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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 fields of electric solid-state devices, organic chemistry, luminescent materials, etc., can solve the problems of color purity and backwardness that are rarely achieved in deep red and deep green light

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

[0042] see figure 1 , a preparation method of a red phosphorescent iridium metal complex, comprising the following steps.

[0043] S110: In the first protective gas atmosphere, dissolve compound A and lithium diisopropylamide in the first solvent, react at -78°C for 1h to 2h to obtain an intermediate reaction liquid, and add ethyl trifluoroacetate to the intermediate reaction liquid The ester was reacted at -78°C for 1h to 2h, and compound B was obtained after separation and purification.

[0044] Compound A and lithium diisopropylamide ( ) in a molar ratio of 1:1.1 to 1.3, and the molar ratio of ethyl trifluoroacetate to lithium diisopropylamide is 1:1.

[0045] The structural formula of compound A is: The structural formula of compound B is: R is hydrogen or methyl. When R is a methyl group, R can replace the hydrogen on the 3-, 4-, 5-, 6-, 7- or 8-position of the isoquinoline ring. For example, compound B can specifically be 1-(4'-trifluoroacetylphenyl) isoquinolin...

Embodiment 1

[0083] Red Phosphorescent Iridium Metal Complex Bis[1-(4'-trifluoroacetylphenyl)isoquinoline-N,C 2 '] (acetylacetonate) iridium synthesis.

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

[0085]

[0086] At -78°C, in a nitrogen atmosphere, 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 In the mixed solution composed of tetrahydrofuran, stir and react for 1 h to obtain an intermediate reaction solution. A mixture consisting of 1.43 mL (12 mmol) of ethyl trifluoroacetate and 5 mL of tetrahydrofuran was added dropwise to the intermediate reaction solution, and the reaction system was maintained at -78° C., and stirred for 1 h. After the reaction was completed, the reaction system was naturally raised to 0°C, stirred and reacted for 0.5 h, then an appropriate amount of saturated ammonium chloride aqueous solution was added, and ...

Embodiment 2

[0108] Red Phosphorescent Iridium Metal Complex Bis[1-(4'-trifluoroacetylphenyl)-3-methylisoquinoline-N,C 2 '] (acetylacetonate) iridium synthesis.

[0109] (1) Synthesis of ligand 1-(4'-trifluoroacetylphenyl)-3-methylisoquinoline

[0110]

[0111] At -78°C, under a nitrogen atmosphere, 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 diisopropylamine Lithium base and 10mL of tetrahydrofuran in a mixed solution, stirred for 1 h to obtain an intermediate reaction solution. A mixture consisting of 1.43 mL (12 mmol) of ethyl trifluoroacetate and 5 mL of tetrahydrofuran was added dropwise to the intermediate reaction solution, and the reaction system was maintained at -78° C., and stirred for 1 h. After the reaction system naturally rose to 0°C, stirred and reacted for 0.5 h, an appropriate amount of saturated ammonium chloride aqueous solution was added, extracted with ethyl acetate, an...

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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 is a different-ligand type iridium complex using 1-(4'-trifluoroacetylphenyl)isoquinoline as the main structure of a cyclometalated ligand and acetylacetone as an ancillary ligand; an isoquinoline ring is an optimal structure option of the cyclometalated main ligand of a red phosphorescent material and can guarantee that the material emits light at red bands; as the methyl group is introduced on the isoquinoline ring, certain steric hindrance effect can be produced, direct action among metal atoms and self-quenching of triplet exciton can be reduced and the luminous efficiency of material can be improved. Thus, as the red phosphorescent iridium complex is applied to the organic electroluminescence device, the luminescence performance of the organic electroluminescence device can be improved.

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): 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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