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Progress in Chemistry 2022, Vol. 34 Issue (12): 2715-2728 DOI: 10.7536/PC220511 Previous Articles   

• CONTENTS •

Research Progress of Materials and Devices for Organic Photovoltaics Based on Non-Fused Ring Electron Acceptors

Yuxaun Du1,3, Tao Jiang1, Meijia Chang2(), Haojie Rong3, Huanhuan Gao1(), Yu Shang1   

  1. 1 School of Materials Science and Engineering, Xi’an Shiyou University,Xi’an 710065, China
    2 School of Environmental Engineering and Chemistry, Luoyang Institute of Science and Technology,Luoyang 471023, China
    3 Xi’an Modern Chemistry Research Institute,Xi’an 710065, China
  • Received: Revised: Online: Published:
  • Contact: Meijia Chang, Huanhuan Gao
  • Supported by:
    National Natural Science Foundation Research Project of Shaanxi Province(2021JQ-595); National Natural Science Foundation of China(22109063); Xi’an Shiyou University Graduate Innovation and Practical Ability Training Program(YCS21112074); Scientific Research Program Funded by Shaanxi Provincial Education Department(20JK0845); Key Projects of Henan Provincial Department of Education(21A150034)
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Fused-ring electron acceptors (FREAs) based organic solar cells (OSCs) have achieved rapidly development in recent years. However, the complexity of molecular structure of fused-ring electron acceptors leads to high synthesis costs and low yields, limiting their further commercial applications. Non-fused-ring small molecule acceptors have attracted widespread attention due to their simple moleclar structure, structural diversity, and low synthesis cost due to their application of C—C single bonds. In this review, from the perspective of materials design, focusing on the development of non-fused-ring electron acceptors (NFREAs), this paper will briefly discuss the influence of structural regulation on the basic properties, aggregation structure, molecular packing, active layer morphology and the corresponding photovoltaic performances. Further elucidating the structure-property relationships of non-fused-ring acceptor materials. Finally, we will prospect the development and challenge of non-fused-ring acceptors based OSCs from the point view of material design, device optimization, device photovoltaic performance, and device stability.

