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Novel phenanthro[9,10-d]imidazole-zinc complex as a host for high-performance OLEDs

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Abstract

In this work, a novel phenanthro[9,10-d]imidazole-zinc coordination complex (Zn(TPPI)2) is reported. This compound exhibits suitable physical properties for a host material. First, its highest occupied molecular orbital (HOMO) (− 5.33 eV) energy level is favorable for hole injection from transporting layer. Second, its small singlet–triplet splitting (0.31 eV) can reduce the intrinsic energy loss from singlet to triplet excited state and promote the device efficiency. Finally, its good thermal stability (decomposition temperature: 495 °C) favors evaporation preparation of uniform films. As a result, yellow–red and red phosphorescent devices which utilize Zn(TPPI)2 as host display high efficiencies (yellow–red: 58.35 cd/A, 70.52 lm/W, 20.82%) (red: 15.89 cd/A, 16.09 lm/W and 19.05%). The performance of red device is comparable to the best results of previous publications on corresponding emitter. Meanwhile, the undoped device of Zn(TPPI)2 exhibits high efficiencies (3.79 cd/A, 3.97 lm/W, 2.47%) in zinc-complex blue emitters. These results demonstrate that Zn(TPPI)2 is a good blue emitter and host material.

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References

  1. H. Na, T.S. Teets, Highly luminescent cyclometalated iridium complexes generated by nucleophilic addition to coordinated isocyanides. J. Am. Chem. Soc. 140(20), 6353–6360 (2018)

    Article  CAS  Google Scholar 

  2. T. Fleetham, Y.L. Ji, L. Huang, T.S. Fleetham, J. Li, Efficient and stable single-doped white OLEDs using a palladium-based phosphorescent excimer. Chem. Sci. 8(12), 7983–7990 (2017)

    Article  CAS  Google Scholar 

  3. N. Su, G.Z. Lu, Y.X. Zheng, Highly efficient green electroluminescence of iridium(III) complexes based on (1H-pyrazol-5-yl)pyridine derivatives ancillary ligands with low efficiency roll-off. J. Mater. Chem. C 6(21), 5778–5784 (2018)

    Article  CAS  Google Scholar 

  4. X.L. Yang, B. Jiao, J.S. Dang, Y.H. Sun, Y. Wu, G.J. Zhou, W.Y. Wong, Achieving high-performance solution-processed orange OLEDs with the phosphorescent cyclometalated trinuclear Pt(II) complex. ACS Appl. Mater. Interfaces 10(12), 10227–10235 (2018)

    Article  CAS  Google Scholar 

  5. J. Zhao, Z. Feng, D. Zhong, X. Yang, Y. Wu, G. Zhou, Z. Wu, Cyclometalated platinum complexes with aggregation-induced phosphorescence emission behavior and highly efficient electroluminescent ability. Chem. Mater. 30(3), 929–946 (2018)

    Article  CAS  Google Scholar 

  6. Y.Q. Miao, P. Tao, L. Gao, X.L. Li, L.W. Wei, S.J. Liu, H. Wang, B.S. Xu, Q. Zhao, Highly efficient chlorine functionalized blue iridium(III) phosphors for blue and white phosphorescent organic light-emitting diodes with the external quantum efficiency exceeding 20%. J. Mater. Chem. C 6(25), 6656–6665 (2018)

    Article  CAS  Google Scholar 

  7. Z.W. Liu, J. Qiu, F. Wei, J.Q. Wang, X.C. Liu, M.G. Helander, S. Rodney, Z.B. Wang, Z.Q. Bian, Z.H. Lu, M.E. Thompson, C.H. Huang, Simple and high efficiency phosphorescence organic light-emitting diodes with codeposited copper(I) emitter. Chem. Mater. 26, 2368–2373 (2014)

    Article  CAS  Google Scholar 

  8. K.Y. Hwang, M.H. Lee, H. Jang, Y. Sung, J.S. Lee, S.H. Kim, Y. Do, Aluminium-salen luminophores as new hole-blocking materials for phosphorescent OLEDs. Dalton Trans. 14(14), 1818–1820 (2008)

