Citation: Zhong-qiang Zhang, Zhi-xi Liu, Kang-rong Yan, Huan-bin Li, Wen-qing Liu, Xin-hui Lu, Han-ying Li, Hong-zheng Chen, Chang-zhi Li. Photovoltaic Properties of DPP-based Two-and Three-component Polymers[J]. Acta Polymerica Sinica, ;2018, (2): 295-303. doi: 10.11777/j.issn1000-3304.2018.17253 shu

Photovoltaic Properties of DPP-based Two-and Three-component Polymers

1.
Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization, State Key Laboratory of Silicon Materials, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027
2.
Department of Physics, The Chinese University of Hong Kong, Hong Kong

Corresponding author: Chang-zhi Li, czli@zju.edu.cn
Received Date: 4 September 2017
Revised Date: 19 September 2017

Diketopyrrolopyrrole (DPP) is attractive for building conjugated polymers for polymer solar cell (PSC) and organic field effect transistor (OFET). Yet the usual access to DPP conjugated polymers is via donor-acceptor (D-A) two-component polymerization. However, the number of excellent polymers based on the D-A combination is still limited, which promotes researchers to explore new strategy for preparation of novel conjugated polymers and to understand their structure-property relationship. In this work, a DPP-based polymer P1 was first obtained with co-polymerization of DPP (A) and alkoxyl benzene (D). Further, two novel polymers ( P2 and P3 ) were developed via introducing a third electron-deficient monomer X (difluoro-benzothiadiazole or naphthalene diimide) in the polymerization process. P1 - P3 polymers (molecular weight:3.83×10⁴, 5.30×10⁴ and 6.56×10⁴) showed good solubility in common organic solvents. Due to the hybridization of the molecular orbitals between their three components (D, A and X), P2 and P3 showed narrower bandgaps (1.26 and 1.27 eV) than P1 , and their absorption thus red-shifted up to 1000 nm in comparison to that of D-A polymer P1 (bandgap of 1.50 eV). The introduction of electron-deficient monomers also deepened the highest occupied molecular orbital (HOMO) levels of P2 and P3 to -5.28 and -5.33 eV, which was beneficial to a larger open circuit voltage (V_OC) in PSCs. Moreover, the introduction of the third monomer X altered the film properties of the polymers. It showed that P1 with preference of face-on orientation exhibited a good power conversion efficiency (PCE) in PSCs, while P2 demonstrated an improved hole mobility in OFET due to the preferable edge-on orientation. When blended with [6, 6]-phenyl-C₇₁-butyric acid methyl ester (PC₇₁BM), P1 showed a PCE of 2.56%, with a V_OC of 0.68 V, a short circuit current density (J_SC) of 5.71 mA cm^-2 and a fill factor (FF) of 0.66, while P2 gave a lower PCE of 1.79%, with a V_OC of 0.71 V, a J_SC of 3.91 mA cm^-2 and a FF of 0.65. This work provides references for the design of novel conjugated polymers for PSCs and OFETs.
