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Luminescent material with thermotropic delayed fluorescence, application of luminescent material and electroluminescent device

A technology of thermally induced delayed fluorescence and luminescent materials, which is applied in the field of electroluminescent devices, can solve the problems of few electron-donating groups and electron-withdrawing groups, difficulty in molecular design of thermally induced delayed fluorescent materials, etc., and achieve long service life, Realize the effect of deep blue light emission and good stability

Inactive Publication Date: 2018-06-26
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, at present, the molecular design of thermally induced delayed fluorescence materials is difficult, and there are few electron-donating and electron-withdrawing groups to choose from.

Method used

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  • Luminescent material with thermotropic delayed fluorescence, application of luminescent material and electroluminescent device
  • Luminescent material with thermotropic delayed fluorescence, application of luminescent material and electroluminescent device
  • Luminescent material with thermotropic delayed fluorescence, application of luminescent material and electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] The spirobifluorene indole derivative 13 (5-(4,6-diphenyl-1,3,5-triazine)-5H spirofluorene-9,8-indenecarbazole) of the present invention can be Synthesized by the following method.

[0069]

[0070] (1) In a dry 500mL two-necked flask, 3-carbazoleboronic acid pinacol ester (15g, 51mmol), o-dibromobenzene (14.5g, 61.2mmol), toluene (120mL), ethanol (60mL) and 2mol / L potassium carbonate solution (60mL) were added, ultrasonication was performed first, and then nitrogen gas was rapidly stirred, and the catalyst tetrakis(triphenylphosphine)palladium (1.8g, 1.53mmol) was added rapidly, and a large amount of nitrogen gas was passed. Heat to 90°C and stir overnight. During treatment, extract first, spin dry, and use petroleum ether and dichloromethane column chromatography to obtain the white solid product 3-(2-bromophenyl)-9H-carbazole with a yield of 93%. C 18 h 12 BrN, mass spectrometry theoretical value 321.0153, measured by APCI (atmospheric pressure chemical ioniza...

Embodiment 2

[0079] The carbazole derivative prepared in Example 1 has the formula 13,5-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-12,12- Diphenyl-5,12-dihydroindeno[1,2-c]carbazole was used as light-emitting guest to prepare devices.

[0080]This example demonstrates the performance verification of an electroluminescent device prepared with 13 as a guest luminescent material. The ITO (Indium Tin Oxide) glass was ultrasonically cleaned in detergent and deionized water for 30 minutes sequentially. Then vacuum dry for 2 hours (105°C), then put the ITO glass into the plasma reactor for 5 minutes of oxygen plasma treatment, transfer it to the vacuum chamber to prepare organic film and metal electrode, and then prepare a layer of 10nm by vacuum evaporation. The hole injection material molybdenum trioxide, followed by evaporation of 70nm thick hole transport material: N4, N4'-two (naphthalene-1-yl) -N4, N4'-diphenyl-[1,1'-bi Benzene]-4,4'-diamine (NPB), then vapor-deposit 1,3-bis(9-carbazolyl...

Embodiment 3

[0083] 14(5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-12,12-diphenyl-5,12- Dihydroindeno[1,2-c]carbazole) can be synthesized by the following method.

[0084]

[0085] 14(5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-12,12-diphenyl-5,12-dihydroindeno[ 1,2-c]carbazole) synthesis. First synthesize the obtained 12,12-diphenyl-5,12-dihydroindeno[1,2-b]carbazole (1g, 2.466mmol) according to the steps (1)~(4) of Example 1, 2, 4-diphenyl-6 (3-bromophenyl) triazine (1.15g, 2.95mmol), cuprous iodide (0.28g, 1.47mmol), K 2 CO 3 (2.04g, 14.7mmol) and 18-crown-6 (0.378g, 1.47mmol) were dissolved in 3 mL of DMPU solution. Under the protection of N2, the temperature was raised to 175° C., and the reaction was carried out for 36 hours. After the reaction was terminated, it was cooled to room temperature, extracted, spin-dried, and subjected to column chromatography. Column chromatography with petroleum ether and dichloromethane gave 1.2 g of a yellow solid product with a yield of ...

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Abstract

The invention belongs to the fields of preparation and application sciences of organic photoelectric materials and specifically relates to a luminescent material with thermotropic delayed fluorescence, an application of the luminescent material and an electroluminescent device. The luminescent material with thermotropic delayed fluorescence, provided by the invention takes a carbazole derivative as a donor group, and a relatively small tripletenergy gap is achieved by molecular distortion, so that the reverse intersystem crossing from triplet excisions to singlet excisions is realized, and theutilization ratio of the excisions and the efficiency of the device are increased. By taking the luminescent material with thermotropic delayed fluorescence, provided by the invention, as a main luminescent material, the efficiency roll-off of the device can be reduced; and serving as an object luminescent material, the luminescent material with thermotropic delayed fluorescence is high in luminescent layer brightness, good in stability, high in luminescent efficiency and long in service life. If the luminescent material with thermotropic delayed fluorescence is used as an organic luminescentmedium, the device is reduced in efficiency roll-off, high in luminescent efficiency and long in service life.

Description

technical field [0001] The invention belongs to the technical field of preparation and application of organic photoelectric materials, and in particular relates to a luminescent material with thermally induced delayed fluorescence, its application and an electroluminescent device. Background technique [0002] In recent years, organic light emitting diodes (Organic Light Emitting Diode, referred to as OLED) have sprung up in the fields of display and lighting, and have gradually become an emerging industry that has attracted much attention. Compared with the current mainstream display-liquid crystal display (LCD), OLEDs have outstanding advantages such as self-illumination, wide viewing angle, fast response speed under high temperature and low temperature conditions, vivid color, high definition, bendable and low-cost potential. It is considered to be the next generation of flat panel display technology. In 2008, Sony Corporation of Japan launched an 11-inch full-color elec...

Claims

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Application Information

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IPC IPC(8): C07D209/94C07D403/10C07D471/14C07D409/10C07D403/04C07D401/14C07D403/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D209/94C07D401/14C07D403/04C07D403/10C07D403/14C07D409/10C07D471/14C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1092H10K85/655H10K85/654H10K85/6572H10K50/11
Inventor 穆广园吕夏蕾庄少卿
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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