TWI522425B - Compound - Google Patents

Description

Compound

The present invention relates to a compound useful as a dye.

The dye is used, for example, to display a color using reflected light or transmitted light in the fields of fiber materials, liquid crystal display devices, inkjet, and the like.

As such a dye, for example, a quinacridone dye C.I. Acid Yellow 3 represented by the following formula is widely known.

[Previous Technical Literature] [Non-patent literature]

Non-Patent Document 1: Yokote Masahiro, Shiba Miyazumi, "Synthetic Dyes", First Edition, Nikkan Kogyo Shimbun, April 1978, 128 pages

The above-mentioned compounds previously known cannot sufficiently satisfy the heat resistance.

The present invention provides the following [1] to [7].

[1] a compound represented by the formula (1), [In the formula (1), L ¹ represents a single bond, -SO ₂ - or -CO-, and A ¹ and A ² independently of each other represent a benzene ring which may have a substituent, a naphthalene ring which may have a substituent, or a quinoline ring having a substituent].

[2] The compound according to the above [1], wherein A ¹ is a benzene ring which may have a substituent.

[3] The compound according to [1] or [2] above, wherein the above substituent is a fluorinated alkyl group selected from the group consisting of -R ¹ , -OR ¹ , -COR ¹ , -O-COR ¹ , and carbon number 1-8. , halo, hydroxy, sulfanyl, sulfo, carboxy, nitro, decyl, -NHR ¹ and -NR ¹ R ² [wherein R ¹ and R ² represent an alkyl group having 1 to 8 carbon atoms] At least one of the group consisting of.

[4] The compound according to any one of the above [1] to [3] wherein A ¹ is an unsubstituted benzene ring or a benzene ring having a halogen group.

[5] The compound according to any one of the above [1] to [4] wherein A ¹ and A ² are the same.

[6] The compound according to any one of the above [1] to [5] wherein L ¹ is a single bond or -SO ₂ -.

[7] A coloring composition comprising the compound according to any one of [1] to [6] above.

The compound of the present invention is excellent in heat resistance.

The compound of the present invention is represented by the formula (1) (hereinafter, sometimes referred to as the compound (1)), [In the formula (1), L ¹ represents a single bond, -SO ₂ - or -CO-, and A ¹ and A ² independently of each other represent a benzene ring which may have a substituent, a naphthalene ring which may have a substituent, or a quinoline ring having a substituent].

L ¹ represents a single bond, -SO ₂ - or -CO-. In terms of heat resistance, L ^{1 is} preferably a single bond or -SO ₂ -.

A ¹ and A ² independently of each other represent a benzene ring which may have a substituent, a naphthalene ring which may have a substituent, or a quinoline ring which may have a substituent. Examples of the substituent include -R ¹ , -OR ¹ , -COR ¹ , -O-COR ¹ , a fluorinated alkyl group having 1 to 8 carbon atoms, a halogen group, a hydroxyl group, a sulfanyl group, a sulfo group, and the like. Carboxy, nitro, formamidine, -NHR ¹ and -NR ¹ R ² and the like. Here, R ¹ and R ² represent an alkyl group having 1 to 8 carbon atoms.

