Citation: Qian Du, Jing Shao, Yao Gao, Wei-li Li, Hong-kun Tian, Dong-hang Yan, Yan-hou Geng, Fo-song Wang. Acceptor-Donor-Acceptor Conjugated Oligomers Based on Diketopyrrolopyrrole and Thienoacenes with Four, Five and Six Rings for Organic Thin-film Transistors[J]. Chinese Journal of Polymer Science, ;2017, 35(4): 480-489. doi: 10.1007/s10118-017-1885-x shu

Acceptor-Donor-Acceptor Conjugated Oligomers Based on Diketopyrrolopyrrole and Thienoacenes with Four, Five and Six Rings for Organic Thin-film Transistors

Qian Du ^a ,
Jing Shao ^c ,
Yao Gao ^b ,
Wei-li Li ^b ,
Hong-kun Tian ^b ,
Dong-hang Yan ^b ,
Yan-hou Geng ^a,b,, ,
Fo-song Wang ^b

a.
School of Material Science and Engineering and Collaborative Innovation Centre of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin 300072, China
b.
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
c.
The 46 th Institute of the Sixth Academy of China Aerospace Science & Industry Corporation, Hohhot 010010, China

Corresponding author: Yan-hou Geng, yanhou.geng@tju.edu.cn
Received Date: 31 August 2016
Revised Date: 23 September 2016
Accepted Date: 25 September 2016

Fund Project: the Strategic Priority Research Program of the Chinese Academy of Sciences XDB12010300the National Natural Science Foundation of China 51333006

