Styrene-bisphenanthroimidazole derivative, preparation method therefor and application of styrene-bisphenanthroimidazole derivative

A technology for phenanthroimidazole and derivatives, which is applied in the field of styrene-bisphenanthroimidazole derivatives and its preparation, can solve the problems of low fluorescence quantum yield, poor photothermal stability, and low luminous intensity, and achieve high fluorescence quantum The effect of good yield, good stability, and strong fluorescence performance

Active Publication Date: 2019-09-13
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The primary purpose of the present invention is to overcome the defects of low luminous intensity, low fluorescence quantum yield and poor photothermal stability of existing luminescent materials, and the annihilation of exciton in the aggregated state of phenanthroimidazole is prone to concentration quenching, and to provide a Styrene-Bisphenanthroimidazole Derivatives

Method used

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  • Styrene-bisphenanthroimidazole derivative, preparation method therefor and application of styrene-bisphenanthroimidazole derivative
  • Styrene-bisphenanthroimidazole derivative, preparation method therefor and application of styrene-bisphenanthroimidazole derivative
  • Styrene-bisphenanthroimidazole derivative, preparation method therefor and application of styrene-bisphenanthroimidazole derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] 1. Preparation of Intermediate A

[0057] Mix and dissolve 3.9g of 4-bromo-benzophenone, 4.41g of zinc powder and 50mL of tetrahydrofuran, stir magnetically under the protection of nitrogen, cool to 0°C, inject 4.4ml of titanium tetrachloride, and Stir at -10°C for 30 min, then magnetically stir at 90°C under the protection of nitrogen for a reaction time of 20 h, cool to room temperature, and add 30 ml of dilute hydrochloric acid to quench the reaction. After the reaction, it was purified by extraction and column chromatography (eluent: petroleum ether / dichloromethane) to obtain 3.32 g of Intermediate A.

[0058] The reaction equation is as follows:

[0059]

[0060] 2. Preparation of Intermediate B

[0061] Weigh 1.7g of (4-bromobenzyl) diethyl phosphonate, 1.3g of 4-bromo-diphenmethanone and 130mg of potassium tert-butoxide, add 40mL of tetrahydrofuran, and dissolve to obtain a mixture. Magnetic stirring was carried out at a temperature of °C under the protecti...

Embodiment 2

[0093] 1. Preparation of Intermediate A

[0094] Mix and dissolve 3.9g of 4-bromo-benzophenone, 4.41g of zinc powder and 50mL of tetrahydrofuran, stir magnetically under the protection of nitrogen, cool to 0°C, inject 4.4ml of titanium tetrachloride, and Stir at -10°C for 30 min, then magnetically stir at 90°C under the protection of nitrogen for a reaction time of 20 h, cool to room temperature, and add 30 ml of dilute hydrochloric acid to quench the reaction. After the reaction, it was purified by extraction and column chromatography (eluent: petroleum ether / dichloromethane) to obtain 3.32 g of Intermediate A.

[0095] 2. Preparation of Intermediate B

[0096] Weigh (4-bromobenzyl) diethyl phosphonate, 4-bromo-diphenmethanone and 130 mg of potassium tert-butoxide, control (4-bromobenzyl) diethyl phosphonate and 4-bromo-dibenzone The molar ratio of benzophenone is 1:1.5; add 40mL of tetrahydrofuran and dissolve to obtain a mixture, which is magnetically stirred at a temperatu...

Embodiment 3

[0112] 1. Structural identification of tetraphenylethylene-bisphenanthroimidazole derivatives (BUBPI) and two triphenylethylene-bisphenanthroimidazole derivatives (TriPE-BPI and TriPE-tBu-BPI)

[0113] The hydrogen signals of the products BUBPI, TriPE-BPI and TriPE-tBu-BPI were scanned by nuclear magnetic resonance and their hydrogen signals were identified. The results are as follows Figure 1 to Figure 3 shown.

[0114] Depend on figure 1 It can be seen that the characteristic wave numbers of tetraphenylethylene-bisphenanthroimidazole derivatives (BUBPI) are 8.82, 8.69, 8.62, 7.66, 7.55, 7.40, 7.29, 7.20, 7.16, 7.05, 1.37.

[0115] Depend on figure 2 It can be seen that R 2 , R 3 The characteristic wave numbers of triphenylethylene-bisphenanthroimidazole derivatives (TriPE-BPI) with both H are 8.85, 8.70, 8.63, 7.68, 7.50, 7.25, 7.06, 6.93.

[0116] Depend on image 3 It can be seen that R 2 , R 3 The characteristic wave numbers of triphenylethylene-bisphenanthroimi...

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Abstract

The invention provides a styrene-bisphenanthroimidazole derivative, a preparation method therefor and an application of the styrene-bisphenanthroimidazole derivative. The styrene-bisphenanthroimidazole derivative has a structural general formula represented by a formula (I) shown in the description, wherein R1 is H or phenyl, and R2 and R3 each is H or tert-butyl. According to the styrene-bisphenanthroimidazole derivative, the preparation method therefor and the application of the styrene-bisphenanthroimidazole derivative, triphenylethylene and two phenanthroimidazoles are connected separatelythrough one benzene ring, the phenanthroimidazoles have relatively wide molecular forbidden band, high photo-thermal stability and high fluorescent quantum yield, the styrene-bisphenanthroimidazole derivative keeps high-strength fluorescence emission under the condition of extremely high concentration due to an extreme-twisted structure, i.e., triphenylethylene (or tetraphenylethylene) and introduction of tert-butyl to phenanthroimidazole groups, a phenomenon of exciton annihilation in a phenanthroimidazole aggregated state is overcome, and luminescence wavelength is shorter due to connectionof two phenanthroimidazole groups. Simultaneously, the derivative provided by the invention is good in stability and good in solubility, has high luminescence brightness and high fluorescent quantumyield and can be applied to preparation of luminescent materials and luminescent devices.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials. More specifically, it relates to a styrene-bisphenanthroimidazole derivative and its preparation method and application. Background technique [0002] Electroluminescence refers to the luminescence phenomenon in which the luminescent material is excited to produce an excited state under the excitation of an electric field or current, and then radiates back to the ground state in the form of light. At the beginning, people did a lot of research on inorganic light-emitting materials, but when they were used as host materials to make light-emitting devices, they had certain defects in manufacturing and performance, which limited their further development. In recent years, due to the advantages of high luminous efficiency and fast response speed of organic compounds, people have shifted their attention to organic light-emitting materials, so organic light-emitting materials hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C09K11/06H01L51/50H01L51/54
CPCC07D235/02C09K11/06C09K2211/1007C09K2211/1044H10K85/6572H10K50/11
Inventor 霍延平沈文渊杨庆旦王凯
Owner GUANGDONG UNIV OF TECH
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