Examples of the alkyl group having 1 to 8 carbon atoms in R ¹ and R ² include a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, an n-octyl group, and the like. Linear alkyl; isopropyl, isobutyl, t-butyl, isopentyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl , 1-ethylbutyl, 2-ethylbutyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl Base, 2-ethylpentyl, 3-ethylpentyl, 1-propylbutyl, 1-(1-methylethyl)butyl, 1-(1-methylethyl)-2-methyl Propyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1-ethyl Hexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1-n-propylpentyl, 2-propylpentyl, 1-(1-methylethyl)pentyl, 1- Butylbutyl, 1-butyl-2-methylbutyl, 1-butyl-3-methylbutyl, 1-(1,1-dimethylethyl)butylbutyl, tert-butyl 1,1,1-dimethylpropyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl base , 1-ethyl-2-methylpropyl, 1,1-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 1,4-dimethyl Pentyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,3-dimethylpentyl, 3,4-dimethyl Pentyl, 1-ethyl-1-methylbutyl, 1-ethyl-2-methylbutyl, 1-ethyl-3-methylbutyl, 2-ethyl-1-methylbutyl , 2-ethyl-3-methylbutyl, 1,1-dimethylhexyl, 1,2-dimethylhexyl, 1,3-dimethylhexyl, 1,4-dimethylhexyl, 1 , 5-dimethylhexyl, 2,2-dimethylhexyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 3,3-dimethyl Hexyl, 3,4-dimethylhexyl, 3,5-dimethylhexyl, 4,4-dimethylhexyl, 4,5-dimethylhexyl, 1-ethyl-2-methylpentyl , 1-ethyl-3-methylpentyl, 1-ethyl-4-methylpentyl, 2-ethyl-1-methylpentyl, 2-ethyl-2-methylpentyl, 2 -ethyl-3-methylpentyl, 2-ethyl-4-methylpentyl, 3-ethyl-1-methylpentyl, 3-ethyl-2-methylpentyl, 3-B 3-methylpentyl, 3-ethyl-4-methylpentyl, 1-propyl-1-methylbutyl, 1-propyl-2-methylbutyl , 1-propyl-3-methylbutyl, 1-(1-methylethyl)-1-methylbutyl, 1-(1-methylethyl)-2-methylbutyl, 1 a branched alkyl group such as -(1-methylethyl)-3-methylbutyl, 1,1-diethylbutyl or 1,2-diethylbutyl.

Examples of the fluorinated alkyl group having 1 to 8 carbon atoms include a fluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a pentafluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, and a perfluoropentyl group. Base, perfluorohexyl, perfluoroheptyl and perfluorooctyl.

Examples of -OR ¹ include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, and a 2-ethylhexyloxy group.

Examples of -COR ¹ include an ethyl group, a propyl group, a butyl group, a pentamidine group, and a pentamidine group.

Examples of the -O-COR ¹ include an ethoxycarbonyl group, a propenyloxy group, a butoxy group, a pentyloxy group, and a p-pentyloxy group.

Examples of the -NHR ¹ include an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-butylamino group, an N-pentylamino group, and an N-octylamino group.

As -NR ¹ R ² , for example, N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-dibutylamino, N-butyl -N-methylamino group and N,N-dioctylamino group and the like.

Examples of the halogen group include a fluorine group, a chlorine group, a bromine group, and an iodine group, and a chlorine group is preferred.

In the above, A ¹ and A ^{2 are} preferably each independently a benzene ring which may have a substituent, and A ¹ and A ^{2 are more} preferably an unsubstituted benzene ring or a benzene ring having a halogen group. In this aspect, the halogen group is preferably a chlorine group.

Further, it is preferred that A ¹ and A ² are each independently an unsubstituted benzene ring or a benzene ring having a halogen group, and L ¹ is a single bond or -SO ₂ -. In this aspect, the halogen group is preferably a chlorine group.

Further, it is further preferred that A ¹ is the same as A ² and is an unsubstituted benzene ring or a benzene ring having a halogen group, and L ¹ is a single bond or -SO ₂ -. In this aspect, the halogen group is preferably a chlorine group.

As compound (1) Examples of the group represented by the following formula (q-1) to formula (q-46) include the following. Preferably, it is a formula (q-1), a formula (q-24), a formula (q-26), a formula (q-30), a formula (q-31), a formula (q-33), and a formula (( Q-35) and the base represented by formula (q-36).

Since the compound (1) is easier to manufacture, versus

It is preferably the same structure.

Examples of the compound (1) include the compound (1-1) to the compound (1-138). Furthermore, Q ¹ means Q ² means

In Table ^1, Q 1 and Q ² column column indicates the type of the above-exemplified group of numbers.

Compound (1) can be carried out by using a compound represented by formula (X), a compound represented by formula (Y1) and a compound represented by formula (Y2) in an organic solvent. Manufactured by reaction.

In the formula (X), the formula (Y1) and the formula (Y2), L ¹ , A ¹ and A ^{2 have} the same meanings as described above].

