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Organic electrolumescence device

an electroluminescence device and organic technology, applied in the direction of organic compounds/hydrides/coordination complex catalysts, organic/chemical process catalysts, anthracene dyes, etc., can solve the problems of low light emission efficiency, inferior luminance of emitted light, and low efficiency of light emission in comparison, and the properties of organic el devices deteriorate very rapidly

Inactive Publication Date: 2005-02-17
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention has been made to overcome the above problems and has an object to provide a material for organic electroluminescence devices, an organic electroluminescence device and a novel compound which exhibit high efficiency of light emission and have a long life and excellent heat resistance and a process for producing the material for organic electroluminescence devices.
It was further found by the present inventors that a tertiary arylamine which is a material for organic EL devices can be synthesized with a high activity by the reaction of an amine and an aryl halide in the presence of a catalyst comprising a phosphine compound and a palladium compound and a base. The present invention has been completed based on the above knowledge.

Problems solved by technology

Heretofore, organic EL devices require higher driving voltages and show inferior luminance of emitted light and inferior efficiencies of light emission in comparison with inorganic devices.
Moreover, properties of organic EL devices deteriorate very rapidly.
Therefore, heretofore, organic EL devices have not been used practically.
Although the properties of organic EL devices have been improved, organic EL devices exhibiting a sufficient efficiency of light emission and having sufficient heat resistance and life have not been obtained.
This material exhibits a marked decrease in the luminance of emitted light when the material is used at a high temperature for a long time and heat resistance is insufficient.
Moreover, these devices do not emit light in the region of orange to red color.
When these materials are used as the host material and other compounds are used as the doping material, a long life cannot be obtained.
However, this value has not been achieved.
However, in this example, the aluminum complex or the like emits light and the material for organic EL devices does not function as the light emitting center since the energy gap of the light emitting layer of the aluminum complex or the like is smaller than the energy gap of the material for organic EL devices.
However, the process using the Ullmann reaction has drawbacks in that an expensive iodide must be used as the reacting agent, that the reaction cannot be applied to many types of compounds, that the yield of the reaction is not sufficient, that the reaction requires a temperature as high as 150° C. and a long time and that waste liquid containing a great amount of copper is formed since copper powder is used in a great amount and environmental problems arise.

Method used

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  • Organic electrolumescence device
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Examples

Experimental program
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Effect test

synthesis example 1

Compound (2)

Synthesis of Intermediate Compound A

In a 200 ml round bottom flask, 0.38 g (2.04 mmole) of 4-bromobenzaldehyde and 0.98 g (4.29 mmole) of ethyl benzylphosphonate were dissolved in 40 ml of dimethylsulfoxide. To this was added 0.5 g (4.49 mmole) of potassium t-butoxide in small portions at the room temperature and the resulting mixture was stirred for 18 hours. The reaction mixture was poured into 500 ml of water, solid was filtered to give yellow solid (0.5 g).

In a 100 ml round bottom flask, the crystals obtained above, 2.0 g (12.0 mmole) of potassium iodide and 1.14 g (6.0 mmole) of copper iodide were dissolved in 10 ml of hexamethylphosphoramide and the resulting mixture was stirred under heating at 150° C. for 6 hours. After the reaction was completed, 10 ml of a 1 N aqueous hydrochloric acid was added to the reaction mixture and the organic layer was extracted with toluene. After the extract was concentrated, the reaction product was purified by recrystallizing...

synthesis example 2

Compound (9)

Synthesis of Intermediate Compound C

In a 200 ml round bottom flask, 51.2 g (0.3 mole) of diphenylamine, 71.4 g (0.3 mole) of 1,4-dibromobenzene, 34.6 g (0.36 mole) of potassium t-butoxide, 4.2 g (5.9 mmole) of PdCl2(PPh3)2 and 1.2 liter of xylene were mixed together and the obtained mixture was stirred at 130° C. for one night.

