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Near-infrared luminous material and OLEDs (organic light-emitting diodes)

A luminescent material and near-infrared technology, applied in luminescent materials, electric solid devices, electrical components, etc., can solve problems such as enlargement and decrease in luminous efficiency

Active Publication Date: 2015-07-29
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the research on cyclometalated iridium complexes in the near-infrared region has not yet made a breakthrough. The two difficulties in the current research are: further red-shifting the luminous wavelength and improving the near-infrared luminous efficiency. Adjust the molecular structure to reduce the energy gap between HOMO-LUMO. However, according to the energy gap rule, as the energy gap narrows, the rate of non-radiative relaxation of the excited state will increase, resulting in a decrease in luminous efficiency.

Method used

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  • Near-infrared luminous material and OLEDs (organic light-emitting diodes)
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  • Near-infrared luminous material and OLEDs (organic light-emitting diodes)

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preparation example Construction

[0040] The preparation of the L2 ligand can refer to the following routes and methods:

[0041]

[0042] Dissolve 2.1 g (6.35 mmol) of the ligand raw material in 40 mL of methanol, add excess hydrazine hydrate, stir at room temperature for 1 hour until yellow precipitates, and then recrystallize with methanol, yield 90%.

[0043] Different said L2 ligands can be obtained with substituted formyl ethane and hydrazine hydrate.

[0044] The preparation of the L3 ligand can refer to the following routes and methods:

[0045]

[0046] Dissolve 2mmol of 3-aminonaphthalene-2-benzophenone, 3mmol of glycine, 1mmol of iodine and 0.55mL of tert-butyl hydroperoxide (70% aqueous solution) in 5mL of dimethylformamide, and place in a sealed tube at 80°C React for 18 hours. Separated by column chromatography, a yellow solid was obtained with a yield of 70%.

[0047] Different L3 ligands can be obtained with substituted 3-aminonaphthalen-2-benzophenones and substituted glycine.

[004...

Embodiment 1

[0059] Embodiment 1: Preparation of iridium complex C1-1

[0060]

[0061] IrCl 3 ·xH 2 O (58% Ir) and 2.2 times the chemical equivalent of L1 ligand were dissolved in a mixed solvent of ethylene glycol methyl ether and deionized water (v / v=3 / 1). The mixture was stirred under reflux at 110° C. for 24 hours under an Ar atmosphere. After cooling to room temperature, filter, wash the filter cake with deionized water until neutral, then rinse the filter cake with 10mL ethanol and 200mL diethyl ether in sequence. Finally, the filter cake was dissolved with dichloromethane, the filtrate was collected, the solvent was evaporated, and vacuum-dried at 70° C. for 5 hours to obtain the dichloro-bridged intermediate as a dark brown solid with a yield of 85%, which was directly put into the next reaction without further purification.

[0062] Dissolve 0.34mmol of the dichloro-bridged intermediate and 1.0g of 4,7-diphenyl-1,10-phenanthroline in 40mL of ethylene glycol, protect the rea...

Embodiment 2

[0065] Embodiment 2: the preparation of iridium complex C1-2

[0066]

[0067] Please refer to Example 1 for the preparation method of the dichloro-bridged intermediate.

[0068] 0.17mmol of dichloro-bridged intermediate, 0.05g (0.5mmol) of acetylacetone and 0.056g (0.5mmol) of potassium tert-butoxide were dissolved in 12mL of dichloromethane / ethanol (volume ratio=3 / 1) mixed solvent. The reaction system was protected by argon, and stirred under reflux at 30°C for 24 hours. After cooling to room temperature, the solvent was evaporated to dryness, then dissolved in dichloromethane, extracted three times with deionized water, and washed with anhydrous MgSO 4 The organic phase is dried. Filter, distill off the solvent, separate by column chromatography, and collect the black product band. After concentration, it was recrystallized with dichloromethane / ether to obtain a black solid with a yield of 45%.

[0069] 1 H-NMR (nuclear magnetic resonance, CDCl 3 ,300MHz,δ[ppm]): 1...

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Abstract

The invention provides an iridium complex used as a near-infrared luminous material and OLEDs (organic light-emitting diodes) comprising the iridium complex. The general structural formula of the iridium complex is LnIrX(3-n) or [LnIrX(3-n)]<+>Z<->, wherein Ir represents a central atom of the iridium complex, both L and X are ligands of the iridium complex, Z<-> represents an anion, n is equal to 1, 2 or 3, and L is selected from an L1 ligand, an L2 ligand or an L3 ligand with the general formula represented in the specification.

Description

technical field [0001] The invention relates to a near-infrared luminescent material, in particular to a metal iridium complex and an organic electroluminescent device using the metal iridium complex, belonging to the technical field of organic light emitting displays. Background technique [0002] The near-infrared region refers to a section of the spectrum with a wavelength from 700 nanometers to 1500 nanometers. In recent years, near-infrared materials and technologies have attracted more and more attention and investment from the scientific community. In terms of military supplies, near-infrared technology is used for heat source target locking, regional defense, night vision equipment, missile positioning and target tracking, etc.; in civilian use, near-infrared technology can be used for thermal efficiency analysis, temperature remote sensing transmission, short-range wireless communication and weather forecasting etc.; in biological tissues and cells, near-infrared l...

Claims

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Application Information

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IPC IPC(8): C07F15/00C07D221/08C07D409/04C07F5/02C07D237/26C07D239/70C09K11/06H01L51/54
CPCC09K11/06C07D221/08C07D221/18C07D237/26C07D239/70C07D401/04C07D409/04C07D409/14C07D471/04C07F5/02C07F15/0033C09K2211/1011C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1092H10K85/6572H10K50/11C09B57/00C09B57/10C07D213/22C07D213/79H10K85/1135H10K85/146H10K85/326H10K85/342H10K2101/10
Inventor 乔娟辛利君
Owner TSINGHUA UNIV
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