Yellow compounds, coloring compositions containing the compounds, colorants for color filters, and color filters

Abstract

To provide a yellowish compound improved in heat resistance and solubility in organic solvents.SOLUTION: The compound is represented by the formula (1). [Each Q is independently a group represented by the formula (2); n is an integer from 2 to 10; L is a divalent to decavalent group; and each Z is independently a divalent or trivalent group.]SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a yellow compound, a coloring composition containing the compound, a coloring agent for color filters containing the coloring composition, and a color filter using the coloring composition. [Background technology]

[0002] To date, various pigments such as quinophthalone pigments, azo pigments, and diketopyrrolopyrrole pigments have been developed (Patent Documents 1-4). These pigments are used as colorants in color filters for liquid crystal and electroluminescent (EL) display devices. Color filters are manufactured by laminating colored layers on a translucent substrate such as glass using dyeing, pigment dispersion, printing, or electrodeposition methods. Quinophthalone pigments are yellow compounds synthesized by the condensation of quinaldine and phthalic anhydride, and are used as colorants for color filters due to their vividness (Patent Documents 1, 2, 5, 6, Non-Patent Document 1). However, with the increasing image quality of displays, the performance required of color filters has increased, and it is necessary to further improve coloring power, brightness, and contrast.

[0003] Since pigments are generally insoluble in solvents, they exist as fine particles in color filters containing resins and other materials. Therefore, color filters using pigments are known to be affected by the reflection and scattering of transmitted light at the surface of the pigment particles, which affects transparency and color purity, and also reduces the contrast ratio of color liquid crystal displays due to the depolarization effect caused by reflection.

[0004] To improve the problem of reduced contrast ratio, methods using only dyes as colorants or using a combination of dyes and pigments have been proposed. Since dyes are soluble in solvents, color filters using dyes exhibit less depolarization compared to those using only pigments as colorants, resulting in superior spectral characteristics and improvements in contrast and brightness. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Special Publication No. 47-3476 [Patent Document 2] Japanese Patent Publication No. 2012-193318 [Patent Document 3] Japanese Patent Publication No. 2012-12498 [Patent Document 4] Japanese Patent Publication No. 2001-220520 [Patent Document 5] Japanese Patent Publication No. 2019-104897 [Patent Document 6] Japanese Patent Publication No. 2019-123856 [Non-patent literature]

[0006] [Non-Patent Document 1] Kunihiro Ichimura (supervisor), "Process Technology and Chemicals of Cutting-Edge Color Filters," CMC Publishing Co., Ltd., 2006, p. 80. [Overview of the Initiative] [Problems that the invention aims to solve]

[0007] The present invention was made to solve the above problems, and aims to provide a coloring composition containing a yellow compound that has improved solubility and heat resistance in organic solvents (such as propylene glycol monomethyl ether acetate (PGMEA)) and excellent color characteristics such as coloring power, vividness, and hue, a coloring agent for color filters containing the coloring composition, and a color filter using the coloring agent. [Means for solving the problem]

[0008] This invention was obtained as a result of diligent research for the above-mentioned purpose, and its gist is as follows.

[0009] 1. A compound represented by the following general formula (1).

[0010] [ka]

[0011] [In equation (1), Q is a base that is independently represented by the following general equation (2), n represents an integer between 2 and 10. L represents a group with 2 to 10 valencies.

[0012] [ka]

[0013] [In formula (2), R 1 ~R 9 Each of them operates independently. Hydrogen atom (-H), hydroxyl group (-OH), halogen atom, cyano group (-CN), nitro group (-NO2), An amino group having 0 to 25 carbon atoms, which may have substituents. A sulfonyl group having 0 to 25 carbon atoms, which may have substituents. Linear, branched, or cyclic alkyl groups having 1 to 25 carbon atoms, which may have substituents. A linear, branched, or cyclic alkenyl group having 2 to 25 carbon atoms, which may have substituents. Linear, branched, or cyclic alkoxy groups having 1 to 25 carbon atoms, which may have substituents. Acyl groups having 1 to 25 carbon atoms, which may have substituents, Ether groups having 0 to 25 carbon atoms, which may have substituents. A substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or This represents a heterocyclic group having 5 to 25 ring-forming atoms, which may have substituents. R 1 ~R 9 These groups may be bonded to each other to form a ring. Each Z is independently either a divalent or trivalent group. An amino group having 0 to 25 carbon atoms, which may have substituents. A linear, branched, or cyclic alkylene group having 1 to 25 carbon atoms, which may have substituents. This represents a group containing one or more types of ether groups or single bonds. Multiple Qs are assumed to be connected to each other via L or Z.

[0014] 2. In the above general formula (1), L is An amino group having 0 to 25 carbon atoms, which may have substituents. A linear, branched, or cyclic alkylene group having 1 to 25 carbon atoms, which may have substituents. Ether groups having 0 to 25 carbon atoms, which may have substituents. A substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or A compound which is a heterocyclic group having 5 to 25 ring-forming atoms, which may have substituents.

[0015] 3. A compound in which Z in the general formula (2) is an amino group having 1 to 20 carbon atoms, which may have substituents.

[0016] 4. In the above general formula (2), R 1 ~R 9 hydrogen atoms, halogen atoms, Linear or branched alkyl groups having 1 to 20 carbon atoms, which may have substituents. A linear alkenyl group having 2 to 20 carbon atoms, which may have substituents, or A compound which is an acyl group having 1 to 20 carbon atoms, which may have substituents.

[0017] A colored composition containing the compound, wherein the solubility in propylene glycol monomethyl ether acetate (PGMEA) at 5.23 to 27°C is 1% by mass or more.

[0018] 6. Using a coating film containing the above compound, The color difference (ΔE) of the color values ​​before and after heating at 220-240°C. * ab ) is 3.5 or less. A colored composition containing the aforementioned compound.

[0019] 7. A coloring agent for color filters containing the compound or coloring composition.

[0020] 8. A color filter using the coloring agent for color filters mentioned above. [Effects of the Invention]

[0021] The compound according to the present invention has superior solubility in organic solvents such as PGMEA and superior heat resistance during film formation compared to conventional yellow compounds. Therefore, a colored composition containing the compound according to the present invention is useful as a coloring agent for color filters. [Modes for carrying out the invention]

[0022] The embodiments of the present invention will be described in detail below. It should be noted that the present invention is not limited to the embodiments described below, and can be implemented with various modifications within the scope of its essence. First, the compound represented by the general formula (1) will be described.

[0023] The compound of the present invention is represented by the following general formula (1). In general formula (1), each Q is independently a group represented by the following general formula (2), where n is an integer from 2 to 10 and L is a group with a valency of 2 to 10. The multiple Qs may be the same or different.

[0024] [ka]

[0025] [ka]

[0026] Therefore, general formula (1) can be expressed using general formula (2) as shown in general formula (1-2) below.

[0027] [Chem.]]

