Pure Hydrocarbon Host Materials Based on 9,9'-Spirobifluorene/Naphthalene Hybrid

doi:10.6023/cjoc202108017

Abstract

The utilization of host-guest doped structure of phosphorescent organic light-emitting diodes helps avoid the triplet exciton concentration quenching, thus improve the device performance. 9,9'-Spirobifluorene (SBF) and its derivatives with a unique orthogonal configuration and rigid framework, exhibit high glass transition temperature, high triplet energy levels, and potential to be used as host materials. In this work, two types of SBF-based pure hydrocarbon (PHC) phosphorescent light-emitting device host materials were synthesized and characterized by introducing naphthalene, named 1,4-SBF-Nap and 1,8-Oct-Nap. 1,8-Oct-Nap has an interestingly cyclized cites and resulting in an octatomic ring structure instead of normal SBF. Co-evaporating with bis(2-methyldibenzo[f,h]quinoxaline)(acetylacetonate)iridium(III) (Ir(MDQ)₂(acac)), the red-light devices based on these two hosts were successfully fabricated. The maximum external quantum efficiencies (EQE) were 15.0% and 13.7% for 1,4-SBF-Nap and 1,8-Oct-Nap, respectively. The diversity of the PHC host materials can be expanded by the utilization of naphthalene.

Key words: organic light-emitting diode, host, 9,9'-spirobifluorene, naphthalene, octatomic ring

Cite this article

Qi Zheng, Ya Wen, Yangkun Qu, Yuanhao Zhu, Mankeung Fung, Zuoquan Jiang. Pure Hydrocarbon Host Materials Based on 9,9'-Spirobifluorene/Naphthalene Hybrid[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 572-579.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 8

Scheme 1. Synthetic routes of 1,4-SBF-Nap and 1,8-Oct-Nap.

Figure 1. Theoretical calculations of the possible intermediate spatial structures of 1,8-Oct-Nap using DFT[24] (ground states) at the pbe0 [25] (em=gd3bj)[26]/def2svp[27] level

Figure 2. Theoretical HOMO/LUMO energy levels and distributions, singlet and triplet excitation energies, and electron-hole analysis of singlet and triplet excited states, for 1,4-SBF-Nap and 1,8-Oct-Nap using DFT (ground states) at the pbe0[25] (em=gd3bj)[26]/def2svp[27] level and TD-DFT (excited states) at the cam-b3lyp[30] (em=gd3bj)[26]/def2svp[27] level

Figure 3. Crystal structures and crystal packing modes of 1,4-SBF-Nap and 1,8-Oct-Nap

Figure 4. UV-vis absorption, fluorescence, and phosphorescent (77 K) spectra of 1,4-SBF-Nap and 1,8-Oct-Nap

Figure 5. Cyclic voltammetry in CH2Cl2/[Bu4NPF6] 0.1 mol/L (100 mV•s–1) of 1,4-SBF-Nap and 1,8-Oct-Nap

Figure 6. PhOLED device performance PhOLED device characteristics of 1,4-SBF-Nap (red), 1,8-Oct-Nap (blue) and mCP (black). (a) EQE versus luminance characteristics; (b) current density and luminance versus driving voltage (J-V-L) characteristics; (c) current efficiency and power efficiency versus luminance characteristics; (d) device structures of PhOLEDs based on 1,4-SBF-Nap, 1,8-Oct-Nap, and mCP, with functional materials including HAT-CN, TAPC, TCTA, Ir(MDQ)2(acac), B4PyMPM, Liq and Al

Host	V_on/V₁₀₀^a/V	CE_max^b/(cd•A^–1)	PE_max^b/(lm•W^–1)	EQE_max^b/%	λ_max^c/nm	CIE (x, y)^c
1,4-SBF-Nap	3.6/4.8	25.5/18.8/12.7	22.3/12.2/5.6	15.0/11.0/7.3	608	(0.61, 0.38)
1,8-Oct-Nap	3.0/4.2	21.9/14.4/9.7	22.9/10.8/5.1	13.7/9.0/6.1	608	(0.62, 0.38)
mCP	2.8/3.2	22.6/22.6/19.2	22.3/22.2/14.4	13.8/13.8/11.7	608	(0.61, 0.38)

