High electroluminescence efficiency and long device lifetime of a fluorescent green-light emitter using aggregation-induced emission

Hyocheol Jung; Hwangyu Shin; Siin Kim; Joonghan Kim; Byeong-Kwan An; Ji-Hoon Lee; Hyotcherl Ihee; Jongwook Park

Journal of Industrial and Engineering Chemistry, Vol.87, 213-221, July, 2020

DOI10.1016/j.jiec.2020.04.003 Export Citation

High electroluminescence efficiency and long device lifetime of a fluorescent green-light emitter using aggregation-induced emission

Hyocheol Jung^{1, 2}, Hwangyu Shin³, Siin Kim^{4, 5}, Joonghan Kim³, Byeong-Kwan An³, Ji-Hoon Lee¹, Hyotcherl Ihee^{4, 5}, and Jongwook Park^{2, †}

¹Department of Polymer Science and Engineering, Korea National University of Transportation, 50 Daehak-ro, Chungju-si, Chungbuk 27909, Republic of Korea
²Department of Chemical Engineering, Kyung Hee University, Gyeonggi-do 17104, Republic of Korea
³Department of Chemistry, Catholic University of Korea, Bucheon 14662, Republic of Korea
⁴Department of Chemistry and KI for the BioCentury, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea
⁵Center for Nanomaterials and Chemical Reactions, Institute for Basic Science (IBS), Daejeon 34141, Republic of Korea

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Three bipolar materials, 4-(4,6-diphenyl-1,3,5-triazin-2-yl)-N,N-diphenylaniline (DPAT-Ph), 4-(4, 6-diphenyl-1,3,5-triazin-2-yl)-N,N-diphenylnaphthalen-1-amine (DPAT-Na), and 10-(4,6-diphenyl- 1,3,5-triazin-2-yl)-N,N-diphenylanthracen-9-amine (DPAT-An), were designed and synthesized. To achieve a bipolar character, diphenylamine (DPA) moiety and 2,4-diphenyl-1,3,5-triazine (DPT) moiety were introduced as electron donating and electron accepting groups, respectively. The three compounds exhibited UV maximum wavelengths (UVmax) at 395.454 nm and photoluminescence maximum wavelengths (PLmax) at 472.546 nm. 10-(4,6-Diphenyl-1,3,5-triazin-2-yl)-N,N-diphenylanthracen-9- amine (DPAT-An) shows AIE phenomenon even though DPAT-An does not have tetraphenylethylene (TPE) moiety which is representative AIE structure. DPAT-An exhibits over EQE value of 5% and long device lifetime of 1310 h without sublimation process.

Keywords:Organic light-emitting diodes;Fluorescence;Green emitter;Aggregation-induced emission;Luminance efficiency;Device lifetime

[References]

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Baek NS, Hau SK, Yip HL, Acton O, Chen KS, Jen AKY, Chem. Mater., 20, 5734 (2008)
Kang I, Hong JA, Kim R, Jang JW, Hwang J, Kim JH, Kwon SK, Kim YH, Macromol. Res., 21(4), 450 (2013)
Tang CW, Van Slyke SA, Chen CH, J. Appl. Phys., 65, 3610 (1989)
Baldo MA, Thompson ME, Forrest SR, Nature, 403, 750 (2000)
Wu CC, Lin YT, Wong KT, Chen RT, Chien YY, Adv. Mater., 16(1), 61 (2004)
Adachi C, Tsutsui T, Saito S, Appl. Phys. Lett., 55, 1489 (1989)
Kim SK, Park YI, Kang IN, Park JW, J. Mater. Chem., 17, 4670 (2007)
Kim SK, Yang B, Ma Y, Lee JH, Park JW, J. Mater. Chem., 18, 3376 (2008)
Kim B, Park Y, Lee J, Yokoyama D, Lee JH, Kido J, Park J, J. Mater. Chem. C, 1, 432 (2013)
Luo J, Xie Z, Lam JWY, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ, Chem. Commun., 1740 (2001).
Mei J, Leung NLC, Kwok RTK, Lam JWY, Tang BZ, Chem. Rev., 115(21), 11718 (2015)
Dong Y, Lam JWY, Qiu A, Sun J, Liu J, Li Z, Zhang S, Sun J, Kwok HS, Tang BZ, Appl. Phys. Lett., 91, 011111 (2007)
Zhao Z, Chen S, Lam JWY, Lu P, Zhong Y, Wong KS, Kwok HS, Tang BZ, Chem. Commun., 46, 2221 (2010)
Zhao Z, Lu P, Lam JWY, Wang Z, Chan CYK, Sung HHY, Williams ID, Ma Y, Tang BZ, Chem. Sci., 2, 672 (2011)
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Benor A, Takizawa SY, Bolivar CP, Anzenbacher P, Appl. Phys. Lett., 96, 243310 (2010)
Lee S, Kim KH, Limbach D, Park YS, Kim JJ, Adv. Funct. Mater., 23, 4105 (2013)
Gong SL, Chen YH, Luo JJ, Yang CL, Zhong C, Qin JG, Ma DG, Adv. Funct. Mater., 21(6), 1168 (2011)
Huang JH, Su JH, Li X, Lam MK, Fung KM, Fan HH, Cheah KW, Chen CH, Tian HJ, J. Mater. Chem., 21, 2957 (2011)
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Chen M, Nie H, Song B, Li L, Sun JZ, Qin A, Tang BZ, J. Mater. Chem. C, 4, 2901 (2016)
Masiak P, Wierzbowska M, J. Mater. Sci., 52(8), 4378 (2017)
Costa JCS, Taveira RJS, Lima CFRAC, Mendes A, Santos LMNBF, Opt. Mater., 58, 51 (2016)
Park Y, Kim B, Lee C, Hyun A, Jang S, Lee JH, Gal YS, Kim TH, Kim KS, Park J, J. Phys. Chem. C, 115, 4843 (2011)
Parker CA, Joyce TA, Chem. Commun., 6, 744 (1967)
Yokoyama D, Park Y, Kim B, Kim S, Pu YJ, Kido J, Park, Appl. Phys. Lett., 99, 123303 (2011)
Kang S, Jung H, Lee H, Park S, Kim J, Park J, J. Mater. Chem. C, 7, 14709 (2019)
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Liu W, Ying S, Zhang Q, Ye S, Guo R, Ma D, Wang L, Dyes Pigment., 158, 204 (2018)

