Near-infrared Absorbing Non-fullerene Acceptors with Dithienopyrrole as π Spacer for Organic Solar Cells

doi:10.11944/j.issn.1000-0518.2019.09.190048

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (9): 1023-1034.DOI: 10.11944/j.issn.1000-0518.2019.09.190048

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Near-infrared Absorbing Non-fullerene Acceptors with Dithienopyrrole as π Spacer for Organic Solar Cells

ZHANG Xiaomei^a^b,LI Miaomiao^a^b^*(),WANG Qi^a^b,JIANG Yu^c,GENG Yanhou^a^b

^aSchool of Materials Science and Engineering and Tianjin Key Laboratory of Molecular Optoelectronic Science,Tianjin University,Tianjin 300072,China
^bCollaborative Innovation Center of Chemical Science and Engineering(Tianjin),Tianjin University,Tianjin 300072,China
^cState Key Laboratory of Polymer Physics and Chemistry,Changchun Institute of Applied Chemistry,Chinese Academy of Sciences,Changchun 130022,China

Received:2019-02-23 Accepted:2019-03-22 Published:2019-09-05 Online:2019-09-05
Contact: Miaomiao LI
Supported by:
Supported by the National Natural Science Foundation of China(No.51703158)

Abstract

Abstract:

A series of non-fullerene acceptors with dithieno[3,2-b:2',3'-d]pyrrole(DTP) π bridge to link indacenodithiophene(IDT) core and 3-(dicyanomethylidene)indan-1-one(IC) or difluorinated IC(2F-IC) terminals, i.e. IDTDTP-C₂C₂-H and IDTDTP-C₂C₂-F with 1-ethylpropyl on DTP, IDTDTP-C₆C₆-H and IDTDTP-C₆C₆-F with 1-hexylheptyl on DTP, and IDTDTP-C₁₂-H and IDTDTP-C₁₂-F with n-dodecyl on DTP, was designed and synthesized. These molecules achieved low optical band gaps(1.37~1.44 eV). Compared with the IC-terminated molecules(IDTDTP-C₂C₂-H, IDTDTP-C₆C₆-H and IDTDTP-C₁₂-H), IDTDTP-C₂C₂-F, IDTDTP-C₆C₆-F and IDTDTP-C₁₂-F with 2F-IC as terminals show red-shifted absorption spectra and down-shifted the highest occupied molecular orbitals(HOMO) and the lowest unoccupied molecular orbitals(LUMO) energy levels owing to the electron-withdrawing ability of F substituents. Organic solar cells(OSCs) based on these acceptors were fabricated with the wide-bandgap polymer poly[2,6-(4,8-bis(5-(2-ethylhexyl))thiophen-2-yl)-benzo[1,2-b:4,5-b']dithiophene-alt-5,5-(1',3'-di-2-thienyl)-5',7'-bis(2-ethylhexyl)-benzo[1',2'-c:4',5'-c']dithiophene-4,8-dione](PBDB-T) as the donor. Owing to the higher and more balanced hole and electron mobilities, and a proper phase-separated morphology in the blend film, IDTDTP-C₆C₆-F with 1-hexylheptyl on DTP unit achieved a maximum power conversion efficiency(PCE) of 6.94% with an open-circuit voltage(V_oc) of 0.86 V, a short circuit current density(J_sc) of 13.56 mA/cm² and a fill factor(FF) of 59.5%.

Key words: organic solar cell, non-fullerene acceptor, dithienopyrrole, alky side chain, power conversion efficiency

ZHANG Xiaomei, LI Miaomiao, WANG Qi, JIANG Yu, GENG Yanhou. Near-infrared Absorbing Non-fullerene Acceptors with Dithienopyrrole as π Spacer for Organic Solar Cells[J]. Chinese Journal of Applied Chemistry, 2019, 36(9): 1023-1034.

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Near-infrared Absorbing Non-fullerene Acceptors with Dithienopyrrole as π Spacer for Organic Solar Cells

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