CN115073933A

CN115073933A - Yellow compound, colored composition containing the same, colorant for color filter, and color filter

Info

Publication number: CN115073933A
Application number: CN202210176731.6A
Authority: CN
Inventors: 神田大三; 赵周衡
Original assignee: Hodogaya Chemical Co Ltd
Current assignee: Hodogaya Chemical Co Ltd
Priority date: 2021-03-11
Filing date: 2022-02-25
Publication date: 2022-09-20
Also published as: KR20220127740A; JP2022140287A; TW202235419A

Abstract

The invention provides a coloring composition, a coloring agent for a color filter and the color filter, wherein the coloring composition has excellent color characteristics and is improved in solubility and heat resistance of a yellow compound in an organic solvent (such as PGMEA). A compound represented by the following general formula (1),

in the formula (1), Q is a group represented by the formula (2), n is an integer of 2 to 10, and L is a group having a valence of 2 to 10.R ¹ ～R ⁹ Each independently represents H, a hydroxyl group, a halogen atom, an amino group, a sulfonyl group, an alkyl group, an alkenyl group, an alkoxy group, an acyl group, an O-, an aromatic hydrocarbon group, a heterocyclic group or the like, and adjacent groups may be bonded to each other to form a ring. Z is a group having a valence of 2 or 3, respectively, and represents an amino group, an alkylene group, a group containing-O-or a single bond, and Q's are bonded to each other via L or Z.

Description

Yellow compound, colored composition containing the same, colorant for color filter, and color filter

Technical Field

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

Background

Many pigments such as quinophthalone pigments, azo pigments, diketopyrrolopyrrole pigments, and the like have been developed (patent documents 1 to 4). These pigments are used as colorants for color filters of liquid crystal and Electroluminescent (EL) display devices. Color filters are produced by laminating a colored layer on a light-transmitting substrate such as glass by a dyeing method, a pigment dispersion method, a printing method, an electrodeposition method, or the like. Quinophthalone pigments are yellow compounds synthesized by condensation of quinaldine and phthalic anhydride, and are used as colorants for color filters because of their distinctiveness (patent documents 1,2, 5, 6, non-patent document 1). However, as the image quality of displays increases, the performance required of color filters increases, and further improvement in the coloring power, luminance, and contrast is required.

The pigment is usually insoluble in a solvent, and therefore exists in fine particles in a color filter including a resin or the like. Therefore, as for a color filter using a pigment, it is known that: the transmitted light is reflected and scattered on the surface of the pigment particles, and affects transparency and color purity, and the transmitted light has a depolarization effect due to reflection, which lowers the contrast of the color liquid crystal display device.

In order to improve the problem of contrast reduction, a method of using only a dye as a colorant, a method of using a dye and a pigment in combination, or the like has been proposed. Since the dye is soluble in a solvent, a color filter using the dye is expected to have a reduced depolarization effect, superior spectral characteristics, and improved contrast, brightness, and the like, as compared with a color filter using only a pigment as a colorant.

Documents of the prior art

Patent document

Patent document 1: japanese examined patent publication No. 47-3476

Patent document 2: japanese patent laid-open publication No. 2012 and 193318

Patent document 3: japanese laid-open patent publication No. 2012-12498

Patent document 4: japanese patent laid-open No. 2001-220520

Patent document 5: japanese patent laid-open publication No. 2019-104897

Patent document 6: japanese patent laid-open publication No. 2019-123856

Non-patent literature

Non-patent document 1: the "most advanced color Filter Process technology and chemistry", CMCs, 2006, page 80, incorporated by Mac Corp

Disclosure of Invention

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

The present invention has been made as a result of intensive studies for the above-described object, and the gist thereof is as follows.

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

[ CHEM 1 ]

In the formula (1), Q is a group represented by the following general formula (2),

n represents an integer of 2 to 10,

l represents a 2-10 valent group.

[ CHEM 2 ]

In the formula (2), R ¹ ～R ⁹ Each independently represents:

hydrogen atom (-H), hydroxy group(-OH), halogen atom, cyano group (-CN), nitro group (-NO) ₂ )、

An amino group having 0 to 25 carbon atoms which may have a substituent,

A C0-25 sulfonyl group which may have a substituent,

A linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent, a linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms which may have a substituent,

A linear, 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 optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or

A heterocyclic group having 5 to 25 ring-forming atoms and optionally having a substituent,

R ¹ ～R ⁹ can be bonded to each other between adjacent groups to form a ring.

Z is each independently a 2-valent group or a 3-valent group, and represents:

an amino group having 0 to 25 carbon atoms which may have a substituent,

A linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which may have a substituent,

Containing 1 or 2 or more groups among ether groups or single bonds,

q's are bonded to each other via L or Z.

2. A compound represented by the general formula (1) above, wherein L is:

an amino group having 0 to 25 carbon atoms which may have a substituent,

An ether group having 0 to 25 carbon atoms which may have a substituent,

A heterocyclic group having 5 to 25 ring-forming atoms which may have a substituent.

3. A compound represented by the general formula (2), wherein Z is an amino group having 1 to 20 carbon atoms which may have a substituent.

4. A compound represented by the general formula (2) above, wherein R is ¹ ～R ⁹ Comprises the following steps:

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.

5. A coloring composition containing the above compound, wherein the solubility of the coloring composition in Propylene Glycol Monomethyl Ether Acetate (PGMEA) at 23 to 27 ℃ is 1 mass% or more.

6. A coloring composition containing the above compound, which uses a coating film containing the above compound to make the color difference (Delta E) between the color values before and after heating at 220-240 DEG C ^＊ _ab ) Is 3.5 or less.

7. A colorant for color filters, comprising the above compound or coloring composition.

8. A color filter uses the colorant for color filters.

(effect of the invention)

The compound according to the present invention is more excellent in solubility in an organic solvent such as PGMEA and heat resistance at the time of film formation than conventional yellow compounds, and therefore, a colored composition containing the compound according to the present invention is useful as a colorant for color filters.

Detailed Description

Hereinafter, embodiments of the present invention will be described in detail. The present invention is not limited to the following embodiments, and various modifications can be made within the scope of the present invention. First, the compound represented by the above general formula (1) will be described.