- Polymer solar cells,
- Copolymerization,
- Diketopyrrolopyrrole,
- Electron deficient unit
1. [1]
  Huang Y, Kramer E J, Heeger A J, Bazan G C. Chem Rev, 2014, 114(14):7006-7043 doi: 10.1021/cr400353v
2. [2]
  Nguyen T L, Choi H, Ko S J, Uddin M A, Walker B, Yum S, Jeong J E, Yun M H, Shin T J, Hwang S, Kim J Y, Woo H Y. Energy Environ Sci, 2014, 7(9):3040-3051 doi: 10.1039/C4EE01529K
3. [3]
  Liao S H, Jhuo H J, Cheng Y S, Chen S A. Adv Mater, 2013, 25(34):4766-4771 doi: 10.1002/adma.v25.34
4. [4]
  Guo X, Zhang M, Ma W, Ye L, Zhang S, Liu S, Ade H, Huang F, Hou J. Adv Mater, 2014, 26(24):4043-4049 doi: 10.1002/adma.v26.24
5. [5]
  Xu T, Yu L. Mater Today, 2014, 17(1):11-15 doi: 10.1016/j.mattod.2013.12.005
6. [6]
  Li Y F. Accounts Chem Res, 2012, 45(5):723-733
7. [7]
  Wang Li, Xu Miao, Ying Lei, Liu Feng, Cao Yong. Acta Polymerica Sinica, 2008, (10):993-997 doi: 10.3321/j.issn:1000-3304.2008.10.011
8. [8]
  Lai Y Y, Cheng Y J, Hsu C S. Energy Environ Sci, 2014, 7(6):1866-1883 doi: 10.1039/c3ee43080d
9. [9]
  Li C Z, Yip H L, Jen A K Y. J Mater Chem, 2012, 22(10):4161-4177 doi: 10.1039/c2jm15126j
10. [10]
  Hu Z, Ying L, Huang F, Cao Y, Sci China Chem, 2017, 60(5):571-582
11. [11]
  Scharber M C. Adv Mater, 2016, 28(10):1994-2001 doi: 10.1002/adma.201504914
12. [12]
  Jung J W, Jo J W, Jung E H, Jo W H. Org Electron, 2016, 31:149-170 doi: 10.1016/j.orgel.2016.01.034
13. [13]
  Lu L, Zheng T, Wu Q, Schneider A M, Zhao D, Yu L. Chem Rev, 2015, 115(23):12666-12731 doi: 10.1021/acs.chemrev.5b00098
14. [14]
  Li W, Hendriks K H, Wienk M M, Janssen R A J. Acc Chem Res, 2016, 49(1):78-85
15. [15]
  Cheng Y J, Yang S H, Hsu C S. Chem Rev, 2009, 109(11):5868-5923 doi: 10.1021/cr900182s
16. [16]
  Bronstein H, Chen Z, Ashraf R S, Zhang W, Du J, Durrant J R, Tuladhar P S, Song K, Watkins S E, Geerts Y, Wienk M M, Janssen R A, Anthopoulos T, Sirringhaus H, Heeney M, McCulloch I. J Am Chem Soc, 2011, 133(10):3272-3275 doi: 10.1021/ja110619k
17. [17]
  Subbiah J, Purushothaman B, Chen M, Qin T, Gao M, Vak D, Scholes F H, Chen X, Watkins S E, Wilson G J, Holmes A B, Wong W W, Jones D J. Adv Mater, 2014, 27(4):702-705
18. [18]
  Jung J W, Liu F, Russell T P, Jo W H. Adv Mater, 2015, 27(45):7462-7468 doi: 10.1002/adma.201503902
19. [19]
  Ma T, Jiang K, Chen S, Hu H, Lin H, Li Z, Zhao J, Liu Y, Chang Y M, Hsiao C C, Yan H. Adv Energy Mater, 2015, 5(20):1501282
20. [20]
  Shah M N, Zhang S, Sun Q, Ullah F, Chen H, Li C Z. Tetrahedron Lett, 2017, 58(30):2975-2980
21. [21]
  Zhou C, Zhang G, Zhong C, Jia X, Luo P, Xu R, Gao K, Jiang X, Liu F, Russell T P, Huang F, Cao Y. Adv Energy Mater, 2017, 7(1):1601081 doi: 10.1002/aenm.v7.1
22. [22]