    Article  CAS  Google Scholar 

  9. P. Kathirgamanathan, S. Surendrakumar, J. Antipan-Lara, S. Ravichandran, Y.F. Chan, V. Arkley, S. Ganeshamurugan, M. Kumaraverl, G. Paramswara, A. Partheepan, V.R. Reddy, D. Bailey, A.J. Blake, Novel lithium Schiff-base cluster complexes as electron injectors: synthesis, crystal structure, thin film characterisation and their performance in OLEDs. J. Mater. Chem. 22(13), 6104–6116 (2012)

    Article  CAS  Google Scholar 

  10. A.S. Burlov, V.G. Vlasenko, A.V. Dmitriev, V.V. Chesnokov, A.I. Uraev, D.A. Garnovskii, Y.V. Zubavichus, A.L. Trigub, I.S. Vasilchenko, D.A. Lypenko, E.I. Mal’tsev, T.V. Lifintseva, G.S. Borodkin, Synthesis, structure, photo- and electroluminescent properties of zinc(II) complexes with aminomethylene derivatives of 1-phenyl-3-methyl-4-formylpyrazol-5-one and 3-and 6-aminoquinolines. Synthetic Met. 203, 156–163 (2015)

    Article  CAS  Google Scholar 

  11. Y.G. Li, X. Gao, L. Wang, G.L. Tu, Deep-red organic light-emitting diodes with stable electroluminescent spectra based on zinc complex host material. RSC Adv. 7(64), 40533–40538 (2017)

    Article  CAS  Google Scholar 

  12. M.E. Burin, V.A. Ilichev, A.P. Pushkarev, D.L. Vorozhtsov, S.Y. Ketkov, G.K. Fukin, M.A. Lopatin, A.A. Nekrasov, M.N. Bochkarev, Synthesis and luminescence properties of lithium, zinc and scandium 1-(2-pyridyl)naphtholates. Org. Electron. 13(12), 3203–3210 (2012)

    Article  CAS  Google Scholar 

  13. G. Cheng, G.K.M. So, W.P. To, Y. Chen, C.C. Kwok, C.S. Ma, X.G. Guan, X. Chang, W.M. Kwok, C.M. Che, Luminescent zinc(II) and copper(I) complexes for high-performance solution-processed monochromic and white organic light-emitting devices. Chem. Sci. 6(8), 4623–4635 (2015)

    Article  CAS  Google Scholar 

  14. Q.C. Zhang, H. Xiao, X. Zhang, L.J. Xu, Z.N. Chen, Luminescent oligonuclear metal complexes and the use in organic light-emitting diodes. Coordin. Chem. Rev. 378, 121–133 (2019)

    Article  CAS  Google Scholar 

  15. J. Zhao, F.F. Dang, B. Liu, Y. Wu, X.L. Yang, G.J. Zhou, Z.X. Wu, W.Y. Wong, Bis-Zn-II salphen complexes bearing pyridyl functionalized ligands for efficient organic light-emitting diodes (OLEDs). Dalton Trans. 46(18), 6098–6110 (2017)

    Article  CAS  Google Scholar 

  16. F. Dumur, L. Beouch, M.A. Tehfe, E. Contal, M. Lepeltier, G. Wantz, B. Graff, F. Goubard, C.R. Mayer, J. Lalevee, D. Gigmes, Low-cost zinc complexes for white organic light-emitting devices. Thin Solid Films 564, 351–360 (2014)

    Article  CAS  Google Scholar 

  17. M.G. Kaplunov, S.S. Krasnikova, S.L. Nikitenko, N.L. Sermakasheva, I.K. Yakushchenko, Exciplex electroluminescence and photoluminescence spectra of the new organic materials based on zinc complexes of sulphanylamino-substituted ligands. Nanoscale Res. Lett. 7, 206 (2012)

