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Phenanthroline-containing organic complex and organic light emitting device (OLED) thereof

An organic light-emitting device and organic complex technology, which are applied in the field of phenanthroline-containing organic complexes and organic light-emitting devices, can solve the problem that high-performance red phosphorescent materials need to be further developed, and meet the requirements of industrialization. The effect of demand, easy availability of raw materials, and simple preparation method

Inactive Publication Date: 2018-09-14
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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  • Phenanthroline-containing organic complex and organic light emitting device (OLED) thereof
  • Phenanthroline-containing organic complex and organic light emitting device (OLED) thereof
  • Phenanthroline-containing organic complex and organic light emitting device (OLED) thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1: the preparation of compound 1

[0073] Preparation of Intermediate A1

[0074]

[0075] In a 1L three-necked flask, add iridium trichloride hydrate (14.1g, 40mmol) and compound 1,10 phenanthroline-e1 (35.1g, 170mmol), then add 300mL2-ethoxyethanol and 100mL water, and the mixture is Reflux overnight under nitrogen atmosphere. After the reaction, the temperature was lowered to room temperature, the precipitate was filtered, washed with methanol, and dried to obtain intermediate A1 (23.89 g, yield 90%).

[0076] Mass Spectrum m / z: 1327.29 (calculated: 1327.28). Theoretical element content (%)C 59 h 51 Cl 2 Ir 2 N 8 H, 3.87; Cl, ​​5.34; Ir, 28.96; N, 8.44 Measured element content (%): C, 53.39; H, 3.86; Cl, ​​5.34; The above results confirmed that the obtained product was the target product.

[0077] Preparation of Compound 1

[0078] Bromobenzene (3.1g, 20mmol) in n-hexane (100mL) was added to a 100mL four-neck flask, cooled to -80°C, and n-buty...

Embodiment 2

[0080] Embodiment 2: the preparation of compound 2

[0081]

[0082] Methylboronic acid (2.30g, 38.4mmol), c2 (7.95g, 30.7mmol) and K 2 CO 3 (8.48g, 61.4mmol) was dissolved in toluene (150ml) and water (30ml). The mixture was degassed by bubbling it with nitrogen for 30 minutes, and tetrakistriphenylphosphopalladium Pd (PPh 3 ) 4(1.78 g, 1.53 mmol). The mixture was then kept at 100°C overnight. After completing the reaction, the mixture was cooled to room temperature, extracted with toluene, and washed with brine and water. The organic solution was filtered and evaporated. The crude product was purified by column chromatography using a gradient mixture of ethyl acetate in heptane (20% to 65%). The white powder product was recrystallized three times from heptane to give e2 as colorless crystals. In a 1L three-necked flask, iridium trichloride hydrate (14.1g, 40mmol) and compound e2 (33.02g, 170mmol) were added, then 300mL of 2-ethoxyethanol and 100mL of water were ad...

Embodiment 3

[0087] Embodiment 3: the preparation of compound 8

[0088] The methyl bromide in Example 2 was replaced by equimolar bromobenzene, and the other steps were the same as in Example 2 to obtain the target compound 8 (5.27 g, 29%).

[0089]

[0090] Mass Spectrum m / z: 909.34 (calculated: 909.33). Theoretical element content (%)C 49 h 44 IrN 6 : C, 64.74; H, 4.88; Ir, 21.14; N, 9.24 Measured element content (%): C, 64.75; H, 4.88; Ir, 21.13; N, 9.24. The above results confirmed that the obtained product was the target product.

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Abstract

The invention discloses a phenanthroline-containing organic complex and an organic light emitting device (OLED) thereof and relates to the technical field of organic photoelectric materials. An electron-rich diazo coordination structure in the complex structure is favorable for stabilizing the central trivalent metal cation and also influences the distribution of electron cloud on metal iridium, thereby generating great influence on photoelectric properties of whole complex molecules; and a four-membered ring composed of the ligand of the diazo coordination structure and metal has stronger rigidity, thereby being favorable for reducing unnecessary vibration energy loss and realizing efficient light emitting performance. By adjusting substituent groups, the complex has better thermal stability and chemical properties. The complex can be prepared into a device and especially can serve as a doping material, and the device shows the advantages of low driving voltage and high light emittingefficiency and is superior to an existing common OLED.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an organic complex containing phenanthroline 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/004C09K2211/185H10K85/342H10K50/11
Inventor 韩春雪蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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