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

A phosphorescent material and electromechanical technology, applied in luminescent materials, electrical solid devices, organic chemistry, etc., can solve problems such as the purity of blue light phosphorescent materials, the bottleneck of luminous efficiency device efficiency attenuation, 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) Synthesize compound C through Suzuki coupling reaction of compound E and compound F; wherein, compound F is 2,4-difluoro-3-cyanophenylboronic acid, and the structural formulas of compound E and compound C are as follows:

[0040] Compound E is Compound C is Among them, R is C 1 ~C 20 straight-chain or branched-chain alkyl groups, or hydrogen atoms;

[0041] (2) Reaction of compound C prepared in step (1) with compound D to generate a chlorine-bridged dimer, namely compound A. Wherein, compound D is trihydrate iridium trichloride IrCl 3 ·3H 2 O. The structural formula of compound A is as follows:

[0042]

[0043] (3) Compound A prepared in step (2) is used as the main structure of the ring metal ligand, and 2,4-bis(trifluoromethyl)-5-(pyridin-2'-yl)pyrrole (ie compound B ) is used as an auxiliary ligand so...

Embodiment 1

[0049] The organic electrophosphorescent material (P) disclosed in this example is the complex bis(2-(4',6'-difluoro-5'-cyanophenyl)pyrimidine-N,C 2' )(2,4-bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole)iridium, its structural formula is as follows:

[0050]

[0051] It is prepared by the following steps:

[0052] (1) Synthesis of 2-(2',4'-difluoro-3'-cyanophenyl)pyrimidine,

[0053] The synthetic reaction formula of 2-(2',4'-difluoro-3'-cyanophenyl)pyrimidine is as follows:

[0054]

[0055] The specific steps are: under the protection of nitrogen, mix 1.59g (10mmol) 2-bromopyrimidine, 2.20g (12mmol) 2,4-difluoro-3-cyanophenylboronic acid and 0.58g (0.5mmol) tetrakis (triphenyl Phosphorus) palladium was dissolved in 40mL of toluene, and then 20mL of an aqueous solution containing 2.76g (20mmol) of potassium carbonate was added dropwise to the reaction system. Heat to 100°C and stir the reaction for 6h. After the reaction solution was cooled to room temperature, it w...

Embodiment 2

[0071] The organic electrophosphorescent material disclosed in this example is the complex bis(2-(4',6'-difluoro-5'-cyanophenyl)-5-methylpyrimidine-N,C 2' )(2,4-bis(trifluoromethyl)-5-(pyridine-2',-yl)pyrrole)iridium, its structural formula is as follows:

[0072]

[0073] It is prepared by the following steps:

[0074] (1) Synthesis of 2-(2',4'-difluoro-3'-cyanophenyl)-5-methylpyrimidine

[0075] The synthetic reaction formula of 2-(2',4'-difluoro-3'-cyanophenyl)-5-methylpyrimidine is as follows:

[0076]

[0077] The specific steps are: under nitrogen protection, mix 1.73g (10mmol) 2-bromo-5-methylpyrimidine, 1.83g (10mmol) 2,4-difluoro-3-cyanophenylboronic acid and 0.28g (0.4mmol) Dichlorobis(triphenylphosphine)palladium was dissolved in 50mL of N,N-dimethylformamide solution, and then 25mL of an aqueous solution containing 3.18g (30mmol) of sodium carbonate was added dropwise to the reaction system. Heated to 90°C and stirred for 8h. After the reaction solution w...

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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 is C1-C20 straight-chain or branched-chain alkyl, or hydrogen atom. 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 (P), the adjustment upon material luminescent colors is realized through introducing alkyl chain chemical modification 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 luminescent materials, in particular to an organic electrophosphorescent material. The invention also relates to the 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 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 brightnes...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342
Inventor 周明杰王平张娟娟黄辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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