JP2022140287A - Yellowish compound, coloring composition containing that compound, collar filter colorant, and collar filter - Google Patents

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 The present invention relates to a yellow compound, a coloring composition containing the compound, a colorant for color filters containing the coloring composition, and a color filter using the coloring composition.

So far, various pigments such as quinophthalone pigments, azo pigments and diketopyrrolopyrrole pigments have been developed (Patent Documents 1 to 4). These pigments are used as colorants for color filters of liquid crystal and electroluminescence (EL) display devices. A color filter is produced by laminating a colored layer on a translucent substrate such as glass by a dyeing method, a pigment dispersion method, a printing method, an electrodeposition method, or the like. A quinophthalone pigment is a yellow compound synthesized by condensation of quinaldine and phthalic anhydride, and is used as a colorant for color filters because of its vividness (Patent Documents 1, 2, 5, 6, Non-Patent Document 1). . However, as the image quality of displays increases, the performance required for color filters increases, and it is necessary to further improve the coloring power, brightness and contrast.

Since pigments are generally insoluble in solvents, they exist in the form of fine particles in color filters containing resins and the like. Therefore, in color filters using pigments, the transmitted light is reflected and scattered on the surface of the pigment particles, which affects the transparency and color purity. is known to decrease.

In order to solve the problem of the decrease in contrast ratio, a method using only a dye as a coloring agent or a method using both a dye and a pigment has been proposed. Since dyes are soluble in solvents, color filters using dyes have less depolarization than pigments alone, and have excellent spectral characteristics, improving contrast and brightness. Expected.

Japanese Patent Publication No. 47-3476 JP 2012-193318 A Japanese Unexamined Patent Application Publication No. 2012-12498 Japanese Patent Application Laid-Open No. 2001-220520 JP 2019-104897 A JP 2019-123856 A

Supervised by Kunihiro Ichimura, "Advanced Color Filter Process Technology and Chemicals", CMC Publishing Co., Ltd., 2006, p. 80

The present invention has been made to solve the above problems, and improves the solubility and heat resistance of a yellow compound in an organic solvent (propylene glycol monomethyl ether acetate (PGMEA), etc.), contains the compound, An object of the present invention is to provide a coloring composition excellent in color properties such as tinting strength, vividness and hue, a coloring agent for color filters containing the coloring composition, and a color filter using the coloring agent.

The present invention was obtained as a result of intensive research for the above object, and has the following gist.

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

[In the formula (1), each Q is independently a group represented by the following general formula (2),
n represents an integer from 2 to 10,
L represents a divalent to decavalent group. ]

[In formula (2), R ¹ to R ⁹ are each independently
hydrogen atom (--H), hydroxyl group (--OH), halogen atom, cyano group (--CN), nitro group (--NO ₂ ),
an optionally substituted amino group having 0 to 25 carbon atoms,
an optionally substituted sulfonyl group having 0 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkyl group having 1 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms,
an optionally substituted acyl group having 1 to 25 carbon atoms,
an optionally substituted ether group having 0 to 25 carbon atoms,
represents an optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or an optionally substituted heterocyclic group having 5 to 25 ring atoms,
Adjacent groups of R ¹ to R ⁹ may combine with each other to form a ring.
Z is each independently a divalent group or a trivalent group,
an optionally substituted amino group having 0 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkylene group having 1 to 25 carbon atoms,
represents a group containing one or more of an ether group or a single bond,
It is assumed that multiple Q's are connected to each other via L's or Z's. ]

2. In the general formula (1), L is an optionally substituted amino group having 0 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkylene group having 1 to 25 carbon atoms,
an optionally substituted ether group having 0 to 25 carbon atoms,
A compound which is an optionally substituted aromatic hydrocarbon group of 6 to 25 carbon atoms or a heterocyclic group of optionally substituted ring atoms of 5 to 25 atoms.

3. A compound in which Z is an optionally substituted amino group having 1 to 20 carbon atoms in the general formula (2).

4. In the general formula (2), R ¹ to R ⁹ are hydrogen atoms, halogen atoms,
an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms,
A compound that is an optionally substituted linear alkenyl group having 2 to 20 carbon atoms or an optionally substituted acyl group having 1 to 20 carbon atoms.

5. A colored composition containing the compound, which has a solubility in propylene glycol monomethyl ether acetate (PGMEA) at 23 to 27° C. of 1% by mass or more.

6. Using a coating film containing the compound,
The color difference (ΔE ^* _ab ) in the color values before and after heating at 220 to 240°C is 3.5 or less.
A coloring composition containing the compound.

7. A coloring agent for a color filter containing the above compound or coloring composition.

8. A color filter using the colorant for a color filter.

The compound according to the present invention has excellent solubility in organic solvents such as PGMEA as compared with conventional yellow compounds, and has excellent heat resistance during film formation. Therefore, the compound according to the present invention The coloring composition containing is useful as a colorant for color filters.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, embodiments of the present invention will be described in detail. It should be noted that the present invention is not limited to the following embodiments, and various modifications can be made within the scope of the gist of the present invention. First, the compound represented by the general formula (1) will be described.

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), n represents an integer of 2 to 10, and L represents a divalent to 10 valent group. A plurality of Q may be the same or different.

Therefore, the general formula (1) can be expressed as the following general formula (1-2) using the general formula (2).

Here, in the general formula (1), when n is 2, when a plurality of Qs are expressed as Q ¹ and Q ² , respectively, Q ¹ and Q ² through L as shown in the following formula (1-3) are connected like "Q ¹ -L-Q ² ".

