Compound containing tetraphenyl ethylene unit, preparation method and applications thereof

A technology of tetraphenylethylene and compounds, which is applied in the field of optoelectronic devices, can solve the problems of unfavorable carrier transport, increase of conjugation length, spectral red shift, etc., and achieve enhanced hole transport capability, improved device efficiency, and mild reaction conditions. Effect

Inactive Publication Date: 2014-09-17
WUHAN UNIV
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  • Abstract
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  • Application Information

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Problems solved by technology

But the ensuing problem is that the electroluminescence spectrum of these new AIE molecules has been red-shifted to the green or even orange range, because directly connecting tetraphenylethylene to the conjugation sites of these classical units will make the conjugation of the molecules increase in length, resulting in a spectral redshift
[0003] As we all know, the current bottleneck in the research of organic light-emitting diodes lies in the scarcity of high-efficiency blue light and deep blue light materials, because the wide energy gap of blue light materials is not conducive to the transport of carriers in the device to the light-emitting layer.
Although people have adopted various physical or chemical methods to improve the efficiency of blue light devices, such as adopting host-guest doped device configurations and modifying large anti-aggregation groups on the periphery of molecules, etc., the use of these methods will not only increase The fabrication cost of the device also makes the synthesis process more complicated

Method used

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  • Compound containing tetraphenyl ethylene unit, preparation method and applications thereof
  • Compound containing tetraphenyl ethylene unit, preparation method and applications thereof

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Embodiment 1

[0022] The synthesis of embodiment 1 compound Methyl-BTPE, Isopro-BTPE, Ph-BTPE and Cz-BTPE

[0023] (1) Arylamine (R is Or F) (60mmol), sodium bicarbonate (7.56g, 90mmol) and 150mL water were added in a 250mL round bottom flask and stirred vigorously, then the ground powdery elemental iodine (12.7g, 50mmol) was added in several times and ensured The addition was completed within half an hour, and the resulting mixture was continued to react at room temperature for one hour until the color of the iodine element disappeared completely. The reaction solution was suction filtered to obtain crude products 1a-1d, which were directly used in the next reaction. The general structural formula of the compound 1a-1d is where R is followed by H 3 C-(1a), (1b), (1c) and (1d);

[0024] (2) Dissolve compound 1a-1d (30mmol) and copper bromide (8.38g, 37.5mmol) in 150mL acetonitrile solution, then add tert-butyl nitrite (3.87g, 37.5mmol) dropwise to the reaction system . After...

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Abstract

The invention discloses a compound containing a tetraphenyl ethylene unit, a preparation method and applications thereof. The preparation method comprises following steps: taking aniline derivatives as the initial reactants, obtaining the key intermediate diphenylketone through the Friedel-Crafts reactions catalyzed by copper, then obtaining tetraphenyl ethylene mono bromine derivatives and tetraphenyl ethylene mono boric acid ester derivatives through further reactions, and finally obtaining the object compound through the Suzuki coupling reactions. The compound containing a tetraphenyl ethylene unit has a good thermal stability and an excellent aggregation-induced emission property. The fluorescence quantum yield of the solid compound is high, and the fluorescent is blue light emission or dark blue light emission, so the compound can be used as the material of the luminous layers of organic light emitting diodes, which give off blue lights or dark blue lights. The preparation method has the advantages of mild reaction conditions and high yield.

Description

technical field [0001] The invention relates to a compound containing a tetraphenylethylene unit, a preparation method thereof and an application as a blue light or deep blue light organic luminescent material, belonging to the field of photoelectric devices. Background technique [0002] In 2001, the Hong Kong University of Science and Technology Academician Tang Benzhong's research group discovered and reported for the first time a class of molecules with abnormal luminescent behavior. This type of molecule does not emit light or emits very weakly in the solution state, but shows high fluorescence quantum in the aggregated state. Yield. They named this phenomenon "Aggregation-Induced Emission (AIE)", and used a large number of experimental facts to prove that the obstruction of intramolecular rotation in the aggregated state is the main reason for this phenomenon. The discovery of this class of molecules breaks the conventional understanding of light-emitting molecules th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C15/52C07C1/32C07D209/86C09K11/06H01L51/54
CPCY02P20/52
Inventor 李振黄静秦金贵
Owner WUHAN UNIV
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