Three acceptor-donor-acceptor (A-D-A) conjugated oligomers, i.e., O1, O2 and O3, have been synthesized using diketopyrrolopyrrole (DPP) as an electron-acceptor unit, and naphtho[1, 2-b:5, 6-b']dithiophene (NDT), anthra[1, 2-b:5, 6-b']dithiophene (ADT) or dithieno[3, 2-b:3', 2'-b']naphtho[1, 2-b:5, 6-b']dithiophene (DTNDT) as electron-donor unit. These oligomers exhibit identical highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels, which were ca.-5.1 and-3.3 eV, respectively. Upon thermal annealing, all three oligomers formed thin films with ordered microstructures, and their organic thin film transistors (OTFTs) exhibited p-type transport behavior. The mobility was increased with an extension of the size of D-units. O3 showed the best OTFT performance with the mobility of up to 0.20 cm²·V^-1·s^-1. The film quality of O3 was improved by adding 1 wt% poly (methylmethacrylate) (PMMA). In consequence, the mobility of the O3-based devices was further enhanced to 0.30 cm²·V^-1·s^-1.
- Diketopyrrolopyrrole (DPP),
- Thienoacene,
- Conjugated oligomers,
- Organic thin-film transistors (OTFTs)
1. [1]
  Wang, C., Dong, H., Hu, W., Liu, Y. and Zhu, D., Chem. Rev., 2012, 112:2208 doi: 10.1021/cr100380z
2. [2]
  Mei, J., Diao, Y., Appleton, A.L., Fang, L. and Bao, Z., J. Am. Chem. Soc., 2013, 135:6724 doi: 10.1021/ja400881n
3. [3]
  Sirringhaus, H., Adv. Mater., 2014, 26:1319 doi: 10.1002/adma.201304346
4. [4]
  Li, J., Zhao, Y., Tan, H.S., Guo, Y., Di, C.A., Yu, G., Liu, Y., Lin, M., Lim, S.H., Zhou, Y., Su, H. and Ong, B.S., Sci. Rep., 2012, 2:754
5. [5]
  Kim, G., Kang, S.J., Dutta, G.K., Han, Y.K., Shin, T.J., Noh, Y.Y. and Yang, C., J. Am. Chem. Soc., 2014, 136:9477 doi: 10.1021/ja504537v
6. [6]
  Kang, I., Yun, H.J., Chung, D.S., Kwon, S.K. and Kim, Y.H., J. Am. Chem. Soc., 2013, 135:14896
7. [7]
  Tseng, H.R., Phan, H., Luo, C., Wang, M., Perez, L.A., Patel, S.N., Ying, L., Kramer, E.J., Nguyen, T.Q., Bazan, G.C. and Heeger, A.J., Adv. Mater., 2014, 26:2993 doi: 10.1002/adma.201305084
8. [8]
  Lee, B.H., Bazan, G.C. and Heeger, A.J., Adv. Mater., 2016, 28:57 doi: 10.1002/adma.201504307
9. [9]
  Ji, Y., Xiao, C., Wang, Q., Zhang, J., Li, C., Wu, Y., Wei, Z., Zhan, X., Hu, W., Wang, Z., Janssen, R.A.J. and Li, W., Adv. Mater., 2016, 28:943
10. [10]
  Yao, J., Yu, C., Liu, Z., Luo, H., Yang, Y., Zhang, G. and Zhang, D., J. Am. Chem. Soc., 2016, 138:173
11. [11]
  Zheng, Y. Q. , Lei, T. , Dou, J. H. , Xia, X. , Wang, J. Y. , Liu, C. J. and Pei, J. , Adv. Mater. , DOI: 10.1002/adma.201600541
12. [12]
  Ni, W., Wan, X., Li, M., Wang, Y. and Chen, Y., Chem. Commun., 2015, 51:4936
13. [13]
  Jo, H., Park, S., Choi, H., Lee, S., Song, K., Biswas, S., Sharma, A., Sharma, G.D. and Ko, J., RSC Adv., 2015, 5:102115 doi: 10.1039/C5RA21657E
14. [14]
  Zhang, Y., Kim, C., Lin, J. and Nguyen, T.Q., Adv. Funct. Mater., 2012, 22:97 doi: 10.1002/adfm.201101820
15. [15]
  Liu, S.Y., Liu, W.Q., Xu, J.Q., Fan, C.C., Fu, W.F., Ling, J., Wu, J.Y., Shi, M.M., Jen, A.K.Y. and Chen, H.Z., ACS Appl. Mater. Interfaces, 2014, 6:6765 doi: 10.1021/am500522x
16. [16]
  Liu, J., Walker, B., Tamayo, A., Zhang, Y. and Nguyen, T.Q., Adv. Funct. Mater., 2013, 23:47
17. [17]
  Elsawy, W., Lee, C.L., Cho, S., Oh, S.H., Moon, S.H., Elbarbary, A. and Lee, J.S., Phys. Chem. Chem. Phys., 2013, 15:15193 doi: 10.1039/c3cp52151f
18. [18]
  Loser, S., Bruns, C.J., Miyauchi, H., Ortiz, R.P., Facchetti, A., Stupp, S.I. and Marks, T.J., J. Am. Chem. Soc., 2011, 133:8142 doi: 10.1021/ja202791n
19. [19]