The compound of the present invention is represented by the following general formula (1). In the general formula (1), Q is a group represented by the following general formula (2), n represents an integer of 2 to 10, and L represents a group having a valence of 2 to 10. The plurality of Q's may be the same or different.

[ CHEM 3 ]

[ CHEM 4 ]

Therefore, the general formula (1) can be represented by the following general formula (1-2) using the general formula (2).

[ CHEM 5 ]

Wherein, in the general formula (1), when n is 2, a plurality of Q are represented as Q ¹ And Q ² In the case of (2), Q is represented by the following formula (1-3) ¹ And Q ² Via L as "Q ¹ ―L―Q ² And bonded as such.

[ CHEM 6 ]

Q ¹ -L-Q ² (1-3)

Further, in the general formula (1), when n is 3, a plurality of Q's are represented by Q ¹ 、Q ² And Q ³ In the case of (2), Q is represented by the following formula (1-4) ¹ ～Q ³ Can be bonded via L, Q ¹ ～Q ³ Each may be directly bonded to each other or may be exchanged with each other. When n is 4 or more, a plurality of Q may be bonded to each other via L as in the following formula (1-4).

[ CHEM 7 ]

Thus, in the general formula (1), even if n represents an integer of 2 to 10 and Q exists as a plurality of Q ¹ ～Q ¹⁰ In the case of (2), Q ¹ ～Q ¹⁰ Each may be bonded via L, Q ¹ ～Q ¹⁰ Each may be directly bonded to each other or may be exchanged with each other. Therefore, L represents a group having a valence of 2 to 10 corresponding to n. n is preferably 2 to 6, and more preferably 2 to 4.

As R in the general formula (2) ¹ ～R ⁹ The "halogen atom" may include: fluorine atom, chlorine atom, bromine atom, iodine atom, etc. The "halogen atom" is preferably a fluorine atom or a chlorine atom.

In the general formula (2), from R ¹ ～R ⁹ The "amino group having 0 to 25 carbon atoms which may have a substituent" may have a substituent or may not have a substituent, and when having a substituent, the group is represented by the formula "-NR ¹⁰ R ¹¹ "is represented by" has a substituent R ¹⁰ And R ¹¹ Examples of the "amino group" include: unsubstituted amino (-NH) ₂ ) Mono-substituted amino, di-substituted amino, and the like. The number of carbon atoms in the mono-or di-substituted amino group is, for example, 1 to 25, 1 to 20, or 2 to 10. The "amino group having 0 to 25 carbon atoms which may have a substituent" may be a group in which a "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms", "aromatic hydrocarbon group having 6 to 25 carbon atoms", "acyl group having 0 to 25 carbon atoms" or a "heterocyclic group having 5 to 25 ring atoms" described later is bonded via-NH-N < or-N-CH. Examples of the mono-substituted amino group include: ethylamino, butylamino, acetylamino, phenylamino and the like. Examples of the disubstituted amino group include: a dialkylamino group having 2 to 25 carbon atoms such as a dimethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group, or a dihexylamino group; a C4-25 dialkenylamino group such as a diallylamino group; diphenylamino, N-acetyl-N-phenylamino, (N-butyl) -N-phenylamino and the like.

In the general formula (2), from R ¹ ～R ⁹ The "C0-25 sulfonyl group which may have a substituent" means a sulfonyl group represented by "-SO ₂ ―R ¹⁰⁰ "(or" -) ₂ ―R ¹⁰⁰ ") represents a group having a substituent R ¹⁰⁰ A sulfonyl group of (a). "-" SO ₂ ―R ¹⁰⁰ "may also be a group containing no carbon atoms, and may be, for example," -SO ₃ H 'or SO containing an alkali metal atom "M' ₃ M' is adopted. Examples of the alkali metal atom "M" in the present invention include: lithium atom (Li), sodium atom (Na), potassium atom (K), cesium atom (Cs), or the like, preferably Li, Na, or K, more preferably Li or Na, and particularly preferably Na. R ¹⁰⁰ The number of carbon atoms of (A) is 0 to 25, may be 1 to 20, and may be 1 to 10. The C0-25 sulfonyl group which may have a substituent(s) is other than the above-mentioned-SO ₃ H、―SO ₃ In addition to M, there may be mentioned: sulfonamido (— S ═ O) ₂ ―NH ₂ ) Methanesulfonyl, toluenesulfonyl and the like.

In the general formula (2), as represented by R ¹ ～R ⁹ The "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms" in the "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent" includes, specifically: linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, isooctyl, and 2-ethylhexyl; cyclic alkyl groups (cycloalkyl groups) such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl; 1-adamantyl, 2-adamantyl; and so on.

In the general formula (2), as represented by R ¹ ～R ⁹ Among the "linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms" which may have a substituent(s) "represented by the above formula," a linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms ", specifically, there may be mentioned: vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 1-pentenyl, 1-hexenylStraight-chain or branched alkenyl groups such as isopropenyl and isobutenyl; cyclic alkenyl groups (cycloalkenyl groups) such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl; or a group in which a plurality of these linear, branched or cyclic alkenyl groups are bonded.

In the general formula (2), as represented by R ¹ ～R ⁹ Among the "linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms" represented by the "linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms which may have a substituent", specific examples thereof include: a straight chain alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a hexoxy group, a heptoxy group, an octoxy group, a nonoxy group, or a decyloxy group; branched alkoxy groups such as isopropoxy, isobutoxy, sec-butoxy, tert-butoxy and isooctyloxy; cyclic alkoxy groups (cycloalkoxy groups) such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, cyclononyloxy, and cyclodecyloxy; 1-adamantyloxy, 2-adamantyloxy; and so on.

