Citation: Xiao-peng Xu, Guang-jun Zhang, Yun-zhe Zhao, Jiang Liu, Ying Li, Qiang Peng. Highly Efficient Random Terpolymers for Photovoltaic Applications with Enhanced Absorption and Molecular Aggregation[J]. Chinese Journal of Polymer Science, ;2017, 35(2): 249-260. doi: 10.1007/s10118-017-1877-x shu

Highly Efficient Random Terpolymers for Photovoltaic Applications with Enhanced Absorption and Molecular Aggregation

a.
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, State Key Laboratory of Polymer Materials Engineering, Sichuan University, Chengdu 610064, China
b.
Chengdu Green Energy and Green Manufacturing Technology R & D Center, Chengdu 610207, China

Corresponding author: Jiang Liu, 546jiang@163.com Qiang Peng, qiangpengjohnny@yahoo.com
Received Date: 20 August 2016
Revised Date: 18 September 2016
Accepted Date: 20 September 2016

Fund Project: the Youth Science and Technology Foundation of Sichuan Province 2013JQ0032the National Natural Science Foundation of China 21432005the Synergistic Innovation Joint Foundation of CAEP-SCU XTCX2014008the National Natural Science Foundation of China 51573107the Fundamental Research Funds for the Central Universities 2012SCU04B01the Foundation of State Key Laboratory of Polymer Materials Engineering sklpme2014-3-05the Fundamental Research Funds for the Central Universities YJ2011025

A series of copolymers, based on benzo[1, 2-b:4, 5-b']dithiophene (BDT) as the electron donor and 2, 1, 3-benzothiadiazole (BT)/diketopyrrolo[3, 4-c]pyrrole (DPP) as the electron acceptors, were synthesized for highly efficient polymer solar cells. By changing the BT/DPP ratio in the conjugated backbone, the absorption, energy levels, molecular aggregation and carrier mobility could be finely tuned. With increased DPP content, the absorption range was extended to the longer wavelength region with narrower bandgaps. The highest occupied molecular orbital (HOMO) levels were also raised up and the molecular aggregation was enhanced. The balance of these factors would afford a remarkable device performance enhancement. Polymer P3 with BT:DPP=0.7:0.3 (molar ratio) exhibited the highest power conversion efficiency (PCE) of 9.01%, with open circuit voltage (V_oc)=0.73 V, short current density (J_sc)=18.45 mA·cm^-2, and fill factor (FF)=66.9%. The PCE value was improved by 48.7% compared to P1 and by 117.6% compared to P7, respectively, indicating a great potential in photovoltaic application.
- Polymer solar cells,
- Terpolymers,
- Complementary absorption,
- Molecular aggregation
1. [1]
  Chen, J.W. and Cao, Y., Acc. Chem. Res., 2009, 42:1709 doi: 10.1021/ar900061z
2. [2]
  Lu, L.Y. and Yu, L.P., Adv. Mater., 2014, 26:4413 doi: 10.1002/adma.v26.26
3. [3]
  Thompson, B.C. and Fréchet, J.M.J., Angew. Chem. Int. Ed., 2008, 47:58 doi: 10.1002/(ISSN)1521-3773
4. [4]
  Li, Y.F., Acc. Chem. Res., 2012, 45:723 doi: 10.1021/ar2002446
