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Organic electroluminescence device

a technology of electroluminescence device and organic material, which is applied in the direction of solid-state devices, discharge tubes/lamp details, natural mineral layered products, etc., can solve the problems of insufficient efficiency of light emission, insufficient average life of less than 150 hours, and device with insufficient purity of red light, etc., to achieve excellent color purity and high light emission efficiency

Inactive Publication Date: 2007-01-04
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0005] The present invention has been made to overcome the above problems and has an object of providing an organic EL device which exhibits an excellent purity of color and a high efficiency of light emission, has a long life and emits reddish light and a novel compound having these characteristics.

Problems solved by technology

Although this device exhibits an excellent purity of red light, the device exhibits an efficiency of light emission as low as 0.7 lm / W and has an insufficient average life which is shorter than 150 hours.
However, this device exhibits an insufficient purity of red light.
The efficiency of light emission is as small as 4 cd / A or smaller and insufficient.

Method used

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  • Organic electroluminescence device
  • Organic electroluminescence device
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Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Compound A-1

[0060] 3,10- and 3,11-Bisdiphenylamino-7,14-diphenylacenaphtho[1,2-k]fluoranthene was synthesized via the reaction route shown in the following:

[0061] (A) Synthesis of 3,10- and 3,11-dibromo-7,14-diphenylacenaphtho[1,2-k]fluoranthenes

[0062] In accordance with the J. B. Allen's process, 3,10- and 3,11-dibromo-7,14-diphenylacenaphtho[1,2-k]fluoranthenes (7) were synthesized using acenaphthenequinone (1) as the starting material via 7,14-diphenylacenaphtho[1,2-k]fluoranthene (6). The structures of 3,10- and 3,11-dibromo-7,14-diphenylacenaphtho[1,2-k]fluoranthenes were identified from FD-MS (the field desorption mass spectra) and the 1H-NMR spectra. The chemical shifts in 1H-NMR agreed with the measured values reported by Allen (J. D. Debad, A. I. Bard, J. Chem. Soc., Vol. 120, 2476 (1998)).

[0063] (B) Synthesis of 3,10- and 3,11-diphenylamino-7,14-diphenylacenaphthofluoranthenes (Compound A-1)

[0064] Into 150 ml of toluene, 3.56 g (5.6 mmole) of 3,10- and 3,11-dibromo-7...

synthesis example 2

Compound A-16

[0066] The reaction was conducted in accordance with the same procedures as those conducted in Synthesis Example 1 (B) except that 2.31 g (11.7 mmole) of p,p′-ditolylamine was used in place of diphenylamine. After the reaction was completed, the reaction mixture was filtered. The filtrate was washed with water and concentrated and a red powdery solid was obtained. The obtained solid was fractionated in accordance with the column chromatography using a column packed with silica gel and 2.9 g of the main component having a high purity was obtained. The main component was confirmed to be Compound A-16 from FD-MS (868).

synthesis example 3

Compound B-15

[0067] The reaction was conducted in accordance with the same procedures as those conducted in Synthesis Example 1 (B) except that 2.27 g (11.7 mmole) of iminostilbene was used in place of diphenylamine. After the reaction was completed, the product precipitated in the reaction mixture was separated, repeatedly washed with acetone and water and dried and 3.4 g of a red orange powdery solid was obtained. The obtained solid was dissolved in tetrahydrofuran and fractionated in accordance with the thin layer chromatography using a thin layer of silica gel and 2.3 g of the main component having a high purity was obtained. The main component was confirmed to be Compound B-15 from FD-MS (862).

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Abstract

An organic electroluminescence device which exhibits an excellent purity of color and a high efficiency of light emission, has a long life and emits reddish light and a novel compound having these characteristics are provided. The organic electroluminescence device comprises an organic layer disposed between at least one pair of electrodes, wherein the organic layer comprises a compound having a fluoranthene skeleton structure substituted at least with an amine group or an alkenyl group.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescence device which is used as a light source such as a planar light emitting member of televisions and a back light of displays, exhibits an excellent purity of color and a high efficiency of light emission, has a long life and emits reddish light and to a novel compound having these characteristics. BACKGROUND ART [0002] Electroluminescence (referred to as EL, hereinafter) 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 side of the anode. The electrons are ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H01L51/54H05B33/12C07C13/62C07C211/61C07C217/92C07C217/94C07C229/68C07C255/42C07C255/58C07D219/14C07D223/14C07D223/26C07D223/28C07D279/26C07D295/02C07D295/135C07D295/155C07D471/06C09K11/06H01L51/00H01L51/30H01L51/50
CPCC07C13/62Y10S428/917C07C211/61C07C217/92C07C217/94C07C229/68C07C255/42C07C255/58C07C2101/14C07C2103/54C07D219/14C07D223/14C07D223/26C07D223/28C07D279/26C07D295/02C07D295/135C07D295/155C07D471/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1037H01L51/0054H01L51/0056H01L51/0059H01L51/006H01L51/0081H01L51/5012H01L51/5048H05B33/14C07C13/70C07C2601/14C07C2603/54H10K85/622H10K85/624H10K85/633H10K85/631H10K85/324H10K50/14H10K50/11H10K85/636H10K85/615
Inventor TAGAMI, SANAEIKEDA, HIDETSUGUHOSOKAWA, CHISHIOARAKANE, TAKASHI
Owner IDEMITSU KOSAN CO LTD
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