Tetravalent metal platinum complex containing tetradentate ligand, preparation method, application and device

A tetravalent metal, tetradentate ligand technology, applied in the direction of electric solid devices, semiconductor devices, platinum group organic compounds, etc., can solve the problem of poor stability, tetravalent cyclic metal platinum (IV) metal complex phosphorescent materials research reports are rare And other issues

Active Publication Date: 2019-04-12
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Although there have been many reports on bivalent cyclometallic platinum(II) metal complex phosphorescent materials in the literature, there are very few reports on tetravalent cyclometallic platinum(IV) metal complex phosphorescent materials.
However, the metal ion in the center of the platinum (II) complex has an unsaturated 16-electron structure, and there is still an uncoordinated 6p orbital, which is easily affected by electron donors or electron-rich substances in the surrounding environment. It is stable as a phosphorescent material. poor sex

Method used

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  • Tetravalent metal platinum complex containing tetradentate ligand, preparation method, application and device
  • Tetravalent metal platinum complex containing tetradentate ligand, preparation method, application and device
  • Tetravalent metal platinum complex containing tetradentate ligand, preparation method, application and device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0219] The tetravalent ring metal platinum (IV) complex Pt37 containing a tetradentate ligand provided by the present invention can be synthesized as follows:

[0220]

[0221] Synthesis of intermediate 2-OMe: Add 4-bromo-1-(3-methoxybenzene)-1-hydrogen-pyrazole 1 (1200 mg, 4.74 mmol, 1.00 eq. ), 2,4,6-trimethylphenylboronic acid (1166mg, 7.11mmol, 1.50 equivalents), Pd 2 (dba) 3 (82mg, 0.09mmol, 0.02eq), tripotassium phosphate (3018mg, 14.22mmol, 3.00eq), S-Phos (156mg, 0.38mmol, 0.08eq). The nitrogen was purged three times, then, toluene (20 mL) was added. Then nitrogen was bubbled for 20 minutes, and the reaction mixture was stirred at 110° C. for 3 days. After cooling, the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, eluent (petroleum ether / ethyl acetate=20:1-10:1), to obtain 2-OMe, 1354 mg of yellow solid, yield 97%.

[0222] 1 H NMR (500MHz, DMSO-d 6 ):δ2.13(s,6H),2....

Embodiment 2

[0231] The tetravalent ring metal platinum (IV) complex Pt47 containing a tetradentate ligand provided by the present invention can be synthesized as follows:

[0232]

[0233] Synthesis of intermediate compound 3: Add 3,5-dimethyl-4-bromopyrazole (5250mg, 30.00mmol, 1.00 equivalents), cuprous iodide to a dry three-necked flask with a reflux condenser and a magnetic rotor in sequence (572mg, 3.00mmol, 0.10equivalent), L-proline (690mg, 6.00mmol, 0.20equivalent), potassium carbonate (8280mg, 60.00mmol, 2.00equivalent), nitrogen was replaced three times, and then m-iodoanisole (10500mg , 45.00mmol, 1.50eq) and redistilled dimethylsulfoxide (10mL). The reaction mixture was stirred at 120° C. for 2 days, and monitored by TLC until the reaction of the raw material 4-bromopyrazole was completed. Add water (100mL) to quench the reaction, filter, 50mL of ethyl acetate fully wash the insoluble matter, separate the organic phase in the mother liquor, dry over anhydrous sodium sulfat...

Embodiment 3

[0245] The tetravalent ring metal platinum (IV) complex Pt52 containing a tetradentate ligand provided by the present invention can be synthesized as follows:

[0246]

[0247] Synthesis of intermediate 5-OMe: Add 4-bromo-1-(3-methoxybenzene)-3,5-dimethyl-1 hydrogen-pyrazole 3 ( 4.50g, 16.01mmol, 1.00eq), 2,4,6-trimethylphenylboronic acid (5.25g, 32.02mmol, 2.00eq), Pd 2 (dba) 3(0.29g, 0.32mmol, 0.02eq), tripotassium phosphate (10.20g, 48.03mol, 3.00eq), S-Phos (0.53g, 0.60mmol, 0.08eq) were purged of nitrogen three times, then toluene (100mL) was added. Then nitrogen was bubbled for 20 minutes, and the reaction mixture was stirred at 110° C. for 3 days. Cool, add water (100 mL), extract with ethyl acetate (50 mL×3), combine organic phases, dry over anhydrous sodium sulfate, filter, and distill off the solvent under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography with eluent (petroleum ether / ethyl acetate=20:1-1...

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Abstract

The invention relates to the technical field of organic luminescent materials and provides a tetravalent metal platinum complex phosphorescent luminescent material containing a tetradentate ligand. The tetravalent metal platinum complex containing the tetradentate ligand has a structure shown in a first general formula. Meanwhile, the invention also provides a preparation method of the tetravalentmetal platinum complex containing the tetradentate ligand, an application of the tetravalent metal platinum complex containing the tetradentate ligand in an electroluminescent device and a device, the device comprises the tetravalent metal platinum complex containing the tetradentate ligand. According to the tetravalent metal platinum complex containing the tetradentate ligand, the structure of the ligand surrounding the metal center and the structure of the substituent group on the ligand are regulated and controlled to regulate and control the photophysical property of the tetradentate ringmetal platinum complex, and the tetravalent metal platinum complex has the advantage of high stability and has wide application prospect in a plurality of fields such as OLED display, illumination and the like.

Description

technical field [0001] The invention relates to the technical field of organic light-emitting materials, in particular to a tetravalent metal platinum (IV) complex containing a tetradentate ligand, a preparation method, an application and a device. Background technique [0002] Compounds capable of absorbing and / or emitting light are applicable to various optical and electroluminescent devices, including: light-absorbing devices, solar-sensitive devices and photosensitive devices, organic light-emitting diodes (Organic Light-Emitting Diode, OLED), light-emitting devices , or devices capable of both light absorption and light emission and as markers for biological applications. Much research has been devoted to the discovery and optimization of organic and organometallic materials for use in optical and electroluminescent devices. In general, research in this area aims to achieve a number of goals, including improvements in absorption and emission efficiency, and improvement...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07F15/0086C09K2211/185H10K85/346H10K50/11
Inventor 李贵杰冯琦戴健鑫赵向东陈少海佘远斌
Owner ZHEJIANG UNIV OF TECH
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