Examples of the organic solvent used in the reaction include N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, cyclobutyl hydrazine, N,N-dimethylformamide, and N,N. - dimethylacetamide and a mixed solvent of these. The amount of the organic solvent to be used varies depending on the type of the solvent, and is preferably from 3 to 50 parts by mass, more preferably from 5 to 20 parts by mass, per part by mass of the compound represented by the formula (X).

The total amount of the compound represented by the formula (Y1) and the compound represented by the formula (Y2) is 1 mol, preferably 2 to 8 mol, more preferably 2 to 8 mol, based on the compound represented by the formula (X). 3~5 moles.

The reaction temperature is preferably from 150 to 250 ° C, more preferably from 180 to 220 ° C. The reaction time is preferably from 5 to 72 hours, more preferably from 8 to 24 hours.

After completion of the reaction, the reaction liquid is mixed with the poor solvent of the compound (1), and the precipitate is collected by filtration, whereby the compound (1) can be obtained. Examples of the poor solvent include acetonitrile, ethyl acetate, tetrahydrofuran, and diethyl ether.

The amount of the poor solvent to be used is preferably 1 to 50 parts by mass, more preferably 5 to 20 parts by mass, per part by mass of the reaction liquid.

The precipitate obtained by filtration is preferably cleaned using an alcohol solvent or the like. Wash and then dry it. Further, it may be further purified by a known method such as recrystallization as needed. Examples of the alcohol solvent used for washing include methanol, ethanol, and isopropyl alcohol.

The compound of the present invention thus obtained is particularly useful as a coloring agent for a color filter of a display device such as a liquid crystal display device because of its high heat resistance.

The coloring composition of the present invention preferably contains the compound of the present invention as a coloring agent (hereinafter sometimes referred to as "coloring agent (A)"), and further contains a resin (B). More preferably, the colored composition of the present invention further comprises at least one selected from the group consisting of a polymerizable compound (C), a polymerization initiator (D), and a solvent (E).

The coloring agent (A) may further contain a pigment and/or a dye (although different from the compound of the present invention) in addition to the compound of the present invention.

As the dye, it can be exemplified as Solvent, Acid, and Basic in the Colour Index (published by The Society of Dyers and Colourists). , reactive, direct, disperse or reduced (Vat) dyes. More specifically, the dye of the following dye index (C.I.) number is mentioned, but it is not limited to this. Among them, an organic solvent-soluble dye is preferred.

CI Solvent Yellow 25, 79, 81, 82, 83, 89; CI Acid Yellow 7, 23, 25, 42, 65, 76; CI Reactive Yellow 2, 76, 116; CI Direct Yellow 4, 28, 44, 86 , 132; CI Disperse Yellow 54, 76; CI Solvent Orange 41, 54, 56, 99; CI Acid Orange 56, 74, 95, 108, 149, 162; CI Reactive Orange 16; CI Direct Orange 26; CI Solvent Red 24, 49 , 90, 91, 118, 119, 122, 124, 125, 127, 130, 132, 160, 218; CI acid red 73, 91, 92, 97, 138, 151, 211, 274, 289; CI acid purple 102 CI solvent green 1, 5; CI acid green 3, 5, 9, 25, 28; CI alkaline green 1; CI reduced green 1 and so on.

As the above pigment, an organic pigment or an inorganic pigment which is generally used for pigment dispersion resist can be mentioned. Examples of the inorganic pigment include a metal compound such as a metal oxide or a metal salt, and specific examples thereof include oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, and antimony. Or a composite metal oxide. Further, specific examples of the organic pigment and the inorganic pigment include a compound classified as a pigment in a Colour Index (published by The Society of Dyers and Colourists). More specifically, the following dye index (C.I.) number of pigments are mentioned, but it is not limited to these.

C.I. Pigment Yellow 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173 and 180; CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59 , 61, 64, 65 and 71; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 215, 216, 224, 242, 254, 255 and 264; CI Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38; CI Pigment Green 7, 10, 15, 25, 36, 47 and 58 and the like.

The content of the colorant (A) is preferably from 5 to 60% by mass based on the solid content of the coloring composition. Here, the solid content component means the total of the components which remove the solvent in the coloring composition.

