可溶液加工的蒽醌/芴类双极性荧光材料的合成及其光电性质

doi:10.3866/PKU.WHXB201605163

Abstract

Abstract:

The solution-processable, anthraquinone-based, fluorene bipolar fluorescent material 2-(9, 9'-bis (2-ethylhexyl)-9H-fluoren-2-yl)anthracene-9, 10-dione (FAA) was synthesized via a Suzuki reaction. The photophysical properties of FAAwere subsequently investigated by acquiring absorption and photoluminescence spectra, and its optical properties were studied using computational density functional theory methods. Data obtained from single-carrier devices incorporating FAA demonstrated its well-matched bipolar charge-transport characteristics. The electroluminescence performance of this material was also examined by doping FAA into a 1, 3-di(9H-carbazol-9-yl)benzene (mCP) matrix as the light-emitting layer via spin coating to produce an organic light-emitting diode (OLED) with an indiumtin oxide (ITO)/poly(3, 4-ethylenedioxythiophene:poly(styrenesulfonate) (PEDOT:PSS)/mCP:FAA/3, 3'-(5'-(3-(pyridin-3-yl)phenyl)-[1, 1':3', 1"-terphen-yl]-3, 3"-diyl)dipyridine (TmPyPb)/ LiF/Al structure. This device exhibited a maximum luminance of 1719 cd·m^-2 with a turn-on voltage of 7.4 V, along with maximum current and power efficiencies of 1.66 cd·A^-1 and 0.56 lm·W^-1, respectively. The electroluminescence mechanism of the OLED is discussed based on the energy level diagrams of the functional layers.

Key words: Organic light-emitting diode, Solution processing, Fluorescent material, Bipolar characteristics, Anthraquinone

MSC2000:

O649

Hao CHEN,Tao YANG,Jie-Wei LI,Xin-Wen ZHANG,Yan QIAN,Ling-Hai XIE,Wei HUANG. Synthesis and Optoelectronic Properties of a Solution-Processable Anthraquinone/Fluorene Hybrid Bipolar Fluorescent Material[J].Acta Phys. -Chim. Sin., 2016, 32(9): 2346-2354.

