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A Novel Thermally Activated Delayed Fluorescent Material Based on Excimer Luminescence and Its Application

A thermal activation delay and luminescent material technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of long luminous life of DF, roll-off efficiency of organic light-emitting diodes, and difficulties in the composition of exciplex-type TADF materials. Control and other issues to achieve the effect of reducing ΔEST

Active Publication Date: 2021-02-02
NANJING VOCATIONAL UNIV OF IND TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention: In view of the shortcomings of traditional TADF materials such as long DF luminescence lifetime, serious efficiency roll-off of the prepared organic light-emitting diodes, and difficulty in controlling the components of exciplex-type TADF materials, this application provides a New TADF Material Design Strategy

Method used

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  • A Novel Thermally Activated Delayed Fluorescent Material Based on Excimer Luminescence and Its Application
  • A Novel Thermally Activated Delayed Fluorescent Material Based on Excimer Luminescence and Its Application
  • A Novel Thermally Activated Delayed Fluorescent Material Based on Excimer Luminescence and Its Application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the preparation of 3,5-dicyanobenzoyl chloride:

[0031]

[0032] First, add 3,5-dibromobenzoic acid (5.6 g, 20.0 mmol) into a 100 ml round-bottomed two-necked flask equipped with a magnet, then add 15 ml of methanol, and slowly add thionyl chloride (3.0 ml, 40.0 mmol) and stirred at 70°C for 6 hours under the protection of argon. After the reaction, the reaction mixture was concentrated to obtain DBPOMe (6 g) with a yield of 100%.

[0033] Put the above product (3 g, 10.0 mmol) and cuprous cyanide (2.26 g, 25.0 mmol) into a 100 ml round-bottomed two-necked flask with a magnet, and add 40 ml of ultra-dry N,N-dimethylformaldehyde amide (DMF), and stirred at 180°C for 24 hours under the protection of argon. After the reaction was cooled to room temperature, the reaction solution was poured into a 500 ml separatory funnel, washed with saturated brine (200 ml) and extracted with dichloromethane. The collected organic phase was treated with anhydrous magn...

Embodiment 2

[0036]Example 2: Preparation of Compound 1 (5-(9H-carbazole-9-carbonyl)isophthalonitrile)

[0037]

[0038] Under the condition of 0ºC, carbazole (0.84 g, 5 mmol) and 60% NaH (0.24 g, 6 mmol) were dissolved in anhydrous THF (20 mL) and stirred at room temperature for 30 minutes, then 3, 5-Dicyanobenzoyl chloride (1.1 ml, 5 mmol). After stirring for 10 minutes, return to room temperature and stir for another 2 hours. The product was treated with CH 2 Cl 2 Extract three times and collect the organic phase, the organic phase with anhydrous magnesium sulfate (MgSO 4 )dry. The solvent was removed by distillation under reduced pressure, and the obtained crude product was purified by column chromatography, and the eluent was petroleum ether and dichloromethane in a volume ratio of 3:1. The product was a yellow-green powder, which was recrystallized several times from dichloromethane / hexane to give yellow-green crystals (1.1 g, yield 70%).

Embodiment 3

[0039] Embodiment 3: Preparation of compound 2

[0040]

[0041] At 0ºC, acridine (1.05 g, 5 mmol) and 60% NaH (0.24 g, 6 mmol) were dissolved in anhydrous THF (20 mL) and stirred at room temperature for 30 minutes, then 3, 5-Dicyanobenzoyl chloride (1.1 ml, 5 mmol). After stirring for 10 minutes, return to room temperature and stir for another 2 hours. The product was treated with CH 2 Cl 2 Extract three times and collect the organic phase, the organic phase with anhydrous magnesium sulfate (MgSO 4 )dry. The solvent was removed by distillation under reduced pressure, and the obtained crude product was purified by column chromatography, and the eluent was petroleum ether and dichloromethane in a volume ratio of 3:1. The product was a yellow-green powder, which was recrystallized several times from dichloromethane / hexane to give yellow-green crystals (1.1 g, yield 65%).

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Abstract

The invention discloses a new type of thermally activated delayed fluorescent material, which is an organic small molecule material containing 5-acetylisophthalonitrile structural unit. Under high concentration or aggregation state (such as film, crystal, etc.), it exhibits excimate-type heat-activated delayed fluorescence properties, and the delayed fluorescence lifetime is shorter than that of traditional heat-activated delayed fluorescence materials. It can be used to replace traditional heat-activated delayed fluorescence or organometallic complex materials in organic light-emitting diodes, biological imaging, optical anti-counterfeiting and other organic optoelectronic fields.

Description

technical field [0001] The invention relates to the field of organic luminescence, in particular to a novel heat-activated delayed fluorescent material based on excimer association light emission and its application. Background technique [0002] Compared with traditional inorganic light-emitting materials, organic light-emitting materials have many advantages such as self-luminescence, wide viewing angle, fast response speed, and flexible display. They are considered to replace traditional inorganic light-emitting materials and become the mainstream of next-generation lighting and display technologies. [0003] Organic light-emitting diodes (OLEDs) can be classified into fluorescent devices and phosphorescent devices according to different light-emitting mechanisms. According to electron spin theory, the theoretical value of internal quantum efficiency of fluorescent devices is only 25%, while that of phosphorescent devices can reach 100%. Therefore, the luminous efficiency...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07D219/02C07D265/38C07D279/30C09K11/06H01L51/00H01L51/54H10K99/00
CPCC07D209/86C07D219/02C07D265/38C07D279/30C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1007H10K85/657H10K85/6572
Inventor 袁杰
Owner NANJING VOCATIONAL UNIV OF IND TECH
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