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Metal-containing organic complex and OLED (organic light-emitting diode) device comprising same

An organic complex and metal technology, applied in the field of metal-containing organic complexes and their organic light-emitting devices, can solve the problem that high-performance red phosphorescent materials need to be further developed.

Inactive Publication Date: 2018-10-02
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The efficiency and lifespan of green and yellow organic phosphorescent materials can basically meet the requirements of industrialization, but high-performance red phosphorescent materials still need to be further developed

Method used

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  • Metal-containing organic complex and OLED (organic light-emitting diode) device comprising same
  • Metal-containing organic complex and OLED (organic light-emitting diode) device comprising same
  • Metal-containing organic complex and OLED (organic light-emitting diode) device comprising same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Embodiment 1: the preparation of compound 1

[0080]

[0081] Preparation of intermediate A1

[0082] Under nitrogen protection, compound 2-biphenylboronic acid-a1 and compound 2,5-dibromopyridine-b1 were added to a 100mL four-necked flask, and tetrakistriphenylphosphopalladium Pd (PPh 3 ) 4 (1.8g, 1.53mmol), a carbon-carbon coupling reaction occurred to obtain compound c1. Compound c1 (2.9 g, 10.9 mmol), iodine (281 mg, 1.1 mmol), and toluene were charged into a double-walled quartz photochemical reactor equipped with magnetic stirring, air bubbler and UV lamp. Gentle air was bubbled through the solvent while irradiating it for 15 hours in the reaction to compound d1. Compound d1 and compound phenylboronic acid-e1 undergo a carbon-carbon coupling reaction with tetrakistriphenylphosphine palladium as a catalyst and potassium carbonate as a base to generate intermediate A1.

[0083] Preparation of Intermediate B1

[0084] In a 1L three-necked flask, iridium trich...

Embodiment 2

[0089] Embodiment 2: the preparation of compound 2

[0090]

[0091] Preparation of Intermediate A2

[0092] Under nitrogen protection, compound g2 and compound h2 were added to a 100mL four-necked flask, and tetrakistriphenylphosphopalladium Pd (PPh 3 ) 4 (1.8g, 1.53mmol), a carbon-carbon coupling reaction occurred to obtain compound i2.

[0093] Compound i2 and compound m2 were added in a 100mL four-necked flask, and tetrakistriphenylphosphopalladium Pd (PPh 3 ) 4 (1.8g, 1.53mmol), a carbon-carbon coupling reaction occurred to obtain compound n2. Compound n2 was dissolved in tetrahydrofuran (140 mL), and a hexane solvent and 2.5M n-butyllithium (18 mL, 45.1 mmol) were added dropwise at -78°C, followed by stirring for 1 hour. After slowly adding trimethyl borate (13 mL, 56.4 mmol) dropwise, stirred for 2 h. Then 2M hydrochloric acid was added dropwise to neutralize, and the product was extracted with ethyl acetate and water. Compound a2 was obtained by recrystalliza...

Embodiment 3

[0101] Embodiment 3: the preparation of compound 9

[0102] The m2 in Example 2 was replaced by equimolar m9, and the other steps were the same as in Example 2 to obtain the target compound 9 (6.71 g, 29%).

[0103]

[0104] Mass Spectrum m / z: 1157.42 (calculated: 1157.41). Theoretical element content (%)C 71 h 56 IrN 4 : C, 73.68; H, 4.88; Ir, 16.61; N, 4.84 Measured element content (%): C, 73.68; H, 4.87; Ir, 16.62; N, 4.84. The above results confirmed that the obtained product was the target product.

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Abstract

The invention discloses a metal-containing organic complex and an OLED (organic light-emitting diode) device comprising the same and relates to the technical field of organic optoelectronic materials.The structure comprises a first ligand and an auxiliary ligand, wherein the first ligand solves the problem of roll-off of the efficiency of the device at high-current density by introducing large pai conjugated structures and steric hindrance groups; an electron-rich double-nitrogen coordination structure in the auxiliary ligand is favorable for stabilizing central trivalent metal ions, meanwhile, distribution of electron clouds on iridium can also be affected, and further, a great influence is produced on the photoelectric property of the whole complex molecule; a four-membered ring formedby the ligand adopting the double-nitrogen coordination structure and metal has higher rigidity, accordingly, unnecessary vibration energy loss is favorably reduced, and the efficient light emitting performance is realized. The complex has better heat stability and chemical properties by adjusting substituent groups. The metal-containing organic complex particularly as a doping material is prepared into the device, and the device has the advantages of low driving voltage and high light emitting efficiency and is superior to existing common OLED devices.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a metal-containing organic complex and an organic light-emitting device thereof. Background technique [0002] In 1987, Deng Qingyun and others from Kodak Corporation of the United States first evaporated organic compounds into amorphous organic thin films by vacuum evaporation, and selected different organic materials as hole and electron transport layers to prepare double-layer OLED devices. When the voltage of the device is about 10V, the brightness of the device reaches 1000cd m -2 , the maximum external quantum efficiency EQE (External Quantum Efficiency) is about 1%, showing a very good electroluminescent performance, which indicates that the organic electroluminescent device (OLED) has the possibility of practical application. Since then, Major companies and scientific research institutions have invested a lot of manpower and resources in the resea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/11
Inventor 韩春雪蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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