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Method for producing aromatic compound and aromatic compound

a technology of aromatic compounds and compounds, applied in the direction of discharge tubes/lamp details, organic chemistry, discharge tubes/lamp details, etc., can solve the problems of insufficient reduction of luminance and initial current efficiency, inability to reduce the contents of bromine compounds and iodine compounds in accordance with conventional processes, and impurities in used materials greatly affect the properties of organic el devices, etc., to achieve the effect of increasing the life of the organic el devi

Inactive Publication Date: 2009-08-20
IDEMITSU KOSAN CO LTD
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  • Abstract
  • Description
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AI Technical Summary

Benefits of technology

[0012]In accordance with the present invention, an aromatic compound having contents of halogen elements of 10 ppm by mass or smaller can be obtained. By using the aromatic compound as the material for an organic EL device, the life of the organic EL device can be increased.THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION
[0013]The process for producing an aromatic compound comprises bringing an aromatic compound which is produced via an intermediate compound having halogen elements and has contents of halogen elements of 10 to 1,000 ppm by mass into further reaction with a dehalogenating agent to decrease the contents of halogen elements to 10 ppm by mass or smaller. The above reaction is the treatment of making aromatic halogen compounds as the impurities in the aromatic compound obtained by the synthesis harmless by converting the aromatic halogen compounds into other compounds.
[0014]As the process for converting aromatic halogen compounds into other compounds, conventional reactions using a dehalogenating agent can be used. Grignard reactions, reactions using organolithium compounds and reactions using boronic acid derivatives (Suzuki coupling reactions) are preferable due to the great yield of the reaction.
[0015]The Grignard reaction is a coupling reaction between an aromatic halogen compound and a Grignard reagent. As the Grignard reagent, a commercial reagent or an arylmagnesium bromide, an arylmagnesium iodide, an alkylmagnesium bromide or an alkylmagnesium iodide which is suitably prepared can be used. Among the above reagents, phenyl-magnesium bromide, phenylmagnesium iodide, ethylmagnesium bromide and ethylmagnesium iodide are preferable. Phenylmagnesium bromide and phenylmagnesium iodide are more preferable. The Grignard reagent may be used singly or in combination of two or more.
[0016]As the solvent for the reaction, a conventional solvent can be used. Specifically, ether-based solvents such as dimethoxyethane and tetrahydrofuran are preferable. A mixed solvent of these solvents may be used. It is desirable that the solvent for the reaction is treated for dehydration in advance.
[0017]The temperature of the reaction is selected, in general, in the range of −30 to 100° C. and preferably in the range of −10 to 80° C. The time of the reaction is selected, in general, in the range of 1 to 48 hours and preferably in the range of 2 to 8 hours. It is preferable that the reaction in conducted under a stream of argon.

Problems solved by technology

It is known that impurities in the used material greatly affect the properties of organic EL devices such as the decrease in the luminance and the initial current efficiency.
However, the contents of bromine compounds and iodine compounds cannot be decreased sufficiently in accordance with conventional processes.

Method used

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  • Method for producing aromatic compound and aromatic compound
  • Method for producing aromatic compound and aromatic compound
  • Method for producing aromatic compound and aromatic compound

Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Synthesis of 9-(naphthyl-2-yl)-10-(4-(naphthyl-1-yl)phenyl-1-yl)anthracene (BH1)

(1) Synthesis of 9-(naphthyl-2-yl)anthracene

[0127]Under the stream of nitrogen, 30.0 kg of 9-bromoanthracene (manufactured by Tokyo Chemical Industry Co., Ltd.), 24.1 kg of 2-naphthylboronic acid, 2.157 kg of tetrakis(triphenylphosphine)palladium, 48.4 kg of potassium carbonate (manufactured by NIPPON SODA Co., Ltd.), 150 liters of toluene and 150 liters of Solmix were placed into a 1,000 liter reactor, and the reaction was allowed to proceed at 78° C. for 50 hours.