    Article  CAS  Google Scholar 

  18. Y. Sakai, Y. Sagara, H. Nomura, N. Nakamura, Y. Suzuki, H. Miyazaki, C. Adachi, Zinc complexes exhibiting highly efficient thermally activated delayed fluorescence and their application to organic light-emitting diodes. Chem. Commun. 51(15), 3181–3184 (2015)

    Article  CAS  Google Scholar 

  19. R.J. Wang, L.J. Deng, M. Fu, J.L. Cheng, J.Y. Li, Novel Zn-II complexes of 2-(2-hydroxyphenyl)benzothiazoles ligands: electroluminescence and application as host materials for phosphorescent organic light-emitting diodes. J. Mater. Chem. 22(44), 23454–23460 (2012)

    Article  CAS  Google Scholar 

  20. M. Janghouri, S. Minasian, M. Mahmoudi, S. Eyvazi, Photo/electroluminescence and electron transport properties of new zinc complexes. Opt. Mater. 89, 488–493 (2019)

    Article  CAS  Google Scholar 

  21. Y.P. Huo, J.G. Lu, T.H. Lu, X.M. Fang, X.H. Ouyang, L. Zhang, G.Z. Yuan, Comparative studies on OLED performances of chloro and fluor substituted Zn(II) 8-hydroxyquinolinates. New J. Chem. 39(1), 333–341 (2015)

    Article  CAS  Google Scholar 

  22. R. Lakshmanan, N.C. Shivaprakash, S. Sindhu, Switching from sky blue to deep green fluorescent Zn(II) complexes for OLEDs applications. J. Lumin. 196, 136–145 (2018)

    Article  CAS  Google Scholar 

  23. F. Dumur, Zinc complexes in OLEDs: an overview. Synthetic Met. 195, 241–251 (2014)

    Article  CAS  Google Scholar 

  24. X.J. Xu, Y. Liao, G. Yu, H. You, C.G. Di, Z.M. Su, D.G. Ma, Q. Wang, S.Y. Li, S.Q. Wang, J.P. Ye, Y.Q. Liu, Charge carrier transporting, photoluminescent, and electroluminescent properties of zinc(II)-2-(2-hydroxyphenyl)benzothiazolate complex. Chem. Mater. 19(7), 1740–1748 (2007)

    Article  CAS  Google Scholar 

  25. S.G. Roh, Y.H. Kim, K.D. Seo, D.H. Lee, H.K. Kim, Y.I. Park, J.W. Park, J.H. Lee, Synthesis, photophysical, and electroluminescent device properties of Zn(II)-chelated complexes based on functionalized benzothiazole derivatives. Adv. Funct. Mater. 19(10), 1663–1671 (2009)

    Article  CAS  Google Scholar 

  26. C.S. Oh, J.Y. Lee, High triplet energy Zn complexes as host materials for green and blue phosphorescent organic light-emitting diodes. Dyes Pigments 99(2), 374–377 (2013)

    Article  CAS  Google Scholar 

  27. K. Wang, F.C. Zhao, C.G. Wang, S.Y. Chen, D. Chen, H.Y. Zhang, Y. Liu, D.G. Ma, Y. Wang, High-performance red, green, and blue electroluminescent devices based on blue emitters with small singlet-triplet splitting and ambipolar transport property. Adv. Funct. Mater. 23(21), 2672–2680 (2013)

    Article  CAS  Google Scholar 

  28. K. Gao, K.K. Liu, X.L. Li, X.Y. Cai, D.J. Chen, Z.D. Xu, Z.Z. He, B.B. Li, Z.Y. Qiao, D.C. Chen, Y. Cao, S.J. Su, An ideal universal host for highly efficient full-color, white phosphorescent and TADF OLEDs with a simple and unified structure. J. Mater. Chem. C 5(39), 10406–10416 (2017)

    Article  CAS  Google Scholar 

  29. T. Chatterjee, W.Y. Hung, W.F. Tang, H.F. Chen, K.T. Wong, Carbazole-bridged triphenylamine-bipyridine bipolar hosts for high-efficiency low roll-off multi-color PhOLEDs. Org. Electron. 50, 204–212 (2017)