[1] Tang CW, Van Slyke SA, Appl. Phys. Lett., 51, 913 (1987)

[2] Baek NS, Hau SK, Yip HL, Acton O, Chen KS, Jen AKY, Chem. Mater., 20, 5734 (2008)

[3] Kang I, Hong JA, Kim R, Jang JW, Hwang J, Kim JH, Kwon SK, Kim YH, Macromol. Res., 21(4), 450 (2013)

[4] Tang CW, Van Slyke SA, Chen CH, J. Appl. Phys., 65, 3610 (1989)

[5] Baldo MA, Thompson ME, Forrest SR, Nature, 403, 750 (2000)

[6] Wu CC, Lin YT, Wong KT, Chen RT, Chien YY, Adv. Mater., 16(1), 61 (2004)

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

[8] Kim SK, Park YI, Kang IN, Park JW, J. Mater. Chem., 17, 4670 (2007)

[9] Kim SK, Yang B, Ma Y, Lee JH, Park JW, J. Mater. Chem., 18, 3376 (2008)

[10] Kim B, Park Y, Lee J, Yokoyama D, Lee JH, Kido J, Park J, J. Mater. Chem. C, 1, 432 (2013)

[11] Luo J, Xie Z, Lam JWY, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ, Chem. Commun., 1740 (2001).

[12] Mei J, Leung NLC, Kwok RTK, Lam JWY, Tang BZ, Chem. Rev., 115(21), 11718 (2015)

[13] Dong Y, Lam JWY, Qiu A, Sun J, Liu J, Li Z, Zhang S, Sun J, Kwok HS, Tang BZ, Appl. Phys. Lett., 91, 011111 (2007)

[14] Zhao Z, Chen S, Lam JWY, Lu P, Zhong Y, Wong KS, Kwok HS, Tang BZ, Chem. Commun., 46, 2221 (2010)

[15] Zhao Z, Lu P, Lam JWY, Wang Z, Chan CYK, Sung HHY, Williams ID, Ma Y, Tang BZ, Chem. Sci., 2, 672 (2011)

[16] Zhao Z, Chen S, Lam JWY, Wang Z, Lu P, Faisal M, Sung HHY, Williams ID, Ma Y, Kwok HS, Tang BZ, J. Mater. Chem., 21, 7210 (2011)

[17] Zhao Z, Chen S, Chan CYK, Lam JWY, Jim CKW, Lu P, Chang Z, Kwok HS, Qiu H, Tang BZ, Chem. Asian J., 7, 484 (2012)

[18] Chang Z, Jiang Y, He B, Chen J, Yang Z, Lu P, Kwok HS, Zhao Z, Qiu H, Tang BZ, Chem. Commun., 49, 594 (2013)

[19] Chang CH, Kuo MC, Lin WC, Chen YT, Wong KT, Chou SH, Mondal E, Kwong RC, Xia S, Nakagawa T, Adachi C, J. Mater. Chem., 22, 3832 (2012)

[20] Benor A, Takizawa SY, Bolivar CP, Anzenbacher P, Appl. Phys. Lett., 96, 243310 (2010)

[21] Lee S, Kim KH, Limbach D, Park YS, Kim JJ, Adv. Funct. Mater., 23, 4105 (2013)

[22] Gong SL, Chen YH, Luo JJ, Yang CL, Zhong C, Qin JG, Ma DG, Adv. Funct. Mater., 21(6), 1168 (2011)

[23] Huang JH, Su JH, Li X, Lam MK, Fung KM, Fan HH, Cheah KW, Chen CH, Tian HJ, J. Mater. Chem., 21, 2957 (2011)

[24] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al., Gaussian 09 Revision D.1, Gaussian, Inc., Wallingford, CT, 2009.

[25] Chen M, Nie H, Song B, Li L, Sun JZ, Qin A, Tang BZ, J. Mater. Chem. C, 4, 2901 (2016)

[26] Masiak P, Wierzbowska M, J. Mater. Sci., 52(8), 4378 (2017)

[27] Costa JCS, Taveira RJS, Lima CFRAC, Mendes A, Santos LMNBF, Opt. Mater., 58, 51 (2016)

[28] Park Y, Kim B, Lee C, Hyun A, Jang S, Lee JH, Gal YS, Kim TH, Kim KS, Park J, J. Phys. Chem. C, 115, 4843 (2011)

[29] Parker CA, Joyce TA, Chem. Commun., 6, 744 (1967)

[30] Yokoyama D, Park Y, Kim B, Kim S, Pu YJ, Kido J, Park, Appl. Phys. Lett., 99, 123303 (2011)

[31] Kang S, Jung H, Lee H, Park S, Kim J, Park J, J. Mater. Chem. C, 7, 14709 (2019)

[32] Kim SK, Yang B, Park YI, Ma Y, Lee JY, Kim HJ, Park J, Org. Electron., 10, 822 (2009)

[33] Liu W, Ying S, Zhang Q, Ye S, Guo R, Ma D, Wang L, Dyes Pigment., 158, 204 (2018)