The content of the compound of the present invention contained in the colorant (A) is preferably from 3 to 100% by mass.

These dyes and pigments may be used alone or in combination with the compound of the present invention, or may be used in combination with the compound of the present invention.

The resin (B) is not particularly limited, and any resin can be used. The resin (B) is preferably an alkali-soluble resin, more preferably a resin containing a structural unit derived from (meth)acrylic acid. Here, (meth)acrylic acid means acrylic acid and/or methacrylic acid.

Specific examples of the resin (B) include methacrylic acid/benzyl methacrylate copolymer, methacrylic acid/benzyl methacrylate/styrene copolymer, and methacrylic acid/benzyl methacrylate/ Methacrylic acid Ester copolymer, methacrylic acid/styrene/benzyl methacrylate/N-phenyl maleimide copolymer, methacrylic acid/styrene/glycidyl methacrylate copolymer, and the like.

The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably from 5,000 to 35,000, more preferably from 6,000 to 30,000.

The acid value of the resin (B) is preferably from 50 to 150, more preferably from 60 to 135.

The content of the resin (B) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, based on the solid content of the coloring composition.

The polymerizable compound (C) is not particularly limited as long as it is a compound which can be polymerized by an active radical generated from the polymerization initiator (D), an acid or the like. For example, a compound having a polymerizable ethylenically unsaturated bond or the like can be given.

The polymerizable compound (C) is preferably a polymerizable compound having three or more polymerizable groups. Examples of the polymerizable compound having three or more polymerizable groups include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethyl acrylate, dipentaerythritol hexaacrylate, and the like. Dipentaerythritol hexamethacrylate or the like. These polymerizable compounds may be used singly or in combination of two or more.

The content of the polymerizable compound (C) is preferably 5 to 65% by mass, and more preferably 10 to 60% by mass based on the solid content of the coloring composition.

Examples of the polymerization initiator (D) include a living radical generator, an acid generator, and the like. The living radical generator generates active radicals by the action of heat or light. Examples of the living radical generating agent include an alkylphenone compound, a thioxanthone compound, and three Compounds, hydrazine compounds, and the like.

As the above alkylphenone compound, for example, 2-methyl-2- Lolinyl-1-(4-methylsulfanylphenyl)propan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzoin dimethyl ketal, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, and the like.

Examples of the above thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthiaxanone, and 2,4-dichloro. Xanthone and 1-chloro-4-propoxythiaxanthone.

As the above three The compound may, for example, be 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-tri , 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-three , 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-three And 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-tri Wait.

Examples of the ruthenium compound include an O-acyloxime-based compound, and specific examples thereof include N-benzylideneoxy-1-(4-phenylsulfanylphenyl). Butan-1-one-2-imine, N-benzylideneoxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-acetoxy 1-[9-ethyl-6-(2-methylbenzylidenyl)-9H-indazol-3-yl]ethane-1-imine, N-ethyloxy-1- 9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxa Cyclopentylmethyloxy)benzhydryl}-9H-indazol-3-yl]ethane-1-imine and the like.

Further, as the living radical generating agent, for example, 2, 4, 6-three may also be used. Methyl benzhydryl diphenylphosphine oxide, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 10- Butyl-2-chloroacridone, 2-ethyl hydrazine, diphenylethylenedione, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, and titanocene compound.

Examples of the acid generator include 4-hydroxyphenyldimethylhydrazine p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, and 4-ethenyloxyphenyldimethylate. Base p-toluenesulfonate, 4-acetoxyphenyl-methyl-benzyl hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, An anthracene salt such as phenylhydrazine p-toluenesulfonate or diphenylphosphonium hexafluoroantimonate, or a nitrobenzyl tosylate or a benzoin tosylate.

These polymerization initiators may be used singly or in combination of two or more.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, per 100 parts by mass of the total of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator is in the above range, the sensitivity is high, the exposure time is shortened, and the productivity is improved, which is preferable.

The solvent (E) is not particularly limited as long as it can dissolve or disperse the compound of the present invention, and examples thereof include ethers, aromatic hydrocarbons, ketones, alcohols, esters, and amines.

