Critical role of alkyl chain branching of organic semiconductors in enabling solution-processed N-channel organic thin-film transistors with mobility of up to 3.50 cm2 V-1 s-1

Journal of the American Chemical Society

Volumn 135, Issue 6, 2013, Pages 2338-2349

  Zhang, Fengjiao ^a   Hu, Yunbin ^b   Schuettfort, Torben ^c   Di, Chong An ^a   Gao, Xike ^b   McNeill, Christopher R ^d   Thomsen, Lars ^e   Mannsfeld, Stefan C B ^f   Yuan, Wei ^b   Sirringhaus, Henning ^c   Zhu, Daoben ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^d MONASH UNIVERSITY   (Australia)

^e AUSTRALIAN SYNCHROTRON   (Australia)

^f SLAC NATIONAL ACCELERATOR LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AIR-STABLE; ALKYL CHAIN; BRANCHING POINTS; DEVICE OPTIMIZATION; DOMAIN SIZE; FILM MICROSTRUCTURES; FUNDAMENTAL UNITS; GOOD COMPATIBILITY; GRAZING INCIDENCE X-RAY DIFFRACTION; HIGH CHARGES; HIGH CRYSTALLINITY; MALONONITRILES; MOLECULAR PACKINGS; N-CHANNEL; NAPHTHALENE DIIMIDES; NEAR EDGE X-RAY ABSORPTION FINE STRUCTURES; ORGANIC THIN FILM TRANSISTOR (OTFTS); ORGANIC THIN FILM TRANSISTORS; SIDE-CHAINS; SOLUTION PROCESSABLE; SOLUTION-PROCESSED; SUBSTITUTED SIDE CHAINS; SYNCHROTRON MEASUREMENTS; SYSTEMATIC STUDY; THIN FILM MICROSTRUCTURES; TRANSPORT MOBILITY; UNIT CELLS; WET TECHNIQUES;

CHAIN LENGTH; ELECTRON MOBILITY; MICROSTRUCTURE; NAPHTHALENE; X RAY DIFFRACTION;

THIN FILM TRANSISTORS;

ALKYL GROUP; DITHIOL DERIVATIVE; MALONONITRILE; NAPHTHALENE DERIVATIVE;

AMBIENT AIR; ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ELECTRICITY; ELECTRON; ELECTRON TRANSPORT; FILM; MOLECULAR ELECTRONICS; MOLECULAR PROBE; MOLECULAR SIZE; MOLECULAR STABILITY; ORGANIC CHEMISTRY; ORGANIC THIN FILM TRANSISTOR; SEMICONDUCTOR; SOLUTION AND SOLUBILITY; SUBSTITUTION REACTION; SYNCHROTRON; X RAY ABSORPTION SPECTROSCOPY; X RAY DIFFRACTION;

HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; IMIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHALENES; NITRILES; SEMICONDUCTORS; SOLUTIONS; TRANSISTORS, ELECTRONIC;

EID: 84873667634     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja311469y     Document Type: Article

References (64)