    Article  CAS  Google Scholar 

  30. Y.Q. Miao, K.X. Wang, L. Gao, B. Zhao, H. Wang, F.R. Zhu, B.S. Xu, D.G. Ma, Precise manipulation of the carrier recombination zone: a universal novel device structure for highly efficient monochrome and white phosphorescent organic light-emitting diodes with extremely small efficiency roll-off. J. Mater. Chem. C 6(30), 8122–8134 (2018)

    Article  CAS  Google Scholar 

  31. T.L. Chiu, H.J. Chen, T.C. Lin, H.J. Gau, Y.H. Hsieh, J.J. Huang, L.K. Yun, J.H. Lee, M.K. Leung, Colour stability of blue-green and white phosphorescent organic light-emitting diode employing a 9-(2-(4,5-diphenyl-4H-1,2,4-triazol-3-yl)phenyl)-9H-carbazole host. Dyes Pigments 141, 463–469 (2017)

    Article  CAS  Google Scholar 

  32. C.J. Zheng, C.L. Liu, K. Wang, S.L. Tao, H. Lin, C.S. Lee, Novel bipolar host for highly efficient green, yellow, orange, red and deep-red phosphorescent organic light-emitting devices. Sci. China Chem. 60(4), 504–509 (2017)

    Article  CAS  Google Scholar 

  33. Y.X. Hu, X. Xia, W.Z. He, H.J. Chi, Y. Dong, G.Y. Xiao, Y.L. Lv, X. Li, D.Y. Zhang, Novel Ir(III) complexes ligated with 2-(2,6-difluoropyridin-3-yl)benzo d thiazole for highly efficient OLEDs with mild efficiency roll-off. Dyes Pigments 166, 254–259 (2019)

    Article  CAS  Google Scholar 

  34. D. Liu, R.J. Yao, R.Z. Dong, F.J. Jia, M. Fu, A strategy to increase phosphorescent efficiency without perturbing emission color for benzothiazole-containing iridium phosphors. Dyes Pigments 145, 528–537 (2017)

    Article  CAS  Google Scholar 

  35. S.H. Ye, L. Li, M. Zhang, Z. Zhou, M.H. Quan, L.F. Guo, Y. Wang, M. Yang, W.Y. Lai, W. Huang, Pyridine linked fluorene hybrid bipolar host for blue, green, and orange phosphorescent organic light-emitting diodes toward solution processing. J. Mater. Chem. C 5(45), 11937–11946 (2017)

    Article  CAS  Google Scholar 

  36. J.H. Jang, H.J. Park, J.Y. Park, H.U. Kim, D.H. Hwang, Orange phosphorescent Ir(III) complexes consisting of substituted 2-phenylbenzothiazole for solution-processed organic light-emitting diodes. Org. Electron. 60, 31–37 (2018)

    Article  CAS  Google Scholar 

  37. H.H. Chou, C.H. Cheng, A highly efficient universal bipolar host for blue, green, and red phosphorescent OLEDs. Adv. Mater. 22(22), 2468–2471 (2010)

    Article  CAS  Google Scholar 

  38. S.J. Su, C. Cai, J. Takamatsu, J. Kido, A host material with a small singlet-triplet exchange energy for phosphorescent organic light-emitting diodes: guest, host, and exciplex emission. Org. Electron. 13(10), 1937–1947 (2012)

    Article  CAS  Google Scholar 

  39. S.J. Su, C. Cai, J. Kido, RGB phosphorescent organic light-emitting diodes by using host materials with heterocyclic cores: Effect of nitrogen atom orientations. Chem. Mater. 23(2), 274–284 (2011)

    Article  CAS  Google Scholar 

  40. S.J. Su, C. Cai, J. Kido, Three-carbazole-armed host materials with various cores for RGB phosphorescent organic light-emitting diodes. J. Mater. Chem. 22(8), 3447–3456 (2012)

    Article  CAS  Google Scholar 

  41. Y.Y. Lyu, J. Kwak, W.S. Jeon, Y. Byun, H.S. Lee, D. Kim, C. Lee, K. Char, Highly efficient red phosphorescent OLEDs based on non-conjugated silicon-cored spirobifluorene derivative doped with Ir-complexes. Adv. Funct. Mater. 19(3), 420–427 (2009)

