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Iptycene pyridazine tetradentate platinum complex phosphorescent material, preparation method and application thereof

A technology of platinum complexes and phosphorescent materials, which is applied in the direction of luminescent materials, platinum group organic compounds, platinum organic compounds, etc., can solve the problems of limited stability and wide application of OLEDs, reduce non-radiative transitions, and improve color purity , Improve the effect of luminous performance

Active Publication Date: 2020-03-06
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Iptycene pyridazine tetradentate platinum complex phosphorescent material, preparation method and application thereof
  • Iptycene pyridazine tetradentate platinum complex phosphorescent material, preparation method and application thereof
  • Iptycene pyridazine tetradentate platinum complex phosphorescent material, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1, the preparation of intermediate 9,10-dihydro-9,10-diethylanthracene-11,12-anhydride dda

[0049] Anthracene (7.5g, 42mmol) and dimethyl butynedioate (DMAD, 7.5mL, 61mmol) were put into a reaction flask, reacted at 170°C for 45min, then raised the temperature to 180°C for another 5min. After the reaction, the mixture was cooled and recrystallized with methanol to obtain 12.2 g of white solid 9,10-dihydro-9,10-diethylanthracene-11,12-dicarboxylate methyl ddcme with a yield of 90%. The above product ddcme was dissolved in NaOH (4.0g, 100mmol), methanol (50mL, 1237mmol) and water (15mL, 833mmol) were added, refluxed for 1 hour, cooled and placed at -20°C overnight. Crystals formed, dissolved in water, adjusted pH to below 5 with 1 mol / L dilute hydrochloric acid solution, precipitated, filtered and dried to obtain 10 g of white solid 9,10-dihydro-9,10-diethylanthracene- 11,12-dicarboxylic acid ddca, yield 89%. Then take ddca (10g, 34mmol) and sodium acetate (...

Embodiment 2

[0051] Embodiment 2, preparation of pterene-modified intermediate hydrazide ddah and dichloropyridazine compound ddcp

[0052] Weigh 9,10-dihydro-9,10-diethylanthracene-11,12-anhydride dda (6.5g, 23mmol) into a reaction flask, pour (20mL, 350mmol) glacial acetic acid, and stir to reflux. After the solid was dissolved, hydrazine hydrate (3.5 g, 70 mmol) was added dropwise and reacted at 125° C. for 3 h. Cool, filter with suction, wash the product with ethanol, and dry to obtain 6 g of pterene-modified intermediate hydrazide ddah, with a yield of 90%. Put ddah (6.0g, 21mmol) into the reaction flask, evacuate, replace with nitrogen repeatedly at least three times, add 1,2-dichloroethane (20mL, 249mmol), add phosphorus oxychloride (16mL, 172mmol), in Reaction at 125°C for 8h. Spin dry 1,2-dichloroethane and phosphorus oxychloride in a vacuum, pour the product into ice water, adjust the pH to neutral with sodium hydroxide solution, precipitate a solid, filter it with suction, and...

Embodiment 3

[0054] Example 3, Preparation of 2,6-dimethylphenoxypyridazine Iddp modified by ligand pterene

[0055] Put pterene-modified dichloropyridazine ddcp (1.71g, 5mmol), 2,6-dimethylphenol (0.49g, 4mmol), potassium carbonate (1.38g, 10mmol) into the reaction bottle, vacuumize and fill Nitrogen was repeatedly replaced at least three times; 10 mL of DMF after deoxygenation by blowing nitrogen was added, and stirred under reflux at 120° C. for 24 h. After the reaction, extract with dichloromethane, add anhydrous sodium sulfate to dry, suction filter, column chromatography, use V PE :V EA =5:1 Developing agent chromatographic separation, 1.38 g of white solid was obtained, and the yield was 84%. 1 H NMR (400MHz, 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 an iptycene pyridazine tetradentate platinum complex phosphorescent material, a preparation method and application thereof. The oxygen atom bridged pyridazine tetradentate platinum complex based on iptycene modification has a structural general formula shown as formula (I). According to the tetradentate phosphorescent platinum complex disclosed by the invention, a rigid non-conjugated three-dimensional iptycene structure wrapping a platinum core is introduced into a ligand, a concentration quenching effect caused by intermolecular accumulation is effectively inhibited,and the luminous efficiency and color purity of the platinum complex phosphorescent material are improved to the greatest extent. The preparation method and the obtained pyridazine tetradentate platinum complex based on iptycene modification have high internal and external quantum yield, luminance and stability. A luminescent layer of an electroluminescent device provided by the invention is prepared by spin-coating film making based on the iptycene-modified pyridazine tetradentate platinum complex under specific conditions, the cost is low, the operation is simple, the chemical properties arestable, and the light-emitting brightness and efficiency are high, thus being conducive to realizing efficient electroluminescent devices.

Description

technical field [0001] The invention relates to the technical field of electroluminescence, in particular to a pterene pyridazine tetradentate platinum complex phosphorescent material and its preparation method and application, especially to a class of pterene modification based on a large three-dimensional structure Pyridazine tetradentate platinum complex phosphorescent materials and their organic electroluminescent devices. Background technique [0002] In the past two decades, organic light-emitting diodes (OLEDs) have developed rapidly in the field of next-generation lighting and display technologies, and thus have attracted great attention in both academia and industry. Due to the advantages of self-illumination, large color gamut, high contrast ratio, and large viewing angle, displays using high-efficiency phosphorescent OLEDs are the second largest displays in the mobile phone display industry, second only to liquid crystal displays. However, the limited stability o...

Claims

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Application Information

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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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