1. Sokolov, A. N.; Tee, B. C.-K.; Bettinger, C. J.; Tok, J. B.-H.; Bao, Z. N. Acc. Chem. Res. 2012, 45, 361-371
2. Di, C. A.; Zhang, F. J.; Zhu, D. B. Adv. Mater. 2012, 25, 313-330
3. Chang, J.-W.; Wang, C.-G.; Huang, C.-Y.; Tsai, T.-D.; Guo, T.-F.; Wen, T.-C. Adv. Mater. 2011, 23, 4077-4081
4. Baude, P. F.; Ender, D. A.; Haase, M. A.; Kelley, T. W.; Muyres, D. V.; Theiss, S. D. Appl. Phys. Lett. 2003, 82, 3964-3966
5. Chen, Z.; Lee, M. J.; Shahid Ashraf, R.; Gu, Y.; Albert-Seifried, S.; Meedom Nielsen, M.; Schroeder, B.; Anthopoulos, T. D.; Heeney, M.; McCulloch, I.; Sirringhaus, H. Adv. Mater. 2012, 24, 647-652
6. Dodabalapur, A. Mater. Today 2006, 9, 24-30
7. Zhang, H. T.; Guo, X. F.; Hui, J. S.; Hu, S. X.; Xu, W.; Zhu, D. B. Nano Lett. 2011, 11, 4939-4946
8. B.Mannsfeld, S. C.; Tee, B. C.-K.; Stoltenberg, R.; Chen, C. V. H.-H.; Barman, S.; O.Muir, B. V.; Sokolov, A. N.; Reese, C.; Bao, Z. Nat. Mater. 2010, 9, 859-864
9. Gelinck, G. H.; Huitema, H. E. A.; van Veenendaal, E.; Cantatore, E.; Schrijnemakers, L.; van der Putten, J. B. P. H.; Geuns, T. C. T.; Beenhakkers, M.; Giesbers, J. B.; Huisman, B.-H.; Meijer, E. J.; Benito, E. M.; Touwslager, F. J.; Marsman, A. W.; van Rens, B. J. E.; de Leeuw, D. M. Nat. Mater. 2004, 3, 106-110
10. Someya, T.; Dodabalapur, A.; Huang, J.; See, K. C.; Katz, H. E. Adv. Mater. 2010, 22, 3799-3811
11. Rogers, J. A.; Bao, Z.; Baldwin, K.; Dodabalapur, A.; Crone, B.; Raju, V. R.; Kuck, V.; Katz, H.; Amundson, K.; Ewing, J.; Drzaic, P. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 4835-4840
12. Someya, T.; Sekitani, T.; Iba, S.; Kato, Y.; Kawaguchi, H.; Sakurai, T. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 9966-9970
13. Sirringhaus, H. Adv. Mater. 2005, 17, 2411-2425
14. Usta, H.; Risko, C.; Wang, Z.; Huang, H.; Deliomeroglu, M. K.; Zhukhovitskiy, A.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2009, 131, 5586-5608
15. Tsao, H. N.; Cho, D.; Andreasen, J. W.; Rouhanipour, A.; Breiby, D. W.; Pisula, W.; Müllen, K. Adv. Mater. 2009, 21, 209-212
16. Jiang, W.; Zhou, Y.; Geng, H.; Jiang, S.; Yan, S.; Hu, W.; Wang, Z.; Shuai, Z.; Pei, J. J. Am. Chem. Soc. 2011, 133, 1-3
17. Li, H.; Tee, B. C. K.; Cha, J. J.; Cui, Y.; Chung, J. W.; Lee, S. Y.; Bao, Z. J. Am. Chem. Soc. 2012, 134, 2760-2765
18. Pan, H.; Li, Y.; Wu, Y.; Liu, P.; Ong, B. S.; Zhu, S.; Xu, G. J. Am. Chem. Soc. 2007, 129, 4112-4113
19. Forrest, S. R. Nature 2004, 428, 911-918
20. Minemawari, H.; Yamada, T.; Matsui, H.; Tsutsumi, J. y.; Haas, S.; Chiba, R.; Kumai, R.; Hasegawa, T. Nature 2011, 475, 364-367
