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Organic electroluminescent compound and application thereof

An electroluminescence and compound technology, applied in the field of organic electroluminescence compounds, can solve the problems of poor performance of phosphorescent host materials, unable to meet the requirements of OLED devices, etc., and achieve improved luminous brightness and luminous efficiency, good electron mobility, and macromolecules. The effect of density

Active Publication Date: 2019-12-20
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] CN107311978A, CN104725419A, CN103012481A, etc. disclose phosphorescent host materials and their applications, but the performance of the phosphorescent host materials found so far is not good enough to meet people's requirements for OLED devices

Method used

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  • Organic electroluminescent compound and application thereof
  • Organic electroluminescent compound and application thereof
  • Organic electroluminescent compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0119] This embodiment provides an organic electroluminescent compound with the following structure:

[0120]

[0121] The synthetic route is as follows:

[0122]

[0123] The specific preparation method is as follows:

[0124] (1) Compound M1-1 (10mmol), 1H-carbazole (10.5mmol), (dibenzylideneacetone) dipalladium (0.05mmol), sodium tert-butoxide (14mmol) and 4,5-diphenyl Phosphine-9,9-dimethylxanthene (0.2mmol) was put into a 50mL three-necked flask, and the degassing and nitrogen replacement were repeated three times rapidly under stirring, and 20mL of toluene was added through a syringe; ℃ and heated to reflux for 3 hours; after the reaction, add water to the reaction solution cooled to room temperature, use dichloromethane to extract, and use saturated brine to wash; use anhydrous sodium sulfate to dry the organic layer, and The solvent was distilled off and purified by column chromatography to obtain intermediate M1-2.

[0125] (2) Weigh the intermediate M1-2 (10...

Embodiment 2

[0129] This embodiment provides an organic electroluminescent compound with the following structure:

[0130]

[0131] The synthetic route is as follows:

[0132]

[0133] The specific preparation method is as follows:

[0134] (1) Add compound M14-1 (3mmol), cuprous oxide (8mmol), dimethylacetamide (DMAC, 4mL) and 9,9-dimethyl-9,10-dihydro in a 50mL round bottom flask Acridine (3.5 mmol) was refluxed at 170° C. for 48 hours under an argon atmosphere. The obtained intermediate was cooled to room temperature, added to water, and then filtered through a pad of diatomaceous earth. The filtrate was extracted with dichloromethane, then washed with water, and used After drying over anhydrous magnesium sulfate, filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate M14-2.

[0135] (2) In a 250mL round bottom flask, intermediate M14-2 (15mmol), potassium acetate (40mmol) and dry 1,4-dioxane (60mL), bis(triphenylpho...

Embodiment 3

[0140] This embodiment provides an organic electroluminescent compound with the following structure:

[0141]

[0142] The synthetic route is as follows:

[0143]

[0144] The specific preparation method is as follows:

[0145] (1) Compound M30-1 (15mmol) and potassium acetate (40mmol) were mixed with dry 1,4-dioxane (60mL), Pd(PPh 3 ) 2 Cl 2 (0.4mmol) and pinacol diboronate (25mmol) were mixed, and stirred at 90° C. under a nitrogen atmosphere for 48 hours. The resulting intermediate was cooled to room temperature, added to water, and filtered through a pad of celite. The filtrate was extracted with dichloromethane, washed with water, and dried over anhydrous magnesium sulfate. After filtration and evaporation, the crude product was purified by silica gel column chromatography. The product gave intermediate M30-2.

[0146] (2) Intermediate M30-2 (10mmol), 3-bromo-9-phenyl-9H-carbazole (12mmol) and Pd(PPh 3 ) 4 (0.3mmol) was added to a mixture of toluene (30mL) / et...

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Abstract

The invention provides an organic electroluminescent compound and application thereof. The organic electroluminescent compound has a structure as shown in formula I and is a novel bipolar light-emitting organic compound. The organic electroluminescent material can be used as a light-emitting layer material of an organic electroluminescent device comprising an anode, a cathode, and at least one organic thin film layer between the anode and the cathode, and the light-emitting layer of the organic thin film layer comprises any one or a combination of at least two of the organic electroluminescentcompounds. The organic electroluminescent compound provided by the invention has high triplet energy level ET, large molecular density, high glass transition temperature and molecular thermal stability; balanced migration of carriers is improved effectively; an exciton recombination area is widened; the light extraction efficiency is improved; and the luminous efficiency of an organic electroluminescent device is greatly improved, the service life of the organic electroluminescent device is greatly prolonged, and the application prospect is wide.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic electroluminescent compound and its application. Background technique [0002] Organic Light Emitting Diode (OLED), as a new generation of display technology, has ultra-thin, self-luminous, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, Due to the advantages of low energy consumption, it has been widely used in industries such as flat panel display, flexible display, solid state lighting and vehicle display. [0003] According to the luminescence mechanism, organic electroluminescent materials can be divided into two types: electrofluorescence and electrophosphorescence. Electrofluorescence is the radiation decay transition of singlet excitons, and electrophosphorescence is the emission of triplet excitons radiatively decaying to the gro...

Claims

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Application Information

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IPC IPC(8): C07F7/08C07F9/6533C07F9/6558C09K11/06H01L51/50H01L51/54
CPCC07F7/0816C07F9/65335C07F9/65586C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/104C09K2211/1096C09K2211/1092C09K2211/1088C09K2211/1044C09K2211/1059C09K2211/1051C09K2211/1048C09K2211/1033H10K85/657H10K85/6576H10K85/322H10K85/40H10K85/6572H10K50/11
Inventor 代文朋牛晶华高威张磊肖文静
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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