Naphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiency

Astrid Caroline Knall; Raja Shahid Ashraf; Mark Nikolka; Christian B. Nielsen; Balaji Purushothaman; Aditya Sadhanala; Michael Hurhangee; Katharina Broch; David J. Harkin; Jiří Novák; Marios Neophytou; Pascal Hayoz; Henning Sirringhaus; Iain McCulloch

doi:10.1002/adfm.201602285

Naphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiency

Astrid Caroline Knall, Raja Shahid Ashraf, Mark Nikolka, Christian B. Nielsen, Balaji Purushothaman, Aditya Sadhanala, Michael Hurhangee, Katharina Broch, David J. Harkin, Jiří Novák, Marios Neophytou, Pascal Hayoz, Henning Sirringhaus, Iain McCulloch

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18 Scopus citations

Abstract

Wide-bandgap conjugated polymers with a linear naphthacenodithiophene (NDT) donor unit are herein reported along with their performance in both transistor and solar cell devices. The monomer is synthesized starting from 2,6-dihydroxynaphthalene with a double Fries rearrangement as the key step. By copolymerization with 2,1,3-benzothiadiazole (BT) via a palladium-catalyzed Suzuki coupling reaction, NDT-BT co-polymers with high molecular weights and narrow polydispersities are afforded. These novel wide-bandgap polymers are evaluated as the semiconducting polymer in both organic field effect transistor and organic photovoltaic applications. The synthesized polymers reveal an optical bandgap in the range of 1.8 eV with an electron affinity of 3.6 eV which provides sufficient energy offset for electron transfer to PC70BM acceptors. In organic field effect transistors, the synthesized polymers demonstrate high hole mobilities of around 0.4 cm2 V–1 s–1. By using a blend of NDT-BT with PC70BM as absorber layer in organic bulk heterojunction solar cells, power conversion efficiencies of 7.5% are obtained. This value is among the highest obtained for polymers with a wider bandgap (larger than 1.7 eV), making this polymer also interesting for application in tandem or multijunction solar cells. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Original language	English (US)
Pages (from-to)	6961-6969
Number of pages	9
Journal	Advanced Functional Materials
Volume	26
Issue number	38
DOIs	https://doi.org/10.1002/adfm.201602285
State	Published - Aug 18 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work was carried out with financial support from BASF. Funding is gratefully acknowledged from Austrian Science Fund (FWF): T578-N19, EC FP7 Project SC2 (610115), EC FP7 Project ArtESun (604397), EPSRC EP/G037515/1, and EPSRC EP/M005143/1. The authors thank Dr. T. Arnold, Diamond Light Source, Didcot, UK and J. Rozbořil, Masaryk University, Brno, Czech Republic for assistance with the GIWAXS-measurements. Financial support from Diamond Light Source is gratefully acknowledged. K. B. gratefully acknowledges financial support from the German Research Foundation (BR 4869/1-1). J. N. acknowledges support from the project CEITEC 2020 (grant No. LQ1601 financed by the MEYS of the Czech Republic).

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10.1002/adfm.201602285

https://repository.kaust.edu.sa/bitstream/10754/622111/1/PDFsam_Nielsen%20Naphthacenodithiophene%20Based%20Polymers%202016%20Accepted.pdf

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Knall, A. C., Ashraf, R. S., Nikolka, M., Nielsen, C. B., Purushothaman, B., Sadhanala, A., Hurhangee, M., Broch, K., Harkin, D. J., Novák, J., Neophytou, M., Hayoz, P., Sirringhaus, H., & McCulloch, I. (2016). Naphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiency. Advanced Functional Materials, 26(38), 6961-6969. https://doi.org/10.1002/adfm.201602285

@article{5c3ab0cc3a714ca4b5ff61d34644d80f,

title = "Naphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiency",

abstract = "Wide-bandgap conjugated polymers with a linear naphthacenodithiophene (NDT) donor unit are herein reported along with their performance in both transistor and solar cell devices. The monomer is synthesized starting from 2,6-dihydroxynaphthalene with a double Fries rearrangement as the key step. By copolymerization with 2,1,3-benzothiadiazole (BT) via a palladium-catalyzed Suzuki coupling reaction, NDT-BT co-polymers with high molecular weights and narrow polydispersities are afforded. These novel wide-bandgap polymers are evaluated as the semiconducting polymer in both organic field effect transistor and organic photovoltaic applications. The synthesized polymers reveal an optical bandgap in the range of 1.8 eV with an electron affinity of 3.6 eV which provides sufficient energy offset for electron transfer to PC70BM acceptors. In organic field effect transistors, the synthesized polymers demonstrate high hole mobilities of around 0.4 cm2 V–1 s–1. By using a blend of NDT-BT with PC70BM as absorber layer in organic bulk heterojunction solar cells, power conversion efficiencies of 7.5% are obtained. This value is among the highest obtained for polymers with a wider bandgap (larger than 1.7 eV), making this polymer also interesting for application in tandem or multijunction solar cells. {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

author = "Knall, {Astrid Caroline} and Ashraf, {Raja Shahid} and Mark Nikolka and Nielsen, {Christian B.} and Balaji Purushothaman and Aditya Sadhanala and Michael Hurhangee and Katharina Broch and Harkin, {David J.} and Ji{\v r}{\'i} Nov{\'a}k and Marios Neophytou and Pascal Hayoz and Henning Sirringhaus and Iain McCulloch",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was carried out with financial support from BASF. Funding is gratefully acknowledged from Austrian Science Fund (FWF): T578-N19, EC FP7 Project SC2 (610115), EC FP7 Project ArtESun (604397), EPSRC EP/G037515/1, and EPSRC EP/M005143/1. The authors thank Dr. T. Arnold, Diamond Light Source, Didcot, UK and J. Rozbo{\v r}il, Masaryk University, Brno, Czech Republic for assistance with the GIWAXS-measurements. Financial support from Diamond Light Source is gratefully acknowledged. K. B. gratefully acknowledges financial support from the German Research Foundation (BR 4869/1-1). J. N. acknowledges support from the project CEITEC 2020 (grant No. LQ1601 financed by the MEYS of the Czech Republic).",

