Boronsubphthalocyanines (BsubPcs) are a class of organic semiconducting materials which are relatively underdeveloped in their synthetic methods and organic semiconducting applications. A comprehensive investigation of these materials is explored in a rigorous and strategic manner progressing through each stage of the materials development cycle: materials selection from computational screening, organic/organometallic synthesis of target materials using known methods or by the development of new synthetic methods, physical and chemical analysis of new materials, and device implementation in organic light emitting diodes and organic photovoltaic cells. The result is the formation of new compositions of BsubPc specifically engineered for application as organic semiconductors in devices.
Specifically, phenoxy-boronsubphthalocyanine derivatives are investigated starting with a computational study of their molecular orbitals – a property that dictates their function (donor or acceptor behaviour) in organic electronic devices. The nature of the axial phenoxylate is found to vary the energy level of the frontier molecular orbitals minimally, by up to ~0.4 eV while the nature of the BsubPc periphery can shift the energy levels of the frontier molecular orbitals by >1 eV. The differential sensitivity of the axial phenoxylate and the BsubPc periphery becomes a key design element allowing controlled adjustments of the frontier molecular orbitals by peripheral modification and isolating the design physical chemical properties essential to device fabrication to the axial phenoxylate. Subsequently, an investigation into the solubility and sublimability of these materials is performed, which leads to their investigation in OLED and OPV devices.
The success from the phenoxy-BsubPcs study has led to the exploration of new chemistry to expand the available axial nucleophiles beyond phenoxylates. Previously unattainable sulphur and nitrogen nucleophiles are synthesised using two methods (1) the condensation of Cl-BsubPc with phthalimides and (2) the activation of Cl-BsubPc using aluminum chloride to access thiols and anilines. The phthalimido-BsubPcs synthesized from this method are incorporated in OLEDs.
| Identifer | oai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/35083 |
| Date | 04 March 2013 |
| Creators | Morse, Graham Edward Jr. |
| Contributors | Bender, Timothy |
| Source Sets | University of Toronto |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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