After the reaction was completed, the organic layer was concentrated and about 100 g of brown crystals were obtained. The crystals were purified in accordance with the column chromatography (silica gel, hexane / toluene=10 / 1) and 28 g (the yield: 29%) of the following Intermediate Compound C was obtained:

Synthesis of Compound (9)

In a 100 ml round bottom flask, 0.48 g (1 mmole) of Intermediate Compound B was dissolved in 10 ml of diethyl ether and the mixture was cooled to −78° C. To the cooled mixture, 2 ml (1.5 M, 3 mmole) of n-butyllithium was added and the resulting mixture was stirred for 1 hour. Then, a solution prepared by dissolving...

synthesis example 3

Compound (18)

Synthesis of Intermediate Compound D

A Grignard reagent was prepared by adding magnesium- and diethyl ether to 0.48 g (2.0 mmol) of 1,4-dibromobenzene. Separately, in a 100 ml round bottom flask, 5.7 g (20.0 mmole) of 1,4-dibromonaphthalene and 10 mg of NiCl2(dppp) were dissolved in 20 ml of diethyl ether and the resulting mixture was cooled in an ice bath. To the cooled mixture, the Grignard reagent prepared above was added and the obtained mixture was stirred under refluxing for 6 hours. After the reaction was completed, 10 ml of a 1 N aqueous hydrochloric acid was added. After the organic layer was separated, the solvent was removed by distillation and 0.30 (the yield: 30%) of the following Intermediate Compound D was obtained:

Synthesis of Compound (18)

In a 100 ml round bottom flask, 0.09 g (1.0 mmole) of aniline and 0.25 g (2.5 mmole) of acetic anhydride were dissolved into 5 ml of methylene chloride. The resulting mixture was stirred at the room temperature...

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Abstract

Materials for organic electroluminescence devices are represented by following general formula [1]: general formula [1]wherein A represents a chrysene group X1 to X4 each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, X1 and X2 may be bonded to each other, X3 and X4 may be bonded to each other, Y1 to Y4 each independently represent an organic group represented by general formula [2], a to d each represent an integer of 0 to 2 and, a+b+c+d≧0; general formula [2] being: general formula [2]wherein R1 to R4 each independently represent hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, cyano group or form a triple bond by a linkage of R1 and R2 or R3 and R4, Z represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and n represents 0 or 1.

Description

TECHNICAL FIELD The present invention relates to materials for organic electroluminescence devices which are used as a light source such as a planar light emitting member of televisions and a back light of displays, exhibit high efficiency of light emission and have excellent heat resistance and a long life, organic electroluminescence devices using the materials, novel compounds and processes for producing materials for electroluminescence devices. BACKGROUND ART Electroluminescence (EL) devices using organic compounds are expected to be used for inexpensive full color display devices of the solid light emission type which can display a large area and development thereof has been actively conducted. In general, an EL device is constituted with a light emitting layer and a pair of electrodes faced to each other at both sides of the light emitting layer. When a voltage is applied between the electrodes, electrons are injected at the side of the cathode and holes are injected at the...

Claims

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Application Information

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IPC IPC(8): C07C211/54C07C211/58C07C211/61C09K11/06H01L51/30H01L51/50
CPCB01J31/24Y10S428/917C07C211/58C07C211/61C07C2103/18C07C2103/24C07C2103/26C07C2103/44C07C2103/48C07C2103/52C09K11/06C09K2211/10C09K2211/1003C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1092H01L51/0042H01L51/005H01L51/0052H01L51/0054H01L51/0058H01L51/0059H01L51/006H01L51/0061H01L51/0068H01L51/007H01L51/0081H01L51/5012H01L51/5048H01L51/5088H01L2251/308H05B33/14C07C211/54C07C2603/18C07C2603/24C07C2603/26C07C2603/44C07C2603/48C07C2603/52C09B1/00C09B3/78C09B6/00C09B23/148C09B57/00C09B57/001C09B57/008H10K85/146H10K85/60H10K85/622H10K85/626H10K85/636H10K85/633H10K85/655H10K85/6565H10K85/615H10K85/631H10K85/324H10K50/14H10K50/17H10K50/11H10K2102/103H10K50/171
Inventor HOSOKAWA, CHISHIOFUNAHASHI, MASAKAZUKAWAMURA, HISAYUKIARAI, HIROMASAKOGA, HIDETOSHIIKEDA, HIDETSUGU
Owner IDEMITSU KOSAN CO LTD
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