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Sterically-hindered pyrimidine iridium complex phosphorescence material and preparation method thereof

A technology of phosphorescent materials and iridium complexes, which is applied in the field of sterically hindered pyrimidine iridium complex phosphorescent materials and its preparation, can solve the problems of low purity of blue light, improve luminous efficiency, reduce red shift, increase sublimation performance and The effect of solubility

Inactive Publication Date: 2017-05-10
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] Aiming at the problem that the purity of blue light emitted by iridium complex phosphorescent materials in the prior art is not high, the present invention provides a sterically hindered pyrimidine iridium complex phosphorescent material and a preparation method thereof

Method used

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  • Sterically-hindered pyrimidine iridium complex phosphorescence material and preparation method thereof
  • Sterically-hindered pyrimidine iridium complex phosphorescence material and preparation method thereof
  • Sterically-hindered pyrimidine iridium complex phosphorescence material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] This embodiment prepares the electrophosphorescent material with the following structure:

[0080]

[0081] Bis(4-m-trimethylphenyl-6-phenylpyrimidine-N,C 2’ )(3-trifluoromethyl-5-(2'-pyridyl)-1,2,4-triazole) iridium.

[0082] A, 4-chloro-6-phenylpyrimidine synthesis;

[0083]

[0084] Weigh 2',3',4'-trisubstituted phenylboronic acid 2g (0.016mol), 4,6-dichloropyrimidine 2.45g (0.016mol), tetrakis(triphenylphosphine)palladium 0.2g and anhydrous carbonic acid Sodium 3.0g was placed in a 120mL sealed tube, and a mixed solution of 20mL tetrahydrofuran and 20mL deionized water was used as a solvent to place in the sealed tube, a stirring bar was added, and the bottle was capped. After the whole device was evacuated and replaced by nitrogen for 3 to 4 times, it was placed in an oil bath, stirred and heated on a magnetic heating stirrer to 120°C for about 8 hours. After the reaction, the closed tube was cooled to room temperature, the solution in the sealed tube was ...

Embodiment 2

[0106] This embodiment prepares the electrophosphorescent material with the following structure:

[0107]

[0108] Bis(4-m-trimethylphenyl-6-(4’-fluorophenyl)pyrimidine-N,C 5’ )(3-trifluoromethyl-5-(2'-pyridyl)-1,2,4-triazole) iridium.

[0109] Synthesis of A, 4-chloro-6-(4'-fluorophenyl) pyrimidine;

[0110]

[0111] Weigh 2g (0.014mol) of 4-fluorophenylboronic acid, 2.14g (0.0142mol) of 4,6-dichloropyrimidine, Pd(dppf)Cl 2 0.15 g and 2.5 g of anhydrous potassium carbonate were placed in a 120 mL sealed tube, and a mixed solution of 60 mL of dioxane and 20 mL of deionized water was used as a solvent to place in the sealed tube, a stirring bar was added, and the bottle was capped. After the whole device was evacuated and replaced by nitrogen for 3 to 4 times, it was placed in an oil bath, stirred and heated on a magnetic heating stirrer to 120°C for about 8 hours. After the reaction, the closed tube was cooled to room temperature, the solution in the sealed tube was p...

Embodiment 3

[0135] This embodiment prepares the electrophosphorescent material with the following structure:

[0136]

[0137] Bis(4-m-trimethylphenyl-6-(2’,4’-difluoro-phenyl)pyrimidine-N,C 5’ )(3-trifluoromethyl-5-(2'-pyridyl)-1,2,4-triazole) iridium.

[0138] Synthesis of A, 4-chloro-6-(2',4'-difluorophenyl)pyrimidine;

[0139]

[0140] Weigh 1.58g (0.1mol) of 2,4-difluorophenylboronic acid, 1.50g (slight excess of 0.1mol) of 4,6-dichloropyrimidine, 0.1g of tetrakis(triphenylphosphine)palladium and 2g of anhydrous sodium carbonate In a 120mL sealed tube, place a mixed solution of 30mL tetrahydrofuran and 20mL deionized water as a solvent in the sealed tube, add a stirring bar, and cap the bottle. After the whole device was evacuated and replaced by nitrogen for 3 to 4 times, it was placed in an oil bath, stirred and heated on a magnetic heating stirrer to 120°C for about 8 hours. After the reaction, the closed tube was cooled to room temperature, the solution in the sealed tub...

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Abstract

The invention discloses a sterically-hindered pyrimidine iridium complex phosphorescence material and a preparation method thereof and belongs to the technical field of photoelectric phosphorescence materials. The sterically-hindered pyrimidine iridium complex phosphorescence material is shown as a general molecular formula I and has more excellent photoluminescence performance. An iridium complex comprises a main ligand and an auxiliary ligand, wherein the main ligand refers to a 4,6-disubstituted pyrimidine derivative, and the auxiliary ligand refers to a triazolopyridine derivative. The sterically-hindered pyrimidine iridium complex phosphorescence material and the preparation method thereof have the advantages that an m-trimethylbenzene group with high steric hinerance effect is introduced on a pyrimidine ring for the first time and is capable of reducing intermolecular interaction but weak in influence on photoluminescence; the phosphorescence lifetime of the pyrimidine iridium complex is shorter than that of a similar pyrimidine iridium complex, so that nonradiative jump in an excited state can be reduced effectively; the iridium complex is high in photoluminescence quantum efficiency, short in phosphorescence lifetime and low in aggregated-state phosphorescence quenching, thereby being a phosphorescence material excellent in performance and wide in applicability.

Description

technical field [0001] The invention relates to the field of organic electroluminescence, in particular to a sterically hindered pyrimidine iridium complex phosphorescent material and a preparation method thereof, which comprises ligands having pyrimidine or pyrimidine derivatives. Compared with pyridine iridium complexes, these materials have Better luminous properties. Background technique [0002] At present, electronic displays are the main means suitable for the rapid transmission of information. Organic light-emitting diodes (OLEDs) have attracted great interest from researchers due to their great potential in full-color displays and flexible devices. Several OLED materials and configurations are described in US Patent Nos. 5,844,363, 6,303,238 and 5,707,745. Generally, OLEDs consist of several organic layers, the phosphorescent layer of which can be made to emit light by applying a voltage across the device (see Tang et al., Appl. Phys. Lett. 1987, 51, 913 and Burro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185C09K2211/1059C09K2211/1044C09K2211/1029H10K85/654H10K85/342H10K50/00
Inventor 童碧海何禹亨刘远远金龙左大帅王松
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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