    Article  CAS  Google Scholar 

  42. H. Kim, Y. Byun, R.R. Das, B.K. Choi, P.S. Ahn, Small molecule based and solution processed highly efficient red electrophosphorescent organic light emitting devices. Appl. Phys. Lett. 91(9), 093512 (2007)

    Article  CAS  Google Scholar 

  43. R.D. Guo, W.Z. Zhang, Q. Zhang, X.L. Lv, L. Wang, Efficient deep red phosphorescent OLEDs using 1,2,4-thiadiazole core-based novel bipolar host with low efficiency roll-off. Front. Optoelectron. 11(4), 375–384 (2018)

    Article  Google Scholar 

  44. X. Wang, J. Zhou, J. Zhao, Z.Y. Lu, J.S. Yu, High performance fluorescent and phosphorescent organic light-emitting diodes based on a charge-transfer-featured host material. Org. Electron. 21, 78–85 (2015)

    Article  CAS  Google Scholar 

  45. S. Grigalevicius, D. Tavgeniene, G. Krucaite, R. Griniene, W.C. Li, D. Luo, C.H. Chang, 9,9’-Bis(2,2-diphenylvinyl)-3,3’-bicarbazole as low cost efficient hole transporting material for application in red PhOLEDs. Dyes Pigments 152, 100–104 (2018)

    Article  CAS  Google Scholar 

  46. C.H. Chang, R. Griniene, Y.D. Su, C.C. Yeh, H.C. Kao, J.V. Grazulevicius, D. Volyniuk, S. Grigalevicius, Efficient red phosphorescent OLEDs employing carbazole-based materials as the emitting host. Dyes Pigments 122, 257–263 (2015)

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by National Key Research and Development Project of China (2018YFB0407102), National Natural Science Foundation of China (51903026, 61505018, U1663229, 21603020, 61705026, 51903027), Financial Projects of Sichuan Science and Technology Department (2018ZYZF0062), Natural Science Foundation of Chongqing Science & Technology Commission (cstc2020jcyj-msxmX0474, cstc2017zdcy-yszxX0004, cstc2019jcyjjq0092, cstc2018jszx-cyzdX0137, cstc2016jcyjA0577, cstc2018jcyjAX0212, cstc2019jcyjjqx0021, cstc2018jcyjAX0292), Science and Technology Innovation Leader Plan of Chongqing (T04040012), Science and Technology Research Program of Chongqing Municipal Education Commission (KJQN201901314, KJZD-K201901302, KJ1711269, KJQN201801332, KJQN202001304, KJQN201801317), the Chongqing University Outstanding Achievement Transformation Projects (KJZH17130), Overseas Returnees Support Program for Innovation and Entrepreneurship of Chongqing (cx2018136), Public Service Platform for Industrialization of Technological Innovation Achievements in the Field of Robot and Intelligent Manufacturing in Chongqing (2019-00900-1-1). This work is also sponsored by Sichuan Province Key Laboratory of Display Science and Technology.

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Authors and Affiliations

  1. State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Optoelectronic Science and Engineering, University of Electronic Science and Technology of China (UESTC), Chengdu, 610054, People’s Republic of China

    Heng Yu & Junsheng Yu

  2. Micro/Nano Optoelectronic Materials and Devices International Science and Technology Cooperation Base of China, Chongqing University of Arts and Sciences, Chongqing, 402160, People’s Republic of China

    Heng Yu, Shanyong Chen, Youwei Guan & Lu Li

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  1. Heng Yu
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The experimental work was done by the first author. Data verification and guidance were done by other authors.

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Yu, H., Yu, J., Chen, S. et al. Novel phenanthro[9,10-d]imidazole-zinc complex as a host for high-performance OLEDs. J Mater Sci: Mater Electron 32, 22459–22471 (2021). https://doi.org/10.1007/s10854-021-06732-6

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