21. Guo, X.; Ortiz, R. P.; Zheng, Y.; Kim, M.-G.; Zhang, S.; Hu, Y.; Lu, G.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2011, 133, 13685-13697
22. Wang, S.; Kiersnowski, A.; Pisula, W.; Müllen, K. J. Am. Chem. Soc. 2012, 134, 4015-4018
23. Lee, W.-Y.; Oh, J. H.; Suraru, S.-L.; Chen, W.-C.; Würthner, F.; Bao, Z. Adv. Funct. Mater. 2011, 21, 4173-4181
24. Chen, H.; Guo, Y.; Yu, G.; Zhao, Y.; Zhang, J.; Gao, D.; Liu, H.; Liu, Y. Adv. Mater. 2012, 24, 4618-4622
25. 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.; Takeya, J. Adv. Mater. 2011, 23, 1626-1629
26. Smith, J.; Zhang, W.; Sougrat, R.; Zhao, K.; Li, R.; Cha, D.; Amassian, A.; Heeney, M.; McCulloch, I.; Anthopoulos, T. D. Adv. Mater. 2012, 24, 2441-2446
27. Giri, G.; Verploegen, E.; Mannsfeld, S. C. B.; Atahan-Evrenk, S.; Kim, D. H.; Lee, S. Y.; Becerril, H. A.; Aspuru-Guzik, A.; Toney, M. F.; Bao, Z. Nature 2011, 480, 504-508
28. 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. J. Am. Chem. Soc. 2011, 133, 2605-2612
29. Li, J.; Zhao, Y.; Tan, H. S.; Guo, Y. L.; Di, C. A.; Yu, G.; Liu, Y. Q.; Lin, M.; Lim, S. H.; Zhou, Y.; Su, H.; Ong, B. S. Sci. Rep. 2012, 2, 754
30. Yan, H.; Chen, Z.; Zheng, Y.; Newman, C.; Quinn, J. R.; Dötz, F.; Kastler, M.; Facchetti, A. Nature 2009, 457, 679-686
31. Gao, X. K.; Di, C. A.; Hu, Y.; Yang, X.; Fan, H.; Zhang, F.; Liu, Y.; Li, H.; Zhu, D. B. J. Am. Chem. Soc. 2010, 132, 3697-3699
32. Zhao, Y.; Di, C. A.; Gao, X. K.; Hu, Y. B.; Guo, Y. L.; Zhang, L.; Liu, Y.; Wang, J. Z.; Hu, W. P.; Zhu, D. B. Adv. Mater. 2011, 23, 2448-2453
33. Hu, Y. B.; Qin, Y. K.; Gao, X. K.; Zhang, F. J.; Di, C. A.; Zhao, Z.; Li, H. Y.; Zhu, D. B. Org. Lett. 2012, 14, 292-295
34. Polander, L. E.; Tiwari, S. P.; Pandey, L.; Seifried, B. M.; Zhang, Q.; Barlow, S.; Risko, C.; Brédas, J.-L.; Kippelen, B.; Marder, S. R. Chem. Mater. 2011, 23, 3408-3410
35. Stolte, M.; Gsänger, M.; Hofmockel, R.; Suraru, S.-L.; Würthner, F. Phys. Chem. Chem. Phys. 2012, 14, 14181-14185
36. Wu, Q. H.; Li, R. J.; Hong, W.; Li, H.; Gao, X. K.; Zhu, D. B. Chem. Mater. 2011, 23, 3138-3140
37. Zhong, H.; Smith, J.; Rossbauer, S.; White, A. J. P.; Anthopoulos, T. D.; Heeney, M. Adv. Mater. 2012, 24, 3205-3211
38. Qiao, Y. L.; Guo, Y. L.; Yu, C. M.; Zhang, F. J.; Xu, W.; Liu, Y. Q.; Zhu, D. B. J. Am. Chem. Soc. 2012, 134, 4084-4087
39. Guo, X.; Watson, M. D. Org. Lett. 2008, 10, 5333-5336
40. Guo, X.; Kim, F. S.; Seger, M. J.; Jenekhe, S. A.; Watson, M. D. Chem. Mater. 2012, 24, 1434-1442
41. Chen, Z.; Zheng, Y.; Yan, H.; Facchetti, A. J. Am. Chem. Soc. 2009, 131, 8-9
42. Guo, X.; Ortiz, R. P.; Zheng, Y.; Hu, Y.; Noh, Y.-Y.; Baeg, K.-J.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2011, 13, 1405-1418
