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Novel piezoluminescence material with thermal activation delayed fluorescence and aggregation-induced emission properties and synthetic method and application of novel piezoluminescence material

A technology of aggregation-induced luminescence and thermal activation delay, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of low luminous efficiency of piezoluminescent materials, etc. The effect of a simple synthesis process

Active Publication Date: 2014-01-01
SUN YAT SEN UNIV
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Problems solved by technology

[0004] The purpose of the present invention is to overcome the problem of low luminescence efficiency of piezoluminescent materials, and provide a novel piezoluminescent material with thermally activated delayed fluorescence and aggregation-induced luminescent properties, which utilizes thermally activated delayed fluorescence and aggregation-induced luminescent properties of compound molecules , improve the luminous efficiency and luminous intensity of piezoluminescent materials

Method used

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  • Novel piezoluminescence material with thermal activation delayed fluorescence and aggregation-induced emission properties and synthetic method and application of novel piezoluminescence material
  • Novel piezoluminescence material with thermal activation delayed fluorescence and aggregation-induced emission properties and synthetic method and application of novel piezoluminescence material
  • Novel piezoluminescence material with thermal activation delayed fluorescence and aggregation-induced emission properties and synthetic method and application of novel piezoluminescence material

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preparation example Construction

[0018] The synthesis method of the above-mentioned luminescent material is as follows: react carbazole or substituted carbazole intermediate with 4,4'-difluorodiphenyl sulfone to obtain monofluorodiphenyl sulfone with carbazolyl or substituted carbazolyl at one end, and then react with Reaction of phenothiazine or substituted phenothiazine intermediates. The described substituted carbazole intermediate and substituted phenothiazine intermediate are commercially available products, or the alkyl group is connected to carbazole and phenothiazine through Friedel-Crafts alkylation reaction, or it is formed by using Suzuki couple The joint reaction connects an aromatic group or an aromatic heterocyclic group to carbazole and phenothiazine. Specifically include the following steps:

[0019] The first step: synthesis of alkyl or aryl substituted carbazole or phenothiazine intermediates.

[0020] Utilize Friedel-Crafts alkylation reaction to prepare alkyl-substituted carbazole or phe...

Embodiment 1

[0032] (1) Add carbazole (3.34g, 0.02mol), 4,4'-difluorodiphenylsulfone (5.09g, 0.02mol) into a three-neck flask, add 100mL N,N-dimethylformamide (DMF) 1. Triethylamine (2.02g, 0.02mol), stirred and blown with argon, heated to 90°C for 24h. Extract with water and dichloromethane, dry the organic phase with anhydrous sodium sulfate, and spin dry in a rotary evaporator under vacuum to obtain a crude product. Purification is carried out by silica gel column chromatography, and a mixed solvent of n-hexane and dichloromethane in a certain volume ratio is used as an eluent. Yield 68%.

[0033]

[0034](2) Add phenothiazine (1.99g, 0.01mol), carbazole monofluorodiphenyl sulfone (4.01g, 0.01mol) into a three-neck flask, add 50mL N,N-dimethylformamide (DMF), Potassium tert-butoxide (0.96 g, 0.01 mol) was heated to 90° C. for 24 h after stirring and flowing argon. Extract with water and dichloromethane, dry the organic phase with anhydrous sodium sulfate, and spin dry in a rotary ...

Embodiment 2

[0037] Referring to the step (1) of Example 1 for the synthesis of tert-butylcarbazole-substituted monofluorodiphenyl sulfone (yield rate is 70%), and then referring to step (2) to utilize tert-butylphenothiazine to synthesize the final product, the yield rate is 75%. %, the solid fluorescence efficiency is 92%.

[0038]

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Abstract

The invention discloses a novel piezoluminescence material with thermal activation delayed fluorescence and aggregation-induced emission properties and a synthetic method and the application of the novel piezoluminescence material. The core structure of the novel piezoluminescence material is carbazole phenothiazine substituted diphenyl sulfone, and the novel piezoluminescence material has a piezoluminescence property, the thermal activation delayed fluorescence property and the aggregation-induced emission property. The synthetic method of the novel piezoluminescence material is simple in process, purification is easy, and the obtained novel piezoluminescence material is high in piezoluminescence intensity and suitable for preparing non-doping luminescent layer materials in pressure sensors or anti-counterfeiting trademark or organic electroluminescent material devices.

Description

technical field [0001] The invention belongs to the technical field of organic piezoluminescence intelligent materials, in particular to a piezoluminescence material with an asymmetric structure containing diphenyl sulfone and carbazole phenothiazine and a synthesis method thereof. Background technique [0002] Piezoluminescent materials, also known as mechanoluminescent materials or triboluminescent materials, are an important class of smart materials. They have huge potential applications in the fields of pressure sensors, material stress damage detection, and trademark anti-counterfeiting. Attention (Yllen K M, Scherf U. Organic Light-Emitting Devices: Synthesis, Properties and Applications. Weinheim: Wiley-VCH, 2006). Traditional piezoluminescent materials are mainly inorganic compounds and complexes containing lanthanide metal ions. Unlike organic compounds, inorganic compounds and complexes are difficult to make thin films for trademark anti-counterfeiting and other f...

Claims

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Application Information

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IPC IPC(8): C07D417/12C09K11/06
CPCC07D417/12C09K11/06C09K2211/1037
Inventor 池振国许适当彭帮银毛竹周勰张艺刘四委许家瑞
Owner SUN YAT SEN UNIV
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