A non-fullerene electron acceptor based on central carbazole and terminal diketopyrrolopyrrole functionalities for efficient, reproducible and solution-processable bulk-heterojunction devices

A novel, solution-processable non-fullerene electron acceptor, 6,6′-((9-(heptadecan-9-yl)-9H-carbazole-2,7-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) (coded as N7), based on central carbazole and terminal diketopyrrolopyrrole building blocks was designed, synthesized and characterized. N7 displayed excellent solubility, thanks to its design allowing incorporation of numerous lipophilic chains, thermal stability, and afforded a 2.30% power conversion efficiency with a high open-circuit voltage (1.17 V) when tested with the conventional donor polymer poly(3-hexylthiophene) in solution-processable bulk-heterojunction devices. To our knowledge, not only is N7 the first reported chromophore based on carbazole and diketopyrrolopyrrole functionalities but the open-circuit voltage reported here is among the highest values for a single junction bulk-heterojunction device that has been fabricated using a simple device architecture, with reproducible outcomes and with no special treatment.

Naphthalene diimide-based non-fullerene acceptors for simple, efficient, and solution-processable bulk-heterojunction devices

Two solution processable, non-fullerene electron acceptors, 2,2′-(((2,7-dioctyl-1,3,6,8-tetraoxo-1,2,3,6,7,8-exahydrobenzo[lmn][3,8]phenanthroline-4,9-diyl)bis(thiophene-5,2-diyl))bis(methanylylidene))dimalononitrile (R1) and (2Z,2′Z)-3,3′-((2,7-dioctyl-1,3,6,8-tetraoxo-1,2,3,6,7,8-hexahydrobenzo[lmn][3,8]phenanthroline-4,9-diyl)bis(thiophene-5,2-diyl))bis(2-(4-nitrophenyl) acrylonitrile) (R2), comprised of central naphthalene diimide and two different terminal accepting functionalities, malononitrile and 2-(4-nitrophenyl)acetonitrile, respectively, were designed and synthesised. The central and terminal accepting functionalities were connected via a mild conjugated thiophene linker. Both of the new materials (R1 and R2) displayed high thermal stability and were found to have energy levels matching those of the archetypal electron donor poly(3-hexylthiophene). A simple, solution-processable bulk-heterojunction device afforded a promising power conversion efficiency of 2.24% when R2 was used as a non-fullerene electron acceptor along with the conventional donor polymer poly(3-hexylthiophene). To the best of our knowledge, the materials reported herein are the first examples in the literature where synchronous use of such accepting blocks is demonstrated for the design and development of efficient non-fullerene electron acceptors.

A four-directional non-fullerene acceptor based on tetraphenylethylene and diketopyrrolopyrrole functionalities for efficient photovoltaic devices with a high open-circuit voltage of 1.18 V

Through the conjunction of tetraphenylethylene and diketopyrrolopyrrole functionalities, a novel four-directional non-fullerene electron acceptor (denoted as 4D) was designed, synthesized and characterized. The new chromophore is highly soluble (for instance >30 mg mL(-1) in o-dichlorobenzene), thermally stable, and exhibits energy levels matching those of the conventional and routinely used donor polymer poly(3-hexyl thiophene). A power conversion efficiency of 3.86% was obtained in solution-processable bulk-heterojunction devices with a very high open circuit voltage of 1.18 V.