J. Semicond. > 2022, Volume 43 > Issue 5 > 050203

RESEARCH HIGHLIGHTS

Nonfullerene acceptors based on perylene monoimides

Yutong Ji1, 2, Helong Bai1, 2, Lixiu Zhang3, Youdi Zhang1, 2, and Liming Ding3,

+ Author Affiliations

 Corresponding author: Youdi Zhang, zhangyd@ccsfu.edu.cn; Liming Ding, ding@nanoctr.cn

DOI: 10.1088/1674-4926/43/5/050203

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Nonfullerene organic solar cells (NF-OSCs) have become a research hotspot, and the device efficiency has been constantly updated[1-14]. The efficiency of binary and ternary solar cells has exceeded 18%[15-17] and 19%[18], respectively. In the early study of OSCs, the development of organic acceptors lagged behind that of organic donors. In addition to the common fullerene acceptors PC61BM and PC71BM, there is growing interest in developing new electron acceptors. The two fullerene acceptors were derived from C60 and C70, which were chemically modified to improve the solubility. Later, Li et al. developed a C60 derivative ICBA[19] and a C70 derivative IC70BA[20]. Compared with PC61BM and PC71BM, the lowest unoccupied molecular orbital (LUMO) levels of these two acceptors increased by 0.17 and 0.19 eV, respectively. This is conducive to the increase of open-circuit voltage (Voc). At present, the development of fullerene acceptors is limited, the reason are as follows: (1) they show weak absorption in the visible region, which is not conducive to the full use of sunlight; (2) it is difficult to improve the absorption by the chemical modification; (3) difficult chemical synthesis and high cost; (4) it is difficult to control the morphology, and the aggregation easily takes place in thin films. The advantages of fullerene acceptors are also obvious, e.g., (1) fullerene acceptors can accept and transport electrons in three dimensions due to their delocalized LUMO; (2) high electron mobility. Perylene diimides (PDIs) have been widely used in biological imaging, and they are widely-studied non-fullerene acceptors. PDIs have many advantages, such as high electron mobility and high electron affinity[21]. In 1986, C. W. Tang of Kodak prepared two-layer OSCs by depositing copper phthalocyanine (CuPc) as the donor and perylene tetracarboxylic derivative (PV) as the accepter in vacuo, achieving a power conversion efficiency (PCE) of 1%[22]. PDI-based devices were made by solution processing, and the aggregation yielded micron-sized crystals. When the acceptors were blended with donors, large domains formed[23]. Since exciton diffusion length and life were limited, the domain size should be well controlled.

The solar cell parameters consist of Voc, short-circuit current density (Jsc) and fill factor (FF). PDIs have two drawbacks: (1) the low LUMO level leads to low Voc; (2) PDIs with rigid planar structure tend to form excessive aggregations, affecting the formation of uniform films. Thus, lifting LUMO level and constructing non-coplanar perylene monoimides (PMIs) to improve Voc and the morphology are effective strategies. PMI-based nonfullerene acceptors and the photovoltaic performance are summarized in Fig. 1 and Table 1. In 2015, a nonfullerene acceptor PMI-F-PMI with a fluorene core and two PMI arms was reported. It presented a lift-up LUMO level around –3.54 eV, which matches well with that of P3HT donor to yield high Voc. P3HT:PMI-F-PMI solar cells gave an efficiency of 2.3%, with a Voc of 0.98 V, a Jsc of 5.61 mA/cm2, and an FF of 42.0%[24]. Later, Li et al. used a polymer donor PTZ1, obtaining a PCE of 6.0%, with a Voc of 1.30 V, a Jsc of 7.0 mA/cm2, and an FF of 63.5%[25]. The favorable morphology, efficient exciton dissociation, balanced carrier mobilities, and reduced charge recombination also contributed to the increase of Voc.

