A structurally ordered thiophene-thiazole copolymer for organic thin-film transistors

详细信息    查看全文

• 作者：DuGang Chen (1)
  Yan Zhao (2)
  Cheng Zhong (1)
  Gui Yu (2)
  YunQi Liu (2) liuyq@iccas.ac.cn
  JinGui Qin (1) jgqin@whu.edu.cn
• 关键词：thin ; film transistors – copolymer – mobility – atomic force microscopy
• 刊名：SCIENCE CHINA Chemistry
• 出版年：2012
• 出版时间：May 2012
• 年：2012
• 卷：55
• 期：5
• 页码：760-765
• 全文大小：703.0 KB
• 参考文献：1. Kim DH, Lee B-L, Moon H, Kang HM, Jeong EJ, Park J-I, Han K-M, Lee S, Yoo BW, Koo BW, Kim JY, Lee WH, Cho K, Becerril HA, Bao Z. Liquid-crystalline semiconducting copolymers with intramolecular donor-acceptor building blocks for high-stability polymer transistors. J Am Chem Soc, 2009, 131: 6124–6132
  2. Li J, Bao Q, Li CM, Zhang W, Gong C, Chan-Park MB, Qin J, Ong BS. Organic thin-film transistors processed from relatively nontoxic, environmentally friendlier solvents. Chem Mater, 2010, 22: 5747–5753
  3. Shirota Y, Kageyama H. Charge carrier transporting molecular materials and their application in devices. Chem Rev, 2007, 107: 953–1010
  4. Zaumseil J, Sirringhaus H. Electron and ambipolar transport in organic field-effect transistors. Chem Rev, 2007, 107: 1296–1323
  5. Murphy AR, Fréchet JMJ. Organic semiconducting oligomers for use in thin film transistors. Chem Rev, 2007, 107: 1066–1096
  6. Zhang L, Di C, Yu G, Liu Y. Solution processed organic field-effect transistors and their application in printed logic circuits. J Mater Chem, 2010, 20: 7059–7073
  7. Boudreault PT, Wakim S, Tang ML, Tao Y, Bao Z, Leclerc M. New indolo[3,2-b]carbazole derivatives for field-effect transistor applications. J Mater Chem, 2009, 19: 2921–2928
  8. Li Y, Sonar P, Singh SP, Soh MS, van Meurs M, Tan J. Annealing-free high-mobility diketopyrrolopyrrole-quaterthiophene copolymer for solution-processed organic thin film transistors. J Am Chem Soc, 2011, 133: 2198–2204
  9. Lim B, Baeg K-J, Jeong H-G, Jo J, Kim H, Park J-W, Noh Y-Y, Vak D, Park J-H, Park J-W, Kim D-Y. A new poly(thienylenevinylene) derivative with high mobility and oxidative stability for organic thin-film transistors and solar cells. Adv Mater, 2009, 21: 2808–2814
  10. Ong BS, Wu Y, Liu P, Gardner S. Structurally ordered polythiophene nanoparticles for high-performance organic thin-film transistors. Adv Mater, 2005, 17: 1141–1144
  11. Li J, Qin F, Li CM, Bao Q, Chan-Park MB, Zhang W, Qin J, Ong BS. High-performance thin-film transistors from solution-processed dithienothiophene polymer semiconductor nanoparticles. Chem Mater, 2008, 20: 2057–2059
  12. Li Y, Wu Y, Liu P, Birau M, Pan H, Ong BS. Poly(2,5-bis(2-thienyl)-3,6-dialkylthieno[3,2-b]thiophene)s-high-mobility semicon-ductors for thin-film transistors. Adv Mater, 2006, 18: 3029–3032
  13. Bao Z, Dodabalapur A, Lovinger AJ. Soluble and processable regioregular poly(3-hexylthiophene) for thin film field-effect transistor applications with high mobility. Appl Phys Lett, 1996, 69: 4108–4110
  14. Sirringhaus H, Brown PJ, Friend RH, Nielsen MM, Bechgaard K, Langeveld-Voss BMW, Spiering AJH, Janssen RAJ, Meijer EW, Herwig P, de Leeuw DM. Two-dimensional charge transport in self-organized, high-mobility conjugated polymers. Nature, 1999, 401: 685–688
  15. Hamadani BH, Gundlach DJ, McCulloch I, Heeney M. Undoped polythiophene field-effect transistors with mobility of 1 cm2 V?1 s?1. Appl Phys Lett, 2007, 91: 243512–243513
  16. McCulloch I, Heeney M, Chabinyc ML, DeLongchamp D, Kline RJ, C?lle M, Duffy W, Fischer D, Gundlach D, Hamadani B, Hamilton R, Richter L, Salleo A, Shkunov M, Sparrowe D, Tierney S, Zhang W. Semiconducting thienothiophene copolymers: Design, synthesis, morphology, and performance in thin-film transistors. Adv Mater, 2009, 21:1091–1109
  17. Osaka I, Sauvé G, Zhang R, Kowalewski T, McCullough RD. Novel thiophene-thiazolothiazole copolymers for organic field-effect transistors. Adv Mater, 2007, 19: 4160–4165
  18. Abdou MSA, Orfino FP, Son Y, Holdcroft S. Interaction of oxygen with conjugated polymers: Charge transfer complex formation with poly(3-alkylthiophenes). J Am Chem Soc, 1997, 119: 4518–4524
