Benzoporphyrin–Diketopyrrolopyrrole Conjugates based Organic Solar Cells

Daiki Kuzuhara1,  Kohtaro Takahashi1,  Naoya Yamada2,  Yuji Yamaguchi2,  Naoki Aratani2,  Ken-ichi Nakayama1,  Hiroko Yamada1
1Nara Institute of Science and Technology, 2Yamagata University


Abstract

Thin-film organic solar cells (OSCs) have great attractive attention as key technology for next energy harvesting source. Recently, power-conversion efficiencies (PCEs) are reached closely 10% with both of small molecule and polymer materials. However, PCE of OSC is limited compared with the inorganic materials-based solar cells. Therefore, OSC requires new organic functional dyes for the improvement of PCE. Benzoporphyrin (BP) is reported as one of the promising organic semiconducting materials. However, solubility of BP in common organic solvents is terribly low. It is difficult to use intact BPs for the device fabrication by solution process. Ono and colleagues have developed the thermal-convertible precursors of BP, namely bicyclo[2,2,2]octadiene-fused porphyrin (CP). CP is soluble in organic solvents and can be converted to BP under heating conditions by retro-Diels-Alder reaction. This thermal conversion method allowed us to fabricate BP-based OSC by solution process: spin-coating of CP solution followed by heating of CP as-spun film. However, there are still problems and limitations of the BP for the application in OSC because BP has weak absorption in the NIR regions and the HOMO level of BP is higher than that of the ideal donor materials for OSC. It is known that the wide-range absorption in the visible to NIR regions and the appropriate HOMO and LUMO levels are necessary for the improvement of the PCE. In this presentation, we will report the design, synthesis and properties of the benzoporphyrin-diketopyrrlopyrrole conjugates (BP–DPPs) for the p-type materials for the OSCs. The BP–DPPs were obtained from corresponding precursor of CP–DPPs by retro Diels-Alder reaction. The absorption spectra of BP–DPPs were measured as thin film on glass substrate. The BP–DPPs have a character of panchromatic dye which absorption covers between visible to NIR regions with four peak tops. We have fabricated the bulk heterojunction (BHJ) type OSC with BP–DPPs as p-type materials and PC61BM as an n-type material. The highest PCE of 4.0% for BP–DPP:PC61BM was achieved with short-circuit current (JSC) of 12.47 mA cm-2, open circuit voltage (Voc) of 0.68 V, and fill factor (FF) of 0.47. We will also report the evaluations of film structures of these devices by AFM and XRD measurements.