5 P. M. S. Monk, R. J. Mortimer and D. R. Rosseinsky,
Electrochromism and Electrochromic Devices, Cambridge University
Press, Cambridge, 2007.
6 J. Roncali, Chem. Rev., 1997, 97, 173.
7 M. Mas-Torrent, P. Hadley, S. T. Bromley, X. Ribas, J. Tarres,
ꢀ
M. Mas, E. Molins, J. Veciana and C. Rovira, J. Am. Chem. Soc.,
2004, 126, 8546.
8 V. C. Sundar, J. Zaumseil, V. Podzorov, E. Menard, R. L. Willett,
T.Someya, M. E.GershensonandJ. A.Rogers,Science, 2004, 303, 1644.
9 H. Klauk, M. Halik, U. Zschieschang, F. Eder, G. Schmid and
C. Dehm, Appl. Phys. Lett., 2003, 82, 4175.
10 B. A. Jones, A. Facchetti, M. R. Wasielewski and T. J. Marks, Adv.
Funct. Mater., 2008, 18, 1329.
11 K. Takimiya, S. Shinamura, I. Osaka and E. Miyazaki, Adv. Mater.,
2011, 23, 4347.
12 W. Wu, Y. Liu and D. Zhu, Chem. Soc. Rev., 2010, 39, 1489.
13 M. Mas-Torrent and C. Rovira, J. Mater. Chem., 2006, 16, 433.
14 M. Mas-Torrent and C. Rovira, Chem. Soc. Rev., 2008, 37, 827.
15 H. Bronstein, Z. Chen, R. S. Ashraf, W. Zhang, J. Du, J. R. Durrant,
P. Shakya Tuladhar, K. Song, S. E. Watkins, Y. Geerts,
M. M. Wienk, R. A. J. Janssen, T. Anthopoulos, H. Sirringhaus,
M. Heeney and I. McCulloch, J. Am. Chem. Soc., 2011, 133, 3272.
16 I. McCulloch, M. Heeney, C. Bailey, K. Genevicius, I. MacDonald,
M. Shkunov, D. Sparrowe, S. Tierney, R. Wagner, W. Zhang,
M. L. Chabinyc, R. J. Kline, M. D. McGehee and M. F. Toney,
Nat. Mater., 2006, 5, 328.
Fig. 6 Tapping mode AFM height images of p(DPP-TTF) on OTS
treated SiO2 surfaces after annealing at 200 ꢀC for 20 min.
that do not contain the TTF unit but have thiophene units
(highest mobility of ꢄ1 cm2 Vꢃ1 sꢃ1).20–23 Further optimisation of
processing conditions for device fabrication such as the spinning
process, solution concentration, and OTS treatment of SiO2
substrates might produce higher mobilities similar to other DPP-
containing polymers. These device characteristics are highly
reproducible under ambient laboratory conditions as shown in
Fig. 5 (bottom). The stability of these devices under ambient
atmospheric conditions has been attributed to the aforemen-
tioned partial charge transfer interactions between the TTF and
DPP units in p(DPP-TTF), which define a stable morphology
and propensity of the materials to withstand the effects of an
ambient environment. Moreover, the stability of the TTF unit
towards oxidation is extremely well known.
17 H. Yan, Z. Chen, Y. Zheng, C. Newman, J. R. Quinn, F. Dotz,
M. Kastler and A. Facchetti, Nature, 2009, 457, 679.
18 M. Zhang, H. N. Tsao, W. Pisula, C. Yang, A. K. Mishra and
€
K. Mullen, J. Am. Chem. Soc., 2007, 129, 3472.
€
19 L. Burgi, M. Turbiez, R. Pfeiffer, F. Bienewald, H.-J. Kirner and
C. Winnewisser, Adv. Mater., 2008, 20, 2217.
20 J. C. Bijleveld, A. P. Zoombelt, S. G. J. Mathijssen, M. M. Wienk,
M. Turbiez, D. M. de Leeuw and R. A. J. Janssen, J. Am. Chem.
Soc., 2009, 131, 16616.
21 S. Cho, J. Lee, M. Tong, J. H. Seo and C. Yang, Adv. Funct. Mater.,
2011, 21, 1910.
22 Y. Li, S. P. Singh and P. Sonar, Adv. Mater., 2010, 22, 4862.
23 P. Sonar, S. P. Singh, Y. Li, M. S. Soh and A. Dodabalapur, Adv.
Mater., 2010, 22, 5409.