[0028] Here, in general formula (1), when n is 2, a plurality of Q groups are respectively denoted as Q 1 and Q 2 , Q 1 and Q 2 are bonded as "Q 1 -L-Q 2 " via L as shown in the following formula (1-3).

[0029] [Chem.]]

[0030] Further, in general formula (1), when n is 3, a plurality of Q groups are respectively denoted as Q 1 , Q 2 and Q 3 , Q 1 to Q 3 may be bonded via L as shown in the following formula (1-4), and each of Q 1 to Q 3 may be directly bonded to each other, or may be interchanged with each other. The same applies when n is 4 or more: a plurality of Q groups can be bonded to each other via L as shown in the following formula (1-4).

[0031] [Chem.]]

[0032] As described above, in general formula (1), n represents an integer of 2 to 10, and even when Q 1 to Q 10 exist as the plurality of Q groups, each of Q 1 to Q 10 may be bonded via L, and Q 1 to Q 10Each of these elements may be directly bonded to the others, or they may be interchangeable. Therefore, L represents a base with valencies from 2 to 10, corresponding to n. It is preferable that n is between 2 and 6, and more preferably between 2 and 4.

[0033] R in general formula (2) 1 ~R 9 Examples of "halogen atoms" represented by this formula include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. Fluorine atoms or chlorine atoms are preferred as the "halogen atoms".

[0034] In general formula (2), R 1 ~R 9 The "amino group having 0 to 25 carbon atoms which may have substituents" represented by may or may not have substituents, and if it does have substituents, it is represented as "-NR 10 R 11 "The substituent R is expressed as " 10 and R 11 The amino group includes an amino group having a substituent, and examples include an unsubstituted amino group (-NH2), a monosubstituted amino group, a disubstituted amino group, etc. The number of carbon atoms in the monosubstituted or disubstituted amino group is, for example, 1 to 25, may be 1 to 20, or may be 2 to 10. The amino group having 0 to 25 carbon atoms which may have substituents may be a group to which a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, an aromatic hydrocarbon group having 6 to 25 carbon atoms, an acyl group having 0 to 25 carbon atoms, or a heterocyclic group having 5 to 25 ring-forming atoms is bonded via -NH-, -N<, or -N=CH- described later. Examples of monosubstituted amino groups include ethylamino group, butylamino group, acetylamino group, and phenylamino group. Examples of disubstituted amino groups include dialkylamino groups with 2 to 25 carbon atoms, such as dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group, and dihexylamino group; dialkenylamino groups with 4 to 25 carbon atoms, such as diallylamino group; and diphenylamino group, N-acetyl-N-phenylamino group, and (n-butyl)-N-phenylamino group.

[0035] In general formula (2), R 1 ~R 9 The "sulfonyl group having 0 to 25 carbon atoms which may have substituents" represented by "-SO2-R 100 (or, "-S(=O)2-R 100 The substituent R is represented as ") 100 This refers to a sulfonyl group having "-SO2-R 100 The group may not contain carbon atoms, and may be, for example, "-SO3H" or "-SO3M" containing an alkali metal atom "M". Examples of alkali metal atoms "M" in this invention include lithium atoms (Li), sodium atoms (Na), potassium atoms (K), or cesium atoms (Cs), with Li, Na, or K being preferred, Li or Na being more preferred, and Na being particularly preferred. 100 The number of carbon atoms is 0 to 25, may be 1 to 20, or may be 1 to 10. Examples of sulfonyl groups that may have substituents with 0 to 25 carbon atoms include the above-mentioned -SO3H and -SO3M, as well as sulfonamide groups (-S(=O)2-NH2), mesyl groups, tosyl groups, etc.

[0036] In general formula (2), R 1 ~R 9 Examples of "linear, branched, or cyclic alkyl groups having 1 to 25 carbon atoms that may have substituents" as expressed in the formula include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups; branched alkyl groups such as isopropyl, isobutyl, s-butyl, t-butyl, isooctyl, and 2-ethylhexyl groups; cyclic alkyl groups (cycloalkyl groups) such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl groups, as well as 1-adamantyl and 2-adamantyl groups.

[0037] In general formula (2), R 1 ~R 9In the expression "linear, branched, or cyclic alkenyl groups having 2 to 25 carbon atoms that may have substituents," the "linear, branched, or cyclic alkenyl groups having 2 to 25 carbon atoms" specifically include linear or branched alkenyl groups such as vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 1-pentenyl, 1-hexenyl, isopropenyl, and isobutenyl groups; cyclic alkenyl groups (cycloalkenyl groups) such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl groups; or groups formed by the bonding of multiple such linear, branched, or cyclic alkenyl groups.

[0038] In general formula (2), R 1 ~R 9 In the expression "linear, branched, or cyclic alkoxy groups having 1 to 25 carbon atoms that may have substituents," examples of "linear, branched, or cyclic alkoxy groups having 1 to 25 carbon atoms" include linear alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, and decyloxy groups; branched alkoxy groups such as isopropoxy, isobutoxy, s-butoxy, t-butoxy, and isooctyloxy groups; cyclic alkoxy groups (cycloalkoxy groups) such as cyclopropoxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, cyclononyloxy, and cyclodecyloxy groups; and 1-adamantyloxy and 2-adamantyloxy groups.

[0039] In general formula (2), R 1 ~R 9 The "acyl group having 1 to 25 carbon atoms which may have substituents" represented by "―(C=O)―R 101 substituent R represented by " 101 This refers to a group having substituent R. 101This group may contain a carbon atom, a nitrogen atom, or not contain a carbon atom. Substituent R 101 However, if the group contains a carbon atom, the substituent R 101 The number of carbon atoms may be, for example, 1 to 25 or 1 to 20. Substituent R 101 However, if the group contains a nitrogen atom, or if the group does not contain a carbon atom, substituent R 101 The number of carbon atoms may be, for example, 0 to 25 or 0 to 20. Substituent R 101 Examples include -H, -CH3, -CH2CH2CH3, -CH=CH2, -C6H5 (phenyl group), -NH2, -NHCH3, -NHCH2CH3, dimethylamino group, diethylamino group, di(n-propyl)amino group, di(n-butyl)amino group, etc., but the aforementioned R 1 ~R 9 It may be the same as the "amino group having 0 to 25 carbon atoms which may have substituents" represented by . Specifically, examples of "acyl groups having 1 to 25 carbon atoms which may have substituents" include the formyl group, acetyl group, propionyl group, acryl group, benzoyl group, etc. "―(C=O)―R 101 " may be an amide group, a primary amide group, or a secondary amide group if it contains a nitrogen atom, and R 101 is the aforementioned R 1 ~R 9 The example given is "-NR," which is an amino group with 0 to 25 carbon atoms and a substituent. 10 R 11 This may be a monosubstituted amino group or a disubstituted amino group represented as ".

