Application of perylene dyes for low dielectric hybrid-type black matrices

Sim Bum Yuk; Woosung Lee; Se Hun Kim; Jin Woong Namgoong; Jae Moon Lee; Jae Pil Kim

Journal of Industrial and Engineering Chemistry, Vol.64, 237-244, August, 2018

DOI10.1016/j.jiec.2018.03.021 Export Citation

Application of perylene dyes for low dielectric hybrid-type black matrices

Sim Bum Yuk¹, Woosung Lee², Se Hun Kim^{1, 3}, Jin Woong Namgoong¹, Jae Moon Lee¹, and Jae Pil Kim^{1, †}

¹Department of Materials Science and Engineering, Seoul National University, Seoul 151-744, Republic of Korea
²Smart Textile Group, Korea Institute of Industrial Technology (KITECH), 143 Hanggaulro, Sangrokgu, Ansan-si, Gyeonggi-do, 426-910, Republic of Korea
³EM Development Team, ChemE Inc., 199, Techno 2-ro, Yuseong-gu, Daejeon 34025, Republic of Korea

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Two perylene dyes having different absorption ranges were synthesized for an application in liquid crystal display black matrix. Hybrid-type and dye only-type black matrices were fabricated using the synthesized dyes and carbon black. Among the fabricated films, the hybrid-type film, which contained the same weight ratio of the dyes and carbon black showed high thermal and optical properties and had a low dielectric constant. Additionally, the surface of the film had low root-mean-squared roughness (Rq) value and was sufficiently flat in comparison to the film containing different chromophores that showed self-aggregation of the dyes described in previous research.

Keywords:Perylene;Dye;Carbon black;Black matrix;Dielectric constant

[References]

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Jung J, Park Y, Jaung JY, Park J, Mol. Cryst. Liq. Cryst., 529, 88 (2010)
Lee W, Yuk SB, Choi J, Jung DH, Choi SH, Park J, Kim JP, Dyes Pigment., 92, 942 (2012)
Sabnis RW, Displays, 20, 119 (1999)
Xing Y, Frank WM, David JP, Martin FS, Kyu KJ, Jaehee C, Schubert EF, Jpn. J. Appl. Phys., 48, 120203 (2009)
Bui TS, Kim J, Jung E, Le HS, Nguyen NT, Bae JY, Displays, 34, 192 (2013)
Lee CS, Yoon HJ, Yoon SI, Yoon SH, Kim DW, Jung MS, Won T, Mol. Cryst. Liq. Cryst., 436, 29 (2005)
Lee W, Choi J, Kim SH, Park J, Kim JP, J. Nanosci. Nanotechnol., 15, 295 (2015)
Yuk SB, Lee W, Namgoong JW, Choi J, Chang JB, Kim SH, Kim JY, Kim JP, J. Incl. Phenom. Macrocycl. Chem., 82, 187 (2015)
Chen Z, Baumeister U, Tschierske C, Wurthner F, Chemistry, 13, 450 (2007)
Jiang W, Xiao C, Hao L, Wang Z, Ceymann H, Lambert C, Motta SD, Negri F, Chemistry, 18, 6764 (2012)
Shoer LE, Eaton SW, Margulies EA, Wasielewski MR, J. Phys. Chem. B, 119(24), 7635 (2015)
Choi J, Sakong C, Choi JH, Yoon C, Kim JP, Dyes Pigment., 90, 82 (2011)
Kim JY, Sakong C, Choi SA, Jang H, Kim SH, Chang KS, Han MS, Lee JS, Kim JP, Dyes Pigment., 131, 293 (2016)
Sakong C, Kim YD, Choi JH, Yoon C, Kim JP, Dyes Pigment., 88, 166 (2011)
Flamigni L, Ventura B, Barbieri A, Langhals H, Wetzel F, Fuchs K, Walter A, Chemistry, 16, 13406 (2010)
Chao CC, Leung MK, Su YO, Chiu KY, Lin TH, Shieh SJ, Lin SC, J. Org. Chem., 70, 4323 (2005)
Mamada M, Pe’rez-Boli’var CS, Anzenbacher P, Org. Lett., 13, 4882 (2011)
Wurthner F, Chem. Commun. (Camb), 1564 (2004).
Li M, Xu JR, Zeng Y, Ben HJ, Yao FL, Yang S, Chen EQ, Ren XK, Dyes Pigment., 139, 79 (2017)
Huang C, Barlow S, Marder SR, J. Org. Chem., 76, 2386 (2011)
An ZS, Odom SA, Kelley RF, Huang C, Zhang X, Barlow S, Padilha LA, Fu J, Webster S, Hagan DJ, Van Stryland EW, Wasielewski SMR, Marder SR, J. Phys. Chem. A, 113(19), 5585 (2009)
Choi J, Lee W, Sakong C, Yuk SB, Park JS, Kim JP, Dyes Pigment., 94, 34 (2012)
Yoon C, Kwon HS, Yoo JS, Lee HY, Bae JH, Choi JH, Coloration Technol., 131, 2 (2015)
Wurthner F, Saha-Moller CR, Fimmel B, Ogi S, Leowanawat P, Schmidt D, Chem. Rev., 116(3), 962 (2016)
Leroy-Lhez S, Baffreau J, Perrin L, Levillain E, Allain M, Blesa MJ, Hudhomme P, J. Org. Chem., 70, 6313 (2005)
Chang JB, Namgoong JW, Kim SH, Park SH, Hwang BH, Kim JP, Dyes Pigment., 121, 30 (2015)
Mishra R, Lim JM, Son M, Panini P, Kim D, Sankar J, Chemistry, 20, 5776 (2014)
Wurthner F, Ahmed S, Thalacker C, Debaerdemaeker T, Chem. Eur. J., 8, 4742 (2002)
Chen H, Peng F, Luo Z, Xu D, Wu ST, Li MC, Lee SL, Tsai WC, Opt. Mater. Express, 4, 2262 (2014)
Ramanan C, Smeigh AL, Anthony JE, Marks TJ, Wasielewski MR, J. Am. Ceram. Soc., 134, 386 (2012)

