Citation: Wang Menghan, Wan Li, Gao Xuyu, Yuan Wenbo, Fang Junfeng, Tao Youtian, Huang Wei. Synthesis of D-π-A-π-D Type Dopant-Free Hole Transporting Materials and Application in Inverted Perovskite Solar Cells[J]. Acta Chimica Sinica, ;2019, 77(8): 741-750. doi: 10.6023/A19060200 shu

Synthesis of D-π-A-π-D Type Dopant-Free Hole Transporting Materials and Application in Inverted Perovskite Solar Cells

Wang Menghan ^a,† ,
Wan Li ^b,† ,
Gao Xuyu ^a ,
Yuan Wenbo ^a ,
Fang Junfeng ^b,, ,
Tao Youtian ^a,, ,
Huang Wei ^a,c

a.
Key Lab for Flexible Electronics, Institute of Advanced Materials, Nanjing Tech University, Nanjing 211816
b.
Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201
c.
Shaanxi Institute of Flexible Electronics, Northwestern Polytechnical University, Xi'an 710072

Corresponding author: Fang Junfeng, fangjf@nimte.ac.cn Tao Youtian, iamyttao@njtech.edu.cn

^†

Received Date: 6 June 2019
Available Online: 28 August 2019
Fund Project: Project supported by the National Key Research and Development Program of China for the Joint Research Program between China and European Union (No.2016YFE0112000), National Natural Science Foundation of China (No. 61761136013), and the Natural Science Foundation of Jiangsu Province (No.BK20160042)the Natural Science Foundation of Jiangsu Province BK20160042National Natural Science Foundation of China 61761136013the National Key Research and Development Program of China for the Joint Research Program between China and European Union 2016YFE0112000

Figures(9)