24 M. R. Bryce, A. Chissel, J. Gopal, P. Kathirgamanathan and
D. Parker, Synth. Met., 1991, 39, 397.
25 L. Huchet, S. Akoudad, E. Levillain, J. Roncali, A. Emge and
€
P. Bauerle, J. Phys. Chem. B, 1998, 102, 7776.
26 L. Huchet, S. Akoudad and J. Roncali, Adv. Mater., 1998, 10, 541.
27 H. Muller, F. Salhi, B. Divisia-Blohorn, F. Genoud, T. Narayanan,
M. Lorenzen and C. Ferrero, Chem. Commun., 1999, 1407.
28 C. Thobie-Gautier, A. Gorgues, M. Jubault and J. Roncali,
Macromolecules, 1993, 26, 4094.
29 R. Berridge, P. J. Skabara, C. Pozo-Gonzalo, A. Kanibolotsky,
J. Lohr, J. J. W. McDouall, E. J. L. McInnes, J. Wolowska,
C. Winder, N. S. Sariciftci, R. W. Harrington and W. Clegg, J.
Phys. Chem. B, 2006, 110, 3140.
Summary
We have reported the synthesis, properties and device character-
istics of p(DPP-TTF), an air stable and solution processable
polymer containing TTF and DPP units within the conjugated
chain, that exhibits a field effect mobility of ꢄ4 ꢂ 10ꢃ2 cm2 Vꢃ1 sꢃ1
and an on/off ratio of ꢄ104. Air stability is due to the presence of
TTF–DPP interactions in the bulk of the solid film and the
inherent stabilisation of the TTF structure towards p-doping.
Additionally, uniform wettability (even on OTS treated SiO2)
over 2 cm ꢂ 2 cm substrates by spin-coating means that this
polymer can be efficiently used in any solution processing
methods such as inkjet printing, spin-coating or roll-to-roll pro-
cessing for organic device applications.
30 P. J. Skabara, R. Berridge, E. J. L. McInnes, D. P. West, S. J. Coles,
€
M. B. Hursthouse and K. Mullen, J. Mater. Chem., 2004, 14, 1964.
€
31 P. J. Skabara and K. Mullen, Synth. Met., 1997, 84, 345.
32 P. J. Skabara, K. Mullen, M. R. Bryce, J. A. K. Howard and
€
A. S. Batsanov, J. Mater. Chem., 1998, 8, 1719.
33 K. Bechgaard, K. Carneiro, F. B. Rasmussen, M. Olsen, G. Rindorf,
C. S. Jacobsen, H. J. Pedersen and J. C. Scott, J. Am. Chem. Soc.,
1981, 103, 2440.
34 F. Wudl, G. M. Smith and E. J. Hufnagel, J. Chem. Soc. D, 1970, 1453.
35 J. P. Bourgoin, M. Vandevyver, A. Barraud, G. Tremblay and
P. Hesto, Mol. Eng., 1993, 2, 309.
36 T. Konoike, K. Namba, T. Shinada, K. Sakaguchi,
G. C. Papavassiliou, K. Murata and Y. Ohfune, Synlett, 2001, 1476.
37 G. Steimecke, H. J. Sieler, R. Kirmse and E. Hoyer, Phosphorus,
Sulfur Silicon Relat. Elem., 1979, 7, 49.
References
1 C. K. Chiang, M. A. Druy, S. C. Gau, A. J. Heeger, E. J. Louis,
A. G. Macdiarmid, Y. W. Park and H. Shirakawa, J. Am. Chem.
Soc., 1978, 100, 1013.
2 C. W. Tang, Appl. Phys. Lett., 1986, 48, 183.
3 A. Tsumura, H. Koezuka and T. Ando, Appl. Phys. Lett., 1986, 49,
1210.
4 J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks,
K. Mackay, R. H. Friend, P. L. Burns and A. B. Holmes, Nature,
1990, 347, 539.
38 N. Svenstrup and J. Becher, Synthesis, 1995, 215.
€
Org. Chem., 2011, 76, 2426.
€
€
39 H. Burckstummer, A. Weissenstein, D. Bialas and F. Wurthner, J.
40 C. R. Mason, P. J. Skabara, D. Cupertino, J. Schofield, F. Meghdadi,
B. Ebner and N. S. Sariciftci, J. Mater. Chem., 2005, 15, 1446.
41 I. H. Campbell, T. W. Hagler, D. L. Smith and J. P. Ferraris, Phys.
Rev. Lett., 1996, 76, 1900.
This journal is ª The Royal Society of Chemistry 2012
J. Mater. Chem., 2012, 22, 11310–11315 | 11315