Furthermore, in the general formula (1), when n is 3, when a plurality of Qs are represented by Q ¹ , Q ² and Q ³ respectively, Q ¹ to Q ³ may be bonded, and each of Q ¹ to Q ³ may be directly bonded to each other or may be exchanged with each other. Similarly, when n is 4 or more, multiple Qs can be bonded to each other through L as in the following formula (1-4).

Thus, in the general formula (1), n represents an integer of 2 to 10, and even when Q ¹ to Q ¹⁰ exist as a plurality of Q, each of Q ¹ to Q ¹⁰ is through L Each of Q ¹ to Q ¹⁰ may be directly bonded to each other, or may be exchanged with each other. Accordingly, L represents a group with a valence of 2 to 10 corresponding to n. n is preferably 2-6, more preferably 2-4.

Examples of the “halogen atom” represented by R ¹ to R ⁹ in general formula (2) include fluorine atom, chlorine atom, bromine atom and iodine atom. As the "halogen atom", a fluorine atom or a chlorine atom is preferred.

In the general formula (2), the “amino group optionally having 0 to 25 carbon atoms” represented by R ¹ to R ⁹ may or may not have a substituent. may include an "amino group having substituents R ¹⁰ and R ¹¹ " represented by "-NR ¹⁰ R ¹¹ " when having a substituent, an unsubstituted amino group (-NH ₂ ), a monosubstituted amino groups, disubstituted amino groups, and the like. The number of carbon atoms in the monosubstituted amino group or disubstituted amino group is, for example, 1-25, may be 1-20, or may be 2-10. "Amino group having 0 to 25 carbon atoms which may have substituent(s)" refers to "direct chain, branched or cyclic alkyl group", "aromatic hydrocarbon group having 6 to 25 carbon atoms", "acyl group having 0 to 25 carbon atoms", "heterocyclic ring having 5 to 25 ring atoms" It may be a group to which "group" is bonded. The monosubstituted amino group includes ethylamino group, butylamino group, acetylamino group, phenylamino group and the like. Disubstituted amino groups include dialkylamino groups having 2 to 25 carbon atoms such as dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group and dihexylamino group; and 4 to 4 carbon atoms such as diallylamino group. 25 dialkenylamino group; diphenylamino group, N-acetyl-N-phenylamino group, (n-butyl)-N-phenylamino group and the like.

In the general formula (2), the “optionally substituted C0-25 sulfonyl group” represented by R ¹ to R ⁹ is “—SO ₂ —R ¹⁰⁰ ” (or “— S(=O) ₂ -R ¹⁰⁰ '') means a sulfonyl group having a substituent R ¹⁰⁰ . “—SO ₂ —R ¹⁰⁰ ” may be a group containing no carbon atoms, such as “—SO ₃ H” or “—SO ₃ M” containing an alkali metal atom “M”. Alkali metal atom "M" in the present invention includes lithium atom (Li), sodium atom (Na), potassium atom (K) or cesium atom (Cs), preferably Li, Na or K, Li or Na is more preferred, and Na is particularly preferred. The number of carbon atoms in R ¹⁰⁰ is 0-25, may be 1-20, or may be 1-10. The optionally substituted sulfonyl group having 0 to 25 carbon atoms includes -SO ₃ H and -SO ₃ M as well as a sulfonamide group (-S(=O) ₂ -NH ₂ ). , mesyl group, and tosyl group.

In the general formula (2), the number of carbon atoms in the "linear, branched or cyclic alkyl group optionally having 1 to 25 carbon atoms" represented by R ¹ to R ⁹ The linear, branched or cyclic alkyl group of 1 to 25" specifically includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, Linear alkyl groups such as decyl; branched alkyl groups such as isopropyl, isobutyl, s-butyl, t-butyl, isooctyl, and 2-ethylhexyl; cyclopropyl, cyclopentyl, cyclohexyl cyclic alkyl groups (cycloalkyl groups) such as groups, cycloheptyl groups, cyclooctyl groups, cyclononyl groups and cyclodecyl groups, 1-adamantyl groups, 2-adamantyl groups, and the like.

In the general formula (2), the number of carbon atoms in the "linear, branched or cyclic alkenyl group optionally having 2 to 25 carbon atoms" represented by R ¹ to R ⁹ 2 to 25 linear, branched or cyclic alkenyl groups" specifically include vinyl group, 1-propenyl group, allyl group, 1-butenyl group, 2-butenyl group, 1-pentenyl group, 1 - linear or branched alkenyl groups such as hexenyl group, isopropenyl group and isobutenyl group; cyclic alkenyl groups (cycloalkenyl groups) such as cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl group and cycloheptenyl group , or a group in which a plurality of these linear, branched or cyclic alkenyl groups are bonded.

In the general formula (2), the number of carbon atoms in the "linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms which may be substituted" represented by R ¹ to R ⁹ The linear, branched or cyclic alkoxy group of 1 to 25" specifically includes a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group and an octyloxy group. , nonyloxy group, linear alkoxy group such as decyloxy group; isopropoxy group, isobutoxy group, s-butoxy group, t-butoxy group, branched alkoxy group such as isooctyloxy group; cyclopropoxy group, cyclobutoxy group cyclic alkoxy groups (cycloalkoxy groups) such as groups, cyclopentyloxy groups, cyclohexyloxy groups, cycloheptyloxy groups, cyclooctyloxy groups, cyclononyloxy groups, cyclodecyloxy groups; 1-adamantyloxy groups, 2-adamantyl oxy group, and the like.

