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

Handle URI:
http://hdl.handle.net/10754/622111
Title:
Naphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiency
Authors:
Knall, Astrid Caroline; Ashraf, Raja Shahid; Nikolka, Mark; Nielsen, Christian B.; Purushothaman, Balaji; Sadhanala, Aditya; Hurhangee, Michael; Broch, Katharina; Harkin, David J.; Novák, Jiří; Neophytou, Marios; Hayoz, Pascal; Sirringhaus, Henning; McCulloch, Iain ( 0000-0002-6340-7217 )
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
KAUST Department:
Solar and Photovoltaic Engineering Research Center (SPERC)
Citation:
Knall A-C, Ashraf RS, Nikolka M, Nielsen CB, Purushothaman B, et al. (2016) Naphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiency. Advanced Functional Materials 26: 6961–6969. Available: http://dx.doi.org/10.1002/adfm.201602285.
Publisher:
Wiley-Blackwell
Journal:
Advanced Functional Materials
Issue Date:
18-Aug-2016
DOI:
10.1002/adfm.201602285
Type:
Article
ISSN:
1616-301X
Sponsors:
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).
Additional Links:
http://onlinelibrary.wiley.com/doi/10.1002/adfm.201602285/full
Appears in Collections:
Articles; Solar and Photovoltaic Engineering Research Center (SPERC)

Full metadata record

DC FieldValue Language
dc.contributor.authorKnall, Astrid Carolineen
dc.contributor.authorAshraf, Raja Shahiden
dc.contributor.authorNikolka, Marken
dc.contributor.authorNielsen, Christian B.en
dc.contributor.authorPurushothaman, Balajien
dc.contributor.authorSadhanala, Adityaen
dc.contributor.authorHurhangee, Michaelen
dc.contributor.authorBroch, Katharinaen
dc.contributor.authorHarkin, David J.en
dc.contributor.authorNovák, Jiříen
dc.contributor.authorNeophytou, Mariosen
dc.contributor.authorHayoz, Pascalen
dc.contributor.authorSirringhaus, Henningen
dc.contributor.authorMcCulloch, Iainen
dc.date.accessioned2017-01-01T13:18:23Z-
dc.date.available2017-01-01T13:18:23Z-
dc.date.issued2016-08-18en
dc.identifier.citationKnall A-C, Ashraf RS, Nikolka M, Nielsen CB, Purushothaman B, et al. (2016) Naphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiency. Advanced Functional Materials 26: 6961–6969. Available: http://dx.doi.org/10.1002/adfm.201602285.en
dc.identifier.issn1616-301Xen
dc.identifier.doi10.1002/adfm.201602285en
dc.identifier.urihttp://hdl.handle.net/10754/622111-
dc.description.abstractWide-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, Weinheimen
dc.description.sponsorshipThis 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).en
dc.publisherWiley-Blackwellen
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/adfm.201602285/fullen
dc.subjectconjugated polymersen
dc.subjectorganic field-effect transistorsen
dc.subjectorganic semiconductorsen
dc.subjectorganic solar cellsen
dc.titleNaphthacenodithiophene Based Polymers-New Members of the Acenodithiophene Family Exhibiting High Mobility and Power Conversion Efficiencyen
dc.typeArticleen
dc.contributor.departmentSolar and Photovoltaic Engineering Research Center (SPERC)en
dc.identifier.journalAdvanced Functional Materialsen
dc.contributor.institutionDepartment of Chemistry and Centre for Plastic Electronics; Imperial College London; London SW7 2AZ UKen
dc.contributor.institutionInstitute for Chemistry and Technology of Materials (ICTM); NAWI Graz; Graz University of Technology; Stremayrgasse 9 8010 Graz Austriaen
dc.contributor.institutionCavendish Laboratory; University of Cambridge; Cambridge CB3 OHE UKen
dc.contributor.institutionMaterials Research Institute and School of Biological and Chemical Sciences; Queen Mary University of London; Mile End Road London E1 4NS UKen
dc.contributor.institutionCEITEC MU; Masaryk University and Department of Condensed Matter Physics; Masaryk University; Kotlářská 2 61137 Brno Czech Republicen
dc.contributor.institutionBASF Schweiz AG; GMV/BE, R-1059.5.09; Mattenstrasse 4058 Basel Switzerlanden
kaust.authorNeophytou, Mariosen
kaust.authorMcCulloch, Iainen
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