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

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...

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

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