Citation: Yi-kun Guo, Da-hui Zhao. New Perylenediimide Polymer Acceptor Design and Their Applications to All-polymer Solar Cells[J]. Acta Polymerica Sinica, ;2018, (2): 174-185. doi: 10.11777/j.issn1000-3304.2018.17268 shu

New Perylenediimide Polymer Acceptor Design and Their Applications to All-polymer Solar Cells

Yi-kun Guo ,
Da-hui Zhao ^,

College of Chemistry and Molecular Engineering, Peking University, Beijing 100871

Corresponding author: Da-hui Zhao, dhzhao@pku.edu.cn
Received Date: 18 September 2017
Revised Date: 23 October 2017

Bulk-heterojunction (BHJ) polymer solar cells (PSCs) have attracted attention over the past decades due to their distinct advantages of low cost, light weight, and the suitability for flexible-device fabrications. Despite the remarkable success in improving the efficiency of PSCs, fullerene-based acceptors have shown evident limitations. Accordingly, increased research efforts have been invested in developing non-fullerene acceptors, and great development has been witnessed in this field in recent years. Among all different kinds of BHJ PSCs, all polymer solar cells (all-PSCs) potentially possess the most stable donor-acceptor phase separation morphology, and all-polymer films are expected to boast superior mechanical properties. Yet, the bottle neck of enhancing the power conversion efficiency (PCE) of all-PSCs currently lies in the performance of the polymer acceptors. In the past years, we have been focusing on designing new polymer acceptors using perylenediimide (PDI) as the main building block and studying their performance in all-PSCs. A series of PDI-based polymer acceptors have been synthesized and studied since 2013. Due to the steric hindrance induced by the bay-region substitution, the PDI polymers mostly manifest low crystallinity. Accordingly, by enhancing the conjugation and rigidity of the polymer backbone, and thereby improving the aggregation and crystallization ability of the polymers, increased PCE has been achieved with all-PSC devices. Consistently, experimental evidence has also been collected showing improved morphology of the active layer. As a result of the continued and systematic studies on designing and synthesizing new polymer acceptors, along with the optimization of device fabrication conditions, the best PCE of all-PSC incorporating a PDI polymer acceptor has now been boosted to 8.59%. Very similar PCE values can be obtained from devices fabricated under ambient conditions, proving the high chemo-stability of the active-layer materials. The synthetic methods of these PDI-based polymers and the device fabrication conditions are much more convenient and economical. All these properties are friendly to the large-scale material preparation and device production.
- All-polymer solar cells,
- Perylenediimide polymer acceptors,
- Power conversion efficiency
1. [1]
  Facchetti A. Mater Today, 2015, 16:123-132
2. [2]
  Halls J J M, Walsh C A, Greenham N C, Marseglia E A, Friend R H, Moratti S C, Holmes A B. Nature, 1995, 376:498-500 doi: 10.1038/376498a0
3. [3]
  Long X, Ding Z, Dou C, Zhang J, Liu, J, Wang L. Adv Mater, 2016, 28:6504-6508 doi: 10.1002/adma.201601205
4. [4]
  Li Z, Xu X, Zhang W, Meng X, Ma W, Yartsev A, Inganäs O, Andersson M R, Janssen R A J, Wang E. J Am Chem Soc, 2016, 138:10935-10944 doi: 10.1021/jacs.6b04822
5. [5]
  Hwang Y J, Courtright B A E, Ferreira A S, Tolbert S H, Jenekhe S A. Adv Mater, 2015, 27:4578-4584 doi: 10.1002/adma.v27.31
6. [6]
  Lee C, Kang H, Lee W, Kim T, Kim K H, Woo H Y, Wang C, Kim B J. Adv Mater, 2015, 27:2466-2471 doi: 10.1002/adma.201405226
