1,8-Naphthalimides for non-doping OLEDs: the tunable emission color from blue, green to red

Abstract

Substitution at the 4-position of 1,8-naphthalimide with electron-donating groups can increase fluorescent quantum yields and change emissive wavelengths from blue to red. Based on this molecular design concept, novel naphthalimide derivatives containing Schiff base moiety were prepared by condensing 4-hydrazino-1,8-naphthalimides with the aldehydes. Amino conjugation between the 4-amino-1,8-naphthalimide and the substituted moiety resulted in red shift of the absorption and fluorescence maximum wavelengths in the acetonitrile solution and in the net solid film. In the meantime, concentration-quenching effect of fluorescence for common luminescent materials was avoided. Some of these dyes emit brilliant red fluorescence in solid films and were used as non-doping emissive materials to fabricate electroluminescence devices. Based on these results, guidelines for the molecular design of non-doping red emissive materials for OLED applications are presented in this paper.

Design and Synthesis of Long‐Wavelength Fluorescent Boronic Acid Reporter Compounds

“…Because the 1,8-naphthalimide fluorophore offers the possibility of long-wavelength emission, and recently it has been reported that addition of a 4-amino group can significantly change the fluorescent properties of the 1,8-naphthalimide fluorophore, [59][60][61][62][63] we were interested in using 4-amino-1,8-naphthalimide as a template for the design of long-wavelength fluorescent boronic acid reporter compounds. One way to induce the desired fluorescent property changes to such a template is to build in a mechanism in which binding of a sugar would perturb the fluorophore's electronic environment.…”

Synthesis, Evaluation, and Computational Studies of Naphthalimide‐Based Long‐Wavelength Fluorescent Boronic Acid Reporters

“…[36] Long-wavelength emission has been observed with the 1,8-naphthalimide fluorophore, and the addition of a 4-amino group to this compound has been shown to significantly change its fluorescence properties. [12,[37][38][39] In our recent work, 4-amino-1,8-naphthalimide was used as a template for a series of long-wavelength fluorescent boronic acid reporters that showed fluorescence intensity increases upon sugar binding. [13] Somewhat related work was also reported by Trupp and co-workers.…”

Highly Efficient Pure‐White‐Light‐Emitting Diodes from a Single Polymer: Polyfluorene with Naphthalimide Moieties

“…Therefore, PF was chosen as the blue-lightemitting polymer, and 1,8-naphthalimide derivatives were chosen as the orange-light-emitting components, owing to their high photoluminescence (PL) quantum yields, tunable emission colors, and their ability to be attached to the polymer main and side chains. [30][31][32] For example, Ego et al reported that the emission color of fluorene-based polymers can be easily tuned across the whole visible range of the electromagnetic spectrum by incorporating perylene bisimide units in the main chain, as side chains, and at the chain termini. [32] The amount of 1,8-naphthalimide derivative in the resulting polymers was maintained in the 0.05-1.0 mol-% range in order to balance the relative intensity of the blue-light emission from PF with orange-light emission from a1,8-naphthalimide derivative unit.…”