Abstract
The quaternized conjugated polymer based on poly[(9,9-bis(3′-(N,N-dimethylamino)propyl)-2,7-fluorene)-alt-2,7-(9,9-dihexylfluorene)] (PFN) as cathode interlayer material (CIM) in a polymer solar cell was systematically investigated. The interlayer consists of alternating dihexyl fluorene and dimethyl aminopropyl fluorene backbone. The corresponding quaternized conjugated polyelectrolytes, named PFN salt and PFN-OH salt, were synthesized by introducing quaternized agents, such as bromoethane or bromoethanol, as side chains onto the PFN precursor polymer. Different quaternized agents give the different inducing effects of an interfacial dipole. The structure of inverted polymer solar cells (iPSCs) is ZnO/interlayer/PTB7-Th:PC71BM/MoO3/Ag. The enhancement in the efficiency of the iPSCs was accomplished by introducing a PFN, PFN salt, and PFN-OH salt as the CIM. Modification of side-chain functionality with bromoethanol shows better performances than that with bromoethane as an interlayer.
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References
Y. Li, Acc. Chem. Res., 45, 723 (2012).
W. Zhang, Y. Wu, Q. Bao, F. Gao, and J. Fang, Adv. Energy Mater., 4 (2014).
S. L. Handoko, H. C. Jin, D. R. Whang, J. H. Kim, and D. W. Chang, J. Ind. Eng. Chem., 86, 244 (2020).
S. L. Handoko, H. C. Jin, D. R. Whang, S. K. Putri, J. H. Kim, and D. W. Chang, J. Ind. Eng. Chem., 73, 192 (2019).
X. Li, X. Liu, W. Zhang, H. Q. Wang, and J. Fang, Chem. Mater., 29, 4176 (2017).
Z. Wu, C. Sun, S. Dong, X. F. Jiang, S. Wu, H. Wu, H. L. Yip, F. Huang, and Y. Cao, J. Am. Chem. Soc., 138, 2004 (2016).
M. Lv, S. Li, J. J. Jasieniak, J. Hou, J. Zhu, Z. Tan, S. E. Watkins, Y. Li, and X. Chen, Adv. Mater., 25, 6889 (2013).
B. C. J. Brabec, A. Cravino, D. Meissner, N. S. Sariciftci, T. Fromherz, M. T. Rispens, L. Sanchez, and J. C. Hummelen, Adv. Funct. Mater., 11, 374 (2001).
S. S. Reddy, U. K. Aryal, H. Jin, T. Gokulnath, D. G. Rajalapati, K. Kranthiraja, S. T. Shin, and S. H. Jin, Macromol. Res., 28, 179 (2020).
S. Lee, J. W. Ha, H. J. Park, and D. H. Hwang, Macromol. Res., 903 (2020).
H. Cha, J. Li, Y. Li, S.-O. Kim, Y.-H. Kim, and S.-K. Kwon, Macromol. Res., 28, 820 (2020).
E. R. Rwenyagila, Int. J. Photoenergy, 2017, 1 (2017).
L. J. A. Koster, E. C. P. Smits, V. D. Mihailetchi, and P. W. M. Blom, Phys. Rev. B, 72, 085205 (2005).
G. Yu, J. Gao, J. C. Hummelen, F. Wudl, and A. J. Heeger, Science (80-.)., 270, 1789 (1995).
Abdullah, M. S. Akhtar, E. B. Kim, L. Fijahi, H. S. Shin, and S. Ameen, J. Ind. Eng. Chem., 81, 309 (2020).
Y. J. Cheng, S. H. Yang, and C. S. Hsu, Chem. Rev., 109, 5868 (2009).
K. Bini, X. Xu, M. R. Andersson, and E. Wang, ACS Appl. Energy Mater., 1, 2176 (2018).
C. E. Song, K. Y. Ryu, S. J. Hong, C. Bathula, S. K. Lee, W. S. Shin, J. C. Lee, S. K. Choi, J. H. Kim, et al., ChemSusChem, 6, 1445 (2013).