Perovskite solar cells (PVSCs) have recently gained much attention for the advantages of low cost and high efficiency. Based on the different device structures, PVSCs can be simply classified into conventional and inverted categories. Compared with the inverted devices, conventional PVSCs generally exhibited higher PCE. Especially, a milestone PCE value of 24.3% was obtained in conventional PVSCs. However, the complexity and high-temperature process in device fabrication further limit their application in flexible and large-scale devices, while the inverted PVSCs can make up the shortcomings of the conventional PVSCs. Commonly, PVSCs devices contain electrodes, electron/hole transporting layers and the perovskite layer. Among the function layers, hole transporting layers (HTLs) play a crucial role in improving the photovoltaic performance of inverted PVSCs. From the materials point of view, the efficient hole transporting materials (HTMs) are mostly inorganic compounds and polymers. On the other side, taking advantages of easy modification, low price, easy preparation and homogeneity in batches, small molecular HTMs afford superior promising in fabricating efficient and stable PVSCs. However, up to date, small molecular HTMs are relatively less explored. To enrich the material species of small molecular HTMs and illustrate their superiorities in constructing stable PVSCs, in this paper, we designed and synthesized three D-π-A-π-D type small molecular HTMs based on triphenylamine (TPA) unit, namely 1-T, 1-OT and 1-OTCN. The optoelectronic properties of these molecules were modified by introducing different electron acceptor/donor groups. Afterwards, employing as dopant-free HTMs in inverted PVSCs, the three small molecules demonstrated distinguished performance. We found that introduction of electron-donating methoxy into 1-T, 1-OT exhibited increased energy levels and hole mobility. On the other hand, the energy levels of 1-OTCN were down-shifted compared to 1-OT, which was attributed from the stronger electron-withdrawing ability of dicyanovinylene group than carbonyl group. Among the devices with new HTMs, 1-OTCN based PVSCs achieved the best PCE of 16.8%, with open-circuit voltage (V_OC) of 1.09 V, short-circuit current density (J_SC) of 20.13 mA·cm^-2 and fill factor (FF) of 78%. Compared with other HTMs, the higher J_SC of 1-OTCN based PVSCs was ascribed from more efficient charge transfer and extraction in the interface of HTL/perovskite. Moreover, in contrast with the hydrophilicity of PEDOT:PSS, the hydrophobicity of 1-OTCN contributed to the satisfactory stability of PVSCs.
- perovskite solar cells,
- organic small molecular hole transporting materials,
- triphenylamine,
- D-π-A-π-D,
- dopant-free,
- stability
1. [1]
  Chai, L.; Zhong, M. Acta Phys. Sin. 2016, 65, 237902(in Chinese). doi: 10.7498/aps.65.237902
2. [2]
  Pan, B.; Zhu, Y.-Z.; Qiu, C.-J.; Wang, B.; Zheng, J.-Y. Acta Chim. Sinica 2018, 76, 215(in Chinese).
3. [3]
  Kojima, A.; Teshima, K.; Shirai, Y.; Miyasaka, T. J. Am. Chem. Soc. 2009, 131, 6050. doi: 10.1021/ja809598r
