Nonfullerene acceptors based on perylene monoimides

Yutong Ji; Helong Bai; Lixiu Zhang; Youdi Zhang; Liming Ding

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

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

RESEARCH HIGHLIGHTS

Nonfullerene acceptors based on perylene monoimides

Yutong Ji^{1, 2}, Helong Bai^{1, 2}, Lixiu Zhang³, Youdi Zhang^{1, 2,} and Liming Ding^3,

+ Author Affiliations

1. College of Chemistry, Changchun Normal University, Changchun 130032, China
2. Key Laboratory of Advanced Green Functional Materials, Changchun Normal University, Changchun 130032, China
3. Center for Excellence in Nanoscience (CAS), Key Laboratory of Nanosystem and Hierarchical Fabrication (CAS), National Center for Nanoscience and Technology, Beijing 100190, China

Author Bio:

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

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

References

[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 J_SC and V_OC 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.

DownLoad: Full-Size Img PowerPoint

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

PMI acceptor			Polymer donor			V_oc (V)	J_sc (mA/cm²)	FF (%)	PCE (%)	Ref.
Name	LUMO (eV)	HOMO (eV)	Name	LUMO (eV)	HOMO (eV)	V_oc (V)	J_sc (mA/cm²)	FF (%)	PCE (%)	Ref.
PMI-F-PMI	–3.54	–5.74	P3HT	–2.74	–4.76	0.98	5.61	42.0	2.30	[24]
PMI-F-PMI	–3.42	–5.50	PTZ1	–3.34	–5.31	1.30	7.0	63.5	6.0	[25]
PMI-FF-PMI	–3.74	–5.80	D18	–3.58	–5.62	1.41	6.09	60.9	5.34	[26]
P-oPh-P	–3.97	–6.38	PBDB-T	–3.41	–5.21	1.04	2.62	40	1.08	[28]
P3-Ph	–4.13	–6.22				0.69	1.70	46	0.54
P-HexPh-P	–3.85	–6.40				1.12	9.97	46	2.02
P-DeOPh-P	–3.92	–6.31				1.00	7.46	43	3.17

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 J_SC and V_OC 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