In the general formula (2), from R ¹ ～R ⁹ The "acyl group having 1 to 25 carbon atoms which may have a substituent" is represented by "- (C ═ O) -R ¹⁰¹ "represents a group having a substituent R ¹⁰¹ A group of (1). Substituent R ¹⁰¹ May be a group containing a carbon atom, may be a group containing a nitrogen atom, or may be a group containing no carbon atom. At the substituent R ¹⁰¹ In the case of a group containing carbon atoms, the substituent R ¹⁰¹ The number of carbon atoms in (b) may be, for example, 1 to 25, or 1 to 20. At the substituent R ¹⁰¹ In the case of a group containing a nitrogen atom or a group containing no carbon atom, the substituent R ¹⁰¹ The number of carbon atoms in (b) may be, for example, 0 to 25, or 0 to 20. As substituents R ¹⁰¹ Examples thereof include: h, - (CH) ₃ 、―CH ₂ CH ₂ CH ₃ 、―CH＝CH ₂ 、―C ₆ H ₅ (phenyl) - (NH) ₂ 、―NHCH ₃ 、―NHCH ₂ CH ₃ Dimethylamino group, diethylamino groupA group such as a di (n-propyl) amino group, a di (n-butyl) amino group and the like, and may be a group represented by the formula R ¹ ～R ⁹ The same groups as the "amino group having 0 to 25 carbon atoms which may have a substituent" are described. The "acyl group having 1 to 25 carbon atoms" in the "acyl group having 1 to 25 carbon atoms which may have a substituent(s)" includes, specifically: formyl, acetyl, propionyl, acryloyl, benzoyl, and the like. "- (C ═ O) -R ¹⁰¹ "when containing a nitrogen atom, R may be an amide group, a primary amide group, a secondary amide group ¹⁰¹ May be represented by the formula R ¹ ～R ⁹ An exemplary group of the "amino group having 0 to 25 carbon atoms having a substituent" represented by the formula ¹⁰ R ¹¹ "represents a mono-substituted amino group or a di-substituted amino group.

In the general formula (2), from R ¹ ～R ⁹ The "ether group having 0 to 25 carbon atoms which may have a substituent" means a compound represented by the formula ¹⁰² "represents a group having a substituent R ¹⁰² An ether group of (a). Substituent R ¹⁰² Either a group containing carbon atoms or a group containing no carbon atoms. The "ether group having 0 to 25 carbon atoms" in the "ether group having 0 to 25 carbon atoms which may have a substituent" includes, specifically: an aminooxy group, an ester group represented by "- (C ═ O) - (R)" which is an arbitrary alkyl group, an aromatic hydrocarbon group or the like, a phosphoric acid group, a phosphoric acid ester group or the like.

In the general formula (2), as represented by R ¹ ～R ⁹ The "aromatic hydrocarbon group having 6 to 25 carbon atoms" in the "aromatic hydrocarbon group having 6 to 25 carbon atoms which may have a substituent" includes, specifically: aromatic hydrocarbon groups such as phenyl, biphenyl, terphenyl, naphthyl, anthryl (anthryl group ), phenanthryl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl and the like (the "aromatic hydrocarbon group" in the present invention also includes aryl groups or condensed polycyclic aromatic groups).

In the general formula (2), as represented by R ¹ ～R ⁹ In the "heterocyclic group having 5 to 25 ring-forming atoms which may have a substituent(s)", a hetero group having 5 to 25 ring-forming atomsCyclic group ", specifically, there are listed: a heterocyclic group (or a heterocyclic aromatic hydrocarbon group) such as a pyridyl group, a pyrimidyl group, a triazinyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a thienyl group, a furyl group, a pyrrolyl group, a quinolyl group, an isoquinolyl group, a naphthyridinyl group, an indolyl group, an acridinyl group, a phenanthrolinyl group, a benzofuranyl group, a benzothiophenyl group, an indolyl group, a carbazolyl group, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, a benzothiazolyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbolinyl group and the like.

In the general formula (2), as represented by R ¹ ～R ⁹ Of the representation

An amino group having 0 to 25 carbon atoms and having a substituent,

A "C0-25 sulfonyl group having a substituent group

"a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms and having a substituent group"),

"straight-chain, branched or cyclic alkenyl group having 2 to 25 carbon atoms and having a substituent group"),

"straight-chain, branched or cyclic alkoxy group having 1 to 25 carbon atoms and having a substituent group"),

"an acyl group having 1 to 25 carbon atoms and a substituent", "an ether group having 0 to 25 carbon atoms and a substituent

An "substituted aromatic hydrocarbon group having 6 to 25 carbon atoms", or

The "substituent" in the "heterocyclic group having 5 to 25 ring-forming atoms and having a substituent" includes, specifically:

deuterium atom, hydroxyl group, thiol group, cyano group, 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;

a 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;

an acyl group having 1 to 20 carbon atoms; an ether group having 1 to 20 carbon atoms;

an aromatic hydrocarbon group or a condensed polycyclic aromatic group having 6 to 20 carbon atoms;

a heterocyclic group having 5-20 ring atoms; and so on. When the "substituent" includes a carbon atom, the carbon atom is not included in the above "carbon number is 0 to 25", "carbon number is 1 to 25", and "carbon number is 6 to 25". These "substituents" may be contained in only 1 number, or may be contained in plural numbers, and in the case of containing plural numbers, they may be the same as each other, or may be different from each other. 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 above-mentioned compounds represented by R ¹ ～R ⁹ The number of "substituents" in each group shown is 10 at the maximum, and the maximum number of carbon atoms in each group is 100.

In the general formula (2), R represents ¹ ～R ⁹ The above-mentioned groups having "substituent" are exemplified by

