Blue light-emitting organic electroluminescent material and its preparation method and use

A luminescent and electromechanical technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of blue light luminescent material luminous color purity, luminous efficiency device efficiency attenuation bottleneck, etc., to reduce self-quenching phenomenon, improve Luminescence performance, effect of blue-shifted emission wavelength

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

[0008] 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 and its preparation method and use
  • Blue light-emitting organic electroluminescent material and its preparation method and use
  • Blue light-emitting organic electroluminescent material and its preparation method and use

Examples

Experimental program
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preparation example Construction

[0044] The preparation method of the above-mentioned blue-light organic electroluminescent material comprises the following steps:

[0045] S1, under the protection of an inert gas (the inert gas of the present invention includes nitrogen, argon or a mixed gas of nitrogen and argon, similar to the following), 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 (2,4-difluoro-3-cyanophenylboronic acid) was added to the second phase containing tetrabutylammonium bromide (TBTA), base and rake catalyst at a molar ratio of 1:1.2. In a solvent, a mixed solution is obtained, then the mixed solution is heated to reflux, stirred and reacted for 4-10 hours, and after cooling to room temperature, the reaction solution is separated and purified to obtain the structural formula: Compound C (due to the different substituent ...

Embodiment 1

[0067] Example 1: Complex bis(3-(4',6'-difluoro-5'-cyanophenyl)pyridazine-N,C 2 ') (tetrakis (1-pyrazole) boron) synthesis of iridium

[0068] (1) Synthesis of 3-(2',4'-difluoro-3'-cyanophenyl)pyridazine

[0069]

[0070] Under nitrogen protection, 3.18g (20mmol) 3-bromopyridazine, 4.39g (24mmol) 2,4-difluoro-3-cyanophenylboronic acid, 80mL toluene, 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, 3.08 g of s...

Embodiment 2

[0091] Example 2: Complex bis(3-(4',6'-difluoro-5'-cyanophenyl)pyridazine-N,C 2 ') Synthesis of (3-trifluoromethyl-5-(pyridin-2'-yl)-1,2,4-triazole) iridium

[0092] (1) The synthetic steps of 3-(2',4'-difluoro-3'-cyanophenyl)pyridazine refer to Example 1;

[0093] (2) The synthesis steps of the iridium-containing dichloro dimer whose ligand is 3-(2',4'-difluoro-3'-cyanophenyl)pyridazine refer to Example 1;

[0094] (3) Complex bis(3-(4',6'-difluoro-5'-cyanophenyl)pyridazine-N,C 2 ') Synthesis of (3-trifluoromethyl-5-(pyridin-2'-yl)-1,2,4-triazole) iridium

[0095]

[0096] Under nitrogen protection, 0.64g (3mmol) 3-trifluoromethyl-5-(pyridin-2-yl)-1,2,4-triazole and 1.32g (1mmol) ligand were 3-(2', The iridium-containing dichloro dimer of 4'-difluoro-3'-cyanophenyl)pyridazine was dissolved in 60mL of 1,2-dichloroethane, under the catalysis of 0.54g (10mmol) sodium methoxide, stirred and heated The temperature was raised to reflux, and the reaction was carried out for 1...

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Abstract

The invention belongs to the field of organic semiconductor 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 structure shown in the formula, and in the formula, R represents hydrogen atom, C1-C6 alkyl or C1-C6 alkoxy and LX represents an auxiliary ligand in the iridium complex. The blue light-emitting organic electroluminescent material comprises 3-phenylpyridazine as a ring metal ligand main structure and also comprises alkyl and 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 and cyano substituent groups on the phenyl ring effectively realize blue shift of emission wavelength, improve luminescence performances, are conducive to vapor plating, and improve film-forming property and device stability.

Description

technical field [0001] The invention relates to an organic semiconductor material, in particular to a blue-light organic electroluminescence material and a preparation method and application thereof. 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 electroluminescent device with low operating voltage, high brightness, and high efficiency is prepared, which opens a new prelude to the research on organic electrolumi...

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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