7. [7]
  Mori D, Benten H, Okada I, Ohkita H, Ito S. Energy Environ Sci, 2014, 7:2939-2943 doi: 10.1039/C4EE01326C
8. [8]
  Kim T, Kim J H, Kang T E, Lee C, Kang H, Shin M, Wang C, Ma B, Jeong U, Kim T S, Kim B J. Nat Commun, 2015, 6:8547
9. [9]
  Gao L, Zhang Z, Xue L, Min J, Zhang J, Wei Z, Li Y. Adv Mater, 2016, 28:1884-1890 doi: 10.1002/adma.201504629
10. [10]
  Fan B, Ying L, Wang Z, He B, Jian X F, Huang F, Cao Y. Energy Environ Sci, 2017, 10:1243-1251 doi: 10.1039/C7EE00619E
11. [11]
  Jung J W, Jo J W, Chueh C C, Liu F, Jo W H, Russell T P, Jen A K Y. Adv Mater, 2015, 27:3310-3317 doi: 10.1002/adma.v27.21
12. [12]
  Lv L, Wang X, Wang X, Yang L, Dong T, Yang Z, Huang H. ACS Appl Mater Interfaces, 2016, 8:34620-34629
13. [13]
  Zhan X, Tan Z A, Domercq B, An Z, Zhang X, Barlow S, Li Y, Zhu D, Kippelen B, Marder S R. J Am Chem Soc, 2007, 129:7246-7247
14. [14]
  Zhou E, Cong J, Wei Q, Tajima K, Yang C, Hashimoto K. Angew Chem Int Ed, 2011, 50:2799-2803 doi: 10.1002/anie.201005408
15. [15]
  Fukutomi Y, Nakano M, Hu J, Osaka I, TakimiyaK. J Am Chem Soc, 2013, 135:11445-11448 doi: 10.1021/ja404753r
16. [16]
  Yang J, Xiao B, Tajima K, Nakano M, Takimiya K, Tang A, Zhou E. Macromolecules, 2017, 50:3179-3185 doi: 10.1021/acs.macromol.7b00414
17. [17]
  Dou C, Ding Z, Zhang X, Liu J, Wang L. Angew Chem Int Ed, 2015, 54:3648-3652 doi: 10.1002/anie.201411973
18. [18]
  Long X, Ding Z, Dou C, Zhang J, Liu J, Wang L. Adv Mater, 2016, 28:6504-6508 doi: 10.1002/adma.201601205
19. [19]
  Zhang Z, Yang Y, Yao J, Xue L, Chen S, Li X, Morrison W, Yang C, Li Y. Angew Chem Int Ed, 2017, 56:13503-13507
20. [20]
  Benten H, Mori D, Ohkita H, Ito S. J Mater Chem A, 2016, 4:5340-5365 doi: 10.1039/C5TA10759H
21. [21]
  Zhan C, Yao J. Chem Mater, 2016, 28:1948-1964
22. [22]
  Zhong Y, Trinh M T, Chen R, Purdum G E, Khlyabich P P, Sezen M, Oh S, Zhu H, Fowler B, Zhang B, Wang W, Nam C Y, Sfeir M Y, Black C T, Steigerwald M L, Loo Y L, Ng F, Zhu X Y, Nuckolls C. Nat Commun, 2015, 6:8242 doi: 10.1038/ncomms9242
23. [23]
  Wu Q, Zhao D, Schneider A M, Chen W, Yu L. J Am Chem Soc, 2016, 138:4698-4705
24. [24]
  Zhang A, Li C, Yand F, Zhang K, Wang Z, Wei Z, Li W. Angew Chem Int Ed, 2017, 56:2694-2698 doi: 10.1002/anie.201612090
25. [25]
  Yang L, Chen Y, Chen S, Dong T, Deng W, Lv L, Yang S, Yan H, Huang H. J Power Sources, 2016, 324:538-546 doi: 10.1016/j.jpowsour.2016.05.119
26. [26]
  Yan Q, Zhou Y, Zheng Y, Pei J, Zhao D. Chem Sci, 2013, 4:4389-4394
27. [27]
  Meng, D, Fu H, Xiao C, Meng X, Winands T, Ma W, Wei W, Fan B, Huo L, Doltsinis N L, Li Y, Sun Y, Wang Z. J Am Chem Soc, 2016, 138:10184-10190 doi: 10.1021/jacs.6b04368
28. [28]
  Meng D, Sun D, Zhong C, Liu T, Fan B, Huo L, Li Y, Jiang W, Choi H, Kim T, Kim J Y, Sun Y, Wang Z, Heeger A J. J Am Chem Soc, 2016, 138:375-380 doi: 10.1021/jacs.5b11149
29. [29]
  Hwang Y, Li H, Courtright B A E, Subramaniyan S, Jenekhe S A. Adv Mater, 2016, 28:124-131 doi: 10.1002/adma.201503801
30. [30]
  Zhao J, Li Y, Lin H, Liu Y, Jiang K, Mu C, Ma T, Lai J Y L, Hu H, Yu D, Yan H. Energy Environ Sci, 2015, 8:520-525
31. [31]
  Liu J, Chen S, Qian D, Gautam B, Yang G, Zhao J, Bergqvist J, Zhang F, Ma W, Inganäs O, Gundogdu K, Gao F, Yan H. Nature Energy, 2016, 1:16089
32. [32]
  Zhang X, Zhang C, Zhang X, Yao J. Tetrahedron, 2013, 69:8155-8160 doi: 10.1016/j.tet.2013.07.035
33. [33]
  Zhou Y, Yan Q, Zheng Y, Wang J, Zhao D, Pei J. J Mater Chem A, 2013, 1:6609-6613 doi: 10.1039/c3ta10864c
34. [34]
