Citation: Ying Yang, Tong Shan, Jian Cao, Hua-Chun Wang, Ji-Kang Wang, Hong-Liang Zhong, Yun-Xiang Xu. Unsymmetric Side Chains of Indacenodithiophene Copolymers Lead to Improved Packing and Device Performance[J]. Chinese Journal of Polymer Science, ;2020, 38(4): 342-348. doi: 10.1007/s10118-020-2342-9 shu

Unsymmetric Side Chains of Indacenodithiophene Copolymers Lead to Improved Packing and Device Performance

Ying Yang ^a,† ,
Tong Shan ^b,† ,
Jian Cao ^a ,
Hua-Chun Wang ^a ,
Ji-Kang Wang ^a ,
Hong-Liang Zhong ^b,, ,
Yun-Xiang Xu ^a,,

a.
College of Polymer Science & Engineering, State Key Laboratory of Polymer Materials Engineering, Sichuan University, Chengdu 610065, China
b.
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China

Corresponding author: Hong-Liang Zhong, hlzhong@sjtu.edu.cn Yun-Xiang Xu, yxxu@scu.edu.cn
Received Date: 23 July 2019
Revised Date: 20 August 2019
Accepted Date: 20 August 2019
Available Online: 1 April 2020

Two conjugated polymers (PuIDTBD and PuIDTQ) with unsymmetric side chains have been prepared for polymer solar cells using two other polymers (PIDTBD and PIDTQ) with symmetric side chains as control compounds. The combination of methyl and 4-hexylphenyl side chains on the same bridged carbon can ensure good solubility, decrease π-π stacking distances, and bring proper miscibility with PC₇₁BM simultaneously. Therefore, the corresponding polymer solar cells (PSCs) based on donor polymers with unsymmetric side chains exhibited enhanced short-circuit current density (J_SC) and power conversion efficiency (PCE) compared with those of control polymers. The PIDTBD and PIDTQ based devices possessed low PCE of 2.13% and 1.48%, while PCEs of devices based on PuIDTBD and PuIDTQ were improved to 3.93% and 4.12%, respectively. The results demonstrate that unsymmetric side chain engineering of conjugated polymers is an effective approach to achieve high performance PSCs.
- Polymer solar cell,
- Indacenodithiophene,
- Side-chain engineering,
- Unsymmetric
1. [1]
  Wang, G.; Melkonyan, F. S.; Facchetti, A.; Marks, T. J. All-polymer solar cells: recent progress, challenges, and prospects. Angew. Chem. Int. Ed. 2019, 58, 4129−4142. doi: 10.1002/anie.201808976
2. [2]
  Zhao, W.; Qian, D.; Zhang, S.; Li, S.; Inganäs, O.; Gao, F.; Hou, J. Fullerene-free polymer solar cells with over 11% efficiency and excellent thermal stability. Adv. Mater. 2016, 28, 4734−4739. doi: 10.1002/adma.201600281
3. [3]
  Yang, B.; Zhang, S.; Chen, Y.; Cui, Y.; Liu, D.; Yao, H.; Zhang, J.; Wei, Z.; Hou, J. Investigation of conjugated polymers based on naphtho[2,3-c]thiophene-4,9-dione in fullerene-based and fullerene-free polymer solar cells. Macromolecules 2017, 50, 1453−1462. doi: 10.1021/acs.macromol.6b02733
4. [4]
  Sun, C.; Pan, F.; Bin, H.; Zhang, J.; Xue, L.; Qiu, B.; Wei, Z.; Zhang, Z. G.; Li, Y. A low cost and high performance polymer donor material for polymer solar cells. Nat. Commun. 2018, 9, 743. doi: 10.1038/s41467-018-03207-x
5. [5]
  Scharber, M. C. On the efficiency limit of conjugated polymer: fullerene-based bulk heterojunction solar cells. Adv. Mater. 2016, 28, 1994−2001. doi: 10.1002/adma.201504914
6. [6]