A substituent group of an amino group having 0 to 20 carbon atoms,

A "C0-20 sulfonyl group

A linear, branched or cyclic alkyl group having 1 to 20 carbon atoms,

A straight-chain, branched or cyclic alkenyl group having 2 to 20 carbon atoms,

"straight-chain, 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", or

The "heterocyclic group having 5 to 20 ring-forming atoms" includes, specifically:

an amino group; a mono-or di-substituted amino group having a straight-chain or branched alkyl group having 3 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, such as a methylamino group, dimethylamino group, diethylamino group, ethylmethylamino group, dipropylamino group, di-tert-butylamino group, or diphenylamino group;

sulfonamido (— S ═ O) ₂ ―NH ₂ ) And a sulfonyl group having 0 to 20 carbon atoms (S ═ O) such as methanesulfonyl group and toluenesulfonyl group ₂ A group of (a); SO ₃ ^－、―SO ₃ H、―SO ₃ M (M is an alkali metal atom);

a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, a 2-ethylhexyl group, a heptyl group, an octyl group, an isooctyl group, a nonyl group, and a decyl group; a cyclic alkyl group (cycloalkyl group) having 3 to 20 carbon atoms such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclononyl group, or a cyclodecyl group; 1-adamantyl, 2-adamantyl;

a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 1-pentenyl group, a 1-hexenyl group, an isopropenyl group, an isobutenyl group, or a linear alkenyl group having 2 to 20 carbon atoms or a branched alkenyl group having 3 to 20 carbon atoms, wherein a plurality of these alkenyl groups are bonded; a cyclic alkenyl group (cycloalkenyl group) having 3 to 20 carbon atoms such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group;

a straight-chain alkoxy group having 1 to 20 carbon atoms or a branched-chain alkoxy group having 3 to 20 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an isopropoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, and an isooctyloxy group; a cyclic alkoxy group (cycloalkoxy group) having 3 to 20 carbon atoms such as a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cyclononyloxy group, or a cyclodecyloxy group; 1-adamantyloxy group, 2-adamantyloxy group;

acyl groups having 1 to 20 carbon atoms such as formyl group, acetyl group, propionyl group, acryloyl group, and benzoyl group; an ether group (-O-), an aminooxy group, an ester group (R is an arbitrary alkyl group, an aromatic hydrocarbon group or the like) represented by "-O- (C ═ O) -R" -), a phosphoric acid group, a phosphate group, or the like, and a group containing an ether group (-O-) having 0 to 20 carbon atoms;

an aromatic hydrocarbon group or a condensed polycyclic aromatic group having 6 to 20 carbon atoms such as a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, etc.;

a heterocyclic group having 5 to 20 ring atoms such as pyridyl, pyrimidyl, triazinyl, thienyl, furyl (furyl group ), pyrrolyl, imidazolyl, pyrazolyl, triazolyl, quinolyl, isoquinolyl, naphthyridinyl, acridinyl, phenanthrolinyl, benzofuranyl, benzothienyl, oxazolyl, indolyl, carbazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, quinoxalyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbolinyl and the like;

aryloxy groups having 6 to 19 carbon atoms such as phenoxy, tolyloxy, biphenyloxy, naphthyloxy, anthracenyloxy, phenanthrenyloxy, and the like; and so on.

In the general formula (2), R ¹ ～R ⁹ A ring may be formed by bonding adjacent groups to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom.

In the general formula (2), as R ¹ ～R ⁹ Preferably, the following components are used:

hydrogen atom, hydroxyl group, halogen atom, nitro group, cyano group,

An amino group having 1 to 20 carbon atoms which may have a substituent,

A linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent(s),

A linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent(s),

A linear or branched alkoxy group having 2 to 20 carbon atoms which may have a substituent(s),

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 optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,

more preferably:

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.

R ⁷ Or R ⁸ 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, R ⁶ Or R ⁹ Further preferably a hydrogen atom or a halogen atom.

In the general formula (1), n Q's represented by the general formula (2) are contained. In the general formula (2), a plurality of (n) Z's may be independently the same or different and are each a 2-valent group or a 3-valent group.

In the general formula (1), a plurality of Q are bonded to each other via L or Z. In the case where Z is a 2-valent group, for example, in the general formula (1), it is represented by "Q" as represented by the general formula (1-3) ¹ ―L―Q ² "can be expressed as the following formula (2-1). At this time, a plurality of R ¹ ～R ⁹ May be the same or different independently of each other. In the case of being represented by the following formula (2-1), any 1 or more of a plurality of Z may be a 3-valent group, and Z may be an appropriate group, for example, a group having R ¹⁰ 、R ¹¹ The 3-valent group of (1) may specifically be as followsThe following formula (2-2).

[ CHEM 8 ]

[ CHEM 9 ]

In the general formula (1), in the case where a plurality of Q are bonded via Z, for example, as in the following formula (2-3), each Q may be bonded to each other via a 2-valent group or a 3-valent group represented by Z.

[ CHEM 10 ]

In the general formula (1), the group represented by "L" represents a group having a valence of 2 to 10, and specific examples of L include groups having a valence of 2 to 10 using any of the following groups. In addition, L and Q may be bonded to each other at a site of an arbitrary substituent of the following groups.

As these groups, there can be mentioned:

"an amino group (or imino group) having 0 to 25 carbon atoms which may have a substituent(s)

A sulfonyl group having 0 to 25 carbon atoms which may have a substituent,

"optionally substituted linear, branched or cyclic alkyl group having 1 to 25 carbon atoms

"optionally substituted straight-chain, branched or cyclic alkenyl group having 2 to 25 carbon atoms

"optionally substituted linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms

An "acyl group having 1 to 25 carbon atoms which may have a substituent group"),

An "ether group having 0 to 25 carbon atoms which may have a substituent group"),

An "optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms", or

"heterocyclic group having 5 to 25 ring-forming atoms which may have a substituent".

Specifically, these groups are exemplified by R in the general formula (2) ¹ ～R ⁹ The groups listed are the same. As the "substituent" which these "groups" can have, R is also exemplified ¹ ～R ⁹ The groups represented can have the same "substituents".

L represented by these groups may form a group having any valence of 2 to 10 depending on the number (n) of Q or a bond with a plurality of Q at any position which may have a substituent. For example, the "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent" may be a "linear, 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 more. These "groups" or "substituents" may contain only 1 or a plurality thereof, and in the case of containing a plurality of groups, they may be the same as or different from each other. In addition, these "groups" or "substituents" may further have the groups or substituents exemplified above. Further, 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-mentioned "groups" or "substituents" contained in L is at most 10, and the maximum number of carbon atoms in each group is 100.