In general formula (2), the “acyl group optionally having 1 to 25 carbon atoms” represented by R ¹ to R ⁹ is “—(C═O)—R ¹⁰¹ ”. It means a group having the substituent R ¹⁰¹ represented. The substituent R ¹⁰¹ may be a group containing carbon atoms, a group containing nitrogen atoms, or a group containing no carbon atoms. When the substituent R ¹⁰¹ is a group containing carbon atoms, the number of carbon atoms in the substituent R ¹⁰¹ may be, for example, 1-25, or 1-20. When the substituent R ¹⁰¹ is a group containing a nitrogen atom or a group containing no carbon atom, the number of carbon atoms in the substituent R ¹⁰¹ may be, for example, 0 to 25. can be Substituents R ¹⁰¹ include, for example, -H, -CH ₃ , -CH ₂ CH ₂ CH ₃ , -CH=CH ₂ , -C ₆ H ₅ (phenyl group), -NH ₂ , -NHCH ₃ , -NHCH ₂ CH ₃ , a dimethylamino group, ^{a diethylamino} group, a di(n-propyl)amino group, a di(n-butyl)amino group, and the like. It may be the same as the amino group having 0 to 25 carbon atoms which may be present. Specific examples of the "acyl group having 1 to 25 carbon atoms" in the "optionally substituted acyl group having 1 to 25 carbon atoms" include formyl group, acetyl group, propionyl group and acrylyl group. , a benzoyl group, and the like. When "-(C=O)-R ¹⁰¹ " contains a nitrogen atom, it may be an amide group, a primary amide group, or a secondary amide group, and R ¹⁰¹ is represented by R ¹ to R ⁹ above. It may be a monosubstituted amino group or a disubstituted amino group represented by "—NR ¹⁰ R ¹¹ " exemplified in the above "substituted amino group having 0 to 25 carbon atoms".

In the general formula (2), the “ether group having 0 to 25 carbon atoms which may be substituted” represented by R ¹ to R ⁹ is substituted by “—O—R ¹⁰² ”. It means an ether group with the group ^R102 . The substituent R ¹⁰² may be a group containing carbon atoms or a group containing no carbon atoms. Specific examples of the "ether group having 0 to 25 carbon atoms" in the "ether group having 0 to 25 carbon atoms which may have a substituent" include an aminooxy group, "-O-(C= O)—R” (R is any alkyl group, aromatic hydrocarbon group, etc.), phosphoric acid group, phosphoric acid ester group, and the like.

In the general formula (2), the "aromatic hydrocarbon group having 6 to 25 carbon atoms which may have a substituent" represented by R ¹ to R ⁹ Specific examples of "hydrocarbon group" include phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group (anthryl group), phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, An aromatic hydrocarbon group such as a triphenylenyl group (the "aromatic hydrocarbon group" in the present invention includes an aryl group or a condensed polycyclic aromatic group).

In the general formula (2), the "heterocyclic group having 5 to 25 ring-forming atoms which may be substituted" represented by R ¹ to R ⁹ "group" specifically includes pyridyl group, pyrimidinyl group, triazinyl group, imidazolyl group, pyrazolyl group, triazolyl group, thienyl group, furyl group (furanyl group), pyrrolyl group, quinolyl group, isoquinolyl group, naphthyridinyl group, indolyl 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, dibenzofuran Heterocyclic groups (or heteroaromatic hydrocarbon groups) such as a nyl group, a dibenzothienyl group, and a carbolinyl group can be mentioned.

In the general formula (2), "substituted amino group having 0 to 25 carbon atoms" represented by R ¹ to R ⁹ ,
"substituted sulfonyl group having 0 to 25 carbon atoms",
"a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms having a substituent",
"a linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms having a substituent",
"a linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms having a substituent",
"acyl group having 1 to 25 carbon atoms having a substituent",
"a substituted ether group having 0 to 25 carbon atoms",
"Aromatic hydrocarbon group having 6 to 25 carbon atoms having a substituent", or
As the "substituent" in the "heterocyclic group having 5 to 25 ring-forming atoms having a substituent",
Specifically, a deuterium atom, a hydroxyl group, a thiol group, a cyano group, a nitro group;
Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
an amino group having 0 to 20 carbon atoms;
a sulfonyl group having 0 to 20 carbon atoms;
linear, branched or cyclic alkyl group having 1 to 20 carbon atoms;
linear, branched or cyclic alkenyl groups having 2 to 20 carbon atoms;
a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms;
an acyl group having 1 to 20 carbon atoms;
an ether group having 1 to 20 carbon atoms;
an aromatic hydrocarbon group or condensed polycyclic aromatic group having 6 to 20 carbon atoms;
a heterocyclic group having 5 to 20 ring-forming atoms; When the "substituent" contains carbon atoms, the carbon atoms are not included in the above "0 to 25 carbon atoms", "1 to 25 carbon atoms", and "6 to 25 carbon atoms". Only one of these "substituents" may be included, or a plurality of them may be included, and when a plurality of "substituents" are included, they may be the same or different. Moreover, these "substituents" may further have the substituents exemplified above. Further, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom (-O-) or a sulfur atom (-S-) to form a ring. However, the maximum number of "substituents" in each group represented by R ¹ to R ⁹ is 10, and the maximum number of carbon atoms in each group is 100.

