18.9% Efficient Organic Solar Cells Based on n-Doped Bulk-Heterojunction and Halogen-Substituted Self-Assembled Monolayers as Hole Extracting Interlayers

Yuanbao Lin; Yadong Zhang; Junxiang Zhang; Mantas Marcinskas; Tadas Malinauskas; Artiom Magomedov; Mohamad Insan Nugraha; Dimitris Kaltsas; Dipti R. Naphade; George T. Harrison; Abdulrahman El-Labban; Stephen Barlow; Stefaan De Wolf; Ergang Wang; Iain McCulloch; Leonidas Tsetseris; Vytautas Getautis; Seth R. Marder; Thomas D. Anthopoulos

doi:10.1002/aenm.202202503

18.9% Efficient Organic Solar Cells Based on n-Doped Bulk-Heterojunction and Halogen-Substituted Self-Assembled Monolayers as Hole Extracting Interlayers

Yuanbao Lin^*, Yadong Zhang, Junxiang Zhang, Mantas Marcinskas, Tadas Malinauskas, Artiom Magomedov, Mohamad Insan Nugraha, Dimitris Kaltsas, Dipti R. Naphade, George T. Harrison, Abdulrahman El-Labban, Stephen Barlow, Stefaan De Wolf, Ergang Wang, Iain McCulloch, Leonidas Tsetseris, Vytautas Getautis^*, Seth R. Marder^*, Thomas D. Anthopoulos^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

The influence of halogen substitutions (F, Cl, Br, and I) on the energy levels of the self-assembled hole-extracting molecule [2-(9H-Carbazol-9-yl)ethyl]phosphonic acid (2PACz), is investigated. It is found that the formation of self-assembled monolayers (SAMs) of [2-(3,6-Difluoro-9H-carbazol-9-yl)ethyl]phosphonic acid (F-2PACz), [2-(3,6-Dichloro-9H-carbazol-9-yl)ethyl]phosphonic acid (Cl-2PACz), [2-(3,6-Dibromo-9H-carbazol-9-yl)ethyl]phosphonic acid (Br-2PACz), and [2-(3,6-Diiodo-9H-carbazol-9-yl)ethyl]phosphonic acid (I-2PACz) directly on indium tin oxide (ITO) increases its work function from 4.73 eV to 5.68, 5.77, 5.82, and 5.73 eV, respectively. Combining these ITO/SAM electrodes with the ternary bulk-heterojunction (BHJ) system PM6:PM7-Si:BTP-eC9 yields organic photovoltaic (OPV) cells with power conversion efficiency (PCE) in the range of 17.7%–18.5%. OPVs featuring Cl-2PACz SAMs yield the highest PCE of 18.5%, compared to cells with F-2PACz (17.7%), Br-2PACz (18.0%), or I-2PACz (18.2%). Data analysis reveals that the enhanced performance of Cl-2PACz-based OPVs relates to the increased hole mobility, decreased interface resistance, reduced carrier recombination, and longer carrier lifetime. Furthermore, OPVs featuring Cl-2PACz show enhanced stability under continuous illumination compared to ITO/PEDOT:PSS-based cells. Remarkably, the introduction of the n-dopant benzyl viologen into the BHJ further boosted the PCE of the ITO/Cl-2PACz cells to a maximum value of 18.9%, a record-breaking value for SAM-based OPVs and on par with the best-performing OPVs reported to date.

Original language	English (US)
Article number	2202503
Journal	Advanced Energy Materials
Volume	12
Issue number	45
DOIs	https://doi.org/10.1002/aenm.202202503
State	Published - Dec 1 2022

Bibliographical note

Funding Information:
This publication was based upon work supported by the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under Awards No: OSR‐2018‐CARF/CCF‐3079 and No: OSR‐2019‐CRG8‐4095.3. J.Z., Y.Z., S.B., and S.R.M. acknowledged funding from NSF under the CCI Center for Selective C–H Functionalization (CHE‐1700982) and from the Department of the Navy, Office of Naval Research as part of a Multidisciplinary University Research Initiative, Award No., N00014‐21‐1‐2180. A.M. and VG acknowledged funding from the Research Council of Lithuania under grant agreement Nr. 01.2.2‐LMT‐K‐718‐03‐0040 (SMARTMOLECULES). D.K. and L.T. acknowledged support for the computational time granted from GRNET in the National HPC facility ‐ARIS – under project FRAME. Y.L. and I.M. acknowledged funding from the European Union's Horizon 2020 research and innovation program under grant agreement n 952911, project BOOSTER, grant agreement n°862474, project RoLA‐FLEX, and grant agreement n°101007084 CITYSOLAR, as well as EPSRC Project EP/T026219/1 EP/W017091/1.