In the general formula (1), L represents a group having a valence of 2 to 10, and when L is a group which can be bonded to each other at a site of an arbitrary substituent of "a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which can have a substituent", L may be represented by "a linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which can have a substituent". Specifically, can listCarrying out: methylene, ethylene, -CHCH ₃ N-propylidene (propane-1, 3-diyl), isopropylidene, propane-1, 2-diyl, propane-2, 2-diyl, n-butylidene, isobutylidene, sec-butylidene, tert-butylidene, n-pentylidene, neopentylidene, n-hexylidene (hexane-1, 6-diyl, -) C ₆ H ₁₂ Examples of the "alkylene group" include, but are not limited to, groups in which 1 or more groups are bonded to a linear or branched alkylene group such as an n-heptyl group, an n-octyl group, an n-nonyl group, or an n-decyl group, or a cyclic alkylene group such as a cyclopropyl group, a cyclopentyl group, or a cyclohexyl group.

In the general formula (1), L is preferably:

a C0-25 amino group which may have a substituent,

An ether group having 0 to 25 carbon atoms which may have a substituent,

more preferably: a linear or branched alkylene group having 1 to 25 carbon atoms which may have a substituent.

In the general formula (2), the 2-valent group or the 3-valent group represented by Z represents:

an amino group having 0 to 25 carbon atoms which may have a substituent,

The group containing 1 or 2 or more of ether groups and single bonds includes groups obtained by substituting these groups with a 2-valent group or a 3-valent group at an appropriate position. These amino, alkylene or ether groups may comprise a plurality of identical radicals or a plurality of different radicals.

In Z of the general formula (2), examples of the "amino group having 0 to 25 carbon atoms" in the "amino group having 0 to 25 carbon atoms which may have a substituent" include: n <Or N-CH-or a compound of the general formula (2) wherein R is ¹ ～R ⁹ The same group as the "amino group having 0 to 25 carbon atoms which may have a substituent" is a group obtained by substituting a 2-valent group or a 3-valent group at an optional substituent position, wherein R is a substituent ¹² Can be expressed as-NR ¹² ―、＞N―R ¹² ―、―R ¹² ―NR ¹² ―R ¹² ―、―R ¹² ―NH―NR ¹² ―R ¹² Etc. As substituents R ¹² Examples thereof include compounds represented by the formula R ¹ ～R ⁹ The same groups as the "substituents" in the "amino group having 0 to 25 carbon atoms which may have a substituent" are mentioned. Plural R ¹² May be the same or different. In the general formula (2), when Z includes a plurality of "amino groups having 0 to 25 carbon atoms which may have a substituent", each Q may be bonded to a different Q via Z.

In the general formula (2), the "linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which may have a substituent" represented by Z may be exemplified by a group having a structure represented by R ¹ ～R ⁹ A group having a valence of 1 in which the substituent is a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent, and which has the same structure as the "1-valent group" is substituted with a 2-valent group at an arbitrary position. Specifically, the same groups as those listed as "linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which may have a substituent" represented by L may be used. The "substituent" in the "linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which may have a substituent" may be represented by R ¹ ～R ⁹ The same applies to the "substituent" of the "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent". These alkylene groups may also be branched to form a 3-valent group.

In the general formula (2), Z is a 2-valent group or a 3-valent group, preferably an amino group having 1 to 20 carbon atoms which may have a substituent, a linear, branched or cyclic alkylene group having 1 to 20 carbon atoms which may have a substituent, or a group containing an ether group, more preferably an amino group having 1 to 20 carbon atoms which may have a substituent.

It should be noted that, in the above description,

the "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 ".

The "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 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, branched or cyclic 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, branched or cyclic alkylene group having 1 to 25 carbon atoms, or a branched or cyclic alkylene group having 3 to 25 carbon atoms".

The compounds of the present invention are composed of the following groups:

1 group L having 2 to 10 valences (the same as L in the general formula (1)), (ii) a salt thereof,

n 1-valent groups R which are the same or different and represented by the following general formula (3) ⁰ 、

n identical or different 1-valent radicals R ¹² (synonymous with the substituent in the general formula (2) or a hydrogen atom), and

n identical or different 2-or 3-valent radicals Z (synonymous with Z in the general formula (2)),

n represents an integer of 2 to 10,

l is bonded to only Z and is,

R ⁰ is bonded only to the group Z and is,

R ¹² is bonded only to the group Z and is,

z and R ⁰ Bonded to and selected from L, R ¹² And one or both of the other Z groups are bonded.

[ CHEM 11 ]

(in the formula (3), R ¹ ～R ⁹ Synonymous with the above)

The compound represented by the general formula (1) (hereinafter, simply referred to as compound (1)) includes all stereoisomers and tautomers which can be produced. Specific examples of the compound (1) are shown below, but the present invention is not limited to these compounds. In the following structural formula, a part of hydrogen atoms is omitted.

[ CHEM 12 ]

[ CHEM 13 ]

[ CHEM 14 ]

[ CHEM 15 ]

[ CHEM 16 ]

[ CHEM 17 ]

[ CHEM 18 ]

[ CHEM 19 ]

[ CHEM 20 ]

[ CHEM 21 ]

[ CHEM 22 ]

[ CHEM 23 ]

[ CHEM 24 ]

[ CHEM 25 ]

[ CHEM 26 ]

[ CHEM 27 ]

[ CHEM 28 ]

[ CHEM 29 ]

[ CHEM 30 ]

[ CHEM 31 ]

The compound represented by the general formula (1) can be synthesized by the following method. In the general formula (1), n is 2, and Z is an optionally substituted group R ¹⁰ Amino group of (a), L is represented by-C ₆ H ₁₂ Example of synthesis of the case shown.

The 8-amino-2-methylquinoline derivative having a corresponding substituent is reacted with 1, 6-diiodohexane using a suitable solvent at a suitable temperature to obtain the following intermediate (X-1) having a corresponding substituent.

[ CHEM 32 ]

Further, the compound of the present invention represented by the general formula (1) can be obtained by subjecting the obtained intermediate (X-1) and trimellitic anhydride having a corresponding substituent to dehydration condensation reaction using an appropriate solvent at an appropriate temperature.

In the present invention, as a method for purifying the product, there can be mentioned: purifying by column chromatography; adsorbing and purifying by silica gel, active carbon, active clay and the like; known methods such as recrystallization from a solvent and crystallization are used. In the identification and analysis of these compounds, nuclear magnetic resonance analysis (NMR), absorbance measurement using a spectrophotometer, ultraviolet-visible absorption spectroscopy (UV-Vis) measurement, thermogravimetry-differential thermal analysis (TG-DTA), and the like can be performed. These analysis methods can also be used for the solubility, color evaluation, and heat resistance evaluation of the obtained compound.

