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Asymmetric dual-core cyclometalated platinum (II) complex with D-A-A configuration pi conjugated system and application thereof

A D-A-A, conjugated system technology, applied in the direction of platinum group organic compounds, platinum organic compounds, compounds containing elements of group 8/9/10/18 of the periodic table, etc. Coupling is weak, affecting luminous efficiency and other issues, to achieve the effect of enhancing external quantum efficiency, enhancing phosphorescent emission, and reducing the non-radiative transition rate

Inactive Publication Date: 2016-10-12
XIANGTAN UNIV
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  • Abstract
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Problems solved by technology

However, the near-infrared materials of the above-mentioned platinum complexes have obvious efficiency roll-off phenomenon at high current density, which is difficult to meet their universal applicability.
In addition, the π-conjugated system cyclometal platinum complexes containing C^N coordination structure have also been reported in near-infrared luminescent materials, but in this type of materials, the spin coupling between platinum ion orbitals and molecular orbitals is relatively weak, It is easy to produce fluorescence / phosphorescence double emission, which affects the luminous efficiency
The above-mentioned structural material makes the spin-orbit coupling more sufficient by introducing two symmetrical platinum ions, which can effectively improve the external quantum yield ("Carsten Borek, Kenneth Hanson, Peter I. Djurovich, Mark E. Thompson, Kristen Aznavour, Robert Bau, Yiru Sun, Stephen R. Forrest, Jason Brooks, Lech Michalski and Julie Brown.Angew.Chem.Int.Ed.2007,46,1111."), but this type of structure has not been reported in near-infrared devices

Method used

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  • Asymmetric dual-core cyclometalated platinum (II) complex with D-A-A configuration pi conjugated system and application thereof
  • Asymmetric dual-core cyclometalated platinum (II) complex with D-A-A configuration pi conjugated system and application thereof
  • Asymmetric dual-core cyclometalated platinum (II) complex with D-A-A configuration pi conjugated system and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Binuclear Cyclometallic Platinum Complexes (Py-Py-Pyr)[Pt(dpm)] 2 And the synthesis of the corresponding mononuclear cyclometal platinum complex (Py-PyH-Pyr)Pt(dpm).

[0040]

[0041] The synthetic method of intermediate 1, 2, 3 refers to literature ("Teresa M.Figueira-Duarte, Sascha C. Simon, Manfred Wagner, Sergey I. Druzhi nin, Klaas A. Zachariasse, Klaus Müllen. Angew Chem Int Ed. 2008, 47, 10176.")

[0042] Synthesis of 7-tert-butyl-1-(5-bromo-2-pyridyl)-pyrene [Intermediate 4]

[0043] Add compound 3 (860mg, 2.2mmol), 2,5-dibromopyridine (630mg, 2.7mmol), Na 2 CO 3 Aqueous solution (4.5M, 5mL), Pd(PPh 3 ) 4 (50mg, 0.045mmol) and THF (10mL), heated to boiling, reacted under nitrogen protection for 24h. Stop the reaction, cool to room temperature, pour the reaction solution into 50 mL of water, and extract with dichloromethane (DCM) (3×25 mL). Anhydrous MgSO for organic phase 4 After drying, filtering, and distilling off the solvent under reduced pressur...

Embodiment 2

[0051] Characterization of properties of asymmetric dinuclear cyclometal platinum complexes in D-A-A configuration π-conjugated system, fabrication of single-emitting layer polymer electroluminescent devices and testing of their luminescent properties.

[0052] Asymmetric Binuclear Cyclometallic Platinum Complexes of D-A-A Configuration π Conjugated System 1 H NMR, 13 The C NMR spectrum was measured by a Bruker Dex-400NMR instrument, the UV-visible absorption spectrum was measured by a CARY100 UV-visible spectrometer, and the photoluminescence spectrum was measured by a Perkin-Elmer LS-50 fluorescence spectrometer.

[0053] The single-emitting layer polymer electroluminescent device of the asymmetric dinuclear ring metal platinum complex phosphorescent material of the D-A-A configuration π conjugated system includes: indium tin oxide (ITO) conductive glass, polydioxyethylthiophene (PEDOT) electron barrier layer, light-emitting layer, cathode. The light-emitting layer (EML) c...

Embodiment 3

[0059] Photophysical properties of asymmetric dinuclear cyclometal platinum complexes with D-A-A configuration π-conjugated system and performance of single-emitting polymer electroluminescent devices.

[0060] (Py-Py-Pyr)[Pt(dpm)] 2 UV absorption spectrum in dichloromethane (DCM) solution as figure 1 shown. The absorption in the 250-350nm interval is attributed to the π-π* electronic transition allowed by the internal spin of the ligand 1 LC, the absorption in the 375-520nm interval is attributed to the electronic transition in the ligand 1 ILCT and electronic transition between ligand and metal 1 MLCT. (Py-Py-Pyr)[Pt(dpm)] 2 The photoluminescence spectrum in DCM solution as figure 2 shown. Wherein, 450-570nm is the fluorescence emission interval, and 650-850nm is the phosphorescence emission interval. Among them, the 700nm emission peak is mainly the triplet emission of pyrene 3 LC, the emission shoulder at lower energies is mainly 3 ILCT launch. The emission pea...

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Abstract

The invention discloses an asymmetric dual-core cyclometalated platinum (II) complex with a D-A-A configuration pi conjugated system and an application thereof. In the metalated platinum (II) complex, pyrene(triphenylamine and the like)-pyridine-pyridine (D-A-A configuration) is used as a main ligand, 2,2,6,6-tetramethyl-3,5-heptadione is used as an auxiliary ligand, a dual-core coordination mode is adopted, and the middle A unit provides two coordination points; the metalated platinum (II) complex improves the external quantum efficiency by the means of enhancing the molecular rigid structure and molecular spin-orbit coupling effect, providing more triplet-state energy levels and improving the external quantum efficiency and the like, and has obvious advantages when used as a near-infrared organic electroluminescent materials; and the prepared near-infrared organic electroluminescent devices show remarkable photoelectric conversion efficiency.

Description

technical field [0001] The present invention relates to an electroluminescent material, in particular to a class of asymmetric dinuclear cyclometal platinum (II) complex structure containing a D-A-A configuration π-conjugated system and its application in near-infrared organic electroluminescent devices; It belongs to the field of luminescent material preparation. Background technique [0002] The emission of organic / polymer light-emitting diodes (OLED / PLED) in the near-infrared region has become a research hotspot in recent years. Based on the application of this kind of near-infrared luminescent materials, there are many applications and prospects in military and medical fields such as communication, display, and biological imaging (“Ran Tao, Juan Qiao, Guoliang Zhang, Lian Duan, Liduo Wang, and Yong Qiu. J. Phys. Chem.C.2012,116,11658.","Cheuk-Lam Ho, Bing Yao, Baohua Zhang, Ka-Leung Wong, Wai-Yeung Wong, Zhiyuen Xie, Lixiang Wang, Zhenyang Lin. Journal of Organometallic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0086C09K2211/185H10K85/346H10K50/11
Inventor 刘煜郝昭然朱卫国王亚飞谭华
Owner XIANGTAN UNIV
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