Solid-state organization and ambipolar field-effect transistors of benzothiadiazole-cyclopentadithiophene copolymer with long branched alkyl side chains

Polymers

Volumn 5, Issue 2, 2013, Pages 833-846

  Pisula, Wojciech ^a   Tsao, Hoi Nok ^a   Dudenko, Dmytro ^a   Cho, Don M ^a   Puniredd, Sreenivasa Reddy ^a   Zhao, Yanfei ^a   Mavrinskiy, Alexey ^a   Shu, Jie ^a   Hansen, Michael Ryan ^a   Baumgarten, Martin ^a   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Ambipolar field effect transistor; Donor acceptor polymer; Organic electronics; Self assembly; Solution processing

Indexed keywords

AMBIPOLAR BEHAVIOR; DONOR-ACCEPTOR POLYMERS; ELECTRONIC BEHAVIORS; ORGANIC ELECTRONICS; SOLUTION-PROCESSED; SOLUTION-PROCESSING; STACKING DISTANCES; STERICALLY DEMANDING;

COPOLYMERS; CRYSTAL MICROSTRUCTURE; ELECTRONIC PROPERTIES; FIELD EFFECT TRANSISTORS; SELF ASSEMBLY;

CHAINS;

EID: 84883281452     PISSN: None     EISSN: 20734360     Source Type: Journal    
DOI: 10.3390/polym5020833     Document Type: Article

References (41)

