Synthesis, physical properties, and light-emitting diode performance of phenazine-based derivatives with three, five, and nine fused six-membered rings

J Org Chem. 2015 Mar 20;80(6):3030-5. doi: 10.1021/jo5027707. Epub 2015 Mar 9.

Abstract

Realizing the control of emission colors of single molecules is very important in the development of full-color emitting materials. Herein, three novel phenazine derivatives (2,3,7,8-tetrakis(decyloxy)phenazine (2a), 2,3-didecyloxy-5,14-diaza-7,12-dioxo-9,10- dicyanopentacene (2b), and 2,3,13,14-tetradecyloxy-5,11,16,22-tetraaza-7,9,18,20-tetraoxo-8,19-dicyanoenneacene (2c)) have been successfully synthesized and fully characterized. Compound 2c can emit blue light in toluene solution (450 nm), green light in the powder/film state (502/562 nm), and red light in the 2c/TFA state (610 nm). The OLED with 2c emits a strong green light at a peak of 536 nm with a maximum luminance of the OLED of about 8600 cd m(-2), which indicates that 2c could be a promising fluorescent dye for OLED applications.