year = "2016",

month = aug,

day = "18",

doi = "10.1002/adfm.201602285",

language = "English (US)",

volume = "26",

pages = "6961--6969",

journal = "Advanced Functional Materials",

issn = "1616-301X",

publisher = "Wiley",

number = "38",

}

Knall, AC, Ashraf, RS, Nikolka, M, Nielsen, CB, Purushothaman, B, Sadhanala, A, Hurhangee, M, Broch, K, Harkin, DJ, Novák, J, Neophytou, M, Hayoz, P, Sirringhaus, H & McCulloch, I 2016, 'Naphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiency', Advanced Functional Materials, vol. 26, no. 38, pp. 6961-6969. https://doi.org/10.1002/adfm.201602285

TY - JOUR

T1 - Naphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiency

AU - Knall, Astrid Caroline

AU - Ashraf, Raja Shahid

AU - Nikolka, Mark

AU - Nielsen, Christian B.

AU - Purushothaman, Balaji

AU - Sadhanala, Aditya

AU - Hurhangee, Michael

AU - Broch, Katharina

AU - Harkin, David J.

AU - Novák, Jiří

AU - Neophytou, Marios

AU - Hayoz, Pascal

AU - Sirringhaus, Henning

AU - McCulloch, Iain

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was carried out with financial support from BASF. Funding is gratefully acknowledged from Austrian Science Fund (FWF): T578-N19, EC FP7 Project SC2 (610115), EC FP7 Project ArtESun (604397), EPSRC EP/G037515/1, and EPSRC EP/M005143/1. The authors thank Dr. T. Arnold, Diamond Light Source, Didcot, UK and J. Rozbořil, Masaryk University, Brno, Czech Republic for assistance with the GIWAXS-measurements. Financial support from Diamond Light Source is gratefully acknowledged. K. B. gratefully acknowledges financial support from the German Research Foundation (BR 4869/1-1). J. N. acknowledges support from the project CEITEC 2020 (grant No. LQ1601 financed by the MEYS of the Czech Republic).

PY - 2016/8/18

Y1 - 2016/8/18

N2 - Wide-bandgap conjugated polymers with a linear naphthacenodithiophene (NDT) donor unit are herein reported along with their performance in both transistor and solar cell devices. The monomer is synthesized starting from 2,6-dihydroxynaphthalene with a double Fries rearrangement as the key step. By copolymerization with 2,1,3-benzothiadiazole (BT) via a palladium-catalyzed Suzuki coupling reaction, NDT-BT co-polymers with high molecular weights and narrow polydispersities are afforded. These novel wide-bandgap polymers are evaluated as the semiconducting polymer in both organic field effect transistor and organic photovoltaic applications. The synthesized polymers reveal an optical bandgap in the range of 1.8 eV with an electron affinity of 3.6 eV which provides sufficient energy offset for electron transfer to PC70BM acceptors. In organic field effect transistors, the synthesized polymers demonstrate high hole mobilities of around 0.4 cm2 V–1 s–1. By using a blend of NDT-BT with PC70BM as absorber layer in organic bulk heterojunction solar cells, power conversion efficiencies of 7.5% are obtained. This value is among the highest obtained for polymers with a wider bandgap (larger than 1.7 eV), making this polymer also interesting for application in tandem or multijunction solar cells. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

AB - Wide-bandgap conjugated polymers with a linear naphthacenodithiophene (NDT) donor unit are herein reported along with their performance in both transistor and solar cell devices. The monomer is synthesized starting from 2,6-dihydroxynaphthalene with a double Fries rearrangement as the key step. By copolymerization with 2,1,3-benzothiadiazole (BT) via a palladium-catalyzed Suzuki coupling reaction, NDT-BT co-polymers with high molecular weights and narrow polydispersities are afforded. These novel wide-bandgap polymers are evaluated as the semiconducting polymer in both organic field effect transistor and organic photovoltaic applications. The synthesized polymers reveal an optical bandgap in the range of 1.8 eV with an electron affinity of 3.6 eV which provides sufficient energy offset for electron transfer to PC70BM acceptors. In organic field effect transistors, the synthesized polymers demonstrate high hole mobilities of around 0.4 cm2 V–1 s–1. By using a blend of NDT-BT with PC70BM as absorber layer in organic bulk heterojunction solar cells, power conversion efficiencies of 7.5% are obtained. This value is among the highest obtained for polymers with a wider bandgap (larger than 1.7 eV), making this polymer also interesting for application in tandem or multijunction solar cells. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

UR - http://hdl.handle.net/10754/622111

UR - http://onlinelibrary.wiley.com/doi/10.1002/adfm.201602285/full

UR - http://www.scopus.com/inward/record.url?scp=84982214188&partnerID=8YFLogxK

U2 - 10.1002/adfm.201602285

DO - 10.1002/adfm.201602285

M3 - Article

SN - 1616-301X

VL - 26

SP - 6961

EP - 6969

JO - Advanced Functional Materials

JF - Advanced Functional Materials

IS - 38

ER -

Naphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiency

Abstract

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