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Red phosphorescent iridium complex and preparation method thereof, and organic electroluminescence device

A technology of iridium metal complexes and red phosphorescence, applied in the field of its preparation, organic electroluminescence devices, red phosphorescence iridium metal complexes, can solve the backwardness, rarely achieve the color purity of deep red light and dark green light, etc. question

Inactive Publication Date: 2015-05-27
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

Generally speaking, the development of blue phosphorescent materials always lags behind red light and green light. In terms of color purity alone, blue phosphorescent materials have rarely been able to achieve the same level as deep red light and deep green light. color purity

Method used

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  • Red phosphorescent iridium complex and preparation method thereof, and organic electroluminescence device
  • Red phosphorescent iridium complex and preparation method thereof, and organic electroluminescence device
  • Red phosphorescent iridium complex and preparation method thereof, and organic electroluminescence device

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preparation example Construction

[0074] The preparation method of the red phosphorescent iridium metal complex has mild reaction conditions, low equipment requirements, low preparation cost, and easy large-scale preparation.

[0075] see figure 2 , an organic electroluminescent device 300 according to one embodiment, comprising a conductive anode substrate 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, an electron injection buffer layer 306 and a cathode 307 stacked in sequence .

[0076] Materials for the conductive anode substrate 301 , the hole transport layer 302 , the hole blocking layer 304 , the electron transport layer 305 , the electron injection buffer layer 306 and the cathode 307 are commonly used materials in the art. For example, the conductive anode substrate 301 is indium tin oxide (ITO) conductive glass, and the material of the hole transport layer 302 is N,N'-bis(1-naphthyl)-N,N'-diphenyl-p-diaminobiphenyl (NPB), th...

Embodiment 1

[0081] Red Phosphorescent Bis[1-(4'-trifluoroacetylphenyl)isoquinoline-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex synthesis.

[0082] Red Phosphorescent Bis[1-(4'-trifluoroacetylphenyl)isoquinoline-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex has the following structural formula:

[0083]

[0084] (1) Synthesis of 1-(4'-trifluoroacetylphenyl)isoquinoline

[0085]In a nitrogen atmosphere at -78°C, 5 mL of a tetrahydrofuran solution containing 2.84 g (10 mmol) of 1-(4'-bromophenyl) isoquinoline was added to 1.29 g (12 mmol) of lithium diisopropylamide and 10 mL of tetrahydrofuran in a mixed solution, stirred for 1 h to obtain a mixture containing an intermediate product. A mixed solution consisting of 1.43 mL (12 mmol) of ethyl trifluoroacetate and 5 mL of tetrahydrofuran was added dropwise to the above-mentioned mixture containing the intermediate product, and the reaction system was kept at -78° C., and stirred for 1 h. After the re...

Embodiment 2

[0111] Red phosphorescent bis[1-(4'-trifluoroacetylphenyl)-3-methylisoquinoline-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex synthesis.

[0112] Red phosphorescent bis[1-(4'-trifluoroacetylphenyl)-3-methylisoquinoline-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex has the following structural formula:

[0113]

[0114] (1) Synthesis of 1-(4'-trifluoroacetylphenyl)-3-methylisoquinoline

[0115] In an argon atmosphere at -78°C, 5 mL of a tetrahydrofuran solution containing 2.98 g (10 mmol) of 1-(4'-bromophenyl) 3-methylisoquinoline was added to 1.29 g (12 mmol) of diisoquinoline In a mixed solution composed of lithium propylamide and 10 mL of tetrahydrofuran, the reaction was stirred for 1 h to obtain a mixture containing an intermediate product. A mixed solution consisting of 1.43 mL (12 mmol) of ethyl trifluoroacetate and 5 mL of tetrahydrofuran was added dropwise to the above-mentioned mixture containing the intermediate product, and th...

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Abstract

The invention relates to a red phosphorescent iridium complex and a preparation method thereof, and an organic electroluminescence device. The red phosphorescent iridium complex has a structural formula as described in the specification; and in the formula, R is hydrogen or a methyl group. The red phosphorescent iridium complex uses 1-(4'-trifluoroacetylphenyl)isoquinoline as the main structure of a cyclometalated ligand and 2,2,6,6-tetramethyl-3,5-heptadione as an ancillary ligand; an isoquinoline ring can emit light at red bands; the methyl groups on the isoquinoline ring produce different electronic effects at different C positions, thereby realizing emission of red light of different wave lengths, exerting steric hindrance effect, reducing direct action among metal atoms and self-quenching of triplet exciton and improving the luminous efficiency of materials; and relative to hydrogen atoms, introduction of a trifluoroacetyl group on a benzene ring enables molecular vibration energy to be reduced and the luminous efficiency and intensity of the red phosphorescent iridium complex to be improved. The red phosphorescent iridium complex can improve the luminescence performance of the organic electroluminescence device.

Description

technical field [0001] The invention relates to the technical field of electroluminescence materials, in particular to a red phosphorescent iridium metal complex, a preparation method thereof and an organic electroluminescence device. 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 ...

Claims

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Application Information

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