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Pterene pyridazine tetradentate platinum complex phosphorescent material and its preparation method and application

A technology of platinum complexes and phosphorescent materials, applied in luminescent materials, platinum-based organic compounds, platinum-group organic compounds, etc., can solve the problems of limiting wide application and limited stability of OLEDs, and achieve improved color purity and reduced non-radiative transitions , Inhibit the effect of π-π stacking

Active Publication Date: 2022-02-01
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the limited stability of OLEDs, especially the development of blue OLEDs remains a challenge, which limits their widespread application in consumer electronics

Method used

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  • Pterene pyridazine tetradentate platinum complex phosphorescent material and its preparation method and application
  • Pterene pyridazine tetradentate platinum complex phosphorescent material and its preparation method and application
  • Pterene pyridazine tetradentate platinum complex phosphorescent material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1 Preparation of Intermediate 9,10-Dihydro-9,10-Diethyl Antholic-11,12-Acid Anhydride DDA

[0049] The anthracene (7.5 g, 42 mmol) and butyridate (DMAD, 7.5 mL, 61 mmol) were placed in the reaction bottle, reacted at 170 ° C for 45min, then warmed to 180 ° C for 5 min. After the reaction was completed, the mixture was cooled, recrystallized with methanol, and 12.2 g of a white solid 9,10-dihydro-9,10-diethylntylene-11, 12-dicarboxylate DDCME was obtained, and the yield was 90%. The above-mentioned product DDCME was dissolved in sodium hydroxide (4.0 g, 100 mmol), methanol (50 mL, 1233 mmol), water (15 mL, 833 mmol), reflux for 1 hour, and then placed at -20 ° C overnight. There is crystal, dissolved in water, adjusting pH to 5 or less with 1 mole / liter dilute hydrochloric acid solution, precipitated, filtrate dried to give 10 g of white solid 9,10-dihydro-9,10-diethyl anthantant 11, 12-dicarboxylic acid DDCA, yield is 89%. DDCA (10 g, 34 mmol) and sodium acetate (...

Embodiment 2

[0051] Example 2, Preparation of DDCP DDAH and Dichlorozine Compound DDCP

[0052] Taking 9,10-dihydro-9,10-diethylhrane-11, 12-acid anhydride DDA (6.5 g, 23 mmol) to the reaction bottle, poured (20 mL, 350 mmol) glacial acetic acid, stirred back. After the solid dissolution, hydrazine (3.5 g, 70 mmol) was added dropwise, and the reaction was reacted at 125 ° C for 3 h. Cooling, filtration, washed with ethanol, dried to give 6 g of a butterofene modified intermediate hydrazide DDAH, yield 90%. DDAH (6.0 g, 21 mmol) was placed in the reaction bottle, evacuated, and the filled charge was repeatedly replaced, 1,2-dichloroethane (20 mL, 249 mmol) was added, and trichlorochlorophos (16 ml, 172 mmol) was added. The reaction was reacted at 125 ° C for 8 h. Vacuum ol drying 1,2-dichloroethane and trichlorophosphorus, poured the product into ice water, adjusted pH to neutral, precipitated with sodium hydroxide solution, precipitated solid, filtered, and dichloromethane obtained Dissolve, d...

Embodiment 3

[0054] Example 3, Preparation of 2,6-dimethylphenoxazine Iddp in ligand butteritis modified

[0055] Popular dichlorozine DDCP (1.71 g, 5 mmol), 2,6-dimethylphenol (0.49 g, 4 mmol), potassium carbonate (1.38g, 10 mmol), add the reaction bottle, vacuum, charge Nitrogen was repeatedly replaced at least three times; DMF after 10 ml of anthracene gas was added, and stirred at 120 ° C for 24 h. After completion of the reaction, extract with dichloromethane, dried over anhydrous sodium sulfate, filtration, column chromatography, with V PE : V EA = 5: 1 Anchor chromatography was separated to give a white solid 1.38 g, and the yield was 84%. 1 H NMR (400 MHz, DMSO) δ = 7.73-7.60 (m, 4H), 7.19-7.08 (m, 7H), 6.32 (S, 1H), 6.10 (S, 1H), 1.97 (S, 6H).

[0056]

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Abstract

The invention discloses a pterene pyridazine tetradentate platinum complex phosphorescent material and its preparation method and application. The pterene-based pyridazine tetradentate platinum complex bridged by oxygen atoms has a general structural formula: Formula (I) represents. The tetradentate phosphorescent platinum complex of the present invention effectively suppresses the concentration quenching effect caused by intermolecular accumulation by introducing a rigid non-conjugated stereophenene structure that wraps the platinum nucleus on the ligand, and improves the platinum concentration to the greatest extent. Luminous efficiency and color purity of complex phosphorescent materials. The preparation method and the obtained pterene-modified pyridazine tetradentate platinum complex have high internal and external quantum yields, luminous brightness and stability. In the electroluminescence device of the present invention, the light-emitting layer is based on the pterene-modified pyridazine tetradentate platinum complex, which is prepared by a spin-coating film-forming method under specific conditions, and has low cost, simple operation, stable chemical properties, and luminescence. High brightness and efficiency contribute to the realization of highly efficient electroluminescent devices.

Description

Technical field [0001] The present invention relates to the field of electroluminescent techniques, and in particular to a pyridic material and preparation method and application thereof, in particular, involving a class of butterolere modifications based on large spatial stereostructures. The pyrazine-based tetralatin complex phosphorescent material and its organic electroluminescent device. Background technique [0002] In the past two decades, organic lighting diodes (OLED) have developed rapidly in the field of next-generation lighting and display technology, so great attention has caused great attention in academia and industrial communities. Due to the advantages of self-illuminating, large color gamut, high contrast, high viewing angle, using high-efficiency phosphorescent OLED display is the second largest display of the ship's display industry, second only to the liquid crystal display. However, OLED has limited stability, especially the development of Blu-ray OLEDs is s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D237/26C07F15/00C09K11/06H01L51/50H01L51/54
CPCC07D237/26C07F15/0086C09K11/06C09K2211/185H10K85/346H10K50/11
Inventor 梅群波封雯雅童碧海刘磊许文娟叶尚辉杨九昌
Owner NANJING UNIV OF POSTS & TELECOMM
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