5. [5]
  Zhao, J.B., Li, Y., Yang, G.F., Jiang, K., Lin, H.R., Ade, H., Ma, W. and Yan, H., Nat. Energy, 2016, 1:15027 doi: 10.1038/nenergy.2015.27
6. [6]
  Yang, Y., Chen, W., Dou, L.T., Chang, W.H., Duan, H.S., Bob, B., Li, G. and Yang, Y., Nat. Photon., 2015, 9:190 doi: 10.1038/nphoton.2015.9
7. [7]
  Jiang, J.M., Chen, H.C., Lin, H.K., Yu, C.M., Lan, S.C., Liu, C.M. and Wei, K.H., Polym. Chem., 2013, 4:5321 doi: 10.1039/c3py00132f
8. [8]
  Li, K., Li, Z.J., Feng, K., Xu, X.P., Wang, L.Y. and Peng, Q., J. Am. Chem. Soc., 2013, 135:13549 doi: 10.1021/ja406220a
9. [9]
  Kim, J.Y., Lee, K., Coates, N.E., Moses, D., Nguyen, T.Q., Dante, M. and Heeger, A.J., Science, 2007, 317:222 doi: 10.1126/science.1141711
10. [10]
  Yusoff, A.R.B.M., Kim, D., Kim, H.P., Shneider, F.K., Da Silva, W.J. and Jang, J., Energy Environ. Sci., 2015, 8:303 doi: 10.1039/C4EE03048F
11. [11]
  Zheng, Z., Zhang, S.Q., Zhang, M.J., Zhao, K., Ye, L., Chen, Y., Yang, B. and Hou, J.H., Adv. Mater., 2015, 27:1189 doi: 10.1002/adma.201404525
12. [12]
  Zhang, K., Gao, K., Xia, R., Wu, Z., Sun, C., Cao, J., Qian, L., Li, W., Liu, S., Huang, F., Peng, X., Ding, L., Yip, H.L. and Cao, Y., Adv. Mater., 2016, 28:4817 doi: 10.1002/adma.v28.24
13. [13]
  Jung, J.W., Liu, F., Russell, T.P. and Jo, W.H., Energy Environ. Sci., 2013, 6:3301 doi: 10.1039/c3ee40689j
14. [14]
  Liu, S.H., You, P., Li, J., Li, J., Lee, C.S., Ong, B.S., Surya, C. and Yan, F., Energy Environ. Sci., 2015, 8:1463 doi: 10.1039/C5EE00090D
15. [15]
  Lu, L.Y., Xu, T., Chen, W., Landry, E.S. and Yu, L.P., Nat. Photon., 2014, 8:716 doi: 10.1038/nphoton.2014.172
16. [16]
  Lu, L.Y., Chen, W., Xu, T. and Yu, L.P., Nat. Commun., 2015, 6:7327 doi: 10.1038/ncomms8327
17. [17]
  Xu, X.P., Li, Z.J., Wang, Z.G., Li, K., Feng, K. and Peng, Q., Nano Energy, 2016, 25:170 doi: 10.1016/j.nanoen.2016.04.048
18. [18]
  Gasparini, N., Salvador, M., Fladischer, S., Katsouras, A., Avgeropoulos, A., Spiecker, E., Chochos, C.L., Brabec, C.J. and Ameri, T., Adv. Energy Mater., 2015, 5:1501527 doi: 10.1002/aenm.201501527
19. [19]
  Cheng, P., Li, Y.F. and Zhan, X.W., Energy Environ. Sci., 2014, 7:2005 doi: 10.1039/c3ee44202k
20. [20]
  Zhang, J., Zhang, Y., Fang, J., Lu, K., Wang, Z., Ma, W. and Wei, Z., J. Am. Chem. Soc., 2015, 137:8176 doi: 10.1021/jacs.5b03449
21. [21]
  An, Q.S., Zhang, F.J., Sun, Q.Q., Zhang, M., Zhang, J., Tang, W.H., Yin, X.X. and Deng, Z.B., Nano Energy, 2016, 26:180 doi: 10.1016/j.nanoen.2016.05.018
22. [22]
  Tamilavan, V., Roh, K.H., Agneeswari, R., Lee, D.Y., Cho, S., Jin, Y., Park, S.H. and Hyun, M.H., J. Mater. Chem. A, 2014, 2:20126 doi: 10.1039/C4TA05086J
23. [23]
  Huang, Y.S., Zhang, M., Chen, H.J., Wu, F., Cao, Z.C., Zhang, L.J. and Tan, S.T., J. Mater. Chem. A, 2014, 2:5218 doi: 10.1039/c4ta00020j
24. [24]
  Kang, T.E., Kim, K.H. and Kim, B.J., J. Mater. Chem. A, 2014, 2:15252 doi: 10.1039/C4TA02426E
