Molecular packing-induced transition between ambipolar and unipolar behavior in dithiophene-4,9-dione-containing organic semiconductors

Advanced Functional Materials

Volumn 24, Issue 19, 2014, Pages 2907-2915

  Xu, Huan ^a   Zhou, Ye Cheng ^a   Zhou, Xing Yu ^a   Liu, Ke ^a   Cao, Lu Ya ^a   Ai, Yong ^a   Fan, Zhi Ping ^a   Zhang, Hao Li ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

ambipolar transistors; fermi golden rule; molecular packing; organic field effect transistors; organic semiconductors; random walk simulations

Indexed keywords

MICROSTRUCTURE; ORGANIC FIELD EFFECT TRANSISTORS; SEMICONDUCTING ORGANIC COMPOUNDS; TRANSPORT PROPERTIES;

AMBIPOLAR TRANSISTORS; COMPLEMENTARY METAL OXIDE SEMICONDUCTORS; ELECTROCHEMICAL MEASUREMENTS; FERMI GOLDEN RULE; MOLECULAR PACKINGS; ORGANIC FIELD-EFFECT TRANSISTOR (OFETS); RANDOM WALK SIMULATION; THEORETICAL INVESTIGATIONS;

TRANSISTORS;

EID: 84900854808     PISSN: 1616301X     EISSN: 16163028     Source Type: Journal    
DOI: 10.1002/adfm.201302855     Document Type: Article

References (57)