L. Chua, J. Zaumseil, J. Chang, and E. C. Ou, Nature, 434, 194 (2005).
Y. J. Cheng, C. H. Hsieh, Y. He, C. S. Hsu, and Y. Li, J. Am. Chem. Soc., 132, 17381 (2010).
Y. Sun, J. H. Seo, C. J. Takacs, J. Seifter, and A. J. Heeger, Adv. Mater., 23, 1679 (2011).
C. Duan, K. Zhang, C. Zhong, F. Huang, and Y. Cao, Chem Soc Rev, 42, 9071 (2013).
C. Chueh, C. Li, and A. K. Jen, energy and, 8, 1160 (Royal Society of Chemistry, 2015).
H. Yip and A. K. Jen, Energy Environ. Sci., 5, 5994 (2012).
T. T. Do, H. S. Hong, Y. E. Ha, S. Il Yoo, Y. S. Won, M. J. Moon, and J. H. Kim, Macromol. Res., 23, 367 (2015).
R. Kang, S. H. Oh, and D. Y. Kim, ACS Appl. Mater. Interfaces, 6, 6227 (2014).
G. Li, R. Zhu, and Y. Yang, Nat. Photonics, 6, 153 (Nature Publishing Group, 2012).
Z. He, C. Zhong, X. Huang, W. Wong, and H. Wu, Adv. Mater., 23, 4636 (2011).
L. Zhang, C. Liu, T. Lai, H. Huang, X. Peng, and F. Huang, J. Mater. Chem. A, 4, 15156 (Royal Society of Chemistry, 2016).
Y. L. Li, Y. S. Cheng, P. N. Yeh, S. H. Liao, and S. A. Chen, Adv. Funct. Mater., 24, 6811 (2014).
Y. Liu, Z. A. Page, T. P. Russell, and T. Emrick, Angew. Chemie — Int. Ed., 54, 11485 (2015).
J. H. Seo, A. Gutacker, Y. Sun, H. Wu, F. Huang, Y. Cao, U. Scherf, A. J. Heeger, and G. C. Bazan, J. Am. Chem. Soc., 133, 8416 (2011).
M. Jeong, H. C. Jin, D. K. Moon, and J. H. Kim, Adv. Mater. Interfaces, 1900797, 1 (2019).
M. Jeong, H. C. Jin, J. H. Lee, D. K. Moon, and J. H. Kim, Dye. Pigment., 173, 107927 (2020).
Z. G. Zhang, B. Qi, Z. Jin, D. Chi, Z. Qi, Y. Li, and J. Wang, Energy Environ. Sci., 7, 1966 (2014).
F. Huang, L. Hou, H. Shen, J. Jiang, F. Wang, H. Zhen, and Y. Cao, J. Mater. Chem., 15, 2499 (2005).
F. Huang, H. Wu, D. Wang, W. Yang, and Y. Cao, Chem. Mater., 16, 708 (2004).
F. Huang, H. Wu, J. Peng, W. Yang, and Y. Cao, Curr. Org. Chem., 11, 1207 (2007).
K. Zilberberg, A. Behrendt, M. Kraft, U. Scherf, and T. Riedl, Org. Electron., 14, 951 (2013).
K. Bini, X. Xu, M. R. Andersson, and E. Wang, research-article, ACS Appl. Energy Mater., 1, 2176 (American Chemical Society, 2018).
Z. He, H. Wu, and Y. Cao, Adv. Mater., 26, 1006 (2014).
Y. Zhou, C. Fuentes-Hernandez, J. Shim, J. Meyer, A. J. Giordano, H. Li, P. Winget, T. Papadopoulos, H. Cheun, et al., Science (80-.)., 336, 327 (American Association for the Advancement of Science, 2012).
S. Van Reenen, S. Kouijzer, R. A. J. Janssen, M. M. Wienk, and M. Kemerink, Adv. Mater Interfaces, 1, 1 (2014).
C. Wang, Y. Luo, J. Zheng, L. Liu, Z. Xie, F. Huang, B. Yang, and Y. Ma, ACS Appl. Mater. Interfaces, 10, 10270 (2018).
K. G. Lim, S. M. Park, H. Y. Woo, and T. W. Lee, ChemSusChem, 8, 3062 (2015).
Z. Hu, K. Zhang, F. Huang, and Y. Cao, Chem. Commun., 51, 5572 (Royal Society of Chemistry, 2015).
E. L. Ratcliff, B. Zacher, and N. R. Armstrong, J. Phys. Chem. Lett., 2, 1337 (2011).
J. Park, R. Yang, C. V. Hoven, A. Garcia, D. A. Fischer, T. Q. Nguyen, G. C. Bazan, and D. M. Delongchamp, Adv. Mater., 20, 2491 (2008).
