Subscribe to RSS
DOI: 10.1055/s-0039-3402513
Fluorine-Substituted Phenanthro[9,10-d]imidazole Derivatives with Optimized Charge-Transfer Characteristics for Efficient Deep-Blue Emitters
Funding Information This work was supported by the National Natural Science Foundation of China (21935005 and 51803069) and Program for JLU Science and Technology Innovative Research Team (2019TD-33).Publication History
Received: 15 October 2019
Accepted after revision: 19 November 2019
Publication Date:
23 January 2020 (online)
Abstract
The development of high-efficiency deep-blue emitters is of great importance for full-color organic light-emitting diodes (OLEDs). In this contribution, three difluorine-substituted phenanthro[9,10-d]imidazole derivatives with optimized charge-transfer character and deep-blue emission have been developed. It is demonstrated that the fluorine substitution can facilitate the “state mixing” of singlet and triplet excitons, which increases the utilization of triplet excitons. The fluorine substitution also brings more intermolecular interactions which have influence on the molecular packing pattern of the solid states, ultimately impacting their carrier mobilities. Through fine-tuning of molecular structures, 4'-(1-(3,5-difluorophenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)-N,N-diphenyl-[1,1'-biphenyl]-4-amine (2FPPIDPA) realized a high exciton utilization ratio with Commission Internationale de L'Eclairage (CIE) coordinates of (0.156, 0.046), and 4'-(1-(3,5-difluorophenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)-N,N-diphenyl-[1,1'-biphenyl]-4-amine (2FPPIDPA) achieved an external quantum efficiency of 8.47% with CIE coordinates of (0.152, 0.083) in multilayer OLEDs. Due to their good hole-transport abilities, double-layer OLEDs without the hole-transport layer showed performances comparable or even superior to the multilayer ones.
Key words
organic light-emitting diodes - blue emitters - phenanthro[9 - 10-d]imidazole - charge-transfer state - fluorine substituentsSupporting Information
Supporting information for this article is available online at: https://doi.org/10.1055/s-0039-3402513.
Primary Data
- Primary Data
Crystal files of 2FPPImTPA, 2FPPIDPA, and 2FPPITPA are provided in CCDC 1939337, 1939338, and 1939339, respectively. Primary data for this article are available online at: https://doi.org/10.1055/s-0039-3402513 and can be cited using the following DOI: 10.5281/zenodo.4610547.
-
References
- 1 Zhu M, Yang C. Chem. Soc. Rev. 2013; 42: 4963
- 2a Tung YJ, Ngo T, Hack M, Brown J, Koide N, Nagara Y, Kato Y, Ito H. SID Symp. Dig. Tech. Pap. 2004; 35: 48
- 2b Lee MT, Liao CH, Tsai CH, Chen CH. Adv. Mater. 2005; 17: 2493
- 3 Chan CY, Tanaka M, Nakanotani H, Adachi C. Nat. Commun. 2018; 9: 5036
- 4a Pershin A, Hall D, Lemaur V, Sancho-Garcia JC, Muccioli L, Zysman-Colman E, Beljonne D, Olivier Y. Nat. Commun. 2019; 10: 597
- 4b Reineke S. Nat. Photonics 2014; 8: 269
- 5a Yao L, Yang B, Ma YG. Sci. China Chem. 2014; 57: 335
