N-Annulated Perylene Bisimide-Based Double-Cable Polymers with Open-Circuit Voltage Approaching 1.20 V in Single-Component Organic Solar Cells

Abstract

In this work, we have introduced single/double-sided N-annulated perylene bisimide (PBI) with deep energy levels into double-cable polymers with poly­[1-(5-(4,8-bis­(4-chloro-5-(2-ethylhexyl)­thiophen-2-yl)-6-methylbenzo­[1,2-b:4,5-b′]­dithiophen-2-yl)­thiophen-2-yl)-5,7-bis­(2-ethylhexyl)-3-(5-methylthiophen-2-yl)-4H,8H-benzo­[1,2-c:4,5-c′]­dithiophene-4,8-dione] (PBDB-T-Cl) as a donor backbone, marking as s-PPNR and as-PPNR, according to the molecular symmetry. Both double-cable polymers displayed a high open-circuit voltage approaching 1.20 V in light of high energy level discrepancy between electron-donating and electron-withdrawing parts, which is the highest open-circuit voltage among double-cable-based single-component organic solar cell (SCOSC) devices. Additionally, the asymmetric polymer displayed improved absorption spectra, thereby promoting crystallization and phase separation. Consequently, the as-PPNR-based SCOSCs achieved a power conversion efficiency of 5.05% along with a higher short-circuit current density and fill factor than their s-PPNR-based counterparts. In this work, we have successfully incorporated N-annulated PBI into double-cable polymers and revealed the important effects on structural symmetry and phase separation of double-cable polymers for higher SCOSC performance.

Development of n-Type Small-Molecule Acceptors for Low Dark Current Density and Fast Response Organic Photodetectors

“…(4,4,9,9-Tetrakis­(4-hexylphenyl)-4,9-dihydro- s -indaceno­[1,2- b :5,6- b ′]­dithiophene-2,7-diyl)­bis­(trimethylstannane) was provided by SunaTech. (4,4-bis­(2-Ethylhexyl)-4 H -cyclopenta­[2,1- b :3,4- b ′]­dithiophene-2,6-diyl)­bis­(trimethylstannane) and compounds 1–5 were synthesized according to previously reported methods. , Purchased reagents were used without further purification.…”

“…(4,4-bis(2-Ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6-diyl)bis-(trimethylstannane) and compounds 1−5 were synthesized according to previously reported methods. 56,57 [8,1,2ghi]isoindole-1,3,7,9(2H,5H,8H)-tetraone) (C-NPDI). N-PDI-Br (620 mg, 0.76 mmol), (4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6-diyl)bis(trimethylstannane) (182.08 mg, 0.25 mmol), and tetrakis(triphenylphosphine)palladium(0) (28.9 mg, 0.025 mmol) were dissolved in toluene (30 mL).…”

The Application of Y Series Acceptor-Based Double-Cable Polymers in Single-Material Organic Solar Cells

“…The introduction of noncovalent hydrogen bonds and dipole–dipole interactions to enhance intra/intermolecular interactions is beneficial for BHJ morphology stability. , Additionally, the partial formation of chemical bonds between molecules through optical and chemical cross-linking has been proven to limit morphology evolution to a certain extent in conventional BHJ active layers. , A more fundamental solution to improve morphology stability, and thereby enhance the photo, thermal, and mechanical stabilities of the device, is to chemically bond the donor and acceptor materials to synthesize a single-component material. , This is because, compared to the intermolecular heterojunction structures formed in two-phase or even multiphase blends, active layers consisting of single-component materials naturally form an intramolecular heterojunction structure due to the inclusion of donor and acceptor fragments within the same molecule, which significantly reduces the dependence of the charge transfer behavior on the active layer’s morphology. − Moreover, as the active layer consists of only one single-component material, the morphology evolution caused by the migration rate difference of various materials in the multiphase system under external driving force can be effectively avoided, thereby improving the stability of single-component OPVs (SCOPVs). , Recently, numerous single-component materials, mainly including molecular dyads, ,, double-cable conjugated polymers (DCCPs), − and conjugated block copolymers (CBCs), ,,− have been designed and synthesized to meet commercial application demands. For instance, Ma and Min et al successfully incorporated efficient donor (PBDB-T) and acceptor (Y series acceptor) segments into single-component materials through block copolymerization, achieving promising power conversion efficiencies (PCEs) of over 11%. ,, Subsequent optimizations of polymerization conditions and molecular structures led to the efficiency of CBCs-based SCOPVs surpassing 15%, further highlighting their application potential. , However, one major drawback of CBC materials synthesized by a one-pot polymerization method is their poor batch reproducibility, which hampers commercial production. , …”

Hybrid Nonfused Electron Acceptors with Perylene Diimide Pendants for Organic Solar Cells

“…Thieno­[3,4- c ]­pyrrole-4,6-dione (TPD)-based NFEAs have shown potential for achieving high-performance OSCs due to their suitable energy levels, simple synthesis, near-infrared absorption, and easy morphology control. ,− Besides, the PBI unit, which has been a commercial product for nearly 100 years, possesses several advantages, including demonstrated stability, simple synthesis, high crystallinity, and high electron mobility in OSCs. ,− Here, we want to integrate the TPD-based NFEAs and the PBI unit into one molecular unit to reveal the fascinating photophysical properties of the hybrid acceptor. In this work, we have designed and synthesized two hybrid acceptors (TPDICPBI and TPDICPBI-C6), which combine the TPD-based NFEAs and the PBI unit through different linkers, as shown in Figure , and investigated their optical, electrochemical, and thermodynamic properties.…”