The solubility of the compound of the present invention is expressed in terms of solubility, which represents the proportion of the maximum amount of a substance that can be dissolved in a specific solvent, and is expressed in units of "mass% (solvent name, temperature)" or the like, for example. The solubility is obtained, for example, by mixing a sample in a specific solvent, stirring the solvent at a certain temperature for a certain period of time, and measuring the concentration of the prepared saturated solution, and is also obtained by concentration measurement by Liquid Chromatography (LC), absorbance measurement, or the like in the dissolution section.

The thermal decomposition temperature can be analyzed by thermogravimetry-differential thermal analysis (TG-DTA) of the compound of the present invention, and can be used as an index of heat resistance. In the coloring composition, the thermal decomposition temperature of the compound of the pigment part is preferably 250 ℃ or higher. In the case of application to color filters, the higher the thermal decomposition temperature, the more preferable.

The compound of the present invention is mixed with various resin solutions used for colorants for color filters such as acrylic resins, and the mixture is applied onto a glass substrate by a method such as spin coating, and then heated and dried to form a coating film. The color of the obtained coating film was measured by a spectrophotometer to obtain a color value of the coating film, whereby the color characteristics were evaluated. Color values are typically measured using CIE L ^* a ^* b ^* Color system, etc. Specifically, measureColor value L of film sample ^* a ^* b ^* By the color difference (Δ E) of color values before and after heating at an appropriate temperature ^* _ab ) The heat resistance can be judged. In the case of application to a color filter, color difference at temperatures around 230 ℃ (for example, in the range of 220 ℃ to 240 ℃) can be used as an index of heat resistance. Is related to Delta E ^* _ab In addition, the smaller the value is, the more preferable the value is, the less discoloration of the color due to thermal decomposition is. Delta E ^* _ab Preferably 3.5 or less, more preferably 3 or less. The more the coloring compound is less discolored by thermal decomposition, the more excellent the coloring composition and the coloring agent for color filter are, the more excellent the coloring power, vividness and color quality.

The coloring composition contained in the coloring agent for color filters is preferably a composition having high solubility in an organic solvent because the coloring compound needs to be well dissolved or dispersed in the resin and the organic solvent. 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), etc.; aromatic hydrocarbons such as benzene, toluene, and xylene; amides such as N, N-Dimethylformamide (DMF) and N-methylpyrrolidone (NMP); dimethyl sulfoxide (DMSO), and the like. These solvents may be used alone, or 2 or more kinds thereof may be mixed and used. Among them, the compound according to the present invention is excellent in solubility in PGME and PGMEA, and for example, the solubility (% by mass) of PGMEA (solvent PGMEA, 25 ± 2 ℃) in a temperature range of 25 ± 2 ℃ (temperature in a range of 23 ℃ to 27 ℃) at room temperature is preferably 0.1% by mass or more, more preferably 1% by mass or more, and particularly preferably 2% by mass or more.

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

The coloring composition of the present invention contains the compound of the present invention represented by the general formula (1), and may contain 1 kind of structural compound or 2 or more kinds of structural compounds. In the present invention, the structure of the compound is preferably 1.

In order to improve the performance as a coloring agent for color filters, the coloring composition of the present invention may contain other components such as a surfactant, a dispersant, an antifoaming agent, a leveling agent, and an additive to be mixed in the production of other coloring agents for color filters. However, the content of these additives in the coloring composition is preferably an appropriate amount, and is preferably a content in a range in which the solubility of the coloring composition is not lowered, the solubility of the coloring composition is improved more than necessary, or the production of a color filter is not affected. These additives may be added at any timing for preparing the coloring composition.

The colorant for color filters of the present invention comprises: a coloring composition containing a compound represented by the general formula (1); and components generally used in the manufacture of color filters. A general color filter is obtained by: for example, in the case of a method using a photolithography step, a dye such as a dye or a pigment is mixed with a resin component (including a monomer, an oligomer, a binder component, and a resist component) and a solvent to prepare a liquid, the prepared liquid is applied onto a substrate such as glass or resin, and is photopolymerized using a photomask to prepare a colored pattern of a dye-resin composite film that is soluble/insoluble in the solvent, and the colored pattern is washed and then heated. The compound of the present invention has excellent solubility and excellent dispersibility with a material used for producing the color filter, and therefore can be mixed with another material as needed to form a film, and can be evaluated for heat resistance and light absorption characteristics. In the electrodeposition method and the printing method, a colored pattern may be formed using a mixture of a pigment, a resin, and other components. Therefore, specific components in the colorant for color filters of the present invention include compounds represented by the general formula (1), pigments such as other dyes and pigments, resin components, organic solvents, and other additives such as photopolymerization initiators. Further, these components may be selected alternatively or in addition to other components as necessary.

When the colored composition of the present invention is used as a colorant for color filters, it can be used as a yellow color filter, but it may be used in combination with a color filter for other colors such as red and green. The coloring composition of the present invention may be used alone, or other known coloring matters such as dyes and pigments may be mixed for hue adjustment. For example, there may be mentioned: a basic dye; an acid dye; disperse dyes; a Spilon dye; azo-based, bisazo-based, quinoline-based, stilbene-based, (poly) methine-based, cyanine-based, indigo-based, phthalocyanine-based, anthraquinone-based, acridine-based, triarylmethane-based, indanthrone-based, oxazine-based, dioxazine-based, naphthol AS-based, benzimidazolone-based, pyrazolone-based, perylene-based, perinone-based, quinacridone-based, isoindolinone-based, xanthene-based, diketopyrrolopyrrole-based dyes or pigments.

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

As the resin component in the coloring composition and the coloring agent for color filter of the present invention, a known resin component can be used as long as it has properties required in the production method and use of the color filter resin film formed by using them. For example, there may be mentioned: acrylic resin, olefin resin, styrene resin, polyimide resin, polyurethane resin, polyester resin, epoxy resin, vinyl ether resin, novolac resin, other transparent resins, photocurable resin, thermosetting resin, binder resin, and photoresist resin, and they may be used in appropriate combination. Further, copolymers of these resins may be used in combination. The content of the resin in the colorant for color filters is preferably 5 to 95% by mass, and more preferably 10 to 50% by mass in the case of a liquid colorant.

