Electron transport type red light phosphorescent material, preparation method and organic electroluminescent device thereof

An electron transport and phosphorescent material technology, applied in luminescent materials, electro-solid devices, organic chemistry, etc., can solve the problems of high driving voltage, unfavorable carrier injection and transport balance, low luminous efficiency, etc., and achieve good thermal stability. properties, enhanced electron transport performance, and high luminous efficiency

Inactive Publication Date: 2014-12-03
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, efficient red phosphorescent devices are rare, mainly due to the lack of suitable host materials.
[0003] At present, the host material widely used in red phosphorescent devices is CBP (4,4'-bis(9-carbazole)biphenyl), but it requires high driving voltage and glass transition temperature (T g ) Low (T g =62℃), easy to crystallize
In addition, CBP is a p-type material, the hole mobility is much higher than the electron mobility, which is not conducive to the balance of carrier injection and transport, and the luminous efficiency is low

Method used

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  • Electron transport type red light phosphorescent material, preparation method and organic electroluminescent device thereof
  • Electron transport type red light phosphorescent material, preparation method and organic electroluminescent device thereof
  • Electron transport type red light phosphorescent material, preparation method and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The preparation steps of the electron transport type red phosphorescent material in this embodiment are as follows:

[0046]

[0047] The first step: under nitrogen protection, 2,2'-oxydibromobenzene (26.2g, 80mmol) was dissolved in 200mLN,N-dimethylformamide (DMF) solution, then added thiophenol (17.6 g, 160mmol), potassium carbonate (22.1g, 160mmol), cuprous iodide (1.52g, 8mmol). The mixture was stirred and reacted at 120°C for 6 hours. Stop the reaction and cool to room temperature, filter, and wash the solid three times with distilled water. The crude product is separated by silica gel chromatography column using eluent n-hexane to obtain off-white structural formula: solid product. The yield was 85%.

[0048]The second step: under ice-water bath, dissolve C (15.4g, 40mmol) in 120mL of dichloromethane (DCM) solution, and then drop it into 90mL of m-chlorobenzoic acid (mCPBA) (2mol / L) di in methyl chloride solution. After the mixture was stirred and reacted...

Embodiment 2

[0051] The preparation steps of the electron transport red phosphorescent material of this embodiment are as follows:

[0052]

[0053] Step 1: Under nitrogen protection, dissolve 2,2'-oxydibromobenzene (26.2g, 80mmol) in 200mL toluene (Tol) solution, then add thiophenol (19.4g, 176mmol), cesium carbonate (57.2g, 176mmol), copper powder (0.768g, 12mmol). The mixture was stirred and reacted at 110°C for 9 hours. Stop the reaction and cool to room temperature, filter, and wash the solid three times with distilled water. The crude product is separated by silica gel chromatography column using eluent n-hexane to obtain off-white structural formula: solid product. The yield was 89%.

[0054] The second step: the step is the same as the second step in Example 1.

Embodiment 3

[0056] The preparation steps of the electron transport red phosphorescent material of this embodiment are as follows:

[0057]

[0058] Step 1: Under nitrogen protection, dissolve 2,2'-oxydibromobenzene (26.2g, 80mmol) in 200mL acetonitrile (MeCN) solution, then add thiophenol (21.1g, 192mmol), potassium phosphate (39g, 184mmol), cuprous oxide (2.3g, 16mmol). The mixture was stirred and reacted at 90°C for 12 hours. Stop the reaction and cool to room temperature, filter, and wash the solid three times with distilled water. The crude product is separated by silica gel chromatography column using eluent n-hexane to obtain off-white structural formula: solid product. The yield was 86%.

[0059] The second step: the step is the same as the second step in Example 1.

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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses an electron transport type red light phosphorescent material, a preparation method and an organic electroluminescent device thereof. The structural formula of the material is shown as the specification. The electron transport type red light phosphorescent material provided by the invention has strong electron transport capability and good carrier transport balance. Also the material has a high triplet state energy level, and can effectively prevent back transmission of energy to a host material in a luminescence process. Thus, the luminescence efficiency is high.

Description

technical field [0001] The invention relates to an organic semiconductor material, in particular to an electron transport type red phosphorescent material and a preparation method thereof. The invention also relates to an organic electroluminescent device in which the material of the light-emitting layer adopts the electron-transporting red phosphorescence material as a main body material. Background technique [0002] Organic electroluminescent devices have the advantages of low driving voltage, fast response speed, wide viewing angle range, rich colors through fine-tuning of chemical structure, easy realization of high resolution, light weight, and large-area flat-panel display. 21st Century Flat Panel Display Technology" has become a research hotspot in the fields of materials, information, physics and flat panel display. Future efficient commercial OLEDs will likely contain organometallic phosphors because they can trap both singlet and triplet excitons, thereby achievi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C317/22C07C315/02H01L51/54
Inventor 周明杰张振华王平黄辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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