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Tetraphenyl silicon-based blue light phosphorescent material and preparation method thereof and organic electroluminescent device

A technology of tetraphenyl silicon and phosphorescent materials, which is applied in the direction of luminescent materials, electric solid devices, organic chemistry, etc., can solve problems such as shortage, achieve good thermal stability, and improve 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, there are few efficient blue phosphorescent devices, mainly due to the lack of both good carrier transport performance and high triplet energy level (E T ) of the host material

Method used

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  • Tetraphenyl silicon-based blue light phosphorescent material and preparation method thereof and organic electroluminescent device
  • Tetraphenyl silicon-based blue light phosphorescent material and preparation method thereof and organic electroluminescent device
  • Tetraphenyl silicon-based blue light phosphorescent material and preparation method thereof and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The tetraphenylsilicon-based blue-light phosphorescent compound of this embodiment, that is, bis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)diphenylsilane, has the following structural formula:

[0041]

[0042] The preparation process of this compound is as follows:

[0043]

[0044] Under nitrogen protection, bis(4-bromophenyl)diphenylsilane (39.5g, 80mmol) was dissolved in 200mL N,N-dimethylformamide (DMF) solution, and then 3,6-di-tert-butyl Carbyl-9H-carbazole (44.7g, 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 column chromatography with eluent n-hexane, and then dried at 50°C for 24 hours under vacuum to obtain off-white solid bis(4-(3,6-di tert-Butyl-9H-carbazol-9-yl)phenyl)diphenylsilane. The yield was 79%. ...

Embodiment 2

[0047] The tetraphenylsilicon-based blue-light phosphorescent compound of this embodiment, that is, bis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)diphenylsilane, has the following structural formula:

[0048]

[0049] The preparation process of this compound is as follows:

[0050]

[0051]Under nitrogen protection, bis(4-bromophenyl)diphenylsilane (39.5g, 80mmol) was dissolved in 200mL toluene (Tol) solution, and then 3,6-di-tert-butyl-9H-carbazole ( 49.1g, 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 column chromatography with eluent n-hexane, and then dried at 50°C for 24 hours under vacuum to obtain off-white solid bis(4-(3,6-di tert-Butyl-9H-carbazol-9-yl)phenyl)diphenylsilane. The yield was 85%.

Embodiment 3

[0053] The tetraphenylsilicon-based blue-light phosphorescent compound of this embodiment, that is, bis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)diphenylsilane, has the following structural formula:

[0054]

[0055] The preparation process of this compound is as follows:

[0056]

[0057] Under nitrogen protection, bis(4-bromophenyl)diphenylsilane (39.5g, 80mmol) was dissolved in 200mL acetonitrile (MeCN) solution, and then 3,6-di-tert-butyl-9H-carbazole ( 53.6g, 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 column chromatography with eluent n-hexane, and then dried at 50°C for 24 hours under vacuum to obtain off-white solid bis(4-(3,6-di tert-Butyl-9H-carbazol-9-yl)phenyl)diphenylsilane. The yield was 76%.

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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses a tetraphenyl silicon-based blue light phosphorescent material and a preparation method thereof and an organic electroluminescent device; and the structural formula of the material is shown in the specification. The tetraphenyl silicon-based blue light phosphorescent material has higher triplet state energy level, can effectively prevent the energy from being back conveyed to the main material in the luminescence process, and can greatly improve the luminous efficiency.

Description

technical field [0001] The invention relates to organic semiconductor materials, in particular to a tetraphenyl silicon-based blue 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 tetraphenylsilicon-based blue phosphorescent material as a main 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 achieving...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F7/10H01L51/54
Inventor 周明杰张振华王平黄辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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