KR20120116340A - Compound - Google Patents

Abstract

PURPOSE: A compound for dye is provided to enhance heat resistance. CONSTITUTION: A compound for dye is represented by chemical formula(1). In the chemical formula(1), L1 indicates a short-chain, -SO2- or -CO-. A1 and A2 indicate benzene rings which independently have with substituent, naphthalene rings with substituent or quinoline rings with substituent. The compound(1) is manufactured by reacting a compound indicated by a formula (X), a compound indicated by a formula (Y1) and a compound indicated by a formula (Y2) in an organic solvent. The organic solvent used in the reaction is N-methylpyrolidone, 1,3- dimethyl -2- imidazolidinone, sulfolane, N,N- dimethylformamide, N,N- dimethylacetamide or a mixed solvent thereof. The used amount of the organic solvent is 30-50 parts by weight based on 1 part by weight of the compound. The coloring composite includes the compound of the chemical formula(1).

Description

Compound {COMPOUND}

The present invention relates to compounds useful as dyes.

Dye is used for color display using reflected light or transmitted light, for example in the field of a fiber material, a liquid crystal display device, an inkjet, etc.

As such a dye, for example, Quinophthalone dye C.I. Acid Yellow 3 is widely known.

[Non-Patent Document 1] Masao Yokote, Fukumatsu Shibamiya, Synthetic Dye, First Edition, Nikkan Kogyo Shimbun, April 1978, 128 pages

The compound known in the art has not been sufficiently satisfactory for heat resistance.

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

[1] Formula (１)

In the formula ^(1), L 1 represents a single bond, -SO ₂ - or denotes a -CO-. A ¹ and A ² each independently 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.

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

[3] The substituent is -R ¹ , -OR ¹ , -COR ¹ , -O-COR ¹ , a C1-8 fluorinated alkyl group, halogeno group, hydroxy group, sulfanyl group, sulfo group, carboxyl group, nitro group , A formyl group, -NHR ¹ and -NR ¹ R ² wherein R ¹ and R ² represent an alkyl group having 1 to 8 carbon atoms, and the compound according to [1] or [2]. .

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

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

[6] The compound according to any one of [1] to [5], wherein L ¹ is a single bond or -SO _2- .

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

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

The compound of the present invention is a compound represented by the formula (1) hereinafter referred to as compound (1).

In the formula ^(1), L 1 represents a single bond, -SO ₂ - or denotes a -CO-. A ¹ and A ² each independently 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;

L ¹ represents a single bond, -SO _2- , or -CO-. L ¹ is preferably a single bond or -SO ₂ -from the viewpoint of heat resistance.

A ¹ and A ² each independently 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 such substituents ^{-R 1, -OR 1, -COR 1} , -O-COR 1, C 1? 8 fluorinated alkyl group, a halogeno, a hydroxyl group, a sulfanyl group, sulfo group, carboxyl group, a nitro group, a formyl group , -NHR ¹ , -NR ¹ R ² , and the like. Here, R <^1> and R <^2> represent a C1-C8 alkyl group.

As a C1-C8 alkyl group in R <^1> and R <^2> , a methyl group, an ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-jade Straight chain alkyl groups such as a methyl group;