4. [4]
  https://www.nrel.gov/pv/assets/images/efficiency-chart.png.
5. [5]
  Zhao, C.; Ma, Y.; Wang, Y.; Zhu, X.; Li, H.-Z.; Li, M.-Z.; Song, Y.-L. Acta Chim. Sinica 2018, 76, 9(in Chinese). doi: 10.3866/PKU.WHXB201707072
6. [6]
  Chen, X.-Y.; Xie, J.-J.; Wang, W.; Yuan, H.-H.; Xu, D.; Zhang, T.; He, Y.-L. Shen, H.-J. Acta Chim. Sinica 2019, 77, 9(in Chinese). doi: 10.3866/PKU.WHXB201711141
7. [7]
  Li, C.-P.; Lv, X.-D.; Cao, J.; Tang, Y. Chin. J. Chem. 2019, 37, 30. doi: 10.1002/cjoc.201800469
8. [8]
  Wang, Y.-L.; Chang, S.; Chen, X.-M.; Ren, Y.-D.; Shi, L.-F.; Liu, Y.-H.; Zhong, H.-Z. Chin. J. Chem. 2019, 37, 616. doi: 10.1002/cjoc.201900071
9. [9]
  Etgar, L.; Gao, P.; Xue, Z.; Peng, Q.; Chandiran, A. Q.; Liu, B.; Nazeeruddin, M. K.; Grätzel, M. J. Am. Chem. Soc. 2012, 134, 17396. doi: 10.1021/ja307789s
10. [10]
  Liu, M.; Johnston, M. B.; Snaith, H. J. Nature 2013, 501, 395. doi: 10.1038/nature12509
11. [11]
  Gao, P.; Grätzel, M.; Nazeeruddin, M. K. Energy Environ. Sci. 2014, 7, 2448. doi: 10.1039/C4EE00942H
12. [12]
  Green, M. A.; Ho-Baillie, A.; Snaith, H. J. Nature Photon. 2014, 8, 506. doi: 10.1038/nphoton.2014.134
13. [13]
  Liu, X.-D.; Li, Y.-F. J. Electrochem. 2016, 22, 315.
14. [14]
  Urieta-Mora, J.; García-Benito, I.; Molina-Ontoria, A.; Martín, N. Chem. Soc. Rev. 2018, 47, 8541. doi: 10.1039/C8CS00262B
15. [15]
  Niu, G.-D.; Guo, X.-D.; Wang, L.-D. J. Mater. Chem. A 2015, 3, 8970. doi: 10.1039/C4TA04994B
16. [16]
  Hawash, Z.; Ono, L. K.; Raga, S. R.; Lee, M. V.; Qi, Y.-B. Chem. Mater. 2015, 27, 562. doi: 10.1021/cm504022q
17. [17]
  Leijtens, T.; Giovenzana, T.; Habisreutinger, S. N.; Tinkham, J. S.; Noel, N. K.; Kamino, B. A.; Sadoughi, G.; Sellinger, A.; Snaith, H. J. ACS Appl. Mater. Interfaces 2016, 8, 5981. doi: 10.1021/acsami.5b10093
18. [18]
  Zhang, L.-Z.; Zhou, X.-Y.; Zhong, X.-W.; Cheng, C.; Tian, Y.-Q.; Xu, B.-M. Nano Energy 2019, 57, 248. doi: 10.1016/j.nanoen.2018.12.033
19. [19]
  Li, X.-D.; Wang, Y.-C.; Zhu, L.-P.; Zhang, W.-J.; Wang, H.-Q.; Fang, J.-F. ACS Appl. Mater. Interfaces 2017, 9, 31357. doi: 10.1021/acsami.7b11977
20. [20]
  Sun, W.-H.; Li, Y.-L.; Yan, W.-B.; Peng, H.-T.; Ye, S.-Y.; Rao, H.-X.; Zhao, Z.-R. Liu, Z.-W. Bian, Z.-Q. Huang, C.-H. Chin. J. Chem. 2017, 35, 687. doi: 10.1002/cjoc.201600704
21. [21]
  Zhang, Z, -G.; Yang, Y.-K.; Yao, J.; Xue, L.-W.; Chen, S.-S.; Li, X.-J.; Morrison, W.; Yang, C.; Li, Y.-F. Angew. Chem., Int. Ed. 2017, 129, 13688. doi: 10.1002/ange.201707678
22. [22]
  Yan, W.-B.; Ye, S.-Y.; Li, Y.-L.; Sun, W.-H.; Rao, H.-X.; Liu, Z.-W.; Bian, Z.-Q.; Huang, C.-H. Adv. Energy Mater. 2016, 6, 1600474. doi: 10.1002/aenm.201600474
23. [23]
  Kim, Y. H.; Sachse, C.; Machala, M. L.; May, C.; Müller-Meskamp, L.; Leo, K. Adv. Funct. Mater. 2011, 21, 1076. doi: 10.1002/adfm.201002290
24. [24]
  Jeng, J.-Y.; Chen, K.-C.; Chiang, T.-Y.; Lin, P.-Y.; Tsai, T.-D.; Chang, Y.-C.; Guo, T.-F.; Chen, P.; Wen, T.-C.; Hsu, Y.-J. Adv. Mater. 2014, 26, 4107. doi: 10.1002/adma.201306217
25. [25]