25. [25]
  Tan, H., Yu, J.T., Wang, Y.F., Chen, J.H., Tao, Q., Liu, Y., Huang, J. and Zhu, W.G., Org. Electron., 2013, 14:1510 doi: 10.1016/j.orgel.2013.03.018
26. [26]
  Fan, Q.P., Liu, Y., Xiao, M.J., Su, W.Y., Gao, H.S., Chen, J.H., Tan, H., Wang, Y.F., Yang, R.Q. and Zhu, W.G., J. Mater. Chem. C, 2015, 3:6240 doi: 10.1039/C5TC00785B
27. [27]
  Yao, H.F., Ye, L., Zhang, H., Li, S.S., Zhang, S.Q. and Hou, J.H., Chem. Rev., 2016, 116:7397 doi: 10.1021/acs.chemrev.6b00176
28. [28]
  Liu, P., Zhang, K., Liu, F., Jin, Y.C., Liu, S.J., Russell, T.P., Yip, H.L., Huang, F. and Cao, Y., Chem. Mater., 2014, 26:3009 doi: 10.1021/cm500953e
29. [29]
  Hendriks, K.H., Heintges, G.H., Gevaerts, V.S., Wienk, M.M. and Janssen, R.A., Angew. Chem. Int. Ed., 2013, 52:8341 doi: 10.1002/anie.v52.32
30. [30]
  Jiang, T., Yang, J., Tao, Y.T., Fan, C., Xue, L.W., Zhang, Z.G., Li, H., Li, Y.F. and Huang, W., Polym. Chem., 2016, 7:926 doi: 10.1039/C5PY01771H
31. [31]
  Chang, W.H., Gao, J., Dou, L.T., Chen, C.C., Liu, Y.S. and Yang, Y., Adv. Energy Mater., 2014, 4:1300864 doi: 10.1002/aenm.201300864
32. [32]
  Lee, J.W., Ahn, H. and Jo, W. H., Macromolecules, 2015, 48:7836 doi: 10.1021/acs.macromol.5b01826
33. [33]
  Kanimozhi, C., Yaacobi-Gross, N., Chou, K.W., Amassian, A., Anthopoulos, T.D. and Patil, S., J. Am. Chem. Soc., 2012, 134:16532 doi: 10.1021/ja308211n
34. [34]
  Li, W.W., Hendriks, K.H., Wienk, M.M. and Janssen, R.A.J., Acc. Chem. Res., 2016, 49:78 doi: 10.1021/acs.accounts.5b00334
35. [35]
  Liu, Y.H., Li, G.W., Zhang, Z., Wu, L.L., Chen, J.Y., Xu, X.J., Chen, X.B., Ma, W. and Bo, Z.S., J. Mater. Chem. A, 2016, 4:13265 doi: 10.1039/C6TA05471D
36. [36]
  Zhou, H.X., Yang, L.Q., Stuart, A.C., Price, S.C., Liu, S.B. and You, W., Angew. Chem. Int. Ed., 2011, 50:2995 doi: 10.1002/anie.201005451
37. [37]
  Peng, Q., Liu, X.J., Su, D., Fu, G.W., Xu, J. and Dai, L.M., Adv. Mater., 2011, 23:4554 doi: 10.1002/adma.201101933
38. [38]
  Lee, J., Kim, M., Kang, B., Jo, S.B., Kim, H.G., Shin, J. and Cho, K., Adv. Energy Mater., 2014, 4:1400087 doi: 10.1002/aenm.201400087
39. [39]
  Lee, J., Jo, S.B., Kim, M., Kim, H.G., Shin, J., Kim, H. and Cho, K., Adv. Mater., 2014, 26:6706 doi: 10.1002/adma.v26.39
40. [40]
  Wang, N., Chen, Z., Wei, W. and Jiang, Z.H., J. Am. Chem. Soc., 2013, 135:17060 doi: 10.1021/ja409881g
41. [41]
  Xu, X.P., Li, Y., Luo, M.M. and Peng, Q., Chin. Chem. Lett., 2016, DOI:10.1016/j.cclet.2016.05.006 doi: 10.1016/j.cclet.2016.05.006
42. [42]
  Wang, L.X., Cai, D.D., Zheng, Q.D., Tang, C.Q., Chen, S.C. and Yin, Z.G., ACS Macro Lett., 2013, 2:605 doi: 10.1021/mz400185k
43. [43]
  Woo, C.H., Beaujuge, P.M., Holcombe, T.W., Lee, O.P. and Fréchet, J.M.J., J. Am. Chem. Soc., 2010, 132:15547 doi: 10.1021/ja108115y
44. [44]
  Xu, X.P., Feng, K., Li, K. and Peng, Q., J. Mater. Chem. A, 2015, 3:23149 doi: 10.1039/C5TA07205K
45. [45]