  Deng Yunfeng, Bao Cheng, Tian Hongkun, Xie Zhiyuan, Geng Yanhou. Acta Polymerica Sinica, 2013, (5):609-618
23. [23]
  Liu Y, Zhao J, Li Z, Mu C, Ma W, Hu H, Jiang K, Lin H, Ade H, Yan H. Nat Commun, 2014, 5:5293
24. [24]
  Vohra V, Kawashima K, Kakara T, Koganezawa T, Osaka I, Takimiya K, Murata H. Nat Photon, 2015, 9(6):403-408 doi: 10.1038/nphoton.2015.84
25. [25]
  Huang J, Zhang X, Zheng D, Yan K, Li C Z, Yu J. Solar RRL, 2017, 1(1):1600008 doi: 10.1002/solr.201600008
26. [26]
  Huang J, Wang H, Yan K, Zhang X, Chen H, Li C Z, Yu J. Adv Mater, 2017, 29(19):1606729 doi: 10.1002/adma.v29.19
27. [27]
  Huang J, Carpenter J H, Li C Z, Yu J S, Ade H, Jen A K Y. Adv Mater, 2016, 28(5):967-974 doi: 10.1002/adma.v28.5
28. [28]
  Bin H, Gao L, Zhang Z. G, Yang Y, Zhang Y, Zhang C, Chen S, Xue L, Yang C, Xiao M, Li Y. Nat Commun, 2016, 7:13651 doi: 10.1038/ncomms13651
29. [29]
  Bin H, Zhang Z. G, Gao L, Chen S, Zhong L, Xue L, Yang C, Li Y. J Am Chem Soc, 2016, 138(13):4657-4664 doi: 10.1021/jacs.6b01744
30. [30]
  Li S, Ye L, Zhao W, Zhang S, Mukherjee S, Ade H, Hou J. Adv Mater, 2016, 28(42):9423-9429
31. [31]
  Zhao W, Li S, Yao H, Zhang S, Zhang Y, Yang B, Hou J. J Am Chem Soc, 2017, 139(21):7148-7151 doi: 10.1021/jacs.7b02677
32. [32]
  Liu J, Chen S, Qian D, Gautam B, Yang G, Zhao J, Bergqvist J, Zhang F, Ma W, Ade H, Inganäs O, Gundogdu K, Gao F, Yan H. Nat Energy, 2016, 1(7):16089
33. [33]
  Li S, Zhang Z, Shi M, Li C Z, Chen H. Phys Chem Chem Phys, 2017, 19:3440-3458 doi: 10.1039/C6CP07465K
34. [34]
  Zang Y, Li C Z, Chueh C C, Williams S T, Jiang W, Wang Z H, Yu J S, Jen A K Y. Adv Mater, 2014, 26(32):5708-5714 doi: 10.1002/adma.201401992
35. [35]
  Li S, Liu W, Li C Z, Shi M, Chen H. Small, 2017, DOI:10.1002/smll.201701120 doi: 10.1002/smll.201701120
36. [36]
  Beaujuge P M, Amb C M, Reynolds J R. Acc Chem Res, 2010, 43(11):1396-1407 doi: 10.1021/ar100043u
37. [37]
  Henson Z B, Mullen K, Bazan G C. Nat Chem, 2012, 4(9):699-704 doi: 10.1038/nchem.1422
38. [38]
  Zerdan R B, Shewmon N T, Zhu Y, Mudrick J P, Chesney K J, Xue J, Castellano R K. Adv Funct Mater, 2014, 24(38):5993-6004 doi: 10.1002/adfm.201401030
39. [39]
  Qin H, Li L, Guo F, Su S, Peng J, Cao Y, Peng X. Energy Environ Sci, 2014, 7(4):1397-1401 doi: 10.1039/C3EE43761B
40. [40]
  Xu J Q, Liu W, Liu S Y, Ling J, Mai J, Lu X, Li C Z, Jen A K Y, Chen H. Sci China Chem, 2017, 60(4):561-569 doi: 10.1007/s11426-016-9003-9
41. [41]
  Ullah F, Qian S, Yang W, Shah M N, Zhang Z, Chen H, Li C Z. Chinese Chem Lett, 2017, DOI:10.1016/j.cclet.2017.08.009 doi: 10.1016/j.cclet.2017.08.009
42. [42]
  Zhou J, Zuo Y, Wan X, Long G, Zhang Q, Ni W, Liu Y, Li Z, He G, Li C, Kan B, Li M, Chen Y. J Am Chem Soc, 2013, 135(23):8484-8487
