Organic metal complex, synthesis method and organic light-emitting device thereof

An organic light-emitting device, organic metal technology, applied in the direction of organic light-emitting devices, platinum group organic compounds, platinum group organic compounds, etc., can solve problems such as poor stability and low efficiency, and achieve low efficiency, good luminous efficiency and stability. Effect

Inactive Publication Date: 2017-09-15
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The organic light-emitting device prepared by using the organometallic complex of the present invention has high luminous efficiency, stable light color, good film stability and thermal stability, and can effectively solve the problems of low efficiency and poor stability of existing organic electroluminescent devices

Method used

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  • Organic metal complex, synthesis method and organic light-emitting device thereof
  • Organic metal complex, synthesis method and organic light-emitting device thereof
  • Organic metal complex, synthesis method and organic light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] [Example 1] Synthesis of compound 8

[0058]

[0059] *Synthesis of Intermediate 8-1

[0060]Add 5-bromo-2,2'bipyridine (1.97g, 8.4mmol), (3-bromophenyl)boronic acid (1.91g, 9.5mmol), tetrakistriphenylphosphine palladium (0.36g, 0.56mmol) into the reactor ), potassium carbonate (2.78g, 20.1mmol), ethylene glycol dimethyl ether 40mL, ethanol 15mL and distilled water 15mL, stirred and refluxed at 120°C for 12h. After the reaction was completed, the reaction was stopped with distilled water, extracted with ethyl acetate, and the organic layer was extracted with MgSO 4 After drying, the solvent was distilled off under reduced pressure, followed by separation and purification by column chromatography to obtain intermediate 10-1 (2.09 g, 80%).

[0061] *Synthesis of Intermediate 8-2

[0062] Add intermediate 8-1 (3.11g, 10mmol), CuI (0.19g, 1mmol), KOH (3.37g, 60mmol), 24mL DMSO / 6mL water mixed solution into the reactor, under nitrogen protection, at 120°C Stir and ref...

Embodiment 2

[0067] [Example 2] Synthesis of compound 16

[0068]

[0069] *Synthesis of intermediate 16-1

[0070] Under nitrogen protection, palladium acetate (67.35mg, 0.3mmol), tri-tert-butylphosphine (0.243g, 1.2mmol), potassium tert-butoxide (5.39g, 48mmol), intermediate 8-1 (6.22g , 20mmol), arylamine (1.02g, 11mmol), 60mL toluene, stirred and refluxed at 130°C for 10h, cooled the reactant to room temperature, diluted with toluene, filtered through diatomaceous earth, diluted the filtrate with water, and extracted with toluene , the combined organic phases were evaporated in vacuo, and the residue was separated and purified by column chromatography to obtain intermediate 16-1 (4.54 g, 82%).

[0071] *Synthesis of Compound 16

[0072] Potassium tetrachloroplatinate (2.29g, 5.5mmol), 16-1 (2.77g, 5mmol), and 300mL ethylene glycol monoethyl ether / 100mL water mixed solution were added to the reaction vessel, and magnetically stirred at 100°C for 10h under nitrogen protection. Afte...

Embodiment 3

[0073] [Example 3] Synthesis of compound 24

[0074]

[0075] *Synthesis of intermediate 24-1

[0076] Under the protection of nitrogen, THF 60mL and intermediate 8-1 (6.22g, 20mmol) were added to the reactor. At -78°C, n-Buli (1.28g, 20mmol) was added dropwise, stirred for 0.5h, and then added with di Methyldichlorosilane (1.48g, 11.5mmol), reacted at -78°C for 18h, then raised the temperature to room temperature, diluted with distilled water after the reaction, stopped the reaction, distilled the organic layer to remove the solvent under reduced pressure, and purified it with a silica gel column Intermediate 24-1 (8.12 g, 78%) was obtained.

[0077] *Synthesis of Compound 24

[0078] Potassium tetrachloroplatinate (2.29g, 5.5mmol), 24-1 (2.6g, 5mmol), and 300mL ethylene glycol monoethyl ether / 100mL water mixed solution were added to the reaction vessel, and magnetically stirred at 100°C for 10h under nitrogen protection. After the reaction was completed, suction filter...

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Abstract

The invention discloses an organic metal complex, a synthesis method and an organic light-emitting device thereof and belongs to the technical field of organic photoelectric materials. Ligands different in Pi conjugation degree are complexed with transition metal ions, ligand groups are bridged through heteroatoms to form a novel organic metal quadridentate complex, conjugation is prolonged, planarity and rigidity of molecules are improved, directional migration of charge is facilitated, and nonradiative transition of the complex in the process of electroluminescence is lowered, so that light-emitting efficiency, thermostability and thermodynamic stability of a material are improved, and the complex can be used as a phosphorescence doping material in organic electroluminescent devices. Synthesis raw materials of the complex are conventional, and the synthesis method is simple and easy to operate. The organic light-emitting device prepared from the organic metal complex is high in light-emitting efficiency, stable in light color and high in membrane stability and thermostability.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an organic metal complex, a synthesis method and an organic light-emitting device. Background technique [0002] As a key material in OLED devices, organic light-emitting materials can be roughly divided into three categories according to the principle of light emission: traditional fluorescent materials, phosphorescent materials and thermally activated delayed fluorescence (TADF) materials. Traditional fluorescent materials can only use 25% of singlet excitons to emit light, and the luminous efficiency is low; phosphorescent materials can use 25% of singlet excitons and 75% of triplet excitons to emit light, which can theoretically reach 100% Internal quantum efficiency; typical TADF materials require that the energy difference between the singlet state and the triplet state is less than 0.1 eV. Through thermal activation, the triplet state excitons pass ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0086C09K2211/185H10K85/346H10K50/00H10K2102/301
Inventor 蔡辉董秀芹
Owner CHANGCHUN HYPERIONS TECH CO LTD
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