In addition, in each of the above groups having a "substituent" represented by R ¹ to R ⁹ in the general formula (2), the "substituent" is
"Amino group having 0 to 20 carbon atoms",
"a sulfonyl group having 0 to 20 carbon atoms",
"linear, branched or cyclic alkyl group having 1 to 20 carbon atoms",
"a linear, branched or cyclic alkenyl group having 2 to 20 carbon atoms",
"a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms",
"acyl group having 1 to 20 carbon atoms",
"Ether group having 1 to 20 carbon atoms",
As the "aromatic hydrocarbon group or condensed polycyclic aromatic group having 6 to 20 carbon atoms" or "heterocyclic group having 5 to 20 ring atoms", specifically,
Amino group; linear or carbon having 1 to 20 carbon atoms, such as methylamino group, dimethylamino group, diethylamino group, ethylmethylamino group, dipropylamino group, di-t-butylamino group, diphenylamino group a branched alkyl group having 3 to 20 atoms, or a monosubstituted or disubstituted amino group having an aromatic hydrocarbon group having 6 to 20 carbon atoms;
A group having a sulfonyl group (-S(=O) ₂ -) having 0 to 20 carbon atoms such as a sulfonamide group (-S(=O) ₂ -NH ₂ ), a mesyl group and a tosyl group; -SO ₃ ^- , —SO ₃ H, —SO ₃ M (M is an alkali metal atom);
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, linear or branched alkyl groups having 3 to 20 carbon atoms such as heptyl group, octyl group, isooctyl group, nonyl group and decyl group; cyclopropyl group, cyclopentyl group, cyclohexyl group; Cyclic alkyl groups (cycloalkyl groups) having 3 to 20 carbon atoms such as cyclooctyl group, cyclononyl group, 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 the number of carbon atoms in which multiple of these alkenyl groups are bonded linear or branched alkenyl group having 2 to 20 carbon atoms or branched chain having 3 to 20 carbon atoms; cyclic alkenyl having 3 to 20 carbon atoms such as cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group; group (cycloalkenyl group);
methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, isopropoxy group, isobutoxy group, s-butoxy group, t-butoxy group A linear or branched alkoxy group having 3 to 20 carbon atoms such as isooctyloxy group; cyclopropoxy group, cyclobutoxy group, cyclopentyloxy group, cyclohexyloxy group, cyclononyloxy cyclic alkoxy group (cycloalkoxy group) having 3 to 20 carbon atoms such as group, cyclodecyloxy group; 1-adamantyloxy group, 2-adamantyloxy group;
acyl groups having 1 to 20 carbon atoms such as formyl group, acetyl group, propionyl group, acrylyl group and benzoyl group;
ether group (-O-), aminooxy group, ester group represented by "-O-(C=O)-R" (R is any alkyl group or aromatic hydrocarbon group, etc.), phosphate group, A group containing an ether group (-O-) having 0 to 20 carbon atoms such as a phosphate group;
phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group (anthryl group), phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, etc., having 6 to 20 carbon atoms; aromatic hydrocarbon group or condensed polycyclic aromatic group;
pyridyl group, pyrimidylinyl group, triazinyl group, thienyl group, furyl group (furanyl group), pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, quinolyl group, isoquinolyl group, naphthyridinyl group, acridinyl group, phenanthrolinyl group, benzofuranyl benzothienyl group, oxazolyl group, indolyl group, carbazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group, etc. a heterocyclic group having 5 to 20 atoms;
an aryloxy group having 6 to 19 carbon atoms such as a phenyloxy group, a tolyloxy group, a biphenylyloxy group, a naphthyloxy group, anthracenyloxy group and a phenanthrenyloxy group;

In general formula (2), adjacent groups of R ¹ to R ⁹ may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. .

In general formula (2), R ¹ to R ⁹ are
hydrogen atom, hydroxyl group, halogen atom, nitro group, cyano group,
an optionally substituted amino group having 1 to 20 carbon atoms,
an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms and having 3 to 20 carbon atoms,
an optionally substituted linear or branched alkenyl group having 2 to 20 carbon atoms and having 3 to 20 carbon atoms,
an optionally substituted linear or branched alkoxy group having 2 to 20 carbon atoms and having 3 to 20 carbon atoms,
an optionally substituted acyl group having 1 to 20 carbon atoms,
An optionally substituted ether group having 1 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms is preferable,
hydrogen atom, halogen atom,
an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms,
an optionally substituted linear alkenyl group having 2 to 20 carbon atoms, or
An optionally substituted acyl group having 1 to 20 carbon atoms is more preferable.
R ⁷ or R ⁸ is a hydrogen atom, an optionally substituted linear or branched C 1 to 20 alkyl group, or an optionally substituted C 2 to 20 linear alkenyl groups or optionally substituted acyl groups having 1 to 20 carbon atoms are more preferred, and R ⁶ or R ⁹ is a hydrogen atom or a halogen atom is more preferred.

In general formula (1), n Qs represented by general formula (2) are included. A plurality of (n) Z's in the general formula (2) may be independently the same or different and are a divalent group or a trivalent group.

In general formula (1), multiple Q's are bound to each other via L's or Z's. When Z is a divalent group, for example, when the general formula (1) is expressed as "Q ¹ -L-Q ² " as in the general formula (1-3), the following formula (2- 1). At this time, a plurality of R ¹ to R ⁹ may be independently the same or different. Further, when represented by the following formula (2-1), any one or more of a plurality of Z may be a trivalent group, and Z may be a suitable group such as R ¹⁰ or R ¹¹ . It may be a trivalent group having a trivalent group, and specifically, it may be represented by the following formula (2-2).

In the general formula (1), when a plurality of Q are bonded through Z, each Q is represented by Z through a divalent group or a trivalent group, as in the following formula (2-3) can be combined with each other.

