title: Aminonaphthalic anhydrides as red-emitting materials: electroluminescence, crystal structure, and photophysical properties.
abstract: The red and orange emitters (ANA-1-3) consisting of a 4-amino-1,8-naphthalic anhydride group were synthesized. The lowest absorption band of these ANA molecules centered at approximately 450 nm is assigned to be a charge-transfer transition with emission at 514-536 nm in nonpolar solvents such as n-hexane and at approximately 590-640 nm in polar solvents such as THF and CH(2)Cl(2) and in the solid states. Emission lifetimes are measured with time-correlated single photon counting. Shorter lifetimes are observed for the ANA molecules when dissolved in polar solvents compared with those in nonpolar solvents. Strong dipole-dipole interaction of ANA molecules with solvents is indicated. At high concentrations the measured emission lifetimes, generally shortened from self-quenching, are found to remain about the same order of magnitude in ANAs. This implies that the exciton states of aggregates are formed and they exhibit a relatively long lifetime. Crystallographic data of 4-(phenyl antracen-9-yl) (ANA-2) and 4-(phenyl-2-naphthyl) amino-1,8-naphthalic anhydrides (ANA-3) show that the molecules exist as dimeric structures with antiparallel head-to-tail stacking of naphthalic anhydride planes in addition to other pi-pi stacking. The strong dipole-dipole interactions and the pi-pi stacking account for the observed red-shifted emissions of ANAs in the powders. For films prepared from vacuum sublimation, a structure similar to that in the crystal but with less crystalline order is expected based on the emission wavelength. Several electroluminescent devices based on these ANAs are reported here; they emit orange-red light at 602-628 nm with high brightness and steady external quantum efficiency.
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 30013, Republic of China.
authors.forename: Aminul
authors.initials: A
authors.lastname: Islam
authors.forename: Ching-Chi
authors.initials: CC
authors.lastname: Cheng
authors.forename: San-Hui
authors.initials: SH
authors.lastname: Chi
authors.forename: Sheng Jui
authors.initials: SJ
authors.lastname: Lee
authors.forename: P Gayatri
authors.initials: PG
authors.lastname: Hela
authors.forename: I-Chia
authors.initials: IC
authors.lastname: Chen
authors.forename: Chien-Hong
authors.initials: CH
authors.lastname: Cheng