Figure  1.  The chemical structures for PMI-based non-planar acceptors.
Table  1.  Materials energy levels and the performance for solar cells.
PMI acceptor Polymer donorVoc
(V)
Jsc
(mA/cm2)
FF
(%)
PCE
(%)
Ref.
NameLUMO (eV)HOMO (eV) NameLUMO (eV)HOMO (eV)
PMI-F-PMI–3.54–5.74 P3HT–2.74–4.760.985.6142.02.30[24]
–3.42–5.50PTZ1–3.34–5.311.307.063.56.0[25]
PMI-FF-PMI–3.74–5.80D18–3.58–5.621.416.0960.95.34[26]
P-oPh-P–3.97–6.38 PBDB-T–3.41–5.211.042.62401.08[28]
P3-Ph–4.13–6.220.691.70460.54
P-HexPh-P–3.85–6.401.129.97462.02
P-DeOPh-P–3.92–6.311.007.46433.17
DownLoad: CSV  | Show Table

It is important to understand the effect of different aromatic core on the photovoltaic performance. In 2022, Scharber et al. developed a non-planar acceptor PMI-FF-PMI, consisting of two PMI units bridged with a dihydroindeno[1,2-b]fluorene unit. PMI-FF-PMI:D18 solar cells gave a PCE of 5.34%, with a Voc of 1.41 V, a Jsc of 6.09 mA/cm2, and an FF of 60.9%[26]. The 1.41 V Voc is the highest record for solution-processed OSCs so far. Though producing a high Voc, the cells presented a relatively large nonradiative voltage loss (ΔVocnon-rad) of 0.25 V, which mainly resulted from the enhancement of spontaneous carrier generation and the decrease of charge carrier in CT state process[27]. More recently, Trimmel et al. developed three PMI dimers by changing the substitution position (para, meta or ortho) on the benzene ring. Compared with P-pPh-P and P-mPh-P and P3Ph, P-oPh-P showed better solubility and device efficiency. With introducing two alkyl chains or alkoxy chains onto the benzene ring in P-pPh-P, three new PMI dimers were obtained, namely P-MePh-P, P-HexPh-P, P-DeOPh-P. P-HexPh-P and P-DeOPh-P with long chains exhibited higher crystallinity than P-MePh-P, and P-DeOPh-P with alkoxy chains presented a favorable face-on orientation as indicated by GIWAXS, which is beneficial to charge transport. As a result, PBDB-T:P-DeOPh-P cells offered a PCE of 3.17%, with a Voc of 1.00 V, a Jsc of 7.46 mA/cm2, and an FF of 43.0%[28]. Tuning the linking units is a simple approach to develop high-performance PMI-based acceptors.

In short, the Voc and PCE for NF-OSCs can be enhanced via tailoring the molecular structures of NFAs and donors. In order to regulate the morphology of the blends, different aromatic cores were introduced into PMI-based acceptors. The LUMO energy levels should also be tuned to match that of the donors.

This work was supported by the Scientific Research Foundation of Education Department of Jilin Province (JJKH20220827KJ), Natural Science Foundation of Changchun Normal University, and Scientific Startup Fund of Changchun Normal University. L. Ding thanks the National Key Research and Development Program of China (2017YFA0206600) and the National Natural Science Foundation of China (51773045, 21772030, 51922032, and 21961160720) for financial support.



