Preparation and application of N'N'C'N type tetradentate platinum (II) complex

A technology of N^N^C^N and complexes, applied in the field of phosphorescent doped materials, can solve the problems of easy aging, short service life, and restrictions on the large-scale application of OLED technology

Active Publication Date: 2020-07-07
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014]The development of OLED display technology is a arduous and significant research, which has good characteristics but also has shortcomings such as short service life, poor color purity, and easy aging , limiting the large-scale application of OLED technology

Method used

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  • Preparation and application of N'N'C'N type tetradentate platinum (II) complex
  • Preparation and application of N'N'C'N type tetradentate platinum (II) complex
  • Preparation and application of N'N'C'N type tetradentate platinum (II) complex

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Experimental program
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Effect test

preparation example Construction

[0054] The preparation method of above-mentioned complex, comprises the steps:

[0055] As shown below, carbazole derivative S1 is subjected to bromination reaction to obtain substrate S2, S2 is reacted with biboronic acid pinacol ester to obtain corresponding pinacol ester derivative S3, and S3 is obtained by Suzuki reaction with pyridine derivative S6 S7, S7 and pyridine derivatives S8 were reacted by Suzuki to obtain S9, S9 and K 2 PtCl 4 The reaction results in the target product P. Among them, S6 is prepared by Stille reaction of S4 and S5.

[0056]

Embodiment 1

[0060]

[0061] synthetic route:

[0062]

[0063] Synthesis of Compound 2: Take 11.2g (40.0mmol) of Compound 1, dissolve it in 600mL of acetic acid, then drop into 16.0g (2.5eq., 100.0mmol) of liquid bromine, and react in a light-shielding manner. After stirring at room temperature for about 4 hours, remove the solvent by rotary evaporation, then add an appropriate amount of water and sodium bisulfite solution to wash, extract with ethyl acetate, 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 to obtain 15.7 g of a white solid with a yield of 90% and a purity of 99.9%.

[0064] Synthesis of compound 6: take 14.7g (40.0mmol) compound 5, 34.0g compound 4 (3eq., 120.0mmol) and Pd (PPh 3 ) 4 924mg (0.02eq., 0.8mmol), was added to a three-necked flask, evacuated and replaced with nitrogen several times, then in...

Embodiment 2

[0069]

[0070] The synthesis route of P2 is basically the same as that of P1, and the synthesis of some compounds is shown below.

[0071]

[0072] Synthesis of compound 11: take 15.3g (40.0mmol) compound 10, 34.0g compound 4 (3eq., 120.0mmol) and Pd (PPh 3 ) 4 924mg (0.02eq., 0.8mmol), was added to a three-necked flask, evacuated and replaced with nitrogen several times, then injected with 200mL of toluene, and heated to 105°C. After reacting for 12 hours under the protection of nitrogen, cool to room temperature, quench the reaction with KF solution, add an appropriate amount of water and ethyl acetate to extract, collect the organic phase, dry over anhydrous magnesium sulfate and remove the solvent by rotary evaporation, use n-hexane / ethyl acetate System column chromatography obtained 8.4 g of white solid with a yield of 85% and a purity of 99.0%.

[0073] The synthesis of compound 12: get 10.3g (20.0mmol) compound 3, 5.0g (20.0mmol) compound 11, potassium carbona...

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Abstract

The invention relates to preparation and application of an N'N'C'N type tetradentate platinum (II) complex. The complex disclosed by the invention has a structure as shown in a formula (II). The performance of an organic light-emitting device prepared from the complex disclosed by the invention is better improved compared with that of a reference device, and the organic light-emitting device has ahigher application value on an organic light-emitting diode and can be used as a phosphorescent doped material for manufacturing an orange-red light OLED device with high luminous efficiency.

Description

technical field [0001] The invention relates to a novel N^N^C^N tetradentate platinum (II) complex metal-organic material, especially a phosphorescent doped material used in a light-emitting layer of an OLED light-emitting device for photon emission. Background technique [0002] Organic Light-Emitting Diode (OLED) was discovered in the laboratory by Chinese-American professor Ching W.Tang in 1979, because of its self-illumination, wide viewing angle, almost infinitely high contrast, relatively high The advantages of low power consumption, extremely high response speed, and potential flexibility and foldability have been widely concerned and researched. [0003] In the field of OLED materials, the development of phosphorescent OLED light-emitting layer doping materials is relatively rapid and mature, which is mainly based on some heavy metal organic complexes, such as iridium, platinum, europium, osmium, etc. Phosphorescent materials can make full use of the energy of singl...

Claims

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Application Information

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IPC IPC(8): C07F15/00C07D401/14C09K11/06H01L51/50H01L51/54
CPCC07F15/0086C07D401/14C09K11/06C09K2211/185H10K85/346H10K50/12H10K71/40H10K50/11H10K2101/10H10K71/12H10K71/00H01K5/00
Inventor 康健戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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