Oligomeric Acceptor: A “Two‐in‐One” Strategy to Bridge Small Molecules and Polymers for Stable Solar Devices

Wang, Hengtao; Cao, Congcong; Chen, Hui; Lai, Hanjian; Ke, Chunxian; Zhu, Yulin; Li, Heng; He, Feng

doi:10.1002/anie.202201844

Cited by 120 publications

(36 citation statements)

References 51 publications

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“…Dimerized small-molecule acceptors (DSMAs) are promising alternatives because they can leverage the advantages of both SMA and PSMA systems. , DSMAs can demonstrate higher electron mobility than PSMAs because their discrete molecular structures enable more-strongly developed crystalline structures and intermolecular assembly as well as low batch-to-batch variation. In addition, because DSMAs have a larger molecular size than their constituent SMAs, they have a significantly higher onset temperature (i.e., T g ) for molecular movement and slower diffusion kinetics, which can lead to OSCs with enhanced thermal and morphological stability. , However, the PCEs of DSMA-based OSCs are still lower than those of state-of-the-art SMA- and PSMA-based OSCs, thereby necessitating the further development of DSMAs. In particular, it is important to develop efficient DSMAs so that their electron mobilities are comparable to those of SMAs (>10 –3 to 10 –4 cm 2 V –1 s –1 ).…”

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“…47,48 Dimerized small-molecule acceptors (DSMAs) are promising alternatives because they can leverage the advantages of both SMA and PSMA systems. 49,50 DSMAs can demonstrate higher electron mobility than PSMAs because their discrete molecular structures enable more-strongly developed crystalline structures and intermolecular assembly as well as low batch-to-batch variation. In addition, because DSMAs have a larger molecular size than their constituent SMAs, they have a significantly higher onset temperature (i.e., T g ) for molecular movement and slower diffusion kinetics, which can lead to OSCs with enhanced thermal and morphological stability.…”

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Linker Engineering of Dimerized Small Molecule Acceptors for Highly Efficient and Stable Organic Solar Cells

et al. 2023

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High power conversion efficiency (PCE) and long-term stability are important requirements for commercialization of organic solar cells (OSCs). In this study, we demonstrate efficient (PCE = 18.60%) and stable (t 80% lifetime > 4000 h) OSCs by developing a series of dimerized smallmolecule acceptors (DSMAs). We prepared three different DSMAs (DYT, DYV, and DYTVT) by using different linkers (i.e., thiophene, vinylene, and thiophene− vinylene− thiophene), to connect their two Y-based building blocks. We find that the crystalline properties and glass transition temperature (T g ) of DSMAs can be systematically modulated by the linker selection. A DYV-based OSC achieves the highest PCE (18.60%) among the DSMA-based OSCs owing to the appropriate backbone rigidity of DYV, leading to an optimal blend morphology and high electron mobility. Importantly, the DYVbased OSC also demonstrates excellent operational stability under 1-sun illumination, i.e., a t 80% lifetime of 4005 h.

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confidence: 99%

Linker Engineering of Dimerized Small Molecule Acceptors for Highly Efficient and Stable Organic Solar Cells

et al. 2023

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“…Recently, with increased attention on device stability, multiple strategies via device engineering, e.g., developing stable holetransporting interfacial layer, 53 or photovoltaic materials design, e.g., designing oligomeric acceptors 54 are also reported and found effective in extending the T 80 value.…”

Section: Photostability Of Devicementioning

confidence: 99%

Design of Non-fused Ring Acceptors toward High-Performance, Stable, and Low-Cost Organic Photovoltaics

Shen

et al. 2022

Acc. Mater. Res.