  Shi, Z.; Bai, Y.; Chen, X.; Zeng, R.; Tan, Z. A. Tandem structure: A breakthrough in power conversion efficiency for highly efficient polymer solar cells. Sustain. Energy Fuels 2019, 3, 910−934. doi: 10.1039/C8SE00601F
7. [7]
  Chochos, C. L.; Drakopoulou, S.; Katsouras, A.; Squeo, B. M.; Sprau, C.; Colsmann, A.; Gregoriou, V. G.; Cando, A. P.; Allard, S.; Scherf, U.; Gasparini, N.; Kazerouni, N.; Ameri, T.; Brabec, C. J.; Avgeropoulos, A. Beyond donor-acceptor (D-A) approach: Structure-optoelectronic properties—organic photovoltaic performance correlation in new D-A1-D-A2 low-bandgap conjugated polymers. Macromol. Rapid Commun. 2017, 38, 1600720. doi: 10.1002/marc.201600720
8. [8]
  Guo, X.; Baumgarten, M.; Müllen, K. Designing π-conjugated polymers for organic electronics. Prog. Polym. Sci. 2013, 38, 1832−1908. doi: 10.1016/j.progpolymsci.2013.09.005
9. [9]
  Chochos, C. L.; Singh, R.; Kim, M.; Gasparini, N.; Katsouras, A.; Kulshreshtha, C.; Gregoriou, V. G.; Keivanidis, P. E.; Ameri, T.; Brabec, C. J.; Cho, K.; Avgeropoulos, A. Enhancement of the power conversion efficiency in organic photovoltaics by unveiling the appropriate polymer backbone enlargement approach. Adv. Funct. Mater. 2016, 26, 1840−1848. doi: 10.1002/adfm.201504953
10. [10]
  Mahesh, K.; Karpagam, S.; Pandian, K. How to design donor-acceptor based heterocyclic conjugated polymers for applications from organic electronics to sensors. Top. Curr. Chem. 2019, 377, 12. doi: 10.1007/s41061-019-0237-4
11. [11]
  Wang, M.; Hu, X.; Liu, L.; Duan, C.; Liu, P.; Ying, L.; Huang, F.; Cao, Y. Design and synthesis of copolymers of indacenodithiophene and naphtho[1,2-c:5,6-c]bis(1,2,5-thiadiazole) for polymer solar cells. Macromolecules 2013, 46, 3950−3958. doi: 10.1021/ma400355w
12. [12]
  Yin, Y.; Zhang, Y.; Zhao, L. Indaceno-based conjugated polymers for polymer solar cells. Macromol. Rapid Commun. 2018, 39, 1700697. doi: 10.1002/marc.201700697
13. [13]
  Bronstein, H.; Leem, D. S.; Hamilton, R.; Woebkenberg, P.; King, S.; Zhang, W.; Ashraf, R. S.; Heeney, M.; Anthopoulos, T. D.; Mello, J. D.; McCulloch, I. Indacenodithiophene-co-benzothiadiazole copolymers for high performance solar cells or transistors via alkyl chain optimization. Macromolecules 2011, 44, 6649−6652. doi: 10.1021/ma201158d
14. [14]
  Ma, Y.; Kang, Z.; Zheng, Q. Recent advances in wide bandgap semiconducting polymers for polymer solar cells. J. Mater. Chem. A 2017, 5, 1860−1872. doi: 10.1039/C6TA09325F
15. [15]
  Qin, T.; Zang, Y.; Bai, W. Y.; Yao, K.; Xu, Y. X. The influence of oxygen atoms on conformation and π-π stacking of ladder-type donor-based polymers and their photovoltaic properties. Macromol. Rapid Commun. 2017, 38, 1700156. doi: 10.1002/marc.201700156
16. [16]
  Wang, H. C.; Li, Q. Y.; Yin, H. B.; Ren, X.; Yao, K.; Zheng, Y.; Xu, Y. X. Synergistic effects of selenophene and extended ladder-type donor units for efficient polymer solar cells. Macromol. Rapid Commun. 2018, 39, 1700483. doi: 10.1002/marc.201700483
17. [17]
  Xiao, Z.; Liu, F.; Geng, X.; Zhang, J.; Wang, S.; Xie, Y.; Li, Z.; Yang, H.; Yuan, Y.; Ding, L. A carbon-oxygen-bridged ladder-type building block for efficient donor and acceptor materials used in organic solar cells. Sci. Bull. 2017, 62, 1331−1336. doi: 10.1016/j.scib.2017.09.017
18. [18]
