Donor-acceptor compound light-emitting material based on dicyanopyrazine and dicyanobenzopyrazine derivative, and electroluminescent device for preparation

A technology of electroluminescent devices and pyrazine derivatives, applied in the field of organic electroluminescence, which can solve the problems of large efficiency roll-off and limited applications

Inactive Publication Date: 2018-01-19
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its devices often have a large efficiency roll-off under high brightness
In addition, there are few high-performance red and deep red TADF materials, which limits its application in full-color display and white lighting.

Method used

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  • Donor-acceptor compound light-emitting material based on dicyanopyrazine and dicyanobenzopyrazine derivative, and electroluminescent device for preparation
  • Donor-acceptor compound light-emitting material based on dicyanopyrazine and dicyanobenzopyrazine derivative, and electroluminescent device for preparation
  • Donor-acceptor compound light-emitting material based on dicyanopyrazine and dicyanobenzopyrazine derivative, and electroluminescent device for preparation

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of compound 1:

[0033]

[0034] 4-bromophenacyl bromide (10mmol), diaminomaleonitrile (12mmol) was added in 50mL water, N 2 Under protection, cetyltrimethylammonium bromide (CTAB, 2.5mmol) was added, and the oil bath was heated to reflux for 8 hours to stop the reaction. After washing and drying, a yellow powdery brominated intermediate was obtained. Since this intermediate had extremely poor solubility, it was directly carried to the next step without further purification. Bromo intermediate (3mmol), carbazole (6.6mmol), cesium carbonate (24mmol), tris(dibenzylideneacetone) dipalladium (0.15mmol), tri-tert-butylphosphine (0.15mmol), o-xylene (80mL) into the three-necked bottle, N 2 Under protection, heat and reflux in an oil bath for 24 hours to stop the reaction, pour the reaction mixture into distilled water, extract with dichloromethane, concentrate and separate by column chromatography (silica gel, dichloromethane) and vacuum dry t...

Embodiment 2

[0035] Embodiment 2: the synthesis of compound 2:

[0036]

[0037] According to the synthesis of compound 1, the steps are the same, and compound 3,6-dimethylcarbazole is used to replace compound carbazole (the molar amount is the same) to obtain orange powder compound 2 (0.66g, yield 55%). Molecular ion mass: 399.19 (calculated value: 399.15); theoretical element content (%) C 26 h 17 N 5 : C, 78.18; H, 4.29; N, 17.53; Measured element content (%): C, 78.22; H, 4.35; N, 17.43. The above analysis results indicated that the obtained product was the expected product.

Embodiment 3

[0038] Embodiment 3: the synthesis of compound 3:

[0039]

[0040] According to the synthesis of compound 1, the steps are the same, and compound 2,7-dimethylcarbazole is used instead of compound carbazole to obtain orange powder compound 3 (0.63g, yield 53%), and the molecular ion mass determined by mass spectrometry is: 399.19 (calculated value: 399.15); theoretical element content (%) C 26 h 17 N 5 : C, 78.18; H, 4.29; N, 17.53; Measured element content (%): C, 78.25; H, 4.37; N, 17.38. The above analysis results indicated that the obtained product was the expected product.

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Abstract

The invention relates to a donor-acceptor compound light-emitting material based on a dicyanopyrazine and dicyanobenzopyrazine derivative, and an electroluminescent device for preparation, and belongsto the technical field of organic electroluminescence. According to the present invention, the dicyanopyrazine and dicyanobenzopyrazine derivative as the good electron acceptor nucleus can be linkedto different donor groups through a Suzuki reaction or Ullmann reaction to synthesize a series of electron donor-acceptor type organic small molecule light-emitting materials, wherein the materials have characteristics of large rigid planar skeleton, good thermal stability and high TADF fluorescence quantum yield, can achieve deep red light emission and near infrared light emission, are used for preparing deep red light and near infrared electroluminescent devices, and further have characteristics of simple synthesis, high yield, easy purification and the like. According to the present invention, the electroluminescent device has one or a plurality of light-emitting layers, and at least one layer of the light-emitting layer of the electroluminescent device contains one or a plurality of the compounds of the present invention, wherein further 0.1-100.0% by mass of the compound of the present invention is doped in the main body material so as to prepare the light emitting layer.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to a kind of donor-acceptor compound luminescent material based on dicyanopyrazine and dicyanobenzopyrazine derivatives and an electroluminescent device used for the preparation. Background technique [0002] In the early 1960s, Pope et al. first reported the phenomenon of organic electroluminescence. When they applied a high voltage of 400 volts on both sides of anthracene single crystal, they observed the blue light emitted by anthracene (see M.Pope, H.Kallmann and P. Magnante, J. Chem. Phys., 1963, 38, 2042). However, due to the difficulty of growing single crystals and the high driving voltage of the device, the process they used has little practical use. Until 1987, C.W.Tang et al. of Kodak Corporation of the United States used ultra-thin film technology to use aromatic amines with better hole transport effects as the hole transport layer, alumin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D241/24C07D401/10C07D413/10C07D403/14C07D417/10C07D241/42C07D403/04C07D417/04C09K11/06H01L51/50H01L51/54
Inventor 王悦
Owner JILIN UNIV
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