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 p

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

Example Embodiment

[0118] Example 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) two palladium (0.05mmol), sodium tert-butoxide (14mmol) and 4,5-bisdiphenyl Phosphine-9,9-dimethylxanthene (0.2mmol) was put into a 50mL three-necked flask, degassing and nitrogen replacement were repeated 3 times quickly under stirring, 20mL of toluene was added via a syringe; Heat to reflux at ℃ for 3 hours; after the reaction, add water to the reaction solution that has been cooled to room temperature, extract with dichloromethane, and wash with saturated brine; after drying the organic layer with anhydrous sodium sulfate, The solvent was distilled off and purified by column chromatography to obtain intermediate M1-2.

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

Example Embodiment

[0128] Example 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 (3.5mmol) 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 celite. The filtrate was extracted with dichloromethane, then washed with water and used After drying with anhydrous magnesium sulfate, filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate M14-2.

[0135] (2) Intermediate M14-2 (15mmol), potassium acetate (40mmol) and dry 1,4-dioxane (60mL), bis(triphenylphosphine) palladium dichloride in a 250mL roun...

Example Embodiment

[0139] Example 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) Combine compound M30-1 (15mmol) and potassium acetate (40mmol) with dry 1,4-dioxane (60mL), Pd(PPh) in a 250mL round bottom flask 3 ) 2 Cl 2 (0.4 mmol) and pinacol diborate (25 mmol) were mixed and stirred at 90°C under a nitrogen atmosphere for 48 hours. 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 dried with anhydrous magnesium sulfate. After filtration and evaporation, the crude was purified by silica gel column chromatography. The product obtained intermediate M30-2.

[0146] (2) Intermediate M30-2 (10mmol), 3-bromo-9-phenyl-9H-carbazole (12mmol) and Pd(PPh 3 ) 4 (0.3 mmol) wa...

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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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