Anthracene-Based Molecules for Organic Thin-Film Transistor Integration

Abstract

Organic electronics are devices based on semiconductors derived from carbon based molecules and polymers. These devices can be made flexible, lightweight and potentially inexpensive with the development of economies of scale. Specific examples of organic electronics include organic thin-film transistors (OTFTs), organic light-emitting diodes (OLEDs) and organic photovoltaic (OPVs). Anthracene-based semiconductors are materials that have generated great interest primarily because of their structural planarity, potential for strong intermolecular interactions, air stability and ideal frontier molecular orbital energy levels. In this thesis, we detail two publications that examined functionalized anthracene molecules integrated into OTFTs, along with their thermal, electrochemical and optical properties. We started by examining seven novel 9,10-anthracene-based molecules. It was found that functionalization of the 9,10-positions with different phenyl derivatives resulted in negligible variation in the optical properties with minor (±0.10 eV) changes in electrochemical behaviour, while the choice of phenyl derivative greatly affected the thermal stability whereby the decomposition temperatures (Td) varied by as much as 128 °C between certain functionalized derivatives. The findings suggested that functionalization of the 9,10-position of anthracene leads to an effective handle for tuning of the thermal stability while having little to no effect on the optical properties and the solid-state arrangement. We continued with the synthesis of several novel anthracene derivatives which were di-substituted at the 2,6-positions. It was found that 2,6-functionalization with various fluorinated phenyl derivatives led to negligible changes in the optical behaviour while influencing the electrochemical properties (±0.10 eV). Furthermore, the choice of fluorinated phenyl moiety had noticeable effects on melting point and thermal stability (ΔTm < 55 °C and ΔTd < 65 °C). OTFTs were fabricated and characterized using the 2,6-anthracene derivatives as the semiconducting layer. The addition of fluorine groups on the phenyl groups led to a transition from p-type behaviour to n-type behaviour in BGBC OTFTs. The results indicated that the choice of functional group as well as its functionalization location, at the 9,10- and 2,6-positions, can act as powerful handles to engineer high performance OTFTs.