Preparation, Characterization, and FET Properties of 3,3',5,5'-Tetra-Phenyldiphenoquinone

Abstract:

In this work, tetraphenyldiphenoquinone (DPQ) was synthesized and characterized by single crystal structure analysis, ultraviolet–visible spectroscopy (UV–Vis) and cyclic voltammetry (CV). DPQ–based organic field-effect transistors (OFET) were fabricated with bottom contact configuration using bare SiO₂/Si substrate and hexamethyldisilazane (HMDS) treated substrate, respectively. The HMDS-treated device showed hole mobility of 8.7 × 10⁻⁷ cm² V⁻¹ s⁻¹, current on/off ratio of 1.2 × 10² and threshold voltage of −39 V. Devices with bare substrate showed no FET behaviors. Finally, film morphology was investigated by X-ray diffraction (XRD) analyses and the results showed that the HMDS treatment exhibits better crystallinity of DPQ on the film thus obtaining FET performance.

• Periodical: Solid State Phenomena (Volume 288)
• Pages: 44-50
• DOI: https://doi.org/10.4028/www.scientific.net/SSP.288.44
• Online since: March 2019
• Authors: Xiao Ying Zhang, Altan Bolag*, Yun Wu, Yoshiro Yamashita
• Keywords: Charge Mobility, Organic Field-Effect Transistors, Tetraphenyldiphenoquinone

References

[1] W.P. Hu, Organic Field-Effect Transistors, Science Press, Beijing, (2011).

[2] S.R. Forrest, M.E. Thompson, Introduction:  Organic Electronics and Optoelectronics, Chem. Rev. 107 (2007) 923-925.

DOI: 10.1021/cr0501590

[3] C.D. Dimitrakopoulos, P.R.L. Malenfant, Organic Thin Film Transistors for Large Area Electronics, Adv. Mater. 14 (2002) 99-117.

DOI: 10.1002/1521-4095(20020116)14:2<99::aid-adma99>3.0.co;2-9

[4] C.L. Wang, H.L. Dong, W.P. Hu, Y.Q. Liu, D.B. Zhu, Semiconducting π-conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics, Chem. Rev. 112 (2012) 2208-2267.

DOI: 10.1021/cr100380z

[5] H.L. Dong, X.L. Fu, J. Liu, Z.R. Wang, W.P. Hu. Key points for high-mobility organic field-effect transistors. Adv. Mater. 25 (2013) 6158-6182.

DOI: 10.1002/adma.201302514

[6] X.K. Gao， Z. Zhao，High Mobility Organic Semiconductors for Field-Effect Transistors，Sci. China Chem. 58 (2015) 947-968.

DOI: 10.1007/s11426-015-5399-5

[7] Y. Yamashita, Organic Semiconductors for Organic Field-Effect Transistors, Sci. Technol. Adv. Mater. 10 (2009) 024313.

[8] M.M. Torrent, C. Rovira, Role of Molecular Order and Solid-State Structure in Organic Field-Effect Transistors, Chem. Rev. 111 (2011) 4833-4856.

DOI: 10.1021/cr100142w

[9] A. Bolag, M. Mamada, J. Nishida, Y. Yamashita，Field-Effect Transistors Based on Tetraphenyldipyranylidenes and the Sulfur Analogues, Chem. Mater. 21 (2009) 4350-4352.

DOI: 10.1021/cm902037w

[10] G.A. Reynolds, C.H. Chen, J.A. Van Allan, J. Org. Chem. 44 (1979) 4456-4458.

[11] M.L. Tang, Z. Bao, Halogenated Materials as Organic Semiconductors, Chem. Mater. 23 (2011) 446-455.

[12] X.G. Li, Y. Wang, W. Hou, X.M. Zhao, Synthesis and Photoconductive Application of Asymmetric Biphenyl Quinone Electron Transport Materials, Industry of Fine Chemicals 23 (2006) 729-732.

[13] M. Mamada, D. Kumaki, J. Nishida, S. Tokito, Y. Yamashita，Novel Semiconducting Quinone for Air-Stable n-Type Organic Field-Effect Transistor, ACS Appl. Mater. Interfaces 2 (2010) 1303-1307.

DOI: 10.1021/am1001794

[14] A.S. Hay, Thermolysis of 3,3',5,5'-tetra-phenyldiphenoquinone, J. org. chem. 36 (1971) 218-219.

[15] C.D. Dimitrakopoulos P.R.L. Malenfant, Organic Thin Film Transistors for Large Area Electronics, Adv. Mater. 14 (2002) 99-117.

DOI: 10.1002/1521-4095(20020116)14:2<99::aid-adma99>3.0.co;2-9

[16] C.M. Cardona, W. Li, A.E. Kaifer, D. Stockdale, G.C. Bazan, Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications, Adv. Mater. 23 (2011) 2367-2371.

DOI: 10.1002/adma.201004554