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Carbazolo-aromatic ring thermal activation delayed fluorescence material and organic electroluminescent device thereof

A technology of thermally activated delayed and fluorescent materials, which is applied in luminescent materials, electrical solid devices, organic chemistry, etc., can solve the problems of short delay life luminous efficiency, efficiency attenuation, long delay life, etc., to reduce intermolecular aggregation and low efficiency Attenuation, reducing the effect of delay life

Inactive Publication Date: 2020-09-22
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Existing thermally activated delayed fluorescence (TADF) materials usually have a long delay life (tens to hundreds of microseconds), so that the devices based on them will have significant efficiency degradation under high brightness. Therefore, short delay life, Thermally activated delayed fluorescent materials with high luminous efficiency are of great significance

Method used

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  • Carbazolo-aromatic ring thermal activation delayed fluorescence material and organic electroluminescent device thereof
  • Carbazolo-aromatic ring thermal activation delayed fluorescence material and organic electroluminescent device thereof
  • Carbazolo-aromatic ring thermal activation delayed fluorescence material and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The heat-activated delayed fluorescent material of carbazolo aromatic ring of the present invention 1312'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-12'H -Spiro[fluorene-9,7'-indeno[1,2-a]carbazole] can be synthesized by the following method.

[0057]

[0058] (1) In a dry 100ml two-necked flask, 4-bromo-9,9'-spirobis[fluorene] (3.00g, 7.6mmol), 2-chloroaniline (1.07g, 8.4mmol), palladium acetate ( Add 0.34g, 1.5mmol), DPPF (0.83g, 1.5mmol) and sodium tert-butoxide (2.20g, 22.8mmol) in sequence, then add 40mL of dry toluene, stir rapidly and blow a large amount of nitrogen for 5-10 minutes, under the protection of nitrogen Stir at reflux for 5 hours. Cooling, extraction first, spin-drying, column chromatography with petroleum ether and dichloromethane can give intermediate 1-1(N-(2-chlorophenyl)-9,9'-spirobis[fluorene]-4-amine ), yield 63%.

[0059] (2) Add intermediate 1-1 (3.00g, 6.7mmol), palladium acetate (0.30g, 1.3mmol), potassium carbonate (4.62g, 33.5mmol...

Embodiment 2

[0063] The carbazolo aromatic ring thermally activated delayed fluorescent material prepared in Example 1 has the formula 13(12'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl )-12'H-spiro[fluorene-9,7'-indeno[1,2-a]carbazole]) as light-emitting guest to prepare devices.

[0064] This example demonstrates the performance verification of an organic 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 60nm thick hole transport material: 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl (NPB), and then evaporati...

Embodiment 3

[0067] The 23(7,7-dimethyl-12-(3-(pyrimidin-2-yl)pyridin-2-yl)-7,12-dihydroindeno[1,2-a]carba Azole) can be synthesized by the following method.

[0068]

[0069] (4) In a dry 100ml two-necked flask, mix 4-bromo-9,9-dimethylfluorene (2.07g, 7.6mmol), 2-chloroaniline (1.07g, 8.4mmol), palladium acetate (0.34g , 1.5mmol), DPPF (0.83g, 1.5mmol) and sodium tert-butoxide (2.20g, 22.8mmol) were added sequentially, and then 40mL of dry toluene was added, and a large amount of nitrogen gas was stirred rapidly for 5-10 minutes, and reflux was stirred under nitrogen protection. 5 hours. After cooling, extract first, spin dry, and use petroleum ether and dichloromethane column chromatography to obtain intermediate 3-1 with a yield of 70%.

[0070] (5) Add intermediate 3-1 (2.14g, 6.7mmol), palladium acetate (0.30g, 1.3mmol), potassium carbonate (4.62g, 33.5mmol), tricyclohexylphosphine fluoroboron to a dry 100ml three-necked flask salt (1.43g, 3.9mmol), take 20ml of N,N-dimethylace...

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Abstract

The invention discloses a carbazolo-aromatic ring thermal activation delayed fluorescence material and an organic electroluminescent device. The structural formula of the carbazolo-aromatic ring thermal activation delayed fluorescent material is shown in the specification. The carbazolo-aromatic ring thermal activation delayed fluorescent material provided by the invention takes a carbazolo-aromatic ring as a core; due to the large volume and rigidity, molecules have a steric hindrance effect, intramolecular distortion is realized, and electron clouds of the highest occupied orbit and the lowest empty orbit of the molecules can be relatively separated to obtain a quite small single triplet state energy level difference, so that light-emitting molecules with a thermal activation delayed fluorescence property are designed and prepared; the thermal performance, the light-emitting efficiency and the light color of the material can be adjusted, and the material can be used as a guest material, can also be used as a host material by utilizing the thermal activation delayed fluorescence property, and can be constructed through molecular design.

Description

technical field [0001] The invention belongs to the technical field of preparation and application of organic photoelectric materials, and more specifically relates to a preparation method and application of carbazolo aromatic ring derivatives. Background technique [0002] Since Kodak first reported Organic Light Emitting Diode (OLED) in 1987 (Pope M., Kallmann.H.P., Magnante.P., Electroluminescence in Organic Crystals. The Journal of Chemical Physics 1963,38(8):2042- 2043), through the continuous synthesis of new materials and optimized device structures, the research of OLEDs has made a major breakthrough, showing attractive industrialization prospects in the next generation of flat-panel displays and lighting sources. Subsequently, in 1990, the University of Cambridge in the United Kingdom introduced polymer electroluminescent materials and devices. In 1998, Forrest, Thompson and Ma introduced phosphorescent complexes as light-emitting materials into the light-emitting ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D491/048C07D495/04C07D403/10C09K11/06H01L51/54
CPCC07D401/14C07D491/048C07D495/04C07D403/10C09K11/06C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1033C09K2211/1037H10K85/654H10K85/6572H10K85/657
Inventor 杨楚罗吕夏蕾
Owner SHENZHEN UNIV
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