D-A type aromatic ring conjugated dendritic ring metal iridium complex and application thereof

An iridium complex, D-A technology, applied in indium organic compounds, platinum group organic compounds, compounds containing elements of group 8/9/10/18 of the periodic table, etc., can solve the problem of less types of near-infrared electroluminescent materials, etc. It can reduce the dipole-induced intermolecular interaction, increase the distance, and improve the hole transport performance.

Active Publication Date: 2020-07-17
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far, the types of near-infrared electroluminescent materials of cyclometallic iridium(III) complexes are still relatively small, and the EQE of their devices is still lower than that of red, green, and blue trichromatic cyclometallic iridium(III) complexes. Devices and near-infrared electroluminescent devices of cyclometal platinum(II) complexes

Method used

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  • D-A type aromatic ring conjugated dendritic ring metal iridium complex and application thereof
  • D-A type aromatic ring conjugated dendritic ring metal iridium complex and application thereof
  • D-A type aromatic ring conjugated dendritic ring metal iridium complex and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] D-A Cyclometallic Iridium Complex with N,N-Diphenylamine as Dendritic Unit ((DPA) 2 -TPA-BTz-Iq) 2The preparation of Irpic, the synthetic route is as follows (the raw material 4′,4′-bis(N,N-diphenylamino)-4-bromotriphenylamine CAS: 105389-36-4, purchased from Zhengzhou Alpha Chemical Co., Ltd.) :

[0035]

[0036] Preparation of Compound 1

[0037] In a 100mL single-necked flask, add 272mg (0.41mmol) 4′,4′-bis(N,N-diphenylamino)-4-bromotriphenylamine, 208mg (0.82mmol) pinacol diborate, 161mg (1.64mmol) potassium acetate (KOAc), 7mg (0.01mmol) [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, 50mL 1,4-dioxane, extracted Vacuum N 2 Under protection, the temperature was controlled at 80°C for 24 hours. Stop the reaction, after cooling to room temperature, pour the reaction solution into 100mL distilled water, extract with DCM (3×30mL), and wash the organic layer with anhydrous MgSO 4 Dry for 6h. After filtration, the solvent was distilled off under redu...

Embodiment 2

[0049] The present invention also provides the characterization and photophysical and electrochemical performance tests of the involved D-A aromatic ring conjugated dendritic ring metal iridium complex:

[0050] Nuclear magnetic resonance (NMR) spectra were recorded at 298K on a Bruker DRX 500 spectrometer in deuterated chloroform or deuterated acetone solutions with tetramethylsilane as an internal standard. Time-of-flight mass spectrometry measurements were performed on a Bruker Bifiex III MALDI-TOF. UV-Vis absorption and photoluminescence spectra were measured using a Varian Cray 50 absorption spectrometer and a Perkin-Elmer LS50B luminescence spectrometer. Cyclic voltammetry (CV) was performed on a CHI 600E electrochemical workstation at room temperature and under argon at 100mV·S -1 The scan rate is carried out, the electrolyte solution is n-Bu 4 NPF 6 (0.1M) acetonitrile solution; Pt sheet, Pt wire and Ag / AgCl electrode were used as working electrodes respectively; fo...

Embodiment 3

[0052] Complex ((DPA) 2 -TPA-BTz-Iq) 2 UV-Vis Absorption Spectrum of Irpic

[0053] The complex ((DPA) 2 -TPA-BTz-Iq) 2 Irpic was dissolved in dichloromethane to make 10 -5 M solution or prepared as a solid film, test its UV-Vis absorption spectrum. figure 1 For the complex ((DPA) 2 -TPA-BTz-Iq) 2 UV-Vis absorption spectra of Irpic in dichloromethane (DCM) solution and solid film. Depend on figure 1 It can be seen that the complex ((DPA) 2 -TPA-BTz-Iq) 2Irpic shows similar and strong UV-visible absorption peaks in dichloromethane solution and solid film. The absorption peaks are located at 318nm, 473nm, and 543nm in dichloromethane solution, and the absorption peaks are located at 318nm, 481nm, and 553nm in solid film. The absorption peak of the iridium complex at 290-350nm is assigned to π-π * Electronic transition absorption; the absorption peak at 450-550nm is attributed to metal-ligand charge transfer transition (MLCT) absorption; in addition, the absorption pea...

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Abstract

The invention discloses a D-A type aromatic ring conjugated dendritic ring metal iridium complex and a preparation method and application thereof; a dendritic unit is helpful for improving the efficiency of an electroluminescent material device, but a report that the dendritic unit and a D-A unit exist in a ring metal iridium complex near-infrared luminescent material at the same time does not exist at present. The D-A type aromatic ring conjugated dendritic ring metal iridium complex takes N,N-diphenylamine or 3,6-di-tert-butyl carbazole with good hole transport performance as a dendritic unit, takes triphenylamine-benzotriazole-isoquinoline / quinoline with a D-A structure as a main ligand, and takes 2-picolinic acid as an auxiliary ligand. The D-A type aromatic ring conjugated dendritic ring metal iridium complex is used as a luminescent layer dopant to prepare an organic electroluminescent device, so that the maximum external quantum efficiency of the device in a near-infrared regionis greatly improved, and the performance of the organic near-infrared electroluminescent device is obviously improved.

Description

technical field [0001] The invention relates to a class of D-A type aromatic ring conjugated dendritic ring metal iridium complexes and applications thereof. The aromatic ring conjugated structure N,N-diphenylamine or 3,6-di-tert-butyl carbazole or dendritic unit , with triphenylamine-benzotriazole-isoquinoline / quinoline having a donor-acceptor (D-A) structure as the main ligand, and 2-pyridinecarboxylic acid as an auxiliary ligand. The iridium complex of the ring metal belongs to the The field of electroluminescent materials and devices. Background technique [0002] Organic light-emitting diodes (OLEDs) have been widely used and developed in the field of lighting and display technology in the past decade, which largely depends on OLED displays generally superior in brightness, wide-angle visibility, contrast, response time and color purity. on other monitors [1] . With the continuous deepening of research work, researchers began to set their sights on organic near-infra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC07F15/0033C09K11/06C09K2211/185H10K85/342H10K50/12Y02E10/549
Inventor 于俊婷李茂秋谭华朱卫国
Owner CHANGZHOU UNIV
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