1. a) V. C. Sundar, J. Zaumseil, V. Podzorov, E. Menard, R. L. Willett, T. Someya, M. E. Gershenson, J. A. Rogers, Science 2004, 303, 1644
2. b) M. Mas-Torrent, C. Rovira, Chem. Soc. Rev. 2008, 37, 827
3. c) Y. Wen, Y. Liu, Y. Guo, Gui Yu, W. Hu, Chem. Rev. 2011, 111, 3358
4. d) J. Mei, Y. Diao, A. L. Appleton, L. Fang, Z. Bao, J. Am. Chem. Soc. 2013, 135, 6724.
5. a) Y. Wen, Y. Liu, Adv. Mater. 2010, 22, 1331
6. b) C. Wang, H. Dong, W. Hu, Y. Liu, D. Zhu, Chem. Rev. 2012, 112, 2208.
7. a) J. Zaumseil, H. Sirringhaus, Chem. Rev. 2007, 107, 1296
8. b) K.-J. Baeg, J. Kim, D. Khim, M. Caironi, D.-Y. Kim, I.-K. You, J. R. Quinn, A. Facchetti, Y.-Y. Noh, ACS Appl. Mater. Interfaces 2011, 3, 3205
9. c) M. Irimia-Vladu, E. D. Głowacki, P. A. Troshin, G. Schwabegger, L. Leonat, D. K. Susarova, O. Krystal, M. Ullah, Y. Kanbur, M. A. Bodea, V. F. Razumov, H. Sitter, S. Bauer, N. S. Sariciftci, Adv. Mater. 2012, 24, 375.
10. a) Z. Liang, Q. Tang, R. Mao, D. Liu, J. Xu, Q. Miao, Adv. Mater. 2011, 23, 5514
11. b) H. Usta, A. Facchetti, T. J. Marks, J. Am. Chem. Soc. 2008, 130, 8580.
12. a) J. Cornil, J.-L. Brédas, J. Zaumseil, H. Sirringhaus, Adv. Mater. 2007, 19, 1791
13. b) H. Jiang, Macromol. Rapid. Commun. 2010, 31, 2007.
14. a) S. Seo, B.-N. Park, P. G. Evans, Appl. Phys. Lett. 2006, 88, 232114
15. b) T. Takahashi, T. Takenobu, J. Takeya, Y. Iwasa, Appl. Phys. Lett. 2006, 88, 033505
16. c) E. M. Muller, J. A. Marohn, Adv. Mater. 2005, 17, 1410
17. d) V. Coropceanu, J. Cornil, D. A. da Silva Filho, Y. Olivier, R. Silbey, J.-L. Brédas, Chem. Rev. 2007, 107, 926
18. e) C. Reese, M. E. Roberts, S. R. Parkin, Z. Bao, Adv. Mater. 2009, 21, 3678
19. f) T. Minari, Y. Miyata, M. Terayama, T. Nemoto, T. Nishinaga, K. Komatsu, S. Isoda, Appl. Phys. Lett. 2006, 88, 083514.
20. a) J. J. Brondijk, F. Torricelli, E. C. P. Smits, P. W. M. Bloma, D. M. d. Leeuw, Org. Electron. 2012, 13, 1526
21. b) B. B.Y. Hsu, E. B. Namdas, J. D. Yuen, S. Cho, D. W. Samuel, A. J. Heeger, Adv. Mater. 2010, 22, 4649.
22. a) A. Fuchs, T. Steinbrecher, M. S. Mommer, Y. Nagata, M. Elstnerb, C. Lennartz, Phys. Chem. Chem. Phys. 2012, 14, 4259
23. b) J. J. Kwiatkowski, J. Nelson, H. Li, J. L. Brédas, W. Wenzelc, C. Lennartzd, Phys. Chem. Chem. Phys. 2008, 10, 1852
24. c) H. Liu, S. Kang, J. Y. Lee, J. Phys. Chem. B 2011, 115, 5113.
25. a) F.-C. Chen, L.-J. Kung, T.-H. Chen, Y.-S. Lin, Appl. Phys. Lett. 2007, 90, 073504
26. b) C. Di, G. Yu, Y. Liu, Y. Guo, Y. Wang, W. Wu, D. Zhu, Adv. Mater. 2008, 20, 1286.
27. a) Y.-Y. Liu, C.-L. Song, W.-J. Zeng, K.-G. Zhou, Z.-F. Shi, C.-B. Ma, F. Yang, H.-L. Zhang, X. Gong, J. Am. Chem. Soc. 2010, 132, 16349
28. b) C.-L. Song, C.-B. Ma, F. Yang, W.-J. Zeng, H.-L. Zhang, X. Gong, Org. Lett. 2011, 13, 2880
29. c) J. Wang, K. Liu, Y.-Y. Liu, C.-L. Song, Z.-F. Shi, J.-B. Peng, H.-L. Zhang, X.-P. Cao, Org. Lett. 2009, 11, 2563
30. d) W.-J. Zeng, X.-Y. Zhou, X.-J. Pan, C.-L. Song, H.-L. Zhang, AIP Advances 2013, 3, 012101.
31. M. L. Tang, A. D. Reichardt, P. Wei, Z. Bao, J. Am. Chem. Soc. 2009, 131, 5264.
32. a) C. Piliego, D. Jarzab, G. Gigli, Z. Chen, A. Facchetti, M. A. Loi, Adv. Mater. 2009, 21, 1573
33. b) A. C. Arias, J. D. MacKenzie, I. McCulloch, J. Rivnay, A. Salleo, Chem. Rev. 2010, 110, 3.
34. K. Xiao, R. Li, J. Tao, E. A. Payzant, I. N. Ivanov, A. A. Puretzky, W. Hu, D. B. Geohegan, Adv. Funct. Mater. 2009, 19, 3776.
35. S. K. Park, J. H. Kim, S.-J. Yoon, O. K. Kwon, B.-K. An, S. Y. Park, Chem. Mater. 2012, 24, 3263.
36. a) T. Lei, Y. Cao, X. Zhou, Y. Peng, J. Bian, J. Pei, Chem. Mater. 2012, 24, 1762
37. b) T. Lei, J.-H. Dou, J. Pei, Adv. Mater. 2012, 24, 6457
38. c) F. Zhang, Y. Hu, T. Schuettfort, C. Di, X. Gao, C. R. McNeill, L. Thomsen, S. C. B. Mannsfeld, W. Yuan, H. Sirringhaus, D. Zhu, J. Am. Chem. Soc. 2013, 135, 2338.
39. a) J. Wang, W. Zeng, H. Xu, B. Li, X. Cao, H. Zhang, Chin. J. Chem. 2012, 30, 681
40. b) H. Tian, Y. Deng, F. Pan, L. Huang, D. Yan, Y. Geng, F. Wanga, J. Mater. Chem. 2010, 20, 7998.
41. A. L. Briseno, Q. Miao, M.-M. Ling, C. Reese, H. Meng, Z. Bao, F. Wudl, J. Am. Chem. Soc. 2006, 128, 15576.
42. a) Y. Sun, L. Tan, S. Jiang, H. Qian, Z. Wang, D. Yan, C. Di, Y. Wang, W. Wu, G. Yu, S. Yan, C. Wang, W. Hu, Y. Liu, D. Zhu, J. Am. Chem. Soc. 2007, 129, 1882
43. b) C. Di, G. Yu, Y. Liu, D. Zhu, J. Phy. Chem. B 2007, 111, 14083.
44. S. C. B. Mannsfeld, M. L. Tang, Z. Bao, Adv. Mater. 2011, 23, 127.
45. L.-L. Chua, J. Zaumseil, J.-F. Chang, E. C.-W. Ou, P. K.-H. Ho, H. Sirringhaus, R. H. Friend, Nature 2005, 434, 194.
46. J. L. Brédas, J. P. Calbert, D. A. da Silva Filho, J. Cornil, Proc. Natl. Acad. Sci. USA 2002, 99, 5804.
47. X. Yang, L. Wang, C. Wang, W. Long, Z. Shuai, Chem. Mater. 2008, 20, 3205.
48. a) L. Wang, Q. Li, Z. Shuai, L. Chenc, Q. Shic, Phys. Chem. Chem. Phys. 2010, 12, 3309
49. b) G. Nan, X. Yang, L. Wang, Z. Shuai, Y. Zhao, Phys. Rev. B 2009, 79, 115203.
50. a) W.-Q. Deng, W. A. Goddard, J. Phy. Chem. B 2004, 108, 8614
51. b) S.-H. Wen, A. Li, J. Song, W.-Q. Deng, K.-L. Han, W. A. Goddard, J. Phy. Chem. B 2009, 113, 8813.
52. J. Jortner, J. Chem. Phys. 1976, 64, 4860
53. b) S. H. Lin, C. H. Chang, K. K. Liang, R. Chang, Y. J. Shiu, J. M. Zhang, T. S. Yang, M. Hayashi, F. C. Hsu, Adv. Chem. Phys. 2002, 121, 1.
54. a) K. Senthilkumar, F. C. Grozema, F. M. Bickelhaupt, L. D. A. Siebbelesb, J. Chem. Phys. 2003, 119, 9809
55. b) G. Te Velde, F. M. Bickelhaupt, E. J. Baerends, C. Fonseca Guerra, S. J. A. Van Gisbergen, J. G. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931.
56. R. Li, J. W. Ward, D.-M. Smilgies, M. M. Payne, J. E. Anthony, O. D. Jurchescu, A. Amassian, Adv. Mater. 2012, 24, 5553.
57. S. S. Lee, C. S. Kim, E. D. Gomez, B. Purushothaman, M. F. Toney, C. Wang, A. Hexemer, J. E. Anthony, Y.-L. Loo, Adv. Mater. 2009, 21, 3605.