1. Allard, S.; Forster, M.; Souharce, B.; Thiem, H.; Scherf, U. Organic semiconductors for solution-processable field-effect transistors (OFETs). Angew. Chem. Int. Ed. 2008, 47, 4070-4098.
2. Sekitani, T.; Zschieschang, U.; Klauk, H.; Someya, T. Flexible organic transistors and circuits with extreme bending stability. Nat. Mater. 2010, 9, 1015-1022.
3. Chen, H.; Guo, Y.; Yu, G.; Zhao, Y.; Zhang, J.; Gao, D.; Liu, H.; Liu, Y. Highly π-extended copolymers with diketopyrrolopyrrole moieties for high-performance field-effect transistors. Adv. Mater. 2012, 24, 4618-4622.
4. Lei, T.; Dou, J.-H.; Pei, J. Influence of alkyl chain branching positions on the hole mobilities of polymer thin-film transistors. Adv. Mater. 2012, 24, 6457-6461.
5. Chen, Z.; Lee, M.J.; Ashraf, R.S.; Gu, Y.; Albert-Seifried, S.; Nielsen, M.M.; Schroeder, B.; Anthopoulos, T.D.; Heeney, M.; McCulloch, I.; et al. High-performance ambipolar diketopyrrolopyrrole-thieno[3,2-b]thiophene copolymer field-effect transistors with balanced hole and electron mobilities. Adv. Mater. 2012, 24, 647-652.
6. Fan, J.; Yuen, J.D.; Wang, M.; Seifter, J.; Seo, J.-H.; Mohebbi, A.R.; Zakhidov, D.; Heeger, A.; Wudl, F. High-performance ambipolar transistors and inverters from an ultralow bandgap polymer. Adv. Mater. 2012, 24, 2186-2190.
7. Puniredd, S.R.; Kiersnowski, A.; Battagliarin, G.; Zajaczkowski, W.; Wong, W.W.H.; Kirby, N.; Müllen, K.; Pisula, W. Polythiophene-Perylene diimide heterojunction field-effect transistors. J. Mater. Chem. C 2013, 1, 2433-2440.
8. Chua, L.-L.; Zaumseil, J.; Chang, J.-F.; Ou, E.C.W.; Ho, P.K.H.; Sirringhaus H.; Friend, R.H. General observation of n-type field-effect behaviour in organic semiconductors. Nature 2005, 434, 194-199.
9. Meijer, E.J.; de Leeuw, D.M.; Setayesh, S.; van Veenendaal, E.; Huisman, B.-H.; Blom, P.W.M.; Hummelen, J.C.; Scherf, U.; Klapwijk T.M. Solution-processed ambipolar organic field-effect transistors and inverters. Nat. Mater. 2003, 2, 678-682.
10. Tsao, H.N.; Pisula, W.; Liu, Z.; Osikowicz, W.; Salaneck, W.R.; Müllen, K. Unipolar behavior in discotic dye field-effect transistors. Adv. Mater. 2008, 20, 2715-2719.
11. Ribierre, J.-C.; Watanabe, S.; Matsumoto, M.; Muto, T.; Nakao, A.; Aoyama, T. Reversible conversion of the majority carrier type in solution-processed ambipolar quinoidal oligothiophene thin films. Adv. Mater. 2010, 22, 4044-4048.
12. 2/Vs hole mobility in thin-film transistors. J. Am. Chem. Soc. 2011, 133, 10364-10367.
13. Tsao, H.N.; Cho, D.M.; Park, I.; Hansen, M.R.; Mavrinskiy, A.; Yoon, D.Y.; Graf, R.; Pisula, W.; Spiess, H.W.; Müllen, K. Ultrahigh mobility in polymer field-effect transistors by design. J. Am. Chem. Soc. 2011, 133, 2605-2612.
14. Wang, S.; Kappl, M.; Liebewirth, I.; Müller, M.; Kirchhoff, K.; Pisula, W.; Müllen, K. Organic field-effect transistors based on highly ordered single polymer fibers. Adv. Mater. 2012, 24, 417-420.
15. Pisula, W.; Tomovic, Z.; Simpson, C.; Kastler, M.; Pakula, T.; Müllen, K. Relationship between core size, side chain length, and the supramolecular organization of polycyclic aromatic hydrocarbons. Chem. Mater. 2005, 17, 4296-4303.
16. Feike, M.; Demco, D.E.; Graf, R.; Gottwald, J.; Hafner, S.; Spiess, H.W. Broadband multiple-quantum NMR spectroscopy. J. Magn. Resonance Ser. A 1996, 122, 214-221.
17. Van Rossum, B.J.; Forster, H.; de Groot, H.J.M. High-field and high-speed CP-MAS C-13 NMR heteronuclear dipolar-correlation spectroscopy of solids with frequency-switched Lee-Goldburg homonuclear decoupling. J. Magn. Reson. 1997, 124, 516-519.
18. Bielecki, A.; Kolbert, A.C.; Levitt, M.H. Frequency-switched pulse sequences: Homonuclear decoupling and dilute spin NMR in solids. Chem. Phys. Lett. 1989, 155, 341-346.
19. Fung, B.; Khitrin, A.; Ermolaev, K. An improved broadband decoupling sequence for liquid crystals and solids. J. Magn. Reson. 2000, 142, 97-101.
20. Lee, M.; Goldburg, W.I. Nuclear-magnetic-resonance line narrowing by a rotating rf field. Phys. Rev. 1965, 140, 1261-1271.
21. Ladizhansky, V.; Vega, S. Polarization transfer dynamics in Lee-Goldburg cross polarization nuclear magnetic resonance experiments on rotating solids. J. Chem. Phys. 2000, 112, 7158-7168.
