Donor-acceptor-structured 1,4-diazatriphenylene derivatives exhibiting thermally activated delayed fluorescence: design and synthesis, photophysical properties and OLED characteristics

被引:65
作者
Takahashi, Takehiro [1 ,2 ]
Shizu, Katsuyuki [1 ]
Yasuda, Takuma [1 ,3 ,4 ,5 ]
Togashi, Kazunori [1 ,2 ]
Adachi, Chihaya [1 ,3 ,4 ]
机构
[1] Kyushu Univ, Ctr Organ Photon & Elect Res OPERA, Nishi Ku, Fukuoka 812, Japan
[2] Hodogaya Chem Co, Tsukuba, Ibaraki, Japan
[3] Kyushu Univ, Dept Appl Chem, Fukuoka 812, Japan
[4] Kyushu Univ, Int Inst Carbon Neutral Energy Res WPI I2CNER, Fukuoka 812, Japan
[5] Japan Sci & Technol Agcy JST, PRESTO, Chiyoda Ku, Tokyo 1020076, Japan
关键词
organic light-emitting diodes; 1,4-diazatriphenylene; thermally activated delayed fluorescence; donor-acceptor; LIGHT-EMITTING-DIODES; HOST MATERIALS; ENERGY; APPROXIMATION; EFFICIENCY; POLYMERS; STATES;
D O I
10.1088/1468-6996/15/3/034202
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
A new series of luminescent 1,4-diazatriphenylene (ATP) derivatives with various peripheral donor units, including phenoxazine, 9,9-dimethylacridane and 3-(diphenylamino)carbazole, is synthesized and characterized as thermally activated delayed fluorescence (TADF) emitters. The influence of the donor substituents on the electronic and photophysical properties of the materials is investigated by theoretical calculations and experimental spectroscopic measurements. These ATP-based molecules with donor-acceptor-donor (D-A-D) structures can reduce the singlet-triplet energy gap (0.04-0.26 eV) upon chemical modification of the ATP core, and thus exhibit obvious TADF characteristics in solution and doped thin films. As a demonstration of the potential of these materials, organic light-emitting diodes containing the D-A-D-structured ATP derivatives as emitters are fabricated and tested. External electroluminescence quantum efficiencies above 12% and 8% for green- and sky-blue-emitting devices, respectively, are achieved.
引用
收藏
页数:10
相关论文
共 28 条
[1]   Nearly 100% internal phosphorescence efficiency in an organic light-emitting device [J].
Adachi, C ;
Baldo, MA ;
Thompson, ME ;
Forrest, SR .
JOURNAL OF APPLIED PHYSICS, 2001, 90 (10) :5048-5051
[2]   FAST PHOTOCONDUCTION IN THE HIGHLY ORDERED COLUMNAR PHASE OF A DISCOTIC LIQUID-CRYSTAL [J].
ADAM, D ;
SCHUHMACHER, P ;
SIMMERER, J ;
HAUSSLING, L ;
SIEMENSMEYER, K ;
ETZBACH, KH ;
RINGSDORF, H ;
HAARER, D .
NATURE, 1994, 371 (6493) :141-143
[3]  
[Anonymous], PHOSPHORIMETRY
[4]  
[Anonymous], J CHEM PHYS
[5]   Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory [J].
Bauernschmitt, R ;
Ahlrichs, R .
CHEMICAL PHYSICS LETTERS, 1996, 256 (4-5) :454-464
[6]   Preface to the Chemistry of Materials Special Issue on π-Functional Materials [J].
Bredas, Jean-Luc ;
Marder, Seth R. ;
Reichmanis, Elsa .
CHEMISTRY OF MATERIALS, 2011, 23 (03) :309-309
[7]   Carbazole compounds as host materials for triplet emitters in organic light-emitting diodes:: Tuning the HOMO level without influencing the triplet energy in small molecules [J].
Brunner, K ;
van Dijken, A ;
Börner, H ;
Bastiaansen, JJAM ;
Kiggen, NMM ;
Langeveld, BMW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :6035-6042
[8]   Electron and hole transport in a wide bandgap organic phosphine oxide for blue electrophosphorescence [J].
Cai, Xiuyu ;
Padmaperuma, Asanga B. ;
Sapochak, Linda S. ;
Vecchi, Paul A. ;
Burrows, Paul E. .
APPLIED PHYSICS LETTERS, 2008, 92 (08)
[9]   Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold [J].
Casida, ME ;
Jamorski, C ;
Casida, KC ;
Salahub, DR .
JOURNAL OF CHEMICAL PHYSICS, 1998, 108 (11) :4439-4449
[10]   Efficient up-conversion of triplet excitons into a singlet state and its application for organic light emitting diodes [J].
Endo, Ayataka ;
Sato, Keigo ;
Yoshimura, Kazuaki ;
Kai, Takahiro ;
Kawada, Atsushi ;
Miyazaki, Hiroshi ;
Adachi, Chihaya .
APPLIED PHYSICS LETTERS, 2011, 98 (08)