Skip to main content
Log in

Selective solution shearing deposition of high performance TIPS-pentacene polymorphs through chemical patterning

  • Invited Feature Paper
  • Published:
Journal of Materials Research Aims and scope Submit manuscript

Abstract

Methods for the solution deposition of organic semiconductors (OSCs) show great potential for the production of large-area, inexpensive, and flexible organic electronics. A solution deposition method called solution shearing has consistently been shown to yield thin film transistors with improved performance over those created via other solution-based approaches. However, the need for discrete, electronically isolated devices requires the parallel development of a facile means of pattern definition compatible with the solution shearing process. In our work, we use a simple chemical prepatterning method to enable the solution shearing deposition of the small molecule OSC TIPS-pentacene on substrates with feature sizes as small as 100 µm. Grazing incidence x-ray diffraction (GIXD) was also used to confirm the existence of high performance TIPS-pentacene polymorphs in the patterned thin films. Mobilities as high as 1.13 cm2 V−1 s−1 were obtained on 400 µm wide patterns by depositing a high-performance, metastable polymorph of TIPS-pentacene.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

FIG. 1
FIG. 2
FIG. 3
FIG. 4
FIG. 5

Similar content being viewed by others

References

  1. H. Klauk: Organic Electronics: Materials, Manufacturing, and Applications (Wiley-VCH, Weinheim, 2006).

    Google Scholar 

  2. S.R. Forrest: The road to high efficiency organic light emitting devices. Org. Electron. 4(2), 45 (2003).

    Google Scholar 

  3. T.W. Kelley, P.F. Baude, C. Gerlach, D.E. Ender, D. Muyres, M.A. Haase, D.E. Vogel, and S.D. Theiss: Recent progress in organic electronics: Materials, devices, and processes. Chem. Mater. 16(23), 4413 (2004).

    CAS  Google Scholar 

  4. M. Berggren, D. Nilsson, and N.D. Robinson: Organic materials for printed electronics. Nat. Mater. 6(1), 3 (2007).

    CAS  Google Scholar 

  5. G. Malliaras and R. Friend: An organic electronics primer. Phys. Today 58, 53 (2005).

    CAS  Google Scholar 

  6. L-L. Chua, J. Zaumseil, J-F. Chang, E.C-W. Ou, P.K-H. Ho, H. Sirringhaus, and R.H. Friend: General observation of n-type field-effect behaviour in organic semiconductors. Nature 434(7030), 194 (2005).

    CAS  Google Scholar 

  7. C.D. Dimitrakopoulos and P.R.L. Malenfant: Organic thin film transistors for large area electronics. Adv. Mater. 14(2), 99 (2002).

    CAS  Google Scholar 

  8. S.K. Park, T.N. Jackson, J.E. Anthony, and D.A. Mourey: High mobility solution processed 6, 13-bis (triisopropyl-silylethynyl) pentacene organic thin film transistors. Appl. Phys. Lett. 91, 063514 (2007).

    Google Scholar 

  9. H. Klauk, M. Halik, U. Zschieschang, G. Schmid, W. Radlik, and W. Weber: High-mobility polymer gate dielectric pentacene thin film transistors. J. Appl. Phys. 92(9), 5259 (2002).

    CAS  Google Scholar 

  10. O.D. Jurchescu, J. Baas, and T. Palstra: Effect of impurities on the mobility of single crystal pentacene. Appl. Phys. Lett. 84(16), 3061 (2004).

    CAS  Google Scholar 

  11. V. Podzorov, V. Pudalov, and M. Gershenson: Field-effect transistors on rubrene single crystals with parylene gate insulator. Appl. Phys. Lett. 82(11), 1739 (2003).

    CAS  Google Scholar 

  12. A.N. Sokolov, S. Atahan-Evrenk, R. Mondal, H.B. Akkerman, R.S. Sánchez-Carrera, S. Granados-Focil, J. Schrier, S.C. Mannsfeld, A.P. Zoombelt, Z. Bao, and A. Aspuru-Guzik: From computational discovery to experimental characterization of a high hole mobility organic crystal. Nat. Commun. 2, 437 (2011).