Funding Information:
This publication was based upon work supported by the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under Awards No: OSR-2018-CARF/CCF-3079 and No: OSR-2019-CRG8-4095.3. J.Z., Y.Z., S.B., and S.R.M. acknowledged funding from NSF under the CCI Center for Selective C–H Functionalization (CHE-1700982) and from the Department of the Navy, Office of Naval Research as part of a Multidisciplinary University Research Initiative, Award No., N00014-21-1-2180. A.M. and VG acknowledged funding from the Research Council of Lithuania under grant agreement Nr. 01.2.2-LMT-K-718-03-0040 (SMARTMOLECULES). D.K. and L.T. acknowledged support for the computational time granted from GRNET in the National HPC facility -ARIS – under project FRAME. Y.L. and I.M. acknowledged funding from the European Union's Horizon 2020 research and innovation program under grant agreement n 952911, project BOOSTER, grant agreement n°862474, project RoLA-FLEX, and grant agreement n°101007084 CITYSOLAR, as well as EPSRC Project EP/T026219/1 EP/W017091/1.

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

Keywords

molecular dopants
organic bulk-heterojunctions
organic semiconductors
organic solar cells
self-assembled monolayers
solution processing

ASJC Scopus subject areas

Renewable Energy, Sustainability and the Environment
Materials Science(all)

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/aenm.202202503

Cite this

Lin, Y., Zhang, Y., Zhang, J., Marcinskas, M., Malinauskas, T., Magomedov, A., Nugraha, M. I., Kaltsas, D., Naphade, D. R., Harrison, G. T., El-Labban, A., Barlow, S., De Wolf, S., Wang, E., McCulloch, I., Tsetseris, L., Getautis, V., Marder, S. R., & Anthopoulos, T. D. (2022). 18.9% Efficient Organic Solar Cells Based on n-Doped Bulk-Heterojunction and Halogen-Substituted Self-Assembled Monolayers as Hole Extracting Interlayers. Advanced Energy Materials, 12(45), Article 2202503. https://doi.org/10.1002/aenm.202202503

@article{756c11c0533a4a12b813fe868eebc357,

title = "18.9% Efficient Organic Solar Cells Based on n-Doped Bulk-Heterojunction and Halogen-Substituted Self-Assembled Monolayers as Hole Extracting Interlayers",

abstract = "The influence of halogen substitutions (F, Cl, Br, and I) on the energy levels of the self-assembled hole-extracting molecule [2-(9H-Carbazol-9-yl)ethyl]phosphonic acid (2PACz), is investigated. It is found that the formation of self-assembled monolayers (SAMs) of [2-(3,6-Difluoro-9H-carbazol-9-yl)ethyl]phosphonic acid (F-2PACz), [2-(3,6-Dichloro-9H-carbazol-9-yl)ethyl]phosphonic acid (Cl-2PACz), [2-(3,6-Dibromo-9H-carbazol-9-yl)ethyl]phosphonic acid (Br-2PACz), and [2-(3,6-Diiodo-9H-carbazol-9-yl)ethyl]phosphonic acid (I-2PACz) directly on indium tin oxide (ITO) increases its work function from 4.73 eV to 5.68, 5.77, 5.82, and 5.73 eV, respectively. Combining these ITO/SAM electrodes with the ternary bulk-heterojunction (BHJ) system PM6:PM7-Si:BTP-eC9 yields organic photovoltaic (OPV) cells with power conversion efficiency (PCE) in the range of 17.7%–18.5%. OPVs featuring Cl-2PACz SAMs yield the highest PCE of 18.5%, compared to cells with F-2PACz (17.7%), Br-2PACz (18.0%), or I-2PACz (18.2%). Data analysis reveals that the enhanced performance of Cl-2PACz-based OPVs relates to the increased hole mobility, decreased interface resistance, reduced carrier recombination, and longer carrier lifetime. Furthermore, OPVs featuring Cl-2PACz show enhanced stability under continuous illumination compared to ITO/PEDOT:PSS-based cells. Remarkably, the introduction of the n-dopant benzyl viologen into the BHJ further boosted the PCE of the ITO/Cl-2PACz cells to a maximum value of 18.9%, a record-breaking value for SAM-based OPVs and on par with the best-performing OPVs reported to date.",

