Luminescent organic and organometallic compounds based on 7-azaindole, 2,2'-dipyridylamine, 8-hydroxyquinoline and derivatives and their electroluminescent applications

The subject of this thesis is the syntheses of luminescent organic and organometallic compounds based on 7-azaindole, 2,2'-dipyridylamine, 8-hydroxyquinoline and their derivatives, as well as investigations of the electroluminescent properties of these new compounds by fabricating light-emitting devices. Six series of new luminescent compounds including blue luminescent organoaluminum compounds of 7-azaindole derivatives, blue luminescent organoboron compounds of 7-azaindole and 2,2'-dipyridylamine, green luminescent organoboron compounds of 8-hydroxyquinoline and 2-(2-pyridyl)indole, blue luminescent organic compounds of 7-azaindole derivatives, blue luminescent zinc compounds of 7-azaindole and its derivatives and orange luminescent organopalladium compounds of 7-azaindole derivatives were synthesized and characterized by NMR, mass spectroscopy, elemental analyses and X-ray diffraction analyses.;The fluxional behaviors of blue luminescent Al3(mu 3-O)(CH3)3(7-azain-2-Ph)4 (2.4 ) (7-azain-2-ph = 2-phenyl-7-azaindole anion), Al3(mu 3-O)(CH3)3(7-azain-2-CH3)4 (2.5) (7-azain-2-CH3 = 2-methyl-7-azaindole anion), B3O3Ph3(7-azain-H) (7-azain-H = 7-azaindole) (3.3), Zn(NPA)(CH3COO)2 (6.2) (NPA = N-(2-pyridyl)-7-azaindole) and Zn(NPA)(S-(+)-CH3CH 2CH(CH3)COO)2 (6.3) were investigated by NMR. Variable-temperature 1D and low-temperature 2D EXSY 1H NMR experiments established that compounds 2.4 and 2.5 are highly fluxional in solution, attributable to an unusual intermolecular migration of coordinated 7-azain-2-R ligands. In solution compounds 3.3, 6.2 and 6.3 undergo intermolecular exchange processes.;Organoaluminum and organoboron compounds based on 7-azaindole, 2,2 '-dipyridylamine and their derivatives emit strong blue color when irradiated by UV light with emission maxima at 400--460 nm while organoboron compounds of 8-hydroxyquinoline and 2-(2-pyridyl)indole emit green or blue green color with emission maxima at 495--521 nm. Organic compounds of 7-azaindole derivatives and zinc compounds of 7-azaindole and its derivative emit purple blue or blue color when irradiated by UV light at room temperature with emission maxima at 380--434 nm, while organopalladium compounds of 7-azaindole derivatives emit orange color at 77K with emission maxima at 554--575 nm. Electroluminescent devices using compounds B2(O)(7-azain) 2Ph2 (3.5A) (7-azain = deprotonated 7-azaindole), BPh2q (4.2) (Ph = phenyl, q = 8-hydroxyquinolato), B(2-Naph)2q (4.3) (2-Naph = 2-naphthyl), B(1-Naph) 2q (4.4) (1-Naph = 1-naphthyl), 1,3,5-tri(N-7-azaindolyl)benzene (5.4) and 4,4'-di(N-7-azaindolyl) biphenyl (5.5) as emitters were fabricated. It was found that all devices emit blue or green light when a voltage around 6--14 V is applied, indicating that these compounds have promising applications in electroluminescent displays.