  Loser, S., Miyauchi, H., Hennek, J.W., Smith, J., Huang, C., Facchetti, A. and Marks, T.J., Chem. Commun., 2012, 48:8511 doi: 10.1039/c2cc32646a
20. [20]
  Harschneck, T., Zhou, N., Manley, E.F., Lou, S.J., Yu, X., Butler, M.R., Timalsina, A., Turrisi, R., Ratner, M.A., Chen, L.X., Chang, R.P.H., Facchetti, A. and Marks, T.J., Chem. Commun., 2014, 50:4099 doi: 10.1039/c3cc49620a
21. [21]
  Wong, W.W.H., Subbiah, J., Puniredd, S.R., Purushothaman, B., Pisula, W., Kirby, N., Müllen, K., Jones, D.J. and Holmes, A.B., J. Mater. Chem., 2012, 22:21131 doi: 10.1039/c2jm34394k
22. [22]
  Choi, Y.S. and Jo, W.H., Org. Electron., 2013, 14:1621 doi: 10.1016/j.orgel.2013.03.031
23. [23]
  Lin, X., Tani, Y., Kanda, R., Nakayama, K. and Yagai, S., J. Mater. Chem. A, 2013, 1:14686
24. [24]
  Huang, J., Zhan, C., Zhang, X., Zhao, Y., Lu, Z., Jia, H., Jiang, B., Ye, J., Zhang, S., Tang, A., Liu, Y., Pei, Q. and Yao, J., ACS Appl. Mater. Interfaces, 2013, 5:2033
25. [25]
  Lin, Y., Ma, L., Li, Y., Liu, Y., Zhu, D. and Zhan, X., Adv. Energy Mater., 2013, 3:1166
26. [26]
  Lee, T.W., Lee, D.H., Hong, T.R., Shi, J., Cho, M.J. and Choi, D.H., Syn. Metal., 2015, 206:24 doi: 10.1016/j.synthmet.2015.05.005
27. [27]
  Duan, X., Xiao, M., Chen, J., Wang, X., Peng, W., Duan, L., Tan, H., Lei, G., Yang, R. and Zhu, W., ACS Appl. Mater. Interfaces, 2015, 7:18292 doi: 10.1021/acsami.5b03338
28. [28]
  Jung, M., Seo, D., Kwak, K., Kim, A., Cha, W., Kim, H., Yoon, Y., Ko, M.J., Lee, D.K., Kim, J.Y., Son, H.J. and Kim, B., Dyes Pigments, 2015, 115:23 doi: 10.1016/j.dyepig.2014.12.003
29. [29]
  Bai, H., Cheng, P., Wang, Y., Ma, L., Li, Y., Zhu, D. and Zhan, X., J. Mater. Chem. A, 2014, 2:778
30. [30]
  Lee, J.W., Choi, Y.S. and Jo, W.H., Org. Electron., 2012, 13:3060 doi: 10.1016/j.orgel.2012.09.004
31. [31]
  Lu, C. and Chen, W., Chem. Asian J., 2013, 8:2813
32. [32]
  Riaño, A., Burrezo, P.M., Mancheño, M.J., Timalsina, A., Smith, J., Facchetti, A., Marks, T.J., Navarrete, J.T.L., Segura, J.L., Casado, J. and Ortiz, R.P., J. Mater. Chem. C, 2014, 2:6376 doi: 10.1039/C4TC00714J
33. [33]
  Yu, C., Liu, Z., Yang, Y., Yao, J., Cai, Z., Luo, H., Zhang, G. and Zhang, D., J. Mater. Chem. C, 2014, 2:10101
34. [34]
  Dharmapurikar, S.S., Arulkashmir, A., Das, C., Muddellu, P. and Krishnamoorthy, K., ACS Appl. Mater. Interfaces, 2013, 5:7086
35. [35]
  Kyaw, A.K.K., Wang, D.H., Gupta, V., Leong, W.L., Ke, L., Bazan, G.C. and Heeger, A.J., ACS Nano, 2013, 7:4569
36. [36]
  Shao, J., Zhang, X., Tian, H., Geng, Y. and Wang, F., J. Mater. Chem. C, 2015, 3; 7567
37. [37]
  Yi, Z., Wang, S. and Liu, Y., Adv. Mater., 2015, 27:3589
38. [38]
  Nielsen, C.B., Turbiez, M. and McCulloch, I., Adv. Mater., 2013, 25:1859 doi: 10.1002/adma.v25.13
39. [39]
  Li, Y., Singh, S.P. and Sonar, P., Adv. Mater., 2010, 22:4862 doi: 10.1002/adma.201002313
40. [40]
  Bundgaard, E. and Krebs, F.C., Sol. Energy Mater. Sol. Cells, 2007, 91:954 doi: 10.1016/j.solmat.2007.01.015
41. [41]
  Brocks, G. and Tol, A., J. Phys. Chem., 1996, 100:1838 doi: 10.1021/jp952276c
42. [42]
  Kasha, M., Rawls, H.R. and Ashraf El-Bayoumi, M., Pure Appl. Chem., 1965, 11:371
43. [43]
  Cardona, C.M., Li, W., Kaifer, A.E., Stockdale, D. and Bazan, G.C., Adv. Mater., 2011, 23:2367
44. [44]
  Dimitrakopoulos, C.D. and Malenfant, P.R.L., Adv. Mater., 2002, 14:99 doi: 10.1002/(ISSN)1521-4095
45. [45]
  Lee, W.H., Kwak, D., Anthony, J.E., Lee, H.S., Choi, H.H., Kim, D.H., Lee, S.G. and Cho, K., Adv. Funct. Mater., 2012, 22:267
46. [46]
  Kang, J., Shin, N., Jang, D.Y., Prabhu, V.M. and Yoon, D.Y., J. Am. Chem. Soc., 2008, 130:12273
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