Synthesis of a novel hole-transporting agent applicable to organic light emitting diodes

CHED 888

Nathan W Coleman and J. Thomas Ippoliti. Department of Chemistry, University of St. Thomas, 2115 Summit Ave., St. Paul, MN 55105
The synthesis of compounds with ideal properties for functioning efficiently in organic light emitting diodes has, over the past ten years, been the subject of much research. Synthesis of a new hole-transporting agent was the final goal, and progress toward this goal is described. 2,6-Cycloheptadienone was synthesized by two alternate routes. The 2,6-cycloheptadienone was reacted with 4-bromoaniline to form a key intermediate (8-(4-bromophenyl)-8-aza-bicyclo[3.2.1]octan-3-one) via a double Michael addition on route to the new hole-transporting agent. This key intermediate was characterized using NMR, its synthesis, supporting data and analysis is described. The use of this intermediate as an important starting material in the synthetic schemes for three different but related hole-transporting agents is described.