[0128]After the reaction mixture was cooled to the room temperature, 188 liters of tetrahydrofuran and 188 liters of water were added, and the obtained mixture was fractionated. The obtained organic layer was washed with 115 liters of a 5% by mass aqueous solution of sodium hydroxide, 115 liters of a 5% by mass aqueous solution of sodium hydrogencarbonate and 115 liters of a 5% by mass aqueous solution of sodium chloride, successively, and the...

example 1

Treatment of BH1 by the Grignard Reaction

[0140]Under the stream of argon, 600 g of BH1 was suspended in 9 liters of anhydrous tetrahydrofuran (THF). To the resultant suspension, 60 ml of a 32% by mass tetrahydrofuran solution of phenylmagnesium bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) was slowly added dropwise under cooling with ice, and the obtained mixture was stirred at 50 to 60° C. for 30 minutes. To the obtained mixture, a dilute sulfuric acid was added to decompose the unreacted substances. The reaction product was treated by extraction with toluene, and the organic layer was washed with a 5% by mass aqueous solution of NaOH, a 5% by mass aqueous solution of sodium hydrogencarbonate and a 10% by mass aqueous solution of sodium chloride and concentrated under a reduced pressure. Toluene was added to the residue of the concentration to form a material fluid. The material fluid was purified using a column packed with silica gel and alumina, and the obtained flu...

example 2

Treatment of BH1 by the Reaction with an Organolithium Reagent

[0143]Under purging with nitrogen, 600 g of BH1 was dissolved into 5 liters of anhydrous toluene and 5 liters of anhydrous ether. To the obtained solution, 75 ml of a 15% by mass hexane solution of n-butyllithium (manufactured by Tokyo Chemical Industry Co., Ltd.) was slowly added at −78° C. The reaction mixture was stirred at 0° C. for 1 hour, and then the reaction was stopped by adding water. The reaction product was treated by extraction with toluene. The organic layer was washed with a 5% by mass aqueous solution of NaOH, a 5% by mass aqueous solution of sodium hydrogencarbonate and a 10% by mass aqueous solution of sodium chloride and then concentrated under a reduced pressure. Toluene was added to the residue of the concentration to form a material fluid. The material fluid was purified using a column packed with silica gel and alumina, and the obtained fluid was concentrated under a reduced pressure. When a slurry ...

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Abstract

A process for producing an aromatic compound which can effectively decrease the contents of halogen elements in the aromatic compound and an aromatic compound which is produced in accordance with the process and useful as the material for obtaining an organic electroluminescence device having a long life are provided. The process for producing an aromatic compound comprises bringing an aromatic compound which is produced via an intermediate compound having halogen elements and has contents of halogen elements of 10 to 1,000 ppm by mass into reaction with a dehalogenating agent to decrease the contents of halogen elements to 10 ppm by mass or smaller, and an aromatic compound which is produced in accordance with the process.

Description

TECHNICAL FIELD[0001]The present invention relates to a process for producing an aromatic compound useful as the organic material for electroluminescence and an aromatic compound obtained in accordance with the process. More particularly, the present invention relates to a process for producing an aromatic compound having decreased contents of halogen elements and an aromatic compound obtained in accordance with the process.BACKGROUND ART[0002]An organic electroluminescence device (hereinafter, referred to as an organic EL device occasionally) is a light emitting device having at least an organic light emitting layer disposed between a pair of electrodes. The energy generated by recombination of holes injected from the anode and electrons injected from the cathode in the light emitting layer is taken out in the form of light emission.[0003]The organic EL device is a device spontaneously emitting light. The organic EL device has various advantageous properties such as the great curre...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H01J1/63
CPCC07C7/173C07C209/84C09K11/06C09K2211/1011C09K2211/1014C07C15/28C07C211/54H01L2924/01003H01L2924/01111
Inventor MORIWAKI, FUMIOMATSUNAMI, HIDEHIROINOUE, TETSUYA
Owner IDEMITSU KOSAN CO LTD
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