43. Hu, Y. B.; Gao, X. K.; Di, C. A.; Yang, X. D.; Zhang, F.; Liu, Y. Q.; Li, H. X.; Zhu, D. B. Chem. Mater. 2011, 23, 1204-1215
44. Sung, A.; Ling, M. M.; Tang, M. L.; Bao, Z.; Locklin, J. Chem. Mater. 2007, 19, 2342-2351
45. Osaka, I.; Zhang, R.; Sauvé, G.; Smilgies, D.-M.; Kowalewski, T.; McCullough, R. D. J. Am. Chem. Soc. 2009, 131, 2521-2529
46. Osaka, I.; Abe, T.; Shinamura, S.; Miyazaki, E.; Takimiya, K. J. Am. Chem. Soc. 2010, 132, 5000-5001
47. Kline, R. J.; DeLongchamp, D. M.; Fischer, D. A.; Lin, E. K.; Richter, L. J.; Chabinyc, M. L.; Toney, M. F.; Heeney, M.; McCulloch, I. Macromolecules 2007, 40, 7960-7965
48. Bao, Z. N.; Lovinger, A. J. Chem. Mater. 1999, 11, 2607-2612
49. Ong, B. S.; Wu, Y.; Liu, P.; Gardner, S. J. Am. Chem. Soc. 2004, 126, 3378-3379
50. McCulloch, I.; Heeney, M.; Bailey, C.; Genevicius, K.; MacDonald, I.; Shkunov, M.; Sparrowe, D.; Tierney, S.; Wagner, R.; Zhang, W.; Chabinyc, M. L.; Kline, R. J.; McGehee, M. D.; Toney, M. F. Nat. Mater. 2006, 5, 328-333
51. Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. M.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P.; Leeuw, D. M. d. Nature 1999, 401, 685-688
52. Lei, T.; Dou, J.-H.; Pei, J. Adv. Mater. 2012, 24, 6457-6461
53. Mei, J.; Kim, D. H.; Ayzner, A. L.; Toney, M. F.; Bao, Z. J. Am. Chem. Soc. 2011, 133, 20130-20133
54. Nolde, F.; Pisula, W.; Müller, S.; Kohl, C.; Müllen, K. Chem. Mater. 2006, 18, 3715-3725
55. Savage, R. C.; Orgiu, E.; Mativetsky, J. M.; Pisula, W.; Schnitzler, T.; Eversloh, C. L.; Li, C.; Müllen, K.; Samori, P. Nanoscale 2012, 4, 2387-2393
56. Zhan, X.; Tan, Z. A.; Domercq, B.; An, Z.; Zhang, X.; Barlow, S.; Li, Y.; Zhu, D. B.; Kippelen, B.; Marder, S. R. J. Am. Chem. Soc. 2007, 129, 7246-7247
57. Guo, X.; Kim, F. S.; Jenekhe, S. A.; Watson, M. D. J. Am. Chem. Soc. 2009, 131, 7206-7207
58. Chabinyc, M. L.; Toney, M. F.; Kline, R. J.; McCulloch, I.; Heeney, M. J. Am. Chem. Soc. 2007, 129, 3226-3237
59. Schuettfort, T.; Watts, B.; Thomsen, L.; Lee, M.; Sirringhaus, H.; McNeill, C. R. ACS Nano 2012, 6, 1849-1864
60. Cowie, B. C. C.; Tadich, A.; Thomsen, L. AIP Conf. Proc. 2010, 1234, 307-310
61. Watts, B.; Thomsen, L.; Dastoor, P. C. J. Electron Spectrosc. Relat. Phenom. 2006, 151, 105-120
62. Stöhr, J. NEXAFS Spectroscopy; Springer-Verlag: Heidelberg, Germany, 1992.
63. Rivnay, J.; Mannsfeld, S. C. B.; Miller, C. E.; Salleo, A.; Toney, M. F. Chem. Mater. 2012, 112, 5488-5519
64. Cho, E.; Risko, C.; Kim, D.; Gysel, R.; Cates Miller, N.; Breiby, D. W.; McGehee, M. D.; Toney, M. F.; Kline, R. J.; Bredas, J.-L. J. Am. Chem. Soc. 2012, 134, 6177-6190