Chinese Journal of Organic Chemistry >
Research Progress in Isoindigo-Based Polymer Field-Effect Transistor Materials
Received date: 2016-06-08
Revised date: 2016-07-04
Online published: 2016-07-08
Supported by
Project supported by the Major State Basic Research Development Program from the Ministry of Science and Technology (973 Program, No.2013CB933501), and the National Natural Science Foundation of China (No.21302009).
Since the 1980 s, organic electronics had made great progress. Organic semiconductors have attracted much attention of scientists from both academy and industry due to their promising applications in low-cost, lightweight, flexible and solution-processable electronics. The development of the third-generation donor-acceptor (D-A) polymers greatly improved the device performance of organic semiconductors. Recently, isoindigo-based polymers develop rapidly, especially as organic field-effect transistors (OFETs) materials, and high hole mobilities up to 3.62 cm2·V-1·s-1 for IID and 14.4 cm2·V-1·s-1 for its derivatives, were successfully achieved. In this review, the recent advance in isoindigo-based polymer field-effect transistor materials is summarized, which focus on the molecular design and synthesis, device fabrication and structure-property rela-tionship study of isoindigo-based polymers, aiming to providing valuable information for the materials exploitation in the future.
Lu Yang , Ding Yifan , Wang Jieyu , Pei Jian . Research Progress in Isoindigo-Based Polymer Field-Effect Transistor Materials[J]. Chinese Journal of Organic Chemistry, 2016 , 36(10) : 2272 -2283 . DOI: 10.6023/cjoc201606015
[1] Heeger, A. J.; Sariciftci, N. S.; Namdas, E. B. Semiconducting and Metallic Polymers, Oxford University Press, 2010.
[2] Chiang, C. K.; Fincher Jr, C.; Park, Y. W.; Heeger, A. J.; Shirakawa, H.; Louis, E. J.; Gau, S. C.; MacDiarmid, A. G. Phys. Rev. Lett. 1977, 39, 1098.
[3] Tsumura, A.; Koezuka, H.; Ando, T. Appl. Phys. Lett. 1986, 49, 1210.
[4] Tang, C. W. Appl. Phys. Lett. 1986, 48, 183.
[5] Tang, C. W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913.
[6] Heeger, A. J. Chem. Soc. Rev. 2010, 39, 2354.
[7] Yuen, J. D.; Wudl, F. Energy Environ. Sci. 2013, 6, 392.
[8] Nielsen, C. B.; Turbiez, M.; McCulloch, I. Adv. Mater. 2013, 25, 1859.
[9] Zhan, X.; Facchetti, A.; Barlow, S.; Marks, T. J.; Ratner, M. A.; Wasielewski, M. R.; Marder, S. R. Adv. Mater. 2011, 23, 268.
[10] Irimia-Vladu, M.; G?owacki, E. D.; Troshin, P. A.; Schwabegger, G.; Leonat, L.; Susarova, D. K.; Krystal, O.; Ullah, M.; Kanbur, Y.; Bodea, M. A. Adv. Mater. 2012, 24, 375.
[11] Papageorgiou, C.; Borer, X. Helv. Chim. Acta 1988, 71, 1079.
[12] Mei, J.; Graham, K. R.; Stalder, R.; Reynolds, J. R. Org. Lett. 2010, 12, 660.
[13] Estrada, L. A.; Stalder, R.; Abboud, K. A.; Risko, C.; Brédas, J.-L.; Reynolds, J. R. Macromolecules 2013, 46, 8832.
[14] Lei, T.; Cao, Y.; Fan, Y.; Liu, C.-J.; Yuan, S.-C.; Pei, J. J. Am. Chem. Soc. 2011, 133, 6099.
[15] Gholamzadeh, P.; Mohammadi Ziarani, G.; Badiei, A.; Abolhassani Soorki, A.; Lashgari, N. Res. Chem. Intermed. 2012, 39, 3925.
[16] Bergman, J.; Romero, I. J. Heterocycl. Chem. 2010, 47, 1215.
[17] Zhao, N.; Qiu, L.; Wang, X.; An, Z.; Wan, X. Tetrahedron Lett. 2014, 55, 1040.
[18] Bogdanov, A.; Mironov, V.; Musin, L.; Musin, R. Synthesis 2010, 3268.
[19] El-Kateb, A.; Hennawy, I.; Shabana, R.; Osman, F. Phosphorus, Sulfur Relat. Elem. 1984, 20, 329.
[20] Lathourakis, G. E.; Litinas, K. E. J. Chem. Soc., Perkin Trans. 11996, 491.
[21] Minami, T.; Matsumoto, M.; Agawa, T. J. Chem. Soc., Chem. Commun. 1976, 1053b.
[22] Wang, E.; Mammo, W.; Andersson, M. R. Adv. Mater. 2014, 26, 1801.
[23] Mei, J.; Kim, D. H.; Ayzner, A. L.; Toney, M. F.; Bao, Z. J. Am. Chem. Soc. 2011, 133, 20130.
