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Thermally activated delayed fluorescent material based on cyanopyridine and preparation method and application thereof in organic electroluminescence

A technology of thermally activated delayed and fluorescent materials, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., to achieve good device performance, achieve device performance, and high yield.

Inactive Publication Date: 2021-07-13
南京益米昇光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the main method for light color regulation is the modification and modification of the acceptor unit, and the method of fixing the acceptor unit to change the donor unit is rarely reported.

Method used

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  • Thermally activated delayed fluorescent material based on cyanopyridine and preparation method and application thereof in organic electroluminescence
  • Thermally activated delayed fluorescent material based on cyanopyridine and preparation method and application thereof in organic electroluminescence
  • Thermally activated delayed fluorescent material based on cyanopyridine and preparation method and application thereof in organic electroluminescence

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Compound 1

[0040] 2,3,5,6-tetrafluoro-4-cyanopyridine (0.5g, 2.84mmol), 3,6-dimethylcarbazole (2.77g, 14.20mmol), potassium carbonate (3.92g, 28.40mmol) , DMSO 12mL, heated at 150°C, and reacted at normal pressure under nitrogen atmosphere for 18h. After the reaction solution was cooled to room temperature, it was poured into 400 mL of water and stirred. A large amount of solids precipitated. After suction filtration, a solvent was prepared with dichloromethane and petroleum ether at a volume ratio of 1:2, and the final product was purified by silica gel column chromatography. 1 H NMR (400MHz, CDCl 3 ,δppm): 7.59(s, 4H), 7.51(s, 4H), 7.33-7.30(d, J=12Hz, 4H), 7.18-7.16(d, J=8Hz, 4H), 7.02-7.00(m, 4H), 6.88-6.85 (m, 4H), 2.42-2.34 (m, 24H).

[0041]

Embodiment 2

[0042] Example 2: Compound 2

[0043] 2,3,5,6-tetrafluoro-4-cyanopyridine (0.5g, 2.84mmol), 3,6-di-tert-butylcarbazole (3.97g, 14.20mmol), potassium carbonate (3.92g, 28.40mmol ), DMSO 12mL, heated at 150°C, and reacted at normal pressure under nitrogen atmosphere for 18h. After the reaction solution was cooled to room temperature, it was poured into 400 mL of water and stirred. A large amount of solids precipitated. After suction filtration, a solvent was prepared with dichloromethane and petroleum ether at a volume ratio of 1:3, and the final product was purified by silica gel column chromatography. 1 H NMR (400MHz, CDCl 3 , δppm): 7.61-7.60(d, J=4Hz, 4H), 7.55-7.54(d, J=4Hz, 4H), 7.15-7.13(d, J=8Hz, 4H), 7.04-7.01(m, 4H ), 6.97-6.95 (d, J=8Hz, 4H), 6.90-6.87 (m, 4H), 1.37-1.34 (d, J=12Hz, 72H).

[0044]

Embodiment 3

[0045]Example 3: Compound 3

[0046] 2,3,5,6-tetrafluoro-4-cyanopyridine (0.5g, 2.84mmol), 2,7-dimethylcarbazole (2.77g, 14.20mmol), potassium carbonate (3.92g, 28.40mmol) , DMSO 12mL, heated at 150°C, and reacted at normal pressure under nitrogen atmosphere for 18h. After the reaction solution was cooled to room temperature, it was poured into 400 mL of water and stirred. A large amount of solids precipitated. After suction filtration, a solvent was prepared with dichloromethane and petroleum ether at a volume ratio of 1:2, and the final product was purified by silica gel column chromatography. 1 H NMR (400MHz, CDCl 3 , δppm): 7.61-7.59(d, J=8Hz, 4H), 7.55-7.53(d, J=8Hz, 4H), 7.26(s, 4H), 7.09(s, 4H), 6.94-6.92(d, J=8Hz, 4H), 6.89-6.87 (d, J=8Hz, 4H), 2.23-2.17 (d, J=24Hz, 24H).

[0047]

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Abstract

The invention discloses a thermally activated delayed fluorescent material based on cyanopyridine. The structural general formula of the thermally activated delayed fluorescent material is shown as a formula I. The compound comprises an electron acceptor of cyanopyridine and an electron donor of a carbazole derivative; the compound is connected through a simple and cheap coupling reaction, and the yield is high. By changing the structure of the electron donor, the photoelectric property can be regulated and controlled, and the light-emitting color is distributed in a wider range from blue-green light to orange-red light. In addition, when the thermally activated delayed fluorescent material is applied to an organic electroluminescent device, good device performance can be realized.

Description

technical field [0001] The present invention relates to the field of organic electroluminescent materials, in particular to a class of thermally activated delayed fluorescent materials based on cyanopyridine and its preparation method and application in organic electroluminescence Background technique [0002] In the past few decades, organic light-emitting diodes (OLEDs) have attracted widespread attention due to their advantages such as low cost, high brightness, wide viewing angle, fast response, and flexible display, and are considered to be a very promising lighting and display technology. . According to different luminescent mechanisms, organic electroluminescence can be roughly divided into three categories: traditional fluorescence (Fluorescence), phosphorescence (Phosphorescence) and thermally activated delayed fluorescence (Thermally Activated Delayed Fluorescence, TADF). Among them, phosphorescent materials induce spin-orbit coupling by introducing transition met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C09K11/06H01L51/54
CPCC07D401/14C09K11/06C09K2211/1029H10K85/6572
Inventor 陶友田袁文博
Owner 南京益米昇光电科技有限公司
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