Synthesis, Physical Properties, and Light-Emitting Diode Performance of Phenazine-Based Derivatives with Three, Five, and Nine Fused Six-Membered Rings

被引:121
作者
Gu, Pei-Yang [1 ]
Zhao, Yongbiao [2 ]
He, Jing-Hui [3 ]
Zhang, Jing [1 ]
Wang, Chengyuan [1 ]
Xu, Qing-Feng [3 ]
Lu, Jian-Mei [3 ]
Sun, Xiao Wei [2 ]
Zhang, Qichun [1 ,4 ]
机构
[1] Nanyang Technol Univ, Sch Mat Sci & Engn, Singapore 639798, Singapore
[2] Nanyang Technol Univ, Sch Elect & Elect Engn, Singapore 639798, Singapore
[3] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
[4] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
ELECTRONIC-PROPERTIES; BISPHENAZINE DERIVATIVES; MEMORY PERFORMANCE; OPTICAL-PROPERTIES; BUILDING-BLOCKS; N-HETEROACENES; SOLID-STATE; SIDE-CHAINS; DONOR; FLUORESCENCE;
D O I
10.1021/jo5027707
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Realizing the control of emission colors of single molecules is very important in the development of full-color emitting materials. Herein, three novel phenazine derivatives (2,3,7,8-tetrakis(decyloxy)phenazine (2a), 2,3-didecyloxy-5,14-diaza-7,12-dioxo-9,10- dicyanopentacene (2b), and 2,3,13,14-tetradecyloxy-5,11,16,22-tetraaza-7,9,18,20-tetraoxo-8,19-dicyanoenneacene (2c)) have been successfully synthesized and fully characterized. Compound 2c can emit blue light in toluene solution (450 nm), green light in the powder/film state (502/562 nm), and red light in the 2c/TFA state (610 nm). The OLED with 2c emits a strong green light at a peak of 536 nm with a maximum luminance of the OLED of about 8600 cd m(-2), which indicates that 2c could be a promising fluorescent dye for OLED applications.
引用
收藏
页码:3030 / 3035
页数:6
相关论文
共 54 条
[1]   Conjugated oligomers incorporating azulene building blocks - seven- vs. five-membered ring connectivity [J].
Amir, Elizabeth ;
Murai, Masahito ;
Amir, Roey J. ;
Cowart, John S., Jr. ;
Chabinyc, Michael L. ;
Hawker, Craig J. .
CHEMICAL SCIENCE, 2014, 5 (11) :4483-4489
[2]   Large N-Heteroacenes: New Tricks for Very Old Dogs? [J].
Bunz, Uwe H. F. ;
Engelhart, Jens U. ;
Lindner, Benjamin D. ;
Schaffroth, Manuel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :3810-3821
[3]   N-Heteroacenes [J].
Bunz, Uwe H. F. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) :6780-6789
[4]   Effect of the Porosity of a Polymer of Intrinsic Microporosity (PIM) on Its Intrinsic Fluorescence [J].
Chen, Shaohua ;
Yi, Wei ;
Duhamel, Jean ;
Heinrich, Kathleen ;
Bengtson, Gisela ;
Fritsch, Detlev .
JOURNAL OF PHYSICAL CHEMISTRY B, 2013, 117 (17) :5249-5260
[5]   Organoboron Compounds with Morphology-Dependent NIR Emissions and Dual-Channel Fluorescent ON/OFF Switching [J].
Cheng, Xiao ;
Li, Di ;
Zhang, Zhenyu ;
Zhang, Hongyu ;
Wang, Yue .
ORGANIC LETTERS, 2014, 16 (03) :880-883
[6]   From molecules to solids with the DMol3 approach [J].
Delley, B .
JOURNAL OF CHEMICAL PHYSICS, 2000, 113 (18) :7756-7764
[7]   Improved performance of electrophosphorescent devices based on Re(CO)3Cl-dipyrido[3,2-a:2′,3′-c]phenazine [J].
Fu, CY ;
Li, MT ;
Su, ZM ;
Hong, Z ;
Li, WL ;
Li, B .
APPLIED PHYSICS LETTERS, 2006, 88 (09)
[8]   Synthesis of Fluorescent C2-Bridged Teraryls and Quateraryls for Blue, Sky-Blue, and Green Color Light-Emitting Devices [J].
Goel, Atul ;
Sharma, Ashutosh ;
Rawat, Madhu ;
Anand, R. S. ;
Kant, Ruchir .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (22) :10873-10880
[9]   Synthesis of tetranitro-oxacalix[4]arene with oligoheteroacene groups and its nonvolatile ternary memory performance [J].
Gu, Pei-Yang ;
Gao, Junkuo ;
Lu, Cai-Jian ;
Chen, Wangqiao ;
Wang, Chengyuan ;
Li, Gang ;
Zhou, Feng ;
Xu, Qing-Feng ;
Lu, Jian-Mei ;
Zhang, Qichun .
MATERIALS HORIZONS, 2014, 1 (04) :446-451
[10]   Synthesis, Characterization, and Nonvolatile Ternary Memory Behavior of a Larger Heteroacene with Nine Linearly Fused Rings and Two Different Heteroatoms [J].
Gu, Pei-Yang ;
Zhou, Feng ;
Gao, Junkuo ;
Li, Gang ;
Wang, Chengyuan ;
Xu, Qing-Feng ;
Zhang, Qichun ;
Lu, Jian-Mei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (38) :14086-14089