Stable dinitrile end-capped closed-shell non-quinodimethane as donor, acceptor and additive of organic solar cells

Non-fullerene acceptors exhibit great potential to improve photovoltaic performances of organic solar cells. However, it is important to further enhance chemical stability and device durability for future commercialization, especially for Y6-series small molecule acceptors with 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (IC) type as ending group. In this work, an IC-free photovoltaic material YF-CN consisting of 2-fluoren-9-ylidenepropanedinitrile terminal was designed and synthesized by stille coupling. YF-CN exhibited closed-shell chemical structure with enhanced photostability and improved morphological compatibility with the binary PCE10:Y6 blend. The moderate energy level makes YF-CN could serve as a multifunctional material, such as donor, acceptor and the third component. When adding YF-CN as second donor into PCE10:Y6 system, an improved power conversion efficiency of 12.03% was achieved for as-cast device. Importantly, the ternary PCE10:YF-CN:Y6-devices showed enhanced storage durability maintaining 91% of initial PCE after the 360 hours. This work provides new perspective to understand the open-shell character of donor and closed-shell structure of acceptors, respectively, as well as promising design concept of stable IC-free acceptors for organic solar cells.

Stable dinitrile end-capped closed-shell non-quinodimethane as donor, acceptor and additive of organic solar cells

Non-fullerene acceptors exhibit great potential to improve photovoltaic performances of organic solar cells. However, it is important to further enhance chemical stability and device durability for future commercialization, especially for Y6-series small molecule acceptors with 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (IC) type as ending group. In this work, an IC-free photovoltaic material YF-CN consisting of 2-fluoren-9-ylidenepropanedinitrile terminal was designed and synthesized by stille coupling. YF-CN exhibits enhanced photostability and improves morphological compatibility with the binary PCE10:Y6 blend. The moderate energy level makes YF-CN could serve as a multifunctional material, such as donor, acceptor and the third component. When adding YF-CN as second donor into PCE10:Y6 system, an improved power conversion efficiency of 12.03% was achieved for as-cast device. Importantly, the ternary PCE10:YF-CN:Y6-devices showed enhanced storage durability maintaining 91% of initial PCE after the 360 hours. This work provides new perspective to understand the open-shell and closed-shell structure of donors and acceptors, as well as promising design concept of stable IC-free acceptors for organic solar cells.

Organosulfur Materials with High Photo- and Photo-Oxidation Stability: 10-Anthryl Sulfoxides and Sulfones and Their Photophysical Properties Dependent on the Sulfur Oxidation State

While few studies show only symmetrical and poorly mono-SOn (n = 0–2) substituted acenes, in this study, we present a synthesis of a new group of unsymmetrical, significantly substituted derivatives, which revealed unique photophysical properties. Both sulfides (S), sulfoxides (SO) and sulfones (SO2) showed very high photochemical stabilities, unusual for these groups, during UV-irradiation at 254/365 nm (air O2 and Ar), which was higher than any found in the literature. For the (S)/(SO) series (254 nm), the stabilities of 80–519 min. (air O2 and Ar) were found. At 365 nm, stabilities of 124—812 min./(air O2) for (S)/(SO) and higher for (SO2) were observed. Photoluminescence lifetimes of (SOn) of the lower anthryl symmetry remained in the following order: (SO2) < (S) < (SO); those with full symmetry were in the following order: (S) < (SO) < (SO2). The enhanced photostability was explained with DFT/MS/Hammett’s constants, which showed the leading role of the SOn groups in stabilization of HOMO/LUMO frontier orbitals. The SOn (n = 0–2) substituted acenes turned out to be tunable violet/blue/green emitters by oxidation of S atoms and the introduction of rich substitution.