Halogenated 9H-Indeno[1,2-b]Pyrazine-2,3-Dicarbonitrile End Groups Based Asymmetric Non-Fullerene Acceptors for Green Solvent-Processable, Additive-Free, and Stable Organic Solar Cells,Small

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Halogenated 9H-Indeno[1,2-b]Pyrazine-2,3-Dicarbonitrile End Groups Based Asymmetric Non-Fullerene Acceptors for Green Solvent-Processable, Additive-Free, and Stable Organic Solar Cells
Small ( IF 13.0 ) Pub Date : 2024-04-02 , DOI: 10.1002/smll.202401080
Peddaboodi Gopikrishna ₁ , Huijeong Choi ₁ , Do Hui Kim ₂ , Dongchan Lee ₂ , Jun Ho Hwang ₃ , Seon-Mi Jin ₃ , Eunji Lee ₃ , Shinuk Cho ₂ , BongSoo Kim _{1,

4,

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Affiliation

Non-fullerene acceptors (NFAs) significantly enhance photovoltaic performance in organic solar cells (OSCs) using halogenated solvents and additives. However, these solvents are environmentally detrimental and unsuitable for industrial-scale production, and the issue of OSCs’ poor long-term stability persists. This report introduces eight asymmetric NFAs (IPCnF-BBO-IC2F, IPCnF-BBO-IC2Cl, IPCnCl-BBO-IC2F, and IPCnCl-BBO-IC2Cl, where n = 1 and 2). These NFAs comprise a 12,13-bis(2-butyloctyl)-3,9-diundecyl-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-g]thieno[2',3':4,5]thieno-[3,2-b]indole (BBO) core. One end of the core attaches to a mono- or di-halogenated 9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile (IPC) end group (IPC1F, IPC1Cl, IPC2F, or IPC2Cl), while the other end connects to a 2-(5,6-dihalo-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (IC) end group (IC2F or IC2Cl). The optical and electronic properties of these NFAs can be finely tuned by controlling the number of halogen atoms. Crucially, these NFAs demonstrate excellent compatibility with PM6 even in o-xylene, facilitating the production of additive-free OSCs. The di-halogenated IPC-based NFAs outperform their mono-halogenated counterparts in photovoltaic performance within OSCs. Remarkably, the di-halogenated IPC-based NFAs maintain 94‒98% of their initial PCEs over 2000 h in air without encapsulation, indicating superior long-term device stability. These findings imply that the integration of di-halogenated IPCs in asymmetric NFA design offers a promising route to efficient, stable OSCs manufactured through environmentally friendly processes.

中文翻译：

用于绿色溶剂加工、无添加剂且稳定的有机太阳能电池的基于卤化9H-茚并[1,2-b]吡嗪-2,3-二甲腈端基的不对称非富勒烯受体

非富勒烯受体 (NFA) 使用卤化溶剂和添加剂可显着增强有机太阳能电池 (OSC) 的光伏性能。然而，这些溶剂对环境有害且不适合工业规模生产，并且OSC的长期稳定性差的问题仍然存在。本报告介绍了八种不对称 NFA（IPC n F-BBO-IC2F、IPC n F-BBO-IC2Cl、IPC n Cl-BBO-IC2F 和 IPC n Cl-BBO-IC2Cl，其中n = 1 和 2）。这些 NFA 包含 12,13-双(2-丁基辛基)-3,9-二十一烷基-12,13-二氢-[1,2,5]噻二唑并[3,4 -e ]噻吩并[2'',3' ':4',5']噻吩并[2',3':4,5]吡咯并[3,2- g ]噻吩并[2',3':4,5]噻吩并-[3,2- b ]吲哚（BBO）核心。核心的一端连接到单卤代或二卤代 9 H -茚并[1,2- b ]吡嗪-2,3-二甲腈 (IPC) 端基（IPC1F、IPC1Cl、IPC2F 或 IPC2Cl），而另一端连接至 2-(5,6-二卤-3-氧代-2,3-二氢-1 H-茚-1-亚基)丙二腈 (IC) 端基（IC2F 或 IC2Cl）。这些 NFA 的光学和电子特性可以通过控制卤素原子的数量来微调。至关重要的是，这些 NFA 即使在邻二甲苯中也表现出与 PM6 的出色相容性，从而促进了无添加剂 OSC 的生产。基于二卤化 IPC 的 NFA 在 OSC 内的光伏性能方面优于单卤化同类产品。值得注意的是，基于二卤代 IPC 的 NFA 在没有封装的情况下在空气中 2000 小时内保持了 94-98% 的初始 PCE，这表明器件具有出色的长期稳定性。这些发现表明，将二卤代 IPC 集成到不对称 NFA 设计中，为通过环保工艺制造高效、稳定的 OSC 提供了一条有前途的途径。

更新日期：2024-04-02

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