New Molecular Design, Step‐Saving Synthesis, and Applications of Indolocarbazole Core‐Based Oligo(hetero)arenes

Author:

Lin Li1,Chiu Wei‐Hao2,Cao Ming‐Ling1,Lee Kun‐Mu23,Yu Wei‐Lun1,Liu Ching‐Yuan1ORCID

Affiliation:

1. Department of Chemical and Materials Engineering National Central University Jhongli District Taoyuan City 320 Taiwan

2. Department of Chemical and Materials Engineering & Center for Green Technology & Division of Neonatology Department of Pediatrics Chang Gung University & Chang Gung Memorial Hospital Guishan District and Linkou Taoyuan City 333 Taiwan

3. College of Environment and Resources Ming Chi University of Technology New Taipei City 243 Taiwan

Abstract

AbstractIn this work, we have successfully synthesized 15 new examples (LLA0106; LinLi0110) of small‐molecule hole‐transporting materials (HTM) using the less explored indolocarbazole (ICbz) as core moiety. Different from previously reported ICbz HTMs, LinLi0110 exhibit new molecular designs in which 3,4‐ethylenedioxythiophene (EDOT) units are inserted as crucial π‐spacers and fluorine atoms are introdcued into end‐group molecules. These substantially improve the materials solubility and device power conversion efficiencies (PCEs) while fabricated in perovskite solar cells (PSC). More importantly, LinLi0110 are generated by a sustainable synthetic approach involving the use of straightforward C−H/C−Br couplings as key transformations, thus avoiding additional synthetic transformations including halogenation and borylation reactions called substrate prefunctionalizations usually required in Suzuki reactions. Most HTM molecules can be purified simply by reprecipitations instead of conducting column chromatography. In contrast to LLA0106 without additional EDOT moieties, PSC devices using LinLi0110 as hole‐transport layers display promising PCEs of up to 17.5 %. Interestingly, PSC devices employing seven of the LinLi0110 as hole‐transport molecules, respectively, are all able to show an immediate >10 % PCE (t=0) without any device oxidation/aging process that is necessary for the commercial spiro‐OMeTAD based PSCs.

Funder

Chang Gung University

Publisher

Wiley

Subject

General Chemistry,Biochemistry,Organic Chemistry

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