Bis-tri-aromatic amine compound containing spiral structure, application and light emitting diode

A technology of triaryl amines and compounds, applied in the field of organic electroluminescent devices, can solve the problems of high energy consumption in preparation, affect device efficiency, poor thermal stability, etc., and achieve high luminous purity, high luminous efficiency, and good thermal stability. Effect

Inactive Publication Date: 2019-02-12
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional hole injection materials, such as copperphthalocyanine (CuPc), are slow to degrade, consume high energy for preparation, are not conducive to environmental protection, and they absorb light, which affects the efficiency of devices
The original hole transport materials such as NPB have poor thermal stability, which also greatly affects the life of the device.

Method used

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  • Bis-tri-aromatic amine compound containing spiral structure, application and light emitting diode
  • Bis-tri-aromatic amine compound containing spiral structure, application and light emitting diode
  • Bis-tri-aromatic amine compound containing spiral structure, application and light emitting diode

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthetic route of intermediates A, B, C

[0051]

[0052] Synthesis of Intermediate A

[0053] In a three-necked flask, add thiopheneboronic acid (10g, 78mmol), o-bromoiodobenzene (24g, 86mmol), potassium carbonate (27g, 0.2mol), tetrahydrofuran (200mL), water (100mL), tetrakistriphenylphosphine palladium (0.5g), under the protection of nitrogen, heated to reflux for 10 hours, cooled, extracted with dichloromethane, concentrated, the crude product was purified by column chromatography to obtain 14g, yield 75%.

[0054] Synthesis of Intermediate B

[0055] In the three-necked flask, add intermediate A (10g, 42mmol) and dry tetrahydrofuran (100mL) successively, cool to minus 70°C under nitrogen protection, slowly add 2.5M n-butyllithium (16.8mL), and dropwise add the reaction After 1 hour, 60 mL of a solution of 2-bromofluorenone (10.8 g, 42 mmol) in THF was added. After the addition, slowly rise to room temperature, react for 2 hours, add dichloromethane to extrac...

Embodiment 2

[0067] Synthetic route of compound 2

[0068]

[0069] The synthetic method of compound 2

[0070] In a flask, add Intermediate C (2g, 4.1mmol), bis(4-tert-butyl-phenyl)amine (2.9g, 9.2mmol), sodium tert-butoxide (2g, 20mmol), palladium acetate (50mg), X-phos (100 mg) and o-xylene (30 mL) were heated to reflux for 24 hours under the protection of nitrogen, cooled, and the solvent was removed. The crude product was purified by column chromatography to obtain 2.5 g with a yield of 68%.

[0071] The synthesis method of other examples is the same as that of compound 2, all of which are intermediate C and intermediate F as raw materials, and then reacted with other amines, as shown in Table 1 below:

[0072] Table 1

[0073]

[0074]

Embodiment 11-19

[0076] Fabrication of Organic Electroluminescent Devices

[0077] Preparation of OLEDs using the compounds of the Examples

[0078] First, the transparent conductive ITO glass substrate 110 (with the anode 120 on it) (China CSG Group Co., Ltd.) is washed with deionized water, ethanol, acetone and deionized water in sequence, and then treated with oxygen plasma for 30 seconds.

[0079] Then, PEDOT:PSS (polyethylenedioxythiophene-poly(styrene sulfonate)) with a thickness of 45 nm was spin-coated on the ITO as the hole injection layer 130, and dried at 150° C. for 30 minutes.

[0080] Then, the compound of the present invention was vapor-deposited as the hole transport material 140 on the hole injection layer to a thickness of 40 nm.

[0081] Then, a luminescent layer 146 with a thickness of 30nm is vapor-deposited on the electron blocking layer, wherein CBP is the main luminescent material, and the weight ratio is 8% of Ir(ppy) 3 As a phosphorescent doping guest material.

[...

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Abstract

The invention provides a bis-tri-aromatic amine compound containing a spiral structure. The compound has the structural formula as shown in the figure I in the specification. The compound has relatively good heat stability, high light-emitting efficiency and high light-emitting purity and can be applied to the field of organic light emitting diodes, organic solar cells, organic thin film transistors or organic photoreceptors. The invention further provides an organic light emitting diode. The organic light emitting diode comprises an anode, a cathode and an organic layer, the organic layer comprises at least one of a light-emitting layer body, a hole injection layer body, a hole transmission layer body, a hole blocking layer body, an exciton blocking layer body and an electron transmissionlayer, and at least one layer body of the organic layer contains the compound with the structural formula as shown in the figure I in the specification. The organic light emitting diode prepared by adopting the compound has the advantages of being good in light-emitting efficiency, excellent in color purity and long in service life.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a bistriarylamine compound containing a spiro structure and an application thereof, 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/78C07D409/14C07D413/14C07D405/14H01L51/50H01L51/54
CPCC07D333/78C07D405/14C07D409/14C07D413/14H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/15Y02E10/549
Inventor 黄锦海
Owner SHANGHIA TAOE CHEM TECH CO LTD
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