder) by methods such as reprecipitation. In particular, by using the solvent contained in the colored resin composition of the present invention as the solvent during polymerization, the solution after the reaction can be used directly in the preparation of the colored resin composition of the present invention, thereby simplifying the manufacturing process of the colored resin composition of the present invention.

[0184] In resin [K2], the ratio of structural units derived from each is, among all structural units constituting resin [K2], (a) Structural units derived from (a); 2-45 mol% (b) Structural units derived from (b); 2-95 mol% (c) Structural units derived from (c); 1-65 mol% It is preferable that this be the case. (a) Structural units derived from (a); 5-40 mol% (b) Structural units derived from (b); 5-80 mol% (c) Structural units derived from (c); 5-60 mol% It is preferable that it be so. When the ratio of structural units of resin [K2] is within the above range, the colored resin composition tends to have excellent storage stability, developability when forming colored patterns, and solvent resistance, heat resistance, and mechanical strength of the resulting optical filter.

[0185] Resin [K2] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0186] In resin [K3], the ratio of structural units derived from each is, out of the total structural units constituting resin [K3], (a) Structural units derived from (a); 2-60 mol% (c) Structural units derived from this structure; 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (c) Structural units derived from (c); 50-90 mol% It is preferable that it be so. Resin [K3] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0187] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding the cyclic ether having 2 to 4 carbon atoms of (b) to the carboxylic acid and / or carboxylic acid anhydride of (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, it is preferable that the ratio of structural units derived from each is the same as that given for resin [K3].

[0188] Next, a portion 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 that (b) possesses. Following the production of the copolymer of (a) and (c), the atmosphere inside the flask is replaced from nitrogen to air, and (b), a reaction catalyst for the reaction between a carboxylic acid or carboxylic acid anhydride and a cyclic ether (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone) are added to the flask and the mixture is reacted at, for example, 60 to 130°C for 1 to 10 hours to produce resin [K4]. The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). This range tends to result in a good balance of storage stability of the colored resin composition, developability when forming patterns, and solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting patterns. Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K4], and (b1-1) is even more preferred. 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 preparation method, reaction temperature, and time, can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization. Similarly, the preparation method and reaction temperature can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization.

[0189] As a first step, resin [K5] is produced in the same manner as the production method for resin [K1] described above to obtain a copolymer of (b) and (c). As described above, the obtained copolymer may be used as is after the reaction, or a concentrated or diluted solution may be used, or it may be used after being extracted as a solid (powder) by methods such as reprecipitation. The ratios of structural units derived from (b) and (c) are, in relation to the total number of moles of all structural units constituting the copolymer, respectively: (b) Structural units derived from (b); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. (b) Structural units derived from (b); 10-90 mol% (c) Structural units derived from (c); 10-90 mol% It is preferable that it be so.

[0190] Furthermore, resin [K5] can be obtained by reacting the cyclic ether derived from (b) in the copolymer of (b) and (c) with the carboxylic acid or carboxylic acid anhydride of (a) under the same conditions as for the production of resin [K4]. The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K5], and (b1-1) is even more preferred.

[0191] 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 carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of carboxylic acid anhydrides 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, and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride. The amount of carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of (a).

[0192] Specific resins (B) include 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.02,6 Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyl oxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, tricyclodecyl Examples of resins include those obtained by adding glycidyl(meth)acrylate to a (meth)acrylate / benzyl(meth)acrylate / (meth)acrylic acid copolymer [K4]; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / glycidyl(meth)acrylate, resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / styrene / glycidyl(meth)acrylate [K5]; and resins obtained by reacting tetrahydrophthalic anhydride with a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / glycidyl(meth)acrylate [K6].

[0193] The resin (B) is more preferably resin [K1] and resin [K2], and is particularly preferably resin [K1].

[0194] The weight-average molecular weight (Mw) of resin (B) in terms of polystyrene is preferably 1,000 to 100,000, more preferably 2,000 to 50,000, and even more preferably 3,000 to 30,000. When the weight-average molecular weight is within the above range, the solubility of the unexposed areas in the developer is high, and the residual film rate and hardness of the resulting pattern tend to be high. The degree of dispersion of 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.