  Xu, Y. X.; Chueh, C. C.; Yip, H. L.; Ding, F. Z.; Li, Y. X.; Li, C. Z.; Li, X.; Chen, W. C.; Jen, A. K. Y. Improved charge transport and absorption coefficient in indacenodithieno[3,2-b]thiophene-based ladder-type polymer leading to highly efficient polymer solar cells. Adv. Mater. 2012, 24, 6356−6361. doi: 10.1002/adma.201203246
19. [19]
  Zhang, Z. G.; Li, Y. Side-chain engineering of high-efficiency conjugated polymer photovoltaic materials. Sci. China Chem. 2015, 58, 192−209. doi: 10.1007/s11426-014-5260-2
20. [20]
  Zhang, M.; Guo, X.; Wang, X.; Wang, H.; Li, Y. Synthesis and photovoltaic properties of D-A copolymers based on alkyl-substituted indacenodithiophene donor unit. Chem. Mater. 2011, 23, 4264−4270. doi: 10.1021/cm2019586
21. [21]
  Zhang, W.; Han, Y.; Zhu, X.; Fei, Z.; Feng, Y.; Treat, N. D.; Faber, H.; Stingelin, N.; McCulloch, I.; Anthopoulos, T. D.; Heeney, M. A novel alkylated indacenodithieno[3,2-b]thiophene-based polymer for high-performance field-effect transistors. Adv. Mater. 2016, 28, 3922−3927. doi: 10.1002/adma.201504092
22. [22]
  Zhang, X.; Bronstein, H.; Kronemeijer, A. J.; Smith, J.; Kim, Y.; Kline, R. J.; Richter, L. J.; Anthopoulos, T. D.; Sirringhaus, H.; Song, K.; Heeney, M.; Zhang, W.; McCulloch, I.; DeLongchamp, D. M. Molecular origin of high field-effect mobility in an indacenodithiophene-benzothiadiazole copolymer. Nat. Commun. 2013, 4, 2238. doi: 10.1038/ncomms3238
23. [23]
  Chochos, C. L.; Katsouras, A.; Gasparini, N.; Koulogiannis, C.; Ameri, T.; Brabec, C. J.; Avgeropoulos, A. Rational design of high-performance wide-bandgap (≈2 eV) polymer semiconductors as electron donors in organic photovoltaics exhibiting high open circuit voltages (≈ 1 V). Macromol. Rapid Commun. 2017, 38, 1600614. doi: 10.1002/marc.201600614
24. [24]
  Wang, M.; Cai, D.; Yin, Z.; Chen, S. C.; Du, C. F.; Zheng, Q. Asymmetric-indenothiophene-based copolymers for bulk heterojunction solar cells with 9.14% efficiency. Adv. Mater. 2016, 28, 3359−3365. doi: 10.1002/adma.201505957
25. [25]
  Liu, D.; Zhu, Q.; Gu, C.; Wang, J.; Qiu, M.; Chen, W.; Bao, X.; Sun, M.; Yang, R. High-performance photovoltaic polymers employing symmetry-breaking building blocks. Adv. Mater. 2016, 28, 8490−8498. doi: 10.1002/adma.201602857
26. [26]
  Bai, W.; Xu, X.; Li, Q.; Xu, Y.; Peng, Q. Efficient nonfullerene polymer solar cells enabled by small-molecular acceptors with a decreased fused-ring core. Small Methods 2018, 2, 1700373. doi: 10.1002/smtd.201700373
27. [27]
  Feng, S.; Zhang, C. E.; Liu, Y.; Bi, Z.; Zhang, Z.; Xu, X.; Ma, W.; Bo, Z. Fused-ring acceptors with asymmetric side chains for high-performance thick-film organic solar cells. Adv. Mater. 2017, 29, 1703527. doi: 10.1002/adma.201703527
28. [28]
  Cao, J.; Shan, T.; Wang, J. K.; Xu, Y. X.; Ren, X.; Zhong, H. Stereoisomerism of ladder-type acceptor molecules and its effect on photovoltaic properties. Dyes Pigments 2019, 165, 354−360. doi: 10.1016/j.dyepig.2019.02.046
29. [29]
  Song, C. E.; Kim, Y. J.; Suranagi, S. R.; Kini, G. P.; Park, S.; Lee, S. K.; Shin, W. S.; Moon, S. J.; Kang, I. N.; Park, C. E.; Lee, J. C. Impact of the crystalline packing structures on charge transport and recombination via alkyl chain tunability of DPP-based small molecules in bulk heterojunction solar cells. ACS Appl. Mater. Interfaces 2016, 8, 12940−12950. doi: 10.1021/acsami.6b01576