In the general formula (1), the group represented by "L" represents a divalent to decavalent group, and specific examples of L are divalent to decavalent groups using any of the following groups. I can give you something. In addition, L and multiple Qs can be bonded to each other at any substituent site of the groups below.
These groups include:
"optionally substituted amino group having 0 to 25 carbon atoms" (or imino group),
"optionally substituted sulfonyl group having 0 to 25 carbon atoms",
"an optionally substituted linear, branched or cyclic alkyl group having 1 to 25 carbon atoms",
"an optionally substituted linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms",
"an optionally substituted linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms",
"optionally substituted acyl group having 1 to 25 carbon atoms",
"an optionally substituted ether group having 0 to 25 carbon atoms",
"Optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms" or "Heterocyclic group having 5 to 25 ring atoms optionally having substituents" can be mentioned. .
Specific examples of these groups are the same as those exemplified for R ¹ to R ⁹ in formula (2). The “substituents” that these “groups” may have are the same as the “substituents” that the groups represented by R ¹ to R ⁹ may have.
L represented by these groups is the number of Q (n), or a group with any valence of 2 to 10 by bonding with multiple Q at a site optionally having a substituent can be For example, "an optionally substituted linear, branched or cyclic alkyl group having 1 to 25 carbon atoms" means "an optionally substituted straight chain having 1 to 25 carbon atoms A trivalent or more valent group may be formed by bonding a substituent to a part of these "alkylene groups". Only one of these "groups" or "substituents" may be included, or a plurality of them may be included, and when a plurality of "groups" or "substituents" are included, they may be the same or different. In addition, these "groups" or "substituents" may further have the above-exemplified groups or substituents. These "groups" or "substituents" may be bonded 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 number of the above "groups" or "substituents" contained in L shall be 10 at maximum, and the maximum number of carbon atoms in each group shall be 100.

In the general formula (1), L represents a divalent to decavalent group, any of "an optionally substituted linear, branched or cyclic alkyl group having 1 to 25 carbon atoms" If it is a group that can be bonded to each other at the substituent site, L is "an optionally substituted linear, branched or cyclic alkylene group having 1 to 25 carbon atoms" expressed. Specifically, methylene group, ethylene group, —CHCH ₃ —, 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, n-hexylene group (hexane-1,6-diyl group, —C ₆ H _12- ), linear or branched alkylene groups such as n-heptylene group, n-octylene group, n-nonylene group, n-decylene group, or cyclopropylene group, cyclopentylene group, cyclohexylene group, etc. A cyclic alkylene group of or the like is exemplified, but not limited to these.

In general formula (1), L is
an optionally substituted amino group having 0 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkylene group having 1 to 25 carbon atoms,
an optionally substituted ether group having 0 to 25 carbon atoms,
An optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or an optionally substituted heterocyclic group having 5 to 25 ring atoms, is preferable.
An optionally substituted linear or branched alkylene group having 1 to 25 carbon atoms is more preferred.

In the general formula (2), the divalent group or trivalent group represented by Z is
an optionally substituted amino group having 0 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkylene group having 1 to 25 carbon atoms,
It represents a group containing one or more types of ether groups or single bonds, and includes those in which these groups are replaced with divalent or trivalent groups at appropriate sites. These amino groups, alkylene groups or ether groups may be the same or different.

In Z in the general formula (2), the "amino group having 0 to 25 carbon atoms" in the "amino group having 0 to 25 carbon atoms which may have a substituent" includes -N <, -N ═CH—, or a group similar to “an optionally substituted amino group having 0 to 25 carbon atoms” represented by R ¹ to R ⁹ in the general formula (2) is substituted by any Examples include those in which a divalent group or a trivalent group is substituted at the site of the group, and the substituent R ¹² represents -NR ¹² -, >N-R ¹² -, -R ¹² -NR ¹² -R ¹² -, -R It can be represented as ¹² -NH-NR ¹² -R ¹² -. Examples of the substituent R ¹² include those similar to the “substituent” in the “amino group optionally having 0 to 25 carbon atoms” represented by R ¹ to R ⁹ . Plural R ¹² may be the same or different. In the general formula (2), when Z contains a plurality of "optionally substituted amino groups having 0 to 25 carbon atoms", each Q is bonded to a different Q through Z. be able to.

In the general formula (2), the "linear, branched or cyclic alkylene group optionally having 1 to 25 carbon atoms" represented by Z includes R ¹ to R ⁹ Divalent in a substituent at any position from a monovalent group having the same structure as the represented "optionally substituted linear, branched or cyclic alkyl group having 1 to 25 carbon atoms" I can give you what I changed to the base. Specifically, it is the same as the "optionally substituted linear, branched or cyclic alkylene group having 1 to 25 carbon atoms" represented by L. good too. As the “substituent” in the “optionally substituted linear, branched or cyclic alkylene group having 1 to 25 carbon atoms”, the “substituent” represented by R ¹ to R ⁹ The same as the “substituent” in “optionally having linear, branched or cyclic alkyl group having 1 to 25 carbon atoms” can be mentioned. These alkylene groups may be branched to form a trivalent group.

In the general formula (2), Z is a divalent group or a trivalent group, an amino group having 1 to 20 carbon atoms which may have a substituent, a carbon which may have a substituent A linear, branched or cyclic alkylene group having 1 to 20 atoms, or a group containing an ether group is preferable, and an optionally substituted amino group having 1 to 20 carbon atoms. It is more preferable to have

In addition, in the above,
A "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms" is preferably a "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or a branched or cyclic alkyl group having 3 to 25 carbon atoms. "alkyl group".
A "linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms" is preferably a "linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms, or a branched or cyclic group having 3 to 25 carbon atoms. alkenyl group”.
A "linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms" is preferably a "linear, branched or cyclic group having 1 to 25 carbon atoms, or a branched or cyclic group having 3 to 25 carbon atoms. alkoxy group”.
A "linear, branched or cyclic alkylene group having 1 to 25 carbon atoms" is preferably a "linear, branched or cyclic group having 1 to 25 carbon atoms, or a branched or cyclic group having 3 to 25 carbon atoms. alkylene group”.