M. Y. Jo, T. T. Do, Y. E. Ha, Y. S. Won, and J. H. Kim, Org. Electron., 16, 18 (Elsevier B.V., 2015).
M. Y. Jo, Y. E. Ha, Y. S. Won, S. Il Yoo, and J. H. Kim, Org. Electron., 25, 85 (Elsevier B.V., 2015).
S. M. SZE, Solutions Manual — Semiconductor devices physics and technoloy (John Wiley and Sons, Inc, New York, 1981).
C. Waldauf, M. C. Scharber, P. Schilinsky, J. A. Hauch, and C. J. Brabec, J. Appl. Phys., 99 (2006).
C. He, C. Zhong, H. Wu, R. Yang, W. Yang, F. Huang, G. C. Bazan, and Y. Cao, J. Mater. Chem., 20, 2617 (2010).
X. Jia, Z. Jiang, X. Chen, J. Zhou, L. Pan, F. Zhu, Z. Sun, and S. Huang, ACS Appl. Mater. Interfaces, 8, 3792 (2016).
H. C. Jin, S. A. Salma, D. K. Moon, and J. H. Kim, J. Mater. Chem. A, 8, 4562 (Royal Society of Chemistry, 2020).
F. Yang, Y. Xu, M. Gu, S. Zhou, Y. Wang, K. Lu, Z. Liu, X. Ling, Z. Zhu, et al., J. Mater. Chem. A, 6, 17688 (Royal Society of Chemistry, 2018).
R. Azmi, S. H. Oh, and S. Y. Jang, ACS Energy Lett., 1, 100 (2016).
A. Gusain, R. M. Faria, and P. B. Miranda, Front. Chem., 7, 61 (2019).
L. J. A. Koster, V. D. Mihailetchi, R. Ramaker, and P. W. M. Blom, Appl. Phys. Lett., 86, 1 (2005).
C. Sun, F. Pan, S. Chen, R. Wang, R. Sun, Z. Shang, B. Qiu, J. Min, M. Lv, et al., Adv. Mater., 31, 1 (2019).
S. Nho, G. Baek, S. Park, B. R. Lee, M. J. Cha, D. C. Lim, J. H. Seo, S. H. Oh, M. H. Song, et al., Energy Environ. Sci., 9, 240 (Royal Society of Chemistry, 2016).
H. Liu, L. Huang, X. Cheng, A. Hu, H. Xu, L. Chen, and Y. Chen, ACS Appl. Mater. Interfaces, 9, 1145 (2017).
Y. Li, X. Li, X. Liu, L. Zhu, W. Zhang, and J. Fang, J. Phys. Chem. C, 120, 26244 (2016).
K. Rainer, R. Sastrawan, J. Ferber, R. Stangl, and J. Luther, Electrochim. Acta, 4213 (2002).
K. V. Sankar and R. K. Selvan, RSC Adv., 4, 17555 (2014).
Q. Qu, P. Zhang, B. Wang, Y. Chen, S. Tian, Y. Wu, and R. Holze, J. Phys. Chem. C, 113, 14020 (2009).
Y. Huang, Y. Li, Z. Hu, G. Wei, J. Guo, and J. Liu, J. Mater. Chem. A, 1, 9809 (2013).
H. Toyohisa, K. Ryuji, S. Kazunari, and E. Koichi, Electrochemistry, 70, 675 (2002).
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Acknowledgment: This research was supported by the Korea Institute of Energy Technology Evaluation and Planning (2018201010636A), the National Research Foundation (NRF) of Korea under the program number 2019R1A2C1002585, and the BB21 Project in 2021.
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Salma, S.A., Kim, J.H. Effect of the Side Chain Functionality of the Conjugated Polyelectrolytes as a Cathode Interlayer Material on the Photovoltaic Performances. Macromol. Res. 30, 146–151 (2022). https://doi.org/10.1007/s13233-022-0011-2
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DOI: https://doi.org/10.1007/s13233-022-0011-2