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Quadridentate platinum (II) complex and application

A complex, halogen technology, applied in the field of phosphorescent doping materials, can solve the problems of performance to be improved, poor stability, etc., and achieve the effect of good stability and luminescence performance

Active Publication Date: 2019-07-05
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Among them, O^N^N^O tetradentate platinum(II) complexes are mainly Schiff bases, which are relatively common but relatively poor in stability; O^N^C^O tetradentate platinum (II) The complex is relatively stable, but the performance needs to be improved

Method used

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  • Quadridentate platinum (II) complex and application
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  • Quadridentate platinum (II) complex and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] synthetic route:

[0057]

[0058] Synthesis of compound 2: Take 6.50g (20.0mmol) of compound 1, 12.70g (2.5eq., 50.0mmol) of biboronic acid pinacol ester, 5.18g (2.5eq., 50.0mmol) of potassium carbonate and Pd(dppf)Cl 2 292mg (0.02eq., 0.4 mmol), was added to a three-necked flask, evacuated and replaced with nitrogen several times, then injected with 150mL of acetonitrile-dioxane, and heated to 85°C. After reacting for 12 hours under the protection of nitrogen, cool to room temperature, remove the solvent by rotary evaporation, add an appropriate amount of water and ethyl acetate for extraction, collect the organic phase, dry it over anhydrous magnesium sulfate, add an appropriate amount of silica gel, remove the solvent by rotary evaporation, and use n-hexane / Ethyl acetate system column chromatography gave 7.12 g of white solid with a yield of 85% and a purity of 99.0%.

[0059] Synthesis of compound 3: get 11.85g (50.0mmol) compound 2,6-dibromopyrid...

Embodiment 2

[0065]

[0066] synthetic route:

[0067]

[0068] Synthesis of Compound 7: Take 16.72g carbazole (0.10mol) and 655mg anhydrous aluminum trichloride (5mmol) in a three-necked flask, vacuumize and feed nitrogen for replacement several times, then add 27.77g tert-butyl chloride dropwise (3.0eq., 0.30mmol) and 250mL of dry dichloromethane, stirred and reacted for 12hr under the protection of nitrogen, then added an appropriate amount of water for extraction, collected the organic phase, removed the solvent by rotary evaporation, and recrystallized the obtained solid with ethanol to obtain White solid 23.20g, yield 83%, purity 99.5%.

[0069] Synthesis of Compound 8: Take 13.97g (50.0mmol) of Compound 7, dissolve it in 750mL of acetic acid, then drop into 19.98g (2.5eq., 125.0mmol) of liquid bromine for light-shielding reaction. After stirring at room temperature for about 4 hours, remove the solvent by rotary evaporation, then add an appropriate amount of water and sodium ...

Embodiment 3

[0076]

[0077] synthetic route:

[0078]

[0079] The synthesis of compound 14: get 7.97g (15.0mmol) compound 9, compound 13 7.63g (1.0eq., 15.0mmol), potassium carbonate 3.45g (1.25eq., 25.0mmol) and Pd (PPh 3 ) 4 347mg (0.02eq., 0.3mmol) was added to a three-necked flask, vacuumed and replaced with nitrogen several times, then injected with 100mL of acetonitrile and 50mL of methanol, and heated to 60°C. After reacting for 12 hours under the protection of nitrogen, cool to room temperature, remove the solvent by rotary evaporation, add an appropriate amount of water and ethyl acetate for extraction, collect the organic phase, dry it over anhydrous magnesium sulfate, add an appropriate amount of silica gel, remove the solvent by rotary evaporation, and use n-hexane / Ethyl acetate system column chromatography gave 7.50 g of a white solid with a yield of 60% and a purity of 99.5%.

[0080] Synthesis of compound 15: take 6.66g (8.0mmol) of compound 14, 1.37g (1.1eq., 8....

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Abstract

The invention relates to a quadridentate platinum (II) complex and application. The complex has an N^N^N^O configuration, and a structure of the complex is as shown in a formula (3), wherein A1-A5 aresubstituted or non-substituted five-membered rings, six-membered rings and fused ring structures. The complex can be applied in the field of OLED as a phosphorescent dopant material. The platinum (II) complex has high fluorescence quantum efficiency, good thermal stability and a low quenching coefficient, and can be used for producing orange-red light OLED devices with high luminous efficiency and low roll-off.

Description

technical field [0001] The invention relates to a novel N^N^N^O tetradentate platinum (II) complex metal-organic material, especially a phosphorescent doped material used for photon emission in the light-emitting layer of an OLED light-emitting device. Background technique [0002] Organic Light-Emitting Diode (OLED, Organic Light-Emitting Diode) display technology has been widely concerned and researched for its unique properties such as low energy consumption, large viewing angle, and flexibility since its discovery. , TVs, laptops and other electronic products are gradually applied. However, compared with traditional display technologies, OLED has disadvantages such as short service life, poor color purity, and easy aging, which lead to high costs and hinder the promotion and development of OLED technology. Therefore, how to design new OLED materials is the focus and difficulty of OLED research. [0003] In the field of OLED materials, the development of phosphorescent ...

Claims

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Application Information

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IPC IPC(8): C07D401/14C09K11/06H01L51/54
CPCC07D401/14C09K11/06C09K2211/185H10K85/346H10K77/00C07F15/00C09K11/00H05B33/00
Inventor 康健戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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