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

  • Gaurav Giri (a1), Eric Miller (a1) and Zhenan Bao (a1)

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.

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Corresponding author

a) Address all correspondence to this author. e-mail: zbao@stanford.edu

References

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1. Klauk, H.: Organic Electronics: Materials, Manufacturing, and Applications (Wiley-VCH, Weinheim, 2006).
2. Forrest, S.R.: The road to high efficiency organic light emitting devices. Org. Electron. 4(2), 45 (2003).
3. Kelley, T.W., Baude, P.F., Gerlach, C., Ender, D.E., Muyres, D., Haase, M.A., Vogel, D.E., and Theiss, S.D.: Recent progress in organic electronics: Materials, devices, and processes. Chem. Mater. 16(23), 4413 (2004).
4. Berggren, M., Nilsson, D., and Robinson, N.D.: Organic materials for printed electronics. Nat. Mater. 6(1), 3 (2007).
5. Malliaras, G. and Friend, R.: An organic electronics primer. Phys. Today 58, 53 (2005).
6. Chua, L-L., Zaumseil, J., Chang, J-F., Ou, E.C-W., Ho, P.K-H., Sirringhaus, H., and Friend, R.H.: General observation of n-type field-effect behaviour in organic semiconductors. Nature 434(7030), 194 (2005).
7. Dimitrakopoulos, C.D. and Malenfant, P.R.L.: Organic thin film transistors for large area electronics. Adv. Mater. 14(2), 99 (2002).
8. Park, S.K., Jackson, T.N., Anthony, J.E., and Mourey, D.A.: High mobility solution processed 6, 13-bis (triisopropyl-silylethynyl) pentacene organic thin film transistors. Appl. Phys. Lett. 91, 063514 (2007).
9. Klauk, H., Halik, M., Zschieschang, U., Schmid, G., Radlik, W., and Weber, W.: High-mobility polymer gate dielectric pentacene thin film transistors. J. Appl. Phys. 92(9), 5259 (2002).
10. Jurchescu, O.D., Baas, J., and Palstra, T.: Effect of impurities on the mobility of single crystal pentacene. Appl. Phys. Lett. 84(16), 3061 (2004).
11. Podzorov, V., Pudalov, V., and Gershenson, M.: Field-effect transistors on rubrene single crystals with parylene gate insulator. Appl. Phys. Lett. 82(11), 1739 (2003).
12. Sokolov, A.N., Atahan-Evrenk, S., Mondal, R., Akkerman, H.B., Sánchez-Carrera, R.S., Granados-Focil, S., Schrier, J., Mannsfeld, S.C., Zoombelt, A.P., Bao, Z., and Aspuru-Guzik, A.: From computational discovery to experimental characterization of a high hole mobility organic crystal. Nat. Commun. 2, 437 (2011).
13. Minemawari, H., Yamada, T., Matsui, H., Tsutsumi, J.Y., Haas, S., Chiba, R., Kumai, R., and Hasegawa, T.: Inkjet printing of single-crystal films. Nature 475(7356), 364 (2011).
14. Izawa, T., Miyazaki, E., and Takimiya, K.: Molecular ordering of high-performance soluble molecular semiconductors and re-evaluation of their field-effect transistor characteristics. Adv. Mater. 20(18), 3388 (2008).
15. Park, J., Lee, S., and Lee, H.H.: High-mobility polymer thin-film transistors fabricated by solvent-assisted drop-casting. Org. Electron. 7(5), 256 (2006).
16. Chang, J-F., Sun, B., Breiby, D.W., Nielsen, M.M., Sölling, T.I., Giles, M., McCulloch, I., and Sirringhaus, H.: Enhanced mobility of poly (3-hexylthiophene) transistors by spin-coating from high-boiling-point solvents. Chem. Mater. 16(23), 4772 (2004).