Table 1. Summary of device performances

References 31

[1]	Baldo, M. A.; O'Brien, D. F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M. E.; Forrest, S. R. Nature 1998, 395(6698), 151. doi: 10.1038/25954
[2]	Pu, Y.-J.; Nakata, G.; Satoh, F.; Sasabe, H.; Yokoyama, D.; Kido, J. Adv. Mater. 2012, 24(13), 1765. doi: 10.1002/adma.201104403
[3]	Cui, L.-S.; Dong, S.-C.; Liu, Y.; Li, Q.; Jiang, Z.-Q.; Liao, L.-S. J. Mater. Chem. C 2013, 1(25), 3967. doi: 10.1039/c3tc30410h
[4]	Tao, Y.; Yang, C.; Qin, J. Chem. Soc. Rev. 2011, 40(5), 2943. doi: 10.1039/c0cs00160k
[5]	Quinton, C.; Thiery, S.; Jeannin, O.; Tondelier, D.; Geffroy, B.; Jacques, E.; Rault-Berthelot, J.; Poriel, C. ACS Appl. Mater. Interfaces 2017, 9(7), 6194. doi: 10.1021/acsami.6b14285
[6]	Maheshwaran, A.; Sree, V. G.; Park, H.-Y.; Kim, H.; Han, S. H.; Lee, J. Y.; Jin, S.-H. Adv. Funct. Mater. 2018, 28(36), 1802945. doi: 10.1002/adfm.v28.36
[7]	Poriel, C.; Rault-Berthelot, J.; Thiery, S.; Quinton, C.; Jeannin, O.; Biapo, U.; Tondelier, D.; Geffroy, B. Chem.-Eur. J. 2016, 22(50), 17930. doi: 10.1002/chem.201603659
[8]	Bai, Q.; Liu, H.; Yao, L.; Shan, T.; Li, J.; Gao, Y.; Zhang, Z.; Liu, Y.; Lu, P.; Yang, B.; Ma, Y. ACS Appl. Mater. Interfaces 2016, 8(37), 24793. doi: 10.1021/acsami.6b09488
[9]	Poriel, C.; Rault-Berthelot, J. J. Mater. Chem. C 2017, 5(16), 3869. doi: 10.1039/C7TC00746A
[10]	Lin, N.; Qiao, J.; Duan, L.; Li, H.; Wang, L.; Qiu, Y. J. Phys. Chem. C 2012, 116(36), 19451. doi: 10.1021/jp305415x
[11]	Lin, N.; Qiao, J.; Duan, L.; Wang, L.; Qiu, Y. J. Phys. Chem. C 2014, 118(14), 7569. doi: 10.1021/jp412614k
[12]	Cui, L.-S.; Xie, Y.-M.; Wang, Y.-K.; Zhong, C.; Deng, Y.-L.; Liu, X.-Y.; Jiang, Z.-Q.; Liao, L.-S. Adv. Mater. 2015, 27(28), 4213. doi: 10.1002/adma.v27.28
[13]	Shao, J.; Zhong, Y. Chin. J. Org. Chem. 2021, 41(4), 1447. (in Chinese) doi: 10.6023/cjoc202009033
	( 邵将洋; 钟羽武, 有机化学, 2021, 41(4), 1447.) doi: 10.6023/cjoc202009033
[14]	Clarkson, R. G.; Gomberg, M. J. Am. Chem. Soc. 1930, 52(7), 2881. doi: 10.1021/ja01370a048
[15]	Zeng, W.; Lai, H.-Y.; Lee, W.-K.; Jiao, M.; Shiu, Y.-J.; Zhong, C.; Gong, S.; Zhou, T.; Xie, G.; Sarma, M.; Wong, K.-T.; Wu, C.-C.; Yang, C. Adv. Mater. 2018, 30(5), 1704961. doi: 10.1002/adma.201704961
[16]	Liu, H.; Liu, Z.; Li, G.; Huang, H.; Zhou, C.; Wang, Z.; Yang, C. Angew. Chem., nt. Ed. 2021, 60(22), 12376. doi: 10.1002/anie.v60.22
[17]	Jiang, Z.; Yao, H.; Zhang, Z.; Yang, C.; Liu, Z.; Tao, Y.; Qin, J.; Ma, D. Org. Lett. 2009, 11(12), 2607. doi: 10.1021/ol9008816