keywords = "molecular dopants, organic bulk-heterojunctions, organic semiconductors, organic solar cells, self-assembled monolayers, solution processing",

author = "Yuanbao Lin and Yadong Zhang and Junxiang Zhang and Mantas Marcinskas and Tadas Malinauskas and Artiom Magomedov and Nugraha, {Mohamad Insan} and Dimitris Kaltsas and Naphade, {Dipti R.} and Harrison, {George T.} and Abdulrahman El-Labban and Stephen Barlow and {De Wolf}, Stefaan and Ergang Wang and Iain McCulloch and Leonidas Tsetseris and Vytautas Getautis and Marder, {Seth R.} and Anthopoulos, {Thomas D.}",

note = "Funding Information: This publication was based upon work supported by the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under Awards No: OSR‐2018‐CARF/CCF‐3079 and No: OSR‐2019‐CRG8‐4095.3. J.Z., Y.Z., S.B., and S.R.M. acknowledged funding from NSF under the CCI Center for Selective C–H Functionalization (CHE‐1700982) and from the Department of the Navy, Office of Naval Research as part of a Multidisciplinary University Research Initiative, Award No., N00014‐21‐1‐2180. A.M. and VG acknowledged funding from the Research Council of Lithuania under grant agreement Nr. 01.2.2‐LMT‐K‐718‐03‐0040 (SMARTMOLECULES). D.K. and L.T. acknowledged support for the computational time granted from GRNET in the National HPC facility ‐ARIS – under project FRAME. Y.L. and I.M. acknowledged funding from the European Union's Horizon 2020 research and innovation program under grant agreement n 952911, project BOOSTER, grant agreement n°862474, project RoLA‐FLEX, and grant agreement n°101007084 CITYSOLAR, as well as EPSRC Project EP/T026219/1 EP/W017091/1. Funding Information: This publication was based upon work supported by the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under Awards No: OSR-2018-CARF/CCF-3079 and No: OSR-2019-CRG8-4095.3. J.Z., Y.Z., S.B., and S.R.M. acknowledged funding from NSF under the CCI Center for Selective C–H Functionalization (CHE-1700982) and from the Department of the Navy, Office of Naval Research as part of a Multidisciplinary University Research Initiative, Award No., N00014-21-1-2180. A.M. and VG acknowledged funding from the Research Council of Lithuania under grant agreement Nr. 01.2.2-LMT-K-718-03-0040 (SMARTMOLECULES). D.K. and L.T. acknowledged support for the computational time granted from GRNET in the National HPC facility -ARIS – under project FRAME. Y.L. and I.M. acknowledged funding from the European Union's Horizon 2020 research and innovation program under grant agreement n 952911, project BOOSTER, grant agreement n°862474, project RoLA-FLEX, and grant agreement n°101007084 CITYSOLAR, as well as EPSRC Project EP/T026219/1 EP/W017091/1. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = dec,

day = "1",

doi = "10.1002/aenm.202202503",

language = "English (US)",

volume = "12",

journal = "Advanced Energy Materials",

issn = "1614-6832",

publisher = "Wiley-VCH Verlag",

number = "45",

}

Lin, Y, Zhang, Y, Zhang, J, Marcinskas, M, Malinauskas, T, Magomedov, A, Nugraha, MI, Kaltsas, D, Naphade, DR, Harrison, GT , El-Labban, A, Barlow, S, De Wolf, S, Wang, E, McCulloch, I, Tsetseris, L, Getautis, V, Marder, SR & Anthopoulos, TD 2022, '18.9% Efficient Organic Solar Cells Based on n-Doped Bulk-Heterojunction and Halogen-Substituted Self-Assembled Monolayers as Hole Extracting Interlayers', Advanced Energy Materials, vol. 12, no. 45, 2202503. https://doi.org/10.1002/aenm.202202503

