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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 electric solid devices, organic chemistry, light-emitting materials, etc., can solve the problems of difficult to obtain satisfactory light-emitting performance and low efficiency

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

[0035] see figure 1 , the preparation method of the red phosphorescent iridium metal complex of an embodiment, comprises the steps:

[0036] Step S110: In the first inert gas atmosphere, dissolve 1-R-4-bromophthalazine and acenaphthylene-5-boronic acid in the first solvent with a molar ratio of 4:4.8~5, and add catalyst and carbonate solution , carry out Suzuki coupling reaction for 8 to 12 hours, and obtain ring metal main ligand 1-R-4-(acenaphthyl-5-yl)phthalazine after separation and purification.

[0037] Among them, -R is the general formula -C n h 2n+1 Alkyl, the general formula is -OC n h 2n+1 alkoxy, phenyl or phenoxy, n is an integer of 1-20.

[0038] The general formula is -C n h 2n+1 The alkyl group is straight-chain or branched-chain. The general formula is -OC n h 2n+1 The alkoxy group is a straight chain alkoxy group or a branched chain alkoxy group.

[0039] The first inert gas is argon, helium or neon.

[0040] The first solvent is toluene or tetrah...

Embodiment 1

[0073] Red Phosphorescent Bis[1-Methyl-4-(Acenaphthyl-5-yl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex synthesis.

[0074] Red Phosphorescent Bis[1-Methyl-4-(Acenaphthyl-5-yl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex has the following structural formula:

[0075]

[0076] (1) Synthesis of 1-methyl-4-(acenaphthyl-5-yl)phthalazine

[0077]In an argon atmosphere, 0.89 g (4 mmol) of 1-methyl-4-bromophthalazine, 0.95 g (4.8 mmol) of acenaphthylene-5-boronic acid and 0.23 g (0.20 mmol) of tetrakistriphenylphosphine palladium were dissolved in 30 mL In toluene, then 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 10 h. 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 i...

Embodiment 2

[0109] Red phosphorescent bis[1-methoxy-4-(acenaphthyl-5-yl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex synthesis.

[0110] Red phosphorescent bis[1-methoxy-4-(acenaphthyl-5-yl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium complex has the following structural formula:

[0111]

[0112] (1) Synthesis of 1-methoxy-4-(acenaphthyl-5-yl)phthalazine

[0113] In a neon atmosphere, dissolve 0.96g (4mmol) of 1-methoxy-4-bromophthalazine, 0.99g (5mmol) of acenaphthene-5-boronic acid and 0.28g (0.24mmol) of palladium tetrakistriphenylphosphine in 25mL In THF, 10 mL of an aqueous solution containing 1.38 g (10 mmol) of potassium carbonate was then added dropwise to the reaction system, heated, and stirred under reflux for 12 h. 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 with a...

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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 -R is alkyl having a general formula of -CnH<2n+1>, alkoxy having a general formula of -OCnH<2n+1>, benzyl or phenoxyl, and the n is an integer ranging from 1 to 20. The red phosphorescence iridium complexes have strong phosphorescence emission at room temperature. Introduction of the alkyl of different chain lengths and the alkoxy of different chain lengths can increase solubility of the materials in organic solvents and control light-emitting wavelengths of the materials. The red phosphorescence iridium complexes are respectively provided with acenaphthenyl and a phthalazine ring structure that are high in planar rigidity, and the benzyl and the phenoxyl which are large groups are also introduced, thus facilitating phosphorescence luminescence, controlling the highest occupied molecular orbital and the lowest unoccupied molecular orbital energy levels of the materials, facilitating charge transfer in balancing devices, and improving electroluminescence properties of the device.

Description

technical field [0001] The invention relates to the technical field of electroluminescence materials, in particular to a red phosphorescence 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 周明杰王平张娟娟张振华
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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