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Novel iridium complex and preparation method thereof as well as application thereof in organic electroluminescence device

An iridium complex and reaction technology, applied in the field of preparation of organic electroluminescent devices, can solve the problems of high energy consumption of devices, unfavorable device stability and lifespan, increase of device temperature, etc., and achieve the effect of good luminescence performance

Inactive Publication Date: 2013-12-18
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The lower luminous efficiency not only makes OLEDs devices consume more energy, but also the energy of triplet excitons without radiation attenuation will be released in the form of heat, which will increase the temperature of the device, which is also unfavorable to the stability and life of the device.

Method used

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  • Novel iridium complex and preparation method thereof as well as application thereof in organic electroluminescence device
  • Novel iridium complex and preparation method thereof as well as application thereof in organic electroluminescence device
  • Novel iridium complex and preparation method thereof as well as application thereof in organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Synthesis of the main ligand L1-L4

[0038] Under oxygen-free nitrogen protection conditions, 25mmol2-bromopyridine, 30mmol2-(trifluorophenyl)boronic acid or 2-(tetrafluorophenyl)boronic acid, 0.35g (0.30mmol) tetrakis(triphenylphosphine) palladium catalyst And 16.56g (120mmol) of potassium carbonate, dissolved in 120mL tetrahydrofuran: water = 2:1 mixed solvent, heated to reflux at 80°C, and followed the reaction by thin layer chromatography. After the reaction was completed, it was cooled and extracted three times with 30 mL of dichloromethane (30 mL). Collect the organic phase, dry with anhydrous magnesium sulfate, and then use 300 mesh silica gel column chromatography, the eluent used is sherwood oil: ethyl acetate=10:1 mixed solvent, obtain white solid L1-L4, yield 82- 90%. The characterization data of the obtained compound are as follows:

[0039] main ligand L1

[0040] Yield: 82%

[0041] 1 HNMR (500MHz, acetone-d 6 ,ppm)δ8.69(d,J=4.7Hz,1H),8.02...

Embodiment 2

[0059] Synthesis of Example Two Auxiliary Ligand AL and Its Potassium Salt KAL

[0060] Under anhydrous and oxygen-free conditions, 20mmol of phosphorus chloride with different substituents was dissolved in 30mL of anhydrous toluene, heated to reflux, and 1.77g (11mmol) of hexamethyldisilamine (HMDS) was slowly added dropwise. Continue to react under reflux for 6h. After the reaction is over, cool down and remove the reaction by-product trimethylchlorosilane and solvent by rotary evaporation. Then it was dissolved in 4mL THF, and the mixed solution of 2mL 30% hydrogen peroxide and 5mL THF was slowly added dropwise to the reaction liquid, and reacted for 2h after the dropwise completion. After the end, the liquid was poured into 50 mL of ether solution, and a large amount of white precipitates were formed. The precipitates were washed with water and dried in vacuum to obtain the product AL.

[0061] At room temperature, slowly drop 10mL of 2% methanolic potassium hydroxide sol...

Embodiment 3

[0092] The synthesis of embodiment three iridium complexes

[0093] The reaction is carried out under anhydrous and anaerobic operation, 0.20mmol of [(F-ppy) 2 Ir(μ-Cl)] 2 and 2.5 times the equivalent of KAL (0.5mmol) were dissolved in 10mL of ethylene glycol monoethyl ether solution, and reacted at 120°C for 24h. After the reaction, a small amount of yellow precipitate was formed, and the solvent was distilled off under reduced pressure. Silica gel column chromatography, the eluent used is a mixed solvent of petroleum ether: ethyl acetate with a volume ratio of 10:1-7:1. The product was precipitated by adding petroleum ether to obtain a yellow solid, which was dried in vacuum and purified by sublimation to obtain an iridium complex, melting point: >310°C.

[0094] The characterization data of the obtained compound are as follows:

[0095] Complex Ir-a

[0096] Yield: 28%

[0097] 1 HNMR (500MHz, CDCl 3 ,ppm)δ9.03(d,J=5.6Hz,2H),7.77(dd,J=12.3,7.0Hz,4H),7.50(d,J=8.1Hz,14...

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Abstract

The invention discloses an iridium complex with four types of different-site and different-quantity fluoro-substituted 2-phenylpyridine serving as main ligands, and bi(bisubstituent phenyl phosphoro)amine serving as an auxiliary ligand. The formula of the iridium complex is shown in the specification. Emission peaks of an EL (electroluminescence) spectrum of an electroluminescence device prepared from the iridium complex are respectively 497nm, 497nm and 495nm; maximum current efficiencies are respectively 43.95cd / A, 66.36cd / A and 37.36cd / A; maximum power efficiencies are respectively 28.51 lm / W, 48.20 lm / W and 19.11 lm / W; maximum power efficiencies are respectively 38827cd / m<2>, 47627cd / m<2> and 40319cd / m<2>. The invention discloses a preparation method of the iridium complex.

Description

technical field [0001] The invention relates to the synthesis of metal organic iridium complexes, and also to the preparation of organic electroluminescent devices based on the complexes. Background technique [0002] Since entering the 21st century, driven by the third industrial revolution, the information age has come among us and facilitated our lives. As the information display technology of human-machine interface, it is constantly updated following the development of science and technology. From the original cathode ray tube (CRT) to the advanced liquid crystal display (LCD), from the emerging plasma display device (PDP) to the field emission array flat panel display (FED), they are constantly improving and perfecting to adapt to society and society. market demand. Since these existing display technologies cannot meet people's increasingly higher requirements for information display devices, it has become the research focus of researchers all over the world to conti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 王铖铖徐秋蕾张松荆一铭李天一刘旋郑佑轩左景林游效曾
Owner NANJING UNIV
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