The compounds of the present invention are
One divalent to decavalent group L [synonymous with L in the general formula (1). ],
n identical or different monovalent groups R ⁰ represented by the following general formula (3),
n identical or different monovalent groups R ¹² [same as the substituent in the general formula (2) or a hydrogen atom; ],
and n identical or different divalent or trivalent groups Z [synonymous with Z in the general formula (2). ]
consists of
n represents an integer from 2 to 10,
L is only bonded to Z,
R ⁰ is only attached to Z,
R ¹² is only attached to Z,
Z is a compound bound to R ⁰ and bound to one or two selected from the group consisting of L, R ¹² and other Z.

［式（３）中、Ｒ^１～Ｒ^９は上記と同義である。］

[In Formula (3), R ¹ to R ⁹ have the same definitions as above. ]

The compound represented by general formula (1) (hereinafter simply compound (1)) includes all possible stereoisomers and tautomers. Specific examples of compound (1) are shown below, but the present invention is not limited thereto. Note that hydrogen atoms are partially omitted in the following structural formulas.

The compound represented by general formula (1) can be synthesized by the following method. Synthesis examples in which n is 2, Z is an amino group having an optional substituent R ¹⁰ , and L is —C ₆ H ₁₂ — in general formula (1) are shown below.
By reacting an 8-amino-2-methylquinoline derivative having a corresponding substituent with 1,6-diiodohexane under a suitable solvent and temperature, the following intermediate having a corresponding substituent (X- 1) is obtained.

Furthermore, the obtained intermediate (X-1) and a trimellitic anhydride having a corresponding substituent are subjected to a dehydration condensation reaction using a suitable solvent and temperature to obtain a compound represented by the general formula (1). Compounds of the invention can be obtained.

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, or the like; recrystallization or crystallization using a solvent; In addition, for the identification and analysis of these compounds, nuclear magnetic resonance spectroscopy (NMR), absorbance measurement with a spectrophotometer, ultraviolet-visible absorption spectrum (UV-Vis) measurement, thermogravimetry-differential thermal analysis (TG-DTA) etc. can be done. These analytical methods can also be used to evaluate the solubility, color and heat resistance of the obtained compounds.

The solubility of the compound of the present invention is represented by the solubility, and the solubility represents the maximum amount of the substance that can be dissolved in a specific solvent, such as "mass% (solvent name, temperature)" etc. expressed in units of Solubility can be obtained, for example, by mixing a sample in a specific solvent, stirring the solvent at a constant temperature for a certain period of time, and measuring the concentration of the prepared saturated solution. It can also be obtained by concentration measurement, such as by measurement.

By performing thermogravimetry-differential thermal analysis (TG-DTA) of the compound of the present invention, the thermal decomposition temperature can be analyzed and used as an index of heat resistance. In the coloring composition, the thermal decomposition temperature of the compound in the pigment portion is preferably 250°C or higher. When applied to color filters, the higher the thermal decomposition temperature, the better.

The compound of the present invention is mixed with various resin solutions used for colorants for color filters such as acrylic resin, applied on a glass substrate by a method such as spin coating, and dried by heating to prepare a coating film. can. Color properties of the obtained coating film can be evaluated by performing colorimetry using a spectrophotometer and obtaining a color value of the coating film. For color values, the CIE L ^* a ^* b ^* color system and the like are generally used. Specifically, the color values L ^* , a ^* , and b ^* of the film sample are measured, and the heat resistance can be judged from the color difference (ΔE ^* _ab ) between the color values before and after heating at an appropriate temperature. When applied to color filters, the color difference at a temperature of around 230° C. (for example, within the range of 220 to 240° C.) can be used as an index of heat resistance. It is preferable that the value of ΔE ^* _ab is smaller than that of the comparative object, which means less color change due to thermal decomposition. ΔE ^* _ab is preferably 3.5 or less, more preferably 3 or less. A coloring composition and a coloring agent for a color filter having excellent color properties such as coloring power, vividness, and hue can be obtained with a coloring compound that undergoes little discoloration due to thermal decomposition.

In the coloring composition contained in the colorant for color filters, the coloring compound must be well dissolved or dispersed in the resin and the organic solvent. High solubility is preferred. Specific examples of the organic solvent 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) and the like; aromatic hydrocarbons such as benzene, toluene and xylene; N,N-dimethylformamide (DMF), N-methyl amides such as pyrrolidone (NMP); dimethylsulfoxide (DMSO); These solvents may be used alone or in combination of two or more. Among these, the compound according to the present invention has excellent solubility in PGME and PGMEA, for example, the solubility (% by mass) in PGMEA at room temperature in the temperature range of 25 ± 2 ° C. (temperature within the range of 23 to 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.

The compound represented by the general formula (1) preferably has a maximum absorption wavelength in the visible light region, eg, 350 to 700 nm, in the range of 400 to 500 nm in solution.

The coloring composition of the present invention contains the compound of the present invention represented by the general formula (1), may contain a compound of one type of structure, contains a compound of two or more types of structure You may have In the present invention, the compound preferably has one type of structure.

In order to enhance the performance as a colorant for color filters, the coloring composition of the present invention contains surfactants, dispersants, antifoaming agents, leveling agents, and other colorants for color filters as other components of the compound. Additives and the like that are mixed during production can be added. However, it is preferable that the content of these additives in the coloring composition is an appropriate amount, and the content does not reduce the solubility of the coloring composition, or improve it more than necessary, and does not affect the production of color filters. is preferably These additives can be added at any time during preparation of the coloring composition.

