Fluorinated Isoindigo Based Donor-Acceptor Small Molecule and Polymers for High-Performance Solution-Processed Organic Photovoltaic Devices

Christophe Detrembleur^a, Christine Jérôme^a, Mirco Tomassetti^a, Farid OUHIB^a, Jean Manca^b

^aCERM, University of Liège, university of liege Sart-tilaman, Liège, 4000, Belgium

^bIMOMEC, University of Hasselt, University of Hasselt depenbeek, Belgium

Proceedings of International Conference on New Advances in Materials Research for Solar Fuels Production (SolarFuel14)

Montréal, Canada, 2014 June 25th - 26th

Organizer: Thomas Hamann

Poster, Farid OUHIB, 030
Publication date: 16th April 2014

Organic photovoltaic (OPVs) cells are viewed as one of the most promising candidates for low cost solar cells because of the possibility of a simple and cheap production on flexible and large area substrates.¹ The power conversion efficiency (PCE) of polymer solar cells has improved rapidly from below 1% to over 9% in the past 16 years.² The main contribution to this progress was made by the molecular engineering of new conjugated polymers and small molecules (as the donor materials), assisted by limited successes in derivatizing the fullerenes (PC60BM or PC70BM as the electron acceptor). The most critical challenges in developing ideal donor materials are to design and synthesize conjugated polymers with (1) appropriate solubility and miscibility to achieve an optimal blend with PCBM in the active layer, (2) strong absorption ability and narrow optical band gap to harvest more solar photon for a thin active layer, (3) well matched HOMO – LUMO energy levels between polymer and PCBM to ensure a good charge separation and high open circuit voltage (Voc) and (4) high hole mobility.³ Amongst all the strategies used to tentatively reach these desired properties, the combination of the electron-rich (donor) and electron-deficient (acceptor) groups as repeating units, forming internal donor-acceptor (D-A) structures, have been widely used for developing low band gap semi-conducting materials.⁴ it is still a challenge to develop an ideal low-band-gap copolymer by a judicious choice of the donor-acceptor combination.
Different D-A small molecules and copolymers with fluorinated isoindigo as the strong acceptor and oligothiophene as the donor have been designed and synthesized for solution-processed bulk-heterojunction solar cells. Interesting PCEs were achieved by improving the short-circuit current density without sacrificing the high open-circuit voltage and fill factor through the strategy of fluorinated isoindigo incorporating in D-A small molecules and polymers for OPVs.
References
[1] Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science. 1995,270, 1789-1791.[2](a) Zhou et al. Angew. Chem., Int. Ed. 2011, 50, 2995. (b) Son et al. J. Am. Chem. Soc. 2011, 133, 1885.(c) Chen et al. Nature Photonics, 2009, 3, 649.6. [3] Sun, Y.; Welch, G. C.; Leong, W. L.; Takacs, C. J.; Bazan, G. C.; Heeger, A. J. Nat. Mater. 2012, 11, 44.[4] Heeger, A. J. Chem. Soc. Rev. 2010, 39, 2354−2371.

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