Synthesis of organic and inorganic compounds for OLED application: Physico-chemical characterization of new diamines, heterocycles and group 13 compounds

This thesis is focused on the synthesis and characterization of organic and inorganic electroluminescent materials for organic light-emitting diodes (OLED). The synthetic work was aimed at several of the key components of multilayer OLEDs and followed the latest developments in this area. Three types of OLED materials, namely hole-transport (HT), electron-transport (ET) and emission (EM) materials in four groups were successfully synthesized. The characterization of these materials focuses on the physical and chemical features that are important in defining performance parameters. This chemist's perspective highlights the potential application of these novel compounds employed in fabricating OLEDs, which is based on the results from thermal, photophysical and electrochemical analysis.; Chapter one outlines the background of OLED, the operation of a double-layer and multilayer OLEDs and the current state of OLED materials. The objectives of this thesis are proposed after describing the general techniques that are important for characterization of the parameters needed for further OLED fabrication.; Chapter two focuses on the synthesis and characterization of HT materials based of aryldiamines with a naphthalene core (bis(N;N-diaryl)-1,5-diaminonaphthalene). Pd-based catalysts have been employed in the C-N bond formation steps of the synthesis of these compounds. The thermal results indicated that these diamines, particularly when they possess bulky aryl groups such as biphenyl and naphthyl, had high glass transition temperatures and thus offer the potential for improving upon OLED stability.; Chapter three is concerned with developing C-4 substituted tris(8-hydroxyquinoline) aluminum (Alq3) derivatives. Alq3 is frequently used as both an ET and an EM material in OLEDs. The modification of the C-4 position of Alq3 and the subsequent influence on the LUMO energy was investigated.; In Chapter four, we investigated EM materials by preparing and characterizing substituted salicylaldimine diphenylboron complexes. Thermal characterization of these compounds indicated that a bulky substituent was needed to improve the thermal stability of these boron complexes.; Chapter five reports our effort to synthesize a novel ET material that was designed as a perimidine-based analogue of 2,2 ',2″-(Benzene-1,3,5-triyl)-tris(1-phenyl-1H-benzimidazole) (TPBI).; In Chapter six, a broad summary of these efforts and future prospects are presented. (Abstract shortened by UMI.)...