TY - JOUR

T1 - 18.9% Efficient Organic Solar Cells Based on n-Doped Bulk-Heterojunction and Halogen-Substituted Self-Assembled Monolayers as Hole Extracting Interlayers

AU - Lin, Yuanbao

AU - Zhang, Yadong

AU - Zhang, Junxiang

AU - Marcinskas, Mantas

AU - Malinauskas, Tadas

AU - Magomedov, Artiom

AU - Nugraha, Mohamad Insan

AU - Kaltsas, Dimitris

AU - Naphade, Dipti R.

AU - Harrison, George T.

AU - El-Labban, Abdulrahman

AU - Barlow, Stephen

AU - De Wolf, Stefaan

AU - Wang, Ergang

AU - McCulloch, Iain

AU - Tsetseris, Leonidas

AU - Getautis, Vytautas

AU - Marder, Seth R.

AU - Anthopoulos, Thomas D.

N1 - Funding Information: This publication was based upon work supported by the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under Awards No: OSR‐2018‐CARF/CCF‐3079 and No: OSR‐2019‐CRG8‐4095.3. J.Z., Y.Z., S.B., and S.R.M. acknowledged funding from NSF under the CCI Center for Selective C–H Functionalization (CHE‐1700982) and from the Department of the Navy, Office of Naval Research as part of a Multidisciplinary University Research Initiative, Award No., N00014‐21‐1‐2180. A.M. and VG acknowledged funding from the Research Council of Lithuania under grant agreement Nr. 01.2.2‐LMT‐K‐718‐03‐0040 (SMARTMOLECULES). D.K. and L.T. acknowledged support for the computational time granted from GRNET in the National HPC facility ‐ARIS – under project FRAME. Y.L. and I.M. acknowledged funding from the European Union's Horizon 2020 research and innovation program under grant agreement n 952911, project BOOSTER, grant agreement n°862474, project RoLA‐FLEX, and grant agreement n°101007084 CITYSOLAR, as well as EPSRC Project EP/T026219/1 EP/W017091/1. Funding Information: This publication was based upon work supported by the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under Awards No: OSR-2018-CARF/CCF-3079 and No: OSR-2019-CRG8-4095.3. J.Z., Y.Z., S.B., and S.R.M. acknowledged funding from NSF under the CCI Center for Selective C–H Functionalization (CHE-1700982) and from the Department of the Navy, Office of Naval Research as part of a Multidisciplinary University Research Initiative, Award No., N00014-21-1-2180. A.M. and VG acknowledged funding from the Research Council of Lithuania under grant agreement Nr. 01.2.2-LMT-K-718-03-0040 (SMARTMOLECULES). D.K. and L.T. acknowledged support for the computational time granted from GRNET in the National HPC facility -ARIS – under project FRAME. Y.L. and I.M. acknowledged funding from the European Union's Horizon 2020 research and innovation program under grant agreement n 952911, project BOOSTER, grant agreement n°862474, project RoLA-FLEX, and grant agreement n°101007084 CITYSOLAR, as well as EPSRC Project EP/T026219/1 EP/W017091/1. Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022/12/1