  Wang, Z.G., Li, Z.J., Xu, X.P., Li, Y., Li, K. and Peng, Q., Adv. Funct. Mater., 2016, 26:4643 doi: 10.1002/adfm.v26.26
46. [46]
  Peng, Q., Lu, Z.Y., Huang, Y., Xie, M.G., Han, S.H., Peng, J.B. and Cao, Y., Macromolecules, 2004, 37:260 doi: 10.1021/ma0355397
47. [47]
  Li, K., Li, Z.J., Feng, K., Xu, X.P., Wang, L.Y. and Peng, Q., J. Am. Chem. Soc., 2013, 135:13549 doi: 10.1021/ja406220a
48. [48]
  Yang, Y.C., Wu, R.M., Wang, X., Xu, X.P., Li, Z.J., Li, K. and Peng, Q., Chem. Commun., 2014, 50:439 doi: 10.1039/C3CC47677D
49. [49]
  Zhao, J.B., Li, Y.K., Lin, H.R., Liu, Y.H., Jiang, K., Mu, C., Ma, T.X., Lin, L., J.Y., Hu, H.W., Yu, D.M. and Yan, H., Energy Environ. Sci., 2015, 8:520 doi: 10.1039/C4EE02990A
50. [50]
  Mihailetchi, V.D., Koster, L.J.A., Blom, P.W.M., Melzer, C., De Boer, B., van Duren, J.K.J. and Janssen, R.A.J., Adv. Funct. Mater., 2005, 15:795 doi: 10.1002/(ISSN)1616-3028
1. [1]
  Yaohua Li , Qi Cao , Xuanhua Li . Tailoring the configuration of polymer passivators in perovskite solar cells. Chinese Journal of Structural Chemistry, 2025, 44(2): 100413-100413. doi: 10.1016/j.cjsc.2024.100413
2. [2]
  Chengcheng Xie , Chengyi Xiao , Hongshuo Niu , Guitao Feng , Weiwei Li . Mesoporous organic solar cells. Chinese Chemical Letters, 2024, 35(11): 109849-. doi: 10.1016/j.cclet.2024.109849
3. [3]
  Xin Lu , Haoran Sun , Xiaomeng Li , Chunrui Li , Jinfeng Wang , Dandan Zhou . C14-HSL limits the mycelial morphology of pathogen Trichosporon cells but enhances their aggregation: Mechanisms and implications. Chinese Chemical Letters, 2024, 35(6): 108936-. doi: 10.1016/j.cclet.2023.108936
4. [4]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
5. [5]
  Chen Lu , Zefeng Yu , Jing Cao . Advancement in porphyrin/phthalocyanine compounds-based perovskite solar cells. Chinese Journal of Structural Chemistry, 2024, 43(3): 100240-100240. doi: 10.1016/j.cjsc.2024.100240
6. [6]
  Chi Li , Peng Gao . Is dipole the only thing that matters for inverted perovskite solar cells?. Chinese Journal of Structural Chemistry, 2024, 43(6): 100324-100324. doi: 10.1016/j.cjsc.2024.100324
7. [7]
  Yuqing Wang , Zhemin Li , Qingjun Lu , Qizhao Li , Jiaxin Luo , Chengjie Li , Yongshu Xie . Solar cells based on doubly concerted companion dyes with the efficiencies modulated by inserting an ethynyl group at different positions. Chinese Chemical Letters, 2024, 35(5): 109093-. doi: 10.1016/j.cclet.2023.109093
8. [8]
  Kangrong Yan , Ziqiu Shen , Yanchun Huang , Benfang Niu , Hongzheng Chen , Chang-Zhi Li . Curing the vulnerable heterointerface via organic-inorganic hybrid hole transporting bilayers for efficient inverted perovskite solar cells. Chinese Chemical Letters, 2024, 35(6): 109516-. doi: 10.1016/j.cclet.2024.109516
9. [9]
