C1,C8-modified carbazole-based bipolar host materials for blue phosphorescent electroluminescent devices

Rajendra Kumar Konidena; Junseop Lim; Jun Yeob Lee

Journal of Industrial and Engineering Chemistry, Vol.107, 75-80, March, 2022

DOI10.1016/j.jiec.2021.11.025 Export Citation

C1,C8-modified carbazole-based bipolar host materials for blue phosphorescent electroluminescent devices

Rajendra Kumar Konidena, Junseop Lim, and Jun Yeob Lee^†

School of Chemical Engineering, Sungkyunkwan University, 2066 Seobu-ro, Jangan-gu, Suwon, Gyeonggi 440-746, Republic of Korea

E-mail:

Herein, we report a new molecular design based on carbazole for the development of high triplet energy bipolar host materials for blue phosphorescent organic light emitting diodes (PhOLEDs). Two new isomeric host materials named, 11CzCzCN and 14CzCzCN were designed and synthesized by modifying the carbazole core with carbazole donor at C1 and cyano acceptor at C8-position. The effective interchromophoric electronic communications between the attached donors and central carbazole were interrupted by virtue of large dihedral angle at C1 and short-axis linkage. Also, the strong charge transfer interactions between the donor at C1 and acceptor at C8 was hampered due to the broken conjugation. As a result, the compounds showed high triplet energy (ET) over 2.75 eV without compromising the bipolar charge transporting property. Interestingly, computations and single carrier device analysis evidenced good bipolar charge transporting ability for 11CzCzCN over its structural isomer 14CzCzCN. The applicability of these compounds as hosts for blue PhOLEDs was explored by using a well-known Flrpic dopant. The 11CzCzCN hosted device showed higher performance with maximum EQE of 20.6%, current efficiency of 39.6 cd/A and efficiency roll off of 8.2% at 1000 cd/m2 over its analogue 14CzCzCN hosted device attributed to its high ET and balanced charge transporting property. We believe that this study would provide valuable insights for executing new molecular designs on carbazole for the development of efficient host materials for blue PhOLEDs.

Keywords:Blue device;Phosphorescence;Host;Triplet energy;Efficiency

[References]

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Lee CH, Tang MC, Kong FKW, Cheung WL, Ng M, Chan MY, Yam VWW, J. Am. Chem. Soc., 142, 520 (2020)
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Wang Y, Yun JH, Wang L, Lee JY, Adv. Funct. Mater., 31, 2008332 (2021)
Yook KS, Lee JY, Chem. Rec., 16, 159 (2016)
Zhu XD, Zhang YL, Yuan Y, Zheng Q, Yu Y, Li Y, Jiang ZQ, Liao LS, J. Mater. Chem. C, 7, 6714 (2019)
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Cui LS, Kim JK, Nomura H, Nakanotani H, Adachi C, Angew. Chem.-Int. Edit., 55, 6864 (2016)
Song W, Shi L, Gao L, Hu P, Mu H, Xia X, Huang J, Su SJ, ACS Appl. Mater. Interfaces, 10, 5714 (2018)
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Cui LS, Kim JK, Nomura H, Nakanotani H, Adachi C, Angew. Chem.-Int. Edit., 55, 6864 (2016)
Song W, Shi F, Gao L, Hu P, Mu H, Xia X, Huang J, Su SJ, ACS Appl. Mater. Interfaces, 10, 5714 (2018)
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Jeon SK, Lee HL, Yook KS, Lee JY, Adv. Mater., 31, 1803524 (2019)
Byeon SY, Lee DR, Yook KS, Lee JY, Adv. Mater., 31, 1803714 (2019)
Yang W, Zhang Z, Han C, Zhang Z, Xu H, Yan P, Zhao Y, Liu S, Chem. Commun., 49, 2822 (2013)
Huang H, Wang Y, Pan B, Yang X, Wang L, Chen J, Ma D, Yang C, Chem.-Eur. J., 19, 1828 (2013)
Ameen S, Lee SB, Yoon SC, Lee J, Lee C, Dyes Pigment., 124, 35 (2016)
Konidena RK, Thomas KRJ, Pathak A, Dubey DK, Sahoo S, Jou JH, ACS Appl. Mater. Interfaces, 10, 24013 (2018)
Kotchapradist P, Prachumrak N, Tarsang R, Jungsuttiwong S, Keawin T, Sudyoadsuk T, Promarak V, J. Mater. Chem. C, 1, 4916 (2013)
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[1] Baldo MA, O'Brien DF, You Y, Shoustikov A, Sibley S, Thompson ME, Forrest SR, Nature, 35, 151 (1998)

[2] Adachi C, Baldo MA, Forrest SR, Appl. Phys. Lett., 77, 904 (2000)

[3] Ma D, Tsuboi T, Qiu Y, Duan L, Adv. Mater., 29, 1603253 (2017)

[4] Yang X, Zhou G, Wong WY, Chem. Soc. Rev., 44, 8484 (2015)

[5] Maheshwaran A, Sree VG, Park HY, Kim H, Han SH, Lee JY, Jin SH, Adv. Funct. Mater., 28, 1802945 (2018)

[6] Zhu ZQ, Park CD, Klimes K, Li J, Adv. Opt. Mater., 7, 1801518 (2019)

[7] Shin H, Lee JH, Moon CK, Huh JS, Sim B, Kim JJ, Adv. Mater., 28, 4920 (2016)

[8] Lee CH, Tang MC, Kong FKW, Cheung WL, Ng M, Chan MY, Yam VWW, J. Am. Chem. Soc., 142, 520 (2020)

[9] Tao Y, Yang C, Qin J, Chem. Soc. Rev., 40, 2943 (2011)

