Contorted Hexabenzocoronenes with Extended Heterocyclic Moieties Improve Visible-Light Absorption and Performance in Organic Solar Cells

Abstract

The large band gaps of existing contorted hexabenzocoronene derivatives severely limit visible-light absorption, restricting the photocurrents generated by solar cells utilizing contorted hexabenzocoronene (cHBC). To decrease the band gap and improve the light-harvesting properties, we synthesized cHBC derivatives having extended heterocyclic moieties as peripheral substituents. Tetrabenzofuranyldibenzocoronene (cTBFDBC) and tetrabenzothienodibenzocoronene (cTBTDBC) both exhibit broader absorption of the solar spectrum compared to cHBC, with peak absorbances on the order of 105 cm–1 in the near-ultraviolet and in the visible. Planar-heterojunction organic solar cells comprising cTBFDBC or cTBTDBC as the donor and C70 as the acceptor surpass those having cHBC in photocurrent generation and power-conversion efficiency. Interestingly, devices containing cTBFDBC/C70 exhibit the highest photocurrents despite cTBTDBC having the smallest band gap of the three cHBC derivatives. X-ray reflectivity of the active la...