Citation: 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. doi: 10.11944/j.issn.1000-0518.2019.09.190048 shu

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

a.
School of Materials Science and Engineering and Tianjin Key Laboratory of Molecular Optoelectronic Science, Tianjin University, Tianjin 300072, China
b.
Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin University, Tianjin 300072, China
c.
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China

Corresponding author: LI Miaomiao, miaomiao.li@tju.edu.cn
Received Date: 23 February 2019
Revised Date: 18 March 2019
Accepted Date: 22 March 2019

Fund Project: the National Natural Science Foundation of China 51703158Supported by the National Natural Science Foundation of China(No.51703158)

Figures(5)

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%.
- organic solar cell,
- non-fullerene acceptor,
- dithienopyrrole,
- alky side chain,
- power conversion efficiency
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