Although perylene bisimide derivatives have advantages such as excellent thermal stability and high luminance efficiency, they have poor solubility characteristics in organic solvents. In this research, in order to improve the solubility characteristics, we prepared perylene bisimide derivatives (1C) and (2C) with swallow-tail substituted imide, which is known to lead to excellent solubility. The structures and properties of swallow-tail perylene bisimide (1C) and (2C) were analyzed by ¹H-NMR, FT-IR, UV/Vis spectroscopy, and thermogravimetric analysis (TGA). The maximum absorption wavelengths of (1C) and (2C) in the UV/Vis spectrum were 558 nm and 556 nm, respectively, and the maximum emission wavelengths were 602 nm and 600 nm, respectively. In the TGA, (1C) demonstrated good thermal stability with less than 5 wt% weight loss up to 242℃. In the solubility test, (1C) and (2C) exhibited solubilities of more than 5 wt% in chloroform, ethyl acetate, and dimethylformamide, but not in methanol. When the compounds (1C) and (2C) were mixed with PMMA (polymethyl methacrylate), thin films showed peaks at 679 nm and 677 nm, respectively, in the photoluminescence spectra. (1C) was found to be a possible candidate as red organic phosphor for hybrid LEDs.

The white light of a hybrid LED is obtained by using red and green organic fluorescent layers made of polymethylmethacrylate (PMMA) films, which function as color down-conversion layers of blue light-emitting diodes. In this research, we studied the fluorescence properties of a red organic fluorophore, employing perylene bisimide derivatives applicable to hybrid LEDs. The solubility, thermal stability, and luminous efficiency are important characteristics of organic fluorophores for use in hybrid LEDs. The perylene fluorescent compounds (1A and 1B) were prepared by the reaction of 4-bromophenol and 4-iodophenol with N,N`-bis(4-bromo-2,6-diisopropylphenyl)-1, 6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxyl diimide (1) in the presence of dimethyl formaldehyde (DMF) at 70℃. The synthesized derivatives were characterized by using 1H-NMR, FT-IR, UV/Vis absorption and PL spectra, and TGA analysis. Compounds 1A and 1B showed absorption and emission at 570 nm and 604 nm in the UV/Vis spectrum. We also documented favorable solubility and thermal stability characteristics of the perylene fluorophores in our work. Perylene fluorophore 1, with the 4-bromophenol substituent 1A, exhibited particularly good thermal stability and solubility in organic solvents.

We report the studies on the red organic phosphor by using perylene bisimide derivatives. Even though perylene bisimide derivatives have excellent thermal stability and luminous efficiency, they have low solubility in organic solvents. In this research, modified perylene bisimide derivative, N,N`-Bis(4-bromo-2, 6-diisopropylphenyl)- 1, 6, 7, 12-tetraphenoxyperylene-3, 4, 9, 10-tetracarboxyl bisimide (1C), has been prepared by the reaction of phenol with N,N`-Bis(4-bromo-2, 6-diisopropylphenyl)-1, 6, 7, 12-tetrachloroperylene-3, 4, 9, 10-tetracarboxyl bisimide (1B) in presence of DMF, at 70℃. The synthesized (1C) was characterized by using 1H-NMR, FT-IR, UV/V is spectroscopy, and TGA. The absorbtion and emission of (1C) was shown at 576 nm and 610 nm in UV/V is spectrum. In TGA thermogram, (1C) showed good thermal stability without significant weight loss to 220℃. And in the solubility analysis, (1C) with phenoxy group showed the good solubility in general organic solvents. The blended films of (1C) with PMMA (polymethyl methacrylate) at different weight % concentration such as 10, 5, 1 weight % have been prepared. The blended film was shown at 616 nm when monitored at 450 nm in PL emission spectra.