Examples of the above ethers include tetrahydrofuran, tetrahydropyran, and 1,4-two. Alkane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl Ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether acetate , propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate and diethylene glycol single Butyl ether acetate and the like.

Examples of the aromatic hydrocarbons include benzene, toluene, xylene, and mesitylene.

Examples of the ketones include acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, and 4-hydroxy-4-methyl- 2-pentanone, cyclopentanone, cyclohexanone, and the like.

Examples of the alcohols include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin.

Examples of the esters include ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, and butyric acid. Ethyl ester, butyl butyrate, alkyl ester, methyl lactate, ethyl lactate, butyl lactate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, ethoxy acetic acid Methyl ester, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, Methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, Methyl 2-methoxy-2-methylpropanoate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate Ethyl acetate, ethyl 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, γ-butyrolactone, and the like.

Examples of the above guanamines include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

These solvents may be used singly or in combination of two or more.

The content of the solvent (E) in the coloring composition is preferably from 70 to 95% by mass, more preferably from 75 to 90% by mass, based on the coloring composition.

The colored composition of the present invention may optionally contain various additives such as a surfactant, a filler, other polymer compound, adhesion promoter, antioxidant, ultraviolet absorber, light stabilizer, chain transfer agent, and the like.

Since the compound of the present invention exhibits high heat resistance, it is particularly useful as a coloring agent for a color filter of a display device such as a liquid crystal display device.

Further, the coloring composition of the present invention can be used in a known display device including a color filter as a part of its constituent parts (for example, a known liquid crystal display device, an organic EL (Electro Luminescence) device, etc.) Various types of machines related to color images, such as solid-state imaging devices.

[Examples]

Next, the present invention will be more specifically described by way of examples. In the examples, unless otherwise stated, the % or the part of the content or the amount used is a quality standard.

In the following examples, the structure of the compound was confirmed by elemental analysis (VARIO-EL; (manufactured by Elementar Analytical Co., Ltd.)).

[Example 1]

After adding 5.26 parts of cyclopentanthene to 7.00 parts of the compound represented by the formula (X-1) (manufactured by Tokyo Chemical Industry Co., Ltd.), the mixture was heated to 180 ° C to be dissolved. After confirming the dissolution, 11.19 parts of quinaldine (Tokyo Chemical Industry Co., Ltd.) was added and refluxed at 200 ° C for 9 hours to carry out a reaction. Reaction junction After the bundle, the reaction solution was poured into 500 parts of acetonitrile and the precipitate was collected by filtration. The obtained precipitate was separately repulped by using 500 parts of ethanol and 500 parts of dimethyl hydrazine each to obtain a yellow solid. The yellow solid was dried at 60 ° C under reduced pressure to obtain 4.5 parts of a compound represented by formula (1-1) (hereinafter sometimes referred to as "compound (1-1)").

Identification of the compound represented by formula (1-1): (elemental analysis) C70.84 H3.28 N4.75 S5.09

[Embodiment 2]

After adding 5.26 parts of cyclobutyl hydrazine to 7.00 parts of the compound represented by the formula (X-1), the mixture was heated to 180 ° C to be dissolved. After confirming dissolution, 13.88 parts of 8-chloroquinaldine was added and refluxed at 200 ° C for 9 hours. After completion of the reaction, the reaction solution was poured into 500 parts of acetonitrile and the precipitate was collected by filtration. The obtained precipitate was separately repulped by using 500 parts of ethanol and 500 parts of dimethyl hydrazine each to obtain a yellow solid. The yellow solid was dried at 60 ° C under reduced pressure to obtain 8.15 parts of a compound represented by formula (1-26) (hereinafter sometimes referred to as "compound (1-26)").

Identification of the compound represented by formula (1-26): (elemental analysis) C63.3 H2.8 N3.8 C110.2 S5.0

[Example 3]

After adding 92.65 parts of cyclobutyl hydrazine to 10.0 parts of the compound represented by the formula (X-2) (manufactured by Tokyo Chemical Industry Co., Ltd.), the mixture was heated to 180 ° C to be dissolved. After confirming dissolution, 24.15 parts of quinaldine was added and refluxed at 200 ° C for 9 hours. After completion of the reaction, the reaction solution was poured into 500 parts of acetonitrile and the precipitate was collected by filtration. The obtained precipitate was separately repulped by using 500 parts of ethanol and 500 parts of dimethyl hydrazine each to obtain a yellow solid. The yellow solid was dried at 60 ° C under reduced pressure to obtain 13.5 parts of a compound represented by formula (1-47) (hereinafter sometimes referred to as "compound (1-47)").