[0040] In general formula (2), R 1 ~R 9 The "ether group having 0 to 25 carbon atoms which may have substituents" represented by "-O-R" 102 substituent R represented by " 102 This refers to an ether group having substituent R. 102This group may contain carbon atoms or may not contain carbon atoms. Specifically, examples of "ether groups with 0 to 25 carbon atoms that may have substituents" include aminooxy groups, ester groups represented as "-O-(C=O)-R" (where R is any alkyl group or aromatic hydrocarbon group, etc.), phosphate groups, and phosphate ester groups.

[0041] In general formula (2), R 1 ~R 9 In the expression "aromatic hydrocarbon groups having 6 to 25 carbon atoms which may have substituents," examples of aromatic hydrocarbon groups having 6 to 25 carbon atoms include phenyl groups, biphenylyl groups, terphenylyl groups, naphthyl groups, anthracenyl groups (anthryl groups), phenanthryl groups, fluorenyl groups, indenyl groups, pyrenyl groups, perilenyl groups, fluoranthenyl groups, triphenylenyl groups, and other aromatic hydrocarbon groups (in this invention, "aromatic hydrocarbon groups" also include aryl groups or fused polycyclic aromatic groups).

[0042] In general formula (2), R 1 ~R 9 In the expression "heterocyclic groups with 5 to 25 ring-forming atoms that may have substituents," examples of "heterocyclic groups with 5 to 25 ring-forming atoms" include, specifically, heterocyclic groups (or heteroaromatic hydrocarbon groups) such as pyridyl group, pyrimidinyl group, triazinyl group, imidazolyl group, pyrazolyl group, triazolyl group, thienyl group, furyl group (furanyl group), pyrrolyl group, quinolyl group, isoquinolyl group, naphthylidinyl group, indolyl group, acridinyl group, phenanthrolinyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, and carboninyl group.

[0043] In general formula (2), R 1 ~R 9 It is represented "Amino groups with substituents and 0 to 25 carbon atoms," "Sulfonyl groups with substituents and 0 to 25 carbon atoms," "Linear, branched, or cyclic alkyl groups having 1 to 25 carbon atoms and having substituents," "Linear, branched, or cyclic alkenyl groups having 2 to 25 carbon atoms and having substituents," "Linear, branched, or cyclic alkoxy groups having 1 to 25 carbon atoms and having substituents," "Acyl groups with substituents, having 1 to 25 carbon atoms" "Ether groups with substituents and 0 to 25 carbon atoms" "Aromatic hydrocarbon groups with substituents and 6 to 25 carbon atoms," or, In "heterocyclic groups with 5 to 25 ring-forming atoms having substituents," the "substituents" are: Specifically, deuterium atoms, hydroxyl groups, thiol groups, cyano groups, and nitro groups; Halogen atoms such as fluorine, chlorine, bromine, and iodine; Amino groups with 0 to 20 carbon atoms; Sulfonyl groups with 0 to 20 carbon atoms; Linear, branched, or cyclic alkyl groups having 1 to 20 carbon atoms; A linear, branched, or cyclic alkenyl group having 2 to 20 carbon atoms; Linear, branched, or cyclic alkoxy groups having 1 to 20 carbon atoms; Acyl groups with 1 to 20 carbon atoms; Ether groups with 1 to 20 carbon atoms; Aromatic hydrocarbon groups or fused polycyclic aromatic groups having 6 to 20 carbon atoms; Examples include heterocyclic groups with 5 to 20 ring-forming atoms. Note that if a "substituent" contains a carbon atom, that carbon atom is not included in the above "0 to 25 carbon atoms", "1 to 25 carbon atoms", and "6 to 25 carbon atoms". These "substituents" may be present one at a time or multiple times, and if multiple are present, they may be identical or different. Furthermore, these "substituents" may also have the substituents exemplified above. These substituents may also be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms (-O-), or sulfur atoms (-S-) to form a ring. However, the above R 1 ~R 9 Each group represented by may have a maximum of 10 substituents, and the maximum number of carbon atoms in each group may be 100.

[0044] Note that in general formula (2), R 1 ~R 9 In each of the above groups having a "substituent" represented by, the "substituent" listed is "Amino groups with 0 to 20 carbon atoms" "Sulfonyl groups with 0 to 20 carbon atoms" "Linear, branched, or cyclic alkyl groups with 1 to 20 carbon atoms," "Linear, branched, or cyclic alkenyl groups with 2 to 20 carbon atoms," "Linear, branched, or cyclic alkoxy groups having 1 to 20 carbon atoms," "Acyl groups with 1 to 20 carbon atoms" "Ether groups with 1 to 20 carbon atoms" "Aromatic hydrocarbon groups or condensed polycyclic aromatic groups with 6 to 20 carbon atoms," or Specifically, "heterocyclic groups with 5 to 20 ring-forming atoms" include: Amino groups; monosubstituted or disubstituted amino groups having linear alkyl groups with 1 to 20 carbon atoms or branched alkyl groups with 3 to 20 carbon atoms, or aromatic hydrocarbon groups with 6 to 20 carbon atoms, such as methylamino group, dimethylamino group, diethylamino group, ethylmethylamino group, dipropylamino group, di-t-butylamino group, and diphenylamino group; Groups having a sulfonyl group (―S(=O)2―) with 0 to 20 carbon atoms, such as sulfonamide groups (―S(=O)2―NH2), mesyl groups, and tosyl groups;―SO3 - , -SO3H, -SO3M (where M is an alkali metal atom); Linear alkyl groups with 1 to 20 carbon atoms or branched alkyl groups with 3 to 20 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, n-hexyl group, 2-ethylhexyl group, heptyl group, octyl group, isooctyl group, nonyl group, and decyl group; cyclic alkyl groups (cycloalkyl groups) with 3 to 20 carbon atoms, such as cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, cyclononyl group, and cyclodecyl group; 1-adamantyl group, 2-adamantyl group; Vinyl group, 1-propenyl group, allyl group, 1-butenyl group, 2-butenyl group, 1-pentenyl group, 1-hexenyl group, isopropenyl group, isobutenyl group, or linear alkenyl groups with 2 to 20 carbon atoms or branched alkenyl groups with 3 to 20 carbon atoms formed by the bonding of multiple such alkenyl groups; cyclic alkenyl groups with 3 to 20 carbon atoms (cycloalkenyl groups) such as cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, and cycloheptenyl group; Linear alkoxy groups with 1 to 20 carbon atoms or branched alkoxy groups with 3 to 20 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, isopropoxy, isobutoxy, s-butoxy, t-butoxy, and isooctyloxy; cyclic alkoxy groups (cycloalkoxy groups) with 3 to 20 carbon atoms, such as cyclopropoxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy, cyclononyloxy, and cyclodecyloxy; 1-adamantyloxy and 2-adamantyloxy groups; Acyl groups with 1 to 20 carbon atoms, such as formyl, acetyl, propionyl, acryl, and benzoyl groups; Groups containing ether groups (-O-), such as ether groups (-O-), aminooxy groups, ester groups represented as "-O-(C=O)-R" (where R is any alkyl group or aromatic hydrocarbon group, etc.), phosphate groups, and phosphate ester groups, with ether groups (-O-) having 0 to 20 carbon atoms; Aromatic hydrocarbon groups or condensed polycyclic aromatic groups having 6 to 20 carbon atoms, such as phenyl groups, biphenylyl groups, terphenylyl groups, naphthyl groups, anthracenyl groups (anthryl groups), phenanthryl groups, fluorenyl groups, indenyl groups, pyrenyl groups, perilenyl groups, fluoranthenyl groups, and triphenylenyl groups; Heterocyclic groups with 5 to 20 ring-forming atoms, such as pyridyl group, pyrimidylinyl group, triazinyl group, thienyl group, furyl group (furanyl group), pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, quinolyl group, isoquinolyl group, naphthylidinyl group, acridinyl group, phenanthrolinyl group, benzofuranyl group, benzothienyl group, oxazolyl group, indolyl group, carbazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, and carbonyl group; Examples include aryloxy groups with 6 to 19 carbon atoms, such as phenyloxy, tolyloxy, biphenylyloxy, naphthyloxy, anthracenyloxy, and phenantrenyloxy groups; and others.