[1]
Li C, Zhou J, Song J, et al. Non-fullerene acceptors with branched side chains and improved molecular packing to exceed 18% efficiency in organic solar cells. Nat Energy, 2021, 6, 605 doi: 10.1038/s41560-021-00820-x
[2]
Liu W, Xu X, Yuan J, et al. Low-bandgap non-fullerene acceptors enabling high-performance organic solar cells. ACS Energy Lett, 2021, 6, 598 doi: 10.1021/acsenergylett.0c02384
[3]
Ye L, Ye W, Zhang S. Recent advances and prospects of asymmetric non-fullerene small molecule acceptors for polymer solar cells. J Semicond, 2021, 42, 101607 doi: 10.1088/1674-4926/42/10/101607
[4]
Li S, Li C Z, Shi M, et al. New phase for organic solar cell research: emergence of Y-series electron acceptors and their perspectives. ACS Energy Lett, 2020, 5, 1554 doi: 10.1021/acsenergylett.0c00537
[5]
Tang A, Xiao Z, Ding L, et al. ~1.2 V open-circuit voltage from organic solar cells. J Semicond, 2021, 42, 070202 doi: 10.1088/1674-4926/42/7/070202
[6]
Jin K, Xiao Z, Ding L, 18. 69% PCE from organic solar cells. J Semicond, 2021, 42, 060502 doi: 10.1088/1674-4926/42/6/060502
[7]
Sun H, Liu B, Ma Y, et al. Regioregular narrow-bandgap n-type polymers with high electron mobility enabling highly efficient all-polymer solar cells. Adv Mater, 2021, 33, 2102635 doi: 10.1002/adma.202102635
[8]
Zhang Y, Shi L, Chen Y. Overview and outlook of random copolymerization strategy for designing polymer solar cells. Acta Polym Sin, 2019, 50, 13 doi: 10.11777/j.issn1000-3304.2018.18193
[9]
Liu T, Ma R, Luo Z, et al. Concurrent improvement in JSC and VOC in high-efficiency ternary organic solar cells enabled by a red-absorbing small-molecule acceptor with a high LUMO level. Energy Environ Sci, 2020, 13, 2115 doi: 10.1039/D0EE00662A
[10]
Duan C, Ding L. The new era for organic solar cells: non-fullerene small molecular acceptors. Sci Bull, 2020, 65, 1231 doi: 10.1016/j.scib.2020.04.030
[11]
Jin K, Xiao Z, Ding L. D18, an eximious solar polymer. J Semicond, 2021, 42, 010502 doi: 10.1088/1674-4926/42/1/010502
[12]
Meng X, Jin K, Xiao Z, et al. Side chain engineering on D18 polymers yields 18.74% power conversion efficiency. J Semicond, 2021, 42, 100501 doi: 10.1088/1674-4926/42/10/100501
[13]
Qin J, Zhang L, Zuo C, et al. A chlorinated copolymer donor demonstrates a 18.13% power conversion efficiency. J Semicond, 2021, 42, 010501 doi: 10.1088/1674-4926/42/1/010501
[14]
Cao J, Yi L, Ding L. The origin and evolution of Y6 structure. J Semicond, 2022, 43, 030202 doi: 10.1088/1674-4926/43/3/030202
[15]
Xu Y, Cui Y, Yao H, et al. A new conjugated polymer that enables the integration of photovoltaic and light-emitting functions in one device. Adv Mater, 2021, 33, 2101090 doi: 10.1002/adma.202101090
[16]
Xu X, Yu L, Meng H, et al. Polymer solar cells with 18.74% efficiency: from bulk heterojunction to interdigitated bulk heterojunction. Adv Funct Mater, 2022, 32, 2108797 doi: 10.1002/adfm.202108797
[17]
Liu Q, Jiang Y, Jin K, et al. 18% Efficiency organic solar cells. Sci Bull, 2020, 65, 272 doi: 10.1016/j.scib.2020.01.001
[18]
Cui Y, Xu Y, Yao H, et al. Single-junction organic photovoltaic cell with 19% efficiency. Adv Mater, 2021, 33, 2102420 doi: 10.1002/adma.202102420
[19]
He Y, Chen H Y, Hou J, et al. Indene-C60 bisadduct: a new acceptor for high-performance polymer solar cells. J Am Chem Soc, 2010, 132, 1377 doi: 10.1021/ja908602j
[20]
He Y, Zhao G, Peng B, et al. High-yield synthesis and electrochemical and photovoltaic properties of indene-C70 bisadduct. Adv Funct Mater, 2010, 20, 3383 doi: 10.1002/adfm.201001122
[21]
Li C, Wonneberger H. Perylene imides for organic photovoltaics: yesterday, today, and tomorrow. Adv Mater, 2012, 24, 613 doi: 10.1002/adma.201104447
[22]
Tang C W. Two-layer organic photovoltaic cell. Appl Phys Lett, 1986, 48, 183 doi: 10.1063/1.96937
[23]
Rajaram S, Shivanna R, Kandappa S K, et al. Nonplanar perylene diimides as potential alternatives to fullerenes in organic solar cells. J Phys Chem Lett, 2012, 3, 2405 doi: 10.1021/jz301047d
[24]
Zhang Y, Xiao Y, Xie Y, et al. Fluorene-centered perylene monoimides as potential non-fullerene acceptor in organic solar cells. Org Electron, 2015, 21, 184 doi: 10.1016/j.orgel.2015.03.017
[25]
Zhang Y, Guo X, Guo B, et al. Nonfullerene polymer solar cells based on a perylene monoimide acceptor with a high open-circuit voltage of 1.3 V. Adv Funct Mater, 2017, 27, 1603892 doi: 10.1002/adfm.201603892
[26]
Hofinger J, Weber S, Mayr F, et al. Wide-bandgap organic solar cells with a novel perylene-based non-fullerene acceptor enabling open-circuit voltages beyond 1.4 V. J Mater Chem A, 2022, 10, 2888 doi: 10.1039/D1TA09752K
[27]
Xu J, Jo S B, Chen X, et al. The molecular ordering and double-channel carrier generation of nonfullerene photovoltaics within multi-length-scale morphology. Adv Mater, 2022, 34, 2108317 doi: 10.1002/adma.202108317
[28]
Schweda B, Reinfelds M, Hofinger J, et al. Phenylene-bridged perylene monoimides as acceptors for organic solar cells – a study on the structure-properties relationship. Chem Eur J, 2022, in press doi: 10.1002/chem.202200276
Fig. 1.  The chemical structures for PMI-based non-planar acceptors.