[0195] The acid value (solid content equivalent) of resin (B) is preferably 10 mg-KOH / g or more and 300 mg-KOH / g or less, more preferably 20 mg-KOH / g or more and 250 mg-KOH / g or less, even more preferably 25 mg-KOH / g or more and 200 mg-KOH / g or less, even more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, and particularly preferably 60 mg-KOH / g or more and 135 mg-KOH / g or less. Here, the acid value is measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0196] 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 solubility of the unexposed areas in the developer tends to be high.

[0197] <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). Examples include compounds having polymerizable ethylenically unsaturated bonds, and preferably (meth)acrylic acid ester compounds.

[0198] 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 monomers (a), (b), and (c) mentioned above.

[0199] 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.

[0200] In particular, 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, and Examples 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, with dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate being preferred.

[0201] The weight-average molecular weight of the polymerizable compound (C) is preferably 50 to 4,000, more preferably 70 to 3,500, even more preferably 100 to 3,000, even more preferably 150 to 2,900, and particularly preferably 250 to 1,500.

[0202] The content of 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.

[0203] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc., upon the action of light or heat and can initiate polymerization; any known polymerization initiator can be used.

[0204] Examples of polymerization initiators (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0205] 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-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1-[ Examples include 9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine. Furthermore, commercially available O-acyloxime compounds such as Irgacure® OXE01, OXE02 (both manufactured by BASF) and N-1919 (manufactured by ADEKA Corporation) may be used. Among these, 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-cyclopentylpropane-1-one-2-imine is preferred as the O-acyloxime compound, with N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine being more preferred.

[0206] Examples of alkylphenone compounds 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. Commercial alkylphenone compounds such as Irgacure® 369, 907, and 379 (all manufactured by BASF) may also be used. Examples of alkylphenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyldimethyl ketal.

[0207] 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, Japanese Patent Publication No. 6-75372, Japanese Patent Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2-chloro Examples include phenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group (see, for example, Japanese Patent Application Publication No. 7-10913, etc.).

[0208] Examples of 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, and 2,4-bis(trichloromethyl)-6-[2-( Examples include 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.

[0209] Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure® 819 (manufactured by BASF) may also be used.

[0210] Furthermore, examples of polymerization initiators (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, o-benzoyl methyl benzoate, 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; and 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with polymerization initiators (D1) (especially amines) as described later.

[0211] The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds, and more preferably a polymerization initiator comprising an O-acyloxime compound.

[0212] The content of the polymerization initiator (D) is preferably 0.1 parts by mass to 30 parts by mass, and more preferably 1 part by mass to 20 parts by mass, based on 100 parts by mass of the total amount of the total resin (B) and polymerizable compound (C) contained in the colored resin composition. When the content of the polymerization initiator (D) is within the above range, sensitivity tends to increase and exposure time is shortened, thus improving the productivity of color filters.

[0213] <Polymerization initiator (D1)> A polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound (C) whose polymerization has been initiated by a polymerization initiator (D). When a polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

[0214] Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0215] Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michla's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being preferred. Alternatively, commercially available amine compounds such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

[0216] 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.

[0217] Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0218] 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.

[0219] When these polymerization initiators (D1) are used, their content 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, based on 100 parts by mass of the total amount of the total resin (B) and polymerizable compound (C) contained in the colored resin composition.

[0220] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the art may be used. Examples of solvent (E) include ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents containing both -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, and -COO- in the molecule), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxides, etc. Two or more of these solvents may be used in combination.

[0221] 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.

[0222] Examples of 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, phenethole, and methylanisole.

[0223] Examples of 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-ethoxy-2-methylpropionate Examples 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.

[0224] Examples of 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.

[0225] Examples of alcoholic solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0226] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0227] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0228] Preferred solvents (E) include propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and cyclohexanone.

[0229] When solvent (E) is present, the solvent (E) content is usually 99.99% by mass or less, preferably 40% to 99% by mass, more preferably 50% to 95% by mass, even more preferably 70% to 95% by mass, and even more preferably 75% to 90% by mass, relative to 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% to 60% by mass, more preferably 5% to 50% by mass, even more preferably 5% to 30% by mass, and even more preferably 10% to 25% by mass. When the solvent (E) content is within the above range, the flatness during coating tends to be good, and the display characteristics tend to be good because there is no shortage of color density when a color filter is formed.

[0230] <Leveling agent (F)> Examples of leveling agents (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants containing fluorine atoms. These may have polymerizable groups in their side chains.

[0231] Examples of silicone-based surfactants include surfactants that have siloxane bonds in their molecules. Specifically, examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, 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).

[0232] Examples of fluorine-based surfactants include surfactants having fluorocarbon chains in their molecules. Specifically, these include Florard® FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac® F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top® EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon® S381, S382, SC101, SC105 (manufactured by AGC Inc.), and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

[0233] Examples of silicone-based surfactants containing fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in their molecules. Specifically, examples include Megafac® R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0234] When a leveling agent (F) is included, 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, relative to the total amount of the colored resin composition. This content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0235] <Other ingredients> The colored resin composition may optionally contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, and chain transfer agents.

[0236] <Method for producing colored resin composition> Colored resin compositions can be prepared by mixing a colorant (A), a resin (B), a polymerizable compound (C) used as needed, a polymerization initiator (D), a solvent (E), a leveling agent (F), and other components. Mixing can be carried out using known or conventional equipment and conditions. The coloring agent (A) may be used in a dispersed state after being mixed with 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. It is preferable to use it in a dispersed state. In this case, part or all of the dispersant and resin (B) may be added as needed. Alternatively, the coloring agent (A) may be used after being dissolved in part or all of the solvent (E) in advance. The desired colored resin composition can be prepared by mixing the remaining components to the coloring agent-containing liquid obtained in this way to a predetermined concentration.

[0237] <How to manufacture color filters> A color filter, which may also be a color conversion layer, can be formed from a colored resin composition. Methods for forming a colored pattern include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. Photolithography is a method in which the colored resin composition is applied to a substrate, dried to form a colored resin composition layer, and then exposed to light through a photomask for development. In photolithography, by not using a photomask during exposure and / or by not developing, a colored coating film, which is a cured product of the colored resin composition layer, can be formed. The colored pattern or colored coating film formed in this way is the color filter of the present invention.

[0238] The film thickness of the color filter to be manufactured is not particularly limited and can be adjusted as appropriate depending on the purpose and application. For example, it is 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and more preferably 0.5 μm or more and 6 μm or less.

[0239] As substrates, glass plates such as quartz glass, borosilicate glass, aluminasilate glass, and soda-lime glass with a silica coating on the surface are used; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate are used; silicon is used; and aluminum, silver, silver / copper / palladium alloy thin films are formed on the substrate. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates.

[0240] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be manufactured as follows. First, a colored resin composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying, and then dried to obtain a smooth colored resin composition layer. Coating methods include spin coating, slit coating, and slit and spin coating. When performing heat drying, the temperature is preferably between 30°C and 120°C, and more preferably between 50°C and 110°C. The heating time is preferably between 10 seconds and 60 minutes, and more preferably between 30 seconds and 30 minutes. When performing vacuum drying, it is preferable to do so under a pressure of 50 Pa to 150 Pa and at a temperature range of 20°C to 25°C. The thickness of the colored resin composition layer is not particularly limited and can be appropriately selected according to the desired thickness of the color filter.

[0241] Next, the colored resin composition layer is exposed via a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate to the intended application is used. Furthermore, it is preferable to use an exposure apparatus such as a mask aligner and a stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light rays and precise alignment between the photomask and the substrate on which the colored resin composition layer is formed.

