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Deep red phosphorescent iridium complex, preparation method thereof, and organic electroluminescent device using the complex

A phosphorescent iridium complex, red light technology, applied in electric solid devices, electrical components, luminescent materials, etc., can solve the problems of scarcity of deep red dyes, limit the development of red OLEDs and high CRI white OLEDs, etc. force, reducing self-quenching phenomenon, improving the effect of electroluminescence performance

Active Publication Date: 2017-09-22
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, highly efficient solution-processed deep-red dyes are very scarce, which limits the development of red-emitting OLEDs and high-CRI white-emitting OLEDs.

Method used

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  • Deep red phosphorescent iridium complex, preparation method thereof, and organic electroluminescent device using the complex
  • Deep red phosphorescent iridium complex, preparation method thereof, and organic electroluminescent device using the complex
  • Deep red phosphorescent iridium complex, preparation method thereof, and organic electroluminescent device using the complex

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preparation example Construction

[0032] A preparation method for a deep red phosphorescent iridium complex, comprising the steps of:

[0033] In a protective gas atmosphere, 2,5-dibromopyridine and compound A with a molar ratio of 1:2.1-2.5 were dissolved in the first solvent, and an organopalladium catalyst and an aqueous solution of carbonate were added to carry out the Suzuki coupling reaction 8-24h, compound B is obtained after separation and purification, and the structural formula of compound A is The structural formula of compound B is Wherein R is a hydrogen atom or an alkyl group with 1-20 carbon atoms.

[0034] The protective gas is argon, nitrogen or neon.

[0035] The first solvent is toluene or tetrahydrofuran (THF). The amount of the first solvent is suitable to fully dissolve compound A and 2,5-dibromopyridine.

[0036] The organic palladium catalyst is tetrakistriphenylphosphine palladium (Pd(PPh 3 ) 4 ), preferably, the molar ratio of the organopalladium catalyst to 2,5-dibromopyridin...

Embodiment 1

[0077] Synthesis of Deep Red Phosphorescent Iridium Complex Bis(2,5-(3-Hexylthiophene)pyridine-N,C)(Acetylacetonate)Iridium Complex

[0078] The structural formula of deep red phosphorescent iridium complex bis(2,5-(3-hexylthiophene) pyridine-N, C) (acetylacetonate) iridium complex is as follows:

[0079]

[0080] (1) Synthesis of 2,5-(3-hexylthiophene)pyridine

[0081]

[0082] Under argon protection, 2.2g 3-hexylthiophene boronic acid, 1.0g 2,5-dibromopyridine, 0.24g tetrakis(triphenyl)phosphine palladium catalyst and 8ml 2mol / L potassium carbonate solution were added to 100ml of tetrahydrofuran (THF), the reaction was stirred at 90°C for 24 hours. After the reaction, it was extracted with ethyl acetate, separated, washed with water until neutral, and dried over anhydrous magnesium sulfate. After filtration and spin-drying, silica gel column chromatography was performed using petroleum ether / dichloromethane as eluent, and after drying, 1.7 g of light yellow solid was...

Embodiment 2

[0090] First clean the indium tin oxide conductive glass (ITO glass) with indium tin oxide (ITO) cleaning agent, then clean it with distilled water, and finally treat it with ultraviolet ozone (UVO) for 25 minutes; spin it on the indium tin oxide conductive glass at a speed of 3000 rpm Coating polyethylenedioxythiophene-poly(styrene sulfonate) (PEDOT) for one minute and baking at 120° C. for one hour to obtain the anode of the organic electroluminescence device. The anode is disposed on the substrate.

[0091] 10mgTCTA and the iridium complex prepared in Example 1 and 1mL chlorobenzene were mixed to configure a 10mg / mL chlorobenzene solution, and then spin-coated on the anode at a speed of 1500 rpm for one minute, and 100 under an inert atmosphere ℃ heat treatment for 30min to obtain an organic electroluminescent layer;

[0092] The organic electroluminescent layer was placed at 4×10 -4 Under the vacuum degree of Pa, a 50nm thick electron injection / transport layer of 2,7-bis...

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Abstract

The invention relates to a deep red phosphorescence material iridium complex, its preparation method and an organic electroluminescent device. The deep red phosphorescence material iridium complex has the following structural formula, wherein, R is a hydrogen atom or an alkyl group with 1-20 carbon atoms. The deep red phosphorescent iridium complex of the present invention uses 2,5-(3-alkylthiophene)pyridine as the main structure of the ring metal ligand, acetylacetone as the auxiliary ligand, and linear or branched alkanes of different lengths. The introduction of the group into the thiophene ring can not only increase the solubility of the material in common solvents, but also reduce the interaction force between the material molecules and reduce the self-separation of the triplet excitons in the solid film. quenching phenomenon. The deep red phosphorescence material iridium complex of the invention can improve the electroluminescent performance of organic electroluminescent devices.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a deep red phosphorescent iridium complex, a preparation method thereof and an organic electroluminescent device using the complex. Background technique [0002] Organic Light-Emitting Diodes (OLEDs) have attracted extensive attention from academia and industry due to their advantages such as high brightness, low driving voltage, light weight, and low processing cost for large-area flexible displays. Become the first choice for future display technology. [0003] According to the different luminescent principles, organic electroluminescent materials can be divided into two categories: fluorescence and phosphorescence. Since phosphorescent materials can simultaneously utilize singlet and triplet excitons, the internal quantum efficiency of the device can theoretically reach 100%. Therefore, transition metal complexes are widely used in th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342
Inventor 谢志元刘雪景张保华吴江
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI