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Tuning Organic Electronics via Photoreactive Thin Organic Films

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Small Organic Molecules on Surfaces

Part of the book series: Springer Series in Materials Science ((SSMATERIALS,volume 173))

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Abstract

The present chapter deals with photoreactive thin films and describes processes to tune both surface and material properties by means of UV-irradiation. Selected applications of these materials as UV tunable interfaces in organic electronics are demonstrated. Two examples of photoreactive polymers together with the underlying photochemistry are presented. Polymers bearing aryl ester groups or N-arylamide units in their side-chain undergo the photo-Fries reaction under UV-light which yields hydroxyketone and aminoketone units as photoproducts, respectively. The reaction results in a change in surface polarity, which is accompanied by a significant increase in refractive index (Δn up to +0.10). Another example is given with polymers bearing ortho-nitrobenzyl ester units in their side chain. UV-irradiation causes the scission of the ester unit and the formation of polar carboxylic acids. Employing these photosensitive polymers as interfacial layers between the organic semiconductor and the gate dielectric, the characteristics of OTFTs such as carrier mobility and threshold voltage can be varied over a wide range. Moreover, the epitaxial growth of organic semiconductors (para-sexiphenyl and pentacene) on these surfaces can be influenced by photochemical adjustment of surface polarity. Proceeding from thin polymer layers to molecular layers, several examples for photoreactive mono- and oligolayers on metals and oxidic surfaces are presented. These layers, containing aryl ester units for example, were modified by UV illumination and post-exposure derivatization. Lithographic patterns in molecular layers were characterized with friction force microscopy.

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References

  1. G.J. Leggett, Chem. Soc. Rev. 35, 1150–1161 (2006)

    Article  CAS  Google Scholar 

  2. S. Sun, G.J. Leggett, Nano Lett. 7, 3753–3758 (2007)

    Article  CAS  Google Scholar 

  3. P. Ribič, V. Kalihari, C. Frisbie, G. Bratina, Phys. Rev. B 80, 115307 (2009)

    Article  Google Scholar 

  4. G. Hernandez-Sosa, C. Simbrunner, T. Höfler, A. Moser, O. Werzer, B. Kunert, G. Trimmel, W. Kern, R. Resel, H. Sitter, Org. Electron. 10, 326–332 (2009)

    Article  CAS  Google Scholar 

  5. M. Marchl, M. Edler, A. Haase, A. Fian, G. Trimmel, T. Griesser, E. Zojer, B. Stadlober, Adv. Mater. 22, 5361–5365 (2010)

    Article  CAS  Google Scholar 

  6. K. Fries, G. Finck, Chem. Ber. 41, 4271–4284 (1908)

    Article  CAS  Google Scholar 

  7. J.C. Anderson, C.B. Reese, Proc. Chem. Soc. (1960), p. 217

    Google Scholar 

  8. C.E. Kalmus, D.M. Hercules, J. Am. Chem. Soc. 96, 449–456 (1974)

    Article  CAS  Google Scholar 

  9. S. Lochbrunner, M. Zissler, J. Piel, E. Riedle, A. Spiegel, T. Bach, J. Chem. Phys. 120, 11634 (2004)

    Article  CAS  Google Scholar 

  10. H. Barzynski, D. Sänger, Angew. Makromol. Chem. 93, 131–141 (1981)

    Article  CAS  Google Scholar 

  11. G. Ciamician, P. Silber, Chem. Ber. 34, 2040–2046 (1901)

    Article  CAS  Google Scholar 

  12. J.A. Barltrop, P.J. Plant, P. Schofield, Chem. Commun. (London) 822 (1966)

    Google Scholar 

  13. C.H. Bamford, R.G.W. Norrish, J. Mater. Chem. 1504–1511 (1934)

    Google Scholar 

  14. C.G. Bochet, J. Chem. Soc., Perkin Trans. 1, 125–142 (2002)

    Google Scholar 

  15. T. Griesser, A. Wolfberger, M. Edler, M. Belzik, G. Jakopic, G. Trimmel, W. Kern, J. Polym. Sci., Part A, Polym. Chem. 48, 3507–3514 (2010)

