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Updated: Jul 31, 2025

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
New Generation of Benzidine Wide-Gap Conjugated Materials: Solution Processing a Classic Evaporated Scaffold
Pablo Simón Marqués1, Akpeko Gasonoo1, Kathryn Wolfe1
1Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4, Canada.
Abstract:
Carbazole- and fluorene-substituted benzidine blocks have been functionalized with two different solubilizing pendant groups, in order to enhance the material's solubility in greener solvents. Preserving the optical and electrochemical properties, the aromatic function and substitution showed an important influence on the solvent affinity, achieving concentrations up to 150 mg/mL in o-xylenes for the glycol-containing materials and decent solubility in alcohols for the compounds functionalized with ionic chains. The latter solution proved to be ideal for the preparation of luminescence slot-die coating film on top of flexible-substrates up to 33 cm×2 cm. As a proof of concept, the materials have been implemented in different organic electronic devices, highlighting the low turn-on voltage (4 V) presented by organic light-emitting diodes (OLEDs), which is comparable with vacuum-processed devices. A structure-solubility relationship and a synthetic strategy are disentangled in this manuscript to tailor organic semiconductors and adapt their solubility towards the desired solvent and application.
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