• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.32 no.1
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• pp.86-92
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• 2019

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 $242^{\circ}C$. 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.

• Bulletin of the Korean Chemical Society
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• v.31 no.9
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• pp.2705-2708
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• 2010

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.30 no.9
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• pp.577-582
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• 2017

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 $70^{\circ}C$. 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.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.30 no.1
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• pp.48-53
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• 2017

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 $70^{\circ}C$. 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 $220^{\circ}C$. 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.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.24 no.5
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• pp.398-403
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• 2011

Recently, Near-infrared (NIR)colorant is intriguing and attractive but full of challenges. Although some cyanine colorant have been commercialized, near-infrared colorant with intensive NIR absorption, good chemical and photo-stability, and high solubility still remain as target compound. Certain polycyclic aromatic compounds such as quaterrylene represent a key class of NIR colorant and also give rise to outstanding physical and chemical properties after appropriate chemical modification. In this study, We have tried to introduceimide functional group to quaterrylene in order to give chemical and thermal stability. Finally, N,N'-bis (2,6-diisopropylphenyl)-quarterrylene-3,4:13,14-tetracarboximide was synthesized and evaluated its properties using $^1H$ NMR, Maldi-tof, TGA, and UV/VIS/NIR spectroscopy as NIR colorant. The quaterrylene bisimide compound exhibit a excellent thermal stability and chemical stability.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.25 no.2
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• pp.140-146
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• 2012

A variety of dyes are commercially available today, there is an ongoing need for new chromophoric systems and low-band-gap materials. For example, near-infrared (NIR) emission has received increased attention for applications in bioassays and medicine while NIR absorption is demanded for laser-welding of plastics or efficient blocking of heat rays. Most of the commercially available NIR materials are not suitable for such purposes owing to their insufficient stability. We have developed a novel NIR-absorbing polyaromatic dye. By extending the system of perylenebis(dicarboximide)s along the molecular long axis, we have obtained the higher homologue pentarylenebis(dicarboximide). We have tried to introduce imide functional group to pentarylene in order to increase chemical and thermal stability.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.33 no.3
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• pp.194-200
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• 2020

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.

• Journal of the Korean Chemical Society
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• v.63 no.1
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• pp.37-44
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• 2019

N,N'-bis(ethyldihydrogen phosphate)-1,4,5,8-naphthalene bis(dicarboximide) (EPNI) and N,N'-bis(ethyldihydrogen phosphate)-3,4,9,10-perylene bis(dicarboximide) (EPPI) and their zirconium bisphosphate multilayers (Zr-EPNI and Zr-EPPI), that had been briefly reported by us, were further investigated in terms of their electrochemical properties. EPNI in aqueous solution showed typical two reversible reductions at ITO electrode but the reductions were strongly dependent on solution pH while EPPI showed only an irreversible reduction. The single and mixed multilayers of Zr-EPNI and Zr-EPPI were well constructed on ITO electrode by the alternate adsorptions of zirconium ion and the bisimides. While Zr-EPNI multilayer on ITO electrode showed single broad reversible reduction with $E_{1/2}=-0.68V$, Zr-EPPI gave two separated reductions at $E_{1/2}=-0.54$ and -0.81 V vs SCE, quite differently from the solution properties. The average layer densities of the multilayers were estimated as $1.5{\times}10^{-10}$ and $2.3{\times}10^{-10}mol/cm^2$ for Zr-EPNI and Zr-EPPI, respectively. Both the monolayers of Zr-EPNI and Zr-EPPI could not completely block the electron transfer between $Fe(CN){_6}^{3-}$ in solution and ITO electrode but 3-5 layers of Zr-EPNI and Zr-EPPI could block it completely and mediated the one-way electron transfer at the potential shifted to their reduction potentials. When the monolayer of zirconium 1,10-decanediylbisphosphonate (Zr-DBP) was used as a sublayer of Zr-EPNI and Zr-EPPI layers, the mediated electron transfer became prominent without any direct electron transfer.