17. DeLongchamp, D.M., Kline, R.J., Jung, Y., Germack, D.S., Lin, E.K., Moad, A.J., Richter, L.J., Toney, M.F., Heeney, M., and McCulloch, I.: Controlling the orientation of terraced nanoscale “ribbons” of a poly (thiophene) semiconductor. ACS Nano 3(4), 780 (2009).
18. Schilinsky, P., Waldauf, C., and Brabec, C.J.: Performance analysis of printed bulk heterojunction solar cells. Adv. Funct. Mater. 16(13), 1669 (2006).
19. Wengeler, L., Schmidt-Hansberg, B., Peters, K., Scharfer, P., and Schabel, W.: 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).
20. de Gans, B.J., Duineveld, P.C., and Schubert, U.S.: Inkjet printing of polymers: State of the art and future developments. Adv. Mater. 16(3), 203 (2004).
21. Pisula, W., Menon, A., Stepputat, M., Lieberwirth, I., Kolb, U., Tracz, A., Sirringhaus, H., Pakula, T., and Müllen, K.: A zone-casting technique for device fabrication of field-effect transistors based on discotic hexa-peri-hexabenzocoronene. Adv. Mater. 17(6), 684 (2005).
22. Tracz, A., Makowski, T., Masirek, S., Pisula, W., and Geerts, Y.: Macroscopically aligned films of discotic phthalocyanine by zone casting. Nanotechnology 18(48), 485303 (2007).
23. Becerril, H.A., Roberts, M.E., Liu, Z., Locklin, J., and Bao, Z.: High-performance organic thin-film transistors through solution-sheared deposition of small-molecule organic semiconductors. Adv. Mater. 20(13), 2588 (2008).
24. Liu, Z., Becerril, H.A., Roberts, M.E., Nishi, Y., and Bao, Z.: 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).
25. Giri, G., Verploegen, E., Mannsfeld, S.C., Atahan-Evrenk, S., Lee, S.Y., Becerril, H.A., Aspuru-Guzik, A., Toney, M.F., and Bao, Z.: Tuning charge transport in solution-sheared organic semiconductors using lattice strain. Nature 480(7378), 504 (2011).
26. Diao, Y., Tee, B.C.K., Giri, G., Xu, J., Kim, D.H., Becerril, H.A., Stoltenberg, R.M., Lee, T.H., Xue, G., Mannsfeld, S.C.B., and Bao, Z.: Solution coating of large-area organic semiconductor thin films with aligned single-crystalline domains. Nat. Mater. 12(7), 665 (2013).
27. Dickey, K.C., Subramanian, S., Anthony, J.E., Han, L-H., Chen, S., and Loo, Y-L.: 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).
28. Kymissis, I., Dimitrakopoulos, C.D., and Purushothaman, S.: Patterning pentacene organic thin film transistors. J. Vac. Sci. Technol., B: Microelectron. Nanometer Struct. 20(3), 956 (2002).
29. Ling, M.M. and Bao, Z.: Thin film deposition, patterning, and printing in organic thin film transistors. Chem. Mater. 16(23), 4824 (2004).
30. Briseno, A.L., Mannsfeld, S.C.B., Ling, M.M., Liu, S., Tseng, R.J., Reese, C., Roberts, M.E., Yang, Y., Wudl, F., and Bao, Z.: Patterning organic single-crystal transistor arrays. Nature 444(7121), 913 (2006).
31. Mannsfeld, S.C., Sharei, A., Liu, S., Roberts, M.E., McCulloch, I., Heeney, M., and Bao, Z.: Highly efficient patterning of organic single-crystal transistors from the solution phase. Adv. Mater. 20(21), 4044 (2008).
32. Briseno, A.L., Mannsfeld, S.C., Reese, C., Hancock, J.M., Xiong, Y., Jenekhe, S.A., Bao, Z., and Xia, Y.: Perylenediimide nanowires and their use in fabricating field-effect transistors and complementary inverters. Nano Lett. 7(9), 2847 (2007).
33. Oh, J.H., Lee, H.W., Mannsfeld, S., Stoltenberg, R.M., Jung, E., Jin, Y.W., Kim, J.M., Yoo, J-B., and Bao, Z.: Solution-processed, high-performance n-channel organic microwire transistors. Proc. Natl. Acad. Sci. U. S. A. 106(15), 6065 (2009).
