journal article·2012-08-22

Solution-Processed and Air-Stable n-Type Organic Thin-Film Transistors Based on Thiophene-Fused Dicyanoquinonediimine (DCNQI) Deriatives

Shiyan Chen, Yan Zhao, Altan Bolag, Jun-ichi Nishida, Yunqi Liu, Yoshiro Yamashita

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Abstract

π-Conjugated systems 2a and 2b containing thiophene-fused DCNQI with long alkyl and trifluoromethylphenyl groups were synthesized as potential active materials for solution-processed and air-stable n-type organic thin-film transistors (OTFTs). The electrochemical measurements revealed that the lowest unoccupied molecular orbital (LUMO) of the compounds have an energy level less than -4.0 eV, indicating air stable n-type materials. The long alkyl groups endowed the compounds good solubility and solution-processability. X-ray diffraction measurements revealed the difference of the molecular arrangement depending on the alkyl groups, which were also observed in the UV-vis absorptions of the films. A relatively good mobility up to 0.003 cm(2) V(-1) s(-1) for 2a by spin-coating was obtained with good air stability.
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Research context

OpenAlex topics: Organic Electronics and Photovoltaics · Conducting polymers and applications · Thin-Film Transistor Technologies

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Key Laboratory of Textile Science & Technology (Ministry of Education), College of Materials Science and Engineering, Donghua University, Shanghai 201620, P.R. China

Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190, China

Department of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama 226-8502, Japan.

References (46)

Show source-provided references
1. Wen Y. · Adv. Mater. · 2010 · 22 · 133110.1002/adma.200901454 ↗
2. Murphy A. R. · Chem. Rev. · 2007 · 107 · 106610.1021/cr0501386 ↗
3. Zaumseil J. · Chem. Rev. · 2007 · 107 · 129610.1021/cr0501543 ↗
4. Mas-Torrent M. · Chem. Soc. Rev. · 2008 · 37 · 82710.1039/b614393h ↗
5. Park Y. D. · Mater. Today · 2007 · 10 · 4610.1016/S1369-7021(07)70019-6 ↗
6. Coropceanu V. · Chem. Rev. · 2007 · 107 · 92610.1021/cr050140x ↗
7. Afzali A. · J. Am. Chem. Soc. · 2002 · 124 · 881210.1021/ja0266621 ↗
8. Payne M. M. · J. Am. Chem. Soc. · 2005 · 127 · 498610.1021/ja042353u ↗
9. Li Y. · Adv. Mater. · 2010 · 22 · 486210.1002/adma.201002313 ↗
10. Li Y. · J. Am. Chem. Soc. · 2011 · 133 · 219810.1021/ja1085996 ↗
11. Ha J. S. · J. Am. Chem. Soc. · 2011 · 133 · 1036410.1021/ja203189h ↗
12. Gao X. · J. Am. Chem. Soc. · 2010 · 132 · 369710.1021/ja910667y ↗
13. Hu Y. · Chem. Mater. · 2011 · 23 · 120410.1021/cm102850j ↗
14. Zhao Y. · Adv. Mater. · 2011 · 23 · 244810.1002/adma.201004588 ↗
15. Wu Q. · Chem. Mater. · 2011 · 23 · 313810.1021/cm201326c ↗
16. Polander L. E. · Chem. Mater. · 2011 · 23 · 340810.1021/cm201729s ↗
17. Usta h. · Acc. Chem. Res. · 2011 · 44 · 50110.1021/ar200006r ↗
18. Yan H. · Nature · 2009 · 457 · 67910.1038/nature07727 ↗
19. Jones B. A. · J. Am. Chem. Soc. · 2007 · 129 · 1525910.1021/ja075242e ↗
20. Yan H. · Adv. Mater. · 2008 · 20 · 339310.1002/adma.200800629 ↗
21. Chen Z. · J. Am. Chem. Soc. · 2009 · 131 · 810.1021/ja805407g ↗
22. Sista P. · Macromol. Rapid Commun. · 2012 · 33 · 910.1002/marc.201100671 ↗
23. Mamada M. · ACS Appl. Mater. Interfaces · 2010 · 2 · 130310.1021/am1001794 ↗
24. Pan H. · J. Am. Chem. Soc. · 2007 · 129 · 411210.1021/ja067879o ↗
25. Takimiya K. · J. Am. Chem. Soc. · 2004 · 126 · 508410.1021/ja0496930 ↗
26. Pan H. · Chem. Mater. · 2006 · 18 · 323710.1021/cm0602592 ↗
27. Zhao X. · Chem. Soc. Rev. · 2011 · 40 · 372810.1039/c0cs00194e ↗
28. Price S. C. · J. Am. Chem. Soc. · 2011 · 133 · 462510.1021/ja1112595 ↗
29. Hou J. · J. Am. Chem. Soc. · 2009 · 131 · 1558610.1021/ja9064975 ↗
30. Huo L. · Angew. Chem., Int. Ed. · 2010 · 49 · 150010.1002/anie.200906934 ↗
31. Huo L. · Macromolecules · 2011 · 44 · 403510.1021/ma200743b ↗
32. Wang M. · J. Am. Chem. Soc. · 2011 · 133 · 963810.1021/ja201131h ↗
33. Jiang J.-M. · Chem. Commun. · 2011 · 47 · 887710.1039/c1cc12040a ↗
34. Hünig S. · J. Mater. Chem. · 1995 · 5 · 146910.1039/JM9950501469 ↗
35. Takahashi K. · Chem. Commun. · 1996 · 227510.1039/cc9960002275 ↗
36. Takahashi K. · J. Org. Chem. · 2000 · 65 · 257710.1021/jo991438o ↗
37. de la Cruz P. · J. Org. Chem. · 1996 · 61 · 6192
38. Shiraishi K. · Polym. J. · 2002 · 34 · 72710.1295/polymj.34.727 ↗
39. Batsanov A. S. · Chem.—Eur. J. · 1998 · 4 · 258010.1002/(SICI)1521-3765(19981204)4:12<2580::AID-CHEM2580>3.0.CO;2-8 ↗
40. Ribierre J. C. · Adv. Mater. · 2010 · 22 · 172210.1002/adma.200903152 ↗
41. Ribierre J. C. · Jpn. J. Appl. Phys. · 2010 · 49 · 01AB0610.1143/JJAP.49.01AB06 ↗
42. Ribierre J.-C. · Adv. Mater. · 2010 · 22 · 404410.1002/adma.201001170 ↗
43. Ie Y. · Chem.—Eur. J. · 2011 · 17 · 475010.1002/chem.201002995 ↗
44. Usta H. · J. Am. Chem. Soc. · 2009 · 131 · 558610.1021/ja809555c ↗
45. de Leeuw D. M. · Synth. Met. · 1997 · 87 · 5310.1016/S0379-6779(97)80097-5 ↗
46. Anthopoulos T. D. · Appl. Phys. Lett. · 2007 · 90 · 12210510.1063/1.2715028 ↗