Table 1.   Materials energy levels and the performance for solar cells.

PMI acceptor Polymer donorVoc
(V)
Jsc
(mA/cm2)
FF
(%)
PCE
(%)
Ref.
NameLUMO (eV)HOMO (eV) NameLUMO (eV)HOMO (eV)
PMI-F-PMI–3.54–5.74 P3HT–2.74–4.760.985.6142.02.30[24]
–3.42–5.50PTZ1–3.34–5.311.307.063.56.0[25]
PMI-FF-PMI–3.74–5.80D18–3.58–5.621.416.0960.95.34[26]
P-oPh-P–3.97–6.38 PBDB-T–3.41–5.211.042.62401.08[28]
P3-Ph–4.13–6.220.691.70460.54
P-HexPh-P–3.85–6.401.129.97462.02
P-DeOPh-P–3.92–6.311.007.46433.17
DownLoad: CSV
[1]
Li C, Zhou J, Song J, et al. Non-fullerene acceptors with branched side chains and improved molecular packing to exceed 18% efficiency in organic solar cells. Nat Energy, 2021, 6, 605 doi: 10.1038/s41560-021-00820-x
[2]
Liu W, Xu X, Yuan J, et al. Low-bandgap non-fullerene acceptors enabling high-performance organic solar cells. ACS Energy Lett, 2021, 6, 598 doi: 10.1021/acsenergylett.0c02384
[3]
Ye L, Ye W, Zhang S. Recent advances and prospects of asymmetric non-fullerene small molecule acceptors for polymer solar cells. J Semicond, 2021, 42, 101607 doi: 10.1088/1674-4926/42/10/101607
[4]
Li S, Li C Z, Shi M, et al. New phase for organic solar cell research: emergence of Y-series electron acceptors and their perspectives. ACS Energy Lett, 2020, 5, 1554 doi: 10.1021/acsenergylett.0c00537
[5]
Tang A, Xiao Z, Ding L, et al. ~1.2 V open-circuit voltage from organic solar cells. J Semicond, 2021, 42, 070202 doi: 10.1088/1674-4926/42/7/070202
[6]
Jin K, Xiao Z, Ding L, 18. 69% PCE from organic solar cells. J Semicond, 2021, 42, 060502 doi: 10.1088/1674-4926/42/6/060502
[7]
Sun H, Liu B, Ma Y, et al. Regioregular narrow-bandgap n-type polymers with high electron mobility enabling highly efficient all-polymer solar cells. Adv Mater, 2021, 33, 2102635 doi: 10.1002/adma.202102635
[8]
Zhang Y, Shi L, Chen Y. Overview and outlook of random copolymerization strategy for designing polymer solar cells. Acta Polym Sin, 2019, 50, 13 doi: 10.11777/j.issn1000-3304.2018.18193
[9]
Liu T, Ma R, Luo Z, et al. Concurrent improvement in JSC and VOC in high-efficiency ternary organic solar cells enabled by a red-absorbing small-molecule acceptor with a high LUMO level. Energy Environ Sci, 2020, 13, 2115 doi: 10.1039/D0EE00662A
[10]
Duan C, Ding L. The new era for organic solar cells: non-fullerene small molecular acceptors. Sci Bull, 2020, 65, 1231 doi: 10.1016/j.scib.2020.04.030
[11]
Jin K, Xiao Z, Ding L. D18, an eximious solar polymer. J Semicond, 2021, 42, 010502 doi: 10.1088/1674-4926/42/1/010502
[12]
Meng X, Jin K, Xiao Z, et al. Side chain engineering on D18 polymers yields 18.74% power conversion efficiency. J Semicond, 2021, 42, 100501 doi: 10.1088/1674-4926/42/10/100501
[13]
Qin J, Zhang L, Zuo C, et al. A chlorinated copolymer donor demonstrates a 18.13% power conversion efficiency. J Semicond, 2021, 42, 010501 doi: 10.1088/1674-4926/42/1/010501
[14]
