Green electroluminescent compounds and organic electroluminescent device using the same

A compound, electroluminescence technology, applied in the direction of electroluminescence light source, preparation of organic compounds, electric solid devices, etc., can solve the problem of unconfirmed material properties, etc., to achieve high efficiency and electroluminescence properties, high performance electroluminescence properties , the effect of long-life electroluminescence properties

Inactive Publication Date: 2008-08-13
GRACEL DISPLAY INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] However, U.S. Patent 6,465,115 does not use Compound K and Compound L in the light-emitting region, and does not confirm the properties of those materials in the light-emitting region

Method used

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  • Green electroluminescent compounds and organic electroluminescent device using the same
  • Green electroluminescent compounds and organic electroluminescent device using the same
  • Green electroluminescent compounds and organic electroluminescent device using the same

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0083] [Preparation example 1] compound (1) (chemical formula 1: R 1 = R 2 = 2-naphthyl, R 3 = R 4 = R 5 = R 6 = phenyl) preparation

[0084] 2,6-Dichloroanthraquinone (1.0 g, 3.6 mmol) and diphenylamine (1.3 g, 7.7 mmol) were dissolved in anhydrous toluene, and palladium acetate (Pd(OAc) 2 ) (2.4g, 24.4mmol), tri-tert-butylphosphine (P(t-Bu) 3 ) (0.2 mL, 1.9 mmol) and sodium tert-butoxide (t-BuONa) (0.93 g, 9.7 mmol). The resulting mixture was heated to reflux at 110°C for 3 days. When the reaction was complete, 10 mL of distilled water was added, and the mixture was stirred for 30 minutes. The resulting solid was filtered off, washed with solvents such as acetone and THF, dried and recrystallized from dichloromethane to give bis(2,6-diphenylamino)anthraquinone (1.1 g, 2.0 mmol, yield: 56 %).

[0085]A solution of 2-naphthyllithium in diethyl ether (5 mL) previously prepared by using diphenylamine (0.74 g, 4.4 mmol) and n-butyllithium (n-BuLi) (1.8 mL, 4.5 mmol, 2.5...

preparation example 2

[0089] [Preparation example 2] compound (2) (chemical formula 1: R 1 =R 2 =R 3 =R 5 = 2-naphthyl, R 4 =R 6 = phenyl) preparation

[0090] Repeat the same process as described in Preparation Example 1, but use N-phenyl-2-naphthylamine (1.7g, 7.8mmol), thereby obtaining compound (2) (0.53g, 0.61mmol, total yield: 17 %).

[0091] 1 H NMR (200MHz, CDCl 3 ): δ6.45(d, 4H), 6.6(t, 2H), 6.75-6.8(m, 8H), 7.0-7.15(m, 6H), 7.2-7.3(m, 6H), 7.45-7.6(m , 10H), 7.65-7.8(m, 6H), 7.9(s, 2H)

[0092] MS / FAB: 864 (measured value), 865.10 (calculated value)

preparation example 3

[0093] [Preparation example 3] compound (3) (chemical formula 1: R 1 =R 2 = 2-naphthyl, R 3 =R 5 = 1-naphthyl, R 4 =R 6 = phenyl) preparation

[0094] Repeat the same process as described in Preparation Example 1, but use N-phenyl-1-naphthylamine (1.7g, 7.8mmol), thereby obtaining compound (3) (0.41g, 0.47mmol, total yield: 13 %).

[0095] 1 H NMR (200MHz, CDCl 3 ): δ6.45(d, 4H), 6.5(d, 2H), 6.6(t, 2H), 6.75-6.8(m, 4H), 7.0-7.05(m, 4H), 7.15-7.2(m, 4H ), 7.3-7.35(m, 8H), 7.55-7.8(m, 14H), 7.9(s, 2H)

[0096] MS / FAB: 864 (measured value), 865.10 (calculated value)

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Abstract

The present invention relates to organic electroluminescent compounds represented by Chemical Formula 1 or 2, a process for preparing the same, and an organic light emitting diode (OLED) which comprises, as a luminescent region interposed between an anode and a cathode, at least one compound (s) selected from those represented by Chemical Formula 1 or 2, and at least one compound selected from anthracene derivatives, benz[a]anthracene derivatives and naphthacene derivatives. The electroluminescent compound according to the present invention is a green electroluminescent compound having maximized electroluminescent efficiency and lifetime of device.

Description

technical field [0001] The present invention relates to an organic electroluminescent compound represented by Chemical Formula 1 or 2, a preparation method thereof, and an organic light emitting diode (OLED) comprising at least one compound selected from the compound represented by Chemical Formula 1 or 2 and an anthracene derivatives, benzanthracene derivatives and tetracene derivatives as a light-emitting region interposed between the anode and the cathode. [0002] [chemical formula 1] [0003] [0004] [chemical formula 2] [0005] Background technique [0006] The most important thing to develop OLEDs with high efficiency and long lifetime is to develop high-performance electroluminescent materials. From the current development of electroluminescent materials, green electroluminescent materials show electroluminescent properties superior to red or blue electroluminescent materials. However, conventional green electroluminescent materials still have many problem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
CPCC09B1/32C09K2211/1011H01L51/5012C07C2103/50C09B57/008H01L51/006C09B3/02C07C217/92H01L51/0052C07C2103/24C07C2103/40C07C211/61C09K2211/1007C09K11/06C09B1/00C09B3/14C09B57/001H05B33/14C09K2211/1014H01L51/0081C07C2103/18C07C2603/18C07C2603/24C07C2603/40C07C2603/50H10K85/633H10K85/615H10K85/324H10K50/11
Inventor 玄承学李在成柴商晚韩根熙权赫柱赵英俊尹胜洙金奉玉金圣珉金侈植崔日圆
Owner GRACEL DISPLAY INC
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