[0045] In general formula (2), R 1 ~R 9 The adjacent groups may be bonded to each other via single bonds, substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms to form a ring.

[0046] In general formula (2), R 1 ~R 9 As for, Hydrogen atom, hydroxyl group, halogen atom, nitro group, cyano group, An amino group having 1 to 20 carbon atoms, which may have substituents. Linear alkyl groups having 1 to 20 carbon atoms or branched alkyl groups having 3 to 20 carbon atoms, which may have substituents. a linear alkenyl group having 2 to 20 carbon atoms or a branched alkenyl group having 3 to 20 carbon atoms, which may have a substituent, a linear alkoxy group having 2 to 20 carbon atoms or a branched alkoxy group having 3 to 20 carbon atoms, which may have a substituent, an acyl group having 1 to 20 carbon atoms which may have a substituent, an ether group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent is preferable; a hydrogen atom, a halogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent, a linear alkenyl group having 2 to 20 carbon atoms which may have a substituent, or an acyl group having 1 to 20 carbon atoms which may have a substituent is more preferable. R 7 or R 8 is more preferably a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent, a linear alkenyl group having 2 to 20 carbon atoms which may have a substituent, or an acyl group having 1 to 20 carbon atoms which may have a substituent, and R 6 or R 9 is further more preferably a hydrogen atom or a halogen atom.

[0047] In general formula (1), n groups Q represented by general formula (2) are contained. In general formula (2), a plurality (n) of Z groups are each independently the same or different, and are a divalent group or a trivalent group.

[0048] In general formula (1), a plurality of Q groups are bonded to each other via L or Z. When Z is a divalent group, for example, when the general formula (1) is represented as "Q 1 -L-Q 2 " as in general formula (1-3), it is represented by the following formula (2-1). In this case, a plurality of R 1 to R 9These can be independent, identical, or different. Also, when expressed as in formula (2-1) below, one or more of the multiple Zs may be trivalent groups, and Z may be an appropriate group, for example, R 10 Ya R 11 It may also be a trivalent group having , and specifically it may be represented as shown in formula (2-2) below.

[0049] [ka]

[0050] [ka]

[0051] In general formula (1), when multiple Qs are bonded via Z, each Q can be bonded to one another via a divalent or trivalent group represented by Z, for example, as shown in formula (2-3) below.

[0052] [ka]

[0053] In general formula (1), the group represented by "L" represents a group with a valency of 2 to 10. Specific examples of L include any group used to form a 2 to 10-valency group, as shown below. Furthermore, L and multiple Qs can be bonded to each other at any substituent site of the groups shown below. These bases include, "An amino group (or imino group) having 0 to 25 carbon atoms, which may have substituents," "Sulfonyl groups having 0 to 25 carbon atoms, which may have substituents," "Linear, branched, or cyclic alkyl groups having 1 to 25 carbon atoms, which may have substituents," "A linear, branched, or cyclic alkenyl group having 2 to 25 carbon atoms, which may have substituents." "A straight-chain, branched or cyclic alkoxy group having 1 to 25 carbon atoms, which may have a substituent", "An acyl group having 1 to 25 carbon atoms, which may have a substituent", "An ether group having 0 to 25 carbon atoms, which may have a substituent", "An aromatic hydrocarbon group having 6 to 25 carbon atoms, which may have a substituent", or "A heterocyclic group having 5 to 25 ring-forming atoms, which may have a substituent" can be mentioned. Specifically, these groups are the same as those exemplified as R 1 to R 9 in General Formula (2). The "substituents" that these "groups" may have are also the same as the "substituents" that the group represented by R 1 to R 9 may have. L represented by these groups can be a group having any valence from 2 to 10 depending on the number (n) of Q or bonding to a plurality of Q at a site that may optionally have a substituent. For example, "a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms, which may have a substituent" may be "a straight-chain, branched or cyclic alkylene group having 1 to 25 carbon atoms, which may have a substituent", and a substituent may be bonded to a part of these "alkylene groups" to form a group having a valence of 3 or higher. These "groups" or "substituents" may contain only one, or may contain a plurality thereof; when a plurality are contained, they may be the same as or different from each other. Furthermore, these "groups" or "substituents" may further have the groups or substituents exemplified above. In addition, these "groups" or "substituents" may mutually bond to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. However, the maximum number of the aforementioned "groups" or "substituents" contained in L is 10, and the maximum number of carbon atoms in each group is 100.

[0054] In general formula (1), if L represents a group with a 2- to 10-valent charge and is a group that can bond to any substituent site of a "linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms that may have substituents," then L is expressed as "a linear, branched, or cyclic alkylene group having 1 to 25 carbon atoms that may have substituents." Specifically, this includes methylene group, ethylene group, -CHCH3-, n-propylene group (propane-1,3-diyl group), i-propylene group, propane-1,2-diyl group, propane-2,2-diyl group, n-butylene group, i-butylene group, s-butylene group, t-butylene group, n-pentylene group, neopentylene group, and n-hexylene group (hexane-1,6-diyl group, -C6H 12 Examples include, but are not limited to, linear or branched alkylene groups such as n-heptylene, n-octylene, n-nonylene, and n-decylene groups, or cyclic alkylene groups such as cyclopropylene, cyclopentylene, and cyclohexylene groups, with one or more of these groups bonded together.

[0055] In general formula (1), L is An amino group having 0 to 25 carbon atoms, which may have substituents. A linear, branched, or cyclic alkylene group having 1 to 25 carbon atoms, which may have substituents. Ether groups having 0 to 25 carbon atoms, which may have substituents. A substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or A heterocyclic group having 5 to 25 ring-forming atoms, which may have substituents, is preferred. A linear or branched alkylene group having 1 to 25 carbon atoms, which may have substituents, is more preferable.