    Google Scholar 

  13. H. Minemawari, T. Yamada, H. Matsui, J.Y. Tsutsumi, S. Haas, R. Chiba, R. Kumai, and T. Hasegawa: Inkjet printing of single-crystal films. Nature 475(7356), 364 (2011).

    CAS  Google Scholar 

  14. T. Izawa, E. Miyazaki, and K. Takimiya: Molecular ordering of high-performance soluble molecular semiconductors and re-evaluation of their field-effect transistor characteristics. Adv. Mater. 20(18), 3388 (2008).

    CAS  Google Scholar 

  15. J. Park, S. Lee, and H.H. Lee: High-mobility polymer thin-film transistors fabricated by solvent-assisted drop-casting. Org. Electron. 7(5), 256 (2006).

    CAS  Google Scholar 

  16. J-F. Chang, B. Sun, D.W. Breiby, M.M. Nielsen, T.I. Sölling, M. Giles, I. McCulloch, and H. Sirringhaus: Enhanced mobility of poly (3-hexylthiophene) transistors by spin-coating from high-boiling-point solvents. Chem. Mater. 16(23), 4772 (2004).

    CAS  Google Scholar 

  17. D.M. DeLongchamp, R.J. Kline, Y. Jung, D.S. Germack, E.K. Lin, A.J. Moad, L.J. Richter, M.F. Toney, M. Heeney, and I. McCulloch: Controlling the orientation of terraced nanoscale “ribbons” of a poly (thiophene) semiconductor. ACS Nano 3(4), 780 (2009).

    CAS  Google Scholar 

  18. P. Schilinsky, C. Waldauf, and C.J. Brabec: Performance analysis of printed bulk heterojunction solar cells. Adv. Funct. Mater. 16(13), 1669 (2006).

    CAS  Google Scholar 

  19. L. Wengeler, B. Schmidt-Hansberg, K. Peters, P. Scharfer, and W. Schabel: Investigations on knife and slot die coating and processing of polymer nanoparticle films for hybrid polymer solar cells. Chem. Eng. Process. 50(5), 478 (2011).

    CAS  Google Scholar 

  20. B.J. de Gans, P.C. Duineveld, and U.S. Schubert: Inkjet printing of polymers: State of the art and future developments. Adv. Mater. 16(3), 203 (2004).

    Google Scholar 

  21. W. Pisula, A. Menon, M. Stepputat, I. Lieberwirth, U. Kolb, A. Tracz, H. Sirringhaus, T. Pakula, and K. Müllen: A zone-casting technique for device fabrication of field-effect transistors based on discotic hexa-peri-hexabenzocoronene. Adv. Mater. 17(6), 684 (2005).

    CAS  Google Scholar 

  22. A. Tracz, T. Makowski, S. Masirek, W. Pisula, and Y. Geerts: Macroscopically aligned films of discotic phthalocyanine by zone casting. Nanotechnology 18(48), 485303 (2007).

    Google Scholar 

  23. H.A. Becerril, M.E. Roberts, Z. Liu, J. Locklin, and Z. Bao: High-performance organic thin-film transistors through solution-sheared deposition of small-molecule organic semiconductors. Adv. Mater. 20(13), 2588 (2008).

    CAS  Google Scholar 

  24. Z. Liu, H.A. Becerril, M.E. Roberts, Y. Nishi, and Z. Bao: Experimental study and statistical analysis of solution-shearing processed organic transistors based on an asymmetric small-molecule semiconductor. IEEE Trans. Electron Devices 56(2), 176 (2009).

    CAS  Google Scholar 

  25. G. Giri, E. Verploegen, S.C. Mannsfeld, S. Atahan-Evrenk, S.Y. Lee, H.A. Becerril, A. Aspuru-Guzik, M.F. Toney, and Z. Bao: Tuning charge transport in solution-sheared organic semiconductors using lattice strain. Nature 480(7378), 504 (2011).