[0242] For exposure, a light source that generates light with a wavelength between 250 nm and 450 nm is preferred. For example, light below 350 nm can be filtered out using a filter that cuts out this wavelength range, or light around 436 nm, 408 nm, and 365 nm can 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.

[0243] A colored pattern is formed on the substrate by developing the colored resin composition layer after exposure by contacting it with a developer. During development, the unexposed parts of the colored resin composition layer are dissolved and removed by the developer. As the developer, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, and more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may also contain a surfactant. The development method can be any of the following: paddle method, dipping method, or spray method. Furthermore, the substrate may be tilted to any angle during development. It is preferable to wash the substrate with water after development.

[0244] Furthermore, it is preferable to perform post-baking on the obtained coloring pattern. The post-baking temperature is preferably 150°C to 250°C, and more preferably 160°C to 240°C. The post-baking time is preferably 1 minute to 120 minutes, and more preferably 10 minutes to 60 minutes.

[0245] <Display device> The aforementioned color filter is useful as a color filter for display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors, and is particularly useful as a color filter for organic EL devices. [Examples]

[0246] The present invention will be described in more detail below with reference to examples, but the present invention is not limited by the following examples, and it is certainly possible to implement it with appropriate modifications within the scope that is consistent with the spirit of the preceding and following descriptions, and all such modifications are included within the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "percent mass".

[0247] In the following examples, the structure of the compounds was confirmed by mass spectrometry (LC; Agilent 1200, MASS; Agilent LC / MSD6130) and NMR (Varian 400-MR).

[0248] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin, calculated on a polystyrene basis, were measured using the GPC method under the following conditions. Equipment: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: Tetrahydrofuran Flow rate: 1.0mL / min Solid content concentration of the analytical sample: 0.001~0.01% by mass Injection volume: 50μL Detector: RI Calibration standards: 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 to the number-average molecular weight (Mw / Mn) obtained above in polystyrene terms was defined as the degree of dispersion.

[0249] Synthesis Example 1 <Preparation of compound (A)> 5.4 parts of naphthalene-1,4,5,8-tetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), potassium hydroxide (manufactured by Kanto Chemical Co., Ltd.), and 104 parts of water were mixed and heated to 85°C. 8.0 parts of bromine (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added dropwise over 1 hour, and the mixture was stirred for 3 hours. After cooling to 10°C, 11 parts of concentrated hydrochloric acid were added dropwise, and a white precipitate was formed. The mixture containing this white precipitate was filtered, and the residue after filtration was washed with 50 parts of water and 20 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 6.8 parts of the compound represented by formula (A) (compound (A) 4,5-dibromonaphthalene-1,8-dicarboxylic dianhydride) (yield 95%).

[0250] [ka]

[0251] Synthesis Example 2 <Preparation of compound (B)> 2.5 parts of compound (A) obtained in Synthesis Example 1, 5.0 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industries, Ltd.), 15 parts of 1-methyl-2-pyrrolidone (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 15 parts of propionic acid (manufactured by Tokyo Chemical Industries, Ltd.) were mixed and stirred at 160°C for 12 hours. After cooling to 10°C, 100 parts of water were added dropwise, and a light brown precipitate was formed. The mixture containing this light brown precipitate was filtered, and the residue after filtration was washed with 50 parts of water and 10 parts of methanol. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 2.0 parts of compound (compound (B)) represented by formula (B) (yield 55%).

[0252] [ka]

[0253] <Identification of compound (B)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 514 Exact Mass: 513

[0254] Synthesis Example 3 <Preparation of compound (C)> 25 parts of compound (A) obtained in Synthesis Example 1, 58 parts of 1-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.1 parts of potassium iodide (manufactured by Kanto Chemical Co., Ltd.), 20 parts of potassium hydroxide (manufactured by Kanto Chemical Co., Ltd.), 5.7 parts of methyltri-n-octylammonium chloride (manufactured by Tokyo Chemical Industry Co., Ltd.), and 935 parts of water were mixed and stirred at 85°C for 12 hours. After cooling to 20°C, 900 parts of chloroform were added, and the chloroform layer was extracted and concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 22 parts of compound (compound (C)) represented by formula (C) (yield 65%).

