Recent Advances of Chlorination in Organic Solar Cells

Herein, the impacts of the selective halogenation at two different positions of dicyanomethylene‐3‐indanone (IC) end groups and inner side chains of small molecular acceptors (SMAs) on the PD:SMA interfacial interactions, blend morphology, and resulting photovoltaic properties are described. In this study, four different SMAs (A1, A2, A3, and A4) with the same molecular backbone, but with different degrees of halogenation, are synthesized. The IC end groups on the backbones of the A1 and A3, and A2 and A4 SMAs are chlorinated and fluorinated, respectively; in addition, 6‐phenoxyhexyl inner side chains of the A3 and A4 are chlorinated. The SMAs are paired with a chlorinated PBDT‐Cl PD to construct organic solar cells (OSCs). The PBDT‐Cl:A4‐based OSC exhibits the highest power conversion efficiency of 17.2%, outperforming the PBDT‐Cl:A1‐(13.3%), PBDT‐Cl:A2‐(15.6%), and PBDT‐Cl:A3‐based OSC (16.5%). The Cl atoms on the side chains in the A3 and A4 SMAs enhance the molecular/energetic interactions at the PD:SMA interfaces and improve the blend morphology in terms of domain purity and spacing. These effects lead to the improved fill factors and reduced voltage loss of the PBDT‐Cl:A3‐ and PBDT‐Cl:A4‐based OSCs. This study demonstrates the importance of appropriate halogenation of SMAs in optimizing the blend morphology, reducing voltage loss, and improving OSC performance.

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Effect of the Selective Halogenation of Small Molecule Acceptors on the Blend Morphology and Voltage Loss of High‐Performance Solar Cells

Kim

Sun

Lee

et al. 2022

Adv Funct Materials

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Visible‐Light‐Mediated Nitrogen‐Centered Radical Strategy: Preparation of 3‐Acylated Spiro[4,5]trienones

et al. 2021

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A nitrogen‐centered radical strategy for the preparation of 3‐acylated spiro[4,5]trienones via visible‐light‐mediated acylation/ipso‐cyclization of alkynes with acyl oxime esters is reported. The alkyl‐ and aryl‐substituted acyl radicals, which generate from the cleavage of carbon‐carbon σ‐bonds in acyl oxime esters via nitrogen‐centered radical pathway, attack the carbon‐carbon triple bonds in propiolamides and then undergo ipso‐cyclization. This method provides a way for the construction of 3‐acyl‐substituted spiro[4,5]trienones, which can introduce aryl‐ or alkyl‐substituted acyl into spiro[4,5]trienone skeletons.

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Terminally Chlorinated and Thiophene‐linked Acceptor‐Donor‐Acceptor Structured 3D Acceptors with Versatile Processability for High‐efficiency Organic Solar Cells

Chen,

Kan,

Wang

et al. 2023

Angewandte Chemie

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To exploit the potential of our newly developed three‐dimensional (3D) dimerized acceptors, a series of chlorinated 3D acceptors (namely CH8‐3/4/5) were reported by precisely tuning the position of chlorine (Cl) atom. The introduction of Cl atom in central unit affects the molecular conformation. Whereas, by replacing fluorinated terminal groups (CH8‐3) with chlorinated terminal groups (CH8‐4 and CH8‐5), the red‐shift absorption and enhanced crystallization are achieved. Benefiting from these, all devices received promising power conversion efficiency (PCEs) over 16% as well as decent thermal/photo‐stabilities. Among them, PM6:CH8‐4 based device yielded a best PCE of 17.58%. Besides, the 3D merits with multi alkyl chains enable their versatile processability during the device preparation. Impressive PCEs of 17.27% and 16.23% could be achieved for non‐halogen solvent processable devices prepared in glovebox and ambient, respectively. 2.88 cm2 modules also obtained PCEs over 13% via spin‐coating and blade‐coating methods, respectively. These results are among the best performance of dimerized acceptors. The decent performance of CH8‐4 on small‐area devices, modules and non‐halogen solvent‐processed devices highlights the versatile processing capability of our 3D acceptors, as well as their potential applications in the future.

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Recent Advances of Chlorination in Organic Solar Cells

Cited by 10 publications

References 18 publications

Effect of the Selective Halogenation of Small Molecule Acceptors on the Blend Morphology and Voltage Loss of High‐Performance Solar Cells

Effect of the Selective Halogenation of Small Molecule Acceptors on the Blend Morphology and Voltage Loss of High‐Performance Solar Cells

Visible‐Light‐Mediated Nitrogen‐Centered Radical Strategy: Preparation of 3‐Acylated Spiro[4,5]trienones

Terminally Chlorinated and Thiophene‐linked Acceptor‐Donor‐Acceptor Structured 3D Acceptors with Versatile Processability for High‐efficiency Organic Solar Cells

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