Cao J, Yi L, Ding L. The origin and evolution of Y6 structure. J Semicond, 2022, 43, 030202 doi: 10.1088/1674-4926/43/3/030202
[15]
Xu Y, Cui Y, Yao H, et al. A new conjugated polymer that enables the integration of photovoltaic and light-emitting functions in one device. Adv Mater, 2021, 33, 2101090 doi: 10.1002/adma.202101090
[16]
Xu X, Yu L, Meng H, et al. Polymer solar cells with 18.74% efficiency: from bulk heterojunction to interdigitated bulk heterojunction. Adv Funct Mater, 2022, 32, 2108797 doi: 10.1002/adfm.202108797
[17]
Liu Q, Jiang Y, Jin K, et al. 18% Efficiency organic solar cells. Sci Bull, 2020, 65, 272 doi: 10.1016/j.scib.2020.01.001
[18]
Cui Y, Xu Y, Yao H, et al. Single-junction organic photovoltaic cell with 19% efficiency. Adv Mater, 2021, 33, 2102420 doi: 10.1002/adma.202102420
[19]
He Y, Chen H Y, Hou J, et al. Indene-C60 bisadduct: a new acceptor for high-performance polymer solar cells. J Am Chem Soc, 2010, 132, 1377 doi: 10.1021/ja908602j
[20]
He Y, Zhao G, Peng B, et al. High-yield synthesis and electrochemical and photovoltaic properties of indene-C70 bisadduct. Adv Funct Mater, 2010, 20, 3383 doi: 10.1002/adfm.201001122
[21]
Li C, Wonneberger H. Perylene imides for organic photovoltaics: yesterday, today, and tomorrow. Adv Mater, 2012, 24, 613 doi: 10.1002/adma.201104447
[22]
Tang C W. Two-layer organic photovoltaic cell. Appl Phys Lett, 1986, 48, 183 doi: 10.1063/1.96937
[23]
Rajaram S, Shivanna R, Kandappa S K, et al. Nonplanar perylene diimides as potential alternatives to fullerenes in organic solar cells. J Phys Chem Lett, 2012, 3, 2405 doi: 10.1021/jz301047d
[24]
Zhang Y, Xiao Y, Xie Y, et al. Fluorene-centered perylene monoimides as potential non-fullerene acceptor in organic solar cells. Org Electron, 2015, 21, 184 doi: 10.1016/j.orgel.2015.03.017
[25]
Zhang Y, Guo X, Guo B, et al. Nonfullerene polymer solar cells based on a perylene monoimide acceptor with a high open-circuit voltage of 1.3 V. Adv Funct Mater, 2017, 27, 1603892 doi: 10.1002/adfm.201603892
[26]
Hofinger J, Weber S, Mayr F, et al. Wide-bandgap organic solar cells with a novel perylene-based non-fullerene acceptor enabling open-circuit voltages beyond 1.4 V. J Mater Chem A, 2022, 10, 2888 doi: 10.1039/D1TA09752K
[27]
Xu J, Jo S B, Chen X, et al. The molecular ordering and double-channel carrier generation of nonfullerene photovoltaics within multi-length-scale morphology. Adv Mater, 2022, 34, 2108317 doi: 10.1002/adma.202108317
[28]
Schweda B, Reinfelds M, Hofinger J, et al. Phenylene-bridged perylene monoimides as acceptors for organic solar cells – a study on the structure-properties relationship. Chem Eur J, 2022, in press doi: 10.1002/chem.202200276
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    Received: 24 March 2022 Revised: Online: Accepted Manuscript: 30 March 2022Uncorrected proof: 30 March 2022Published: 01 May 2022