[0056] In general formula (2), the divalent or trivalent group represented by Z is, An amino group having 0 to 25 carbon atoms, which may have substituents. A linear, branched, or cyclic alkylene group having 1 to 25 carbon atoms, which may have substituents. This term represents a group containing one or more ether groups or single bonds, and includes cases where these groups are replaced with divalent or trivalent groups at appropriate sites. Multiple identical or different amino groups, alkylene groups, or ether groups may be included.

[0057] In general formula (2), Z is defined as "an amino group having 0 to 25 carbon atoms which may have substituents" and can be -N<, -N=CH-, or R in general formula (2). 1 ~R 9 Examples include a group similar to the "amino group having 0 to 25 carbon atoms which may have substituents" represented by , in which one of the substituent sites is replaced with a divalent or trivalent group, and substituent R 12 Therefore, -NR 12 ―,>N―R 12 ―, ―R 12 ―NR 12 ―R 12 ―, ―R 12 ―NH―NR 12 ―R 12 —It can be expressed as such. Substituent R 12 For example, R 1 ~R 9 Examples of substituents are similar to those in the "amino group having 0 to 25 carbon atoms which may have substituents" represented by . 12 These may be the same or different. Furthermore, if Z in general formula (2) contains multiple "amino groups with 0 to 25 carbon atoms that may have substituents," each Q can bond to a different Q via Z.

[0058] In general formula (2), the "linear, branched, or cyclic alkylene group having 1 to 25 carbon atoms, which may have substituents" represented by Z is R 1 ~R 9Examples include a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms that may have substituents, as represented by R, obtained by replacing a monovalent group with a divalent group at any position. Specifically, it may be the same as the linear, branched, or cyclic alkylene group having 1 to 25 carbon atoms that may have substituents, as represented by L. As for the substituents in the linear, branched, or cyclic alkylene group having 1 to 25 carbon atoms that may have substituents, R 1 ~R 9 Examples of substituents are similar to those in the "linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, which may have substituents" represented by . These alkylene groups may branch to form trivalent groups.

[0059] In general formula (2), Z is preferably a divalent or trivalent group, comprising an amino group having 1 to 20 carbon atoms which may have substituents, a linear, branched or cyclic alkylene group having 1 to 20 carbon atoms which may have substituents, or an ether group, and more preferably an amino group having 1 to 20 carbon atoms which may have substituents.

[0060] Furthermore, in the above, "Linear, branched, or cyclic alkyl groups having 1 to 25 carbon atoms" is preferably "linear alkyl groups having 1 to 25 carbon atoms, or branched or cyclic alkyl groups having 3 to 25 carbon atoms." The "linear, branched, or cyclic alkenyl group having 2 to 25 carbon atoms" is preferably a "linear alkenyl group having 2 to 25 carbon atoms, or a branched or cyclic alkenyl group having 3 to 25 carbon atoms." The "linear, branched, or cyclic alkoxy group having 1 to 25 carbon atoms" is preferably a "linear alkoxy group having 1 to 25 carbon atoms, or a branched or cyclic alkoxy group having 3 to 25 carbon atoms." The "linear, branched, or cyclic alkylene group having 1 to 25 carbon atoms" is preferably a "linear alkylene group having 1 to 25 carbon atoms, or a branched or cyclic alkylene group having 3 to 25 carbon atoms."

[0061] The compound of the present invention is One divalent to decavalent group L [synonymous with L in general formula (1)], n identical or different monovalent groups R represented by the following general formula (3) 0 , n identical or different monovalent groups R 12 [Synonymous with the substituent in general formula (2) or a hydrogen atom.] and n identical or distinct divalent or trivalent groups Z [synonymous with Z in general formula (2)]. It consists of, n represents an integer between 2 and 10. L can only combine with Z. R 0 It combines only with Z, R 12 It combines only with Z, Z is R 0 It combines with and L, R 12 and is combined with one or two selected from the other group of Z. It is a compound.

[0062] [ka] [In formula (3), R 1 ~R 9 This is synonymous with the above.

[0063] The compound represented by general formula (1) (hereinafter simply referred to as compound (1)) encompasses all possible stereoisomers and tautomers. Specific examples of compound (1) are shown below, but the present invention is not limited to these. Note that some hydrogen atoms have been omitted in the following structural formulas.

[0064] [ka]

[0065]

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[0070]

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[0071]

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[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] [ka]

[0080] [ka]

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[0083] [ka]

[0084] Compounds represented by general formula (1) can be synthesized by the following method. Below, in general formula (1), n ​​is 2 and Z is any substituent R 10 It is an amino group having L is -C6H 12 The following shows an example of a combination when represented by ―. By reacting an 8-amino-2-methylquinoline derivative having the corresponding substituent with 1,6-diiodohexane in a suitable solvent and temperature, the following intermediate (X-1) having the corresponding substituent can be obtained.

[0085] [ka]

[0086] Furthermore, by subjecting the obtained intermediate (X-1) to a trimellitic anhydride having the corresponding substituent to a dehydration condensation reaction in a suitable solvent and temperature, the compound of the present invention represented by general formula (1) can be obtained.

[0087] In the present invention, methods for purifying the product include known methods such as purification by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., and recrystallization or crystallization using solvents. Furthermore, for the identification and analysis of these compounds, nuclear magnetic resonance spectroscopy (NMR), absorbance measurement and ultraviolet-visible absorption spectroscopy (UV-Vis) measurement using a spectrophotometer, and thermogravimetric analysis-differential thermal analysis (TG-DTA) can be performed. These analytical methods can also be used to evaluate the solubility, color, and heat resistance of the obtained compounds.

[0088] The solubility of the compounds of the present invention is expressed in terms of solubility, which represents the maximum amount of a substance that can dissolve in a particular solvent, and is expressed in units such as "mass%(solvent name, temperature)". Solubility can be obtained, for example, by mixing a sample with a specific solvent, stirring the solvent at a constant temperature for a certain time, and measuring the concentration of the prepared saturated solution. It can also be obtained by measuring the concentration of the dissolved portion using methods such as liquid chromatography (LC) or absorbance measurement.

[0089] By performing thermogravimetric-differential thermal analysis (TG-DTA) on the compounds of the present invention, the thermal decomposition temperature can be analyzed, which can serve as an indicator of heat resistance. In colored compositions, the thermal decomposition temperature of the pigment compound is preferably 250°C or higher. When applied to color filters, a higher thermal decomposition temperature is preferable.