    Article  CAS  Google Scholar 

  16. T. Köpplmayr, M. Cardinale, G. Jakopic, G. Trimmel, W. Kern, T. Griesser, J. Mater. Chem. 21, 2965 (2011)

    Article  Google Scholar 

  17. T. Griesser, T. Höfler, G. Jakopic, M. Belzik, W. Kern, G. Trimmel, J. Math. Chem. 19, 4557–4565 (2009)

    Article  CAS  Google Scholar 

  18. T. Höfler, T. Grießer, M. Gruber, G. Jakopic, G. Trimmel, W. Kern, Macromol. Chem. Phys. 209, 488–498 (2008)

    Article  Google Scholar 

  19. T. Griesser, T. Höfler, S. Temmel, W. Kern, G. Trimmel, Chem. Mater. 19, 3011–3017 (2007)

    Article  CAS  Google Scholar 

  20. T. Höfler, T. Grießer, X. Gstrein, G. Trimmel, G. Jakopic, W. Kern, Polymer 48, 1930–1939 (2007)

    Article  Google Scholar 

  21. T. Griesser, J. Kuhlmann, M. Wieser, W. Kern, G. Trimmel, Macromolecules 42, 725–731 (2009)

    Article  CAS  Google Scholar 

  22. H.G. Unger, Planar Optical Waveguides and Fibres (Clarendon, Oxford, 1993)

    Google Scholar 

  23. R.A. Lessard, R. Changkakoti, G. Manivannan, Processes in Photoreactive Polymers (New York, 1995), pp. 305–367

    Google Scholar 

  24. T.D. Milster, Y. Zhang, Mater. Res. Soc. Bull. 31, 318–323 (2006)

    Article  CAS  Google Scholar 

  25. R.S. Moshrefzadeh, D.K. Misemer, M.D. Radcliffe, C.V. Francis, S.K. Mohapatra, Appl. Phys. Lett. 62, 16 (1993)

    Article  CAS  Google Scholar 

  26. A. Natansohn, P. Rochon, C. Barrett, A. Hay, Chem. Mater. 7, 1612–1615 (1995)

    Article  CAS  Google Scholar 

  27. H.J. Coufal, D. Psaltis, G.T. Sincerbox, A.M. Glass, M.J. Cardillo, Springer Ser. Opt. Sci., vol. 76 (2000)

    Google Scholar 

  28. I. Assaid, D. Bosc, I. Hardy, J. Phys. Chem. B 108, 2801–2806 (2004)

    Article  CAS  Google Scholar 

  29. M. Shirai, W. Ma, M. Tsunooka, Eur. Polym. J. 29, 913–918 (1993)

    Article  CAS  Google Scholar 

  30. D. Stifter, H. Sitter, Appl. Phys. Lett. 66, 679 (1995)

    Article  CAS  Google Scholar 

  31. A. Andreev, G. Matt, C.J. Brabec, H. Sitter, D. Badt, H. Seyringer, N.S. Sariciftci, Adv. Mater. 12, 629–633 (2000)

    Article  CAS  Google Scholar 

  32. A. Tsumura, H. Koezuka, T. Ando, Appl. Phys. Lett. 49, 1210 (1986)

    Article  CAS  Google Scholar 

  33. T. Someya, T. Sekitani, S. Iba, Y. Kato, H. Kawaguchi, T. Sakurai, Proc. Natl. Acad. Sci. USA 101, 9966–9970 (2004)

    Article  CAS  Google Scholar 

  34. B. Crone, A. Dodabalapur, Y.Y. Lin, R.W. Filas, Z. Bao, A. LaDuca, R. Sarpeshkar, H.E. Katz, W. Li, Nature 403, 521–523 (2000)

    Article  CAS  Google Scholar 

  35. S. Kobayashi, T. Nishikawa, T. Takenobu, S. Mori, T. Shimoda, T. Mitani, H. Shimotani, N. Yoshimoto, S. Ogawa, Y. Iwasa, Nat. Mater. 3, 317–322 (2004)