Other additives in the coloring composition and the color filter colorant of the present invention include: examples of the component necessary for polymerization and curing of the resin, such as a photopolymerization initiator and a crosslinking agent, include a surfactant and a dispersant necessary for stabilizing the properties of the components in a liquid colorant for color filters. Any known additive can be used for them, and is not particularly limited. The mixing ratio of the total amount of these additives in the solid content of the colorant for color filters is preferably 5 to 60 mass%, more preferably 10 to 40 mass%.

[ examples ] A method for producing a compound

Hereinafter, embodiments of the present invention will be specifically described with reference to examples, but the present invention is not limited to the following examples. It is noted that in the synthetic examples, the compounds were identified by ¹ H-NMR analysis (nuclear magnetic resonance device, Ascend, manufactured by Bruker Co., Ltd.) ^TM 400) To proceed with.

[ Synthesis example 1 ] Synthesis of Compound (A-5)

To the reaction vessel were added 48.0g of 8-amino-2-methylquinoline, 40.2g of triethylamine and 384mL of methylene chloride, and the mixture was cooled to 5 ℃ or lower in an ice bath. 82.8g of 2,4, 6-trimethylbenzoyl chloride was slowly added thereto, and the mixture was stirred at 25 ℃ for 7 hours. Water was added to the reaction solution, followed by extraction with methylene chloride. 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 mixture, followed by filtration to give N- (2,4, 6-trimethylbenzoyl) -8-aminoquinaldine (70.8g, yield 77%).

Subsequently, 17.5g of sodium hydride (60% dispersed in liquid paraffin) and 300mL of dehydrated DMF were added to the reaction vessel 1, and the mixture was cooled to 5 ℃ or lower in an ice bath. Using another reaction vessel 2, a solution was prepared by dissolving 60.6g of the above N- (2,4, 6-trimethylbenzoyl) -8-aminoquinaldine with dehydrated DMF300 mL. The solution in the reaction vessel 2 was slowly added dropwise to the reaction vessel 1, and stirred at 25 ℃ for 2 hours. 33.6g of 1, 6-diiodohexane was added thereto, and the mixture was stirred at 25 ℃ for 2 hours. 600mL of methylene chloride was added to the reaction mixture, and 600mL of water was gradually added dropwise and extracted with methylene chloride. The extract was concentrated under reduced pressure and purified by column chromatography (carrier: silica gel, solvent: dichloromethane/heptane 1/1 (vol.%)) to give the following intermediate (100) (68.8g, yield 100%).

[ CHEM 33 ]

Then, 68.8g of the intermediate (100) obtained above, 57.4g of trimellitic anhydride, 36.5g of benzoic acid, and 130mL of 1,2, 4-trichlorobenzene were added to the reaction vessel, and the mixture was stirred at 180 ℃ for 8 hours. After cooling to 25 ℃, 680mL of toluene was added to the reaction mixture, followed by filtration to obtain the following intermediate (101) (95.0g, yield 92%).

[ CHEM 34 ]

Then, 25.0g of the intermediate (101) obtained above, 8.1g of dibutylamine, 7.3g of triethylamine, 200mL of DMF, and 23.8g of 1- [ bis (dimethylamino) methylene ] -1H-1, 2, 3-triazolo [4, 5-b ] pyridinium 3-oxide Hexafluorophosphate (HATU) were added to the reaction vessel, and the mixture was stirred at 25 ℃ for 5 hours. To the reaction solution, water was added, and extraction was performed with dichloromethane. The extract was concentrated under reduced pressure and purified by column chromatography (carrier: silica gel, solvent: dichloromethane/acetone 10/1 (vol.%)) to give a yellow powder (15.0g, yield 49%).

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

¹ H－NMR(400MHz、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)

To reaction vessel 1, 8.6g of sodium hydride (60% dispersed in liquid paraffin) and 160mL of dehydrated DMF were added, and the mixture was cooled to 5 ℃ or lower in an ice bath. Using another reaction vessel 2, a solution was prepared by dissolving 32.7g of N- (2,4, 6-trimethylbenzoyl) -8-aminoquinaldine obtained in Synthesis example 1 in dehydrated DMF160 mL. The solution in the reaction vessel 2 was slowly added dropwise to the reaction vessel 1, and stirred at 25 ℃ for 2 hours. 21.2g of 1, 10-diiodododecane was added thereto, and the mixture was stirred at 25 ℃ for 2 hours. To the reaction mixture was added 320mL of methylene chloride, and 320mL of water was slowly added dropwise, followed by extraction with ethyl acetate. The extract was concentrated under reduced pressure and purified by column chromatography (carrier: silica gel, solvent: dichloromethane/heptane 1/1 (vol.%)) to give the following intermediate (102) (30.7g, yield 82%).

[ CHEM 35 ]

Then, 30.7g of the intermediate (102) obtained above, 24.4g of 2, 3-naphthalic anhydride, 15.0g of benzoic acid, and 80mL of 1,2, 4-trichlorobenzene were added to the reaction vessel, and the mixture was stirred at 180 ℃ for 8 hours. After cooling to 25 ℃, purification was performed by column chromatography (carrier: silica gel, solvent: dichloromethane/acetone-10/1 (vol.%)) to obtain a yellow powder (7.7g, yield 17%).

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

¹ H－NMR(400MHz、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)

30.7g of intermediate (102) obtained in Synthesis example 2, 24.0g of 3-chlorophthalic anhydride, 16.1g of benzoic acid, and 60mL of 1,2, 4-trichlorobenzene were charged into a reaction vessel, and the mixture was stirred at 180 ℃ for 8 hours. After cooling to 25 ℃, the product was purified by column chromatography (carrier: silica gel, solvent: 10/1 (vol.)) to obtain a yellow powder (20.7g, yield 51%).