[24] Mei, J.; Wu, H. C.; Diao, Y.; Appleton, A.; Wang, H.; Zhou, Y.; Lee, W. Y.; Kurosawa, T.; Chen, W. C.; Bao, Z. Adv. Funct. Mater. 2015, 25, 3455.
[25] Lei, T.; Dou, J. H.; Pei, J. Adv. Mater. 2012, 24, 6457.
[26] Lei, T.; Dou, J.-H.; Ma, Z.-J.; Yao, C.-H.; Liu, C.-J.; Wang, J.-Y.; Pei, J. J. Am. Chem. Soc. 2012, 134, 20025.
[27] Lei, T.; Dou, J.-H.; Ma, Z.-J.; Liu, C.-J.; Wang, J.-Y.; Pei, J. Chem. Sci. 2013, 4, 2447.
[28] Ashraf, R. S.; Kronemeijer, A. J.; James, D. I.; Sirringhaus, H.; McCulloch, I. Chem. Commun. 2012, 48, 3939.
[29] Dutta, G. K.; Han, A. R.; Lee, J.; Kim, Y.; Oh, J. H.; Yang, C. Adv. Funct. Mater. 2013, 23, 5317.
[30] Chen, M. S.; Niskala, J. R.; Unruh, D. A.; Chu, C. K.; Lee, O. P.; Fréchet, J. M. J. Chem. Mater. 2013, 25, 4088.
[31] Xu, S.; Ai, N.; Zheng, J.; Zhao, N.; Lan, Z.; Wen, L.; Wang, X.; Pei, J.; Wan, X. RSC Adv. 2015, 5, 8340.
[32] Hasegawa, T.; Ashizawa, M.; Matsumoto, H. RSC Adv. 2015, 5, 61035.
[33] Meager, I.; Nikolka, M.; Schroeder, B. C.; Nielsen, C. B.; Planells, M.; Bronstein, H.; Rumer, J. W.; James, D. I.; Ashraf, R. S.; Sadhanala, A.; Hayoz, P.; Flores, J.-C.; Sirringhaus, H.; McCulloch, I. Adv. Funct. Mater. 2014, 24, 7109.
[34] Huang, J.; Mao, Z.; Chen, Z.; Gao, D.; Wei, C.; Zhang, W.; Yu, G. Chem. Mater. 2016, 28, 2209.
[35] Zhao, N.; Ai, N.; Cai, M.; Wang, X.; Pei, J.; Wan, X. Polym. Chem. 2016, 7, 235.
[36] Lei, T.; Dou, J. H.; Cao, X. Y.; Wang, J. Y.; Pei, J. J. Am. Chem. Soc. 2013, 135, 12168.
[37] Lei, T.; Dou, J. H.; Cao, X. Y.; Wang, J. Y.; Pei, J. Adv. Mater. 2013, 25, 6589.
[38] Lei, T.; Xia, X.; Wang, J. Y.; Liu, C. J.; Pei, J. J. Am. Chem. Soc. 2014, 136, 2135.
[39] Cao, Y.; Yuan, J.-S.; Zhou, X.; Wang, X.-Y.; Zhuang, F.-D.; Wang, J.-Y.; Pei, J. Chem. Commun. 2015, 51, 10514.
[40] He, Y.; Quinn, J.; Deng, Y.; Li, Y. Org. Electron. 2016, 35, 41.
[41] Jiang, Y.; Gao, Y.; Tian, H.; Ding, J.; Yan, D.; Geng, Y.; Wang, F. Macromolecules 2016, 49, 2135.
[42] Lei, T.; Cao, Y.; Zhou, X.; Peng, Y.; Bian, J.; Pei, J. Chem. Mater. 2012, 24, 1762.
[43] Park, K. H.; Cheon, K. H.; Lee, Y. J.; Chung, D. S.; Kwon, S. K.; Kim, Y. H. Chem. Commun. 2015, 51, 8120.
[44] Kim, G.; Kang, S. J.; Dutta, G. K.; Han, Y. K.; Shin, T. J.; Noh, Y. Y.; Yang, C. J. Am. Chem. Soc. 2014, 136, 9477.
[45] Kim, G.; Han, A. R.; Lee, H. R.; Lee, J.; Oh, J. H.; Yang, C. Chem. Commun. 2014, 50, 2180.
[46] Grenier, F.; Berrouard, P.; Pouliot, J.-R.; Tseng, H.-R.; Heeger, A. J.; Leclerc, M. Polym. Chem. 2013, 4, 1836.
[47] Kim, G.; Han, A. R.; Lee, H. R.; Oh, J. H.; Yang, C. Phys. Chem. Chem. Phys. 2015, 17, 26512.
[48] Lei, T.; Wang, J. Y.; Pei, J. Acc. Chem. Res. 2014, 47, 1117.
[49] Xia, X.; Lei, T.; Pei, J.; Liu, C. Chin. J. Org. Chem. 2014, 34, 1905.
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