The colorant for color filters of the present invention comprises a coloring composition containing a compound represented by formula (1) and components generally used for producing color filters. For example, in the case of a method using a photolithography process, a general color filter is a liquid prepared by mixing dyes such as dyes and pigments with resin components (including monomers, oligomers, binder components, and resist components) and solvents. is coated on a substrate such as glass or resin, photopolymerized using a photomask, a colored pattern of a solvent-soluble/insoluble dye-resin composite film is prepared, washed, and then heated. be done. Since the compound of the present invention has excellent solubility, it has excellent dispersibility with materials used in the production of these color filters. can be evaluated. Also in the electrodeposition method and the printing method, a colored pattern can be produced by using a mixture of a pigment and a resin or other components. Accordingly, specific components in the colorant for color filters of the present invention include compounds represented by the general formula (1), other dyes such as dyes and pigments, resin components, organic solvents, photopolymerization initiators, and the like. Other additives can be mentioned. Also, these components may be selected, or other components may be added as necessary.

When the coloring composition of the present invention is used as a colorant for color filters, it can be used as a yellow color filter, but it can also be used by mixing it with color filters for other colors such as red and green. In addition, the coloring composition of the present invention may be used alone, or may be mixed with other known dyes or pigments to adjust the color tone. For example, basic dyes; acid dyes; disperse dyes; spirone dyes; Methane-based, indanthrene-based, oxazine-based, dioxazine-based, naphthol AS-based, benzimidazolone-based, pyrazolone-based, perylene-based, perinone-based, quinacridone-based, isoindolinone-based, xanthene-based, diketopyrrolopyrrole-based, etc. and dyes or pigments.

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

As the resin component in the coloring composition and the colorant for color filters of the present invention, known components can be used as long as they have properties necessary for the production method and use of the color filter resin film formed by using these components. can be used. Examples include acrylic resins, olefin resins, styrene resins, polyimide resins, urethane resins, polyester resins, epoxy resins, vinyl ether resins, phenol (novolak) resins, other transparent resins, photocurable resins, thermosetting resins, binder resins, Photoresist resins can be mentioned, and these can be used in appropriate combination. Copolymers of these resins can also be used in combination. The content of the resin in these colorant for color filters is preferably 5 to 95% by mass, more preferably 10 to 50% by mass, in the case of a liquid colorant.

Other additives in the coloring composition and the colorant for color filters of the present invention include components necessary for polymerization and curing of resins such as photopolymerization initiators and cross-linking agents. Surfactants, dispersants, and the like necessary for stabilizing the properties of the components in the agent are included. Any of these can use known ones 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, more preferably 10 to 40% by mass.

Hereinafter, embodiments of the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples. In Synthesis Examples, compounds were identified by ¹ H-NMR analysis (nuclear magnetic resonance apparatus, Ascend ^TM 400, manufactured by Bruker).

[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 reactor and cooled to 5°C or less in an ice bath. 82.8 g of 2,4,6-trimethylbenzoyl chloride was gradually added and stirred at 25° C. for 7 hours. Water was added to the reaction solution and extracted with dichloromethane. The extract was concentrated under reduced pressure and purified by column chromatography (carrier: silica gel, solvent: heptane/dichloromethane/ethyl acetate=10/3/1 (volume ratio)). Heptane was added to the reaction solution and filtered to obtain N-(2,4,6-trimethylbenzoyl)-8-aminoquinaldine (70.8 g, yield 77%).
Subsequently, 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 5° C. or lower in an ice bath. In another 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. The solution in the reaction vessel 2 was gradually dropped into the 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 solution, 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 (carrier: silica gel, solvent: dichloromethane/heptane=1/1 (volume ratio)) to obtain the following intermediate (100) (68.8 g, yield 100 %).

Subsequently, 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 heated at 180°C. Stirred for 8 hours. After cooling to 25° C., 680 mL of toluene was added to the reaction solution and filtered to obtain the following intermediate (101) (95.0 g, yield 92%).

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

The obtained yellow powder was subjected to NMR measurement, the following 88 hydrogen signals were detected, and the structure was identified as the compound represented by the formula (A-5).

¹ H-NMR (400 MHz, CDCl ₃ ): 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).

[Synthesis Example 2] Synthesis of compound (A-11) 8.6 g of sodium hydride (60%, dispersed in liquid paraffin) and 160 mL of dehydrated DMF were placed in reaction vessel 1, and cooled to 5°C or less in an ice bath. In another 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. The solution in the reaction vessel 2 was gradually dropped into the 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 solution, 320 mL of water was gradually added dropwise, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure and purified by column chromatography (carrier: silica gel, solvent: dichloromethane/heptane=1/1 (volume ratio)) to obtain the following intermediate (102) (30.7 g, yield 82 %).

Subsequently, 30.7 g of the intermediate (102) obtained above, 24.4 g of 2,3-naphthalenedicarboxylic 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., purification by column chromatography (carrier: silica gel, solvent: dichloromethane/acetone=10/1 (volume ratio)) gave a yellow powder (7.7 g, yield 17%).

The resulting yellow powder was subjected to NMR measurement, the following 66 hydrogen signals were detected, and the structure was identified as the compound represented by the following formula (A-11).

¹ H-NMR (400 MHz, CDCl ₃ ): 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).

[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, and 16.1 g of benzoic acid were added. , 60 mL of 1,2,4-trichlorobenzene was added, and the mixture was stirred at 180° C. for 8 hours. After cooling to 25° C., purification by column chromatography (carrier: silica gel, solvent: dichloromethane/acetone=10/1 (volume ratio)) gave a yellow powder (20.7 g, yield 51%).

The obtained yellow powder was subjected to NMR measurement, the following 60 hydrogen signals were detected, and the structure was identified as the compound represented by the following formula (A-19).

¹ H-NMR (400 MHz, CDCl ₃ ): 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).

