Synthesis and Characterization of Fluorenone-Based Donor-Acceptor Small Molecule Organic Semiconductors for Organic Field-Effect Transistors

Abstract

In this study, a series of new fluorenone-based small molecules were synthesized and characterized as organic semiconductors for organic field-effect transistors. Thermal, optical, and electrochemical properties of the new compounds were characterized. Furthermore, thin films of the developed compounds were employed as organic semiconductors, and vacuum-deposited film of fluorenone derivative with alkylated double thiophene exhibited p-channel device characteristics with hole mobility as high as 0.02 cm2/Vs and current on/off ratio of 107. In addition, surface morphology and microstructure of vacuum deposited films were analyzed and correlated with the electrical characteristics.

This is a preview of subscription content, log in to check access.

References

  1. (1)

    L. Zhang, C.-A. Di, G. Yu, and Y. Liu, J. Mater. Chem., 20, 7059 (2010).

    CAS  Google Scholar 

  2. (2)

    A. F. Paterson, S. Singh, K. J. Fallon, T. Hodsden, Y. Han, B. C. Schroeder, H. Bronstein, M. Heeney, I. McCulloch, and T. D. Anthopoulos, Adv. Mater., 30, 1801079 (2018).

    Google Scholar 

  3. (3)

    Y. Yamashita, Sci. Technol. Adv. Mat., 10, 024313 (2009).

    Google Scholar 

  4. (4)

    P. Y. Huang, L. H. Chen, Y. Y. Chen, W. J. Chang, J. J. Wang, K. H. Lii, J. Y. Yan, J. C. Ho, C. C. Lee, and C. Kim, Chem. Eur., 19, 3721 (2013).

    CAS  Google Scholar 

  5. (5)

    B. Geffroy, P. Le Roy, and C. Prat, Polym. Int., 55, 572 (2006).

    CAS  Google Scholar 

  6. (6)

    R.-P. Xu, Y.-Q. Li, and J.-X. Tang, J. Mater. Chem. C, 4, 9116 (2016).

    CAS  Google Scholar 

  7. (7)

    P. Cheng, G. Li, X. Zhan, and Y. Yang, Nat. Photonics, 12, 131 (2018).

    CAS  Google Scholar 

  8. (8)

    O. Inganas, Adv. Mater., 30, 1800388 (2018).

    Google Scholar 

  9. (9)

    P. Lin and F. Yan, Adv. Mater., 24, 34 (2012).

    PubMed  Google Scholar 

  10. (10)

    L. Torsi, M. Magliulo, K. Manoli, and G. Palazzo, Chem. Soc. Rev., 42, 8612 (2013).

    CAS  PubMed  Google Scholar 

  11. (11)

    H. Usta and A. Facchetti, in Large Area and Flexible Electronics, Wiley-VCH, Weinheim, 2015, pp 1–100.

    Google Scholar 

  12. (12)

    Y. Lin, Y. Li, and X. Zhan, Chem. Soc. Rev., 41, 4245 (2012).

    CAS  PubMed  Google Scholar 

  13. (13)

    Y. Mei, M. A. Loth, M. Payne, W. Zhang, J. Smith, C. S. Day, S. R. Parkin, M. Heeney, I. McCulloch, and T. D. Anthopoulos, Adv. Mater., 25, 4352 (2013).

    CAS  PubMed  Google Scholar 

  14. (14)

    J. E. Anthony, M. Heeney, and B. S. Ong, MRS Bull., 33, 698 (2008).

    CAS  Google Scholar 

  15. (15)

    S.-L. Suraru, U. Zschieschang, H. Klauk, and F. Wurthner, Chem. Commun., 47, 1767 (2011).

