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Metal complexes containing [1,2,4]triazolo[4,3-a]pyridine structural units and their applications

A structural unit, 3-a technology, applied to compounds containing elements of group 8/9/10/18 of the periodic table, palladium organic compounds, platinum-based organic compounds, etc., can solve the problems of limited metal-organic small molecules, Achieve the effect of improving the utilization rate of radiant radiation energy, high thermal stability, and suppressing rotation and vibration

Active Publication Date: 2022-07-08
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 complexes containing [1,2,4]triazolo[4,3-a]pyridine structural units and their applications
  • Metal complexes containing [1,2,4]triazolo[4,3-a]pyridine structural units and their applications
  • Metal complexes containing [1,2,4]triazolo[4,3-a]pyridine structural units and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Example 1: The platinum complex Pt1 can be synthesized as follows:

[0077]

[0078] Synthesis of intermediate 3a: Into a dry three-necked flask with a magnetic stirring rotor and a condenser tube, intermediate 1a (1.76 g, 25.20 mmol, 1.0 equiv.), intermediate 2a (5.13 g, 27.70 mmol, 1.1 equiv.) were sequentially added and then The nitrogen was purged three times, and absolute ethanol (70 mL) was added under nitrogen protection. 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 iodine element (7.66g, 30.24mmol, 1.1eq), potassium carbonate (10.45g, 75.60mmol, 3.0eq), stir in dichloromethane solution (300mL) at room temperature for 24 hours, monitor by thin layer chromatography until the reaction of the raw materials is completed . Part of the solvent was spun off under reduced pressure distillation, the concentrated reaction solution was washed three...

Embodiment 2

[0081] Example 2: The platinum complex Pt2 can be synthesized as follows:

[0082]

[0083] Synthesis of Ligand 2: Into a dry three-necked flask with a magnetic stirring rotor and a condenser tube, add Intermediate 4b (400 mg, 1.51 mmol, 1.0 equiv), Intermediate 3a (501 mg, 1.82 mmol, 1.2 equiv), iodination Cuprous (29 mg, 0.15 mmol, 10 mol %), pyridine 2-carboxylate (37 mg, 0.30 mmol, 20 mol %), potassium phosphate (802 mg, 3.78 mmol, 2.5 equiv) were then purged with nitrogen three times, and 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 completion of the reaction of the starting materials, and 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. ...

Embodiment 3

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

[0086]

[0087] Synthesis of Ligand 3: To a dry three-necked flask with a magnetic stirring rotor and a condenser tube, add Intermediate 3a (812 mg, 2.80 mmol, 1.0 equiv), Intermediate 4c (844 mg, 3.08 mmol, 1.1 equiv), iodine Cuprous (53 mg, 0.28 mmol, 10 mol%), pyridine 2-carboxylate (68 mg, 0.56 mmol, 20 mol%), potassium phosphate (1.49 g, 7.00 mmol, 2.5 equiv), then purged with nitrogen three times, under nitrogen protection DMSO (15 mL) was added at the bottom. The mixture was stirred and reacted in an oil bath at 120°C for 24 hours, monitored by thin layer chromatography until the completion of the reaction of the starting materials, and 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 combine...

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Abstract

The invention discloses a metal complex containing a [1,2,4]triazole[4,3-a]pyridine structural unit and its application. The invention regulates the photophysical properties of platinum (II) complexes containing [1,2,4]triazolo[4,3-a]pyridine structural units by adjusting the structure of the substituents on the ligands. ) complexes have the advantages of high quantum efficiency and good thermal stability, and have broad application prospects in many fields such as OLED display and lighting. ,4] The regulation of the photophysical properties of the palladium(II) complex of the triazolo[4,3-a]pyridine structural unit, so that the delayed fluorescence emission of the palladium(II) complex can be realized. The complexes also have long excited triplet lifetimes and can be used as OLED light-emitting materials or excited-state sensitization materials.

Description

technical field [0001] The present invention relates to the technical field of organic light-emitting materials, in particular to metal complexes containing [1,2,4]triazolo[4,3-a]pyridine structural units and applications thereof. 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 Electroluminescent Device). Organic electroluminescence refers to a luminescence phenomenon in which small organic molecules, metal-organic complex molecules or polymer molecular luminescent materials directly convert electrical energy into light energy under the action of a forward biased electric field. OLED is an autonomous light-emitting device without a backlight. It has the characteristics of fast response speed, low driving voltage, high luminous efficiency and resolution, high contrast, and wide viewing angle. In a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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