[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, and 15.4 g of benzoic acid were added. , and 50 mL of 1,2,4-trichlorobenzene were added and stirred at 180° C. for 8 hours. After cooling to 25° C., purification by column chromatography (carrier: silica gel, solvent: dichloromethane/acetone=10/1 (volume ratio)) gave a yellow powder (24.8 g, yield 64%).

The obtained yellow powder was subjected to NMR measurement, the following 58 hydrogen signals were detected, and the structure was identified as the compound represented by the following formula (A-20).

¹ H-NMR (400 MHz, CDCl ₃ ): 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).

[Synthesis Example 5] Synthesis of Comparative Example Compound (B-1) In a reaction vessel, N-(2,4,6-trimethylbenzoyl)-N-propyl- 47.4 g of 8-aminoquinaldine, 17.8 g of 4-methylphthalic anhydride, 13.4 g of benzoic acid and 80 mL of 1,2,4-trichlorobenzene were added and stirred at 180° C. for 8 hours. After cooling to 25° C., it was purified by column chromatography (carrier: silica gel, solvent: heptane/dichloromethane/ethyl acetate=10/3/1 (volume ratio)) to obtain a yellow powder (B-1) (24. 0 g, 36% yield).

The obtained yellow powder was subjected to NMR measurement, the following 30 hydrogen signals were detected, and the structure was identified as the compound represented by the following formula (B-1).

¹ H-NMR (400 MHz, CDCl ₃ ): 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).

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

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 the compound (A-5) obtained in Synthesis Example 1 were placed in a sample bottle and mixed with stirring for 30 minutes. did. 1 g of the resulting colored resin solution was applied 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. Color values of the resulting film were measured using a spectrophotometer (CM-5, manufactured by Konica Minolta, Inc.). After that, heating was performed twice at 230° C. for 20 minutes, and the color values were measured in the same manner. The color difference (ΔE ^* _ab ) between the color values before and after heating at 230° C. was used as an index of heat resistance, and the results are also shown in Table 1.

[Examples 2 to 4]
The same as in Example 1, except that the compounds (A-11), (A-19) and (A-20) obtained in Synthesis Examples 2 to 4 were used instead of (A-5) as compounds. The solubility (mass%) in a PGMEA solvent at room temperature (solvent PGMEA, 25 ± 2 ° C.) was measured by the method of No., and the color difference (ΔE ^* _ab ) of the color value before and after heating at 230 ° C. was measured and evaluated. The results are summarized in Table 1.

[Comparative Example 1 and Comparative Example 2]
As a compound, instead of (A-5), a dye compound not belonging to the present invention, the compound (B-1) obtained in Synthesis Example 5 and the conventional compound represented by the following formula (B-2) C.I. I. Solubility (% by mass) in a PGMEA solvent at room temperature (solvent PGMEA, 25±2° C.) was measured in the same manner as in Example 1, except that Solvent Yellow 33 was used. Moreover, the color difference (ΔE ^* _ab ) in the color value before and after heating at 230° C. was measured and evaluated for the formed film. The results are summarized in Table 1.

As shown in Table 1, the compounds of the examples of the present invention show high solubility in PGMEA and high heat resistance during film formation, and the coloring compositions containing the compounds of the present invention are colored for color filters. There is no practical problem as an agent. In addition, it has higher heat resistance than the comparative examples during film formation, and is excellent as a colorant for color filters.

The coloring composition containing the compound (yellow compound) according to the present invention has excellent solubility in organic solvents (such as PGMEA), and has excellent heat resistance during film formation, for color filters It is useful as a pigment material for various uses such as a coloring agent.

Claims (8)

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

[In the formula (1), each Q is independently a group represented by the following general formula (2),
n represents an integer from 2 to 10,
L represents a divalent to decavalent group. ]

[In formula (2), R ¹ to R ⁹ are each independently
hydrogen atom, hydroxyl group, halogen atom, cyano group, nitro group,
an optionally substituted amino group having 0 to 25 carbon atoms,
an optionally substituted sulfonyl group having 0 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkyl group having 1 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms,
an optionally substituted acyl group having 1 to 25 carbon atoms,
an optionally substituted ether group having 0 to 25 carbon atoms,
represents an optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or an optionally substituted heterocyclic group having 5 to 25 ring atoms,
Adjacent groups of R ¹ to R ⁹ may combine with each other to form a ring.
Z is each independently a divalent group or a trivalent group,
an optionally substituted amino group having 0 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkylene group having 1 to 25 carbon atoms,
represents a group containing one or more of an ether group or a single bond,
It is assumed that multiple Q's are connected to each other via L's or Z's. ] In the general formula (1), L is an optionally substituted amino group having 0 to 25 carbon atoms,
an optionally substituted linear, branched or cyclic alkylene group having 1 to 25 carbon atoms,
an optionally substituted ether group having 0 to 25 carbon atoms,
An optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or an optionally substituted heterocyclic group having 5 to 25 ring atoms, according to claim 1 Compound as described. The compound according to claim 1 or 2, wherein in the general formula (2), Z is an optionally substituted amino group having 1 to 20 carbon atoms. In the general formula (2), R ¹ to R ⁹ are hydrogen atoms, halogen atoms,
an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms,
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,
A compound according to any one of claims 1 to 3. The solubility in propylene glycol monomethyl ether acetate (PGMEA) at 23 to 27 ° C. is 1% by mass or more,
A coloring composition containing the compound according to any one of claims 1 to 4. Using a coating film containing the compound,
The color difference (ΔE ^* _ab ) in the color values before and after heating at 220 to 240°C is 3.5 or less.
A coloring composition containing the compound according to any one of claims 1 to 4. A colorant for a color filter containing the compound according to any one of claims 1 to 4 or the coloring composition according to claim 5 or 6. A color filter using the colorant for color filters according to claim 7 .