Isopropyl group, isobutyl group, sec-butyl group, isopentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylbutyl group, 2-ethyl Butyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl , 1-propylbutyl group, 1- (1-methylethyl) butyl group, 1- (1-methylethyl) -2-methylpropyl group, 1-methylheptyl group, 2-methylheptyl group, 3-methylheptyl group , 4-methylheptyl group, 5-methylheptyl group, 6-methylheptyl group, 1-ethylhexyl group, 2-ethylhexyl group, 3-ethylhexyl group, 4-ethylhexyl group, 1-n-propylpentyl group , 2-propylpentyl group, 1- (1-methylethyl) pentyl group, 1-butylbutyl group, 1-butyl-2-methylbutyl group, 1-butyl-3-methylbutyl group, 1- (1,1 -Dimethylethyl) butylbutyl group, tert-butyl group, 1,1-dimethylpropyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethyl Butyl group, 1-ethyl-2-methylpropyl group, 1,1-dimethylpentyl group, 1,2-dimethylpentyl group, 1,3-dimethylpentyl group, 1,4-dimethylpentyl group, 2,2-dimethylpentyl group, 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 3, 3-dimethylpentyl group, 3,4-dimethylpentyl group, 1-ethyl-1-methylbutyl group, 1-ethyl-2-methylbutyl group, 1-ethyl-3-methylbutyl group, 2-ethyl-1- Methylbutyl group, 2-ethyl-3-methylbutyl group, 1,1-dimethylhexyl group, 1,2-dimethylhexyl group, 1,3-dimethylhexyl group, 1,4-dimethylhexyl group, 1,5- Dimethylhexyl group, 2,2-dimethylhexyl group, 2,3-dimethylhexyl group, 2,4-dimethylhexyl group, 2,5-dimethylhexyl group, 3,3-dimethylhexyl group, 3,4-dimethylhexyl Real group, 3, 5- dimethylhexyl group, 4, 4- dimethylhexyl group, 4, 5- dimethylhexyl group, 1-ethyl-2-methylpentyl group, 1-ethyl-3- methylpentyl group, 1-ethyl- 4-methylpentyl group, 2-ethyl-1-methylpentyl group, 2-ethyl-2-methylpentyl group, 2-ethyl-3-methylpentyl group, 2-ethyl-4-methylpentyl group, 3-ethyl- 1-methylpentyl group, 3-ethyl-2-methylpentyl group, 3-ethyl-3-methylpentyl group, 3-ethyl-4-methylpentyl group, 1-propyl-1-methyl moiety Methyl group, 1-propyl-2-methylbutyl group, 1-propyl-3-methylbutyl group, 1- (1-methylethyl) -1-methylbutyl group, 1- (1-methylethyl) -2-methylbutyl And branched alkyl groups such as groups, 1- (1-methylethyl) -3-methylbutyl group, 1,1-diethylbutyl group and 1,2-diethylbutyl group.

As a C1-C8 fluorinated alkyl group, a fluoromethyl group, a trifluoromethyl group, a fluoroethyl group, pentafluoroethyl group, a perfluoro propyl group, a perfluoro butyl group, a perfluoro pentyl group, perfluoro, for example A rohexyl group, a perfluoroheptyl group, a perfluorooctyl group, etc. are mentioned.

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

Examples of -COR ¹ include an acetyl group, propionyl group, butyryl group, valeryl group, pivaloyl group and the like.

Examples of -O-COR ¹ include an acetyloxy group, propionyloxy group, butyryloxy group, valeryloxy group, pivaloyloxy group and the like.

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

As -NR ¹ R ² , for example, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N-dibutylamino group, N-butyl-N-methylamino group, N, N-dioctylamino group etc. are mentioned.

As a halogeno group, a fluoro group, a chloro group, a bromo group, an iodine group, etc. are mentioned, Preferably it is a chloro group.

A ¹ and A ² in the above is preferably a benzene ring which may independently have a substituent one another, A ¹ and A ² is more preferably a benzene ring independently having the shop unsubstituted benzene ring or a halo group to each other . In this form, it is preferable that the halogeno group is a chloro group.

In addition, A ¹ and A ² is independently a non-substituted benzene ring or to a benzene ring having a haloalkyl group to each other, L ¹ is only a bond or -SO ₂ - is preferably a. In this form, it is preferable that the halogeno group is a chloro group.

Furthermore, A ¹ and A ² are the same, and also to a non-substituted benzene ring or a benzene ring having a haloalkyl group, L ¹ is only a bond or -SO ₂ - is still more preferably a. In this form, it is preferable that the halogeno group is a chloro group.

In compound (1)

또는

or

As group represented by these, the group etc. which are represented by following formula (VII-1) -formula (VII-46) are mentioned. Preferably, Formula (VIII), Formula (V24), Formula (V23), Formula (V3), Formula (V3), Formula (V3), Formula (V2) 35) and the group represented by a formula (VII-36) are mentioned.

Since the preparation of compound (1) is easy,

와

는 동일한 구조인 것이 바람직하다.

Wow

Is preferably the same structure.

As compound (1), a compound (1-1)-a compound (1.13 kPa) etc. are mentioned, for example. Moreover, Q ¹

And Q ² is

Indicates. In Table 1, the Q ¹ column and the Q ² column describe the numbers of the formulas of the groups exemplified above.

Compound (1) can be manufactured by making the compound represented by Formula (VIII), the compound represented by Formula (X1), and the compound represented by Formula (X2) react in an organic solvent.