30. [30]
  Fan, J.; Zhang, Y.; Lang, C.; Qiu, M.; Song, J.; Yang, R.; Guo, F.; Yu, Q.; Wang, J.; Zhao, L. Side chain effect on poly(beznodithiophene-co-dithienobenzoquinoxaline) and their applications for polymer solar cells. Polymer 2016, 82, 228−237. doi: 10.1016/j.polymer.2015.11.052
31. [31]
  Liu, X.; Li, Q.; Li, Y.; Gong, X.; Su, S. J.; Cao, Y. Indacenodithiophene core-based small molecules with tunable side chains for solution-processed bulk heterojunction solar cells. J. Mater. Chem. A 2014, 2, 4004−4013. doi: 10.1039/c3ta14659f
32. [32]
  Liu, D.; Wang, J.; Gu, C.; Li, Y.; Bao, X.; Yang, R. Stirring up acceptor phase and controlling morphology via choosing appropriate rigid aryl rings as lever arms in symmetry-breaking benzodithiophene for high-performance fullerene and fullerene-free polymer solar cells. Adv. Mater. 2018, 30, 1705870. doi: 10.1002/adma.201705870
33. [33]
  Zhu, T.; Wan, Y.; Guo, Z.; Johnson, J.; Huang, L. Two birds with one stone: tailoring singlet fission for both triplet yield and exciton diffusion length. Adv. Mater. 2016, 28, 7539−7547. doi: 10.1002/adma.201600968
1. [1]
  Jiang Xindong , Yue Shuai , Chen Kepeng , Shao Zhumei , Li Chen , Su Yajun , Zhao Jianzhang . Synthesis, properties and application of novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF₂) fluorescent dyes: BOPYPYs. Chinese Chemical Letters, 2019, 30(12): 2271-2273. doi: 10.1016/j.cclet.2019.07.027
2. [2]
  ZHANG Zhongqiang , ZHANG Shuhua , LIU Zhixi , ZHANG Zhiguo , LI Yongfang , LI Changzhi , CHEN Hongzheng . A Simple Electron Acceptor with Unfused Backbone for Polymer Solar Cells. Acta Physico-Chimica Sinica, 2019, 35(4): 394-400. doi: 10.3866/PKU.WHXB201805091
3. [3]
  GUPTA Monika , YAN Dong , SHEN Fugang , XU Jianzhong , ZHAN Chuanlang . Perylenediimide: Phosphonium-Based Binary Blended Small-Molecule Cathode Interlayer for Efficient Fullerene-Free Polymer Solar Cells with Open Circuit Voltage to 1.0 V. Acta Physico-Chimica Sinica, 2019, 35(5): 496-502. doi: 10.3866/PKU.WHXB201805101
4. [4]
  Zhang Qiang , Liu Jiangang , Yu Xinhong , Han Yanchun . Design optimized intermixed phase by tuning polymer-fullerene intercalation for free charge generation. Chinese Chemical Letters, 2019, 30(7): 1405-1409. doi: 10.1016/j.cclet.2019.04.004
5. [5]
  Liu Wenxu , Li Weiping , Yao Jiannian , Zhan Chuanlang . Achieving high short-circuit current and fill-factor via increasing quinoidal character on nonfullerene small molecule acceptor. Chinese Chemical Letters, 2018, 29(3): 381-384. doi: 10.1016/j.cclet.2017.11.018
6. [6]
  Li Xiaofang , Li Kun , Su Dan , Shen Fugang , Huo Shuying , Fu Hongbing , Zhan Chuanlang . Design a thieno[3, 2-b]thiophene bridged nonfullerene acceptor to increase open-circuit voltage, short-circuit current-density and fill factor via the ternary strategy. Chinese Chemical Letters, 2020, 31(5): 1243-1247. doi: 10.1016/j.cclet.2019.10.029
7. [7]
  Xiao CHEN , QingBin XUE , Kong Zhang YANG , Qi Zhen ZHANG . STUDIES　ON　THE　AGGRESGATION　BEHAVIOUR　OF　A　SIDE-CHAIN　LIQUID　CRYSTALLINE　POLYMER　IN　LANGMUIR-BLODGETT　FILMS. Chinese Chemical Letters, 1996, 7(4): 371-374.
