Tetraphenylethylene-benzophenone-carbazole derivative, crystal and preparation method and application thereof

A technology of carbazole derivatives and tetraphenylethylene, which is applied in the field of organic light-emitting materials, can solve the problems of restricting large-scale applications, reducing luminous intensity, and difficult preparation, etc., and achieves suppression of exciton annihilation, good luminous performance, and high luminous brightness Effect

Active Publication Date: 2019-03-01
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Since the aggregation of luminescent materials containing tetraphenylethylene derivatives will lead to fluorescence quenching (ACQ effect), thereby reducing the luminous intensity, and its preparation is difficult, these problems limit the scale of this type of luminescent materials in the field of light-emitting device preparation application

Method used

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  • Tetraphenylethylene-benzophenone-carbazole derivative, crystal and preparation method and application thereof
  • Tetraphenylethylene-benzophenone-carbazole derivative, crystal and preparation method and application thereof
  • Tetraphenylethylene-benzophenone-carbazole derivative, crystal and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] A tetraphenylethylene-benzophenone-carbazole derivative prepared by the following method:

[0059] S1. Preparation of intermediate Ⅰ

[0060] A. Weigh 1.82g of benzophenone and 1.315g of zinc powder in a 250mL round bottom flask, add 150mL of anhydrous tetrahydrofuran to dissolve, and obtain a mixed solution;

[0061] B. Magnetically stir the mixed solution obtained in step A under the protection of nitrogen, cool to 0°C, inject 4.4mL of titanium tetrachloride, and stir in an ice bath for 30min (generally, the temperature of ice bath stirring can be -10~ 0 ℃, in embodiment 1 is-10 ℃), warm to room temperature, reflux 20h at 90 ℃, along with the carrying out of reaction, the color of reaction solution deepens gradually, turns black from light brown at the beginning, and reaction solution is opaque and turbid state;

[0062] C. After the reaction solution was cooled to room temperature, the reaction was quenched with 1:1 dilute hydrochloric acid (20 mL hydrochloric acid...

Embodiment 2

[0078] A tetraphenylethylene-benzophenone-carbazole derivative, the preparation method thereof is compared with the preparation method of Example 1, the difference is that the temperature of the ice-bath stirring in step S1. of Example 2 is -5 ° C, Time 60min, reflux heating time is 18h;

[0079] Other raw material consumption and operating steps are consistent with embodiment 1.

Embodiment 3

[0081] A kind of tetraphenylethylene-benzophenone-carbazole derivative, its preparation method is compared with the preparation method of embodiment 1, difference is, the time of Friedel-Crafts reaction in the step S2. of embodiment 3 is 5h; Step The temperature of heating and refluxing in S3. is 110°C, and the time is 12h;

[0082] Other raw material consumption and operating steps are consistent with embodiment 1.

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Abstract

The invention discloses a tetraphenylethylene-benzophenone-carbazole derivative, a crystal and a preparation method and application thereof. The tetraphenylethylene-benzophenone-carbazole derivative is named (4-(9H-carbazole-9-yl)phenyl)(4-(1,2,2-triphenylvinyl)phenyl)ketone, and a structural formula is as shown in the specification. The crystal prepared from the tetraphenylethylene-benzophenone-carbazole derivative has unique AIE effect, high luminous intensity, high thermal stability and high solubility, can be used as a novel soluble luminous molecule which is excellent in performance, lowin cost and high in space structural distortion, and has a remarkable economic value in application to preparation of luminous materials, light-emitting devices or intelligent materials. In addition,controllable preparation of the crystal containing the tetraphenylethylene-benzophenone-carbazole derivative is realized.

Description

technical field [0001] The present invention relates to the field of organic luminescent materials, more specifically, to a tetraphenylethylene-benzophenone-carbazole derivative, a crystal, a preparation method and application thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have huge applications in flat panel displays, smartphones, and solid-state lighting due to their light weight, good flexibility, wide operating temperature range, short response time, high brightness and contrast, and wide viewing angles. potential. [0003] The luminescent material is the substance that ultimately undertakes the luminous function in the device. Therefore, the properties of the luminescent material, such as luminous efficiency, luminous lifetime, and luminous chromaticity, have a direct impact on the performance of OLEDs. As a light-emitting material in OLED, it should meet the following conditions: 1) It has high-efficiency solid-state fluorescence without ...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06
Inventor 詹迎迎霍延平谭继华籍少敏潘成强
Owner GUANGDONG UNIV OF TECH
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