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Diaza [6] helicene compound, synthetic method thereof and application of diaza [6] helicene compound in organic light-emitting diode

A synthesis method and compound technology, applied in the field of diaza[6]helicene compounds and their synthesis, can solve the problems of poor solubility, low yield, enhanced interaction force, etc., and achieve easy popularization and application and reaction operation Simple, cost-reducing effect

Inactive Publication Date: 2015-01-07
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of many helicene compounds takes a long time and the yield is low; and with the increase of the conjugated system, the interaction force between the helicene molecules with a rigid structure increases, resulting in poor solubility. For related reports, see L .Liu, et al.J.Org.Chem.1991,56,3769.; F.B.Mallory, et al.J.Am.Chem.Soc.1997,119,2119
In addition, the lack of active sites for introducing functional groups is also a very serious problem in the synthesis of helicene derivatives (see A.Rajca, et al.J.Org.Chem.2009,74,7504.)
Have not yet seen any reports on this type of helicene compound and its synthesis and application

Method used

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  • Diaza [6] helicene compound, synthetic method thereof and application of diaza [6] helicene compound in organic light-emitting diode
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  • Diaza [6] helicene compound, synthetic method thereof and application of diaza [6] helicene compound in organic light-emitting diode

Examples

Experimental program
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Effect test

Embodiment 1

[0071] Example 1: Preparation of 7-hexyl-diaza[6]helicene I (a)

[0072]

[0073] Specific steps are as follows:

[0074] (1) the organic solvent benzene is purified by atmospheric distillation, and stored under an inert atmosphere for later use;

[0075] (2) trans-9-hexyl-3-(2-quinoline-vinyl)carbazole (Ⅱa, 0.45mmol) and iodine (I 2 , 0.46mmol) join in the 500ml organic solvent benzene that step (1) purifies, stir rapidly while dissolving, after dissolving completely, logical inert gas 30 minutes;

[0076] (3) under the continuous stirring situation, 18ml propylene oxide is added in the solution of step (2) gained, make the concentration of propylene oxide in the solution be 0.51 mol / liter;

[0077] (4) irradiating the solution obtained in step (3) through quartz glass with a high-pressure mercury lamp of 500W for 10 minutes to the end of the reaction to obtain a crude product;

[0078] (5) The solvent is evaporated in vacuo, and the crude product obtained is dissolved ...

Embodiment 2

[0087] Example 2: Preparation of 11-bromo-7-hexyl-diaza[6]helicene I (b) The chemical reaction formula is as follows:

[0088]

Embodiment 3

[0089] Example 3: Preparation of 11-bis(trimethylphenyl)boryl-7-hexyl-diaza[6]helicene I (c) The chemical reaction formula is as follows:

[0090]

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Abstract

The invention provides a diaza [6] helicene compound based on carbazole and quinoline and a synthetic method and application of the diaza [6] helicene compound. The diaza [6] helicene compound with a photoelectric function is prepared by taking the carbazole and the quinoline as raw materials and adopting a photocatalytic closed-loop method. The synthetic method provided by the invention has simple synthetic means and is easy to apply, and the preparation cost is reduced since a common low-cost reagent is used. The diaza [6] helicene (I) based on the carbazole and the quinoline has very good solubility in different organic solvents, is favorable to the purification and membrane preparation of the compound and can be used for obtaining multiple aromatic fused-heterocyclic compounds by being introduced into different substituent groups. The invention also provides the application of the diaza [6] helicene compound as a luminescent material in an organic light-emitting diode. The diaza [6] helicene (I) based on the carbazole and the quinoline can be applied to the fields of organic field effect tubes, organic electroluminescence, organic second-order nonlinearity, photovoltaic materials, fluorescent probes, laser dyes and the like.

Description

technical field [0001] The present invention relates to a class of diaza[6]helicene compounds based on carbazole and quinoline and their synthesis method and application, in particular to the preparation of aza[6]helicene compounds by photocatalytic ring-closing reaction method and their application in organic light emitting applications in diodes. Background technique [0002] Helicene is a class of polycyclic aromatic compounds with a helical structure formed by the ortho-condensation of multiple aromatic rings. There is a non-planar molecular structure in the helicene molecule. Carbazole is a well-known blue light-emitting group; the NH on the structure can be replaced by functional groups. The introduction of carbazole groups into helicene molecules is beneficial to obtain blue light-emitting materials. Helicene compounds are widely used in organic electroluminescence, organic field effect transistors, asymmetric catalysis, organic second-order nonlinearity, chiral li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07F5/02H01L51/54
CPCC07D471/04C07F5/027H10K85/657H10K85/6572Y02E10/549Y02P70/50
Inventor 刘陟华万鸣张保杰郭巍崔得良
Owner SHANDONG UNIV
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