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Organic metal iridium compound and organic light-emitting device (OLED)

An organic light-emitting device and organometallic technology, applied in indium organic compounds, platinum group organic compounds, organic chemistry, etc., can solve the problems of material melting point and heat resistance decline, unfavorable display materials, etc., to improve photoelectric performance and reduce stacking Function, the effect of lowering the sublimation temperature

Inactive Publication Date: 2018-12-21
ZHEJIANG FORST NEW MATERIAL RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, too much introduction of alkyl chains will often lead to a decrease in the melting point and heat resistance of the material, which is unfavorable for display materials; moreover, as far as the current OLED display lighting industry needs are concerned, the performance of current OLED materials It cannot meet the needs of the industry, so it is particularly important to develop high-performance and high-efficiency OLED materials

Method used

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  • Organic metal iridium compound and organic light-emitting device (OLED)
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  • Organic metal iridium compound and organic light-emitting device (OLED)

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of organometallic iridium compound R-2:

[0023]

[0024] 1.1 Synthesis of TM-1:

[0025] Under nitrogen protection conditions, quinoline-4-carboxylic acid 17.3g (100mmol) was dissolved in 100mL tetrahydrofuran, mixed with 157mL (220mmoL) sec-butyllithium (1.4M) at -40°C, removed from the freezer, and the reaction solution Place in the water tank at room temperature for 60 minutes, stir for 2 hours, cool at -78°C, add dropwise 100mL of tetrahydrofuran mixed with 14.4g (150mmol) methanesulfonic acid, remove the cold water tank, and place the mixture in the water tank at room temperature for 30 minutes, then cool at 60°C Reflux for 5 hours.

[0026] After the reaction stopped, it was washed with saturated sodium chloride, and then 2N aqueous HCl was added, stirred for 30 minutes, and then extracted with ether. Use anhydrous magnesium sulfate to remove the moisture in the organic layer, filter with suction, and concentrate the obtained comp...

Embodiment 2

[0045] Embodiment 2: the synthesis of organometallic iridium compound R-31:

[0046]

[0047] 1.1 Synthesis of TM-1:

[0048] 1-Bromo-2-(2-phenylpropane)benzene (21.5 g, 78.5 mmol) in THF (500 ml) was treated with 31.8 mL of n-BuLi (2.5 M in hexane, 78.5 mmol) at -78 °C under nitrogen. solution in. The mixture was stirred for 30 minutes. A solution of quinolin-4-one (12.16 g, 78.5 mmol) in 300 mL THF was added dropwise. The reaction was allowed to proceed at -78°C for 30 minutes, then stirred at room temperature overnight. The reaction was quenched with water, and the solid was filtered. A mixture of the alcohol, acetic acid (220 mL) and concentrated HCl (10 mL) was refluxed for 2 hours without further purification.

[0049] After cooling, the mixture was filtered and washed with water, and dried under vacuum. The product was isolated in the form of a white solid (24 g, 92% of theory).

[0050] 1.2 Synthesis of TM-2:

[0051] Under the condition of nitrogen protecti...

Embodiment 3

[0062] Embodiment 3: the synthesis of organometallic iridium compound R-84:

[0063]

[0064] 1.1 Synthesis of TM-2:

[0065] Under the condition of nitrogen protection, TM-1 15.5g (100mmol) was dissolved in 500mL dry dichloromethane, 52g m-CPBA (300mmoL) was added at room temperature, and the reaction was carried out at room temperature for 16h.

[0066] After the reaction stopped, 500 mL of ice water was added to the reaction system, and after stirring for 30 minutes, precipitation occurred. Suction filtration under reduced pressure, washing with water for several times, recrystallization from ethanol to obtain 17.1 g (90%) of intermediate TM-2, HPLC: 99.0%.

[0067] 1.2 Synthesis of TM-3:

[0068] Under the condition of nitrogen protection, TM-2 15.2g (80mmol) was dissolved in 500mL dry THF, 45g 2-tributylstannylthiophene (120mmoL) was added at room temperature, nitrogen was replaced three times, and the temperature was raised to 70°C for 16h .

[0069] After the rea...

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Abstract

The invention discloses an organic metal iridium compound and an organic light-emitting device (OLED). A complex is fused into a ring by using a 4-sit substituent and a 5-sit substituent of a quinoline position so as be used as a structural unit part of the organic metal iridium compound, so that not only is the inter-molecular stacking effect reduced, but the improvement of the photoelectric performance of the OLED device is also facilitated, the sublimation temperature is lowered, and the original organic metal iridium compounds which are difficult to sublimate and purify are enabled to become materials which are easy to sublimate and easy in large-scale evaporation preparation of OLED devices. The organic metal iridium compound provided by the invention has good photoelectric propertiesand can be applied to the field of OLED illumination or OLED display.

Description

technical field [0001] The invention relates to a light-emitting device, in particular to an organic metal iridium compound and an organic electroluminescence device prepared therefrom. Background technique [0002] Compared with liquid crystal display (LCD), organic electroluminescent device (OLED) has low driving voltage; high luminous brightness and luminous efficiency; wide luminous viewing angle and fast response speed; in addition, it is ultra-thin and can be fabricated on flexible panels, etc. advantage. Known as the third generation of flat panel display technology. As an organic electroluminescent diode for next-generation flat panel display applications, organic photoelectric semiconductor materials require: 1. High luminous efficiency; 2. Excellent stability of electrons and holes; 3. Appropriate luminous color; 4. Excellent processability . Various types of light-emitting diodes currently used mainly include organic small molecule light-emitting diodes (OLEDs)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033H10K85/40H10K85/342
Inventor 洪海兵周光大林建华
Owner ZHEJIANG FORST NEW MATERIAL RES INST CO LTD
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