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Bis(N-phenyl)-3-carbazole substituted phenanthroimidazole compound, preparation method thereof and application thereof as electroluminescent device

A technology of phenanthroimidazole and compounds, which is applied in the field of organic light-emitting materials and optoelectronic devices, can solve the problems of unbalanced carrier transport and insufficient purity of luminous color, achieve carrier injection and transport balance, and improve fluorescence quantum Efficiency, the effect of achieving high fluorescence quantum efficiency

Inactive Publication Date: 2020-04-21
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the disadvantages of unbalanced carrier transport and insufficient luminous color purity in the prior art, and provide a bis-N-phenyl-3-carbazole-substituted phenanthroimidazole compound, which The compound can prepare organic electroluminescent devices with good carrier transport ability and high blue light color purity

Method used

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  • Bis(N-phenyl)-3-carbazole substituted phenanthroimidazole compound, preparation method thereof and application thereof as electroluminescent device
  • Bis(N-phenyl)-3-carbazole substituted phenanthroimidazole compound, preparation method thereof and application thereof as electroluminescent device
  • Bis(N-phenyl)-3-carbazole substituted phenanthroimidazole compound, preparation method thereof and application thereof as electroluminescent device

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Embodiment 1

[0054]The bis-N-phenyl-3-carbazole-substituted phenanthroimidazole compound has a molecular structure as shown in formula (I).

[0055] The preparation method of the phenanthroimidazole compound substituted by two N-phenyl-3-carbazoles comprises the steps:

[0056] S1. Add 4-bromobenzaldehyde (1.86g, 10mmol), p-bromoaniline (1.70g, 10mmol), 9,10-phenanthrenequinone (2.08g, 10mmol), ammonium acetate (4.62g, 60mmol) into 100mL of two-necked flask, and added 60mL of glacial acetic acid to obtain a dark brown suspension. After the mixture was stirred at 120° C. for 2 hours, the color of the solution changed from dark brown to black, and the reaction mixture was stirred overnight (12 hours) at room temperature. The crude product was isolated by washing with methanol and filtration, then dried in vacuo. Using silica gel powder as stationary phase, petroleum ether and dichloromethane as eluent (petroleum ether: CH 2 Cl 2 , 1:2) to purify the product to obtain a white powder of bi...

Embodiment 2

[0064] Embodiment 2 performance test

[0065] Taking the double N-phenyl-3-carbazole modified phenanthroimidazole prepared in Example 1 as the test object, test its photophysical properties and other luminescent properties, the test results are as follows Figure 3 to Figure 8 shown.

[0066] image 3 It is the normalized absorption spectrum of molecule M1 under tetrahydrofuran measured by Shimadzu UV-2700 ultraviolet-visible spectrophotometer. The results show that the molecule exhibits the maximum absorption intensity at 250nm, which is attributed to the π-π* transition of the benzene ring.

[0067] Figure 4 The fluorescence emission spectrum of the obtained molecule M1 was tested on an Edinburgh FLS980 at an excitation wavelength of 350 nm. The results show that the molecule emits fluorescence efficiently in tetrahydrofuran solution, and its fluorescence peak is located between 390-440nm, showing deep blue fluorescence emission.

[0068] Figure 5 It is the normalize...

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Abstract

The invention discloses a bis(N-phenyl)-3-carbazole substituted phenanthroimidazole compound, a preparation method thereof and application of the compound serving as an electroluminescent device. Thecompound has a molecular structure shown as a formula (I) shown in the specification. The preparation method comprises the following steps: carrying out a one-pot reaction on 4-bromobenzaldehyde, p-bromoaniline and 9,10-phenanthrenequinone to prepare 4,4-bisbromo-phenanthroimidazole; adding N-phenyl-3-carbazole boric acid, and carrying out a Suzuki reaction under the action of a catalyst tetrakis(triphenylphosphine) palladium, so as to obtain the bis(N-phenyl)-3-carbazole substituted phenanthroimidazole compound. The preparation method is simple and convenient, and large-scale batch preparation can be realized; the compound shown in the formula (I) has good carrier transport capacity, high fluorescence quantum yield in an aggregation state and high blue light color purity, and can be widely applied to organic light-emitting devices, especially stable and efficient dark blue organic light-emitting devices as a light-emitting material.

Description

technical field [0001] The invention relates to the technical field of organic light-emitting materials and their application in optoelectronic devices, more specifically, to bis-N-phenyl-3-carbazole-substituted phenanthroimidazole compounds, their preparation methods and their application as electroluminescent devices. Background technique [0002] With the rise of high-tech products such as large-screen smartphones, tablet computers, and wearable devices, traditional liquid crystal display materials are becoming more and more difficult to meet the increasingly thinner and lower power consumption requirements of mobile terminals. Humans have begun to pay attention to organic electroluminescent devices with advantages such as higher flexibility, thinner thickness, lower power consumption, wider viewing angle, and higher color saturation. Among them, OLED devices are of decisive significance to display technologies such as full-color display and solid-state lighting. [0003...

Claims

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Application Information

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IPC IPC(8): C07D403/14C09K11/06H01L51/50H01L51/54
CPCC07D403/14C09K11/06C09K2211/1029C09K2211/1044H10K85/6572H10K50/11
Inventor 霍延平邱志鹏陈涛邢龙江籍少敏陈思维
Owner GUANGDONG UNIV OF TECH
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