Organic electroluminescent devices

An electronic device and general formula technology, applied in the field of organic electroluminescence devices, can solve the problem of not satisfying the disclosure and the like

Active Publication Date: 2011-05-25
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, devices containing blue-emitting triplet emitters that meet the technical requirements of industrial applications have not been disclosed so far.

Method used

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  • Organic electroluminescent devices
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1a

[0178] Example 1a: Synthesis of 1,4-bis(phosphonochloride)benzene:

[0179]

[0180] First 55.2 g (232 mmol) of 1,4-bis(phosphonic acid)benzene were added to 1400 ml of dichloromethane, followed by 10 drops of DMF. A solution of 86.3 ml (1020 mmol) of oxalyl chloride in 400 ml of dichloromethane was added dropwise at room temperature, and the mixture was stirred at 45° C. for 5 h. The solvent was removed under vacuum and the product was recrystallized from hexane under protective gas. Yield: 70 g (227 mmol), 98%.

[0181] The following compounds can be obtained similarly:

[0182]

Embodiment 2

[0183] Example 2: General Synthesis of N, N'-Diaryl-1,2-Phenylenediamine

[0184] 1.06g (4.75mmol) of Pd(OAC) 2 and 14.46 ml (14.46 mmol) of tri-tert-butylphosphine (1M solution in toluene) were added to 660 ml of degassed toluene, and the mixture was stirred for 5 minutes. Then 240 mmol of 1,2-dibromobenzene derivative, 505 mmol of arylamine and 67.22 g (700 mmol) of sodium tert-butoxide were added to the solution, which was then degassed and stirred again at 140 °C in a protective atmosphere 10h. After the solution was cooled, 600 ml of ammonium chloride solution and 150 ml of ethyl acetate were added, the phases were separated, washed with water, and washed with MgSO 4 Dry and evaporate. The solid was dissolved in toluene and filtered through celite. The crude product was stirred and washed with hot n-heptane.

Embodiment 3

[0185] Example 3: Synthesis of 4,5-dimethyl-N, N'-diphenyl-1,2-phenylenediamine

[0186]

[0187] According to Example 2, from 63.3 g (240 mmol) of 1,2-dibromo-4,5-xylene and 46 ml (505 mmol) of aniline, the synthesis was carried out according to the general procedure. The precipitated solid was recrystallized from toluene / acetonitrile (5:1), and the residue was washed with methanol to obtain 65 g (223 mmol) of a crystalline solid. The overall yield is 93%.

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Abstract

The present invention relates to electronic devices, particularly organic electroluminescent devices, which contain compounds according to the formula (1), and relates to the corresponding compounds and the use thereof in organic electroluminescent devices.

Description

technical field [0001] The present invention relates to organic electroluminescent devices and materials for organic electroluminescent devices. Background technique [0002] The structure of organic electroluminescent devices (OLEDs) in which organic semiconductors are used as functional materials is described, for example, in US 4539507, US 5151629, EP 0676461 and WO 98 / 27136. The luminescent materials used here are increasingly organometallic complexes which exhibit phosphorescence rather than fluorescence (M.A. Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6). Due to quantum mechanical reasons, it is possible to achieve up to a four-fold increase in energy and power efficiency using organometallic compounds as phosphorescent emitters. In general, however, there is still a need for improvements in OLEDs, especially OLEDs that also exhibit triplet emission, especially with regard to efficiency, operating voltage and lifetime. These improvements are especially suitable for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
CPCC09K2211/1011H01L51/50H01L51/0067H01L51/0071C09B57/10C07F9/65844C09K11/06C09B57/00C07F9/65848C09K2211/1007C09K2211/1055H01L51/5016C07F9/657181C07D401/04Y02E10/549Y10S428/917H10K85/654H10K85/657H10K50/11H10K2101/10
Inventor 菲利普·施特塞尔霍尔格·海尔多米尼克·约斯滕克里斯托夫·普夫卢姆安雅·格哈德埃斯特·布罗伊宁埃米尔·侯赛因·帕勒姆
Owner MERCK PATENT GMBH
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