- 5b Xu Y, Wang C, Zhou X, Zhou J, Guo X, Liang X, Hu D, Li F, Ma D, Ma Y. J. Phys. Chem. Lett. 2019; 10: 6878
- 6 Li WJ, Liu DD, Shen FZ, Ma DG, Wang ZM, Feng T, Xu YX, Yang B, Ma YG. Adv. Funct. Mater. 2012; 22: 2797
- 7 Zhang S, Li W, Yao L, Pan Y, Shen F, Xiao R, Yang B, Ma Y. Chem. Commun. 2013; 49: 11302
- 8 Zhang S, Yao L, Peng Q, Li W, Pan Y, Xiao R, Gao Y, Gu C, Wang Z, Lu P, Li F, Su S, Yang B, Ma Y. Adv. Funct. Mater. 2015; 25: 1755
- 9 Xu Y, Liang X, Zhou X, Yuan P, Zhou J, Wang C, Li B, Hu D, Qiao X, Jiang X, Liu L, Su SJ, Ma D, Ma Y. Adv. Mater. 2019; 31: 1807388
- 10a Ouyang X, Li XL, Ai L, Mi D, Ge Z, Su SJ. ACS. Appl. Mater. Interfaces 2015; 7: 7869
- 10b Cao C, Chen W.-C, Tian S, Chen J.-X, Wang Z.-Y, Zheng X.-H, Ding C.-W, Li J.-H, Zhu J.-J, Zhu Z.-L, Tong Q.-X, Lee C.-S. Mater. Chem. Front. 2019; 3: 1071
- 10c Cao C, Chen WC, Chen JX, Yang L, Wang XZ, Yang H, Huang B, Zhu ZL, Tong QX, Lee CS. ACS. Appl. Mater. Interfaces 2019; 11: 11691
- 10d Chen L, Zhang S, Li H, Chen R, Jin L, Yuan K, Li H, Lu P, Yang B, Huang W. J. Phys. Chem. Lett. 2018; 9: 5240
- 11a Jo JW, Jung JW, Jung EH, Ahn H, Shin TJ, Jo WH. Energy Environ. Sci. 2015; 8: 2427
- 11b Priimagi A, Cavallo G, Metrangolo P, Resnati G. Acc. Chem. Res. 2013; 46: 2686
- 12 Li W, Pan Y, Yao L, Liu H, Zhang S, Wang C, Shen F, Lu P, Yang B, Ma Y. Adv. Opt. Mater. 2014; 2: 892
- 13 Lu T, Chen F. J. Comput. Chem. 2012; 33: 580
- 14 El-Sayed MA. J. Chem. Phys. 1963; 38: 2834
- 15a Yuan WZ, Shen XY, Zhao H, Lam JW. Y, Tang L, Lu P, Wang C, Liu Y, Wang Z, Zheng Q, Sun JZ, Ma Y, Tang BZ. J. Phys. Chem. C. 2010; 114: 6090
- 15b Li M, Ling K, Shi H, Gan N, Song L, Cai S, Cheng Z, Gu L, Wang X, Ma C, Gu M, Wu Q, Bian L, Liu M, An Z, Ma H, Huang W. Adv. Opt. Mater. 2019; 7: 1800820
- 16 Liu H, Bai Q, Yao L, Zhang H, Xu H, Zhang S, Li W, Gao Y, Li J, Lu P, Wang H, Yang B, Ma Y. Chem. Sci. 2015; 6: 3797
- 17 Mei J, Leung NL, Kwok RT, Lam JW, Tang BZ. Chem. Rev. 2015; 115: 11718
- 18 Fan D, Yi Y, Li Z, Liu W, Peng Q, Shuai Z. J. Phys. Chem. A. 2015; 119: 5233
- 19a Li CL, Li ZQ, Liang JX, Luo H, Liu Y, Wei JB, Wang Y. J. Mater. Chem. C. 2018; 6: 12888
- 19b Li Z, Li C, Xu Y, Xie N, Jiao X, Wang Y. J. Phys. Chem. Lett. 2019; 10: 842
- 20a Wu CC, Lin YT, Wong KT, Chen RT, Chien YY. Adv. Mater. 2004; 16: 61
- 20b Kuwabara Y, Ogawa H, Inada H, Noma N, Shirota Y. Adv. Mater. 1994; 6: 677
- 21 Tang X, Bai Q, Peng Q, Gao Y, Li J, Liu Y, Yao L, Lu P, Yang B, Ma Y. Chem. Mater. 2015; 27: 7050
- 22 Chen WC, Huang B, Ni SF, Xiong Y, Rogach AL, Wan Y, Shen D, Yuan Y, Chen JX, Lo MF, Cao C, Zhu ZL, Wang Y, Wang P, Liao LS, Lee CS. Adv. Funct. Mater. 2019; 29: 1903112
- 23 Chiang C.-J, Kimyonok A, Etherington MK, Griffiths GC, Jankus V, Turksoy F, Monkman AP. Adv. Funct. Mater. 2013; 23: 739
- 24 Brutting W, Frischeisen J, Schmidt TD, Scholz BJ, Mayr C. Phys. Status Solidi A 2013; 210: 44
- 25 Baldo MA, O'Brien DF, Thompson ME, Forrest SR. Phys. Rev. B: Condens. Matter 1999; 60: 14422