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Metal complex containing [1,2,4] triazole[4,3-a] pyridine structure unit and application

A technology of structural units and complexes, which can be applied to compounds containing elements of Group 8/9/10/18 of the periodic table, palladium organic compounds, platinum organic compounds, etc. The effect of improving energy utilization, improving rigidity, and high thermal stability

Active Publication Date: 2019-09-17
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Although metal-organic small molecule phosphorescent materials have made great progress, so far, the metal-organic small molecules that can meet the commercial needs are still extremely limited, so the development of new light-emitting materials is still of great significance

Method used

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  • Metal complex containing [1,2,4] triazole[4,3-a] pyridine structure unit and application
  • Metal complex containing [1,2,4] triazole[4,3-a] pyridine structure unit and application
  • Metal complex containing [1,2,4] triazole[4,3-a] pyridine structure unit and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Embodiment 1: Platinum complex Pt1 can be synthesized according to the following route:

[0077]

[0078] Synthesis of Intermediate 3a: Add Intermediate 1a (1.76g, 25.20mmol, 1.0eq), Intermediate 2a (5.13g, 27.70mmol, 1.1eq) to a dry three-necked flask with a magnetic stirring rotor and a condenser tube, and then The nitrogen was replaced three times, and absolute ethanol (70 mL) was added under the protection of nitrogen. The mixture was stirred and reacted in an oil bath at 80° C. for 24 hours, cooled to room temperature, and the solvent was distilled off under reduced pressure. Then add elemental iodine (7.66g, 30.24mmol, 1.1 equivalents), potassium carbonate (10.45g, 75.60mmol, 3.0 equivalents), stir at room temperature in dichloromethane solution (300mL) for 24 hours, and monitor by thin-layer chromatography until the reaction of the raw materials is complete . Part of the solvent was spun off under reduced pressure distillation, the concentrated reaction solu...

Embodiment 2

[0081] Embodiment 2: Platinum complex Pt2 can be synthesized according to the following route:

[0082]

[0083] Synthesis of Ligand 2: Add intermediate 4b (400mg, 1.51mmol, 1.0eq), intermediate 3a (501mg, 1.82mmol, 1.2eq), and iodide Cuprous (29mg, 0.15mmol, 10mol%), 2-pyridine formic acid (37mg, 0.30mmol, 20mol%), potassium phosphate (802mg, 3.78mmol, 2.5 equivalents) then pumped nitrogen three times, and added DMSO ( 10mL). The mixture was stirred and reacted in an oil bath at 120°C for 24 hours, monitored by thin-layer chromatography until the reaction of the raw materials was completed, and then cooled to room temperature. A small amount of brine was added and extracted with ethyl acetate. The organic layer was washed twice with water, and the aqueous layer was extracted twice with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The obtained crude product was ...

Embodiment 3

[0085] Embodiment 3. Platinum complex Pt3 can be synthesized according to the following route:

[0086]

[0087] Synthesis of Ligand 3: Add intermediate 3a (812mg, 2.80mmol, 1.0eq), intermediate 4c (844mg, 3.08mmol, 1.1eq), iodine to a dry three-necked flask with a magnetic stirring rotor and a condenser Cuprous chloride (53mg, 0.28mmol, 10mol%), 2-formic acid pyridinium (68mg, 0.56mmol, 20mol%), potassium phosphate (1.49g, 7.00mmol, 2.5 equivalents), then pumped nitrogen three times, under nitrogen protection DMSO (15 mL) was added thereafter. The mixture was stirred and reacted in an oil bath at 120°C for 24 hours, monitored by thin-layer chromatography until the reaction of the raw materials was completed, and then cooled to room temperature. A small amount of brine was added and extracted with ethyl acetate. The organic layer was washed twice with water, and the aqueous layer was extracted twice with ethyl acetate. The organic phases were combined, dried over anhydro...

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Abstract

The invention discloses a metal complex containing [1,2,4] triazole[4,3-a] pyridine structure unit and application. The photophysical property of a platinum (II) complex containing the [1,2,4] triazole[4,3-a] pyridine structure unit is regulated and controlled by regulating substituent groups on the ligand; the platinum (II) complex has the advantages of high quantum efficiency and high heat stability; wide application prospects are realized in various fields of OLED display, illumination and the like. The structure and position of substituent groups on the ligand are regulated, so that the regulation and control of the platinum (II) complex containing the [1,2,4] triazole[4,3-a] pyridine structure unit is realized, so that the delayed fluorescence emission of the platinum (II) complex can be realized; in addition, the platinum (II) complex also has a long excited triplet state service life and can be used as an OLED luminescent material or an excited state sensitized material.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to metal complexes containing [1,2,4]triazol[4,3-a]pyridine structural units and their applications. Background technique [0002] OLED is an Organic Light-Emitting Diode (Organic Light-Emitting Diode) or an Organic Light-Emitting Device (Organic Light-Emitting Device), also known as an Organic Electroluminescent Device. Organic electroluminescence refers to a luminescence phenomenon in which small organic molecules, metal-organic complex molecules or polymer molecular light-emitting materials directly convert electrical energy into light energy under the action of a forward bias electric field. OLED is an autonomous light-emitting device without a backlight. It has the characteristics of fast response, low driving voltage, high luminous efficiency and resolution, high contrast, and wide viewing angle. In addition, it can use cheap glass, metal or even flexible...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC07F15/0086C07F15/006C09K11/06C09K2211/185H10K85/341H10K85/346H10K50/121Y02E10/549
Inventor 李贵杰陈启东郑建兵佘远斌陈少海
Owner ZHEJIANG UNIV OF TECH
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