Contents

1 Introduction

2 Research progress of non-fused ring electron acceptors

2.1 Origin of intramolecular noncovalent interactions

2.2 Application of intramolecular noncovalent interactions in non-fused ring acceptors

2.3 Fully non-fused ring acceptors

2.4 Application of NFREAs with the large steric hindrance side chains

3 Conclusion and outlook

3.1 Material design

3.2 Device optimization

3.3 Morphology optimization

3.4 Device Stability

Key words: organic solar cells, non-fused ring electron acceptors, intramolecular noncovalent conformational lock, large sterically hindered side chain
Fig. 1 Chemical structures of representative IDT-based NFREAs
Table 1 Device performance of organic solar cells based on representative early non-fused ring acceptors
Acceptor Donor Voc (V) Jsc (mA·cm-2) FF (%) PCE (%) ref
IDT-BC6 PBDB-T 0.920 5.63 44.0 2.30 24
IDT-BOC6 PBDB-T 1.010 17.52 54.0 9.60 24
ITOIC PBDB-T 1.024 15.73 55.1 8.87 25
ITOIC-F PBDB-T 0.946 18.60 60.5 10.65 25
ITOIC-2F PBDB-T 0.897 21.04 64.5 12.17 25
IEIC PBDTTT-E-T 0.900 11.70 47.0 4.90 26
IEICO PBDTTT-E-T 0.820 17.70 58.0 8.40 26
IEICO-4F PBDTTT-EFT 0.739 22.80 59.4 10.00 27
IEICO-4Cl PTB7-Th 0.727 22.80 62.0 10.30 28
Fig. 2 Chemcial structures of representative NFREAs featuring electron-donating units as the central core
Table 2 Device performance of organic solar cells based on representative non-fused ring acceptors with intramolecular noncovalent Interactions
Acceptor Donor Voc (V) Jsc (mA·cm-2) FF (%) PCE (%) ref
DF-PCIC PBDB-T 0.910 15.66 72.00 10.14 29
HF-PCIC PBDB-TF 0.910 17.81 70.77 11.49 30
HC-PCIC PBDB-TF 0.890 18.13 72.06 11.75 31
DOC6-IC PBDB-T 0.910 19.21 60.11 10.52 32
DOC8-IC PBDB-T 0.920 17.74 57.65 9.41 32
DOC2C6-IC PBDB-T 0.930 18.85 63.33 11.10 32
DOC2C6-2F PBDB-T 0.850 21.35 73.15 13.24 32
UF-EH-2F J52 0.790 24.87 69.00 13.56 33
F-BDTC-4Cl PBDB-T 0.836 19.28 63.80 10.28 34
DNO15T PBDB-T 0.890 18.95 63.56 10.72 35
BTCIC PBDB-T 0.790 18.6 63.00 9.30 41
BTCIC-4Cl PBDB-T-4Cl 0.750 21.00 66.00 10.50 41
BT-IC4F PBDB-T 0.690 21.40 66.40 9.830 42
BT2F-IC4F PBDB-T 0.670 19.43 64.70 8.450 42
BTOR-IC4F PBDB-T 0.800 20.57 69.60 11.48 42
BTzO-4F PBDB-T 0.839 23.58 69.73 13.80 43
NoCA-5 J52 0.814 26.02 69.96 14.82 44
QCIC3 PBDB-T 0.816 19.39 66.90 10.55 39
UF-Qx-2F J52 0.780 21.64 62.12 10.54 40
UF-Qx-2Cl J52 0.760 22.71 63.09 10.81 40
Fig. 3 Chemcial structures of representative NFREAs featuring electron-withdrawing units as the central core
Fig. 4 Chemcial structures of representative fully NFREAs
Table 3 Device performance of organic solar cells based on representative fully non-fused ring acceptors
Acceptor Donor Voc (V) Jsc (mA·cm-2) FF (%) PCE (%) ref
PTICH PBDB-TF 0.92 8.22 54.00 4.08 22
PTIC PBDB-TF 0.93 16.73 66.00 10.27 22
PTICO PBDB-TF 1.01 12.60 52.00 6.62 22
4T-1 PBDB-T 0.84 12.70 51.71 5.53 45
4T-2 PBDB-T 0.82 15.68 70.32 9.09 45
4T-3 PBDB-T 0.81 17.27 72.45 10.15 45
4T-4 PBDB-T 0.94 14.27 61.82 8.27 45
4T-3 D18 0.93 18.28 70.97 12.04 45
TPT4F PBDB-TF 1.00 13.36 57.00 7.67 46
TPT4Cl PBDB-TF 1.04 15.77 62.00 10.16 46
Fig. 5 2D-GIWAXS patterns of neat (a)BTCN-O and (b) BTCN-M films. (c) Corresponding intensity profiles in the out-of-plane (OOP) and in-plane (IP) directions. (Reprinted with permission from Ref[47]; Copyright (2018) The American Chemical Society)
Fig. 6 Chemcial structures of representative NFREAs with the large steric hindrance side chains
Table 4 OSCs performances of representative NFREAs with the large steric hindrance side chain based devices
Acceptor Donor Voc (V) Jsc (mA·cm-2) FF (%) PCE (%) ref
BTCN-M PBDB-T 0.98 12.03 50.00 5.89 47
PC71BM BTCN-O 0.97 11.68 59.00 6.68 47
PTB4F PBDB-TF 0.94 14.55 51.48 7.04 48
PTB4Cl PBDB-TF 0.93 19.01 72.17 12.76 48
o-4TBC-2F PBDB-T 0.76 20.48 65.7 10.26 49
m-4TBC-2F PBDB-T 0.84 7.90 40.0 2.63 49
A4T-16 PBDB-TF 0.876 21.8 79.8 15.2 23
A4T-21 PBDB-TF 0.936 5.55 30.3 1.57 23
A4T-23 PBDB-TF 0.870 21.0 56.8 10.04 23
CH3-2F PBDB-T 0.77 22.76 60.22 12.28 50
2BTh-2F PBDB-T 0.84 24.02 72.14 14.53 51
2BTh-2F D18 0.90 23.61 72.30 15.44 51
TTC6 D18 0.93 10.20 46.3 4.41 52
TT-C8T D18 0.91 19.31 59.1 10.42 52
TT-TC8 D18 0.86 23.06 66.2 13.13 52
LW-out-2F PBDB-T 0.84 22.78 67.23 12.83 53
A4T-25 PBDB-TF 0.901 17.2 50.5 7.83 54
A4T-26 PBDB-TF 0.885 18.9 72.3 12.1 54
Fig. 7 (a) The single-crystal structure of 2BTh-2F.(b) 3D molecular packing along the b-crystallographic axis and packing along the c-crystallographic axis. (Reprinted with permission from Ref.[51]; Copyright (2021) Wiley-VCH) (c) 2D-GIWAXS patterns of neat acceptors LW-out-2F and LW-in-2F. (Reprinted with permission from Ref[53]; Copyright (2022) Elsevier)
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