8. [8]
  Zhanhui Yang , Jiaxi Xu . A Suggestion to Clarify the Chinese Descriptions on Organic Molecule Symmetries. University Chemistry, 2020, 35(7): 181-184. doi: 10.3866/PKU.DXHX202003104
9. [9]
  LI Dan , LIANG Ran , YUE He , WANG Peng , FU Li-Min , ZHANG Jian-Ping , AI Xi-Cheng . Influence of Donor and Acceptor Mass Ratios on P3HT:PCBM Film Structure and Device Performance. Acta Physico-Chimica Sinica, 2012, 28(06): 1373-1379. doi: 10.3866/PKU.WHXB201204061
10. [10]
  WU Na , LUO Qun , WU Zhen-Wu , MA Chang-Qi . Influence of Electrode Interfacial Buffer Layers on Thermal Stability of P3HT:PC₆₁BM Solar Cells. Acta Physico-Chimica Sinica, 2015, 31(7): 1413-1420. doi: 10.3866/PKU.WHXB201505142
11. [11]
  FENG Shiyu , LU Hao , LIU Zekun , LIU Yahui , LI Cuihong , BO Zhishan . Designing a High-Performance A-D-A Fused-Ring Electron Acceptor via Noncovalently Conformational Locking and Tailoring Its End Groups. Acta Physico-Chimica Sinica, 2019, 35(4): 355-360. doi: 10.3866/PKU.WHXB201805161
12. [12]
  Xian Rong Cai , Hao Chen , Tao Zhang , Xing Xu , Ying Li , Qing Jiang . Synthesis and characterization of a novel main chain oxadiazole-based copolymer for n-type solar cell material. Chinese Chemical Letters, 2007, 18(11): 1342-1346. doi: 10.1016/j.cclet.2007.09.035
13. [13]
  Jian Lu , Xiao-Bo Tian , Wei Huang . A new strategy for synthesis of branched cyclic peptide by Asn side-chain hydrazide ligation. Chinese Chemical Letters, 2015, 26(8): 946-950. doi: 10.1016/j.cclet.2015.05.016
14. [14]
  Jun Hua YU , Yu Xiang WENG , Xue Song WANG , Lei ZHANG , Bao Wen ZHANG , Yi CAO . Porphyrins in Reverse Micelles:the Side-chain Length and the Triplet-state Lifetime. Chinese Chemical Letters, 2003, 14(8): 844-847.
15. [15]
  Shu Sun , Jian-Bing Shi , Yu-Ping Dong , Chen Lin , Xiao-Yu Hub , Le-Yong Wang . A pillar[5]arene-based side-chain pseudorotaxanes and polypseudorotaxanes as novel fluorescent sensors for the selective detection of halogen ions. Chinese Chemical Letters, 2013, 24(11): 987-992.
16. [16]
  Hui Zhong XUE , Zheng Ming GUO , Ai Hua KONG , Guo Pci WU , Bai Yong MAO , Xiu Juan JIANG , Zhi Ping GU . THE SYNTHESIS OF UNSYMMETRIC ANALOGS OF GOSSYPOL——6-O-METHYLGOSSYPOL. Chinese Chemical Letters, 1992, 3(3): 165-166.
17. [17]
  Ji Liang SHI , Yuan Chao ZHANG , Li Jun XIA , Xi Kui JIANG . DO FLAT MOLECULES WITHOUT A SIDE-CHAIN READILY FORM AGGREGATES ? A FLUORESCENCE STUDY OF PYRENE EXCIMER AND EXCIPLEX FORMATION IN ETOH-H₂O AND MEOH-H₂O SOLVENT SYSTEMS. Chinese Chemical Letters, 1990, 1(2): 149-152.
18. [18]
  Jia Lei , Tang Qiang , Luo Meiming , Zeng Xiaoming . One-Step Synthesis of Unsymmetric 1, 1'-Biaryl-2, 2'-diamines by the Reaction of 2-Naphthols with Aryl Hydrazines. Chinese Journal of Organic Chemistry, 2018, 38(2): 443-450. doi: 10.6023/cjoc201707018

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1172)
HTML views(18)

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