    CAS  Google Scholar 

  16. (16)

    K. Müllen and W. Pisula, J. Am. Chem. Soc., 137, 9503 (2015).

    PubMed  Google Scholar 

  17. (17)

    R. Ozdemir, D. Choi, M. Ozdemir, G. Kwon, H. Kim, U. Sen, C. Kim, and H. Usta, J. Mater. Chem. C, 5, 2368 (2017).

    CAS  Google Scholar 

  18. (18)

    S. Vegiraju, G. Y. He, C. Kim, P. Priyanka, Y. J. Chiu, C. W. Liu, C. Y. Huang, J. S. Ni, Y. W. Wu, and Z. Chen, Adv. Funct. Mater., 27, 1606761 (2017).

    Google Scholar 

  19. (19)

    A. Bagui, R. Datt, V. Gupta, and S. P. Singh, Chem. Commun., 53, 12790 (2017).

    Google Scholar 

  20. (20)

    F. Lincker, B. Heinrich, R. De Bettignies, P. Rannou, J. Pecaut, B. Grevin, A. Pron, B. Donnio, and R. Demadrille, J. Mater. Chem., 21, 5238 (2011).

    CAS  Google Scholar 

  21. (21)

    P. Sonar, T.-J. Ha, and A. Dodabalapur, Chem. Commun., 49, 1588 (2013).

    CAS  Google Scholar 

  22. (22)

    F. Lincker, A.-J. Attias, F. Mathevet, B. Heinrich, B. Donnio, J.-L. Fave, P. Rannou, and R. Demadrille, Chem. Commun., 48, 3209 (2012).

    CAS  Google Scholar 

  23. (23)

    W. Porzio, S. Destri, U. Giovanella, M. Pasini, T. Motta, D. Natali, M. Sampietro, and M. Campione, Thin Solid Films, 492, 212 (2005).

    CAS  Google Scholar 

  24. (24)

    K. Cho, M. R. Reddy, D. Kim, D. Ho, C. Yun, S. Seo, and C. Kim, Mol. Cryst. Liq. Cryst., 690, 56 (2019).

    CAS  Google Scholar 

  25. (25)

    C. J. Lim, Y. Lei, B. Wu, L. Li, X. Liu, Y. Lu, F. Zhu, B. S. Ong, X. Hu, and S.-C. Ng, Tetrahedron Lett., 57, 1430 (2016).

    CAS  Google Scholar 

  26. (26)

    R. Demadrille, N. Delbosc, Y. Kervella, M. Firon, R. De Bettignies, M. Billon, P. Rannou, and A. Pron, J. Mater. Chem., 17, 4661 (2007).

    CAS  Google Scholar 

  27. (27)

    C. Qin, A. Islam, and L. Han, J. Mater. Chem., 22, 19236 (2012).

    CAS  Google Scholar 

  28. (28)

    T. T. Do, K. Rundel, Q. Gu, E. Gann, S. Manzhos, K. Feron, J. Bell, C. R. McNeill, and P. Sonar, New J. Chem., 41, 2899 (2017).

    CAS  Google Scholar 

  29. (29)

    M. Ozdemir, D. Choi, G. Kwon, Y. Zorlu, H. Kim, M.-G. Kim, S. Seo, U. Sen, M. Citir, and C. Kim, RSC Adv., 6, 212 (2016).

    CAS  Google Scholar 

  30. (30)

    T. Hu, L. Han, M. Xiao, X. Bao, T. Wang, M. Sun, and R. Yang, J. Mater. Chem. C, 2, 8047 (2014).

    CAS  Google Scholar 

  31. (31)

    M. R. Reddy, H. Kim, C. Kim, and S. Seo, Synth. Met., 235, 153 (2018).

    CAS  Google Scholar 

  32. (32)

    H. Junichi, O. Hisashi, U. Takayuki, and I. Hiroaki, Tokyo Institute of Technology, JP Patent 2017066089 (2017).

  33. (33)

    L.-F. Lai, C. Qin, C.-H. Chui, A. Islam, L. Han, C.-L. Ho, and W.-Y. Wong, Dyes Pigm., 98, 428 (2013).