  Bo Yang , Pu-An Lin , Tingwei Zhou , Xiaojia Zheng , Bing Cai , Wen-Hua Zhang . Facile surface regulation for highly efficient and thermally stable perovskite solar cells via chlormequat chloride. Chinese Chemical Letters, 2024, 35(10): 109425-. doi: 10.1016/j.cclet.2023.109425
10. [10]
  Yingfen Li , Zhiqi Wang , Yunhai Zhao , Dajun Luo , Xueliang Zhang , Jun Zhao , Zhenghua Su , Shuo Chen , Guangxing Liang . Potassium doping for grain boundary passivation and defect suppression enables highly-efficient kesterite solar cells. Chinese Chemical Letters, 2024, 35(11): 109468-. doi: 10.1016/j.cclet.2023.109468
11. [11]
  Zhiyang Zhang , Yi Chen , Yingnan Zhang , Chuanlang Zhan . Deuterated chloroform replaces ultra-dry chloroform to achieve high-efficient organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110083-. doi: 10.1016/j.cclet.2024.110083
12. [12]
  Rongjun Zhao , Tai Wu , Yong Hua , Yude Wang . Improving performance of perovskite solar cells enabled by defects passivation and carrier transport dynamics regulation via organic additive. Chinese Chemical Letters, 2025, 36(2): 109587-. doi: 10.1016/j.cclet.2024.109587
13. [13]
  Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2024.100277
14. [14]
  Wenbiao Zhang , Bolong Yang , Zhonghua Xiang . Atomically dispersed Cu-based metal-organic framework directly for alkaline polymer electrolyte fuel cells. Chinese Chemical Letters, 2025, 36(2): 109630-. doi: 10.1016/j.cclet.2024.109630
15. [15]
  Linghui Zou , Meng Cheng , Kaili Hu , Jianfang Feng , Liangxing Tu . Vesicular drug delivery systems for oral absorption enhancement. Chinese Chemical Letters, 2024, 35(7): 109129-. doi: 10.1016/j.cclet.2023.109129
16. [16]
  Yikun Wang , Qiaomei Chen , Shijie Liang , Dongdong Xia , Chaowei Zhao , Christopher R. McNeill , Weiwei Li . Near-infrared double-cable conjugated polymers based on alkyl linkers with tunable length for single-component organic solar cells. Chinese Chemical Letters, 2024, 35(4): 109164-. doi: 10.1016/j.cclet.2023.109164
17. [17]
  Rui Liu , Yue Yu , Lu Deng , Maoxia Xu , Haorong Ren , Wenjie Luo , Xudong Cai , Zhenyu Li , Jingyu Chen , Hua Yu . The synergistic effect of A-site cation engineering and phase regulation enables efficient and stable Ruddlesden-Popper perovskite solar cells. Chinese Chemical Letters, 2024, 35(12): 109545-. doi: 10.1016/j.cclet.2024.109545
18. [18]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
19. [19]
  Fang-Yuan Chen , Wen-Chao Geng , Kang Cai , Dong-Sheng Guo . Molecular recognition of cyclophanes in water. Chinese Chemical Letters, 2024, 35(5): 109161-. doi: 10.1016/j.cclet.2023.109161
20. [20]
  Hongxia Li , Xiyang Wang , Du Qiao , Jiahao Li , Weiping Zhu , Honglin Li . Mechanism of nanoparticle aggregation in gas-liquid microfluidic mixing. Chinese Chemical Letters, 2024, 35(4): 108747-. doi: 10.1016/j.cclet.2023.108747

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(842)
HTML views(49)

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