[L <^1> , A <^1> and A <^2> show the same meaning as the above in Formula (VII), Formula (XI1), and Formula (VII2).

Organic solvents used for the reaction include N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, sulfolane, N, N-dimethylformamide, N, N-dimethylacetamide and mixed solvents thereof Can be mentioned. Although the usage-amount of an organic solvent changes with kinds of solvent, 3-50 mass parts is preferable with respect to 1 mass part of compounds represented by Formula (i), and 5-20 mass parts is more preferable.

2-8 mol is preferable with respect to 1 mol of usage-amount of the compound represented by Formula (Xi), and, as for the total usage-amount of the compound represented by Formula (X1) and Formula (X2), 3-5 mol is more preferable.

150-250 degreeC is preferable and 180-220 degreeC of reaction temperature is more preferable. 5-72 hours are preferable and, as for reaction time, 8-24 hours are more preferable.

After completion | finish of reaction, the reaction liquid is mixed with the poor solvent of compound (1), and a precipitate is filtered and compound (1) can be obtained. As a poor solvent, acetonitrile, ethyl acetate, tetrahydrofuran, diethyl ether is mentioned, for example.

The use amount of the poor solvent is preferably 1 to 50 parts by mass, and more preferably 5 to 20 parts by mass with respect to 1 part by mass of the reaction liquid.

The precipitate obtained by filtration is preferably washed with an alcohol solvent or the like and then dried. Moreover, you may refine | purify further by well-known methods, such as recrystallization as needed. Methanol, ethanol, isopropyl alcohol, etc. are mentioned as an alcohol solvent used for washing | cleaning.

Since the compound of this invention obtained in this way has high heat resistance, it is especially useful as a coloring agent used for color filters of display apparatuses, such as a liquid crystal display device.

It is preferable that the coloring composition of this invention contains the compound of this invention as a coloring agent (henceforth "coloring agent (A)"), and contains resin further. It is further more preferable that the coloring composition of this invention contains 1 or more types chosen from the group which consists of a polymeric compound (C), a polymerization initiator (D), and a solvent (E).

In addition to the compound of this invention, a coloring agent (A) may contain the pigment and / or dye (however different from the compound of this invention).

Examples of the dye include Solvent, Acid, Basic, Reactive, Direct, and Disperse in the Color Index (Published by The Society of Dyers and Colourists). Or dyes classified as bats. More specifically, dyes having the following color index (C.I.) numbers may be mentioned, but are not limited thereto. Among these, organic solvent soluble dye is preferable.

C.I. Solvent yellow 25, 79, 81, 82, 83, 89;

C.I. Acid yellow 7, 23, 25, 42, 65, 76;

C.I. Reactive yellow 2, 76, 116;

C.I. Direct yellow 4, 28, 44, 86, 132;

C.I. Dispulse yellow 54, 76;

C.I. Solvent orange 41, 54, 56, 99;

C.I. Acid orange 56, 74, 95, 108, 149, 162;

C.I. Reactive orange 16;

C.I. Direct orange 26;

C.I. Solvent red 24, 49, 90, 91, 118, 119, 122, 124, 125, 127, 130, 132, 160, 218;

C.I. Acid red 73, 91, 92, 97, 138, 151, 211, 274, 289;

C.I. Acid violet 102;

C.I. Solvent green 1, 5;

C.I. Acid green 3, 5, 9, 25, 28;

C.I. Basic Green 1;

C.I. Bat Green 1 etc.

As said pigment, the organic pigment or inorganic pigment normally used for a pigment dispersion registry is mentioned. Examples of the inorganic pigments include metal compounds such as metal oxides and metal complex salts. Specifically, oxides or complex metal oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc and antimony Can be mentioned. Moreover, as an organic pigment and an inorganic pigment, the compound specifically classified by Pigment in the Color Index (The Society of Dyers and Colourists) is mentioned. More specifically, the pigment of the following color index (C.I.) number is mentioned, 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;

C.I. Pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65 and 71;

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 215, 216, 224, 242, 254, 255 and 264;

C.I. Pigment violet 14, 19, 23, 29, 32, 33, 36, 37 and 38;

C.I. Pigment green 7, 10, 15, 25, 36, 47 and 58;

Content of a coloring agent (A) becomes like this. Preferably it is 5-60 mass% with respect to solid content in a coloring composition. Here, solid content means the sum total of the component except the solvent in a coloring composition.