  19. Caronna T, Forte M, Catellani M, Meille SV. Photodegradation and photostabilization studies of poly(3-butylthiophene) in the solid state. Chem Mater, 1997, 9: 991–995
  20. Ong BS, Wu Y, Liu P, Gardner S. High-performance semiconducting polythiophenes for organic thin-film transistors. J Am Chem Soc, 2004, 126: 3378–3379
  21. McCulloch I, Heeney M, Bailey C, Genevicius K, Macdonald I, Shkunov M, Sparrowe D, Tierney S, Wagner R, Zhang W, Chabinyc ML, Kline RJ, Mcgehee MD, Toney MF. Liquid-crystalline semiconducting polymers with high charge-carrier mobility. Nat Mater, 2006, 5: 328–333
  22. Li J, Tan H-S, Chen Z-K, Goh W-P, Wong H-K, Ong K-H, Liu W, Li CM, Ong BS. Dialkyl-substituted dithienothiophene copolymers as polymer semiconductors for thin-film transistors and bulk heterojunction solar cells. Macromolecules, 2011, 44: 690–693
  23. Ando S, Nishida J, Inoue Y, Tokito S, Yamashita Y. Synthesis, physical properties, and field-effect transistors of novel thiophene/thiazolothiazole co-oligomers. J Mater Chem, 2004, 14: 1787–1790
  24. Ando S, Nishida J, Tada H, Inoue Y, Tokito S, Yamashita Y. High-performance n-type organic field-effect transistors based on π-electronics systems with trifluoromethylphenyl groups. J Am Chem Soc, 2005, 127: 5336–5337
  25. Jenekhe SA, Lu L, Alam MM. New conjugated polymers with donor-acceptor architectures: Synthesis and photophysics of carbazole-quinoline and phenothiazine-quinoline copolymers and oligomers exhibiting large intramolecular charge transfer. Macromolecules, 2001, 34: 7315–7324
  26. Zhu Y, Champion RD, Jenekhe SA. Intramolecular charge transfer: Synthesis, optical properties, electrochemistry, and field-effect carrier mobility of thienopyrazine-based copolymers. Macromolecules, 2006, 39: 8712–8719
  27. Yang C, Cho S, Chiechi RC, Walker W, Coates NE, Moses D, Heeger AJ, Wudl F. Visible-near infrared absorbing dithienylcyclopentadienone-thiophene copolymers for organic thin-film transistors. J Am Chem Soc, 2008, 130: 16524–16526
  28. Hassan J, Lavenot L, Gozzi C, Lemaire M. A convenient catalytic route to symmetrical functionalized bithiophenes. Tetrahedron Lett, 1999, 40: 857–858
  29. Suzuki K, Tomura M, Tanka S, Yamashita Y. Synthesis and characterization of novel strong electron acceptors: Bithiazole analogues of tetracyanodiphenoquinodimethane (TCNDQ). Tetrahedron Lett, 2000, 41: 8359–8364
  30. Paek S, Lee J, Lim HS, Lim J, Lee JY, Lee C. The influence of electron-deficient comonomer on chain alignment and OTFT characteristics of polythiophenes. Synth Met, 2010, 160: 2273–2280
  31. Bredas JL, Silbey R, Boudreaux DS, Chance RR. Chain-length dependence of electronic and electrochemical properties of conjugated systems: polyacetylene, polyphenylene, polythiophene, and polypyrrole. J Am Chem Soc, 1983, 105: 6555–6559
  32. De Leeuw DW, Simenon MMJ, Brown AR, Einerhand REF. Stability of n-type doped conducting polymers and consequences for polymeric microelectronic devices. Synth Met, 1997, 87: 53–59
  33. Pommerehne J, Vestweber H, Guss W, Mahrt RF, B?ssler H, Porsch M, Daub J. Efficient two layer leds on a polymer blend basis. Adv Mater, 1995, 7: 551–554
• 作者单位：1. Department of Chemistry and Hubei Key Lab on Organic and Polymeric Optoelectronic Materials, Wuhan University, Wuhan, 430072 China2. Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 China
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chinese Library of Science
  Chemistry
  
• 出版者：Science China Press, co-published with Springer
• ISSN：1869-1870

文摘

This paper reports a new donor-acceptor copolymer semiconductor, PTBTh, comprising bithiophene and bithiazole where the regular coplanar structure and the intramolecular charge transfer are expected to increase the opportunity for π-π stacking and charge transport. The AFM image shows lamellar stacking of the polymer on the surface. The field-effect transistor (FET) properties of PTBTh have been evaluated by a bottom-contact/bottom-gate TFT configuration. The device showed a high hole mobility of 1.14×10?2 cm2 V?1 s?1 and a current on/off ratio of 3×105 with the polymer thin film annealed at a mild temperature of 120 °C when measured under ambient conditions.