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Organic red light micromolecule based on feidazole-trans-diphenyl dicyanide ethylene and preparation method and application thereof

A technology of diphenyl dicyanoethylene and phenanthroimidazole is applied in the application field of electroluminescent devices, which can solve the problems of luminous performance such as efficiency, service life, color purity, and carrier injection/transmission backward.

Inactive Publication Date: 2018-09-28
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the three primary colors, the development of green light materials is the most mature. For red light and blue light materials, whether using singlet fluorescent materials or triplet phosphorescent materials, their luminous performance is in terms of efficiency, service life, and color purity. and carrier injection / transport etc. are significantly behind

Method used

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  • Organic red light micromolecule based on feidazole-trans-diphenyl dicyanide ethylene and preparation method and application thereof
  • Organic red light micromolecule based on feidazole-trans-diphenyl dicyanide ethylene and preparation method and application thereof
  • Organic red light micromolecule based on feidazole-trans-diphenyl dicyanide ethylene and preparation method and application thereof

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Embodiment 1

[0070] The preparation of the present embodiment PIDPh comprises the following preparation steps:

[0071] Synthesis of intermediate 2-(4-bromobenzene)-1-phenyl-3a,11b-dihydro-1H-phenanthrene imidazole (PPIBr):

[0072] PPIBr was prepared by a one-pot method. In a 500mL round bottom flask, 9,10-phenanthrenequinone (40mmol, 8.32g), p-bromobenzaldehyde (40mmol, 7.33g), aniline (200mmol, 18.1mL), ammonium acetate (160mmol, 12.33g) were dissolved in In 200mL of glacial acetic acid, stirred and refluxed at 120°C for 4h under nitrogen protection. After the reaction was completed, the reaction system was poured into 100 mL of ice water, and a large amount of precipitates appeared instantly. After suction filtration, the resulting solid was separated and purified by column chromatography (petroleum ether:dichloromethane=1:2, volume ratio) to obtain a white solid (16.3 g, yield: 91%). Mass Spectrum MALDI-TOF(m / z)[M + ]: The test value is 448.74, and the theoretical value is 448.06....

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Abstract

The invention discloses an organic red light micromolecule based on feidazole-trans-diphenyl dicyanide ethylene and a preparation method and application thereof in an electroluminescent device, and belongs to the technical field of organic electroluminescence. Beginning from phenanthrenequinone, a one-pot method is adopted for preparing feidazole raw materials, feidazole and trans-diphenyl dicyanide ethylene are connected through a Suzuki condensation reaction to obtain a novel feidazole derivative of the D-pi-A-pi-D structure adopting feidazole as a donor and adopting the trans-diphenyl dicyanide ethylene as a receptor. The obtained compound has the high fluorescence quantum yield and can be adopted as a luminous layer to be applied in a non-doped or doped organic light-emitting device (OLED), and the prepared device has the advantages of being high in efficiency, low in driving voltage and the like.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to a small organic red light molecule based on phenanthroimidazole-trans-diphenyldicyanoethylene, a preparation method and its application in electroluminescent devices. Background technique [0002] The phenomenon of organic electroluminescence and corresponding research can be traced back to the 1960s. In 1963, Professor Pope of New York University discovered the electroluminescence phenomenon of organic material single crystal anthracene for the first time, and there have been some studies on the electroluminescence phenomenon of single crystals. However, the early light-emitting layer was too thick, resulting in too high driving voltage, which failed to arouse widespread research interest. In 1982, Vincett's research group prepared an anthracene deposition film with a thickness of 0.6 μm, and used metal materials as electrodes (the cathode was alu...

Claims

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Application Information

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IPC IPC(8): C07D235/02C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D235/02C09K2211/1044C09K2211/1007H10K85/6572H10K50/11
Inventor 路萍孙晓艺李金钰
Owner JILIN UNIV
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