[0090] The compound of the present invention can be mixed with various resin solutions used as colorants for color filters, such as acrylic resin, applied to a glass substrate by a method such as spin coating, and heated and dried to produce a coating film. The resulting coating film can be evaluated for its color properties by measuring its color using a spectrophotometer and obtaining its color value. The color value is CIE L * a * b * Color systems are commonly used. Specifically, the color value L of a film sample is used. * a * , b * Measure the color difference (ΔE) of the color values ​​before and after heating at an appropriate temperature. * ab ) allows us to determine heat resistance. When applied to color filters, the color difference at temperatures around 230°C (for example, within the range of 220-240°C) can be used as an indicator of heat resistance. ΔE * ab The smaller the value, the better, meaning there is less discoloration due to thermal decomposition. ΔE * ab The ratio is preferably 3.5 or less, and more preferably 3 or less. The less the color change due to thermal decomposition of the pigment compound, the better the coloring composition and colorant for color filters can be obtained in terms of color characteristics such as coloring power, vividness, and hue.

[0091] The coloring compositions contained in color filters require that the dye compounds be well dissolved or dispersed in the resin and organic solvent; therefore, it is preferable that the compounds contained in these coloring compositions have high solubility in organic solvents. Specific examples of organic solvents include esters such as ethyl acetate and n-butyl acetate; ethers such as diethyl ether and propylene glycol monomethyl ether (PGME); ether esters such as propylene glycol monomethyl ether acetate (PGMEA); ketones such as acetone and cyclohexanone; alcohols such as methanol and ethanol; diacetone alcohol (DAA), etc.; aromatic hydrocarbons such as benzene, toluene, and xylene; amides such as N,N-dimethylformamide (DMF) and N-methylpyrrolidone (NMP); and dimethyl sulfoxide (DMSO). These solvents may be used individually or in mixtures of two or more. Among these, the compounds according to the present invention exhibit excellent solubility in PGME and PGMEA. For example, the solubility (mass%) in PGMEA in a temperature range of 25±2°C (temperatures within the range of 23-27°C) (solvent PGMEA, 25±2°C) is preferably 0.1% by mass or more, more preferably 1% by mass or more, and particularly preferably 2% by mass or more.

[0092] The compound represented by general formula (1) preferably has a maximum absorption wavelength in the visible light region in solution, for example, in the range of 350 to 700 nm, that is in the range of 400 to 500 nm.

[0093] The colored composition of the present invention contains the compound of the present invention represented by general formula (1), and may contain a compound with one type of structure, or may contain compounds with two or more types of structures. In the present invention, it is preferable that the compound has only one type of structure.

[0094] To enhance the performance of the coloring composition as a coloring agent for color filters, the coloring composition of the present invention may contain other components of the compound, such as surfactants, dispersants, defoamers, leveling agents, and other additives mixed during the manufacture of coloring agents for color filters. However, the content of these additives in the coloring composition is preferably appropriate, and preferably within a range that does not reduce or excessively improve the solubility of the coloring composition or affect the manufacture of color filters. These additives can be added at any time during the preparation of the coloring composition.

[0095] The colorant for color filters of the present invention comprises a coloring composition containing a compound represented by general formula (1) and components commonly used in the manufacture of color filters. A typical color filter is obtained, for example, by using a photolithography process, by mixing dyes or pigments with resin components (including monomers, oligomers, binder components, and resist components) and a solvent to prepare a liquid, which is then applied to a substrate such as glass or resin, photopolymerized using a photomask to create a colored pattern of a dye-resin composite film that is soluble / insoluble in the solvent, and then washed and heated. Because the compound of the present invention has excellent solubility, it has excellent dispersibility with the materials used in the manufacture of these color filters, and can be mixed with other materials as needed to form a film and evaluate its heat resistance and light absorption properties. Furthermore, in electrodeposition and printing methods, a colored pattern can be created using a mixture of dyes with resin and other components. Accordingly, specific components of the colorant for color filters of the present invention include the compound represented by general formula (1), other dyes and pigments, resin components, organic solvents, and other additives such as photopolymerization initiators. Furthermore, you may select or discard these ingredients, or add other ingredients as needed.

[0096] When the coloring composition of the present invention is used as a coloring agent for color filters, it can be used as a yellow color filter, but it can also be mixed with color filters for other colors such as red or green. Furthermore, the coloring composition of the present invention may be used alone, or other known dyes such as other dyes or pigments may be mixed in order to adjust the color tone. Examples of dyes or pigments include basic dyes; acid dyes; disperse dyes; spiron dyes; azo dyes, disazo dyes, quinoline dyes, stilbene dyes, (poly)methine dyes, cyanine dyes, indigo dyes, phthalocyanine dyes, anthraquinone dyes, acridine dyes, triarylmethane dyes, indanthrene dyes, oxazine dyes, dioxazine dyes, naphthol AS dyes, benzimidazolone dyes, pyrazolone dyes, perylene dyes, perinone dyes, quinacridone dyes, isoindolinone dyes, xanthene dyes, diketopyrrolopyrrole dyes, and the like.

[0097] The mixing ratio of other pigments in the colored composition and colorant for color filters of the present invention is preferably 5 to 2000% by mass, and more preferably 10 to 1000% by mass, relative to the compound represented by general formula (1). The mixing ratio of pigment components such as dyes in the liquid colorant for color filters is preferably 0.5 to 70% by mass, and more preferably 1 to 50% by mass, relative to the total colorant.

[0098] As resin components in the colored compositions and colorants for color filters of the present invention, known resins can be used as long as they have the properties necessary for the manufacturing method and use of the color filter resin film formed using them. For example, acrylic resins, olefin resins, styrene resins, polyimide resins, urethane resins, polyester resins, epoxy resins, vinyl ether resins, phenol (novolac) resins, other transparent resins, photocurable resins, thermosetting resins, binder resins, and photoresist resins can be used in appropriate combinations. Copolymers of these resins can also be used in combination. The resin content in these colorants for color filters is preferably 5 to 95% by mass, and more preferably 10 to 50% by mass, in the case of liquid colorants.

[0099] Other additives in the coloring composition and colorants for color filters of the present invention include components necessary for the polymerization and curing of resins, such as photopolymerization initiators and crosslinking agents, as well as surfactants and dispersants necessary for stabilizing the properties of the components in the liquid colorant for color filters. Any known additives can be used, and are not particularly limited. The mixing ratio of the total amount of these additives in the total solid content of the colorant for color filters is preferably 5 to 60% by mass, and more preferably 10 to 40% by mass. [Examples]

[0100] The embodiments of the present invention will be described in detail below with reference to examples, but the present invention is not limited to the following examples. In the synthesis examples, the identification of the compounds is as follows: 1 H-NMR analysis (Bruker Nuclear Magnetic Resonance Spectrometer, Ascend) TM This was done according to 400).

