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Asymmetric heat-activated delayed fluorescent material, synthesis method and application thereof

A technology of thermally activated delayed and fluorescent materials, applied in luminescent materials, chemical instruments and methods, electrical components, etc., can solve the problems of no circularly polarized luminescence, energy loss, etc., to achieve efficient and stable light emission, high yield, synthesis Method and purification process simple effect

Active Publication Date: 2018-01-26
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the organic materials currently used in OLED displays basically do not have circularly polarized luminescence, that is, CPL characteristics. After the emitted light passes through a 1 / 4 wave plate, 50% of the light will be absorbed by the polarizer, resulting in serious energy loss.

Method used

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  • Asymmetric heat-activated delayed fluorescent material, synthesis method and application thereof
  • Asymmetric heat-activated delayed fluorescent material, synthesis method and application thereof
  • Asymmetric heat-activated delayed fluorescent material, synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] (R)-2-(9H-carbazol-9-yl)-3-(9,9-dimethylacridin-10(9H)-yl)benzo[b]binaphtho[2,1- e: Synthesis of 1',2'-g][1,4]dioxaoctatriene-1,4-dicarbonitrile, the synthetic route is as follows:

[0049]

[0050] Under argon protection, tetrafluoroterephthalonitrile (0.20g, 1.00mmol) and (R)-1,1'-bi-2-naphthol (0.286g, 1.00mmol) were added into a three-necked flask, and Dissolve in 10mL DMF, add K 2 CO 3 (0.28g, 2.00mmol), stirred the reaction at room temperature for 12 hours; then added 9,10-dihydro-9,9-dimethylacridine (0.21g, 1.00mmol) and potassium carbonate (0.14g, 1.00 mmol), stirred and reacted at 80°C for 12 hours; after the reaction solution was cooled to room temperature, 9H-carbazole (0.21g, 1.25mmol) and potassium carbonate (0.17g, 1.25mmol) were added, and the stirred reaction was continued at room temperature for 8 hours . After the reaction was finished, the reaction solution was poured into 150 mL of saturated brine to precipitate solids, and suction filtered. ...

Embodiment 2

[0052] (S)-2-(9H-carbazol-9-yl)-3-(9,9-dimethylacridin-10(9H)-yl)benzo[b]binaphtho[2,1- e: Synthesis of 1',2'-g][1,4]dioxaoctatriene-1,4-dicarbonitrile, the synthetic route is shown in the following formula:

[0053]

[0054] Under argon protection, tetrafluoroterephthalonitrile (0.20g, 1.00mmol) and (S)-1,1'-bi-2-naphthol (0.286g, 1.00mmol) were added into the three-necked flask, and Dissolve in 10mL DMF, add K 2 CO 3 (0.28g, 2.00mmol), stirred the reaction at room temperature for 12 hours; then added 9,10-dihydro-9,9-dimethylacridine (0.21g, 1.00mmol) and potassium carbonate (0.14g, 1.00 mmol), stirred and reacted at 80°C for 12 hours; after the reaction solution was cooled to room temperature, 9H-carbazole (0.21g, 1.25mmol) and potassium carbonate (0.17g, 1.25mmol) were added, and the stirred reaction was continued at room temperature for 8 hours . After the reaction was finished, the reaction solution was poured into 150 mL of saturated brine to precipitate solids, ...

Embodiment 3

[0056] (R)-2-(9H-carbazol-9-yl)-3-(10H-phenothiazin-10-yl)benzo[b]dinaphtho[2,1-e:1',2' -g] [1,4] The synthesis of dioxaoctatriene-1,4-dicarbonitrile, the synthetic route is as follows:

[0057]

[0058] Under argon protection, tetrafluoroterephthalonitrile (0.30g, 1.50mmol) and (R)-1,1'-bi-2-naphthol (0.43g, 1.50mmol) were added into a three-necked flask, and Dissolve in 15mL DMF, add K 2 CO 3 (0.42g, 3.00mmol), stirred and reacted at room temperature for 12 hours; then added 10H-phenothiazine (0.30g, 1.50mmol) and potassium carbonate (0.21g, 1.50mmol), stirred and reacted at room temperature for 12 hours; Finally, 9H-carbazole (0.31 g, 1.88 mmol) and potassium carbonate (0.26 g, 1.88 mmol) were added, and the stirring reaction was continued at room temperature for 8 hours. After the reaction, the reaction solution was poured into 200mL saturated brine to precipitate solids, and suction filtered, and the obtained crude product was separated and purified by silica gel co...

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Abstract

The invention discloses an asymmetric heat-activated delayed fluorescent material, a synthesis method and application thereof. The material has a structural formula shown as formula (1) in the specification, wherein Ar1 and Ar2 are aromatic amine substituent groups of different structures. The invention simultaneously discloses a synthesis method of the asymmetric heat-activated delayed fluorescent material, and also discloses a non-doped OLED device, wherein a luminescent layer is prepared from the asymmetric heat-activated delayed fluorescent material. The asymmetric heat-activated delayed fluorescent material disclosed by the invention has circularly polarized luminescence and aggregation-induced luminescence properties, good thermal stability and excellent luminescent properties, and the synthesis method and purification process are simple. The non-doped OLED device prepared from the heat-activated delayed fluorescent material as the luminescent layer has high luminance and good stability, so that both the luminous efficiency and service life of the OLED device can meet the practical requirements.

Description

technical field [0001] The invention relates to an asymmetric heat-activated delayed fluorescent material and its synthesis method and application. Background technique [0002] Organic Light-Emitting Diodes (OLEDs) have unique advantages such as fast response, wide viewing angle, thin and light volume, self-luminescence, and bendable, rollable and even foldable, so they are called the most potential next-generation display technology. , It is expected to replace liquid crystal displays and be widely used in electronic products such as mobile phones, TVs, tablet computers, VR (virtual reality) headsets and wearable smart devices. In view of its huge economic and social benefits, OLED display technology has been highly valued by academia, industry and even the governments of various countries, and is one of the hot spots and key areas of current research and development. Research on OLED materials and devices has made remarkable progress in recent years. However, so far, th...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D405/14C07D417/14C07D413/14H01L51/50H01L51/54
Inventor 许炳佳石光张敏敏黎建桉周京弘王玉海刘聪侯琼罗穗莲
Owner SOUTH CHINA NORMAL UNIVERSITY
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