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Aromatic Amine Derivative and Organic Electroluminescent Device Using Same

Inactive Publication Date: 2008-12-11
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0040]An aromatic amine and an organic EL device using the aromatic amine derivative of the present inventions which hardly cause the crystallization of a molecule, can improve yields upon production of the organic EL device, and can increase the lifetime of the organic EL device.

Problems solved by technology

In general, when an organic EL device is driven or stored in an environment of a high temperature, adverse effects such as a change in the luminescent color, a decrease in emission efficiency, an increase in the voltage for driving, and a decrease in the lifetime of light emission arise.
As a results there arises a problem such as the clogging of the outlet of a crucible to be used in vapor deposition or a reduction in yields of the organic EL device due to the generation of a fault of the thin film resulting from the crystallization.
Accordingly, there arises a problem in that the lifetime of the compound is short because a phenomenon such as decomposition at the time of vapor deposition or the formation of a nonuniform deposition film is expected to occur.
In addition, none of those patents explicitly describes a method of producing an asymmetric compound in spite of the fact that the asymmetric compound requires a special synthesis method.
As a result, they have found that a problem lies in the short lifetime of the device.
As described above an organic EL device having a long lifetime has been reported, but it cannot be said yet that the device always shows sufficient performance.

Method used

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  • Aromatic Amine Derivative and Organic Electroluminescent Device Using Same
  • Aromatic Amine Derivative and Organic Electroluminescent Device Using Same
  • Aromatic Amine Derivative and Organic Electroluminescent Device Using Same

Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Synthesis of Intermediate 1

[0206]20.0 g of 4-bromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.) 8.64 g of sodium t-butoxide (manufactured by Wako Pure Chemical Industries, Ltd.), and 84 mg of palladium acetate (manufactured by Wake Pure Chemical Industries, Ltd.) were loaded into a 200-mL three-necked flask. Further, a stirring rod was placed in the flask, and rubber caps were set on both side ports of the flask. A reflux condenser was inserted into the central port of the flasks and a three-way cock and a balloon in which an argon gas was sealed were set above the condenser. The inside of the system was replaced with the argon gas in the balloon three times by using a vacuum pump.

[0207]Next 120 mL of dehydrated toluene (manufactured by HIROSHIMA WAKO CO., LTD.), 4.08 mL of benzylamine (manufactured by TOKYO CHEMICAL INDUSTRY CO. LTD.) and 338 μL of tri-t-butylphosphine (manufactured by SIGMA-ALDRICH, 2.22-mol / L toluene solution) were added to the flask by using a syr...

synthesis example 2

Synthesis of Intermediate 2

[0214]In a stream of argon, 10 g of di-4-biphenylylamine, 9.7 g of 4,4-dibromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), 3 g sodium t-butoxide manufactured by HIROSHIMA WAKO CO., LTD.), 0.5 g of bis(triphenylphosphine)palladium(II) chloride (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), and 500 mL of xylene were loaded, and the whole was subjected to a reaction at 130° C. for 24 hours.

[0215]After the resultant had been cooled, 1,000 mL of water were added to the resultant, and the mixture was subjected to Celite filtration. The filtrate was extracted with toluene and dried with anhydrous magnesium sulfate. The dried product was condensed under reduced pressure, and the resultant crude product was subjected to column purification. The purified product was recrystallized with toluene. The crystal was taken by filtration, and was then dried, whereby 4.6 g of 4′-bromo-N,N-dibiphenylyl-4-amino-1,1′-biphenyl (Intermediate 2) shown below ...

synthesis example 3

Synthesis of Intermediate 3

[0216]In a stream of argon, 6.8 g of N-phenyl-1-naphthylamine (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD), 9.7 g of 4,4′-dibromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO. LTD.), 3 g of t-butoxy sodium (manufactured by HIROSHIMA WAKO CO. LTD.), 0.5 g of bis(triphenylphosphine)palladium(II) chloride (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), and 500 mL of xylene were loaded, and the whole was subjected to a reaction at 130° C. for 24 hours.

[0217]After the resultant had been cooled, 1,000 mL of water were added to the resultant, and the mixture was subjected to Celite filtration. The filtrate was extracted with toluene and dried with anhydrous magnesium sulfate. The dried product was condensed under reduced pressure, and the resultant crude product was subjected to column purification. The purified product was recrystallized with toluene. The crystal was taken by filtration, and was then dried, whereby 4.1 g of 4′-bromo-N-phenyl-N-...

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PUM

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Abstract

Disclosed is an organic electroluminescence device in which an organic thin film which is composed of one or more layers including at least a light-emitting layer is interposed between a cathode and an anode. Since at least one layer of the organic thin film contains a novel aromatic amine derivative, which has an asymmetric structure wherein two different amine units are bonded through a linking group, by itself or as a component of a mixture, molecules of the organic electroluminescence device. This organic electroluminescence device has a long life.

Description

TECHNICAL FIELD[0001]The present invention relates to aromatic amine derivatives and an organic electroluminescence (EL) device using any one of them, in particular an organic EL device in which a molecule hardly crystallizes, which is produced with improved yields, and which has a long lifetime and an aromatic amine derivative realizing the organic EL device.BACKGROUND ART[0002]An organic EL device is a spontaneous light emitting device which utilizes the principle that a fluorescent substance emits light by energy of recombination of holes injected from an anode and electrons injected from a cathode when an electric field is applied. Since an organic EL device of the laminate type driven under a low electric voltage was reported by C. W. Tang et al. of Eastman Kodak Company (C. W. Tang and S. A. Vanslyke, Applied Physics Letters, Volume 51, Pages 913, 1987 or the like) many studies have been conducted on or organic EL devices using organic materials as the constituent materials. T...

Claims

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Application Information

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IPC IPC(8): H01L51/54C07C211/54
CPCC07C211/54Y10S428/917C07C211/61C07C2103/18C07C2103/26C07C2103/50C07C2103/97C09K11/06C09K2211/1007C09K2211/1011H01L51/0058H01L51/006H01L51/0062H01L51/0081H01L51/5012H01L51/5048H05B33/14H05B33/20C07C211/58C07C2603/18C07C2603/26C07C2603/50C07C2603/97H10K85/649H10K85/626H10K85/633H10K85/324H10K50/14H10K50/11
Inventor YABUNOUCHI, NOBUHIROKAWAMURA, HISAYUKI
Owner IDEMITSU KOSAN CO LTD
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