References

1	Baldo M. A. ; O'Brien D. F. ; You Y. ; Shoustikov A. ; Sibley S. ; Thompson M. E. ; Forrest S. R. Nature 1998, 395 (6698), 151d.
2	Muller C. D. ; Falcou A. ; Reckefuss N. ; Rojahn M. ; Wiederhirn V. ; Rudati P. ; Frohne H. ; Nuyken O. ; Becker H. ; Meerholz K. Nature 2003, 421 (6925), 829.
3	Sun Y. R. ; Giebink N. C. ; Kanno H. ; Ma B.W. ; Thompson M. E. ; Forrest S. R. Nature 2006, 440 (7086), 908.
4	Uoyama H. ; Goushi K. ; Shizu K. ; Nomura H. ; Adachi C. Nature 2012, 492 (7428), 234.
5	Kaji H. ; Suzuki H. ; Fukushima T. ; Shizu K. ; Suzuki K. ; Kubo S. ; Komino T. ; Oiwa H. ; Suzuki F. ; Wakamiya A. ; Murata Y. ; Adachi C. Nat. Commun 2015, 6, 8.
6	Cai M. ; Xiao T. ; Hellerich E. ; Chen Y. ; Shinar R. ; Shinar J. Adv. Mater. 2011, 23 (31), 3590.
7	Aizawa N. ; Pu Y. J. ; Watanabe M. ; Chiba T. ; Ideta K. ; Toyota N. ; Igarashi M. ; Suzuri Y. ; Sasabe H. ; Kido J. Nat. Commun 2014, 5, 7.
8	H?fle S. ; Schienle A. ; Bernhard C. ; Bruns M. ; Lemmer U. ; Colsmann A. Adv. Mater. 2014, 26 (30), 5155.
9	Zhang X.W. ; Yang T. ; Wei Q. ; Chen Y. H. ; Guo X. ; Xie L.H. ; Lai W. Y. ; Fan Q. L. ; Qian Y. ; Huang W. RSC Adv. 2015, 5 (114), 94077.
10	Liu H. ; Bai Q. ; Yao L. ; Hu D. H. ; Tang X. Y. ; Shen F. Z. ; Zhang H. H. ; Gao Y. ; Lu P. ; Yang B. ; Ma Y. G. Adv. Funct. Mater. 2014, 24 (37), 5881.
11	Oh H. Y. ; Kulshreshtha C. ; Kwon J. H. ; Lee S. Org. Electron 2010, 11 (10), 1624.
12	Perumal A. ; Faber H. ; Yaacobi-Gross N. ; Pattanasattayavong P. ; Burgess C. ; Jha S. ; McLachlan M. A. ; Stavrinou P. N. ; Anthopoulos T. D. ; Bradley D. D. C. Adv. Mater. 2015, 27 (1), 93.
13	Yook K. S. ; Lee J. Y. Adv. Mater. 2014, 26 (25), 4218d.
14	Chiba T. ; Pu Y. J. ; Kido J. Adv. Mater. 2015, 27 (32), 4681d.
15	Huang M. H. ; Lin W. C. ; Fan C. C. ; Wang Y. S. ; Lin H.W. ; Liao J. L. ; Lin C. H. ; Chi Y. Org. Electron 2015, 20, 36d.
16	Cho Y. J. ; Yook K. S. ; Lee J. Y. Adv. Mater. 2014, 26 (38), 6642.
17	Huang T. H. ; Lin J. T. ; Chen L. Y. ; Lin Y. T. ; Wu C. C. Adv. Mater. 2006, 18 (5), 602.
18	Lin S. L. ; Chan L. H. ; Lee R. H. ; Yen M. Y. ; Kuo W. J. ; Chen C. T. ; Jeng R. J. Adv. Mater. 2008, 20 (20), 3947d.
19	Chaskar A. ; Chen H. F. ; Wong K. T. Adv. Mater. 2011, 23 (34), 3876.
20	Duan L. A. ; Qiao J. A. ; Sun Y. D. ; Qiu Y. Adv. Mater. 2011, 23 (9), 1137.
21	Hudson Z. M. ; Wang Z. B. ; Helander M. G. ; Lu Z. H. ; Wang S. N. Adv. Mater. 2012, 24 (21), 2922.
22	Lee C.W. ; Lee J. Y. Adv. Mater. 2013, 25 (4), 596d.
23	Hu J. Y. ; Pu Y. J. ; Satoh F. ; Kawata S. ; Katagiri H. ; Sasabe H. ; Kido J. Adv. Funct. Mater. 2014, 24 (14), 2064d.
24	Wang F. F. ; Tao Y. T. ; Huang W. Acta Chim. Sin. 2015, 73 (1), 9.
24	王芳芳; 陶友田; 黄维. 化学学报, 2015, 73 (1), 9d.
25	Zhong B. F. ; Wang S. R. ; Xiao Y. ; Li X. G. Prog. Chem. 2015, 27 (8), 986.
25	钟渤凡; 王世荣; 肖殷; 李祥高. 化学进展, 2015, 27 (8), 986.
26	Ge Z. ; Hayakawa T. ; Ando S. ; Ueda M. ; Akiike T. ; Miyamoto H. ; Kajita T. ; Kakimoto M. A. Chem. Mater. 2008, 20 (7), 2532.
27	Gong S. L. ; Fu Q. ; Wang Q. ; Yang C. L. ; Zhong C. ; Qin J.G. ; Ma D. G. Adv. Mater. 2011, 23 (42), 4956.
28	Kong S. ; Xiao L. X. ; Liu Y. L. ; Chen Z. J. ; Qu B. ; Gong Q. H. New J. Chem. 2010, 34 (9), 1994.
29	Zhang M. ; Xue S. F. ; Dong W. Y. ; Wang Q. ; Fei T. ; Gu C. ; Ma Y. G. Chem. Commun. 2010, 46 (22), 3923.
30	Jiang W. ; Ban X. X. ; Sun Y. M. RSC Adv. 2015, 5 (82), 66994d.