Identification of the compound represented by formula (1-47): (elemental analysis) C79.97 H3.68 N5.31

[Example 4]

After adding 64.86 parts of cyclobutyl hydrazine to 7.0 parts of the compound represented by the formula (X-2), the mixture was heated to 180 ° C to be dissolved. After confirming dissolution, add 8-chloroquine Which pyridine was 16.90 parts and refluxed at 200 ° C for 9 hours. After completion of the reaction, the reaction solution was poured into 500 parts of acetonitrile and the precipitate was collected by filtration. The obtained precipitate was separately repulped by using 500 parts of ethanol and 500 parts of dimethyl hydrazine each to obtain a yellow solid. The yellow solid was dried at 60 ° C under reduced pressure to obtain 9.0 parts of a compound represented by formula (1-72) (hereinafter sometimes referred to as "compound (1-72)").

Identification of the compound represented by formula (1-72): (elemental analysis) C68.5 H3.0 N3.6 C110.4

[Heat resistance evaluation]

For the compound obtained in the examples, a differential scanning calorimetry was performed using a thermogravimetric differential thermal measurement apparatus (EXSTAR TG/DTA6200R; manufactured by SII NanoTechnology Co., Ltd.) to determine a weight reduction rate of 10%. The temperature is T ₁₀ . The results are shown in Table 2.

In Table 2, the compound (R-1) was C.I. Acid Yellow 3 (manufactured by Tokyo Chemical Industry Co., Ltd.).

[Example 5] [Preparation of coloring composition]

The following ingredients were mixed to obtain a coloring composition:

[Production of color filter]

The coloring composition obtained above was applied to the glass by spin coating to volatilize the volatile component. After cooling, light irradiation was performed using a patterned quartz glass mask and an exposure machine. After light irradiation, development was carried out using an aqueous potassium hydroxide solution, and the mixture was heated to 200 ° C in an oven to obtain a color filter.

[Embodiment 6]

A coloring composition and a color filter were obtained in the same manner as in Example 5 except that the compound (I-1) synthesized in Example 1 was replaced with the compound (I-26) synthesized in Example 2.

[Embodiment 7]

A coloring composition and a color filter were obtained in the same manner as in Example 5 except that the compound (I-1) synthesized in Example 1 was replaced with the compound (I-47) synthesized in Example 3.

[Embodiment 8]

A coloring composition and a color filter were obtained in the same manner as in Example 5 except that the compound (I-1) synthesized in Example 1 was replaced with the compound (I-72) synthesized in Example 4.

From the results of Table 2, it is understood that the compound of the present invention exhibits high heat resistance. The coloring composition containing the compound can produce a color filter which is less deteriorated by heat and has higher durability.

[Industrial availability]

The compound of the present invention is excellent in heat resistance.

Claims (5)

a compound represented by the formula (1), [In the formula (1), L ¹ represents a single bond, -SO ₂ - or -CO-, and A ¹ and A ² independently of each other represent a benzene ring which may have a substituent selected from -R ¹ , - OR ¹ , -COR ¹ , -O-COR ¹ , fluorinated alkyl group having a carbon number of 1 to 8, halogen group, hydroxyl group, sulfanyl group, sulfo group, nitro group, methyl group, -NHR ¹ and -NR ¹ R ² [wherein, R ¹ and R ² represent at least one of the group consisting of an alkyl group having 1 to 8 carbon atoms]. The compound of claim 1, wherein A ¹ and A ² are each independently an unsubstituted benzene ring or a benzene ring having a halogen group. The compound of claim 1, wherein A ¹ and A ² are the same. The compound of claim 1, wherein L ¹ is a single bond or -SO ₂ -. A coloring composition comprising the compound of claim 1.