Fluoranthene-Based Molecules as Electron Transport and Blue Fluorescent Materials for Organic Light-Emitting Diodes

Abstract

Herein, we report the synthesis, characterization and potential application of bis(4-(7,9,10-triphenylfluoranthen-8-yl)phenyl)sulfone (TPFDPSO2) and 2,8-bis(7,9,10-triphenylfluoranthen-8-yl)dibenzo[b,d]thiophene 5,5-dioxide (TPFDBTO2) as electron transport as well as light emitting materials. These fluoranthene derivatives were synthesized by oxidation of their corresponding parent sulphide compounds which were prepared via Diels-Alder reaction. These materials exhibit deep blue fluorescence emission in both solution and thin film, high PLQY, thermal and electrochemical stability over a wide potential range. Hole-only and electron-only devices were fabricated to study the charge transport characteristics and predominant electron transport property comparable with well-known electron transport material, Alq 3 , was observed. Further, bilayer electroluminescent devices were fabricated utilizing these fluoranthene derivatives as electron transport as well as emitting layer and device performance was compared with their parent sulphide molecules. The EL devices fabricated with these molecules displayed bright sky blue color emission and 5-fold improvement in EQE with respect to their parent compounds.

A structure–property study of fluoranthene-cored hole-transporting materials enables 19.3% efficiency in dopant-free perovskite solar cells

“…The uoranthene unit is selected as the main structural framework due to its several promising advantages including low price, highly planar structure, easy functionality, and good thermal/electrochemical stability. [42][43][44] Moreover, the unique central cyclopenta-fused ring endows the uoranthene with an electron-decient character, 45 which thereby can be used as an electron-withdrawing core to construct various D-A type HTMs. 46,47 Herein, we functionalize the uoranthene moiety with methoxy-substituted triphenylamine (TPA) units on the 3-, 8-positions or 3-, 8-, 9-positions to form a linear and star-shaped structure, respectively.…”

Fluorescence of Cyclopropenium Ion Derivatives

“…N1-(2,3-Bis(diisopropylamino)cycloprop-2-en-1-ylidene)-N8,N8dimethylnaphthalene-1,8-diamine hydrochloride (Janus) (1). To a solution of tetrachlorocyclopropene (0.025 mL, 0.2 mmol) in dichloromethane (2 mL) was added freshly distilled diisopropylamine (0.11 mL, 0.8 mmol) dropwise under an inert nitrogen atmosphere.…”

“…mp = 225−230 °C. 1 N1-(2,3-Bis(dicyclohexylamino)cycloprop-2-en-1-ylidene)-N8,N8dimethylnaphthalene-1,8-diamine hydrochloride (6). To a solution of tetrachlorocyclopropene (35.6 mg, 0.2 mmol) in dichloromethane (2 mL) under an inert nitrogen atmosphere was added dicyclohexylamine (0.16 mL, 0.8 mmol).…”

“…Small molecule-based fluorophores play an integral part in day-to-day research, as light emitting diodes, − chemical sensors, − biological probes, cellular imaging agents, and light harvesting agents . Their utility is broadened by their many mechanisms of action, such as Förster resonance energy transfer, photoinduced electron transfer, aggregation and disaggregation-induced emission, , internal charge transfer, and, recently, motion-induced changes in emission .…”

9-Arylvinyl- and 9,10-bis(arylvinyl)-anthracenes with phenyl and naphthyl as aryl moieties: Differential aggregation behaviors and optoelectronic properties

“…© 2016. This manuscript version is made available under the Elsevier user license http://www.elsevier.com/open-access/userlicense/1.0/ Conjugated organic molecules exhibiting high solution and solid-state fluorescence efficiency are promising materials for the potential applications in fluorescence imaging, chemo-sensing, light emitting diodes, and active gain media for optically pumped solid-state lasers [1][2][3][4][5][6][7][8][9][10][11][12]. However, common organic chromophores show aggregation-or crystallization-quenched emission (AQE) effect due to strong intermolecular π−π stacking interactions, a typical problem of most fluorescent organic molecules [13,14].…”