31	Jou J. H. ; Kumar S. ; Fang P. H. ; Venkateswararao A. ; Thomas K. R. J. ; Shyue J. J. ; Wang Y. C. ; Li T. H. ; Yu H. H. J. Mater. Chem. C 2015, 3 (10), 2182.
32	Ye J. ; Chen Z. ; Fung M. K. ; Zheng C. J. ; Ou X. M. ; Zhang X. H. ; Yuan Y. ; Lee C. S. Chem. Mater. 2013, 25 (13), 2630d.
33	Chen C. T. ; Wei Y. ; Lin J. S. ; Moturu M. V. R. K. ; Chao W.S. ; Tao Y. T. ; Chien C. H. J. Am. Chem. Soc. 2006, 128 (34), 10992.
34	Chi C. C. ; Chiang C. L. ; Liu S.W. ; Yueh H. ; Chen C. T. ; Chen C. T. J. Mater. Chem. 2009, 19 (31), 5561.
35	Zhao Y. L. ; Duan L. ; Qiao J. ; Zhang D. Q. ; Wang L. D. ; Qiu Y. Acta Phys. -Chim. Sin. 2010, 26 (3), 531.
35	赵云龙; 段炼; 乔娟; 张德强; 王立铎; 邱勇. 物理化学学报, 2010, 26 (3), 531.
36	Tang X. Y. ; Bai Q. ; Peng Q. M. ; Gao Y. ; Li J. Y. ; Liu Y. L. ; Yao L. ; Lu P. ; Yang B. ; Ma Y. G. Chem. Mater. 2015, 27 (20), 7050.
37	Mallesham G. ; Swetha C. ; Niveditha S. ; Mohanty M. E. ; Babu N. J. ; Kumar A. ; Bhanuprakash K. ; Rao V. J. J. Mater. Chem. C. 2015, 3 (6), 1208.
38	Li J.W. ; Qian Y. ; Xie L. H. ; Yi Y. P. ; Li W. W. ; Huang W. J. Phys. Chem. C 2015, 119 (4), 2133.
39	Martin R. E. ; Diederich F. Angew. Chem. Int. Ed. 1999, 38 (10), 1350.
40	Lee S. H. ; Nakamura T. ; Tsutsui T. Org. Lett. 2001, 3 (13), 2005.
41	Setayesh S. ; Grimsdale A. C. ; Weil T. ; Enkelmann V. ; Müllen K. ; Meghdadi F. ; List E. J. W. ; Leising G. J. Am. Chem. Soc. 2001, 123 (5), 946.
42	Xiao L. X. ; Hu S. Y. ; Kong S. ; Chen Z. J. ; Qu B. ; Gong Q.H. Acta Phys. -Chim. Sin. 2011, 27 (4), 977.
42	肖立新; 胡双元; 孔胜; 陈志坚; 曲波; 龚旗煌. 物理化学学报, 2011, 27 (4), 977.
43	Huo Y. P. ; Fang X. M. ; Huang B. H. ; Zhang K. ; Nie X. L. ; Zeng H. P. Chin. J. Org. Chem 2012, 32 (7), 1169.
43	霍延平; 方小明; 黄宝华; 张焜; 聂晓李; 曾和平. 有机化学, 2012, 32 (7), 1169.
44	Chu Z. Z. ; Wang D. ; Zhang C. ; Zou D. C. Acta Phys. -Chim. Sin. 2012, 28 (8), 2000.
44	初增泽; 王丹; 张超; 邹德春. 物理化学学报, 2012, 28 (8), 2000.
45	Kamtekar K. T. ; Wang C. S. ; Bettington S. ; Batsanov A. S. ; Perepichka I. F. ; Bryce M. R. ; Ahn J. H. ; Rabinal M. ; Petty M. C. J. Mater. Chem. 2006, 16 (39), 3823.
46	Lai M. Y. ; Chen C. H. ; Huang W. S. ; Lin J. T. ; Ke T. H. ; Chen L. Y. ; Tsai M. H. ; Wu C. C. Angew. Chem. Int. Ed. 2008, 47 (3), 581.
47	Li Y. ; Li A. Y. ; Li B. X. ; Huang J. ; Zhao L. ; Wang B. Z. ; Li J.W. ; Zhu X. H. ; Peng J. B. ; Cao Y. ; Ma D. G. ; Roncali J. Org. Lett. 2009, 11 (22), 5318.
48	Yu D. H. ; Zhao F. C. ; Zhang Z. ; Han C. M. ; Xu H. ; Li J. ; Ma D. G. ; Yan P. F. Chem. Commun. 2012, 48 (49), 6157d.
49	Feng X. J. ; Chen S. F. ; Ni Y. ; Wong M. S. ; Lam M. M. K. ; Cheah K.W. ; Lai G. Q. Org. Electron 2014, 15 (1), 57d.
50	Zhang Q. S. ; Kuwabara H. ; Potscavage W. J. ; Huang S. P. ; Hatae Y. ; Shibata T. ; Adachi C. J. Am. Chem. Soc. 2014, 136 (52), 18070.
51	Sonntag M. ; Kreger K. ; Hanft D. ; Strohriegl P. ; Setayesh S. ; de Leeuw D. Chem. Mater. 2005, 17 (11), 3031.
52	Cho S. Y. ; Grimsdale A. C. ; Jones D. J. ; Watkins S. E. ; Holmes A. B. J. Am. Chem. Soc. 2007, 129 (39), 11910d.
53	Frisch, M.; Trucks, G.; Schlegel, H.; et al. Gaussian 09, Revision A.1; Gaussian Inc.:Wallingford, CT, 2009.

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Synthesis and Optoelectronic Properties of a Solution-Processable Anthraquinone/Fluorene Hybrid Bipolar Fluorescent Material

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