Anthracene Derivatives Substituted with Phenyl or Pentafluorophenyl for Organic Thin Film Transistors

作者：Wang Hui; Lim Jong Sun; Lee Changjin; Kim Dong Wook^*

来源：Journal of Nanoscience and Nanotechnology, 2011, 11(5): 4532-4539.

DOI：10.1166/jnn.2011.3652

• Anthracene Derivatives
• Organic Semiconductor
• Molecular Packing
• Organic thin Film Transistors

Four anthracene derivatives (TIPSAntP, TIPSAntFP, TIPSAntPA and TIPSAntFPA) containing phenyl or pentafluorophenyl have been synthesized by using Suzuki coupling or Sonogashira cross-coupling reactions. DSC measurement showed that TIPSAntP and TIPSAntFP were crystalline and thermally stable to 300 degrees C under nitrogen atmosphere, comparing to TIPSAntPA and TIPSAntFPA with acetylene. From cyclic voltammetry measurement, it can be observed that all compounds were electrochemically stable in the voltage range of -2.0 similar to 2.0 V. The obtained data revealed that fluorinated phenyl groups could decrease HOMO as well as LUMO levels of the compounds. UV-vis absorption and fluorescent emission spectra of them showed red shift in solid film state in comparison to their solution state, revealing that the molecular packing formed in solid state. Further proofs for the study of the packing order of crystals by X-ray analysis showed that phenyl groups provided TIPSAntP and TIPSAntPA planar conjugated unit along the anthracene core and favorable face-to-face interactions between their neighboring molecules. Fluorinated phenyl groups were twisted to the anthracene core and formed interleaved layer packing in TIPSAntFP. Preliminary device results were achieved from TIPSAntP and TIPSAntPA with p-type mobility of 10(-5) and similar to 10(-6) cm(2)/V . s, respectively, and n-type mobility for TIPSAntFP as similar to 10(-7) cm(2)/V . s.

• 出版日期2011-5