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Organic semiconductor material, preparation method of organic semiconductor material and electroluminescent device

A technology of organic semiconductors and main materials, applied in the direction of semiconductor devices, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve problems such as shortage, achieve high triplet energy level, simple and easy synthesis method, and balanced transmission

Inactive Publication Date: 2014-03-12
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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  • Organic semiconductor material, preparation method of organic semiconductor material and electroluminescent device
  • Organic semiconductor material, preparation method of organic semiconductor material and electroluminescent device
  • Organic semiconductor material, preparation method of organic semiconductor material and electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation process of 2,7-bis(4-(carbazol-9-yl)phenyl)-4,9-diphenylanthrazole

[0024] The preparation steps are as follows:

[0025]

[0026] Under argon protection, compound A: 9-(4-boronic acid pinacol ester phenyl) carbazole (74mg, 0.2mmol), compound B: 2,7-dibromo-4,9-diphenylanthracene Add azole (98mg, 0.2mmol) into a flask filled with 10ml of toluene solvent, and after fully dissolving, add potassium carbonate (2mL, 2mol / L) solution into the flask, evacuate the oxygen and fill it with argon, then add bis(three) Phenylphosphinepalladium dichloride (5.6mg, 0.008mmol); the flask was heated to 100°C for Suzuki coupling reaction for 24h. Stop the reaction and cool to room temperature, extract three times with dichloromethane, combine the organic phases, spin dry after drying over anhydrous magnesium sulfate, the crude product adopts sherwood oil: ethyl acetate volume ratio is 10:1 as eluent through silica gel chromatography Column separation gave white crystals....

Embodiment 2

[0029] Example 2: The preparation process of 2,7-bis(4-(carbazol-9-yl)phenyl)-4,9-diphenylanthrazole

[0030] The preparation steps are as follows:

[0031]

[0032] Under the protection of mixed gas of nitrogen and argon, compound A: 9-(4-boronic acid pinacol ester phenyl) carbazole (119 mg, 0.3 mmol), compound B: 2,7-dibromo-4,9 - Diphenylanthrazole (162mg, 0.33mmol) and 15mL tetrahydrofuran were added into a 50mL two-necked bottle, fully dissolved, and then a mixture of nitrogen and argon was introduced to exhaust the air for about 20 minutes, and then tetrakistriphenylphosphine palladium ( 4mg, 0.003mmol) into it, fully dissolved and then added sodium bicarbonate (3mL, 2mol / L) solution. Then, the mixed gas of nitrogen and argon was exhausted for about 10 minutes, and the two-neck flask was added to 70°C for Suzuki coupling reaction for 48 hours. Stop the reaction and cool to room temperature, extract three times with dichloromethane, combine the organic phases, spin d...

Embodiment 3

[0033] Example 3: The preparation process of 2,7-bis(4-(carbazol-9-yl)phenyl)-4,9-diphenylanthrazole

[0034] The preparation steps are as follows:

[0035]

[0036] Under nitrogen protection, compound A: 9-(4-boronic acid pinacol ester phenyl) carbazole (119 mg, 0.3 mmol) and compound B: 2,7-dibromo-4,9-diphenylanthrazole (176mg, 0.36mmol), palladium acetate (3.5mg, 0.015mmol) and three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) were added to a flask containing 12mL of N,N-dimethylformamide After being fully dissolved, potassium carbonate (3mL, 2mol / L) solution was added, and then the flask was purged with nitrogen for about 30min; the flask was heated to 130°C for Suzuki coupling reaction for 12h. Stop the reaction and cool to room temperature, extract three times with dichloromethane, combine the organic phases, spin dry after drying over anhydrous magnesium sulfate, the crude product adopts sherwood oil: ethyl acetate volume ratio is 10:1 as eluent through silica gel...

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Abstract

The invention provides an organic semiconductor material. The organic semiconductor material has a chemical formula shown in the patent specification. The organic semiconductor material contains anthrazole and carbazole. Carbazole has a high triplet-state energy level and hole transport performances. Anthrazole has good rigidity, flatness, electron transmission performances and thermostability. Therefore, the organic semiconductor material is a bipolar blue-light-emitting host material. The invention also provides a preparation method of the organic semiconductor material and an electroluminescent device containing the organic semiconductor material.

Description

technical field [0001] The invention belongs to the field of photoelectric materials, and in particular relates to an organic semiconductor material, a preparation method and an electroluminescent device. 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 to the relatively long lifetime of excited-state excitons in transition metal complexes, the unwanted triplet-triplet (T 1 -T 1 ) are qu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06H01L51/54
CPCC07D471/04H10K85/6572
Inventor 周明杰王平张振华冯小明
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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