Phosphorescence iridium complex, preparation method and organic electroluminescent device

A technology of phosphorescent iridium complexes and complexes, applied in the fields of electric solid devices, electrical components, organic chemistry, etc., can solve the problems of reducing the luminous efficiency of devices, achieve high internal and external quantum yields, easy purification, and improve solubility effects

Inactive Publication Date: 2012-06-20
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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-triplet (T-...

Method used

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  • Phosphorescence iridium complex, preparation method and organic electroluminescent device
  • Phosphorescence iridium complex, preparation method and organic electroluminescent device
  • Phosphorescence iridium complex, preparation method and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the preparation of ligand HPQD

[0032] Weigh 4.08g (30mmol) anthranilamide and 6.24g (60mmol) NaHSO 3 Add two-neck bottle, N 2 Add 30mL of N,N-dimethylacetamide and 3.18g (30mmol) of benzaldehyde under protection, raise the temperature to 150°C and stir for 8h, after the reaction is completed, cool to room temperature, pour the reaction solution into a large amount of water, a white precipitate appears, and filter with suction , washed with water and ethanol respectively, and dried to obtain white crystals of 2-phenylquinazolin-4(3H)-one. Yiled: 97.3%. 1 H NMR (DMSO-d 6 , 400MHz) δ (ppm): 7.49-7.58 (m, 4H), 7.72-7.74 (d, 1H), 7.91-7.94 (t, 1H), 8.13-8.18 (t, 3H).

[0033] Weigh 0.47g (2.1mmol) of the above-mentioned 2-phenylquinazolin-4(3H)-one into the two-necked bottle, N 2 Inject 6mLCHCl under protection 3 and 2 mL (21 mmol, ρ=1.675) of POCl 3 , heated to 60°C and stirred for 12h, after the reaction was completed, CHCl was distilled off under re...

Embodiment 2

[0036] Embodiment 2: Complex Ir(PQD) 2 (pic) preparation

[0037] Add 0.528g (1.5mmol) IrCl to the reaction flask 3 ·3H 2 O, add 15 mL of water, then add 1.68 g (4.5 mmol) of ligand HPQD and 45 mL of ethoxyethanol, N 2 Warm up to 100°C under protection, stir for 24 hours in the dark, cool, filter, wash the solid with water and ethanol respectively, and dry to obtain the dichloro bridge compound Ir of iridium 2 (PQD) 4 Cl 2 .

[0038] With 0.7g (0.36mmol) above-mentioned dichloro bridge compound Ir 2 (PQD) 4 Cl 2 Dissolve in 30mL dichloromethane, add 0.5g (3.6mmol) potassium carbonate and 0.22g (1.8mmol) 2-pyridinecarboxylic acid (pic), N 2 React under protection at room temperature for 8 hours, concentrate to obtain the crude product, separate and purify by silica gel chromatography to obtain the red Ir(PQD) 2 (pic) solid. Yield: 68.2%. 1 HNMR (DMSO-d 6 , 400MHz) δ (ppm): 6.58-6.62 (t, 2H), 6.67-6.74 (m, 2H), 6.80-6.84 (t, 1H), 6.92-6.94 (m, 1H), 7.04-7.06 (m, 2H...

Embodiment 3

[0041] Embodiment 3: Complex Ir(PQD) 2 (dbm) preparation

[0042] Weigh 0.2g (0.103mmol) dichloro bridge compound Ir 2 (PQD) 4 Cl 2 Dissolve in 10mL dichloromethane, add 0.12g (0.52mmol) dibenzoylmethane (dbm) and 0.11g (1.03mmol) potassium carbonate, stir at room temperature for 8h, separate and purify by silica gel chromatography to obtain Ir(PQD) 2 (dbm). Yield: 33.5%. 1 H NMR (CDCl 3 , 400MHz) δ(ppm): 6.12(s, 1H), 6.60-6.62(d, 2H), 6.64-6.68(t, 2H), 6.78-6.81(t, 2H), 6.95-6.99(t, 2H) , 7.13-7.14(d, 8H), 7.18-7.24(m, 6H), 7.28-7.39(m, 16H), 7.58-7.59(d, 2H), 7.68-7.70(d, 4H), 8.36-8.39( d, 2H).

[0043]

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PUM

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Abstract

The invention discloses a phosphorescence iridium complex by taking a quinazoline derivative as a ligand and an organic electroluminescent device thereof. The structure of the phosphorescence iridium complex disclosed by the invention is represented by the formula (I) or the formula (II) described in the specification, wherein Ar represents aryl, substituted aryl, heterocyclic aryl and substituted heterocyclic aryl; R can be one of a halogen atom, alkyl, substituted alkyl, alkoxy, aryloxy, alkyl sulphanyl, aryl sulphanyl, aromatic amino, fatty amino and heterocyclic substituent; L^Y can be one of N^COOH, N^OH, beta-diketone, N^NH and the like; N^N can be bipyridyl, biquinolyl, phenanthroline and derivatives thereof and the like; and Z can be a hexafluorophosphoric acid radical, a perchloric acid radical and the like. A light-emitting layer of the electroluminescent device disclosed by the invention is prepared by adopting a spin coating and film-preparing method under a specified condition, has the advantages of being low in cost, simple for operation and steady in chemical property, and is beneficial to preparing large-screen electroluminescent devices.

Description

technical field [0001] The invention relates to the technical field of electroluminescence, in particular to a class of phosphorescent iridium complexes with quinazoline derivatives as ligands and an organic electroluminescence device thereof. Background technique [0002] Organic electroluminescence (Electroluminescence, hereinafter referred to as EL) has the advantages of low driving voltage, fast response speed, wide viewing angle range, and the ability to fine-tune the chemical structure to change the luminescence performance and enrich the colors, making it the most competitive in the third-generation flat panel display. force. In 1987, Kodak's Tang et al. adopted ultra-thin film technology, used 8-hydroxyquinoline aluminum (Alq3) as the light-emitting layer, and introduced the hole transport layer for the first time, and obtained a low-voltage DC-driven high-brightness organic electroluminescent device. In 1998, Junji Kido et al. used 8-hydroxyquinaldine aluminum (Alm...

Claims

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Application Information

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IPC IPC(8): C07F15/00H01L51/54
Inventor 梅群波王玲霞黄维郭远辉颜芳翁洁娜
Owner NANJING UNIV OF POSTS & TELECOMM
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