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Bipolar blue light phosphorescent compound, preparation method thereof and organic electroluminescent device

A compound and bipolar technology, applied in the field of bipolar blue phosphorescent compounds and their preparation, and organic electroluminescent devices, can solve problems such as lack, achieve good thermal stability and improve luminous efficiency.

Inactive Publication Date: 2015-01-21
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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  • Bipolar blue light phosphorescent compound, preparation method thereof and organic electroluminescent device
  • Bipolar blue light phosphorescent compound, preparation method thereof and organic electroluminescent device
  • Bipolar blue light phosphorescent compound, preparation method thereof and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: The bipolar blue phosphorescent compound of this example is: 9,9'-(9,9-bis(4-(diphenylphosphinooxy)phenyl)-9H-fluorene-2,7- Diyl) two (9H-carbazole), structural formula is as follows:

[0036]

[0037] The preparation process of this compound is as follows:

[0038]

[0039] Under nitrogen protection, (4,4'-(2,7-dibromo-9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(diphenylphosphineoxy)(70.1 g, 80mmol) was dissolved in 200mL N,N-dimethylformamide (DMF) solution, then added 9H-carbazole (26.7g, 160mmol), potassium carbonate (31.8g, 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 with distilled water three times. The crude product is separated by silica gel column chromatography with eluent n-hexane, and then dried under vacuum at 50°C for 24 hours to obtain off-white solid compound 9,9'-(9,9 - bis(4-(diphenylphosphinyloxy)phenyl...

Embodiment 2

[0040] Example 2: The bipolar blue phosphorescent compound of this example is: 9,9'-(9,9-bis(4-(diphenylphosphinooxy)phenyl)-9H-fluorene-2,7- Diyl) two (9H-carbazole), structural formula is as follows:

[0041]

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

[0043]

[0044] Under nitrogen protection, (4,4'-(2,7-dibromo-9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(diphenylphosphineoxy)(70.1 g, 80mmol) was dissolved in 200mL toluene (Tol) solution, then 9H-carbazole (29.4g, 176mmol), cesium carbonate (57.2g, 176mmol), copper powder (0.768g, 12mmol) were added. 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 with distilled water three times. The crude product is separated by silica gel column chromatography with eluent n-hexane, and then dried under vacuum at 50°C for 24 hours to obtain off-white solid compound 9,9'-(9,9 - bis(4-(diphenylphosphinyloxy)phenyl)-9H-fluoren...

Embodiment 3

[0045] Example 3: The bipolar blue phosphorescent compound of this example is: 9,9'-(9,9-bis(4-(diphenylphosphinyloxy)phenyl)-9H-fluorene-2,7- Diyl) two (9H-carbazole), structural formula is as follows:

[0046]

[0047] The preparation process of this compound is as follows:

[0048]

[0049] Under nitrogen protection, (4,4'-(2,7-dibromo-9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(diphenylphosphineoxy)(70.1 g, 80mmol) was dissolved in 200mL of acetonitrile (MeCN) solution, and then 9H-carbazole (32.1g, 192mmol), potassium phosphate (39g, 184mmol), cuprous oxide (2.3g, 16mmol) were added. 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 with distilled water three times. The crude product is separated by silica gel column chromatography with eluent n-hexane, and then dried under vacuum at 50°C for 24 hours to obtain off-white solid compound 9,9'-(9,9 - bis(4-(diphenylphosphinyloxy)pheny...

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Abstract

Belonging to the field of organic semiconductor materials, the invention discloses a bipolar blue light phosphorescent compound, a preparation method thereof and an organic electroluminescent device. Specifically, the structural formula of the host material is shown as the specification. In the bipolar blue light phosphorescent compound provided by the invention, the carbazole group is an excellent hole transport unit; and the diphenyl phosphine oxygen group contains electron withdrawing P=O, and is a good electron transport unit. Therefore, the material has hole transport properties and electron transport properties at the same time, enables hole and electron transport balance in a luminescent layer, and has a high triplet state energy level, and effectively prevents back transport of energy to the host material in a luminescence process, thereby improving the luminous efficiency.

Description

technical field [0001] The invention relates to the field of organic semiconductors, in particular to a bipolar blue light phosphorescent compound and a preparation method thereof. The invention also relates to an organic electroluminescent device using the bipolar blue phosphorescent compound as a host material of a light-emitting layer. 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 100% internal quantum efficiency. However, due t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F9/572H01L51/54
Inventor 周明杰张振华王平张娟娟
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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