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.

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.

In this research, we focused on the improvement of cy3 dye’s characteristics for LCD color filter. Solubility and thermal stability are main characteristics of dyes for LCD color filter. We performed experiment to change counter cation of cy3 dyes with alkoxy substituent for these purposes. These cy3 dyes (1b∼5b) were prepared through the synthetic procedure of three steps. The synthesized new cy3 dyes were charaterized by using NMR, FT-IR, UV/Vis spectroscopy, and TGA. These cy3 dyes showed purple color and maximum absorption wavelength (λmax) in the range of 578∼590 nm in UV/Vis spectrum. We confirmed that solubility and thermal stability of cy3 dyes were dependent on the structure of counter cation. Cy3 dyes with alkoxy substituent have good solubility in organic solvents such as dichloromethane, methanol, and acetone. Especially, Cy3 dye with 4-nitrobenzyl counter cation (5b) gave excellent solubility characteristics.

In this research, we focused on the development of cy3 dye with high thermal stability and good solubility for LCD color filter. Cy3 dyes were prepared through the synthetic procedure of two steps. The synthesized cy3 dyes were characterized by using NMR, FT-IR, UV/Vis spectroscopy, and TGA. These cy3 dyes showed maximum absorption wave length (λmax) in the range of 549∼555 nm in UV/Vis spectrum. And we confirmed that solubility characteristics and thermal stability of cy3 dyes were dependent on the structure of counter cation. Cy3 dyes with methyl counter cation and ethyl counter cation have good solubility in organic solvents such as chloroform, ethanol, and PGME. Moreover, Cy3 dye with ethyl counter cation gave excellent thermal stability in TGA thermograms. And Cy3 dye with ethyl counter cation showed good result in photoresist film test.