[0101] [Synthesis Example 1] Synthesis of compound (A-5) 48.0 g of 8-amino-2-methylquinoline, 40.2 g of triethylamine, and 384 mL of dichloromethane were placed in a reaction vessel and cooled to below 5°C in an ice bath. 82.8 g of 2,4,6-trimethylbenzoyl chloride was gradually added and the mixture was stirred at 25°C for 7 hours. Water was added to the reaction mixture and extracted with dichloromethane. The extract was concentrated under reduced pressure and purified by column chromatography (support: silica gel, solvent: heptane / dichloromethane / ethyl acetate = 10 / 3 / 1 (volume ratio)). Heptane was added to the reaction mixture and filtered to obtain N-(2,4,6-trimethylbenzoyl)-8-aminoquinaldine (70.8 g, yield 77%). Next, 17.5 g of sodium hydride (60%, dispersed in liquid paraffin) and 300 mL of dehydrated DMF were placed in reaction vessel 1 and cooled to below 5°C in an ice bath. In a separate reaction vessel 2, a solution was prepared by dissolving 60.6 g of the above N-(2,4,6-trimethylbenzoyl)-8-aminoquinaldine in 300 mL of dehydrated DMF. This solution from reaction vessel 2 was gradually added dropwise to reaction vessel 1 and stirred at 25°C for 2 hours. 33.6 g of 1,6-diiodohexane was added and stirred at 25°C for 2 hours. 600 mL of dichloromethane was added to the reaction mixture, and 600 mL of water was gradually added dropwise to extract with dichloromethane. The extract was concentrated under reduced pressure and purified by column chromatography (support: silica gel, solvent: dichloromethane / heptane = 1 / 1 (volume ratio)) to obtain the following intermediate (100) (68.8 g, yield 100%).

[0102] [ka]

[0103] Next, 68.8 g of the intermediate (100) obtained above, 57.4 g of trimellitic anhydride, 36.5 g of benzoic acid, and 130 mL of 1,2,4-trichlorobenzene were placed in a reaction vessel and stirred at 180°C for 8 hours. After cooling to 25°C, 680 mL of toluene was added to the reaction mixture and filtered to obtain the following intermediate (101) (95.0 g, yield 92%).

[0104] [ka]

[0105] Next, 25.0 g of the intermediate (101) obtained above, 8.1 g of dibutylamine, 7.3 g of triethylamine, 200 mL of DMF, and 23.8 g of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) were placed in a reaction vessel and stirred at 25°C for 5 hours. Water was added to the reaction mixture and extracted with dichloromethane. The extract was concentrated under reduced pressure and purified by column chromatography (support: silica gel, solvent: dichloromethane / acetone = 10 / 1 (volume ratio)) to obtain a yellow powder (15.0 g, yield 49%).

[0106] NMR measurements were performed on the obtained yellow powder, and the following 88 hydrogen signals were detected, identifying the structure of the compound represented by formula (A-5) above.

[0107] 1 H-NMR (400MHz, CDCl3): δ(ppm)=13.80-14.60(2H), 8.50-8.80(2H), 7.90-8.20(2H), 7.40-7.80(10H), 6.30-7.20(6H), 3.00-5.20(12H), 2.50-2.70(2H), 2.20-2.50(6H), 1.80-2.10(6H), 0.70-1.80(40H).

[0108] [Synthesis Example 2] Synthesis of compound (A-11) In reaction vessel 1, 8.6 g of sodium hydride (60%, dispersed in liquid paraffin) and 160 mL of dehydrated DMF were added and cooled to below 5°C in an ice bath. In a separate reaction vessel 2, a solution was prepared by dissolving 32.7 g of N-(2,4,6-trimethylbenzoyl)-8-aminoquinaldine obtained in Synthesis Example 1 in 160 mL of dehydrated DMF. This solution from reaction vessel 2 was gradually added dropwise to reaction vessel 1 and stirred at 25°C for 2 hours. 21.2 g of 1,10-diiododecane was added and stirred at 25°C for 2 hours. 320 mL of dichloromethane was added to the reaction mixture, and 320 mL of water was gradually added dropwise, followed by ethyl acetate extraction. The extract was concentrated under reduced pressure and purified by column chromatography (support: silica gel, solvent: dichloromethane / heptane = 1 / 1 (volume ratio)) to obtain the following intermediate (102) (30.7 g, yield 82%).

[0109] [ka]

[0110] Next, 30.7 g of the intermediate (102) obtained above, 24.4 g of 2,3-naphthalenedicarboxylic acid anhydride, 15.0 g of benzoic acid, and 80 mL of 1,2,4-trichlorobenzene were placed in a reaction vessel and stirred at 180°C for 8 hours. After cooling to 25°C, the mixture was purified by column chromatography (support: silica gel, solvent: dichloromethane / acetone = 10 / 1 (volume ratio)) to obtain a yellow powder (7.7 g, yield 17%).

[0111] NMR measurements were performed on the obtained yellow powder, and signals from the following 66 hydrogen atoms were detected, identifying the structure of the compound represented by the following formula (A-11).

[0112] 1 H-NMR (400MHz, CDCl3): δ(ppm)=14.50-15.00(2H), 8.70-8.90(2H), 7.80-8.30(6H), 7.40-7.80(8H), 6.80-7.30(8H), 6.30-6.80(2H), 3.20-5.20(4H), 2.20-2.80(14H), 1.80-2.10(6H), 0.80-1.50(14H).

[0113] [Synthesis Example 3] Synthesis of Compound (A-19) In a reaction vessel, 30.7 g of the intermediate (102) obtained in Synthesis Example 2, 24.0 g of 3-chlorophthalic anhydride, 16.1 g of benzoic acid, and 60 mL of 1,2,4-trichlorobenzene were placed and stirred at 180°C for 8 hours. After cooling to 25°C, the mixture was purified by column chromatography (support: silica gel, solvent: dichloromethane / acetone = 10 / 1 (volume ratio)) to obtain a yellow powder (20.7 g, yield 51%).

[0114] NMR measurements were performed on the obtained yellow powder, and the following 60 hydrogen signals were detected, identifying the structure of the compound represented by the following formula (A-19).

[0115] 1 H-NMR (400MHz, CDCl3): δ(ppm)=14.00-14.60(2H), 8.40-8.70(4H), 7.30-8.10(12H), 6.40-7. 10(4H), 3.50-4.90(4H), 2.50-2.70(2H), 2.20-2.50(12H), 1.70-2.20(6H), 0.70-1.70(14H).

[0116] [Synthesis Example 4] Synthesis of compound (A-20) In a reaction vessel, 27.2 g of the intermediate (100) obtained in Synthesis Example 1, 20.4 g of 4-methylphthalic anhydride, 15.4 g of benzoic acid, and 50 mL of 1,2,4-trichlorobenzene were placed and stirred at 180°C for 8 hours. After cooling to 25°C, the mixture was purified by column chromatography (support: silica gel, solvent: dichloromethane / acetone = 10 / 1 (volume ratio)) to obtain a yellow powder (24.8 g, yield 64%).

[0117] NMR measurements were performed on the obtained yellow powder, and signals from the following 58 hydrogen atoms were detected, identifying the structure of the compound represented by the following formula (A-20).