[0255] [ka]

[0256] <Identification of compound (C)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 485 Exact Mass: 484

[0257] Synthesis Example 4 <Preparation of compound (D)> 5.0 parts of 1,8-dibromonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), 11 parts of bis(pinacolato)diborone (manufactured by Tokyo Chemical Industry Co., Ltd.), 10 parts of potassium acetate (manufactured by Kanto Chemical Co., Ltd.), 1.3 parts of 1,1-bis(diphenylphosphino)ferrocenedichloropalladium(II) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 95 parts of dehydrated N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 90°C for 17 hours. The resulting mixture was filtered through Celite and the filtrate was concentrated. The residue was washed with 18 parts of methanol. The resulting residue was dried under reduced pressure at 60°C to obtain 5.6 parts of the compound represented by formula (D) (compound (D)) (yield 85%).

[0258] [ka]

[0259] <Identification of compound (D)> 1 H NMR (400MHz, CDCl3, 25℃) δ 1.42(s,24H),7.51(dd,2H),8.02(s,2H),8.75(dd,2H).

[0260] Synthesis Example 5 <Preparation of compound (E)> Except for substituting 58 parts of 1-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.) with 46 parts of bromoethane (manufactured by Tokyo Chemical Industry Co., Ltd.), 17 parts of the compound represented by formula (E) (compound (E)) were obtained in the same manner as in Synthesis Example 3 (yield 55%).

[0261] [ka]

[0262] <Identification of compound (E)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 429 Exact Mass: 428

[0263] Synthesis Example 6 <Preparation of compound (F)> Except for substituting 58 parts of 1-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.) with 81 parts of 1-bromo-2-ethylhexane (manufactured by Tokyo Chemical Industry Co., Ltd.), 28 parts of the compound represented by formula (F) (compound (F)) were obtained in the same manner as in Synthesis Example 3 (yield 81%).

[0264] [ka]

[0265] <Identification of compound (F)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 597 Exact Mass: 596

[0266] Synthesis Example 7 <Preparation of compound (G)> Except for substituting 58 parts of 1-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.) with 81 parts of 1-bromooctane (manufactured by Tokyo Chemical Industry Co., Ltd.), 24 parts of the compound represented by formula (G) (compound (G)) were obtained in the same manner as in Synthesis Example 3 (yield 69%).

[0267] [ka]

[0268] <Identification of compound (G)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 597 Exact Mass: 596

[0269] Synthesis Example 8 <Preparation of compound (H)> Except for substituting 58 parts of 1-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.) with 58 parts of 2-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.), 7.5 parts of the compound represented by formula (H) (compound (H)) were obtained in the same manner as in Synthesis Example 3 (yield 21%).

[0270] [ka]

[0271] <Identification of compound (H)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 485 Exact Mass: 484

[0272] Synthesis Example 9 <Preparation of compound (I-1)> Twelve parts of compound (B) obtained in Synthesis Example 2, three parts of compound (D) obtained in Synthesis Example 4, 0.18 parts of tris(dibenzylideneacetone)dipalladium(0) (manufactured by Tokyo Chemical Industries, Ltd.), 0.22 parts of tricyclohexylphosphine (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 14 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 528 parts of dehydrated xylene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 145°C for 18 hours. After cooling to 20°C, 300 parts of methanol were added dropwise, and a blue precipitate was formed. The mixture containing this blue precipitate was filtered, and the residue after filtering was washed with 100 parts of methanol. When dried under reduced pressure at 60°C, 2.8 parts of the compound represented by formula (I-1) (compound (I-1)) were obtained (yield 42%).