[1] Tsuda K, Displays, 14, 115 (1993)

[2] Jung J, Park Y, Jaung JY, Park J, Mol. Cryst. Liq. Cryst., 529, 88 (2010)

[3] Lee W, Yuk SB, Choi J, Jung DH, Choi SH, Park J, Kim JP, Dyes Pigment., 92, 942 (2012)

[4] Sabnis RW, Displays, 20, 119 (1999)

[5] Xing Y, Frank WM, David JP, Martin FS, Kyu KJ, Jaehee C, Schubert EF, Jpn. J. Appl. Phys., 48, 120203 (2009)

[6] Bui TS, Kim J, Jung E, Le HS, Nguyen NT, Bae JY, Displays, 34, 192 (2013)

[7] Lee CS, Yoon HJ, Yoon SI, Yoon SH, Kim DW, Jung MS, Won T, Mol. Cryst. Liq. Cryst., 436, 29 (2005)

[8] Lee W, Choi J, Kim SH, Park J, Kim JP, J. Nanosci. Nanotechnol., 15, 295 (2015)

[9] Yuk SB, Lee W, Namgoong JW, Choi J, Chang JB, Kim SH, Kim JY, Kim JP, J. Incl. Phenom. Macrocycl. Chem., 82, 187 (2015)

[10] Chen Z, Baumeister U, Tschierske C, Wurthner F, Chemistry, 13, 450 (2007)

[11] Jiang W, Xiao C, Hao L, Wang Z, Ceymann H, Lambert C, Motta SD, Negri F, Chemistry, 18, 6764 (2012)

[12] Shoer LE, Eaton SW, Margulies EA, Wasielewski MR, J. Phys. Chem. B, 119(24), 7635 (2015)

[13] Choi J, Sakong C, Choi JH, Yoon C, Kim JP, Dyes Pigment., 90, 82 (2011)

[14] Kim JY, Sakong C, Choi SA, Jang H, Kim SH, Chang KS, Han MS, Lee JS, Kim JP, Dyes Pigment., 131, 293 (2016)

[15] Sakong C, Kim YD, Choi JH, Yoon C, Kim JP, Dyes Pigment., 88, 166 (2011)

[16] Flamigni L, Ventura B, Barbieri A, Langhals H, Wetzel F, Fuchs K, Walter A, Chemistry, 16, 13406 (2010)

[17] Chao CC, Leung MK, Su YO, Chiu KY, Lin TH, Shieh SJ, Lin SC, J. Org. Chem., 70, 4323 (2005)

[18] Mamada M, Pe’rez-Boli’var CS, Anzenbacher P, Org. Lett., 13, 4882 (2011)

[19] Wurthner F, Chem. Commun. (Camb), 1564 (2004).

[20] Li M, Xu JR, Zeng Y, Ben HJ, Yao FL, Yang S, Chen EQ, Ren XK, Dyes Pigment., 139, 79 (2017)

[21] Huang C, Barlow S, Marder SR, J. Org. Chem., 76, 2386 (2011)

[22] An ZS, Odom SA, Kelley RF, Huang C, Zhang X, Barlow S, Padilha LA, Fu J, Webster S, Hagan DJ, Van Stryland EW, Wasielewski SMR, Marder SR, J. Phys. Chem. A, 113(19), 5585 (2009)

[23] Choi J, Lee W, Sakong C, Yuk SB, Park JS, Kim JP, Dyes Pigment., 94, 34 (2012)

[24] Yoon C, Kwon HS, Yoo JS, Lee HY, Bae JH, Choi JH, Coloration Technol., 131, 2 (2015)

[25] Wurthner F, Saha-Moller CR, Fimmel B, Ogi S, Leowanawat P, Schmidt D, Chem. Rev., 116(3), 962 (2016)

[26] Leroy-Lhez S, Baffreau J, Perrin L, Levillain E, Allain M, Blesa MJ, Hudhomme P, J. Org. Chem., 70, 6313 (2005)

[27] Chang JB, Namgoong JW, Kim SH, Park SH, Hwang BH, Kim JP, Dyes Pigment., 121, 30 (2015)

[28] Mishra R, Lim JM, Son M, Panini P, Kim D, Sankar J, Chemistry, 20, 5776 (2014)

[29] Wurthner F, Ahmed S, Thalacker C, Debaerdemaeker T, Chem. Eur. J., 8, 4742 (2002)

[30] Chen H, Peng F, Luo Z, Xu D, Wu ST, Li MC, Lee SL, Tsai WC, Opt. Mater. Express, 4, 2262 (2014)

[31] Ramanan C, Smeigh AL, Anthony JE, Marks TJ, Wasielewski MR, J. Am. Ceram. Soc., 134, 386 (2012)