Chlorinated Spiroconjugated Fused Extended Aromatics for Multifunctional Organic Electronics

Dong Meng; Rui Wang; Janice B Lin; Jonathan Lee Yang; Selbi Nuryyeva; Yu-Che Lin; Shuai Yuan; Zhao-Kui Wang; Elizabeth Zhang; Chengyi Xiao; Danlei Zhu; Lang Jiang; Yepin Zhao; Zhenxing Li; Chenhui Zhu; Kendall N Houk; Yang Yang

doi:10.1002/adma.202006120

Chlorinated Spiroconjugated Fused Extended Aromatics for Multifunctional Organic Electronics

Adv Mater. 2021 Mar;33(12):e2006120. doi: 10.1002/adma.202006120. Epub 2021 Feb 15.

Authors

Dong Meng¹, Rui Wang¹, Janice B Lin², Jonathan Lee Yang³, Selbi Nuryyeva², Yu-Che Lin¹, Shuai Yuan⁴, Zhao-Kui Wang⁴, Elizabeth Zhang¹, Chengyi Xiao⁵, Danlei Zhu⁶, Lang Jiang⁶, Yepin Zhao¹, Zhenxing Li⁷, Chenhui Zhu⁸, Kendall N Houk², Yang Yang¹

Affiliations

¹ Department of Materials Science and Engineering and California NanoSystems Institute, University of California, Los Angeles, Los Angeles, CA, 90095, USA.
² Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA.
³ Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
⁴ Institute of Functional Nano & Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, Suzhou, 215123, China.
⁵ Beijing Advanced Innovation Center for Soft Matter Science and Engineering & State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing, 100029, China.
⁶ Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
⁷ State Key Laboratory of Heavy Oil Processing College of New Energy and Materials China University of Petroleum (Beijing), Beijing, 102249, China.
⁸ Advanced Light Source, Lawrence Berkeley National Laboratory, Berkeley, CA, 94704, USA.

PMID: 33586281
DOI: 10.1002/adma.202006120

Abstract

The synthesis of a new molecule, SFIC-Cl, is reported, which features enhanced π-electron delocalization by spiroconjugation and narrowed bandgap by chlorination. SFIC-Cl is integrated into a single-crystal transistor (OFET) and organic light-emitting diode (OLED). The material demonstrates remarkable transport abilities across various solution-processed OFETs and retains efficient radiance in a near-infrared OLED emitting light at 700 nm. Furthermore, the intermolecular multi-dimensional connection of SFIC-Cl enables the fabrication of a single-component large-area (2 × 2 cm² ) near-infrared OLED by spin-coating. The SFIC-Cl-acceptor-based solar cell shows excellent power conversion efficiency of 10.16% resulting from the broadened and strong absorption and well-matched energy levels. The study demonstrates that chlorinated spiroconjugated fused systems offer a novel direction toward the development of high-performance organic semiconductor materials for hybrid organic electronic devices.

Keywords: chlorination; fused ring; organic light-emitting diode; organic solar cell; single-crystal transistor; spiroconjugation.

Abstract

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