  Zhou Y, Kurosawa T, Ma W, Guo Y, Fang L, Vandewal K, Diao Y, Wang C, Yan Q, Reinspach J, Mei J, Appleton A L, Koleilat G I, Gao Y, Mannsfeld S C B, Salleo A, Ade H, Zhao D, Bao Z. Adv Mater, 2014, 26:3767-3772 doi: 10.1002/adma.v26.22
35. [35]
  Zhou Y, Gu K L, Gu X, Kurosawa T, Yan H, Guo Y, Koleilat G I, Zhao D, Toney M F, Bao Z. Chem Mater, 2016, 28:5037-5042 doi: 10.1021/acs.chemmater.6b01776
36. [36]
  Li S, Zhang H, Zhao W, Ye L, Yao H, Yang B, Zhang S, Hou J. Adv Energy Mater, 2016, 6:1501991
37. [37]
  Guo Y, Li Y, Han H, Yan H, Zhao D. Chinese J Polym Sci, 2017, 35:293-301
38. [38]
  Guo Y, Li Y, Awartani O, Zhao J, Han H, Ade H, Zhao D, Yan H. Adv Mater, 2016, 28:8483-8489 doi: 10.1002/adma.v28.38
39. [39]
  Diao Y, Zhou Y, Kurosawa T, Shaw L, Wang C, Park S, Guo Y, Reinspach J A, Gu K, Gu X, Tee B C K, Pang C, Yan H, Zhao D, Toney M F, Mannsfeld S C B, Bao Z. Nat Commun, 2015, 6:7955 doi: 10.1038/ncomms8955
40. [40]
  Gu X, Zhou Y, Gu K, Kurosawa T, Guo Y, Li Y, Lin H, Schroeder B, Yan H, Molina-Lopez F, Tassone C, Wang C, Mannsfeld S, Zhao D, Toney M, Bao Z. Adv Energy Mater, 2017, 7:1602742 doi: 10.1002/aenm.201602742
41. [41]
  Guo Y, Li Y, Awartani O, Han H, Zhang G, Ade H, Yan H, Zhao D. Mater Chem Front, 2017, 1:1362-1368
42. [42]
  Guo Y, Li Y, Awartani O, Han H, Zhao J, Ade H, Yan H, Zhao D. Adv Mater, 2017, 29:1700309 doi: 10.1002/adma.201700309
1. [1]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 100027-0. doi: 10.3866/PKU.WHXB202406007
2. [2]
  Binbin Liu , Yang Chen , Tianci Jia , Chen Chen , Zhanghao Wu , Yuhui Liu , Yuhang Zhai , Tianshu Ma , Changlei Wang . Hydroxyl-functionalized molecular engineering mitigates 2D phase barriers for efficient wide-bandgap and all-perovskite tandem solar cells. Acta Physico-Chimica Sinica, 2026, 42(1): 100128-0. doi: 10.1016/j.actphy.2025.100128
3. [3]
  Ruonan Li , Shijie Liang , Yunhua Xu , Cuifen Zhang , Zheng Tang , Baiqiao Liu , Weiwei Li . Chlorine-Substituted Double-Cable Conjugated Polymers with Near-Infrared Absorption for Low Energy Loss Single-Component Organic Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(8): 2307037-0. doi: 10.3866/PKU.WHXB202307037
4. [4]
  Jiatong Hu , Qiyi Wang , Ruiwen Tang , Jiajing Feng . Photocatalytic Journey of Perylene Diimides in a Competitive Arena. University Chemistry, 2025, 40(5): 328-333. doi: 10.12461/PKU.DXHX202407015
5. [5]
  Zhen FAN , Jiayan WANG , Wenhao ZHU , Xiuchun ZHANG , Yang WANG , Hao LI , Zeyuan WANG , Songzhi ZHENG , Weihai SUN . Fabrication of CsPbBr₃ perovskite solar cells using buried polyvinylidene fluorideinterface modification method. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2464-2478. doi: 10.11862/CJIC.20250191
6. [6]
  Chuan′an DING , Weibo YAN , Shaoying WANG , Hao XIN . Preparation of wide-band gap copper indium gallium sulfide solar cells by solution method. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1755-1764. doi: 10.11862/CJIC.20250198
7. [7]
  Fengying Zhang , Yanglin Mei , Yuman Jiang , Shenshen Zheng , Kaibo Zheng , Ying Zhou . Research progress of transient absorption spectroscopy in solar energy conversion and utilization. Acta Physico-Chimica Sinica, 2025, 41(9): 100118-0. doi: 10.1016/j.actphy.2025.100118
8. [8]
  Yixuan Gao , Lingxing Zan , Wenlin Zhang , Qingbo Wei . Comprehensive Innovation Experiment: Preparation and Characterization of Carbon-based Perovskite Solar Cells. University Chemistry, 2024, 39(4): 178-183. doi: 10.3866/PKU.DXHX202311091
9. [9]
