The first connection of carbonyl-bridged triarylamine and diketopyrrolopyrrole functionalities to generate a three-dimensional, non-fullerene electron acceptor

• Published in: Materials chemistry frontiers 2020-07, Vol.4 (7), p.2176-2183
• Main Authors: Jadhav, Ratan W, Hangarge, Rahul V, Aljabri, Mahmood D, More, Kerba Shivaji, Chen, Jing-Yu, Jones, Lathe A, Evans, Richard A, Li, Jing-Liang, Bhosale, Sheshanath V, Gupta, Akhil
• Format: Article
• Language: English
• Subjects: Carbonyls; Chemical reactions; Cross coupling; Electrons; Energy conversion efficiency; Fluorescence; Fullerenes; Heterojunction devices; Photovoltaic cells; Substrates
• ISSN: 2052-1537; 2052-1537
• DOI: 10.1039/d0qm00041h

We report for the first time the use of a carbonyl-bridged triarylamine core with diketopyrrolopyrrole terminal units to generate a three-dimensional, non-planar non-fullerene electron acceptor with favourable properties for use in organic photovoltaic devices. The carbonyl-bridged triarylamine-functionalized, small molecule non-fullerene electron acceptor, 2,6,10-tris(5-(2,5-bis(2-ethylhexyl)-3,6-dioxo-4-(thiophen-2-yl)-2,3,5,6-tetrahydropyrrolo[3,4- c ]pyrrol-1-yl)thiophen-2-yl)-4 H -benzo[9,1]quinolizino[3,4,5,6,7- defg ]acridine-4,8,12-trione (coded as R1 ), was synthesized via the industrially viable, Suzuki cross-coupling reaction using commercially and cheaply available substrates. Using PTB7 as a donor, a power conversion efficiency of 9.33% was achieved in simple, solution-processable bulk-heterojunction devices, a result that is amongst the best in the literature for three-dimensional non-fullerene acceptors. Carbonyl-bridged triarylamine-based, three-dimensional non-fullerene acceptor ( R1 ); device: ITO/PEDOT:PSS/PTB7: R1 (1: 1.2)/Ca/Al; PCE = 9.33%