    Article  CAS  Google Scholar 

  36. A. Salleo, M.L. Chabinyc, M.S. Yang, R.A. Street, Appl. Phys. Lett. 81, 4383 (2002)

    Article  CAS  Google Scholar 

  37. B.H. Hamadani, D.A. Corley, J.W. Ciszek, J.M. Tour, D. Natelson, Nano Lett. 6, 1303–1306 (2006)

    Article  CAS  Google Scholar 

  38. L.L. Chua, J. Zaumseil, J.F. Chang, E.C.W. Ou, P.K.H. Ho, H. Sirringhaus, R.H. Friend, Nature 434, 194–199 (2005)

    Article  CAS  Google Scholar 

  39. H. Klauk, U. Zschieschang, J. Pflaum, M. Halik, Nature 445, 745–748 (2007)

    Article  CAS  Google Scholar 

  40. C. Huang, H.E. Katz, J.E. West, Langmuir 23, 13223–13231 (2007)

    Article  CAS  Google Scholar 

  41. G. Horowitz, Adv. Mater. 10, 365–377 (1998)

    Article  CAS  Google Scholar 

  42. M. Marchl, A.W. Golubkov, M. Edler, T. Griesser, P. Pacher, A. Haase, B. Stadlober, M.R. Belegratis, G. Trimmel, E. Zojer, Appl. Phys. Lett. 96, 213303 (2010)

    Article  Google Scholar 

  43. Di Carlo, F. Piacenza, A. Bolognesi, B. Stadlober, H. Maresch, Appl. Phys. Lett. 86, 263501 (2005)

    Article  Google Scholar 

  44. S.D. Wang, T. Miyadera, T. Minari, Y. Aoyagi, K. Tsukagoshi, Appl. Phys. Lett. 93, 043311 (2008)

    Article  Google Scholar 

  45. A. Wang, I. Kymissis, V. Bulović, A.I. Akinwande, in Electron Devices Meeting, (IEEE Press, New York, 2004), pp. 381–384

    Google Scholar 

  46. A. Wang, I. Kymissis, V. Bulović, A.I. Akinwande, Appl. Phys. Lett. 89, 112109 (2006)

    Article  Google Scholar 

  47. H. Sakai, K. Konno, H. Murata, Appl. Phys. Lett. 94, 073304 (2009)

    Article  Google Scholar 

  48. P. Pacher, A. Lex, V. Proschek, H. Etschmaier, E. Tchernychova, M. Sezen, U. Scherf, W. Grogger, G. Trimmel, C. Slugovc, E. Zojer, Adv. Mater. 20, 3143–3148 (2008)

    Article  CAS  Google Scholar 

  49. S.K. Possanner, K. Zojer, P. Pacher, E. Zojer, F. Schürrer, Adv. Funct. Mater. 19, 958–967 (2009)

    Article  CAS  Google Scholar 

  50. K. Müllen, U. Scherf, Organic Light Emitting Devices (Wiley/VCH, Weinheim, 2005)

    Book  Google Scholar 

  51. E.J. Cho, F.V. Bright, Anal. Chem. 73, 3289–3293 (2001)

    Article  CAS  Google Scholar 

  52. Z. Chen, Z. Zhang, T. Zhao, F. Bai, Y. Zhang, Z. Wang, Spectrochim. Acta, Part A, Mol. Biomol. Spectrosc. 57, 419–422 (2001)

    Article  CAS  Google Scholar 

  53. T. Griesser, T. Rath, H. Stecher, R. Saf, W. Kern, G. Trimmel, Chem. Mon. 138, 269–276 (2007)

    Article  CAS  Google Scholar 

  54. G. Weiquiang, D.J. Abdallah, R.G. Weiss, J. Photochem. Photobiol. A, Chem. 139, 79–87 (2001)

    Article  Google Scholar 

  55. M. Montague, R.E. Ducker, K.S.L. Chong, R.J. Manning, F.J.M. Rutten, M.C. Davies, G.J. Leggett, Langmuir 23, 7328–7337 (2007)

    Article  CAS  Google Scholar 

  56. S. Flink, F.C.J.M. van Veggel, D.N. Reinhoudt, J. Phys. Org. Chem. 14, 407–415 (2001)

    Article  CAS  Google Scholar 

  57. T. Höfler, A.M. Track, P. Pacher, Q. Shen, H.G. Flesch, G. Hlawacek, G. Koller, M.G. Ramsey, R. Schennach, R. Resel, Mater. Chem. Phys. 119, 287–293 (2010)

    Article  Google Scholar 

  58. T. Griesser, J. Adams, J. Wappel, W. Kern, G.J. Leggett, G. Trimmel, Langmuir 24, 12420–12425 (2008)

    Article  CAS  Google Scholar 

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Correspondence to Matthias Edler .

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Edler, M., Griesser, T., Trimmel, G., Kern, W. (2013). Tuning Organic Electronics via Photoreactive Thin Organic Films. In: Sitter, H., Draxl, C., Ramsey, M. (eds) Small Organic Molecules on Surfaces. Springer Series in Materials Science, vol 173. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-33848-9_6

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