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

¹ H－NMR(400MHz、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)

27.2g of the intermediate (100) obtained in Synthesis example 1, 20.4g of 4-methylphthalic anhydride, 15.4g of benzoic acid, and 50mL of 1,2, 4-trichlorobenzene were charged into a reaction vessel, and the mixture was stirred at 180 ℃ for 8 hours. After cooling to 25 ℃, purification was performed by column chromatography (carrier: silica gel, solvent: dichloromethane/acetone-10/1 (volume ratio)) to obtain a yellow powder (24.8g, yield 64%).

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

¹ H－NMR(400MHz、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 Compound (B-1)

To a reaction vessel were added 47.4g of N- (2,4, 6-trimethylbenzoyl) -N-propyl-8-aminoquinaldine, 17.8g of 4-methylphthalic anhydride, 13.4g of benzoic acid, and 80mL of 1,2, 4-trichlorobenzene obtained in the same manner as in Synthesis example 1, and the mixture was stirred at 180 ℃ for 8 hours. After cooling to 25 ℃, purification was performed by column chromatography (carrier: silica gel, solvent: heptane/dichloromethane/ethyl acetate 10/3/1 (volume ratio)) to obtain (B-1) as a yellow powder (24.0g, yield 36%).

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

¹ H－NMR(400MHz、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)。

[ CHEM 36 ]

[ example 1 ]

For the compound (A-5) obtained in Synthesis example 1, the solubility (% by mass) in a PGMEA solvent at room temperature (range from 23 ℃ to 27 ℃) was measured (solvent PGMEA, 25. + -. 2 ℃). The results are shown in table 1.

5.0g of a 25 mass% DMF-PGMEA mixed solution of a copolymer of methacrylic acid, acrylic ester and styrene and 20mg of the compound (A-5) obtained in Synthesis example 1 were put into a sample bottle and mixed with stirring for 30 minutes. The resulting colored resin solution (1 g) was applied (spin coating, 1000 rpm-6 seconds) to a glass substrate of 5cm × 5cm, and heated at 100 ℃ for 2 minutes to form a film. The color value of the obtained film was measured using a spectrophotometer (CM-5, manufactured by KONICA MINOLTA Co., Ltd.). Thereafter, the resultant was heated at 230 ℃ for 2 times for 20 minutes, and the color value was measured in the same manner. Color difference (Delta E) in color values before and after heating at 230 deg.C ^* _ab ) The results are shown in Table 1 as an index of heat resistance.

[ examples 2 to 4 ]

Synthesis examples 2E to 5 are used as the compounds in place of (A-5)4 (A-11), (A-19) and (A-20), the solubility (mass%) in a PGMEA solvent at room temperature was measured in the same manner as in example 1 (solvent PGMEA, 25. + -. 2 ℃ C.), and the color difference (. DELTA.E) between the color values before and after heating at 230 ℃ was measured for the resulting film (Δ E) ^* _ab ) And evaluated. The results are summarized in Table 1.

[ COMPARATIVE EXAMPLES 1 AND 2 ]

The solubility (% by mass) in a PGMEA solvent at room temperature (solvent PGMEA, 25 ± 2 ℃) was measured in the same manner as in example 1 except that the compound (B-1) obtained in synthesis example 5, which is a dye compound not belonging to the present invention, and c.i. solvent yellow 33 represented by the following formula (B-2), which is a conventional dye compound, were used instead of (a-5) as the compound. In addition, for the resulting film, the color difference (Δ E) of the color values before and after heating at 230 ℃ was measured ^* _ab ) And evaluated. The results are summarized in Table 1.

[ CHEM 37 ]

[ TABLE 1 ]

As shown in table 1, the compounds of the examples of the present invention exhibited high solubility in PGMEA and high heat resistance at the time of film formation, and the coloring compositions containing the compounds of the present invention had no problem in practical use as colorants for color filters. In addition, the film had higher heat resistance than comparative examples during film formation, and was excellent as a colorant for color filters.

(availability in industry)

The colored composition containing the compound (yellow compound) according to the present invention is excellent in solubility in an organic solvent (PGMEA or the like) and excellent in heat resistance at the time of film formation, and therefore is useful as a coloring material for various applications such as a coloring agent for a color filter.

Claims

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

in the formula (1), the reaction mixture is,

q is each independently a group represented by the following general formula (2),

n represents an integer of 2 to 10,

l represents a 2-10 valent group,

in the formula (2), the reaction mixture is,

R ¹ ～R ⁹ each independently represents:

hydrogen atom, hydroxyl group, halogen atom, cyano group, nitro group,

An amino group having 0 to 25 carbon atoms which may have a substituent,

A C0-25 sulfonyl group which may have a substituent,

A linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent,

A linear, branched or cyclic alkenyl group having 2 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,

R ¹ ～R ⁹ capable of bonding to each other between adjacent groups to form a ring,

z is each independently a 2-valent group or a 3-valent group, and represents:

an amino group having 0 to 25 carbon atoms which may have a substituent,

Containing 1 or 2 or more groups among ether groups or single bonds,

q's are bonded to each other via L or Z.

2. The compound of claim 1, wherein,

in the general formula (1), L is:

an amino group having 0 to 25 carbon atoms which may have a substituent,

An ether group having 0 to 25 carbon atoms which may have a substituent,

3. The compound according to claim 1 or 2, wherein,

in the general formula (2), Z is an amino group having 1 to 20 carbon atoms which may have a substituent.

4. The compound according to any one of claims 1 to 3, wherein,

in the general formula (2), R ¹ ～R ⁹ Comprises the following steps:

a hydrogen atom, a halogen atom,

An acyl group having 1 to 20 carbon atoms which may have a substituent.

5. A coloring composition comprising the compound according to any one of claims 1 to 4,

the solubility of the coloring composition in propylene glycol monomethyl ether acetate at 23-27 ℃ is 1 mass% or more.

6. A coloring composition comprising the compound according to any one of claims 1 to 4,

the color difference of the color value of the coloring composition before and after heating at 220-240 ℃ is less than 3.5 by using a coating film containing the compound.

7. A colorant for color filters comprising the compound according to any one of claims 1 to 4 or the coloring composition according to claim 5 or 6.

8. A color filter using the colorant for color filters according to claim 7.