34. DeFranco, J.A., Schmidt, B.S., Lipson, M., and Malliaras, G.G.: Photolithographic patterning of organic electronic materials. Org. Electron. 7(1), 22 (2006).
35. Nakayama, K., Hirose, Y., Soeda, J., Yoshizumi, M., Uemura, T., Uno, M., Li, W., Kang, M.J., Yamagishi, M., Okada, Y., Miyazaki, E., Nakazawa, Y., Nakao, A., Takimiya, K., and Takeya, J.: Patternable solution-crystallized organic transistors with high charge carrier mobility. Adv. Mater. 23(14), 1626 (2011).
36. Akkerman, H.B., Chang, A.C., Verploegen, E., Bettinger, C.J., Toney, M.F., and Bao, Z.: Fabrication of organic semiconductor crystalline thin films and crystals from solution by confined crystallization. Org. Electron. 13(2), 235 (2012).
37. Kang, B., Min, H., Seo, U., Lee, J., Park, N., Cho, K., and Lee, H.S.: 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).
38. Jo, P.S., Vailionis, A., Park, Y.M., and Salleo, A.: Scalable fabrication of strongly textured organic semiconductor micropatterns by capillary force lithography. Adv. Mater. 24(24), 3269 (2012).
39. Dickey, K., Anthony, J.E., and Loo, Y-L.: Improving organic thin-film transistor performance through solvent-vapor annealing of solution processable triethylsilylethynyl anthradithiophene. Adv. Mater. 18, 1721 (2006).
40. Goto, O., Tomiya, S., Murakami, Y., Shinozaki, A., Toda, A., Kasahara, J., and Hobara, D.: Organic single-crystal arrays from solution-phase growth using micropattern with nucleation control region. Adv. Mater. 24(8), 1117 (2012).
41. Ward, J.W., Loth, M.A., Kline, R.J., Coll, M., Ocal, C., Anthony, J.E., and Jurchescu, O.D.: Tailored interfaces for self-patterning organic thin-film transistors. J. Mater. Chem. 22(36), 19047 (2012).
42. Minari, T., Liu, C., Kano, M., and Tsukagoshi, K.: Controlled self-assembly of organic semiconductors for solution-based fabrication of organic field-effect transistors. Adv. Mater. 24(2), 299 (2012).
43. Li, Y., Liu, C., Kumatani, A., Darmawan, P., Minari, T., and Tsukagoshi, K.: 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).
44. Li, H., Tee, B.C.K., Giri, G., Chung, J.W., Lee, S.Y., and Bao, Z.: High-performance transistors and complementary inverters based on solution-grown aligned organic single-crystals. Adv. Mater. 24(19), 2588 (2012).
45. Park, S.K., Mourey, D.A., Subramanian, S., Anthony, J.E., and Jackson, T.N.: Non-relief-pattern lithography patterning of solution processed organic semiconductors. Adv. Mater. 20(21), 4145 (2008).
46. Giri, G., Park, S., Vosgueritchian, M., Shulaker, M.M., and Bao, Z.: High-mobility, aligned crystalline domains of TIPS-pentacene with metastable polymorphs through lateral confinement of crystal growth. Adv. Mater. 26(3), 487 (2014).
47. Ito, Y., Virkar, A.A., Mannsfeld, S., Oh, J.H., Toney, M., Locklin, J., and Bao, Z.: Crystalline ultrasmooth self-assembled monolayers of alkylsilanes for organic field-effect transistors. J. Am. Chem. Soc. 131(26), 9396 (2009).
48. Mannsfeld, S.C., Tang, M.L., and Bao, Z.: 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).

Keywords

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

  • Gaurav Giri (a1), Eric Miller (a1) and Zhenan Bao (a1)

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