Dicarbazole compound containing tetraphenylethylene structure as well as preparation and application thereof

A technology of tetraphenylethylene and biscarbazole, which is applied in the fields of chemical instruments and methods, organic chemistry, organic semiconductor device materials, etc., can solve the problems of weak luminescence and no luminescence, and achieve easy operation, high luminous efficiency, The effect of broad application prospects

Active Publication Date: 2017-12-22
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Until 2001, Tang Benzhong and others discovered a phenomenon completely opposite to ACQ: some materials emit weakly or even no light in solution, but emit stronger light in solid film

Method used

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  • Dicarbazole compound containing tetraphenylethylene structure as well as preparation and application thereof
  • Dicarbazole compound containing tetraphenylethylene structure as well as preparation and application thereof
  • Dicarbazole compound containing tetraphenylethylene structure as well as preparation and application thereof

Examples

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Effect test

Embodiment 1

[0028] Example 1. The preparation of 9,9'-(5-(2,2-diphenyl-1-(4-phenylmethyl))vinyl-1,3-phenylene)biscarbazole, the steps are as follows :

[0029] (1) Synthesis of 3,5-bis(9-carbazolyl)phenyl-(4-methylphenyl)methanone;

[0030] At -78°C, 18.8 mL of tert-butyllithium (1.3 M , 24.4mmol), stirred at this temperature for 1h, then stirred at room temperature for 5h; then the temperature of the mixture was lowered to -78°C, and 3.9mL (32.7mmol) of p-tolualdehyde was added to the mixture; the reactant Gradually return to room temperature, stir the reaction overnight at room temperature; quench the reaction with ice water, stop stirring, CH 2 Cl 2 Extract 3 times, wash 3 times with water, combine the organic layers, wash with anhydrous MgSO 4 Drying and spin-drying the solvent; and then separated by column chromatography to obtain 1.9 g of compound 3,5-bis(9-carbazolyl)phenyl-(4-methylphenyl)methanone as a white solid, with a yield of 36.5%;

[0031] (2) Synthesis and characteri...

Embodiment 2

[0034] Embodiment 2. Structure, preparation and performance of organic electroluminescent devices:

[0035] The device we prepared is a blue-green organic electroluminescent device, and the device structure is: ITO / HATCN (thickness 20nm) / NPB (thickness 40nm) / compound DPPBC (thickness 20nm) / TPBI (thickness 40nm) / LiF (thickness 1nm) / Al (thickness 100nm). Among them, HATCN is used as a hole injection layer, and NPB is used as a hole transport layer; 9,9'-(5-(2,2-diphenyl-1-(4-benzyl))vinyl-1,3- Phenylene) biscarbazole (compound DPPBC) as the light emitting layer; TPBI as the electron transport layer.

[0036] Preparation steps of the device: first scrub the ITO glass with acetone, then rinse it with clean water, then ultrasonically clean it with cleaning solution, and finally clean it ultrasonically with clean water. The cleaned substrates were blown dry with nitrogen, and finally treated with UV-ozone to fully clean the surface. According to the structure of the designed dev...

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Abstract

The invention provides a dicarbazole compound containing a tetraphenylethylene structure as well as a preparation and application thereof. The name of the compound is as follows: 9,9'-(5-(2,2-diphenyl-1-(4-benzyl))vinyl-1,3-phenylene)dicarbazole. A preparation method comprises the following steps: firstly, preparing 3,5-di(9-carbazolyl)phenyl-(4-methylphenyl)ketone; then enabling the 3,5-di(9-carbazolyl)phenyl-(4-methylphenyl)ketone to react with diphenylmethane to obtain the 9,9'-(5-(2,2-diphenyl-1-(4-benzyl))vinyl-1,3-phenylene)dicarbazole. The compound provided by the invention has good thermal stability, electrochemical stability, charge transferring property and luminescent property and can be used as a blue-green organic electroluminescent material.

Description

technical field [0001] The invention relates to a heterocyclic compound containing carbon, hydrogen and nitrogen, in particular to a preparation method of a biscarbazole compound containing a tetraphenylethylene structure and the application of the compound as an organic electroluminescent material. Background technique [0002] Organic light-emitting diodes (OLEDs) have become a hotspot in both academia and business because of their wide applications in solid-state light-emitting and flat-panel displays. Generally, OLED devices need to absorb excitons to emit light through the transport layer and the light-emitting layer. However, when traditional light-emitting materials are used as light-emitting layers to prepare OLEDs, concentration quenching effect (ACQ) usually occurs, that is, the light is strong in the solution state, but in the solid-state aggregation due to the π-π stacking effect between molecules Diminish the glow. This ACQ effect severely restricts the develo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07D209/86C09K2211/1007C09K2211/1029H10K85/6572H10K50/11H10K2102/00H10K2102/301
Inventor 董秀清施和平王淑娟张鑫磊程芳琴
Owner SHANXI UNIV
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