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Bipolar green light phosphorescent host material, preparation method and organic electroluminescent device thereof

A technology of green phosphorescence and main materials, which is applied in the direction of luminescent materials, electric solid-state devices, semiconductor devices, etc., can solve low-level problems, achieve the effects of reduced manufacturing costs, reduced process flow, and cheap and easy-to-obtain raw materials

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

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Problems solved by technology

However, the vast majority of existing phosphorescent host materials are unipolar transport, such as the most widely used carbazole derivatives, most of which are mainly hole transport, and the carrier of organosilicon derivative phosphorescent host materials The transport property is not very high for holes and electrons, and the phosphorescent host materials of phenanthroline and triazine are dominated by electron transport

Method used

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  • Bipolar green light phosphorescent host material, preparation method and organic electroluminescent device thereof
  • Bipolar green light phosphorescent host material, preparation method and organic electroluminescent device thereof
  • Bipolar green light phosphorescent host material, preparation method and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The bipolar green phosphorescent host material of this embodiment, that is, 3-(3-(9,9'-spirobifluoren-2-yl)phenyl)-5-(3-(9,9'-spirobi Fluoren-7-yl)benzene)-4-phenyl-4H-1,2,4-triazole, the preparation steps are as follows:

[0041]

[0042] Under argon protection, 2-(9,9'-spirobifluoren-2-yl)-pinacol borate (88 mg, 0.2 mmol), 3,5-bis(3-bromophenyl)-4 -Phenyl-4H-1,2,4-triazole (182mg, 0.4mmol) was added into a flask filled with 10ml of toluene solvent, and after fully dissolving, potassium carbonate (2mL, 2mol / L) solution was added into the flask, pumped Deoxygenate in vacuo and fill with argon, then add bistriphenylphosphinepalladium dichloride (5.6mg, 0.008mmol); heat the flask to 100°C for Suzuki coupling reaction for 24h. Stop the reaction and cool to room temperature, extract the reaction solution several times with dichloromethane, combine the organic phases, and dry the organic phases with anhydrous magnesium sulfate and then spin dry to obtain the crude produc...

Embodiment 2

[0046] The bipolar green phosphorescent host material of this embodiment, that is, 3-(3-(9,9'-spirobifluoren-2-yl)phenyl)-5-(3-(9,9'-spirobi Fluoren-7-yl)benzene)-4-phenyl-4H-1,2,4-triazole, the preparation steps are as follows:

[0047]

[0048] Under the protection of a mixed gas of nitrogen and argon, 2-(9,9'-spirobifluoren-2-yl)-pinacol borate (133mg, 0.3mmol), 3,5-bis(3-bromobenzene Base)-4-phenyl-4H-1,2,4-triazole (300mg, 0.66mmol) and 15mL tetrahydrofuran were added to a 50mL two-necked bottle, and after fully dissolved, a mixture of nitrogen and argon was introduced to exhaust the air for about After 20min, tetrakistriphenylphosphine palladium (4mg, 0.003mmol) was added thereto, and after fully dissolved, sodium bicarbonate (3mL, 2mol / L) solution was added. 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, ...

Embodiment 3

[0050] The bipolar green phosphorescent host material of this embodiment, that is, 3-(3-(9,9'-spirobifluoren-2-yl)phenyl)-5-(3-(9,9'-spirobi Fluoren-7-yl)benzene)-4-phenyl-4H-1,2,4-triazole, the preparation steps are as follows:

[0051]

[0052] Under nitrogen protection, 2-(9,9'-spirobifluoren-2-yl)-pinacol borate (133mg, 0.3mmol), 3,5-bis(3-bromophenyl)-4- Phenyl-4H-1,2,4-triazole (328mg, 0.72mmol), palladium acetate (3.5mg, 0.015mmol) and tris(o-methoxyphenyl)phosphine (21mg, 0.06mmol) were added to the In a 12mL flask of N,N-dimethylformamide, add potassium carbonate (3mL, 2mol / L) solution after fully dissolving, then pass nitrogen into the flask and exhaust the air for about 30min; heat the flask to 130°C for Suzuki Coupling reaction 12h. Stop the reaction and cool to room temperature, extract the reaction solution several times with dichloromethane, combine the organic phases, and dry the organic phases with anhydrous magnesium sulfate and then spin dry to obtain t...

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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses a bipolar green light phosphorescent host material, a preparation method and an organic electroluminescent device thereof. The host material has a structural formula shown as the specification. The bipolar green light phosphorescent host material provided by the invention has hole transport properties and electron transport properties at the same time, and enables balance transport of holes and electrons in a luminescent layer. With a high triplet state energy level, the host material can effectively prevent back transmission of energy to the host material in a luminescence process, thus greatly improving the luminescence efficiency.

Description

technical field [0001] The invention relates to the field of organic semiconductor materials, in particular to a bipolar green phosphorescence host material and a preparation method thereof. The invention also relates to an organic electroluminescent device, the material of the light-emitting layer contains bipolar green phosphorescence host material. Background technique [0002] Since Tang et al. first reported interlayer organic light emitting diodes (organic light emitting diodes, OLEDs), this field has received widespread attention and attention in terms of flat panel displays and solid-state light sources. Compared with previous fluorescent OLEDs, phosphorescent OLEDs can utilize both excited singlet states and excited triplet states, and the theoretical internal quantum efficiency can reach 100%, which is considered to be a more effective way to improve device efficiency. Balancing the injection of holes and electrons and their transport in the light-emitting layer i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08H01L51/54
CPCC09K11/06C07D249/08C09K2211/1011C09K2211/1007C09K2211/1059H10K85/624H10K85/626H10K85/654
Inventor 周明杰张振华王平黄辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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