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Iridium complex phosphor material taking phthalazine derivative as ligand and preparation method thereof

A technology for iridium complexes and phosphorescent materials, applied in the field of iridium complex phosphorescent materials and their preparation, can solve the problems of reducing the luminous efficiency of devices, and achieve the effects of reducing self-quenching phenomenon, improving solubility, and reducing direct effects

Inactive Publication Date: 2011-09-14
NANJING UNIV OF POSTS & TELECOMM
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Problems solved by technology

[0004] When phosphorescent materials are used as luminescent centers to prepare electroluminescent devices, due to their long excited state lifetimes, triplet-inter-triplet annihilation and triplet-polaron annihilation are prone to occur when the excited triplet concentration is high. Reduce the luminous efficiency of the device

Method used

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  • Iridium complex phosphor material taking phthalazine derivative as ligand and preparation method thereof
  • Iridium complex phosphor material taking phthalazine derivative as ligand and preparation method thereof
  • Iridium complex phosphor material taking phthalazine derivative as ligand and preparation method thereof

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preparation example Construction

[0044] The preparation method of phosphorescent iridium complex of the present invention is characterized in that comprising the following steps:

[0045]

[0046] Formula (1) Formula (2) Formula (3) Formula (4)

[0047] (1) The compound represented by Ar is dissolved in a non-polar organic solvent, and in the presence of a catalyst, undergoes a Friedel-Crafts acylation reaction with phthalic anhydride at 20-80°C, and reacts for 5h-2d to obtain a class of 2-oxobenzoic acid derivatives represented by formula (1);

[0048] (2) Dissolve 2-carbonylbenzoic acid derivatives in polar organic solvents, add hydrazine, and stir at 20-100°C for 12h-5d to obtain a class of 1-substituted phthalazine-4- ketone;

[0049] (3) Dissolve 1-substituted phthalazin-4-one in a non-polar organic solvent, and stir with a halogenating reagent at 20-90°C for 4-48 hours to obtain a class of 1-substituted- 4-halogenated phthalazine compounds;

[0050] (4) 1-substituted-4-halogenated phthalazine der...

Embodiment 1

[0066] Weigh 2.78g (21mmol) AlCl 32.31g (15.6mmol) of phthalic anhydride was placed in a two-necked flask, and 10ml (156mmol) of dichloromethane was added and stirred in an ice bath to dissolve it. Weigh 3.56g (18mmol) of N-ethyl-9H-carbazole into a one-necked bottle, add 10ml (156mmol) of dichloromethane and stir at room temperature, slowly add the above mixed solution dropwise with a separatory funnel, and continue to stir overnight at room temperature. After the reaction is completed, dilute HCl is added to the reaction solution to adjust to weak acidity, an appropriate amount of water is added, extracted with chloroform, the organic phase is washed with water, the organic phase is combined, and anhydrous MgSO 4 After drying and column purification, 2-(9-ethyl-9H-carbazole-3-carbonyl)benzoic acid was obtained.

[0067] Add 1.01g (2.9mmol) 2-(ethylcarbazole formyl)-benzoic acid in the two-necked flask, N 2 Inject 5ml (129mmol) of 80% hydrazine hydrate and 10ml (171mmol) of...

Embodiment 2

[0074] Take by weighing 1.01g (6mmol) diphenylamine and 0.31g (7mmol) 65% NaH and two-necked bottle, N 2 Inject 5ml (65mmol) of anhydrous N,N-dimethylformamide under protection, stir at room temperature for 1h, and dissolve 1.79g (5mmol) of 3-(4-chlorophthalazin-1-yl)-9-ethyl-9H- Dissolve carbazole in 5ml (65mmol) of N,N-dimethylformamide, slowly drop into the reaction flask, and continue to stir overnight at room temperature. The reaction solution was poured into a large amount of water, extracted with ethyl acetate, the organic phase was dried, concentrated, and purified by column to obtain 4-(9-ethyl-9H-carbazol-3-yl)-N,N-diphenylphthalazine -1-amine.

[0075] Weigh 0.147g (0.3mmol) 4-(9-ethyl-9H-carbazol-3-yl)-N,N-diphenylphthalazin-1-amine and 0.035g (0.1mmol) IrCl 3 ·H 2 O In a two-necked bottle, inject 1ml (55mmol) of water and 3ml (31mmol) of ethylene glycol ether, N 2 Under protection, heat up to 80°C for 24 hours, cool to room temperature, filter, wash the solid ...

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Abstract

The invention discloses an iridium complex phosphor material taking a phthalazine derivative as a ligand. The structure of the material is shown as formulas (I) and (II), wherein Ar represents aryl, substituted aryl, heterocycle aryl and substituted heterocycle aryl; R can be one of a halogen atom, alkyl, substituted alkyl, alkoxyl, aryloxy, an alkylthio group, arylthio, aromatic amino, aliphatic amino or a heterocyclic substituent; L^Y can be one of N-COOH, 8-hydroxyquinoline, beta-diketone, N^NH and the like; N^N can be bipyridyl, diquinoline, 1,10-phenanthroline, a derivative of the 1,10-phenanthroline and the like; and Z can be hexafluorophosphate and perchlorate. A dicyclic or ionic iridium complex phosphorescent electroluminescent device taking the phthalazine derivative as the ligand obtained with the preparation method has high internal and external quantum yields, high luminance and high stability. A dicyclic iridium complex is shown as a formula (I), i.e., (C^N)2Ir(L^Y); and an ionic iridium complex is shown as a formula (II), i.e., (C^N)2Ir(N^N)<+>Z<->.

Description

technical field [0001] The invention relates to a class of luminescent materials, in particular to a class of iridium complex phosphorescent materials with phthalazine derivatives as ligands and a preparation method thereof Background technique [0002] Organic electroluminescent devices have the advantages of low driving voltage, fast response speed, wide viewing angle range, and can change the luminous performance through fine-tuning of chemical structure to make rich colors, easy to achieve high resolution, light weight, and large-area flat-panel display. 21st Century Flat Panel Display Technology" has become a research hotspot in the fields of materials, information, physics and flat panel display. Among them, electrophosphorescent materials mainly based on heavy metal complexes are the most active in the current organic electroluminescence research. have d 6 and d 8 Heavy metal atoms such as platinum (Pt), iridium (Ir), and osmium (Os) in the electronic structure, du...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06
Inventor 梅群波王玲霞黄维童碧海郭远辉翁洁娜
Owner NANJING UNIV OF POSTS & TELECOMM
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