Perylene bisimide derivatives are developed for red organic phosphor because of their advantages, such as excellent luminous efficiency and high thermal stability. Despite these advantages, they have poor solubility characteristics in organic solvents and short emission wavelength as red organic phosphor for hybrid light-emitting diodes (LEDs). In this study, we prepared terrylene bisimide using a coupling reaction and swallow-tail imide group, which has excellent solubility. The structures and properties of swallow-tail terrylene bisimide (9C) were analyzed using ¹H-nuclear magnetic resonance (¹H-NMR), Fourier-transform infrared (FT-IR), UV/Vis spectroscopy, and thermal gravimetric analysis (TGA). The maximum absorption wavelength of (9C) in the UV/Vis spectrum was 647 nm, and the maximum emission wavelength was 676 nm. In the TGA, (9C) demonstrated good thermal stability with less than 5 wt% weight loss up to 415℃. In the solubility test, (9C) has a good solubility of more than 5 wt% in chloroform and dichloromethane. When the compounds (9C) were mixed with PMMA (polymethly methacrylate), the films showed peaks at 680 nm in the PL spectra. The results verify the suitability of (9C) as a red organic phosphor for hybrid LEDs.

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.