RESUMO
In this report, an atom efficient and facile synthetic strategy for accessing multi-diketopyrrolopyrrole (DPP)-based oligomers used in solution-processed organic field effect transistors (OFETs) and organic solar cells (OSCs) has been developed. The DPP units were successfully installed onto benzene and pyrene cores via palladium-catalyzed dehydrohalogenative coupling of mono-capped DPPs with multi-bromo-benzene or -pyrene (direct arylation), affording four oligomer small molecules (SMs 1-4) containing bis-, tri-, tri-, and tetra-DPP, respectively, in high yields of 78-96%. All the designed linear or branched DPP-based oligomers exhibit broad light absorptions, narrow band-gaps (1.60-1.73 eV), deep highest occupied molecular orbital (HOMO) levels (-5.26â¼-5.18 eV), and good thermal stability (Td=390-401 °C). OFETs based on SMs 1-4 showed hole mobilities of 0.0033, 0.0056, 0.0005, and 0.0026 cm2 V(-1) s(-1), respectively. OSCs based on SMs 1-4 under one sun achieved power conversion efficiencies of 3.00%, 3.71%, 2.47%, and 1.86% accordingly, along with high open-circuit voltages of 0.86-0.94 V. For OSC devices of SM 1, SM 3, and SM 4, the solvent CHCl3 was solely employed to the formation of active layers; neither high boiling point additives nor annealing post-treatment was needed. Such a simple process benefits the large-scale production of OSCs via roll to roll technology.
RESUMO
A diketo-pyrrolo-pyrrole (DPP) oligomer containing three DPP cores (Ph4Th4(DPP)3) was synthesized via direct arylation of C-H bonds (DACH). Ph4Th4(DPP)3 has good solubility in many organic solvents, and shows a broad absorption band from the visible to near-infrared region as well as a field-effect hole mobility as high as 0.006 cm(2) V(-1) s(-1). Solution-processed bulk heterojunction organic solar cells based on blends of Ph4Th4(DPP)3 as electron donor and fullerene derivative as electron acceptor were fabricated. An optimized power conversion efficiency of 3.76% with a high open-circuit voltage of 0.85 V was achieved after finely tuning the morphology by changing the blend ratio and by adding additives. These results indicate that DACH is an effective way to produce π-conjugated oligomers for organic solar cells.
