Facile synthesis and characterization of novel coronene chromophores and their application to LCD color filters

Choi, Jun; Lee, Woo‐Sung; Sakong, Chun; Yuk, Sim Bum; Park, Jong Soo; Kim, Jae Pil

doi:10.1016/j.dyepig.2011.11.009

Cited by 53 publications

(31 citation statements)

References 17 publications

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“…Although the dyes have superior optical properties than the pigments, they were hardly applied for LCD color filters owing to their inferior thermal stability. For dyes to be used as color filters, they should endure a temperature of 220°C, which is the current highest temperature in the LCD manufacturing process, without significant weight loss [9,10]. As the result of TGA measurement, all three substances showed T d value of over 240°C, confirming the thermal stability (see Figure 6).…”

Section: Resultsmentioning

confidence: 78%

Synthesis and characterization of titanium complex with a dithiolate ligand for green LCD color filter dyes

et al. 2012

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Three green compounds for color filter dyes based on bis(cyclopentadienyl) titanium complexes including dithiolate ligand were synthesized. Physical properties by the change of the substitution groups of the synthesized materials were systematically examined. UV-visible absorption spectrum of the synthesized materials showed maximum absorbing wavelengths of 427 to 430 nm and 632 to 635 nm in solution state, and 434 to 438 nm and 637 to 651 nm in film state, indicating green and black colors. It was observed that the extinction coefficient values (log ε) of all the synthesized materials are very high at 4.0 or above. In addition, it was shown that since the Td values of three synthesized materials show thermal stability higher than 240°C, they possess high potential to be applied as dyes for LCD color filter and black matrix addictive.

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Section: Resultsmentioning

confidence: 78%

Synthesis and characterization of titanium complex with a dithiolate ligand for green LCD color filter dyes

et al. 2012

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“…N,N 0 -Bis(R 1 )-1,(7)-dibromoperylene-3,4,9,10-tetracarboxydiimide (3,4): terminal-position substitution…”

Section: Synthesismentioning

confidence: 99%

“…A highly efficient color filter is critical in the development of the high-performance LCDs [3,4]. Notably, dyebased color filters have particular technical advantages in regard to their optical properties owing to reduced light scattering due to the small particle size in the film state; this causes color filters and displays to exhibit superior transmittance to pigment-based one [5].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of novel perylene dyes with new substituents at terminal-position as colorants for LCD color filter

Kim

Choi

Namgoong

et al. 2015

J Incl Phenom Macrocycl Chem

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Six novel red perylene dyes were synthesized by modifying the bay-and terminal-positions of perylene main body to improve the optical performances of liquid crystal display (LCD) color filters. The absorption properties, solubility in industrial solvents and thermal stabilities of the dyes were examined to evaluate the dyes for dye-based LCD color filter. Mill bases and spin-coated color filters were formulated and fabricated using the synthesized dyes. Transmittance, dye aggregation and thermal stabilities of the prepared color filters were investigated using a color spectrophotometer. Geometric structures of the synthesized dyes were optimized by using Gaussian program. Five of the synthesized dyes showed acceptable optical properties as colorants for LCD color filters. Also, the synthesized dyes and prepared color filters exhibited suitable thermal stability for the application. Furthermore, the prepared color filters exhibited superior transmittances than pigment-based color filters at 650 nm. Their physical properties were closely related with chemical structures investigated by geometry optimization.

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“…Due to these desirable attributes, PDIs and PTCDs have been used in a variety of applications in the field of organic electronics and optical devices, such as organic light-emitting diodes (OLEDs) [17,18], organic field-effect transistors (OFETs) [19,20], photochromic materials [21,22], molecular wires [23,24], LCD color filters [25,26], light-harvesting arrays [27,28] and organic solar cells (OSCs) [29,30,31,32]. PDIs and PTCDs have also been utilized in many other applications such as artificial photosynthetic systems through controlled supramolecular architectures via intermolecular π-π stacking [33,34].…”

Section: Introductionmentioning

confidence: 99%

1,6- and 1,7-Regioisomers of Highly Soluble Amino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties

2015

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1,6- and 1,7-regioisomers of diamino-substituted perylene tetracarboxylic dianhydrides (PTCDs) with different n-alkyl chain lengths (n = 6, 12 or 18) were synthesized and characterized by NMR spectroscopy and high-resolution mass spectrometry. These dyes are highly soluble in most organic solvents and even in nonpolar solvents, such as hexane. To the best of our knowledge, this is the first time the 1,6-diamino-substituted PTCDs (2a–2c) have been obtained in pure form. The regioisomers 1a–1c (1,7-) and 2a–2c (1,6-) exhibit significant differences in their optical characteristics. In addition to the longest wavelength absorption band at around 674 nm, 2a–2c exhibit another shoulder band at ca. 600 nm, and consequently, cover a large part of the visible region relative to those of 1a–1c. Upon excitation, 2a–2c also show larger dipole moment changes than those of 1a–1c; the dipole moments of all compounds have been estimated using Lippert–Mataga equation. Moreover, all the dyes show a unique charge transfer emission in the near-infrared region, of which the peak wavelengths exhibit strong solvatochromism. They all exhibit one irreversible one-electron oxidation and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory calculations performed on these chromophores are reported in order to rationalize their electronic structure and optical properties.

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Facile synthesis and characterization of novel coronene chromophores and their application to LCD color filters

Cited by 53 publications

References 17 publications

Synthesis and characterization of titanium complex with a dithiolate ligand for green LCD color filter dyes

Synthesis and characterization of titanium complex with a dithiolate ligand for green LCD color filter dyes

Synthesis and characterization of novel perylene dyes with new substituents at terminal-position as colorants for LCD color filter

1,6- and 1,7-Regioisomers of Highly Soluble Amino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties

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