Isoquinoline triarylamine cyclic metal complex and its uses

A technology of isoquinolinyl triarylamine and ring metal, which is applied in the application field of polymer electroluminescent devices, can solve the problems of reduced luminous efficiency of electrophosphorescent devices, reduction of luminous efficiency and life of devices, aggregation of electrophosphorescent molecules, etc.

Inactive Publication Date: 2009-07-22
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problems of electrophosphorescence are: (1) organic small molecule electrophosphorescent materials (guests) are doped in the host material, and under the action of electricity and heat, the aggregation of electrophosphorescent molecules is easy to occur, resulting in phase separation, resulting in phosphorescence Quenching, reducing the luminous efficiency and lifetime of the device; (2) The maximum luminous efficiency of organic small molecule / polymer electrophosphorescent devices is mostly obtained at lower current densities
When the current density increases, the luminous efficiency of electrophosphorescent devices decreases rapidly; (3) the luminous efficiency of polymer electrophosphorescent devices is generally lower than that of organic small molecule electrophosphorescent devices, which restricts the efficiency of polymer electrophosphorescent devices. Development of Phosphorescent Displays

Method used

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  • Isoquinoline triarylamine cyclic metal complex and its uses
  • Isoquinoline triarylamine cyclic metal complex and its uses
  • Isoquinoline triarylamine cyclic metal complex and its uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Synthesis of 4-(1-isoquinolinyl)aniline

[0085]

[0086] 1. Synthesis of p-nitrobenzoyl chloride:

[0087] Add 30g (179mmol) p-nitrobenzoic acid to a 250mL single-neck bottle, install a condenser tube, quickly pour 76mL of thionyl chloride from the upper end of the condenser tube, install a drying tube, and reflux for 5 hours to obtain a pale yellow liquid, normal pressure The excess thionyl chloride was recovered by distillation and cooled to obtain 31.5 g of a pale yellow solid with a yield of 94.0%.

[0088] 2. Synthesis of N-(2-phenylethyl) p-nitrobenzamide:

[0089] In a 500mL three-necked flask, add 31.5g (169mmol) of p-nitrobenzoyl chloride, dissolve in 350mL of dichloromethane, add 22.2mL of β-phenethylamine dropwise under an ice-water bath, then add 26mL of triethylamine, the solution The turbidity became orange-red and transparent, and stirring was continued at room temperature for 26 hours. Pour the solution into a 1000mL beaker, add about 150mL of dic...

Embodiment 2

[0097] Synthesis of isoquinolinyl triarylamine

[0098]

[0099] R=hydrogen atom, tert-butyl, methyl, methoxy.

[0100] In a 50mL three-necked flask, 1.3g (5.9mmol) of 1-(4-aminophenyl)isoquinoline, 14.5mmol of substituted iodobenzene, 6.6g (47.8mmol) of anhydrous potassium carbonate, 1.5g of copper powder, 0.4 g dibenzo-18-crown-6-ether and 25 mL of o-dichlorobenzene were heated and refluxed for 24 hours under nitrogen protection, cooled, the reaction mixture was suction filtered, and o-dichlorobenzene was recovered by distillation under reduced pressure. Using ~300 mesh silica gel as the stationary phase and dichloromethane as the eluent, the product was separated by column chromatography to obtain a yellow solid product.

[0101] N,N-Diphenyl-4-(1'-isoquinolinyl)aniline (DPAPiq), yield 77.6%, m.p.142-144°C. 1 H NMR (400MHz, CDCl 3 )δppm: 8.60~8.59(d, 1H), 8.26~8.24(d, 1H), 7.90~7.88(d, 1H), 7.73~7.69(t, 1H), 7.64~7.56(m, 4H), 7.32~ 7.19 (m, 10H), 7.09-7.05 (t, 2H). ...

Embodiment 3

[0106] Synthesis of Isoquinolinyl Triarylamine Ring Metal Iridium Complex Electrophosphorescent Materials

[0107]

[0108] R=hydrogen atom, tert-butyl, methyl, methoxy.

[0109] In a 50mL three-necked flask, add 1.62mmol of the compound of Example 2, 15mL of ethylene glycol monoethyl ether and 5mL of water, stir magnetically, heat through nitrogen for deoxygenation for 30 minutes, and after cooling, quickly add 142mg (0.40mmol) of IrCl 3 ·3H 2 O, under the protection of nitrogen, the reaction was heated to reflux for 25 hours, cooled, and a red precipitate was precipitated. Suction filtration, the precipitate was washed with 95% ethanol (5mL×2), acetone (5mL×2) and n-hexane (5mL×2) successively, and dried in vacuum to obtain a red dimer solid of chloride-bridged metal iridium .

[0110] 0.15 mmol dimer solid, 40.2 mg (0.40 mmol) acetylacetone, 20.3 mg Na 2 CO 3 and 15mL of ethylene glycol monoethyl ether, added to a 50mL three-necked flask, under nitrogen protection, ...

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Abstract

The invention discloses a kind of isoquinolyl triarylated amine cyclic metal complexes and their applications in electroluminescent devices. The isoquinolyl triarylated amine cyclic metal ligand can not only adjust hole injection and transmission performance of metal complexes, but inhibit molecular aggregation and concentration quenching of cyclic metal complexes due to the non-planar structure of triarylated amine. Therefore, metal iridium complexes and platinum ring metal complexes with isoquinolyl triarylated amine as the cyclic metal ligands can improve photoelectric performance, and can be used as red luminescent materials in polymer electroluminescent devices, achieving efficient luminescence.

Description

technical field [0001] The invention relates to the field of organic electroluminescence, in particular to the preparation of a class of isoquinolinyl triarylamine ring metal ligands and their ring metal iridium complexes and ring metal platinum complexes electrophosphorescent materials and their application in the field of electroluminescence , especially in the application of polymer electroluminescent devices. Background technique [0002] Since the platinum-porphyrin complex (PtOEt) high-efficiency organic electrophosphorescence device was first reported by the Forrest research group of Princeton University in 1998 (Nature, 1998, 395, 151.), organic / polymer electrophosphorescence has been widely used in countries all over the world. Researchers have paid close attention to it and gained rapid development. Different from electrofluorescence, electrophosphorescence is considered to be the most effective way to realize high luminous efficiency and long lifetime display dev...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 朱卫国胡峥勇罗翠萍朱美香
Owner XIANGTAN UNIV
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