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Blue light-emitting organic electroluminescent material, its preparation method and organic electroluminescent device

A luminescent and electromechanical technology, applied in luminescent materials, electrical solid devices, organic chemistry, etc., can solve problems such as poor blue light color purity, luminous color purity of blue light luminescent materials, luminous efficiency device efficiency attenuation bottlenecks, etc., to reduce self- Quenching phenomenon, beneficial to evaporation, reducing the effect of direct action

Inactive Publication Date: 2014-08-06
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although various optimizations have been made to the FIrpic OLED structure, and the device performance has been greatly improved, the biggest weakness of FIrpic is that the blue light emitted by FIrpic is sky blue, and the color purity of the blue light is not good. The CIE of each OLED device produced It varies between (0.13~0.17,0.29~0.39), which is a big gap with the standard Blu-ray CIE (0.137,0.084)
[0007] People's research on iridium metal complexes of organic electroluminescent materials has been in-depth, but blue light-emitting materials have always had bottlenecks in terms of luminous color purity, luminous efficiency, and device efficiency attenuation.

Method used

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  • Blue light-emitting organic electroluminescent material, its preparation method and organic electroluminescent device
  • Blue light-emitting organic electroluminescent material, its preparation method and organic electroluminescent device
  • Blue light-emitting organic electroluminescent material, its preparation method and organic electroluminescent device

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preparation example Construction

[0040] The preparation method of the above-mentioned blue-light organic electroluminescent material comprises the following steps:

[0041] S1. In an oxygen-free environment (in the present invention, the oxygen-free environment is at least one of nitrogen and argon, preferably nitrogen, the same below), the structural formula is Compound A (due to the different substituent groups of R, its chemical name is different, please refer to each embodiment for details, the same below) and the structural formula is Compound B (3,5-difluoro-4-cyanophenylboronic acid) was dissolved in a solvent, and tetrabutylammonium bromide, base and palladium catalyst, which played a phase transfer role, were added to the solvent, and the Suzuki reflux coupling reaction 4 ~ 10h, stop the reaction, obtain the structural formula after separation and purification treatment: Compound C; wherein, the molar ratio of compound A to compound is 1:1.2, and the molar weight of tetrabutylammonium bromide is 0....

Embodiment 1

[0051] Example 1: Complex bis(3-(3',5'-difluoro-4'-cyanophenyl)pyridazine-N,C 2 ') Synthesis of (2-pyridyl) iridium

[0052] (1) Synthesis of 3-(3',5'-difluoro-4'-cyanophenyl)pyridazine

[0053]

[0054] Under nitrogen protection, 3.18g (20mmol) 3-bromopyridazine, 4.39g (24mmol) 3,5-difluoro-4-cyanophenylboronic acid, 80mL DMF, 20mL water, 3.22g (10mmol) tetrabutyl bromide Ammonium chloride (TBTA), 5.53g (40mmol) anhydrous potassium carbonate, 0.23g (0.2mmol) tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ), stirred and refluxed for 4h. After the reaction solution was cooled to room temperature, it was extracted with dichloromethane, separated, washed with water until neutral, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was distilled off the solvent under reduced pressure to obtain the crude product. Silica gel column chromatography was carried out with dichloromethane as the eluent. After drying, 2.95 g of solid was obtained with...

Embodiment 2

[0075] Example 2: Complex bis(3-(3',5'-difluoro-4'-cyanophenyl)-6-methylpyridazine-N,C 2 ') Synthesis of (2-pyridyl) iridium

[0076] (1) Synthesis of 3-(3',5'-difluoro-4'-cyanophenyl)-6-methylpyridazine

[0077]

[0078] Under nitrogen protection, 3.46g (20mmol) 3-bromo-6-methylpyridazine, 4.39g (24mmol) 3,5-difluoro-4-cyanophenylboronic acid, 80mL N,N-dimethylformamide , 20mL of water, 3.22g (10mmol) of tetrabutylammonium bromide, 8.48g (80mmol) of anhydrous sodium carbonate, 1.15g (1mmol) of tetrakis (triphenylphosphine) palladium, stirred and refluxed for 4h. After the reaction solution was cooled to room temperature, it was extracted with dichloromethane, separated, washed with water until neutral, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was distilled off the solvent under reduced pressure to obtain the crude product. Silica gel column chromatography was carried out with dichloromethane as the eluent. After drying, 3.00 g of solid ...

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Abstract

The invention belongs to the field of organic electroluminescent materials and discloses a blue light-emitting organic electroluminescent material and its preparation method and use. The blue light-emitting organic electroluminescent material has a general structural formula shown in the description, and in the formula, R represents hydrogen atom, alkyl or alkoxy. The blue light-emitting organic electroluminescent material comprises 3-phenylpyridazine as a ring metal ligand main structure and also comprises hydrogen atom, alkyl or alkoxy so that satisfactory energy transmission efficiency and blue light emission wavelength are obtained and a certain steric-hinerance effect is produced and thus direct effect between metal atoms is reduced and triplet exciton self-quenching phenomenon is reduced. Two F substituent groups on the phenyl ring effectively realize blue shift of emission wavelength and improve luminescence performances.

Description

technical field [0001] The invention relates to an organic electroluminescent material, in particular to a blue light organic electroluminescent material and a preparation method thereof. The invention also relates to an organic electroluminescence device using the blue light organic electroluminescence material as a light-emitting layer material. Background technique [0002] Organic electroluminescence refers to a luminescence phenomenon in which organic materials directly convert electrical energy into light energy under the action of an electric field. In the early days, the research on organic electroluminescence was stagnant because of the high driving voltage and low luminous efficiency of organic electroluminescent devices. Until 1987, people such as Tang of American Kodak Company invented 8-hydroxyquinoline aluminum (Alq 3 ) is a light-emitting material, and a uniform and dense high-quality thin film is made with aromatic diamines, and an organic electroluminescen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F15/00H01L51/54
Inventor 周明杰王平张娟娟张振华
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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