43. [43]
  Tang A, Zhan C, Yao J, Zhou E. Adv Mater, 2017, 29(2):1600013
44. [44]
  Shahid M, McCarthy-Ward T, Labram J, Rossbauer S, Domingo E B, Watkins S E, Stingelin N, Anthopoulos T D, Heeney M. Chem Sci, 2012, 3(1):181-185 doi: 10.1039/C1SC00477H
45. [45]
  Cho M J, Shin J, Yoon S H, Lee T W, Kaur M, Choi D H. Chem Commun, 2013, 49(64):7132-7134 doi: 10.1039/c3cc43742f
46. [46]
  Ashraf R S, Meager I, Nikolka M, Kirkus M, Planells M, Schroeder B C, Holliday S, Hurhangee M, Nielsen C B, Sirringhaus H, McCulloch I. J Am Chem Soc, 2015, 137(3):1314-1321
47. [47]
  Chen X, Zhang Z, Ding Z, Liu J, Wang L. Angew Chem Int Ed, 2016, 55(35):10376-10380 doi: 10.1002/anie.201602775
48. [48]
  Liu Y, Chen C C, Hong Z, Gao J, Yang Y M, Zhou H, Dou L, Li G, Yang Y. Sci Rep, 2013, 3:3356 doi: 10.1038/srep03356
49. [49]
  Li W, Hendriks K H, Furlan A, Roelofs W S C, Meskers S C J, Wienk M M, Janssen R A J. Adv Mater, 2014, 26(10):1565-1570 doi: 10.1002/adma.201304360
50. [50]
  Fu L, Fu W, Cheng P, Xie Z, Fan C, Shi M, Ling J, Hou J, Zhan X, Chen H. J Mater Chem A, 2014, 2(18):6589-6597 doi: 10.1039/c3ta13534a
51. [51]
  Liu S, Wu C, Li C Z, Liu S, Wei K, Chen H, Jen A K Y. Adv Sci, 2015, 2(4):1500014 doi: 10.1002/advs.201500014
52. [52]
  Li W, Hendriks K H, Furlan A, Wienk M M, Janssen R A. J Am Chem Soc, 2015, 137(6):2231-2234 doi: 10.1021/ja5131897
53. [53]
  Li W, Roelofs W S, Wienk M M, Janssen R A. J Am Chem Soc, 2012, 134(33):13787-13795 doi: 10.1021/ja305358z
54. [54]
  Yue J, Liang J, Sun S, Zhong W, Lan L, Ying L, Yang W, Cao Y, Dyes Pigments, 2015, 123:64-71 doi: 10.1016/j.dyepig.2015.07.021
55. [55]
  Li S, Liu W, Shi M, Mai J, Lau T K, Wan J, Lu X, Li C Z, Chen H. Energy Environ Sci, 2016, 9(2):604-610 doi: 10.1039/C5EE03481G
56. [56]
  Liu W, Li S, Huang J, Yang S, Chen J, Zuo L, Shi M, Zhan X, Li C Z, Chen H. Adv Mater, 2016, 28, ,44, 9729-9734 doi: 10.1002/adma.201603518
57. [57]
  Hendriks K H, Heintges G H, Gevaerts V S, Wienk M M, Janssen R A. Angew Chem Int Ed, 2013, 52(32):8341-8344 doi: 10.1002/anie.v52.32
58. [58]
  Kang I, Yun H J, Chung D S, Kwon S K, Kim Y H. J Am Chem Soc, 2013, 135(40):14896-14899 doi: 10.1021/ja405112s
59. [59]
  Goujon A, Du G, Moulin E, Fuks G, Maaloum M, Buhler E, Giuseppone N. Angew Chem Int Ed, 2016, 55(2):703-707
60. [60]
  Li Q, Peng M, Li H, Zhong C, Zhang L, Cheng X, Peng X, Wang Q, Qin J, Li Z. Org Lett, 2012, 14(8):2094-2097 doi: 10.1021/ol300607m
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Photovoltaic Properties of DPP-based Two-and Three-component Polymers

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

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通讯作者: 陈斌, bchen63@163.com