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Amine derivative containing spirofluorene group and application of amine derivative in organic electroluminescent device

A technology of amine derivatives and spirofluorenyl, which is applied in the field of organic optoelectronic materials and devices, can solve the problems of low heat resistance, lower driving voltage, unsatisfactory current efficiency, etc., and achieve good hole transport ability, Reduced driving voltage, improved luminous efficiency and heat resistance effects

Active Publication Date: 2020-05-29
JILIN YUANHE ELECTRONICS MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the heat resistance of the device obtained by using this compound as a hole transport layer is not very high.
In addition, the current efficiency of the OLED devices fabricated using the above two compounds as hole transport materials is not satisfactory and the driving voltage needs to be reduced.

Method used

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  • Amine derivative containing spirofluorene group and application of amine derivative in organic electroluminescent device
  • Amine derivative containing spirofluorene group and application of amine derivative in organic electroluminescent device
  • Amine derivative containing spirofluorene group and application of amine derivative in organic electroluminescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The concrete preparation method of intermediate (I) is as follows:

[0064] Under a nitrogen atmosphere, add raw material (a) (15mmol), raw material (b) (15mmol), sodium tert-butoxide (30mmol) into 150mL of anhydrous toluene, add palladium acetate (0.3mmol), tri-tert-butyl Phosphine (0.3 mmol) was reacted at 80°C for 8 hours. After cooling, filter through a diatomaceous earth / silica gel funnel, remove the organic solvent from the filtrate by distillation under reduced pressure, recrystallize the obtained residue in toluene, collect the obtained solid by filtration, and dry to obtain intermediate (I). The structures of the obtained intermediates are shown in Table 1.

[0065] Taking intermediate 1 as an example to illustrate the specific details of the synthesis example: under nitrogen atmosphere, raw material a-1 (3.14g, 15mmol), raw material b-1 (5.91g, 15mmol), sodium tert-butoxide (2.88g, 30mmol ) into 150 mL of anhydrous toluene, palladium acetate (0.07 g, 0.3 mmo...

Embodiment 2

[0072] The concrete preparation method of compound is as follows:

[0073] Under nitrogen atmosphere, put starting material c-A (19.55mmol), intermediate (I) (20.14mmol) and sodium tert-butoxide (27.0mmol) into anhydrous toluene, heat and stir the resulting mixture and then reflux, to which Put [bis(tri-tert-butylphosphine)]palladium (0.39mmol, 0.02eq). After cooling, it was filtered through a celite / silica gel funnel, and the filtrate was distilled under reduced pressure to remove the organic solvent, and then recrystallized to prepare a pure product of the compound. The relevant data of the obtained target compounds are shown in Table 2.

[0074] Taking compound 1 as an example to illustrate the specific details of the synthesis example: under a nitrogen atmosphere, the raw material c-A-1 (8.02g, 19.55mmol), intermediate 1 (10.54g, 20.14mmol) and sodium tert-butoxide (2.6g, 27.0 mmol) was put into anhydrous toluene, the resulting mixture was heated and stirred and then ref...

Embodiment 3

[0079] The concrete preparation method of compound is as follows:

[0080] Under a nitrogen atmosphere, put raw material c-B (20mmol), intermediate (I) (21mmol) and sodium tert-butoxide (27.0mmol) into anhydrous toluene, heat and stir the resulting mixture and then reflux, and put [Bis(tri-tert-butylphosphine)]palladium (0.4mmol, 0.02eq). After cooling, it was filtered through a celite / silica gel funnel, and the filtrate was distilled under reduced pressure to remove the organic solvent, and then recrystallized to prepare a pure product of the compound. The relevant data of the obtained target compounds are shown in Table 3.

[0081] Taking compound 37 as an example to illustrate the specific details of the synthesis example: under nitrogen atmosphere, the raw material c-B-37 (8.2g, 20mmol), intermediate 1 (11.0g, 21mmol) and sodium tert-butoxide (2.6g, 27.0mmol) Putting in anhydrous toluene, the resulting mixture was heated and stirred and then refluxed, and [bis(tri-tert-b...

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Abstract

The invention relates to an amine derivative containing a spirofluorene group and an application thereof in an organic electroluminescent device, and belongs to the technical field of organic photoelectric materials and devices. The molecular structure of the derivative is shown in the specification, and the derivative can be used for preparing a hole transport layer of an organic light-emitting diode (OLED). An organic light-emitting device prepared by adopting the amine derivative as a hole transport material has the advantages of high brightness, high efficiency and good stability, and theperformance of the OLED device is effectively improved.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials and devices, in particular to an amine derivative containing a spirofluorene group and its application in organic electroluminescent devices. Background technique [0002] An organic electroluminescent device (OLED: Organic Light Emitting Device) is a light-emitting diode, in which the light-emitting layer is a film made of an organic compound, and the OLED device can emit light under a certain driving voltage. A light-emitting layer of organic compounds is sandwiched between two electrodes. OLEDs are used in flat panel displays due to their high illumination, low weight, ultra-thin profile, self-illumination without backlight, low power consumption, and fast response. [0003] OLED devices are typically composed of layers of organic materials between two electrodes, including a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL). The ba...

Claims

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Application Information

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IPC IPC(8): C07D311/96C07D405/04C09K11/06H01L51/50H01L51/54
CPCC07D311/96C07D405/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1088H10K85/624H10K85/636H10K85/633H10K85/631H10K85/615H10K85/654H10K85/6574H10K85/6572H10K50/15H10K50/00Y02E10/549
Inventor 张佐伦王悦
Owner JILIN YUANHE ELECTRONICS MATERIALS CO LTD
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