Content of the compound of this invention contained in a coloring agent (A) becomes like this. Preferably it is 3-100 mass%.

You may use these dyes and pigments individually or in combination of 2 or more types like the compound of this invention.

It does not specifically limit as resin, You may use any resin. It is preferable that resin (i) is alkali-soluble resin, and it is still more preferable that it is resin containing the structural unit guide | induced from (meth) acrylic acid. Here, (meth) acrylic acid represents acrylic acid and / or methacrylic acid.

Specific examples of the resin include methacrylic acid / benzyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene copolymer, methacrylic acid / benzyl methacrylate / isobornyl methacrylate copolymer, Methacrylic acid / styrene / benzyl methacrylate / N-phenylmaleimide copolymer, methacrylic acid / styrene / glycidyl methacrylate copolymer, etc. are mentioned.

As for the polystyrene conversion weight average molecular weight of resin, 5,000-35,000 are preferable, More preferably, it is 6,000-30,000.

As for the acid value of resin, 50-150 are preferable, More preferably, it is 60-135. Content of resin is preferably 7-65 mass% with respect to solid content of a coloring composition, More preferably, it is 13-60 mass%.

A polymerizable compound (C) will not be specifically limited if it is a compound which can superpose | polymerize with the active radical, the acid, etc. which generate | occur | produced in the polymerization initiator (D). For example, the compound etc. which have a polymerizable ethylenically unsaturated bond are mentioned.

As said polymeric compound (C), it is preferable that it is a polymeric compound which has 3 or more of polymeric groups. As a polymeric compound which has three or more polymerizable groups, for example, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerytate Lithol hexaacrylate, dipentaerythritol hexamethacrylate, etc. are mentioned. You may use these polymeric compounds individually or in combination of 2 or more types.

It is preferable that content of a polymeric compound (C) is 5-65 mass% with respect to solid content of a coloring composition, More preferably, it is 10-60 mass%.

As said polymerization initiator (D), an active radical generator, an acid generator, etc. are mentioned. Active radical generators generate active radicals by the action of heat or light. Examples of the active radical generator include alkylphenone compounds, thioxanthone compounds, triazine compounds, oxime compounds, and the like.

As said alkylphenone compound, 2-methyl-2- morpholino-1- (4-methylsulfanylphenyl) propane-1-one, 2-hydroxy-2-methyl-1-phenyl propane-, for example 1-one, benzyl dimethyl ketal, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexylphenyl ketone, etc. are mentioned. have.

As said thioxanthone compound, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, 1-chloro-, for example 4-propoxy city oxanthone etc. are mentioned.

As said triazine compound, it is 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1, 3, 5- triazine, 2, 4-bis (trichloromethyl), for example. -6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5-tri Azine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl ) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino- 2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3, 5-triazine etc. are mentioned.

Examples of the oxime compound include O-acyl oxime compounds, and specific examples thereof include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine and N- Benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3 -Yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethane-1-imine, etc. are mentioned.

As the active radical generator, for example, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, 2,2'-bis (o-chlorophenyl) -4,4 ', 5,5'-tetraphenyl -1,2'-biimidazole, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, benzyl, 9,10-phenanthrenequinone, camphorquinone, phenylglyoxylate, titanocene compounds You may use it.

As said acid generator, 4-hydroxyphenyl dimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyl dimethylsulfonium hexafluoro antimonate, 4-acetoxyphenyl dimethylsulfonium p-toluene, for example Sulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfo Onium salts such as nate and diphenyl iodonium hexafluoroantimonate, nitrobenzyl tosylates, benzointosylates and the like.

You may use these polymerization initiators individually or in combination of 2 or more types.

Content of a polymerization initiator (D) becomes like this. Preferably it is 0.1-30 mass parts with respect to 100 mass parts of total amounts of resin (K) and a polymeric compound (C), More preferably, it is 1-20 mass parts. When content of a polymerization initiator exists in the said range, since it becomes high sensitivity and shortens an exposure time and improves productivity, it is preferable.

The solvent (E) is not particularly limited as long as the compound of the present invention can be dissolved or dispersed, and examples thereof include ethers, aromatic hydrocarbons, ketones, alcohols, esters, amides, and the like.