22. Morcombe, C.R.; Zilm, K.W. Chemical shift referencing in MAS solid state NMR. J. Magn. Reson. 2003, 162, 479-486.
23. Hayashi, S.; Hayamizu, K. Chemical-shift standards in high-resolution solid-state NMR. 1. Carbon-13, silicon-29 and proton nuclei. Bull. Chem. Soc. Jpn. 1991, 64, 685-687.
24. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J. Chem. Phys. 2010, 132, doi:10.1063/1.3382344.
25. Hutter, J.; Parrinello, M.; Marx, D.; Focher, P.; Tuckerman, M.; Andreoni, W.; Curioni, A.; Fois, E.; Roetlisberger, U.; Giannozzi, P.; et al. Computer code CPMD, version 3.9; Copyright IBM Corp.: Armonk, NY, USA; MPI-FKF Stuttgart ed.: Stuttgart, Germary, 2012.
26. Becke, A.D. Density-functional exchange-energy approximation with correct asymptotic-behaviour. Phys. Rev. A 1988, 38, 3098-3100.
27. Lee, C.T.; Yang, W.T.; Parr, R.G. Development of the colle-salvetti correlation-energy formula into a functional of the electron-density. Phys. Rev. B 1988, 37, 785-789.
28. Mühlbacher, D.; Scharber, M.; Morana, M.; Zhu, Z.; Waller, D.; Gaudiana, R.; Brabec, C. High photovoltaic performance of a low-bandgap polymer. Adv. Mater. 2006, 18, 2884-2889.
29. Brown, S.P. Applications of high-resolution 1H solid-state NMR. Solid State Nucl. Magn. Reson. 2012, 41, 1-27.
30. Bohle, A.; Brunklaus, G.; Hansen, M.R.; Schleuss, T.W.; Kilbinger, A.F.M.; Seltmann, J.; Spiess, H.W. Hydrogen-bonded aggregates of oligoaramide-poly(ethylene glycol) block copolymers. Macromolecules 2010, 43, 4978-4985.
31. Tasios, N.; Grigoriadis, C.; Hansen, M.R.; Wonneberger, H.; Li, C.; Spiess, H.W.; Müllen, K.; Floudas, G. Self-assembly, dynamics, and phase transformation kinetics of donor-acceptor substituted perylene derivatives. J. Am. Chem. Soc. 2010, 132, 7478-7487.
32. Brown, S.P. Recent advances in solid-state MAS NMR methodology for probing structure and dynamics in polymeric and supramolecular systems. Macromol. Rapid Commun. 2009, 30, 688-716.
33. Mafra, L.; Santos, S.M.; Siegel, R.; Alves, I.; Almeida Paz, F.A.; Dudenko, D.; Spiess, H.W. Packing interactions in hydrated and anhydrous forms of the antibiotic ciprofloxacin: A solid-state NMR, X-ray diffraction, and computer simulation study. J. Am. Chem. Soc. 2012, 134, 71-74.
34. Beaujuge, P.M.; Tsao, H.N.; Hansen, M.R.; Amb, C.M.; Risko, C.; Subbiah, J.; Choudhury, K.R.; Mavrinskiy, A.; Pisula, W.; Bredas, J.-L.; et al. Synthetic principles directing charge transport in low-band-gap dithienosilole-benzothiadiazole copolymers. J. Am. Chem. Soc. 2012, 134, 8944-8957.
35. Niedzialek, D.; Lemaur, V.; Dudenko, D.; Shu, J.; Hansen, M.R.; Andreasen, J.W.; Pisula, W.; Müllen, K.; Cornil, J.; Beljonne, D. Probing the relation between charge transport and supramolecular organization down to ångström resolution in a benzothiadiazole-cyclopentadithiophene copolymer. Adv. Mater. 2013, 25, 1939-1947.
36. Dudenko, D.; Kiersnowski, A.; Shu, J.; Pisula, W.; Sebastiani, D.; Spiess, H.W.; Hansen, M.R. A strategy for revealing the packing in semicrystalline p-conjugated polymers: Crystal structure of bulk poly-3-hexyl-thiophene (P3HT). Angew. Chem. Int. Ed. 2012, 51, 11068-11072.
37. Sebastiani, D. Current densities and nucleus-independent chemical shift maps from reciprocal-space density functional perturbation theory calculations. ChemPhysChem 2006, 7, 164-175.
38. Schleyer, P.V.R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. Nucleus-independent chemical shifts: A simple and efficient aromaticity probe. J. Am. Chem. Soc. 1996, 118, 6317-6318.
39. Sebastiani, D.; Kudin, K.N. Electronic response properties of carbon nanotubes in magnetic fields. ACS Nano 2008, 2, 661-668.
40. Feng, X.; Marcon, V.; Pisula, W.; Hansen, M.R.; Kirkpatrick, J.; Grozema, F.; Andrienko, D.; Kremer, K.; Müllen, K. Towards high charge-carrier mobilities by rational design of the shape and periphery of discotics. Nat. Mater. 2009, 8, 421-426;
41. Feng, X.; Pisula, W.; Müllen, K. From helical to staggered stacking of zigzag nanographenes. J. Am. Chem. Soc. 2007, 129, 14116-14117.