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Benzamidine derivative as well as preparation method and application thereof

A technology of benzamide and derivatives, applied in the field of aggregation-induced luminescent materials, achieves the effects of high yield, fast reaction rate, and overcoming the problem of aggregation and quenching

Active Publication Date: 2019-05-17
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But at present, the fluorescence quenching problem caused by aggregation has a very adverse effect on most light-emitting materials, and the light-emitting layer materials in electroluminescent devices must necessarily require solid-state thin films, which makes this problem urgently needed to be solved

Method used

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  • Benzamidine derivative as well as preparation method and application thereof
  • Benzamidine derivative as well as preparation method and application thereof
  • Benzamidine derivative as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Under nitrogen protection, aniline (931mg, 10mmol), benzil (420mg, 2 mmol), 4-diphenylaminobenzaldehyde (546mg, 2mmol), and ammonium acetate (617mg, 8mmol) were dissolved in acetic acid (20mL) solvent During the reaction, the system was refluxed for 14 hours. After the system is cooled, add deionized water, a large amount of white solid is precipitated, filter, extract the obtained white solid with dichloromethane and deionized water, combine the organic phase, and add anhydrous MgSO to the obtained organic phase 4 After drying, it was concentrated under reduced pressure, and then separated and purified by column chromatography. The stationary phase was 300-400 mesh silica gel, and the mobile phase was a mixed solvent of dichloromethane:petroleum ether=3:1. Finally, 916mg of a white solid intermediate was obtained. The rate is 85%. 1H NMR(500MHz,Tol)δ8.07–8.02(m,2H), 7.57–7.51(m,2H),7.19(t,J=7.7Hz,2H),7.09–7.03(m,2H),6.99 ( dd,J=4.2,2.9Hz,8H),6.92(ddd,J=6....

Embodiment 2

[0031]

[0032] According to the synthesis of compound 1, the steps were the same, and 4-dimethylaminobenzaldehyde was used instead of 4-diphenylaminobenzaldehyde to obtain 270 mg of yellow powdery compound with a yield of 65%. 1 H NMR (500 MHz, DMSO) δ7.61(dd, J=8.1, 3.6Hz, 6H), 7.51(t, J=7.4Hz, 1H), 7.39(t, J=7.4Hz, 1H), 7.34( dd,J=12.7,4.8Hz,2H),7.32–7.21(m,6H),7.10(t,J=7.2Hz,1H),6.64(d,J=9.1Hz,2H),2.96(s,6H ). MS (ESI) theoretical value m / z: 415.5, measured value: 416.5 (M + ).

Embodiment 3

[0034]

[0035]According to the synthesis of compound 1, the procedure was the same, and 9-ethyl-9H-carbazole-3-carbaldehyde was used instead of 4-diphenylaminobenzaldehyde to obtain 312 mg of yellow powdery compound with a yield of 60%. 1H NMR (500MHz,DMSO)δ8.69(d,J=1.7Hz,1H),8.21(d,J=7.8Hz,1H), 7.86(dd,J=8.7,1.8Hz,1H),7.71–7.63 (m,5H),7.62(d,J=8.7Hz,1H),7.52(ddd,J=11.9,9.2,4.3Hz,2H),7.46–7.41(m,2H),7.37(dd,J=15.2 ,7.7Hz,3H),7.30–7.22(m,5H),7.09(t,J=7.4Hz,1H),4.44(q, J=7.1Hz,2H),1.29(t,J=7.1Hz,3H ). MS (ESI) theoretical value m / z: 521.6, measured value: 522.8 (M + ).

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Abstract

The invention discloses a benzamidine derivative as well as a preparation method and an application thereof. The benzamidine derivative has aggregation-induced emission performance, and has quite highfluorescence quantum efficiency being 50% or higher in a solid thin-film state, and therefore, the common problem of aggregation quenching of a luminescent material at present is solved. An OLED (organic light-emitting device) prepared from the material as a luminescent layer has excellent performance. Besides, by means of photooxidation in the preparation method, the reaction rate and the yieldare high, any catalyst is not needed, and the preparation method accords with the characteristics of green chemistry.

Description

(1) Technical field [0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to an aggregation-induced luminescence material of benzimide derivatives, which can be used in flat panel display devices, light-emitting diodes or electronic imaging equipment. (2) Background technology [0002] Nowadays, with the advent of the information society, the development of multimedia technology is particularly important, and people have higher and higher requirements for flat panel display performance. In addition to the most widely used cathode ray tubes and liquid crystal displays on the market. In recent years, three new display technologies have emerged: plasma displays, field emission displays, and organic electroluminescent displays. As a new generation of flat-panel display technology, organic electroluminescent devices have the characteristics of all-solid-state self-luminescence, fast response speed, and ultra-thin, so it can...

Claims

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Application Information

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IPC IPC(8): C07C251/28C07C249/02C07D209/86C09K11/06H01L51/50H01L51/54
Inventor 李维军俞越张诚王士昭陈见爱
Owner ZHEJIANG UNIV OF TECH
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