Iridium complex, application thereof and OLED (organic light-emitting device)

A technology of iridium complexes and compounds, which is applied in the field of organic electroluminescent devices, can solve problems affecting device life and efficiency, and organic materials are prone to crystallization, and achieve good thermal stability, high luminous purity, and high luminous efficiency.

Inactive Publication Date: 2018-05-11
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, when the OLED device is operated with an applied voltage, it will generate Joule heat, which makes the organic material easy to crystallize, which affects the life and efficiency of the device. Therefore, it is also necessary to develop stable and efficient organic electroluminescent materials.

Method used

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  • Iridium complex, application thereof and OLED (organic light-emitting device)
  • Iridium complex, application thereof and OLED (organic light-emitting device)
  • Iridium complex, application thereof and OLED (organic light-emitting device)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Synthetic route of compound 1

[0049]

[0050] The synthetic method of intermediate 1-1

[0051] In a flask, add 3-amino-9-methylcarbazole (10g, 51mmol), 3,5-dimethylbenzaldehyde (5.4g, 51mmol), trimethylsilylacetylene (5g, 51mmol), trifluoro Lanthanum methanesulfonate (1g), cuprous iodide (1g) and 30mL of 1-butyl-3-methylimidazolium tetrafluoroborate were reacted at 100°C for 5 hours, water was added, and extracted with dichloromethane , dried, concentrated, and the crude product was purified by column chromatography to obtain 11.5 g with a yield of 75%.

[0052] The synthetic method of intermediate 1-2

[0053] Add intermediate 1-1 (1.5g, 4.9mmol), iridium trichloride trihydrate (0.60g, 2mmol), water (5mL), ethoxyethanol (15mL) in a one-necked flask, and heat to reflux under nitrogen protection 24 hours. After the reaction was completed, it was cooled to room temperature, the solid was filtered out with suction, and the filter cake was washed with ethanol to o...

Embodiment 2

[0057] Synthetic route of compound 28

[0058]

[0059] The synthetic method of intermediate 28-1

[0060] Add 5-chloro-2-(3,5-dimethylphenyl) quinoline (5.34g, 20mmol), o-nitrophenylboronic acid (4.01g, 24mmol), potassium carbonate (6.90g, 50mmol) ), palladium acetate (0.11g, 0.5mmol), 2-dicyclohexylphosphonium-2,4,6-triisopropylbiphenyl (0.36g, 0.75mmol), dioxane (75mL) and water (25mL ), heated to reflux under nitrogen protection for 8 hours. Cool to room temperature, remove dioxane by rotary evaporation, extract the organic phase with dichloromethane, combine the organic phases, and dry with anhydrous sodium sulfate. The crude product was separated by column chromatography to obtain 3.15 g of a yellow solid with a yield of 43.7%.

[0061] The synthetic method of intermediate 28-2

[0062] Add intermediate 28-1 (2.12g, 6mmol), triphenylphosphine (4.72g, 18mmol), o-dichlorobenzene (25mL) into a single-necked flask, heat and reflux under nitrogen protection for 5 hours...

Embodiment 3

[0070] Synthetic route of compound 40

[0071]

[0072] The synthetic method of intermediate 40-1

[0073] In a flask, add 3-amino-9-ethylcarbazole (6g, 28.6mmol), 3,5-dimethylbenzaldehyde (3.8g, 28.6mmol), phenylacetylene (3g, 28.6mmol), trifluoro Lanthanum methanesulfonate (0.5g), cuprous iodide (0.5g) and 30mL of 1-butyl-3-methylimidazolium tetrafluoroborate were reacted at 100°C for 5 hours, water was added, and dichloro Extracted with methane, dried and concentrated, the crude product was purified by column chromatography to obtain 10 g with a yield of 84%.

[0074] The synthetic method of intermediate 40-2

[0075] The synthesis method is the same as that of intermediate 28-4, and the raw material used is intermediate 40-1.

[0076] The synthetic method of compound 40

[0077] The synthesis method was the same as that of compound 28, and the yield was 16%.

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Abstract

The invention provides an iridium complex with the structural formula shown in the specification. The iridium complex has better heat stability, high luminous efficiency and high luminous purity and can be applied to the fields of OLEDs (organic light-emitting devices), organic solar cells, organic film transistors or organic photoreceptors. The invention also provides an OLED. The device comprises an anode, a cathode and an organic layer, wherein the organic layer comprises at least one of a light-emitting layer, a hole injection layer, a hole transfer layer, a hole barrier layer, an electroninjection layer and an electron transfer layer, at least one layer in the organic layer contains a compound shown in structural formula I. The OLED produced from the iridium complex has the advantages of good electroluminescence efficiency, excellent color purity and long service life.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an iridium complex and its application, and also relates to an organic electroluminescent device. Background technique [0002] Organic electroluminescent devices (OLEDs) are devices prepared by depositing a layer of organic materials between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device includes a hole transport layer, emissive layer and electron transport layer. The holes generated by the anode are combined with the electrons generated by the cathode through the hole transport layer to form excitons in the light emitting layer through the hole transport layer, and then emit light. Organic electroluminescent devices can be adjusted to emit various required lights by changing the material of the light-emitting layer as required. [0003] As a new type of display technology, organic electrol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/18H10K50/15H10K50/16H10K50/17H10K50/11H10K2102/00H10K2102/301Y02E10/549
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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