[10] Chaskar A, Chen HF, Wong KT, Adv. Mater., 23, 3876 (2011)

[11] Sasabe H, Kido J, Eur. J. Org. Chem., 2013, 7653 (2013)

[12] Pal AK, Krotkus S, Fontani M, Mackenzie CFR, Cordes DB, Slawin AM, Samuel DWF EZ, Colman, Adv. Mater., 30, 1804231 (2018)

[13] Wang Y, Yun JH, Wang L, Lee JY, Adv. Funct. Mater., 31, 2008332 (2021)

[14] Yook KS, Lee JY, Chem. Rec., 16, 159 (2016)

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

[16] Lucas F, Quinton C, Fall S, Heiser T, Tondelier D, Geffroy B, Leclerc N, Berthelot JR, Poriel C, J. Mater. Chem. C, 8, 16354 (2020)

[17] Kim GH, Lampande R, Park MJ, Bae HW, Kong JH, Kwon JH, Park JW, Park YW, Song CE, J. Phys. Chem. C, 118, 28757 (2014)

[18] Chen WC, Yuan Y, Zhu ZL, Jiang ZQ, Su SJ, Liao LS, Lee CS, Chem. Sci., 9, 4062 (2018)

[19] Wang F, Liu D, Li J, Ma M, ACS Appl. Mater. Interfaces, 9, 37888 (2017)

[20] Jeon SO, Lee KH, Kim JS, Ihn SG, Chung YS, Kim JW, Lee H, Kim SH, Choi H, Lee JY, Nat. Photon., 15, 208 (2021)

[21] Chang SY, Li GT, Cheng YC, Hunag JJ, Chang CL, Lin CF, Lee JH, Chiu TL, Leung MK, ACS Appl. Mater. Interfaces, 10, 42723 (2018)

[22] Konidena RK, Lee KH, Lee JY, Chem. Commun., 55, 8178 (2019)

[23] Cui LS, Kim JK, Nomura H, Nakanotani H, Adachi C, Angew. Chem.-Int. Edit., 55, 6864 (2016)

[24] Wang Q, Wu Z, Zhao Y, Chen J, Ma D, Org. Electron., 32, 21 (2016)

[25] Macionis S, Gudeika D, Volyniuk D, Bezvikonnyi O, Andruleviciene V, Lee JH, Fan B, Chen CH, Lin BY, Chiu TL, Grazulevicius JV, Adv. Opt. Mater., 9, 2002227 (2021)

[26] Cui LS, Kim JK, Nomura H, Nakanotani H, Adachi C, Angew. Chem.-Int. Edit., 55, 6864 (2016)

[27] Song W, Shi L, Gao L, Hu P, Mu H, Xia X, Huang J, Su SJ, ACS Appl. Mater. Interfaces, 10, 5714 (2018)

[28] Macionis S, Gudeika D, Volyniuk D, Bezvikonnyi O, Andruleviciene V, Lee JH, Fan B, Chen CH, Lin BY, Chiu TL, Grazulevicius JV, Adv. Opt. Mater., 9, 2002227 (2021)

[29] Cui LS, Kim JK, Nomura H, Nakanotani H, Adachi C, Angew. Chem.-Int. Edit., 55, 6864 (2016)

[30] Song W, Shi F, Gao L, Hu P, Mu H, Xia X, Huang J, Su SJ, ACS Appl. Mater. Interfaces, 10, 5714 (2018)

[31] Li D, Li J, Liu D, Li W, Ko CL, Hung WY, Duan C, ACS Appl. Mater. Interfaces, 13, 13459 (2021)

[32] Ko SB, Kang S, Kim T, Chem.-Eur. J., 26, 7767 (2020)

[33] Li D, Liu D, Li J, Dong R, Liu B, Wie Q,, Mater. Chem. Front., 5, 2867 (2021)

[34] Liu B, Zhao J, Luo C, Lu F, Tao S, Tong QX, J. Mater. Chem. C, 4, 2003 (2016)

[35] Li G, Zheng Z, Klimes K, Zhu ZQ, Qu J, Zhu H, Li J, ACS Appl. Mater. Interfaces, 11, 40320 (2019)

[36] Wex B, Kaafarani BR, J. Mater. Chem. C, 5, 8622 (2017)

[37] Yang Z, Mao Z, Xie Z, Zhang Y, Liu S, Zhao J, Xu J, Chi Z, Aldred MP, Chem. Soc. Rev., 46, 915 (2017)

[38] Jeon SK, Lee HL, Yook KS, Lee JY, Adv. Mater., 31, 1803524 (2019)

[39] Byeon SY, Lee DR, Yook KS, Lee JY, Adv. Mater., 31, 1803714 (2019)

[40] Yang W, Zhang Z, Han C, Zhang Z, Xu H, Yan P, Zhao Y, Liu S, Chem. Commun., 49, 2822 (2013)

[41] Huang H, Wang Y, Pan B, Yang X, Wang L, Chen J, Ma D, Yang C, Chem.-Eur. J., 19, 1828 (2013)

[42] Ameen S, Lee SB, Yoon SC, Lee J, Lee C, Dyes Pigment., 124, 35 (2016)

[43] Konidena RK, Thomas KRJ, Pathak A, Dubey DK, Sahoo S, Jou JH, ACS Appl. Mater. Interfaces, 10, 24013 (2018)

[44] Kotchapradist P, Prachumrak N, Tarsang R, Jungsuttiwong S, Keawin T, Sudyoadsuk T, Promarak V, J. Mater. Chem. C, 1, 4916 (2013)

[45] Frisch MJ et al., Gaussian 09, revision A.02; Gaussian Inc. Wallingford, CT, 2009.

[46] Konidena RK, Lee KH, Lee JY, Chem. Asian. J., 14, 313 (2019)