Ionic iridium complex with pyrimidine ligand and preparation method thereof

A technology of iridium complexes and pyrimidines, applied in the field of preparation of pyrimidine iridium complexes, can solve the problems of less reports of ionic complexes, poor performance, etc., to improve energy transfer efficiency, increase interaction, long life effect

Inactive Publication Date: 2014-12-03
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The electrophosphorescent materials currently studied are mainly organic heavy metal complexes such as osmium, iridium, platinum, ruthenium, etc., but most of them are limited to neutral complexes, and there are few reports on ionic complexes, and their performance is not good.

Method used

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  • Ionic iridium complex with pyrimidine ligand and preparation method thereof
  • Ionic iridium complex with pyrimidine ligand and preparation method thereof
  • Ionic iridium complex with pyrimidine ligand and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0042] Synthesis of 2-(2,4-difluorophenyl)pyrimidine (DFPPM)

[0043] Weigh 3.996g (25mmol) 4,6-dimethyl-2-chloropyrimidine, 4.7453g (30mmol) 2,4-difluorophenylboronic acid, 0.6794g (2.5mmol) triphenylphosphine in a 100ml three-necked flask In, add 25ml ethylene glycol dimethyl ether, 35ml potassium carbonate (9.315g) solution. Nitrogen was passed at room temperature for 30 minutes, and then 0.1427 g (0.625 mmol) of palladium acetate was added. Magnetic stirring, reflux at 118°C for 18 hours. The reaction was stopped, cooled to room temperature, the organic phase was separated, the aqueous phase was extracted with ethyl acetate (60ml*4), the combined organic phase was washed with 80ml of water and 80ml of brine, and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation, and the obtained solid was vacuum-dried at 60° C. for 12 hours. The crude product was chromatographed on a silica gel column with dichloromethane / acetone (10:1 volume ratio). ...

example 2

[0045] Synthesis of 4,6-Dimethyl-2-(2,4-difluorophenyl)pyrimidine (MDFPPM)

[0046] Weigh 2.8691g (25mmol) 2-chloropyrimidine, 4.7681g (30mmol) 2,4-difluorophenylboronic acid, 0.6794g (2.5mmol) triphenylphosphine in a 100ml three-necked flask, add 25ml ethylene glycol di Methyl ether, 35ml potassium carbonate (9.315g) solution. Nitrogen was passed at room temperature for 30 minutes, and then 0.1427 g (0.625 mmol) of palladium acetate was added. Magnetic stirring, reflux at 118°C for 18 hours. The reaction was stopped, cooled to room temperature, the organic phase was separated, the aqueous phase was extracted with ethyl acetate (60ml*4), the combined organic phase was washed with 80ml of water and 80ml of brine, and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation, and the obtained solid was vacuum-dried at 60° C. for 12 hours. The crude product was chromatographed on a silica gel column with dichloromethane / acetone (10:1 volume ratio). ...

example 3

[0048] Synthesis of 4,6-Dimethyl-2-phenylpyrimidine (MPPM)

[0049] Weigh 3.996g (25mmol) 4,6-dimethyl-2-chloropyrimidine, 3.5341g (30mmol) phenylboronic acid, 0.6794g (2.5mmol) triphenylphosphine in a 100ml three-necked flask, add 25ml ethylene di Alcohol dimethyl ether, 35ml potassium carbonate (9.315g) solution. Nitrogen was passed at room temperature for 30 minutes, and then 0.1427 g (0.625 mmol) of palladium acetate was added. Magnetic stirring, reflux at 118°C for 18 hours. The reaction was stopped, cooled to room temperature, the organic phase was separated, the aqueous phase was extracted with ethyl acetate (60ml*4), the combined organic phase was washed with 80ml of water and 80ml of brine, and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation, and the obtained solid was vacuum-dried at 60° C. for 12 hours. The crude product was chromatographed on a silica gel column with dichloromethane / acetone (10:1 volume ratio). After drying, ...

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Abstract

The invention provides an ionic iridium complex with pyrimidine ligand and a preparation method thereof. The iridium complex has a chemical formula as follows. The preparation method of the ionic iridium complex is as below: first reacting substituted 2-chloro pyrimidine or 4,6-dimethyl pyrimidine with borophenylic acid or 2, 4-difluoro borophenylic acid to prepare a ligand; reacting the ligand with a compound iridous chloride (IrCl3.3H2O) to obtain chlorine bridge; and reacting the chlorine bridge with bisglyoxaline and conducting ion exchange reaction with salt to obtain the complex. Using iridium complex with pyrimidine derivative as an electrophosphorescent material has the following characteristics: for a same device, the pyrimidine-type iridium complex device has longer service life than a 2-phenylpyridine device; and the N atom electron cloud in the complex is more prominent, so as to increase the interaction with other molecules and improve the efficiency of energy transfer.

Description

technical field [0001] The invention belongs to the field of electrophosphorescent materials, and in particular relates to a preparation method of a novel pyrimidine iridium complex. Background technique [0002] Since the 1970s when Pope et al. prepared organic electroluminescent devices with crystals for the first time, organic electrophosphorescent materials have been favored by scientists from all over the world and have developed rapidly. Electrophosphorescence is considered to be the best way to achieve high-efficiency luminescence and prolong device life because the quantum yield can reach 100%. [0003] OLEDs is a device that uses organic materials to emit light under electrical injection. It has all-solid-state, autonomous luminescence, high brightness, wide viewing angle (up to 170 degrees or more), fast response speed (about tens of nanoseconds), thin thickness, and flexible use. Substrate, low-voltage DC drive (3 ~ 10V), low power consumption, wide operating tem...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06
Inventor 韦传东葛国平李春艳
Owner NINGBO UNIV
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