Examples of the ethers include tetrahydrofuran, tetrahydropyran, 1,4-dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether and 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, diethylene glycol And the like can be furnace-butyl ether acetate.

As said aromatic hydrocarbons, benzene, toluene, xylene, mesitylene, etc. are mentioned, for example.

As said ketones, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-heptanone, 4-hydroxy-4-methyl-2-, for example Pentanone, cyclopentanone, cyclohexanone, etc. are mentioned.

As said alcohol, methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerin, etc. are mentioned, for example.

As said ester, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, lactic acid, for example Methyl, ethyl lactate, butyl lactate, methoxyacetic acid methyl, methoxyacetic acid ethyl, methoxyacetic acid butyl, ethoxyacetic acid methyl, ethoxyacetic acid ethyl, 3-methoxypropionate methyl, 3-methoxypropionate ethyl 3- Methyl oxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionic acid, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-methoxy Methyl 2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, acetoacetic acid Methyl, ethyl acetoacetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, (gamma) -butyrolactone, etc. are mentioned.

As said amides, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, etc. are mentioned, for example.

You may use these solvents individually or in combination of 2 or more types.

Content of a solvent (E) in a coloring composition becomes like this. Preferably it is 70-95 mass% with respect to a coloring composition, More preferably, it is 75-90 mass%.

The coloring composition of this invention may contain various additives, such as surfactant, a filler, other polymeric compounds, adhesion promoter, antioxidant, an ultraviolet absorber, a light stabilizer, a chain transfer agent, as needed.

Since the compound of this invention shows high heat resistance, it is especially useful as a coloring agent used for color filters of display apparatuses, such as a liquid crystal display device.

Moreover, the coloring composition of this invention relates to various colored images, such as a display apparatus (for example, a well-known liquid crystal display device, an organic electroluminescent apparatus, etc.), a solid-state image sensor, etc. which comprise a color filter as a part of its component parts. It can be used in a form known in the device.

[Example]

Next, an Example is given and this invention is demonstrated further more concretely. In the examples,% and parts indicating content to amount of use are based on mass unless otherwise specified.

In the following examples, the structure of the compound is elemental analysis [VARIO-EL; (Identified by Elemental Co., Ltd.).

Example 1

53.26 parts of sulfolane was added to 7.00 parts of the compound (manufactured by Tokyo Kasei Co., Ltd.) represented by the formula (VII-1), and then heated to dissolve at 180 ° C. After confirming the dissolution, 11.19 parts of quinaldine (manufactured by Tokyo Kasei Co., Ltd.) was added, and the mixture was refluxed at 200 ° C. for 9 hours to react. After the reaction was completed, the reaction solution was poured into 500 parts of acetonitrile and the precipitate was filtered off. The obtained precipitate was pulped twice with 500 parts of ethanol and twice with 500 parts of dimethyl sulfoxide, to obtain a yellow solid. The said yellow solid was dried at 60 degreeC under reduced pressure, and 4.5 parts of compounds (henceforth "compound (1-1)") represented by Formula (1-1) were obtained.

Identification of the compound represented by formula (1-1);

(Elemental Analysis) C 70.84 H 3.28 N 4.75 S 5.09

[Example 2]

53.26 parts of sulfolane was added to 7.00 parts of the compound represented by the formula (VII-1), and then heated to dissolve at 180 ° C. After dissolution was confirmed, 13.88 parts of 8-chloroquinaldine was added and refluxed at 200 ° C. for 9 hours. After the reaction was completed, the reaction solution was poured into 500 parts of acetonitrile and the precipitate was filtered off. The obtained precipitate was pulped twice with 500 parts of ethanol and twice with 500 parts of dimethyl sulfoxide, to obtain a yellow solid. The said yellow solid was dried at 60 degreeC under reduced pressure, and 8.15 parts of compounds (henceforth "compound (1-266)") represented by a formula (1-26) were obtained.

