Non-symmetric 9,10-Di(2-naphthyl)anthracene derivatives as hosts and emitters for solution-processed blue fluorescent organic light emitting diodes

Hyein Ha; Jinhwi Cho; Ja Yeon Lee; Buyong Yun; Jihoon Lee; Min Chul Suh

Journal of Industrial and Engineering Chemistry, Vol.87, 90-99, July, 2020

DOI10.1016/j.jiec.2020.03.016 Export Citation

Non-symmetric 9,10-Di(2-naphthyl)anthracene derivatives as hosts and emitters for solution-processed blue fluorescent organic light emitting diodes

Hyein Ha, Jinhwi Cho¹, Ja Yeon Lee, Buyong Yun¹, Jihoon Lee^{1, †}, and Min Chul Suh^†

Dept. of Information Display, Kyung Hee University, Dongdaemoon-Gu, Seoul, 02447, Republic of Korea
¹Dept. of Polymer Science and Engineering and Dept. of IT Convergence (BK21 PLUS), Korea National University of Transportation, Chungju, 27469, Republic of Korea

E-mail:,

A series of new asymmetric anthracene derivatives have been successfully synthesized for use in the light emitting layer of solution processed blue fluorescent organic light emitting diodes (OLEDs), which could be used both as host and dopant. Especially, new synthetic blue fluorescent materials with anthracene moieties without any alkyl chains showed high solubility in common organic solvents probably due to their severely twisted internal structures. They also show moderately high thermal stability due to their rigid internal core units. With those novel soluble blue fluorescent materials, we created moderately efficient solution-processed fluorescent OLEDs. And a new anthracene derivative [9-(9,10-di(naphthalen- 2-yl)anthracen-2-yl)-9H-carbazole (DN-2-CzA)] as a host material exhibited moderately high efficiency and external quantum efficiency of up to 3.2 cd/A and 1.6%, respectively, when we utilized 4,40-bis[4-(diphenylamino)styryl]biphenyl as a dopant. Meanwhile, the [N-(naphthalen-1-yl)-9,10-di(naphthalen-2-yl)-N-phenylanthra-cen-2-amine (DN-2-NPAA)] as a dopant material showed pretty good device performance, up to 5.2 cd/A and 2.2% (EQE), when we utilized 2-tert-butyl-9,10-di(naphth-2-yl) anthracene as a host.

Keywords:Solution-Processed OLEDs;Highly efficient blue fluorescent materials;New synthetic anthracene based materials;Host materials;Dopant materials

[References]

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Sasabe H, Kido J, Chem. Mater., 23, 621 (2011)
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Wen SW, Lee MT, Chen CH, J. Disp. Technol., 1, 90 (2005)
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Komatsu R, Sasabe H, Seino Y, Nakao K, Kido J, J. Mater. Chem. C, 4, 2274 (2016)
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[1] Tang CW, VanSlyke SA, Appl. Phys. Lett., 51, 913 (1987)

[2] Adachi C, Nagai K, Tamoto N, Appl. Phys. Lett., 66, 2679 (1995)

[3] Adachi C, Tsutsui T, Saito S, Appl. Phys. Lett., 55, 1489 (1989)

[4] Park SR, Kim SM, Choi Y, Lee JY, Lee JH, Suh MC, Dyes Pigment., 170, 107621 (2019)

[5] Sasabe H, Kido J, Chem. Mater., 23, 621 (2011)

[6] Seo J, Park SR, Kim M, Suh MC, Lee JH, Dyes Pigment., 162, 959 (2019)

[7] Wen SW, Lee MT, Chen CH, J. Disp. Technol., 1, 90 (2005)

[8] Laaperi A, J. SID, 16/11, 1125 (2008)

[9] Komatsu R, Sasabe H, Seino Y, Nakao K, Kido J, J. Mater. Chem. C, 4, 2274 (2016)

[10] Kang JS, Hong TR, Kim HJ, Son YH, Lampande R, Kang BY, Lee C, Bin JK, LEe BS, Yang JH, Kim JW, Park S, Cho MJ, Kwon JH, Choi DH, J. Mater. Chem. C, 4, 4512 (2016)

[11] Bui TT, Goubard F, Ouali MI, Gigmes D, Dumur F, Beilstein J. Org. Chem., 14, 282 (2018)

[12] Su SJ, Sasabe H, Takeda T, Kido J, Chem. Mater., 20, 1691 (2008)

[13] Sicard LJ, Lee HC, Wang Q, Liu XY, Jeannin O, Rault-Berhelot J, Liao LS, Jianag ZQ, Poriel C, Angew. Chem.-Int. Edit., 58, 3848 (2019)

[14] Zhu XD, Zhang YL, Yuan Y, Zheng Q, Yu YJ, Li Y, Jiang ZQ, Liao LS, J. Mater. Chem. C, 7, 6714 (2019)

[15] Quinton C, Thiery S, Jeannin O, Tondlier D, Gefferoy B, Jacques E, Ralult-Berthelot J, Poriel C, ACS Appl. Mater. Interfaces, 9, 6194 (2017)

[16] Shiu YJ, Cheng YC, Tsai WL, Wu CC, Chao CT, Lu CW, Chi Y, Chen YT, Liu SH, Chou RT, Angew. Chem.-Int. Edit., 55, 3017 (2016)

[17] Kang I, Back JY, Kim R, Kim YH, Kwon SK, Dyes Pigment., 92, 588 (2012)

[18] Zhang Z, Jiang W, Ban X, Yang M, Ye S, Huang B, Sun Y, RSC Adv., 5, 29708 (2015)

[19] Zheng CJ, Zhao WM, Wang ZQ, Huang D, Ye J, Ou XM, Zhang XH, Lee CS, Lee ST, J. Mater. Chem., 20, 1560 (2010)

[20] Tao S, Zhou Y, Lee CS, Lee ST, Huang D, Zhang X, J. Phys. Chem. C, 112, 14603 (2008)

[21] Zhu M, Ye T, Ge C, Li, Cao X, Zhong C, Ma D, Qin J, Yang C, J. Phys. Chem. C, 115, 19965 (2011)

[22] Shin HY, Suh MC, Org. Electron., 15, 2932 (2014)

[23] Suh MC, Jiang B, Tilley TD, Angew. Chem.-Int. Edit., 39, 2870 (2000)

[24] Johnson SA, Liu FQ, Suh MC, Zurcher S, Haufe M, Mao SSH, Tilley TD, J. Am. Chem. Soc., 125(14), 4199 (2003)

[25] Suh MC, Chin BD, Kim MH, Kang TM, Lee ST, Adv. Mater., 15(15), 1254 (2003)

[26] Lee JW, Park YW, Leeand SH, Yeo SW, Kr. Pat., No.1020160116219 (2016).

[27] Park SR, Kang JH, Ahn DA, Suh MC, J. Mater. Chem. C, 6, 7750 (2018)

[28] Tauc J, Grigorovici R, Vancu A, Phys. Status Solidi, 15, 627 (1966)

[29] Fujii A, Ootake R, Fujisawa T, Ozaki M, Ohmori Y, Lada T, Yoshino K, Lu HT, Chan HSO, Ng SC, Appl. Phys. Lett., 77, 660 (2000)

[30] Porres L, Holland A, Monkman A, Kemp C, Beeby A, Lars-Olof P, J. Fluorescence, 16, 267 (2006)

[31] The Royal Society of Chemistry, De Mello Method for the Calculation of the Absolute Quantum Efficiency of a Compound, Supplementary Material (ESI) for Chemical Communications, (2009).