Synthesis and application of dinuclear ring metal platinum (II) complex near-infrared electrophosphorescent material containing different conjugated bridges

A technology of cyclometals and complexes, which is applied in the direction of luminescent materials, compounds containing elements of group 8/9/10/18 of the periodic table, platinum group organic compounds, etc. Weak effect, affecting luminous efficiency and other issues, to achieve the effect of enhancing external quantum efficiency, broadening energy level delocalization, and reducing non-radiative transition rate

Inactive Publication Date: 2017-11-28
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantage of such platinum complexes is that as the current density increases, the EQE of the device will suffer a serious roll-off (roll-off), which is consistent with the large planar structure of such complexes, which is easy to form molecular stacking and produce triplets. state-triplet annihilation, it is difficult to meet the universal applicability of materials
In addition, 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 metal orbitals and molecular orbitals is relatively weak, It is easy to produce fluorescence / phosphorescence double emission, which affects the luminous efficiency

Method used

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  • Synthesis and application of dinuclear ring metal platinum (II) complex near-infrared electrophosphorescent material containing different conjugated bridges
  • Synthesis and application of dinuclear ring metal platinum (II) complex near-infrared electrophosphorescent material containing different conjugated bridges
  • Synthesis and application of dinuclear ring metal platinum (II) complex near-infrared electrophosphorescent material containing different conjugated bridges

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Cyclometallic Platinum Complex IQBIQ[Pt(DPM)] 2 、IQDFBIQ[Pt(DPM)] 2 and PyrBIQ[Pt(DPM)] 2 The preparation route of is as follows.

[0056]

[0057] (1) Synthesis of intermediate 1

[0058] Add compound 1,4-dibromobenzene (5g, 21.37mmol), bipinacol borate (13.56g, 53.42mmol), potassium acetate (12.58g, 128.22mmol), Pd(dppf ) Cl 2 (781mg, 1.069mmol) and 1,4-dioxane (40mL), under the protection of nitrogen, the temperature was raised to 80°C and the reaction was refluxed for 24h. The reaction was stopped, cooled, the reaction solution was washed 4 times with saturated brine, extracted 2 times with DCM, the combined organic phases were washed with anhydrous MgSO 4 Dry overnight, filter, and spin off the organic solvent. The crude product is separated by column chromatography using PE-DCM (v / v, 2 / 1) as the eluent, and then recrystallized from n-hexane to obtain 4.8 g of white needle-like crystals. Yield: 68.5%. 1 H NMR (400MHz, CDCl 3 ,TMS),δ(ppm):7.80(s,1H),1.35(...

Embodiment 2

[0079] Structural characterization of near-infrared electrophosphorescent materials of dinuclear cyclometal platinum(II) complexes with different conjugated bridges, and their photoelectric physical, electrochemical, thermodynamic properties and luminescence performance tests.

[0080] Symmetrical Binuclear Cyclometallic Platinum(II) Complexes with A-D-A Configuration 1 H NMR, 13 C NMR spectrum was measured by BrukerDex-400NMR instrument; mass spectrum was tested by Bruker Bifiex MALDI-TOF mass spectrometer; thermogravimetric analysis was carried out by thermal analyzer model Perking-El TGA at 10 °C min -1 Tested at the heating rate; cyclic voltammetry (CV) adopts the electrochemical workstation model HP-CHI660A, under the protection of nitrogen, with a three-electrode system test (Pt sheet as the working electrode, Pt wire as the reference electrode, Ag / AgCl For the reference electrode, 0.1M Bu 4 NPF 6 Acetonitrile solution is electrolyte); UV-visible absorption spectrum i...

Embodiment 3

[0093] Photophysical and Thermodynamic Properties of Symmetrical Binuclear Cyclometallic Platinum Complexes with Different Conjugated Bridges

[0094] figure 1 , Figure 6 and Figure 11 They are binuclear cyclometal platinum complexes IQBIQ[Pt(DPM)] 2 、IQBIQ[Pt(DPM)] 2 and PyrBIQ[Pt(DPM)] 2 The ultraviolet-visible (UV-vis) absorption spectrogram in DCM solution, specific data are shown in Table 1. The strong absorption band located in the 240-390nm interval belongs to the spin-allowed π-π* transition centered on the main ligand (LC), and the low-energy band absorption peak at 350-600nm belongs to the ligand-centered spin-forbidden ( 3 LC) electron transition, metal to ligand ( 3 MLCT) charge transfer.

[0095] figure 2 , Figure 7 and Figure 12 They are binuclear cyclometal platinum complexes IQBIQ[Pt(DPM)] 2 、IQBIQ[Pt(DPM)] 2 and PyrBIQ[Pt(DPM)] 2 The photoluminescence spectrum in DCM solution, the specific data are shown in Table 1. The study found that IQBI...

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Abstract

The invention discloses a dinuclear ring metal platinum (II) complex near-infrared electrophosphorescent material containing different conjugated bridges, and application of the electrophosphorescent material to an organic electroluminescent diode. The dinuclear ring metal platinum complex near-infrared electrophosphorescent material uses different conjugated rigid structures (benzene, 1,4-difluorobenzene, carbazole, fluorene and pyrene) as luminous kernel donor (D) units, and uses nitrogen-containing dentate conjugate ligands (isoquinoline, anthraquinoline and phenanthridine) as receptor (A) units for building the ring metal platinum complex near-infrared electrophosphorescent material using A-D-A structure as a main ligand, using 2,2,6,6-tetramethyl-3,5-heptadione as an auxiliary ligand and using platinum ions. The organic electrophosphorescent luminous device is prepared by using the near-infrared electrophosphorescent material as a luminous layer doping agent and using m-MTDATA:CBP as a body material. The device is a near-infrared electrophosphorescent luminous device with the maximum emitting peak being 709nm, the outer quantum efficiency being 3.97 percent and the maximum radiation degree being 2354nW.Sr<-1>.cm<-2>.

Description

technical field [0001] The invention relates to the field of near-infrared luminescent materials of cyclometal platinum (II) complexes, in particular to the synthesis and application of a class of binuclear cyclometal platinum (II) complex near-infrared electroluminescent materials containing different conjugated bridges. technical background [0002] Since the near-infrared region involves applications in important fields such as data storage, security marking, photodynamic therapy, biological detection, and optical fiber communication, especially military applications such as infrared detection and infrared guidance, the light-emitting devices based on organic materials Wavelength advancement into the near-infrared region is both significant and technically challenging. In the exploration of near-infrared organic electroluminescent devices, finding and preparing organic materials with near-infrared luminescent activity is the cornerstone and the root [1-4] . At present, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0086C09K2211/185H10K85/346H10K50/12
Inventor 刘煜刘亚军朱卫国王亚飞
Owner CHANGZHOU UNIV
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