  Kim, J. H.; Liang, P.-W.; Williams, S. T.; Cho, N.; Chueh, C.-C.; Glaz, M. S.; Ginger, D. S.; Jen, A. K. Y. Adv. Mater. 2015, 27, 695. doi: 10.1002/adma.201404189
26. [26]
  Lim, K.-G.; Kim, H.-B.; Jeong, J.; Kim, H.; Kim, J. Y.; Lee, T.-W. Adv. Mater. 2014, 26, 6461. doi: 10.1002/adma.201401775
27. [27]
  Girotto, C.; Moia, D.; Rand, B. P.; Heremans, P. Adv. Funct. Mater. 2011, 21, 64. doi: 10.1002/adfm.201001562
28. [28]
  Hou, F.-H.; Su, Z.-S.; Jin, F.-M.; Yan, X.-W.; Wang, L.-D.; Zhao, H.-F.; Zhu, J.-Z.; Chu, B.; Li, W.-L. Nanoscale 2015, 7, 9427. doi: 10.1039/C5NR01864A
29. [29]
  Nie, W.-Y.; Tsai, H.; Asadpour, R.; Blancon, J.; Neukirch, A. J.; Gupta1, G.; Crochet, J. J.; Chhowalla, M.; Tretiak, S.; Alam, M. A.; Wang, H.; Mohite, A. D. Science 2015, 347, 522. doi: 10.1126/science.aaa0472
30. [30]
  Zhou, H.-P.; Chen, Q.; Li, G.; Luo, S.; Song, T.; Duan, H.; Hong, Z.-R.; You, J.-B.; Liu, Y.-S.; Yang, Y. Science 2014, 345, 542. doi: 10.1126/science.1254050
31. [31]
  Li, Y.; Xu, Z.; Zhao, S.-L.; Qiao, B.; Huang, D.; Zhao, L.; Zhao, J.; Wang, P.; Zhu, Y.-Q.; Li, X.-G.; Liu, X.-C.; Xu, X.-R. Small 2016, 12, 4902. doi: 10.1002/smll.201601603
32. [32]
  Yang, L.-Y.; Cai, F.-L.; Yan, Y.; Li, J.-H.; Liu, D.; Pearson, A. J.; Wang, T. Adv. Funct. Mater. 2017, 27, 1702613. doi: 10.1002/adfm.201702613
33. [33]
  Huang, C.-Y.; Fu, W.-F.; Li, C.-Z.; Zhang, Z.-Q.; Qiu, W.-M.; Shi, M.-M.; Heremans, P.; Jen, A. K.-Y.; Chen, H.-Z. J. Am. Chem. Soc. 2016, 138, 2528. doi: 10.1021/jacs.6b00039
34. [34]
  Xue, R.-M.; Zhang, M.-Y.; Xu, G.-Y.; Zhang, J.-W.; Chen, W.-J.; Chen, H.-Y.; Yang, M.; Cui, C.-H.; Li, Y.-W.; Li, Y.-F. J. Mater. Chem. A 2018, 6, 404. doi: 10.1039/C7TA09716F
35. [35]
  Wang, J.-Y.; Liu, K.; Ma, L.-C.; Zhan, X.-W. Chem. Rev. 2016, 116, 14675. doi: 10.1021/acs.chemrev.6b00432
36. [36]
  Song, Z.-H.; Wang, S.-R.; Xiao, Y.; Li, X.-G. Acta Phys. Sin. 2015, 64, 033301(in Chinese). doi: 10.7498/aps.64.033301
37. [37]
  Zhang, H.; Wu, Y.-Z.; Zhang, W.-W.; Li, E.-P.; Shen, C.; Jiang, H.-Y.; Tian, H.; Zhu, W.-H. Chem. Sci. 2018, 9, 5919. doi: 10.1039/C8SC00731D
38. [38]
  Shen, C.; Wu, Y.-Z.; Zhang, H.; Li, E.-P.; Zhang, W.-W.; Xu, X.-J.; Wu, W.-J.; He, T.; Zhu, W.-H. Angew. Chem. Int. Ed. 2019, 58, 3784. doi: 10.1002/anie.201811593
39. [39]
  Urieta-Mora, J.; García-Benito, I.; Molina-Ontoria, A.; Martín, N. Chem. Soc. Rev. 2018, 47, 8541. doi: 10.1039/C8CS00262B
40. [40]
  Li, H.-R.; Fu, K.-W.; Hagfeldt, A.; Grätzel, M.; Mhaisalkar, S. G.; Grimsdale, A. C. Angew. Chem. Int. Ed. 2014, 53, 4169.
41. [41]
  Yang, D.; Sano, T.; Yaguchi, Y.; Sun, H.; Sasabe, H.; Kido, J. Adv. Funct. Mater. 2018, 29, 1807556.
42. [42]
  Bi, C.; Wang, Q.; Shao, Y.-C.; Yuan, Y.-B.; Xiao, Z.-G.; Huang, J.-S. Nat. Commun. 2015, 6, 7747. doi: 10.1038/ncomms8747
43. [43]
  Yu, H.-Z. Acta Phys. Sin. 2012, 61, 087204(in Chinese). doi: 10.7498/aps.61.087204
44. [44]
  Davey, M. H.; Lee, V. Y.; Miller, R. D.; Marks, T. J. J. Org. Chem. 1999, 64, 4976. doi: 10.1021/jo990235x
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