[0118] 1H-NMR (400MHz, CDCl3): δ(ppm)=13.80-14.50(2H), 7.80-8.80(4H), 7.30-7.70(8H), 6.80-7.20(6H), 6.30-6.70(2H), 3.00-5.20(4H), 2.50-2.70(4H), 2.20-2.50(12H), 1.80-2.10(6H), 0.70-1.70(10H).

[0119] [Synthesis Example 5] Synthesis of Comparative Example Compound (B-1) In a reaction vessel, 47.4 g of N-(2,4,6-trimethylbenzoyl)-N-propyl-8-aminoquinaldine obtained by the same method as in Synthesis Example 1 above, 17.8 g of 4-methylphthalic anhydride, 13.4 g of benzoic acid, and 80 mL of 1,2,4-trichlorobenzene were placed and stirred at 180°C for 8 hours. After cooling to 25°C, the mixture was purified by column chromatography (support: silica gel, solvent: heptane / dichloromethane / ethyl acetate = 10 / 3 / 1 (volume ratio)) to obtain a yellow powder (B-1) (24.0 g, yield 36%).

[0120] NMR measurements were performed on the obtained yellow powder, and signals from the following 30 hydrogen atoms were detected, identifying the structure of the compound represented by the following formula (B-1).

[0121] 1 H-NMR (400MHz, CDCl3): δ(ppm)=13.90-14.50(1H), 8.60-8.80(1H), 7.99-8.10(1H), 7.30-7.80(5H) , 6.90-7.25(2H), 6.40-6.80(1H), 3.20-5.20(2H), 2.30-2.50(6H), 1.90-2.10(3H), 0.60-1.40(8H).

[0122] [ka]

[0123] [Example 1] The solubility (mass%) of the compound (A-5) obtained in Synthesis Example 1 in PGMEA solvent at room temperature (range of 23-27°C) was measured (solvent PGMEA, 25±2°C). The results are shown in Table 1.

[0124] 5.0 g of a 25% by mass DMF-PGMEA mixed solution of a copolymer of methacrylic acid, acrylic acid ester, and styrene, and 20 mg of compound (A-5) obtained in Synthesis Example 1 were placed in a sample bottle and stirred for 30 minutes. 1 g of the resulting colored resin solution was coated onto a 5 cm × 5 cm glass substrate (spin coating method, 1000 rpm - 6 seconds) and heated at 100°C for 2 minutes to form a film. The color value of the obtained film was measured using a spectrophotometer (Konica Minolta, Inc., CM-5). Subsequently, the film was heated twice at 230°C for 20 minutes each time, and the color value was measured again in the same manner. The color difference (ΔE) of the color values ​​before and after heating at 230°C was measured. * ab The heat resistance index was used, and the results are shown in Table 1.

[0125] [Examples 2-4] Except for using compounds (A-11), (A-19), and (A-20) obtained in Synthesis Examples 2-4 instead of (A-5) as the compounds, the solubility (mass%) in the PGMEA solvent at room temperature (solvent PGMEA, 25±2℃) was measured in the same manner as in Example 1, and the color difference (ΔE) of the color values ​​before and after heating of the formed film at 230℃ was measured. * ab The following were measured and evaluated. The results are summarized in Table 1.

[0126] [Comparative Example 1 and Comparative Example 2] Except for using compound (B-1), which is a dye compound not belonging to the present invention and obtained in Synthesis Example 5, and CI Solvent Yellow 33, a conventional dye compound represented by the following formula (B-2), as compounds instead of (A-5), the solubility (mass%) in PGMEA solvent at room temperature (solvent PGMEA, 25±2℃) was measured in the same manner as in Example 1. In addition, the color difference (ΔE) of the color values ​​of the prepared film before and after heating at 230℃ was measured. * abThe following were measured and evaluated. The results are summarized in Table 1.

[0127] [ka]

[0128] [Table 1]

[0129] As shown in Table 1, the compounds of the examples of the present invention exhibit high solubility in PGMEA and high heat resistance during film formation. Therefore, the colored compositions containing the compounds of the present invention are practically suitable as colorants for color filters. Furthermore, they have higher heat resistance during film formation than the comparative examples, making them excellent as colorants for color filters. [Industrial applicability]

[0130] The colored composition containing the compound (yellow compound) according to the present invention has excellent solubility in organic solvents (such as PGMEA) and excellent heat resistance during film formation, making it useful as a dye material for various applications such as colorants for color filters.

Claims

1. A compound represented by the following general formula (1). 【Chemistry 1】 [In equation (1), Q is a base that is independently represented by the following general equation (2), n is 2, L represents a linear or branched alkylene group having 1 to 25 carbon atoms, which may have substituents. 【Chemistry 2】 [In formula (2), R １ ~R ９ Each of them operates independently. Hydrogen atom, hydroxyl group, halogen atom, cyano group, nitro group, A substituted amino group, Linear, branched, or cyclic alkyl groups having 1 to 25 carbon atoms, which may have substituents. A linear, branched, or cyclic alkenyl group having 2 to 25 carbon atoms, which may have substituents. A linear, branched, or cyclic alkoxy group having 1 to 25 carbon atoms, which may have substituents. A group represented by -(C=O)-R 101 (where R 101 is -H, -CH3, -CH2CH2CH3, -CH=CH2, -C6H5, -NH2, -NHCH3, -NHCH2CH3, dimethylamino group, diethylamino group, di(n-propyl)amino group, or di(n-butyl)amino group), or This represents an aromatic hydrocarbon group having 6 to 25 carbon atoms, which may have substituents. R １ ~R ９ These groups may be bonded to each other to form a ring. Z represents an amino group having an acyl group with 1 to 20 carbon atoms as a substituent. Multiple Qs are assumed to be connected to each other via L.

2. In the above general formula (2), R １ ~R ９ hydrogen atoms, halogen atoms, Linear or branched alkyl groups having 1 to 20 carbon atoms, which may have substituents. A linear alkenyl group having 2 to 20 carbon atoms, which may have substituents, or —(C=O)—R 101 (where R 101 is a group represented as —NH2, —NHCH3, —NHCH2CH3, dimethylamino group, diethylamino group, di(n-propyl)amino group, or di(n-butyl)amino group) The compound according to claim 1.

3. The compound according to claim 1, wherein the compound represented by the general formula (1) is any of the following structural formulas. 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】

4. The solubility in propylene glycol monomethyl ether acetate (PGMEA) at 23-27°C is 1% by mass or more. A colored composition containing the compound described in any one of claims 1 to 3.

5. Using a coating film containing the aforementioned compound, The color difference (ΔE) of the color values ​​before and after heating at 220-240°C. ＊ ａｂ ) is 3.5 or less. A colored composition containing the compound described in any one of claims 1 to 3.

6. A coloring agent for color filters containing a compound according to any one of claims 1 to 3, or a coloring composition according to claim 4 or claim 5.

7. A color filter using the coloring agent for color filters described in claim 6.

Images