    CAS  Google Scholar 

  34. (34)

    M. Durso, M. Zambianchi, A. Zanelli, M. G. LoBello, F. De Angelis, S. Toffanin, S. Cavallini, D. Gentili, F. Tinti, and M. Cavallini, Tetrahedron, 70, 6222 (2014).

    CAS  Google Scholar 

  35. (35)

    S. Zhang, M. U. Ocheje, L. Huang, L. Galuska, Z. Cao, S. Luo, Y. H. Cheng, D. Ehlenberg, R. B. Goodman, and D. Zhou, Adv. Electron. Mater., 5, 1800899 (2019).

    Google Scholar 

  36. (36)

    B. Fu, J. Baltazar, Z. Hu, A.-T. Chien, S. Kumar, C. L. Henderson, D. M. Collard, and E. Reichmanis, Chem. Mater., 24, 4123 (2012).

    CAS  Google Scholar 

  37. (37)

    G. L. Gibson, T. M. McCormick, and D. S. Seferos, J. Am. Chem. Soc., 134, 539 (2012).

    CAS  PubMed  Google Scholar 

  38. (38)

    A. Yassin, P. Leriche, M. Allain, and J. Roncali, New J. Chem., 37, 502 (2013).

    CAS  Google Scholar 

  39. (39)

    A. Gupta, A. Ali, T. B. Singh, A. Bilic, U. Bach, and R. A. Evans, Tetrahedron, 68, 9440 (2012).

    CAS  Google Scholar 

  40. (40)

    F. S. Kim, X. Guo, M. D. Watson, and S. A. Jenekhe, Adv. Mater., 22, 478 (2010).

    CAS  PubMed  Google Scholar 

  41. (41)

    J. Kim, N. Cho, H. M. Ko, C. Kim, J. K. Lee, and J. Ko, Sol. Energy Mater. Sol. Cells, 102, 159 (2012).

    CAS  Google Scholar 

  42. (42)

    M.-C. Chen, Y.-J. Chiang, C. Kim, Y.-J. Guo, S.-Y. Chen, Y.-J. Liang, Y.-W. Huang, T.-S. Hu, G.-H. Lee, and A. Facchetti, Chem. Commun., 1846 (2009).

    Google Scholar 

  43. (43)

    C. Li, X. Du, Y. Zhou, J. Ye, L. Fu, M. G. Humphrey, C. Wu, J. Zhao, Y. Du, and S. Tao, J. Mater. Chem. C, 6, 6949 (2018).

    CAS  Google Scholar 

  44. (44)

    C. Kim, A. Facchetti, and T. J. Marks, Adv. Mater., 19, 2561 (2007).

    CAS  Google Scholar 

  45. (45)

    M. L. Borgne, J. Quinn, J. Martin, N. Stingelin, Y. Li, and G. Wantz, J. Mater. Chem. C, 5, 5143 (2017).

    Google Scholar 

  46. (46)

    K. P. Pernstich, S. Haas, D. Oberhoff, C. Goldmann, D. J. Gundlach, B. Batlogg, A. N. Rashid, G. J. Schitter, Appl. Phys., 96, 6431 (2004).

    CAS  Google Scholar 

  47. (47)

    C. Kim, A. Facchetti, and T. J. Marks, J. Am. Chem. Soc., 131, 9122 (2009).

    CAS  PubMed  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding authors

Correspondence to Choongik Kim or SungYong Seo.

Additional information

Publisher’s Note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Acknowledgment: This work was supported by a Research Grant of Pukyong National University ({dy2019}).

Supporting Information

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Lee, J., Yun, C., Reddy, M.R. et al. Synthesis and Characterization of Fluorenone-Based Donor-Acceptor Small Molecule Organic Semiconductors for Organic Field-Effect Transistors. Macromol. Res. 28, 654–659 (2020). https://doi.org/10.1007/s13233-020-8123-z

Download citation

Keywords

  • organic field effect transistor
  • organic semiconductor
  • fluorenone
  • donor-acceptor