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      Yutong Ji, Helong Bai, Lixiu Zhang, Youdi Zhang, Liming Ding. Nonfullerene acceptors based on perylene monoimides[J]. Journal of Semiconductors, 2022, 43(5): 050203. doi: 10.1088/1674-4926/43/5/050203 ****Y T Ji, H L Bai, L X Zhang, Y D Zhang, L M Ding. Nonfullerene acceptors based on perylene monoimides[J]. J. Semicond, 2022, 43(5): 050203. doi: 10.1088/1674-4926/43/5/050203
      Citation:
      Yutong Ji, Helong Bai, Lixiu Zhang, Youdi Zhang, Liming Ding. Nonfullerene acceptors based on perylene monoimides[J]. Journal of Semiconductors, 2022, 43(5): 050203. doi: 10.1088/1674-4926/43/5/050203 ****
      Y T Ji, H L Bai, L X Zhang, Y D Zhang, L M Ding. Nonfullerene acceptors based on perylene monoimides[J]. J. Semicond, 2022, 43(5): 050203. doi: 10.1088/1674-4926/43/5/050203

      Nonfullerene acceptors based on perylene monoimides

      DOI: 10.1088/1674-4926/43/5/050203
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      • Yutong Ji:got her BS from Changchun Normal University in 2021. Now she is a master student at Changchun Normal University under the supervision of Professor Youdi Zhang. Her research focuses on the design and synthesis of organic functional molecules
      • Helong Bai:got his BS in 2005 and master degree in 2010 from Changchun Normal University. He got PhD from Jilin University in 2017, then he joined Shugeng Cao Group at University of Hawaii as a visiting scholar. He joined Changchun Normal University as an associate professor in 2017. His research is on secondary metabolites of endophytic fungi and natural product analysis
      • Lixiu Zhang:got her BS degree from Soochow University in 2019. Now she is a PhD student at University of Chinese Academy of Sciences under the supervision of Prof. Liming Ding. Her research focuses on perovskite solar cells
      • Youdi Zhang:is currently an associate professor in College of Chemistry at Changchun Normal University. He received his PhD from Dalian University of Technology in 2014. Then he joined Yongfang Li Group at Soochow University as a postdoc (2014–2016). He worked in Yiwang Chen Group at Nanchang University as an assistant professor in 2016–2021. He worked in Changduk Yang Group at Ulsan National Institute of Science and Technology (UNIST) as a research assistant professor in 2019–2020. His research focuses on the design and synthesis of non-fullerene fused-ring acceptors for organic photovoltaics
      • Liming Ding:got his PhD from University of Science and Technology of China (was a joint student at Changchun Institute of Applied Chemistry, CAS). He started his research on OSCs and PLEDs in Olle Ingans Lab in 1998. Later on, he worked at National Center for Polymer Research, Wright-Patterson Air Force Base and Argonne National Lab (USA). He joined Konarka as a Senior Scientist in 2008. In 2010, he joined National Center for Nanoscience and Technology as a full professor. His research focuses on innovative materials and devices. He is RSC Fellow, the nominator for Xplorer Prize, and the Associate Editor for Journal of Semiconductors
      • Corresponding author: zhangyd@ccsfu.edu.cnding@nanoctr.cn
      • Received Date: 2022-03-24
        Available Online: 2022-03-30

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