[0273] [ka]

[0274] <Identification of compound (I-1)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 835 Exact Mass: 834

[0275] Synthesis Example 10 <Preparation of compound (I-2)> 14 parts of compound (C) obtained in Synthesis Example 3, 5.0 parts of compound (D) obtained in Synthesis Example 4, 2.4 parts of tris(dibenzylideneacetone)dipalladium(0) (manufactured by Tokyo Chemical Industries, Ltd.), 3.0 parts of tricyclohexylphosphine (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 22 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 365 parts of dehydrated xylene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 145°C for 18 hours. After cooling to 20°C, the mixture was filtered by Celite and the filtrate was concentrated. The resulting residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 4.2 parts of the compound represented by formula (I-2) (compound (I-2)) (yield 41%).

[0276] [ka]

[0277] <Identification of compound (I-2)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 777 Exact Mass: 776

[0278] Synthesis Example 11 <Preparation of compound (I-3)> Thirty parts of compound (I-2) obtained in Synthesis Example 10, seventy parts of 7-tridecylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), and five hundred parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and stirred at 170°C for 16 hours. After cooling to 100°C, 30 parts of 1N hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 30 parts of ethanol were added dropwise, and a blue precipitate was formed. The mixture containing this blue precipitate was filtered, and the residue after filtering was washed with 30 parts of ethanol. When dried under reduced pressure at 60°C, 22 parts of the compound represented by formula (I-3) (compound (I-3)) were obtained (yield 60%).

[0279] [ka]

[0280] <Identification of compound (I-3)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 880 Exact Mass: 879

[0281] Synthesis Example 12 <Preparation of compound (I-4)> Except for replacing 14 parts of compound (C) with 22 parts of compound (E) obtained in Synthesis Example 5, the procedure was the same as in Synthesis Example 10, and 6.6 parts of the compound represented by formula (I-4) (compound (I-4)) were obtained (yield 75%).

[0282] [ka]

[0283] <Identification of compound (I-4)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 665 Exact Mass: 664

[0284] Synthesis Example 13 <Preparation of Compound (I-5)> Except for replacing 14 parts of compound (C) with 31 parts of compound (F) obtained in Synthesis Example 6, 8.7 parts of the compound represented by formula (I-5) (compound (I-5)) were obtained in the same manner as in Synthesis Example 10 (yield 66%).

[0285] [ka]

[0286] <Identification of Compound (I-5)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H]+ 1002 Exact Mass: 1001

[0287] Synthesis Example 14 <Preparation of compound (I-6)> Eleven parts of the compound represented by formula (I-6) (compound (I-6)) were obtained in the same manner as in Synthesis Example 10, except that 14 parts of compound (C) were replaced with 14 parts of compound (G) obtained in Synthesis Example 7 (yield 80%).

[0288] [ka]

[0289] <Identification of compound (I-6)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 1002 Exact Mass: 1001

[0290] Synthesis Example 15 <Preparation of Compound (I-7)> Except for replacing 14 parts of compound (C) with 16 parts of compound (H) obtained in Synthesis Example 8, 4.0 parts of the compound represented by formula (I-7) (compound (I-7)) were obtained in the same manner as in Synthesis Example 10 (yield 39%).

[0291] [ka]

[0292] <Identification of Compound (I-7)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 777 Exact Mass: 776

[0293] Synthesis Example 16 <Preparation of Compound (I-8)> 8.3 parts of compound (I-1) obtained in Synthesis Example 9 were mixed with 750 parts of chloroform, and 8.0 parts of bromine (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added. The mixture was stirred under reflux for 12 hours. After cooling to 0°C, the reaction mixture was concentrated, and 150 parts of methanol were added dropwise, resulting in the formation of a blue precipitate. When dried under reduced pressure at 60°C, 9.0 parts of the compound represented by formula (I-8) (compound (I-8)) were obtained (yield 75%).

[0294] [ka]

[0295] <Identification of compound (I-8)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 1147 Exact Mass: 1146

[0296] Synthesis Example 17 <Preparation of Compound (I-9)> 3.0 parts of compound (I-8) obtained in Synthesis Example 16, 3.4 parts of tert-octylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.3 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 500 parts of N-methylpyrrolidone (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 80°C for 8 hours. After cooling to 20°C, 1000 parts of 2N hydrochloric acid were added dropwise, and a blue precipitate was formed. The mixture containing this blue precipitate was filtered, and the residue after filtering was washed with 200 parts of methanol. When dried under reduced pressure at 60°C, 3.7 parts of the compound represented by formula (I-9) (compound (I-9)) were obtained (yield 86%).