Y1 - 2022/12/1

N2 - The influence of halogen substitutions (F, Cl, Br, and I) on the energy levels of the self-assembled hole-extracting molecule [2-(9H-Carbazol-9-yl)ethyl]phosphonic acid (2PACz), is investigated. It is found that the formation of self-assembled monolayers (SAMs) of [2-(3,6-Difluoro-9H-carbazol-9-yl)ethyl]phosphonic acid (F-2PACz), [2-(3,6-Dichloro-9H-carbazol-9-yl)ethyl]phosphonic acid (Cl-2PACz), [2-(3,6-Dibromo-9H-carbazol-9-yl)ethyl]phosphonic acid (Br-2PACz), and [2-(3,6-Diiodo-9H-carbazol-9-yl)ethyl]phosphonic acid (I-2PACz) directly on indium tin oxide (ITO) increases its work function from 4.73 eV to 5.68, 5.77, 5.82, and 5.73 eV, respectively. Combining these ITO/SAM electrodes with the ternary bulk-heterojunction (BHJ) system PM6:PM7-Si:BTP-eC9 yields organic photovoltaic (OPV) cells with power conversion efficiency (PCE) in the range of 17.7%–18.5%. OPVs featuring Cl-2PACz SAMs yield the highest PCE of 18.5%, compared to cells with F-2PACz (17.7%), Br-2PACz (18.0%), or I-2PACz (18.2%). Data analysis reveals that the enhanced performance of Cl-2PACz-based OPVs relates to the increased hole mobility, decreased interface resistance, reduced carrier recombination, and longer carrier lifetime. Furthermore, OPVs featuring Cl-2PACz show enhanced stability under continuous illumination compared to ITO/PEDOT:PSS-based cells. Remarkably, the introduction of the n-dopant benzyl viologen into the BHJ further boosted the PCE of the ITO/Cl-2PACz cells to a maximum value of 18.9%, a record-breaking value for SAM-based OPVs and on par with the best-performing OPVs reported to date.

AB - The influence of halogen substitutions (F, Cl, Br, and I) on the energy levels of the self-assembled hole-extracting molecule [2-(9H-Carbazol-9-yl)ethyl]phosphonic acid (2PACz), is investigated. It is found that the formation of self-assembled monolayers (SAMs) of [2-(3,6-Difluoro-9H-carbazol-9-yl)ethyl]phosphonic acid (F-2PACz), [2-(3,6-Dichloro-9H-carbazol-9-yl)ethyl]phosphonic acid (Cl-2PACz), [2-(3,6-Dibromo-9H-carbazol-9-yl)ethyl]phosphonic acid (Br-2PACz), and [2-(3,6-Diiodo-9H-carbazol-9-yl)ethyl]phosphonic acid (I-2PACz) directly on indium tin oxide (ITO) increases its work function from 4.73 eV to 5.68, 5.77, 5.82, and 5.73 eV, respectively. Combining these ITO/SAM electrodes with the ternary bulk-heterojunction (BHJ) system PM6:PM7-Si:BTP-eC9 yields organic photovoltaic (OPV) cells with power conversion efficiency (PCE) in the range of 17.7%–18.5%. OPVs featuring Cl-2PACz SAMs yield the highest PCE of 18.5%, compared to cells with F-2PACz (17.7%), Br-2PACz (18.0%), or I-2PACz (18.2%). Data analysis reveals that the enhanced performance of Cl-2PACz-based OPVs relates to the increased hole mobility, decreased interface resistance, reduced carrier recombination, and longer carrier lifetime. Furthermore, OPVs featuring Cl-2PACz show enhanced stability under continuous illumination compared to ITO/PEDOT:PSS-based cells. Remarkably, the introduction of the n-dopant benzyl viologen into the BHJ further boosted the PCE of the ITO/Cl-2PACz cells to a maximum value of 18.9%, a record-breaking value for SAM-based OPVs and on par with the best-performing OPVs reported to date.

KW - molecular dopants

KW - organic bulk-heterojunctions

KW - organic semiconductors

KW - organic solar cells

KW - self-assembled monolayers

KW - solution processing

UR - http://www.scopus.com/inward/record.url?scp=85139219556&partnerID=8YFLogxK

U2 - 10.1002/aenm.202202503

DO - 10.1002/aenm.202202503

M3 - Article

AN - SCOPUS:85139219556

SN - 1614-6832

VL - 12

JO - Advanced Energy Materials

JF - Advanced Energy Materials

IS - 45

M1 - 2202503

ER -

18.9% Efficient Organic Solar Cells Based on n-Doped Bulk-Heterojunction and Halogen-Substituted Self-Assembled Monolayers as Hole Extracting Interlayers

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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