[18]	Jiang, Z.; Liu, Z.; Yang, C.; Zhong, C.; Qin, J.; Yu, G.; Liu, Y. Adv. Funct. Mater. 2009, 19(24), 3987. doi: 10.1002/(ISSN)1616-3028
[19]	Sicard, L. J.; Li, H.-C.; Wang, Q.; Liu, X.-Y.; Jeannin, O.; Rault- Berthelot, J.; Liao, L.-S.; Jiang, Z.-Q.; Poriel, C. Angew. Chem., nt. Ed. 2019, 58(12), 3848. doi: 10.1002/anie.v58.12
[20]	Sicard, L.; Quinton, C.; Peltier, J.-D.; Tondelier, D.; Geffroy, B.; Biapo, U.; Métivier, R.; Jeannin, O.; Rault-Berthelot, J.; Poriel, C. Chem.-Eur. J. 2017, 23(32), 7719. doi: 10.1002/chem.v23.32
[21]	Poriel, C.; Sicard, L.; Rault-Berthelot, J. Chem. Commun. 2019, 55 (95), 14238. doi: 10.1039/C9CC07169E
[22]	Poriel, C.; Rault-Berthelot, J. Acc. Chem. Res. 2018, 51(8), 1818. doi: 10.1021/acs.accounts.8b00210
[23]	Dumur, F.; Bui, T.-T.; Péralta, S.; Lepeltier, M.; Wantz, G.; Sini, G.; Goubard, F.; Gigmes, D. RSC Adv. 2016, 6(65), 60565. doi: 10.1039/C6RA13824A
[24]	Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.; Caricato, M.; Marenich, A. V.; Bloino, J.; Janesko, B. G.; Gomperts, R.; Mennucci, B.; Hratchian, H. P.; Ortiz, J. V.; Izmaylov, A. F.; Sonnenberg, J. L.; Williams; Ding, F.; Lipparini, F.; Egidi, F.; Goings, J.; Peng, B.; Petrone, A.; Henderson, T.; Ranasinghe, D.; Zakrzewski, V. G.; Gao, J.; Rega, N.; Zheng, G.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M. J.; Heyd, J. J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Keith, T. A.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Millam, J. M.; Klene, M.; Adamo, C.; Cammi, R.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Farkas, O.; Foresman, J. B.; Fox, D. J. Gaussian 16 Revision C. 01, Wallingford, CT, 2016.
[25]	Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77(18), 3865. doi: 10.1103/PhysRevLett.77.3865 pmid: 10062328
[26]	Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32(7), 1456. doi: 10.1002/jcc.v32.7
[27]	Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7(18), 3297. doi: 10.1039/b508541a
[28]	Lu, T.; Chen, F. J. Comput. Chem. 2012, 33(5), 580. doi: 10.1002/jcc.v33.5
[29]	Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graph. 1996, 14(1), 33. doi: 10.1016/0263-7855(96)00018-5 pmid: 8744570
[30]	Yanai, T.; Tew, D. P.; Handy, N. C. Chem. Phys. Lett. 2004, 393(1), 51. doi: 10.1016/j.cplett.2004.06.011
[31]	Demeter, A.; Timári, G.; Kotschy, A.; Bérces, T. Tetrahedron Lett. 1997, 38(29), 5219. doi: 10.1016/S0040-4039(97)01107-6

基于9,9'-螺二芴和萘的纯碳氢主体材料