    CAS  Google Scholar 

  26. Y. Diao, B.C.K. Tee, G. Giri, J. Xu, D.H. Kim, H.A. Becerril, R.M. Stoltenberg, T.H. Lee, G. Xue, S.C.B. Mannsfeld, and Z. Bao: Solution coating of large-area organic semiconductor thin films with aligned single-crystalline domains. Nat. Mater. 12(7), 665 (2013).

    CAS  Google Scholar 

  27. K.C. Dickey, S. Subramanian, J.E. Anthony, L-H. Han, S. Chen, and Y-L. Loo: Large-area patterning of a solution-processable organic semiconductor to reduce parasitic leakage and off currents in thin-film transistors. Appl. Phys. Lett. 90(24), 244103 (2007).

    Google Scholar 

  28. I. Kymissis, C.D. Dimitrakopoulos, and S. Purushothaman: Patterning pentacene organic thin film transistors. J. Vac. Sci. Technol., B: Microelectron. Nanometer Struct. 20(3), 956 (2002).

    CAS  Google Scholar 

  29. M.M. Ling and Z. Bao: Thin film deposition, patterning, and printing in organic thin film transistors. Chem. Mater. 16(23), 4824 (2004).

    CAS  Google Scholar 

  30. A.L. Briseno, S.C.B. Mannsfeld, M.M. Ling, S. Liu, R.J. Tseng, C. Reese, M.E. Roberts, Y. Yang, F. Wudl, and Z. Bao: Patterning organic single-crystal transistor arrays. Nature 444(7121), 913 (2006).

    CAS  Google Scholar 

  31. S.C. Mannsfeld, A. Sharei, S. Liu, M.E. Roberts, I. McCulloch, M. Heeney, and Z. Bao: Highly efficient patterning of organic single-crystal transistors from the solution phase. Adv. Mater. 20(21), 4044 (2008).

    CAS  Google Scholar 

  32. A.L. Briseno, S.C. Mannsfeld, C. Reese, J.M. Hancock, Y. Xiong, S.A. Jenekhe, Z. Bao, and Y. Xia: Perylenediimide nanowires and their use in fabricating field-effect transistors and complementary inverters. Nano Lett. 7(9), 2847 (2007).

    CAS  Google Scholar 

  33. J.H. Oh, H.W. Lee, S. Mannsfeld, R.M. Stoltenberg, E. Jung, Y.W. Jin, J.M. Kim, J-B. Yoo, and Z. Bao: Solution-processed, high-performance n-channel organic microwire transistors. Proc. Natl. Acad. Sci. U. S. A. 106(15), 6065 (2009).

    CAS  Google Scholar 

  34. J.A. DeFranco, B.S. Schmidt, M. Lipson, and G.G. Malliaras: Photolithographic patterning of organic electronic materials. Org. Electron. 7(1), 22 (2006).

    CAS  Google Scholar 

  35. K. Nakayama, Y. Hirose, J. Soeda, M. Yoshizumi, T. Uemura, M. Uno, W. Li, M.J. Kang, M. Yamagishi, Y. Okada, E. Miyazaki, Y. Nakazawa, A. Nakao, K. Takimiya, and J. Takeya: Patternable solution-crystallized organic transistors with high charge carrier mobility. Adv. Mater. 23(14), 1626 (2011).

    CAS  Google Scholar 

  36. H.B. Akkerman, A.C. Chang, E. Verploegen, C.J. Bettinger, M.F. Toney, and Z. Bao: Fabrication of organic semiconductor crystalline thin films and crystals from solution by confined crystallization. Org. Electron. 13(2), 235 (2012).

    CAS  Google Scholar 

  37. B. Kang, H. Min, U. Seo, J. Lee, N. Park, K. Cho, and H.S. Lee: Directly drawn organic transistors by capillary pen: A new facile patterning method using capillary action for soluble organic materials. Adv. Mater. 25(30), 4117 (2013).

    CAS  Google Scholar 

  38. P.S. Jo, A. Vailionis, Y.M. Park, and A. Salleo: Scalable fabrication of strongly textured organic semiconductor micropatterns by capillary force lithography. Adv. Mater. 24(24), 3269 (2012).

