Core Fluorination Enhances Solubility and Ambient Stability of an IDT‐Based n‐Type Semiconductor in Transistor Devices. (26th February 2020)

• Record Type: Journal Article
• Authors: Hodsden, Thomas; Thorley, Karl J.; Panidi, Julianna; Basu, Aniruddha; Marsh, Adam V.; Dai, Haojie; White, Andrew J. P.; Wang, Changsheng; Mitchell, William; Glöcklhofer, Florian; Anthopoulos, Thomas D.; Heeney, Martin
• Is Part Of: Advanced functional materials. Volume 30:Number 17(2020)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2020-02-26
• Subjects: ambient stability -- fluorination -- n‐type semiconductors -- organic field‐effect transistors -- small molecules; Materials -- Periodicals; Chemical vapor deposition -- Periodicals; 620.11
• DOI: 10.1002/adfm.202000325
• Languages: English
• ISSNs: 1616-301X

Abstract

Abstract: The synthesis of a novel fluorinated n‐type small molecule based on an indacenodithiophene core is reported. Fluorination is found to have a significant impact on the physical properties, including a surprisingly dramatic improvement in solubility, in addition to effectively stabilizing the lowest‐unoccupied molecular orbital energy (−4.24 eV). Single‐crystal analysis and density functional theory calculations indicate the improved solubility can be attributed to backbone torsion resulting from the positioning of the fluorine group in close proximity to the strongly electron‐withdrawing dicyanomethylene group. Organic thin‐film transistors made via blade coating display high electron mobility (up to 0.49 cm 2 V −1 s −1 ) along with good retention of performance in ambient conditions. Abstract : A novel fluorinated n ‐type small molecule diFIDT‐di(C(CN)2 ) that displays unipolar electron mobility up to 0.49 cm 2 V −1 s −1 along with good retention of performance in ambient conditions in solution‐processed organic field‐effect transistors is reported. Fluorination is found to cause a surprisingly dramatic improvement in solubility, which is attributed to the increased van der Waals radius of fluorine inducing distortion of the π‐conjugated system.