Identification of the compound represented by formula (1-26);

(Elemental Analysis) C 63.3 H 2.8 N 3.8 Cl 10.2 S 5.0

[Example 3]

92.65 parts of sulfolane was added to 10.0 parts of compounds (manufactured by Tokyo Kasei Co., Ltd.) represented by the formula (VII-2), and then heated to dissolve at 180 ° C. After confirming dissolution, 24.15 parts of quinaldine was added and refluxed at 200 ° C. for 9 hours. After the reaction was completed, the reaction solution was poured into 500 parts of acetonitrile and the precipitate was filtered off. The obtained precipitate was pulped twice with 500 parts of ethanol and twice with 500 parts of dimethyl sulfoxide, to obtain a yellow solid. The said yellow solid was dried at 60 degreeC under reduced pressure, and 13.5 parts of compounds (henceforth "compound (1-447)") represented by Formula (1-447) were obtained.

Identification of the compound represented by formula (1-4);

(Elemental Analysis) C 79.97 H 3.68 N 5.31

Example 4

After adding 64.86 parts of sulfolane to 7.0 parts of the compound represented by the formula (X2), it was heated to dissolve at 180 ° C. After confirming dissolution, 16.90 parts of 8-chloroquinaldine was added and refluxed at 200 ° C. for 9 hours. After the reaction was completed, the reaction solution was poured into 500 parts of acetonitrile and the precipitate was filtered off. The obtained precipitate was pulped twice with 500 parts of ethanol and twice with 500 parts of dimethyl sulfoxide, to obtain a yellow solid. The said yellow solid was dried at 60 degreeC under reduced pressure, and 9.0 parts of compounds (henceforth "compound (1-77)") represented by Formula (1-7) were obtained.

Identification of the compound represented by formula (1-7);

(Elemental Analysis) C 68.5 H 3.0 N 3.6 Cl 10.4

[Heat resistance evaluation]

With respect to the compound obtained in the example, a differential thermal thermogravimetric simultaneous measuring apparatus [EXSTAR TG / DTA6200R; SII and using nanotechnology (Co., Ltd.)] and subjected to differential scanning calorimetry, the temperature T ₁₀ was determined to be a weight reduction of 10%. The results are shown in Table 2.

In Table 2, the chemical substance (R? 1) is CI Acid Yellow 3 (manufactured by Tokyo Kasei Co., Ltd.).

[Example 5]

[Preparation of coloring composition]

(A) Colorant: Compound (1-1): 20 parts of compound synthesized in Example 1

(Iii) Resin: methacrylic acid / benzyl methacrylate copolymer (molar ratio; 30/70, weight average molecular weight; 10700, acid value; 70 mgKOH / g) 70 parts

(C? 1) Polymerizable compound: 30 parts of dipentaerythritol hexaacrylate (manufactured by Nihon Kayaku Co., Ltd.)

(D? 1) Photoinitiator: 15 parts of benzyl dimethyl ketal (a monocure 651; BASF Corporation make)

(E? 1) Solvent: 680 parts of propylene glycol monomethyl ether

It mixed and obtained the coloring composition.

[Production of color filter]

The coloring composition obtained above is apply | coated by the spin coating method on glass, and a volatile component is volatilized. After cooling, light irradiation is performed using a quartz glass photomask and an exposure machine. After light irradiation, it develops with aqueous potassium hydroxide solution and heats to 200 degreeC in oven, and obtains a color filter.

[Example 6]

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

[Example 7]

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

[Example 8]

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

From the results in Table 2, it was found that the compounds of the present invention exhibit high heat resistance. The coloring composition containing the said compound has little deterioration by heat, and can manufacture a color filter with high durability.

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

Claims (7)

Formula (1)

In the formula ^(1), L 1 represents a single bond, -SO ₂ - or denotes a -CO-. A ¹ and A ² each independently 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. The method of claim 1,
The said A ¹ and A ² are the benzene rings which may have a substituent independently of each other. The method of claim 1,
The substituent is -R ¹ , -OR ¹ , -COR ¹ , -O-COR ¹ , C1-8 fluorinated alkyl group, halogeno group, hydroxy group, sulfanyl group, sulfo group, carboxyl group, nitro group, formyl group , -NHR ¹ and -NR ¹ R ² , provided that R ¹ and R ² represent an alkyl group having 1 to 8 carbon atoms. The method of claim 1,
Wherein A ¹ and A ² are independently an unsubstituted benzene ring or a benzene ring having a halogeno group. The method of claim 1,
A ¹ and A ² are the same compound. The method of claim 1,
L ¹ is a single bond or —SO ₂ —. The coloring composition containing the compound of Claim 1.