    CAS  Google Scholar 

  39. K. Dickey, J.E. Anthony, and Y-L. Loo: Improving organic thin-film transistor performance through solvent-vapor annealing of solution processable triethylsilylethynyl anthradithiophene. Adv. Mater. 18, 1721 (2006).

    CAS  Google Scholar 

  40. O. Goto, S. Tomiya, Y. Murakami, A. Shinozaki, A. Toda, J. Kasahara, and D. Hobara: Organic single-crystal arrays from solution-phase growth using micropattern with nucleation control region. Adv. Mater. 24(8), 1117 (2012).

    CAS  Google Scholar 

  41. J.W. Ward, M.A. Loth, R.J. Kline, M. Coll, C. Ocal, J.E. Anthony, and O.D. Jurchescu: Tailored interfaces for self-patterning organic thin-film transistors. J. Mater. Chem. 22(36), 19047 (2012).

    CAS  Google Scholar 

  42. T. Minari, C. Liu, M. Kano, and K. Tsukagoshi: Controlled self-assembly of organic semiconductors for solution-based fabrication of organic field-effect transistors. Adv. Mater. 24(2), 299 (2012).

    CAS  Google Scholar 

  43. Y. Li, C. Liu, A. Kumatani, P. Darmawan, T. Minari, and K. Tsukagoshi: Large plate-like organic crystals from direct spin-coating for solution-processed field-effect transistor arrays with high uniformity. Org. Electron. 13(2), 264 (2012).

    CAS  Google Scholar 

  44. H. Li, B.C.K. Tee, G. Giri, J.W. Chung, S.Y. Lee, and Z. Bao: High-performance transistors and complementary inverters based on solution-grown aligned organic single-crystals. Adv. Mater. 24(19), 2588 (2012).

    CAS  Google Scholar 

  45. S.K. Park, D.A. Mourey, S. Subramanian, J.E. Anthony, and T.N. Jackson: Non-relief-pattern lithography patterning of solution processed organic semiconductors. Adv. Mater. 20(21), 4145 (2008).

    CAS  Google Scholar 

  46. G. Giri, S. Park, M. Vosgueritchian, M.M. Shulaker, and Z. Bao: High-mobility, aligned crystalline domains of TIPS-pentacene with metastable polymorphs through lateral confinement of crystal growth. Adv. Mater. 26(3), 487 (2014).

    CAS  Google Scholar 

  47. Y. Ito, A.A. Virkar, S. Mannsfeld, J.H. Oh, M. Toney, J. Locklin, and Z. Bao: Crystalline ultrasmooth self-assembled monolayers of alkylsilanes for organic field-effect transistors. J. Am. Chem. Soc. 131(26), 9396 (2009).

    CAS  Google Scholar 

  48. S.C. Mannsfeld, M.L. Tang, and Z. Bao: Thin film structure of triisopropylsilylethynyl-functionalized pentacene and tetraceno [2, 3-b] thiophene from grazing incidence x-ray diffraction. Adv. Mater. 23(1), 127 (2011).

    CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

This publication was partially supported by the National Science Foundation (DMR-1006989, DMR-1059020, and DMR-1303178), the Air Force Office of Scientific Research (FA9550-12-1-0190), and the Global Climate and Energy Project at Stanford University. Z.B. acknowledges support from the David Filo and Jerry Yang Faculty Fellowship from Stanford University. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource, a national user facility operated by Stanford University on behalf of the US Department of Energy, Office of Basic Energy Sciences. Any opinions, findings, and conclusions or recommendations expressed in this publication are those of the authors and do not necessarily reflect the views of Stanford University, the Sponsors of the Global Climate and Energy Project, or others involved with the Global Climate and Energy Project.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zhenan Bao.

Additional information

Equal authorship.

This paper has been selected as an Invited Feature Paper.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Giri, G., Miller, E. & Bao, Z. Selective solution shearing deposition of high performance TIPS-pentacene polymorphs through chemical patterning. Journal of Materials Research 29, 2615–2624 (2014). https://doi.org/10.1557/jmr.2014.305

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1557/jmr.2014.305

Navigation