  Nengmin ZHU , Wenhao ZHU , Xiaoyao YIN , Songzhi ZHENG , Hao LI , Zeyuan WANG , Wenhao WEI , Xuanheng CHEN , Weihai SUN . Preparation of high-performance CsPbBr₃ perovskite solar cells by the aqueous solution solvent method. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1131-1140. doi: 10.11862/CJIC.20240419
10. [10]
  Yameen Ahmed , Xiangxiang Feng , Yuanji Gao , Yang Ding , Caoyu Long , Mustafa Haider , Hengyue Li , Zhuan Li , Shicheng Huang , Makhsud I. Saidaminov , Junliang Yang . Interface Modification by Ionic Liquid for Efficient and Stable FAPbI₃ Perovskite Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(6): 2303057-0. doi: 10.3866/PKU.WHXB202303057
11. [11]
  Yawen Guo , Dawei Li , Yang Gao , Cuihong Li . Recent Progress on Stability of Organic Solar Cells Based on Non-Fullerene Acceptors. Acta Physico-Chimica Sinica, 2024, 40(6): 2306050-0. doi: 10.3866/PKU.WHXB202306050
12. [12]
  Zongsheng LI , Yichao WANG , Yujie WANG , Wenhao ZHU , Xiaoyao YIN , Wudan YANG , Songzhi ZHENG , Weihai SUN . Preparation of CsPbBr₃ perovskite solar cells via bottom interface modification with methylammonium chloride. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1805-1816. doi: 10.11862/CJIC.20250066
13. [13]
  Pengyu Dong , Yue Jiang , Zhengchi Yang , Licheng Liu , Gu Li , Xinyang Wen , Zhen Wang , Xinbo Shi , Guofu Zhou , Jun-Ming Liu , Jinwei Gao . NbSe₂ Nanosheets Improved the Buried Interface for Perovskite Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 100029-0. doi: 10.3866/PKU.WHXB202407025
14. [14]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
15. [15]
  Zeyuan WANG , Songzhi ZHENG , Hao LI , Jingbo WENG , Wei WANG , Yang WANG , Weihai SUN . Effect of I₂ interface modification engineering on the performance of all-inorganic CsPbBr₃ perovskite solar cells. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1290-1300. doi: 10.11862/CJIC.20240021
16. [16]
  Yipeng Zhou , Chenxin Ran , Zhongbin Wu . Metacognitive Enhancement in Diversifying Ideological and Political Education within Graduate Course: A Case Study on “Solar Cell Performance Enhancement Technology”. University Chemistry, 2024, 39(6): 151-159. doi: 10.3866/PKU.DXHX202312096
17. [17]
  Xiaoyao YIN , Wenhao ZHU , Puyao SHI , Zongsheng LI , Yichao WANG , Nengmin ZHU , Yang WANG , Weihai SUN . Fabrication of all-inorganic CsPbBr₃ perovskite solar cells with SnCl₂ interface modification. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 469-479. doi: 10.11862/CJIC.20240309
18. [18]
  Mingxuan Qi , Lanyu Jin , Honghe Yao , Zipeng Xu , Teng Cheng , Qi Chen , Cheng Zhu , Yang Bai . Recent progress on electrical failure and stability of perovskite solar cells under reverse bias. Acta Physico-Chimica Sinica, 2025, 41(8): 100088-0. doi: 10.1016/j.actphy.2025.100088
19. [19]
  Ying Liang , Yuheng Deng , Shilv Yu , Jiahao Cheng , Jiawei Song , Jun Yao , Yichen Yang , Wanlei Zhang , Wenjing Zhou , Xin Zhang , Wenjian Shen , Guijie Liang , Bin Li , Yong Peng , Run Hu , Wangnan Li . Machine learning-guided antireflection coatings architectures and interface modification for synergistically optimizing efficient and stable perovskite solar cells. Acta Physico-Chimica Sinica, 2025, 41(9): 100098-0. doi: 10.1016/j.actphy.2025.100098
20. [20]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . Accelerated Interfacial Electron Transfer in Perovskite Solar Cell by Ammonium Hexachlorostannate Modification and fs-TAS Investigation. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-0. doi: 10.3866/PKU.WHXB202402006

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(178)
HTML views(9)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142