[0297] [ka]

[0298] <Identification of Compound (I-9)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 1652 Exact Mass: 1651

[0299] Lumogen® F Orange240 (a compound represented by the following formula) was obtained from Tokyo Chemical Industry Co., Ltd.

[0300] [ka]

[0301] Synthesis Example 18 A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, dropping funnel, and stirrer to replace the atmosphere with nitrogen. 280 parts of propylene glycol monomethyl ether acetate were added and heated to 80°C while stirring. Then, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixture of 289 parts of decane-9-yl acrylate (with a molar ratio of 1:1) 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 addition was complete, the mixture was held at 80°C for 4 hours, then cooled to room temperature to obtain a copolymer (resin B1) solution with a solid content of 35.1% and a viscosity of 125 mPa·s measured with a B-type viscometer (23°C). The weight-average molecular weight Mw of the resulting copolymer was 9.2 × 10⁻⁶. 3 The dispersion was 2.08, and the acid value on a solid content basis was 77 mg-KOH / g. Resin B1 has the following structural units.

[0302] [ka]

[0303] Example 1 (1) Preparation of colored resin composition 1 The following components were mixed in the following proportions to obtain colored resin composition 1. (A) Coloring agent: 2.6 parts of the compound represented by formula (I-1) (B) Resin: 54 parts of resin B1 solution (E) Solvent: Propylene glycol monomethyl ether acetate 420 parts

[0304] (2) Preparation of colored resin composition 1' Next, the components were mixed in the following proportions to obtain colored resin composition 1'. Colored resin composition 1 478 parts (C) Polymerizable compound: Dipentaerythritol hexaacrylate (Kayalad® DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 copies (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure® 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

[0305] Example 2 Colored resin composition 2 was prepared in the same manner as in Example 1, except that the compound represented by formula (I-2) was used instead of the compound represented by formula (I-1) in Example 1. Further operations in the same manner as in Example 1 were performed to obtain colored resin composition 2'.

[0306] Comparative Example 1 A colored resin composition H was prepared in the same manner as in Example 1, except that Lumogen® F Orange240 was used instead of the compound represented by formula (I-1) in Example 1. Further, the same procedure as in Example 1 was performed to obtain a colored resin composition H'.

[0307] (2) Preparation of colored coating film (color filter) A colored resin composition was applied to a 5cm square glass substrate (Eagle XG; Corning Corporation) by spin coating to a post-baking thickness of 2μm. The substrate was 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 exposed to an air atmosphere at 80mJ / cm² using an exposure unit (TME-150RSK; Topcon Corporation).2 The sample was irradiated with light at the specified exposure level (based on 365 nm). After light irradiation, post-baking was performed in an oven at 230°C for 30 minutes to obtain a colored coating.

[0308] The chromaticity of the colored coating 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 Y in the CIE XYZ color system using the characteristic function of the C light source.

[0309] (3) Heat resistance test The obtained colored coating was heated in an oven under atmospheric conditions at 230°C for 120 minutes. The color difference ΔE*ab was calculated from the x,y chromaticity coordinates (x, y) and Y measurement values ​​before and after the test using the method described in JIS Z 8730:2009 (7. Method for calculating color difference). * A smaller value of ab indicates less color change, and if ΔE*ab is 5 or less, the colored coating can be considered practically acceptable as a color filter. Furthermore, if the colored coating has good heat resistance, it can be said that a colored pattern made from the same colored resin composition will also have good heat resistance. The results are shown in Table 34.

