Design rules for high mobility xanthene-based hole transport materials. Issue 36 (30th July 2019)

• Record Type: Journal Article
• Authors: Tabor, Daniel P.; Chiykowski, Valerie A.; Friederich, Pascal; Cao, Yang; Dvorak, David J.; Berlinguette, Curtis P.; Aspuru-Guzik, Alán
• Is Part Of: Chemical science. Volume 10:Issue 36(2019)
• Page Start: 8360
• Page End: 8366
• Publication Date: 2019-07-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc01491h
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A set of design principles for high mobility xanthene-based organic hole transport materials are elucidated by combining multiple scales of theoretical chemistry (from virtual screening to bulk simulation) with experimental synthesis and characterization. Abstract : Tunable and highly conductive hole transport materials are crucial for the performance of organic electronics applications such as organic light emitting diodes and perovskite solar cells. For commercial applications, these materials' requirements include easy synthesis, high hole mobility, and highly tuned and compatible electronic energy levels. Here, we present a systematic study of a recently discovered, easy-to-synthesize class of spiro[fluorene-9, 9′-xanthene]-based organic hole transport materials. Systematic side group functionalization allows us to control the HOMO energy and charge carrier mobility. Analysis of the bulk simulations enables us to derive design rules for mobility enhancement. We show that larger functional groups ( e.g. methyl) decrease the conformational disorder due to steric effects and thus increase the hole mobility. Highly asymmetric or polar side groups ( e.g. fluorine), however, increase the electrostatic disorder and thus reduce the hole mobility. These generally applicable design rules will help in the future to further optimize organic hole transport materials.