Organic semiconductor material, preparation method thereof and electroluminescent device

A technology of electroluminescent devices and organic semiconductors, applied in the fields of electroluminescent devices, preparation, and organic semiconductor materials, can solve the problems of lack of carrier transport performance, low glass transition temperature, high triplet energy level, etc., and achieve It is beneficial to the balance of carrier transport, high triplet energy level, and the effect of simple and easy synthesis method

Inactive Publication Date: 2014-10-29
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

[0003] In recent years, the host material widely used in red phosphorescent devices is CBP, but it requires high driving voltage and glass transition temperature (T g ) Low (T g =62℃), easy to crystallize, the main reason is 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 thereof and electroluminescent device
  • Organic semiconductor material, preparation method thereof and electroluminescent device
  • Organic semiconductor material, preparation method thereof and electroluminescent device

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preparation example Construction

[0025] The invention provides a kind of preparation method of organic semiconductor material, comprises the steps:

[0026] Provides compound A: and compound B: Under an inert atmosphere, compound A and compound B are added into an organic solvent containing a catalyst and an alkali solution at a molar ratio of 1:2 to 2.4, and the Suzuki coupling reaction is carried out at 70 to 130°C for 12 to 48 hours, and the reaction is stopped to obtain an organic The chemical formula of a semiconductor material is as follows:

[0027]

[0028] The preparation method of the organic semiconductor material further includes a post-processing step, and the post-processing step is specifically: extracting the organic semiconductor material obtained by stopping the reaction with dichloromethane, combining the organic phases, drying them with anhydrous magnesium sulfate, and using petroleum A mixed solvent of ether and ethyl acetate was used as eluent, separated and purified through a sil...

Embodiment 1

[0041] 2-(3-(9,9'-spirobifluoren-2-yl)phenyl)-5-(3-(9,9'-spirobifluoren-7-yl)phenyl)-1,3, The preparation process of 4-oxadiazole preparation steps are as follows:

[0042]

[0043]Under argon protection, 2,5-bis(3-bromophenyl)-1,3,4-oxadiazole (76 mg, 0.2 mmol), 2-pinacol borate-9,9-spiro Difluorene (177mg, 0.4mmol) was added to a flask containing 10ml of toluene solvent, and after fully dissolving, potassium carbonate (2mL, 2mol / L) solution was added to the flask, vacuumed to remove oxygen and filled with argon, and then added bis Triphenylphosphinepalladium dichloride (5.6mg, 0.008mmol); the flask was heated to 100°C for Suzuki coupling reaction for 24h. The reaction was stopped and cooled to room temperature, extracted three times with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate and then spin-dried to obtain the 2-(3-(9,9'-spirobifluoren-2-yl)phenyl )-5-(3-(9,9'-spirobifluoren-7-yl)phenyl)-1,3,4-oxadiazole organic semicond...

Embodiment 2

[0048] 2-(3-(9,9'-spirobifluoren-2-yl)phenyl)-5-(3-(9,9'-spirobifluoren-7-yl)phenyl)-1,3, The preparation process of 4-oxadiazole preparation steps are as follows:

[0049]

[0050] Under the protection of mixed gas of nitrogen and argon, 2,5-bis(3-bromophenyl)-1,3,4-oxadiazole (76mg, 0.2mmol), 2-pinacol borate-9 , 9-spirobifluorene (292mg, 0.66mmol) 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. The reaction was stopped and cooled to room temperature, extracted three times with dichloromethane, the organic phases were combined, dried ov...

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Abstract

The invention provides an organic semiconductor material, which has a chemical formula shown as below. The organic semiconductor material is a red phosphorescence host material with electron-transporting capacity, so that the electron-transporting capacity is enhanced to facilitate carrier transporting balance; and the organic semiconductor material also has high triplet state energy level and excellent thermal stability, and effectively prevents back passing of energy to the host material in the luminescence process, thus greatly improving the luminous efficiency. 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): C07D271/107C09K11/06H01L51/54
CPCC09K11/06C07D271/107C09K2211/1048C09K2211/1007C09K2211/1011H10K85/624H10K85/626H10K85/6565
Inventor 周明杰张振华王平黄辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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