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Novel materials for organic electroluminescent devices

A general formula and compound technology, applied in the field of new materials for organic electroluminescent devices, can solve problems such as insufficient thermal stability, difficult processing, synthesis and processing

Active Publication Date: 2009-07-22
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 1. According to the prior art, many dopants can only be obtained by complex multi-stage synthesis methods
[0004] 2. The lifetime of organic electroluminescent devices according to the prior art is still insufficient for high-quality applications
[0005] 3. Insufficient thermal stability, especially for many blue dopants
[0006] 4. According to the prior art, many compounds, especially the blue dopant, are highly sensitive to oxygen and light, making their synthesis and handling quite difficult
However, these also do not have satisfactory device performance, especially with regard to lifetime and with regard to operating voltage
Moreover, these compounds are sensitive to oxygen and light, making their handling more difficult, especially on an industrial scale

Method used

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  • Novel materials for organic electroluminescent devices
  • Novel materials for organic electroluminescent devices
  • Novel materials for organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0200] Example 1: 5,5'-Dibromo-peridoxanthene and xanthene

[0201]

[0202] A suspension of 28.2 g (100 mmol) of per-xanthenoxanthene and 36.5 g (205 mmol) of N-bromosuccinimide in 200 ml of o-dichlorobenzene was stirred at 180° C. for 6 hours. After cooling, the solid was filtered off with suction, washed five times with 200 ml of ethanol each time and dried in vacuo. The crude product was recrystallized twice from ortho-dichlorobenzene, yielding 41.4 g (94 mmol) of 5,5'-dibromo-peri-xanthene-xanthene, corresponding to 94.0% of theory, with a purity of 99.0% according to HPLC.

Embodiment 2

[0203] Example 2: 5,5',7,7'-tetrabromo-peridoxanthene and xanthene

[0204]

[0205] A suspension of 28.2 g (100 mmol) of per-xanthenoxanthene and 73.0 g (410 mmol) of N-bromosuccinimide in 300 ml of o-dichlorobenzene was stirred at 180° C. for 16 hours. After cooling, the solid was filtered off with suction, washed five times with 200 ml of ethanol each time and dried in vacuo. The crude product was recrystallized twice from o-dichlorobenzene to give 55.0 g (92 mmol) of 5,5',7,7'-tetrabromo-peridoxanthene and xanthene, corresponding to 92.0% of theory, according to HPLC The purity is 99.0%.

Embodiment 3

[0206] Example 3: 3,3', 5,5', 7,7'-hexabromo-peri-xanthene and xanthene

[0207]

[0208] A suspension of 28.2 g (100 mmol) of per-xanthenoxanthene and 142.4 g (800 mmol) of N-bromosuccinimide in 500 ml of o-dichlorobenzene was stirred at 180° C. for 28 hours. After cooling, the solid was filtered off with suction, washed five times with 200 ml of ethanol each time and dried in vacuo. The crude product was purified three times with boiling o-dichlorobenzene to obtain 72.5 g (96 mmol) of 3,3',5,5',7,7'-hexabromo-peridoxanthene and xanthene, corresponding to 96.0 of theoretical value %, 99.0% purity according to HPLC.

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Abstract

The present invention relates to compounds according to formulas (1) to (8) and to the use thereof in organic electroluminescent devices, in particular in blue-emitting devices. The compounds according to formulas (1) to (8) are used as host material or as a dopant in the emitting layer, or in a hole transport layer or electron transport layer.

Description

field of invention [0001] The present invention relates to organic semiconductors and their use in organic electronic devices. Background technique [0002] Organic semiconductors are being developed for many different applications in the broadest sense attributed to the electronics industry. Structures of organic electroluminescent devices (OLEDs) in which these organic semiconductors are used as functional materials are described, for example, in US 4539507, US 5151629, EP 0676461 and WO 98 / 27136. However, these devices still have considerable problems that need urgent improvement: [0003] 1. According to the prior art many dopants are only obtainable in complex multistage synthesis methods. [0004] 2. The lifetime of organic electroluminescent devices according to the prior art is still insufficient for high-quality applications. [0005] 3. Insufficient thermal stability, especially of many blue dopants. [0006] 4. According to the prior art, many compounds, espec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C15/38H05B33/14C07D311/82
CPCC07C2103/54C09K2211/1011H01L51/0061Y10S428/917H01L51/006C07C43/275C09K11/06C07C13/62C07C2103/24C07C211/61H05B33/14C07C2103/94H01L51/0073C07D311/82C07D493/06C07C49/792C09K2211/1088C07C2603/24C07C2603/54C07C2603/94H10K85/636H10K85/633H10K85/6574C07C15/38
Inventor 菲利普·施特塞尔阿尔内·比辛霍尔格·海尔
Owner MERCK PATENT GMBH
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