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Red phosphorescence iridium complexes, preparing 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 low efficiency and difficulty in obtaining satisfactory luminescent performance

Inactive Publication Date: 2014-12-03
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

However, the efficiency of the current red phosphorescence luminescent materials is relatively low, and it is difficult to obtain satisfactory luminescent performance when they are applied to electroluminescent devices.

Method used

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  • Red phosphorescence iridium complexes, preparing method thereof and organic electroluminescence device
  • Red phosphorescence iridium complexes, preparing method thereof and organic electroluminescence device
  • Red phosphorescence iridium complexes, preparing method thereof and organic electroluminescence device

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preparation example Construction

[0052] see figure 1 , the preparation method of the red phosphorescence iridium metal complex of an embodiment, comprises the steps:

[0053] Step S110: In the first inert gas atmosphere, Ar-Br and acenaphthyl-5-boronic acid are dissolved in the first solvent at a molar ratio of 4:4.5-5, and a catalyst and a carbonate solution are added to carry out a Suzuki coupling reaction After 8-12 hours, after separation and purification, the ring metal main ligand acenaphthyl-5-ylbenzodiazepine six-membered ring is obtained.

[0054] Wherein, Ar is phthalazine, cinnoline, benzopyrimidine or quinoxaline.

[0055] The first inert gas is argon, helium or neon.

[0056] The first solvent is toluene or tetrahydrofuran. The amount of the first solvent is suitable to fully dissolve Ar-Br and acenaphthylene-5-boronic acid. The catalyzer is a palladium catalyst, preferably tetrakistriphenylphosphine palladium (Pd(pph 3 ) 4 ) or palladium dichlorobistriphenylphosphine (PdCl 2 (PPh 3 ) 2 ...

Embodiment 1

[0088] Red Phosphorescent Bis[1-(Acenaphthyl-5-yl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex synthesis.

[0089] Red Phosphorescent Bis[1-(Acenaphthyl-5-yl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex has the following structural formula:

[0090]

[0091] (1) Synthesis of 1-(acenaphthyl-5-yl)phthalazine

[0092]In an argon atmosphere, 0.84g (4mmol) of 1-bromophthalazine, 0.95g (4.8mmol) of acenaphthene-5-boronic acid and 0.23g (0.20mmol) of tetrakistriphenylphosphine palladium were dissolved in 30mL of toluene, followed by 10 mL of an aqueous solution containing 0.85 g (8 mmol) of sodium carbonate was added dropwise to the reaction system. Heated and stirred under reflux for Suzuki coupling reaction for 10h. After the reaction is complete, the reaction solution is naturally cooled to room temperature, extracted several times with an appropriate amount of water and ethyl acetate, the organic phase is dried wi...

Embodiment 2

[0121] Red phosphorescent bis[3-(acenaphthyl-5-yl)cinnoline-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex synthesis.

[0122] Red phosphorescent bis[3-(acenaphthyl-5-yl)cinnoline-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex has the following structural formula:

[0123]

[0124] (1) Synthesis of 3-(acenaphthyl-5-yl)cinnoline

[0125] In a helium atmosphere, 0.84g (4mmol) of 3-bromocinnoline, 0.99g (5mmol) of acenaphthylene-5-boronic acid and 0.28g (0.24mmol) of tetraphenylphosphine palladium were dissolved in 25mL of tetrahydrofuran, followed by the reaction 10 mL of an aqueous solution containing 1.38 g (10 mmol) of potassium carbonate was added dropwise to the system. Heated and stirred under reflux for Suzuki coupling reaction for 12h. After the reaction was complete, the reaction solution was naturally cooled to room temperature, and extracted several times with appropriate amount of water and ethyl acetate. The organic phase was ...

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Abstract

The invention relates to red phosphorescence iridium complexes, a preparing method thereof and an organic electroluminescence device. The structure formula of the red phosphorescence iridium complexes is shown in the specification, wherein -Ar is shown in the specification. The red phosphorescence iridium complexes introduce 5-acenaphthenyl into a benzodinitrogen six-membered ring, can obtain a satisfied red light emitting wavelength, and generate steric-hindrance effects to a certain degree, thus reducing direct functions of iridium atoms, reducing self-quenching phenomena of triplet excitons and having strong phosphorescence emission at room temperature. In addition, the red phosphorescence iridium complexes are respectively provided with acenaphthenyl and a benzodinitrogen six-membered ring structure that are high in planar rigidity, thus facilitating phosphorescence luminescence on the one hand, effectively controlling the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels of the materials on the other hand, and facilitating charge transfer in balancing devices. Electroluminescence properties of the organic electroluminescence device can be improved by applying the complexes into 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 周明杰王平张娟娟冯小明
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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