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

A phosphorescent material, electrophosphorescence technology, applied in luminescent materials, electro-solid devices, organic chemistry, etc., to reduce the probability of non-radiative transitions, improve luminous efficiency, and increase solubility

Inactive Publication Date: 2015-02-11
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

However, due to the limitation of spin statistics theory, the theoretical internal quantum efficiency limit of fluorescent materials is only 25%. How to make full use of the remaining 75% of phosphorescence to achieve higher luminous efficiency has become a hot research direction in this field since then.

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 present invention also relates to a method for preparing the above-mentioned organic electro-phosphorescent material. The method sequentially includes the following steps:

[0039] 1. Make compound E and compound F through Suzuki coupling reaction to synthesize compound C; wherein, compound F is 2,3,4-trifluorophenylboronic acid, and the structural formulas of compound E and compound C are as follows:

[0040] Compound E is Compound C is

[0041] 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:

[0042]

[0043] 3. The compound A prepared in step 2 is used as the main structure of the cyclometal ligand, and potassium tetrakis (1-pyrazole) boride (compound B) is used as an auxiliary ligand source, and compound A and compound B are reacted to obtain iridium Metal complexes, namely o...

Embodiment 1

[0051] The organic electrophosphorescent material disclosed in this embodiment is the complex bis(2-(4′,5′,6′-trifluorophenyl)pyrimidine-N,C 2 ′) (Tetra(1-pyrazole) boron) iridium, its structural formula is as follows:

[0052]

[0053] It is prepared by the following steps:

[0054] (1) Synthesis of 2-(2′,3′,4′-trifluorophenyl)pyrimidine

[0055] The synthetic reaction formula is as follows:

[0056]

[0057] The specific steps are: under a nitrogen atmosphere, 1.59g (10mmol) 2-bromopyrimidine, 2.11g (12mmol) 2,3,4-trifluorophenylboronic acid and 0.58g (0.5mmol) tetrakis(triphenylphosphorus) 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, heated, and stirred at 100°C for 6h. After the reaction solution was cooled to room temperature, use dichloromethane Extract, separate, wash with water to neutrality, then dry with anhydrous magnesium sulfate, then filter, th...

Embodiment 2

[0073] The organic electrophosphorescent material disclosed in this embodiment is a complex complex bis(2-(4′,5′,6′-trifluorophenyl)-5-methylpyrimidine-N,C 2 ′) (Tetra(1-pyrazole) boron) iridium, its structural formula is as follows:

[0074]

[0075] It is prepared by the following steps:

[0076] (1) Synthesis of 2-(2′,3′,4′-trifluorophenyl)-5-methylpyrimidine

[0077] The synthetic reaction formula is as follows:

[0078]

[0079] The specific steps are: under a nitrogen atmosphere, 1.73g (10mmol) 2-bromo-5-methylpyrimidine, 1.76g (10mmol) 2,3,4-trifluorophenylboronic acid and 0.28g (0.4mmol) dichlorobis (Triphenylphosphorus) palladium was dissolved in 50 ml of DMF, and then 25 ml of an aqueous solution containing 3.18 g (30 mmol) of sodium carbonate was added dropwise to the reaction system. Heat to 90°C and stir for 8 hours. After the reaction solution is cooled to room temperature, extract with dichloromethane, separate the layers, wash with water to neutrality, dry with anhydr...

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Abstract

The invention relates to an organic electro-phosphorescent material and a preparation method thereof, and an organic electroluminescent device. The organic electro-phosphorescent material (P) has a following structure, wherein R is H or C1-C20 straight-chain or branched-chain alkyl. According to the organic electro-phosphorescent material, a blue-light organic electro-phosphorescent material iridium metal complex is synthesized with 2-(2',3',4'-trifluorophenyl)pyrimidine as a cyclo-metal ligand and with tetra(1-pyrazolyl)boron as a subsidiary ligand. 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 electro-phosphorescent 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 electrolumin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F19/00H01L51/54
Inventor 周明杰王平张娟娟陈吉星
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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