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Conspectus Toward future commercial applications of organic solar cells (OSCs), organic photovoltaic materials that enable high efficiency, excellent stability, and low cost should be developed. Fused-ring electron acceptors (FREAs) have declared that OSCs are capable of showing efficiencies over 19%, whereas stability and cost are not solved yet. As the counterparts of FREAs, non-fused ring electron acceptors (NFREAs) are more flexible in molecular design. They have better stability because of the reduction of intramolecular tension via breaking fused backbone and have more advantages in cost with the reduction of synthetic complexity. However, the challenge for NFREAs is the relatively lower efficiencies (around 15% at current stage), which require better molecular designs for addressing the issues of conformational unicity and effective molecular packing. In this Account, we comprehensively summarize works about NFREAs carried out in our group from three main frameworks, including molecular design and efficiency optimization, material cost, and stability. First, in the part of molecular design and efficiency optimization, the existing rotatable single bond in NFREAs will bring the problem of conformational uncertainty, but it can be solved through proper molecular design, which also regulates the energy levels, light absorption range, and the packing mode of the molecule for obtaining higher performance. Thus, in this part, we discuss the evolution of NFREAs in three aspects, including molecular skeleton optimization, terminal modification, and side chain engineering. Many strategies are used in the design of a molecular skeleton, such as utilizing the quinoid effect, introducing functional groups with the electron push–pulling effect, and using multiple conformational lock. Furthermore, simplifying the skeleton is also the preferred development tendency. As for the terminal, the main modification strategy is adjusting the conjugation length and halogen atoms. What is more, by adjusting the side chain to induce appropriate steric hindrance, we can fix the orientation of molecules, thus regulating molecular packing modes. Second, regarding material cost, we compare the synthesis complexities between state-of-the-art FREAs and NFREAs. Because the synthesis processes of NFREAs reduce the complex cyclization reactions, the synthesis routes are greatly simplified, and the molecule can be obtained through three minimal steps. Third, regarding stability, we analyze the workable strategies used in NFREAs from the views of intrinsic material stability, photostability, and thermal stability. Finally, we conclude the challenges that should be conquered for NFREAs and propose perspectives that could be performed for NFREAs, with the hope of pushing the development of OSCs toward high performance, stability, and low cost.

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“…Organic solar cells (OSCs) have made continuous progress in recent years due to the breakthrough in organic semiconducting materials [1][2][3][4][5][6][7][8][9][10][11] . Especially, the emerging A-DAD-A type small molecule acceptors (SMAs), Y6 and its analogs [2,12] , promote the efficiency of OSCs to 15%-20% through the modification of the fused DAD backbone, electron-withdrawing end groups and side chains [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] . Meanwhile, some A-DAD-A acceptors with ultra-narrow bandgap (ultra-NBG) have been reported to realize highJ SC for high-performance tandem or semi-transparent OSCs [31][32][33][34][35][36] .…”

Section: Background and Originality Contentmentioning

confidence: 99%

Synergetic alkoxy side-chain and chlorine-contained end group strategy toward high performance ultra-narrow bandgap small molecule acceptors

Zou

Wei

Liang

et al. 2023

Preprint

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Ultra-narrow bandgap (ultra-NBG) small molecule acceptors (SMAs) show great potential in organic solar cells (OSCs) due to the extend-ed near-infrared (NIR) absorption. In this work, a synergetic alkoxy side-chain and chlorine-contained end group strategy is employed to achieve A-DA’D-A type ultra-NBG SMAs by introducing alkoxy chains with oxygen atom at the second position into the thiophene β posi-tion as well as replacing the F atoms with Cl atoms in the end group. As a result, the heptacyclic BZO-4F shows a redshifted absorption onset (960 nm) than Y11 (932 nm) without oxygen atoms in the side chains. Then, the fluorinated end groups are substituted with the chlorinated ones to synthesize BZO-4Cl. The absorption onset of BZO-4Cl is further redshifted to 990 nm, corresponding to an optical ultra-NBG of 1.25 eV. When blending with the polymer donor PBDB-T, the binary devices based on PBDB-T: BZO-4F and PBDB-T: BZO-4Cl delivers power conversion efficiencies (PCEs) over 12%. Furthermore, ternary devices with the addition of BZ4F-O-1 into PBDB-T: BZO-4Cl system achieve the optimal PCE of 15.51%. This work proposes a synergetic alkoxy side-chain and chlorine-contained end group strategy to achieve A-DA’D-A type ultra-NBG SMAs, which is important for future molecular design.

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Oligomeric Acceptor: A “Two‐in‐One” Strategy to Bridge Small Molecules and Polymers for Stable Solar Devices

Cited by 120 publications

References 51 publications

Linker Engineering of Dimerized Small Molecule Acceptors for Highly Efficient and Stable Organic Solar Cells

Linker Engineering of Dimerized Small Molecule Acceptors for Highly Efficient and Stable Organic Solar Cells

Design of Non-fused Ring Acceptors toward High-Performance, Stable, and Low-Cost Organic Photovoltaics

Synergetic alkoxy side-chain and chlorine-contained end group strategy toward high performance ultra-narrow bandgap small molecule acceptors

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