[0310] (4) Lightfastness test A UV-cut filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Corporation; cuts light below 380 nm) was placed on the obtained colored coating, and the sample was irradiated with xenon lamp light for 48 hours using a lightfastness tester (SUNTEST CPS+: manufactured by Toyo Seiki Co., Ltd.). The color difference ΔE*ab was calculated from the xy chromaticity coordinates (x, y) and Y measurement values ​​before and after the test using the method described in JIS Z 8730:2009 (7. Method for calculating color difference). Color difference ΔE * A smaller value of ab indicates less color change, and if ΔE*ab is 5 or less, the coating can be considered practically acceptable as a color filter. Furthermore, if the colored coating has good lightfastness, it can be said that a colored pattern made from the same colored resin composition will also have good lightfastness. The results are shown in Table 34.

[0311] [Table 34]

[0312] Except for using the compound represented by formula (I-3), formula (I-4), formula (I-5), formula (I-6), formula (I-7), formula (I-8), or formula (I-9) instead of the compound represented by formula (I-1), the colored coating film obtained from the colored resin composition prepared in the same manner as in Example 1 will all exhibit excellent heat resistance and light resistance, similar to Example 1.

Claims

1. It contains a coloring agent and an alkali-soluble resin, and the coloring agent contains a terylene compound having a structure in which eight or more rings are condensed. The terylene compound is a compound represented by formula (I), A colored resin composition in which the compound represented by formula (I) is one or more selected from the group consisting of the compound represented by formula (I-A), the compound represented by formula (I-B), and the compound represented by formula (I-C). 【Chemistry 1】 [In formula (I), R 1 ~R 4 are each independently —CO—O—R 18 (wherein R 18 represents a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and the methylene groups contained in the hydrocarbon group may be replaced by —O—, —CO— or —N(R 17 )).) or both the combination of R 1 and R 4 and the combination of R 2 and R 3 are each independently taken together as *—CO—N(R 17 )—CO—* (wherein * represents a bond to R 1 and R 4 or R 2 and R 3 ).) R 5 ~R 16 Each of these independently represents a C1-C20 hydrocarbon group, a hydrogen atom, a halogen atom, a hydroxyl group, a carboxyl group, or a nitro group, which may have substituents, and the methylene group contained in the hydrocarbon group is -O-, -CO-, or -N(R 17 ) - may be replaced with this. R 17 R represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. 17 If multiple instances exist, they may be identical or different from one another. 【Chemistry 2】 [In formula (I-A), R5 to R16 independently represent a C1 to C20 hydrocarbon group which may have substituents, a hydrogen atom, a halogen atom, a hydroxyl group, a carboxyl group, or a nitro group, and the methylene group contained in the hydrocarbon group may be replaced with -O-, -CO-, or -N(R17)-. R 17 represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. If there are multiple R 17 groups, they may be the same or different from one another. R 18a to R 18d independently represent a hydrocarbon group having 1 to 18 carbon atoms, which may have substituents, and the methylene group contained in the hydrocarbon group may be replaced with -O-, -CO-, or -N(R 17)-. 【Transformation 3】 [In formula (I-B), R5 to R16 independently represent a C1 to C20 hydrocarbon group which may have substituents, a hydrogen atom, a halogen atom, a hydroxyl group, a carboxyl group, or a nitro group, and the methylene group contained in the hydrocarbon group may be replaced with -O-, -CO-, or -N(R17)-. R 17 represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. If there are multiple R 17 groups, they may be the same or different from one another. R 18e to R 18f independently represent a hydrocarbon group having 1 to 18 carbon atoms, which may have substituents, and the methylene group contained in the hydrocarbon group may be replaced with -O-, -CO-, or -N(R 17)-. R 17a represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. 【Chemistry 4】 [In formula (I-C), R5 to R16 independently represent a hydrogen atom, a halogen atom, or a combination of a phenoxy group and a tert-butyl group or a tert-octyl group. R 17b and R 17c independently represent a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents.

2. The colored resin composition according to claim 1, further comprising a polymerizable compound and a polymerization initiator.

3. A color filter formed from the colored resin composition according to claim 1 or 2.

4. A display device including the color filter described in claim 3.

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