Organic electro-phosphorescent material and preparation method thereof, and organic electroluminescent device

A phosphorescent material and electromechanical technology, applied in the field of phosphorescent materials, can solve the problems of the luminous color purity of blue-light phosphorescent materials, the efficiency attenuation bottleneck of luminous efficiency devices, etc.

Inactive Publication Date: 2015-02-11
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] People's research on iridium metal complexes of organic electrophosphorescent materials has been in-depth, but there are bottlenecks in the luminous color purity, luminous efficiency and device efficiency decay of blue phosphorescent materials.

Method used

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  • Organic electro-phosphorescent material and preparation method thereof, and organic electroluminescent device
  • Organic electro-phosphorescent material and preparation method thereof, and organic electroluminescent device
  • Organic electro-phosphorescent material and preparation method thereof, and organic electroluminescent device

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preparation example Construction

[0038] The preparation process of the organic electrophosphorescent material of the present invention is roughly divided into the following steps:

[0039] (1) Compound E and Compound F are synthesized by Suzuki coupling reaction; Compound F is 2,4-

[0040] The structural formulas of difluoro-3-cyanophenylboronic acid, compound E and compound C are as follows:

[0041] Compound E is Compound C is Among them, the R group is a phenyl group, a fluorenyl group, or a carbazole group.

[0042] (2) The compound C obtained in step (1) is reacted with compound D to form a chlorine bridged dimer, namely compound A. Among them, compound D is iridium trichloride trihydrate IrCl 3 ·3H 2 O. The structural formula of compound A is as follows:

[0043]

[0044] (3) Using compound A prepared in step (2) as the main structure of the cyclometal ligand, 2,4-bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole (ie compound B) ) Is used as an auxiliary ligand source to react compound A and compound B to obta...

Embodiment 1

[0050] The organic electroluminescent material (P) disclosed in this embodiment is the complex bis(2-(4',6'-difluoro-5'-cyanophenyl)-5-phenylpyrimidine-N,C 2' )(2,4-Bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole)iridium, its structural formula is as follows:

[0051]

[0052] It is prepared by the following steps:

[0053] (1) Synthesis of 2-(2',4'-difluoro-3'-cyanophenyl)-5-phenylpyrimidine

[0054] The synthesis reaction formula of 2-(2',4'-difluoro-3'-cyanophenyl)-5-phenylpyrimidine is as follows:

[0055]

[0056] The specific steps are: under the protection of nitrogen, 2.35g (10mmol) 2-bromo-5-phenylpyrimidine, 2.20g (12mmol) 2,4-difluoro-3-cyanophenylboronic acid and 0.58g (0.5mmol) Tetrakis(triphenylphosphorus) palladium (ie, palladium catalyst) is dissolved in 50 mL of toluene, and then 25 mL of an aqueous solution containing 2.76 g (20 mmol) of potassium carbonate is added dropwise to the reaction system. The reaction was stirred for 10 hours under heating to 100°C. After ...

Embodiment 2

[0070] The organic electro-phosphorescent material disclosed in this embodiment is bis(2-(4',6'-difluoro-5'-cyanophenyl)-4-(fluorene-9'-yl)pyrimidine-N,C 2' )(2,4-Bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole)iridium, its structural formula is as follows:

[0071]

[0072] It is prepared by the following steps:

[0073] (1) Synthesis of 2-(2',4'-difluoro-3'-cyanophenyl)-4-(fluorene-9'-yl)pyrimidine

[0074] The synthesis reaction formula of 2-(2',4'-difluoro-3'-cyanophenyl)-4-(fluorene-9'-yl)pyrimidine is as follows:

[0075]

[0076] The specific steps are: under the protection of nitrogen, 3.23g (10mmol) 2-bromo-4-(fluorene-9'-yl)pyrimidine, 1.83g (10mmol) 2,4-difluoro-3-cyanophenylboronic acid and 0.21g (0.3mmol) of bischlorobis(triphenylphosphorus) palladium was dissolved in 60mL of N,N-dimethylformamide solution (ie DMF), and then 30mL containing 1.59g (15mmol) of carbonic acid was added dropwise to the reaction system An aqueous solution of sodium. The reaction was stirred fo...

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Abstract

The invention provides an organic electro-phosphorescent material and a preparation method thereof, and an organic electroluminescent device. The invention provides the organic electro-phosphorescent material with the general formula (P), wherein R group is phenyl group, fluorenyl group, or carbazolyl group. The organic electro-phosphorescent material (P) is an iridium metal complex synthesized with 2-(2',4'-difluoro-3'-cyanophenyl)pyrimidine as a cyclo-metal ligand and with 2,4-bis(trifluoromethyl)-5-(pyridin-2'-yl)pyrrole as a subsidiary ligand. According to the organic electro-phosphorescent material, the adjustment upon material luminescent colors is realized through introducing chemical modifications of phenyl group, fluorenyl group or carbazole group to the pyrimidine ring of the cyclo-metal ligand, such that high-luminous-efficiency blue phosphorescent emission is obtained.

Description

Technical field [0001] The invention relates to the field of phosphorescent materials, in particular to an organic electroluminescent material. The invention also relates to a preparation method of the organic electroluminescent material and its application in organic electroluminescent devices. 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 at a standstill due to the high driving voltage and low luminous efficiency of organic electroluminescence devices. Until 1987, Tang et al. of Kodak in the United States invented the use of 8-hydroxyquinoline aluminum (Alq3) as a luminescent material, and an aromatic diamine to make a uniform and dense high-quality film, which produced a low working voltage, high brightness, High-efficiency organic electrolumine...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F15/00H01L51/54
Inventor 周明杰王平张娟娟黄辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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