High triplet energy crosslinkable hole transport material for blue phosphorescent organic light-emitting diodes

Sook Hee Jeong; Ho Jin Jang; Jun Yeob Lee

Journal of Industrial and Engineering Chemistry, Vol.78, 324-329, October, 2019

DOI10.1016/j.jiec.2019.05.038 Export Citation

High triplet energy crosslinkable hole transport material for blue phosphorescent organic light-emitting diodes

Sook Hee Jeong, Ho Jin Jang, and Jun Yeob Lee^†

School of Chemical Engineering, Sungkyunkwan University, 2066, Seobu-ro, Jangan-gu, Suwon-si, Gyeonggi-do, 16419, Republic of Korea

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A high triplet energy crosslinkable hole transport material was developed for solution processed blue phosphorescent organic light-emitting diodes. A high triplet energy core structure, 3,3-di(9H-carbazol- 9-yl)biphenyl, was functionalized with a vinylbenzene crosslinking unit to form the crosslinked hole transport layer. Crosslinking of the hole transport layer at 220 °C produced an insoluble film which is stable under exposure to solvents. A blue emitting layer of iridium(III) bis(2-(4,6-difluorophenyl)- pyridinato-N,C2)picolinate doped diphenyldi(4-(9-carbazolyl)phenyl)silane was spin-coated on the crosslinked hole transport layer without damaging the underlying hole transport layer, which afforded solution processed blue phosphorescent organic light-emitting diodes with an external quantum efficiency of 19.1%.

Keywords:Hole transport material;Crosslink;Solution process;Curing;Quantum efficiency

[References]

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[1] Kim H, Byun Y, Das RR, Choi BK, Ahn PS, Appl. Phys. Lett., 91 (2007)

[2] Chen Y, Hao L, Zhang X, Zhang X, Liu M, Zhang M, Wang J, Lai WY, Huang W, J. Appl. Phys., 122, 065304 (2017)

[3] Liu Y, Wei X, Li Z, Liu Z, Wang R, Hu X, Wang P, Yamada-Takamura Y, Qi T, Wang Y, ACS Appl. Energy Mater., 1, 543 (2018)

[4] Albrecht K, Matsuoka K, Fujita K, Yamamoto K, Mater. Chem. Front., 2, 1097 (2018)

[5] Chiba T, Pu YJ, Kido J, Adv. Mater., 27(32), 4681 (2015)

[6] He KD, Liu Y, Gong JY, Zeng P, Kong X, Yang XL, Yang C, Yu Y, Liang RQ, Ou QR, Appl. Surf. Sci., 382, 288 (2016)

[7] Zuniga CA, Barlow S, Marder SR, Chem. Mater., 23, 658 (2011)

[8] Aizawa N, Pu YJ, Watanabe M, Chiba T, Ideta K, Toyota N, Igarashi M, Suzuri Y, Sasabe H, Kido J, Nat. Commun., 5, 5756 (2014)

[9] Earmme T, Jenekhe SA, J. Mater. Chem., 22, 4660 (2012)

[10] Huang F, Cheng YJ, Zhang Y, Liu MS, Jen AKY, J. Mater. Chem., 18, 4495 (2008)

[11] Hung WY, Lin CY, Cheng TL, Yang SW, Chaskar A, Fan GL, Wong KT, Chao TC, Tseng MR, Org. Electron., 13, 2508 (2012)

[12] Aizawa N, Pu YJ, Chiba T, Kawata S, Sasabe H, Kido J, Adv. Mater., 26(45), 7543 (2014)

[13] Niu YH, Liu MS, Ka JW, Bardeker J, Zin MT, Schofield R, Chi Y, Jen AKY, Adv. Mater., 19(2), 300 (2007)

[14] Jou JH, Li TH, Kumar S, An CC, Agrawal A, Chen SZ, Fang PH, Krucaite G, Grigalevicius S, Grazulevicius J, Sung CF, Org. Electron., 24, 254 (2015)

[15] Jiang W, Ban X, Ye M, Sun Y, Duan L, Qiu Y, J. Mater. Chem. C, 3, 243 (2015)

[16] Tsai KW, Hung MK, Mao YH, Chen SA, Adv. Funct. Mater., 1901025 (2019).

[17] Liaptsis G, Meerholz K, Adv. Funct. Mater., 23(3), 359 (2013)

[18] Niu YH, Liu M, Cheng YJ, Ka JW, Bardeker J, Jen AKY, Presented at SID Symposium Digest of Technical Papers, 37, pp931 (2006).

[19] Seo JA, Jeon SK, Gong MS, Lee JY, Noh CH, Kim SH, J. Mater. Chem. C, 3, 4640 (2015)

[20] Kang YJ, Han SH, Lee JY, J. Ind. Eng. Chem., 62, 258 (2018)

[21] Bagnich SA, Rudnick A, Schroegel P, Strohriegl P, Kohler A, Philos. Trans. Royal Soc. A, 373 (2015).

[22] Song S, Kim TK, Lee JY, Lee YK, Jeong HI, J. Ind. Eng. Chem., 68, 350 (2018)

[23] Im Y, Han SH, Lee JY, J. Ind. Eng. Chem., 66, 381 (2018)

[24] Oh CS, Lee JY, Noh CH, Kim SH, J. Mater. Chem. C, 4, 3792 (2016)