Carbazole compounds, and synthesis and application thereof in OLEDs (Organic Light-Emitting diodes)

A compound, carbazole technology, applied in the field of organic electroluminescent materials, can solve problems such as harsh reaction conditions and increased costs, and achieve the effect of improving device performance

Inactive Publication Date: 2015-06-24
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional C-N connection requires harsh reaction conditions, requires expensive noble metal catalysts, and increases the cost of the reaction

Method used

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  • Carbazole compounds, and synthesis and application thereof in OLEDs (Organic Light-Emitting diodes)
  • Carbazole compounds, and synthesis and application thereof in OLEDs (Organic Light-Emitting diodes)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment (1

[0013] Embodiment (1): 2, the synthesis of 3-CzCN

[0014] 2,3-Difluorobenzonitrile (0.36g, 2.6mmol), potassium carbonate (2.23g, 16.1mmol), carbazole (0.95g, 5.7mmol), DMSO 8ml, heated to reflux at 150°C for 12h. Cool to room temperature and pour into 200ml of water to precipitate a large amount of solid, stir for 0.5h, filter with suction to obtain a white solid, and purify by column chromatography to obtain a white solid with a yield of 95%. 1 H NMR (300MHz, CDCl 3 ): δppm 8.06 (d, 2H, J=7.5Hz), 7.84 (t, 1H, J=7.8Hz), 7.74 (d, 4H, J=7.2), 7.07-7.01 (m, 12H).

Embodiment (2

[0015] Embodiment (2): 2, the synthesis of 4-CzCN

[0016] 2,4-Difluorobenzonitrile (0.36g, 2.6mmol), potassium carbonate (2.23g, 16.1mmol), carbazole (0.95g, 5.7mmol), DMSO 8ml, heated to reflux at 150°C for 12h. Cool to room temperature and pour into 200ml of water to precipitate a large amount of solid, stir for 0.5h, filter with suction to obtain a white solid, and purify by column chromatography to obtain a white solid with a yield of 84%. 1 H NMR (300MHz, CDCl 3 ): δppm 8.19-8.13(m, 5H), 7.92(d, 2H, J=5.4Hz), 7.57(d, 2H, J=5.1Hz), 7.50-7.44(m, 4H), 7.38-7.33(m , 6H).

Embodiment (3

[0017] Embodiment (3): 2, the synthesis of 5-CzCN

[0018] 2,5-difluorobenzonitrile (0.36g, 2.6mmol), potassium carbonate (2.23g, 16.1mmol), carbazole (0.95g, 5.7mmol), DMSO 8ml, heated at reflux at 150°C for 12h. Cool to room temperature and pour into 200ml of water to precipitate a large amount of solid, stir for 0.5h, filter with suction to obtain a white solid, and purify by column chromatography to obtain a white solid with a yield of 92%; 1 H NMR (300MHz, CDCl 3 ): δppm 8.20 (t, 5H, J = 5.7Hz), 8.10-8.06 (m, 1H), 7.87 (d, 1H, J = 8.7Hz), 7.58-7.36 (m, 12H).

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Abstract

The invention relates to a class of carbazole compounds, and synthesis and application thereof in OLEDs (Organic Light-Emitting diodes). A method for synthesizing the series of carbazole compounds in one step is developed, wherein raw materials are cheap and easily available, noble metal catalysts are not needed, the operation is simple, the reaction conditions are mild, the production is low in cost and high in yield, and commercialization can be conveniently realized. The invention relates to the field of organic electroluminescence materials, and in particular relates to a material with bipolar carrier transporting performance, which is synthesized by a one-step method, and preparation of organic electroluminescence devices by using the material as an electrophosphorescence body. The material with the bipolar carrier transporting performance contains both carbazole units with hole transport performance and benzonitrile or benzophenone units with electron transport performance, i.e. n-CzCN and n-CzCO compounds.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a class of carbazole compounds, their synthesis and their application in OLEDs. technical background [0002] Organic electroluminescent devices (OLEDs) are self-luminous devices with advantages such as low voltage, wide viewing angle, fast response speed, and good temperature adaptability. They are a new generation of display technology. The principle of organic electroluminescent devices, under the action of an electric field, holes and electrons are injected from the anode and cathode respectively, pass through the hole injection layer, the hole transport layer and the electron injection layer, and the electron transport layer respectively, and recombine in the light-emitting layer to form an excitation layer. The exciton radiation decays and emits light. [0003] One of the keys to improving the efficiency and lifetime of organic electroluminescent devices...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06H01L51/54
CPCC09K11/06C07D209/86C09K2211/1029H10K85/6572
Inventor 陶友田王芳芳梅岭黄维
Owner NANJING UNIV OF TECH
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