Anthracenes, Anthraquinones For Semiconductors
Anthracene is a condensed aromatic hydrocarbon containing three rings. Anthracene is a colorless flaky crystal with blue-violet fluorescence. Anthracene is the least conjugated acene class of materials. Anthracene can be oxidized by nitric acid to form anthraquinone. Anthraquinone compounds take anthracene as the parent nucleus, and there are often substituents such as hydroxyl, methyl, methoxy and carboxyl groups on the parent nucleus. Anthracene has good hole transport and high chemical stability. Anthracene without group modification has a planar molecular structure, and it is easy to aggregate between molecules to form crystals. The substitution modification at the 9, 10 positions of anthracene can reduce the aggregation between anthracene molecules, make the film formation of anthracene derivatives more stable, and also improve the transport ability of carriers. Anthracene and anthraquinone compounds can be used as semiconductor materials in the fields of electronic devices and light-emitting devices due to their excellent luminescence properties, high transmission efficiency, easy structure modification, good solubility, and easy film formation and crystallization.
Figure 1. Chemical structure of anthracene, anthraquinone
Applications:
- P-type organic semiconductor materials: The most commonly used structural unit in π-conjugated systems is the benzene ring. The π electrons are evenly distributed inside the benzene ring molecule, which forms a relatively strong interaction force between the molecules, thereby forming an orderly and tight solid-state stacking between the molecules, which is more suitable for the transport of holes between the molecules. Therefore, extending the number of benzene rings can effectively improve the mobility. Anthracene and anthraquinone compounds belong to the acene group, have multiple benzene rings, and are a class of P-type semiconductor materials with excellent performance. In addition, the hole transport ability of this type of semiconductor material can be further improved by the structural modification of anthracene and anthraquinone.
- Organic Field Effect Transistor: Anthracene and anthraquinone derivatives are important semiconductor materials in organic field effect transistors. Such compounds are easy to purify, form single crystals easily, and can be prepared into thin-film devices. The advantage is that the easy-to-crystallize compound can improve the quality of the film by increasing the grain size while ensuring the continuity of the film, and develop single crystal devices to improve the field effect performance. Through the design and optimization of the molecular structure of anthracene and anthraquinone compounds, the performance of transistors can be significantly improved.
- Electroluminescent material: Anthracene has high fluorescence quantum efficiency, and various luminescent materials can be obtained by substitution modification on its carbon atoms. Anthracene and anthraquinone small-molecule materials have the advantages of strong chemical structure modification, easy purification, and wide color range, and are widely used in organic light-emitting devices. In order to further improve the luminous efficiency of such molecules, optimization can be carried out from the following two aspects. On the one hand, the introduction of bulky groups or the formation of non-coplanar twisted structures can reduce intermolecular aggregation, reduce fluorescence quenching, and improve the fluorescence quantum efficiency of luminescent materials. On the other hand, introducing hole-transporting groups and electron-transporting groups into molecules balances the carrier transport capability and improves the luminescence performance of the device.
Reference
- Yanan Zhu,Xiuru Xu,Xuepeng Zhang,Yaowu He,Xianzhe Zeng,Imran Murtaza,Hong Meng. Computational screening and molecular design of anthracene-based semiconductors [J].Organic Electronics, 2018, 61, 87-95.
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