Synthesis, Characterization, and Physical Properties of Pyrene‐Naphthalimide Derivatives as Emissive Materials for Electroluminescent Devices

Abstract

A series of axially linked pyrene‐naphthalimide fluorophores (N2Py, N4Py, and BNPy) bearing a different number of 1,8‐naphthalimide units substituted on pyrene and bis‐pyrene cores were designed and synthesized using palladium‐catalyzed cross‐coupling reactions in a stepwise synthetic manner. These molecules were chemically characterized, and their photoelectric properties were explored by spectroscopy, electrochemical and theoretical studies. They exhibited push‐pull characteristics with intense fluorescence in solutions, strong solvatochromic behaviors, good thermal and electrochemical stabilities. N2Py, N4Py, and BNPy were successfully applied as emitters in solution‐processed OLED devices, which resulted in blue‐green emissions with promising device performance. Particularly, the BNPy‐based device achieved the best EL results with a maximum brightness of 3389 cd m−2, a maximum EQE of 3.98 %, a maximum LE of 3.22 cd A−1, and a low turn‐on voltage of 3.2 V.

A systematic review on 1,8-naphthalimide derivatives as emissive materials in organic light-emitting diodes

“…Pyrene-incorporated NI-based derivatives (9, 10 and 11) were synthesized by Boonnab et al using palladium-catalyzed cross-coupling reactions, and used to fabricate OLED devices [98]. The 4-bromo-1,8-naphthalic anhydride was first alkylated, converted to the corresponding boronic acid pinacol ester by borylation with bis(pinacolato)diboron catalyzed by Pd(PPh 3 )Cl 2 /KOAc and then treated with 1,3,6,8-tetrabromopyrene to yield 9, 10 and 11 (Fig.…”

Aryl‐Bridged Thienonaphthalimides: Synthesis, Characterization and Optoelectronic Properties

“…[10] Small molecules based on NI fragments connected by various linkers into an extended π-conjugated system are of interest for organic electronics. [11] Typically they are used as non-fullerene acceptors in organic solar cells (OSCs), less often as emitters in organic light-emitting diodes (OLEDs) [12] or as nchannel semiconductors in organic field-effect transistors. [13] At the same time, cyclo-fused or cyclo-R-substituted NIs are also prospective for use in different organic electronic devices.…”

Polymorphs, ionic cocrystal and inclusion complex of N-amino-1,8-naphthalimide

“…The optical, 1–15 magnetic, 6–8 and electrochemical 9,10 properties of discrete or self-assemblies of naphthalimide derivatives as well as their metal complexes are generally influenced by hydrogen bonds and π-interactions. The abilities of naphthalimide derivatives to recognize molecules and ions make them useful probes in studying biologically related systems.…”