Modulation of the Physicochemical Properties of Donor-Spiro-Acceptor Derivatives through Donor Unit Planarisation: Phenylacridine versus Indoloacridine-New Hosts for Green and Blue Phosphorescent Organic Light-Emitting Diodes (PhOLEDs)

Chemistry. 2016 Jul 11;22(29):10136-49. doi: 10.1002/chem.201600652. Epub 2016 Jun 13.

Abstract

This work reports a detailed structure-property relationship study of a series of efficient host materials based on the donor-spiro-acceptor (D-spiro-A) design for green and sky-blue phosphorescent organic light-emitting diodes (PhOLEDs). The electronic and physical effects of the indoloacridine (IA) fragment connected through a spiro bridge to different acceptor units, namely, fluorene, dioxothioxanthene or diazafluorene moiety, have been investigated in depth. The resulting host materials have been easily synthesised through short, efficient, low-cost, and highly adaptable synthetic routes by using common intermediates. The dyes possess a very high triplet energy (ET ) and tuneable HOMO/LUMO levels, depending on the strength of the donor/acceptor combination. The peculiar electrochemical and optical properties of the IA moiety have been investigated though a fine comparison with their phenylacridine counterparts to study the influence of planarisation. Finally, these molecules have been incorporated as hosts in green and sky-blue PhOLEDs. For the derivative SIA-TXO2 as a host, external quantum efficiencies as high as 23 and 14 % have been obtained for green and sky-blue PhOLEDs, respectively.

Keywords: donor-acceptor systems; electrochemistry; luminescence; spiro compounds; structure-activity relationships.