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Phenanthrene derivatives, applications thereof, and organic electroluminescent device

A derivative and phenanthrene-based technology, applied in the field of organic electroluminescent devices, can solve problems such as low electron mobility, low electron mobility, and affecting device life and efficiency, and achieve high luminous purity, high luminous efficiency, and good heat dissipation. The effect of stability

Inactive Publication Date: 2018-07-20
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.
[0005] In OLED materials, since most organic electroluminescent materials transport holes faster than electrons, it is easy to cause an imbalance in the number of electrons and holes in the light-emitting layer, so that the efficiency of the device is relatively low.
Tris(8-hydroxyquinoline)aluminum (Alq 3 ) has been widely studied since its invention, but as an electron transport material, its electron mobility is still very low, and it will degrade itself. In the device using it as an electron transport layer, there will be a voltage drop , at the same time, due to the lower electron mobility, a large number of holes enter the Alq 3 In the layer, the excess holes radiate energy in a non-luminescent form, and when used as an electron-transporting material, its application is limited due to its green-emitting properties.

Method used

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  • Phenanthrene derivatives, applications thereof, and organic electroluminescent device
  • Phenanthrene derivatives, applications thereof, and organic electroluminescent device
  • Phenanthrene derivatives, applications thereof, and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthetic route of compound 1

[0046]

[0047] The synthetic method of intermediate 1-1

[0048] In a flask, add 9,10-dibromophenanthrene (15g, 45mmol), pinacol 3-pyridine borate (11g, 54mmol), potassium carbonate (7.5g, 54mmol), tetrahydrofuran (150mL), water (100mL) , tetrakistriphenylphosphine palladium (1g), heated to reflux for 12 hours under nitrogen protection, cooled, extracted with dichloromethane, dried, concentrated, the crude product was purified by column chromatography to obtain 8.7g, yield 58%.

[0049] The synthetic method of intermediate 1-2

[0050] In a flask, add Intermediate 1-1 (8 g, 24 mmol), pinacol diboronate (9.1 g, 36 mmol), potassium acetate (3.5 g, 36 mmol), dioxane (120 mL), Pd(dppf) C l2 (0.5g), heated to reflux under nitrogen protection for 12 hours, cooled, removed the solvent, added water, extracted with dichloromethane, dried, concentrated, and the crude product was purified by column chromatography to obtain 5.9g, yield 65%.

...

Embodiment 2

[0054] Synthetic route of compound 5

[0055]

[0056] The synthesis method is the same as that of intermediate 1-1, the raw materials used are intermediate 1-2 and 2-chloro-3,5-bis(4-phenylbenzene)-triazine, and the yield is 52%.

Embodiment 3

[0058] Synthetic route of compound 7

[0059]

[0060] The synthetic method of intermediate 7-1

[0061] The synthesis method is the same as that of intermediate 1-1, the raw materials used are 9,10-dibromophenanthrene and 2-phenyl-5-pinacol borate pyridine, and the yield is 47%.

[0062] The synthetic method of intermediate 7-2

[0063] The synthesis method is the same as that of intermediate 1-2, the raw material used is intermediate 7-1, and the yield is 55%.

[0064] The synthetic method of compound 7

[0065] The synthesis method is the same as that of intermediate 1-1, the raw materials used are intermediate 7-2 and 2-chloro-3,5-diphenyltriazine, and the yield is 46%.

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Abstract

The invention provides phenanthrene derivatives represented by a formula shown in the description. The phenanthrene derivatives have the advantages of good thermal stability, high luminescent efficiency, and high luminescent purity, and can be applied to fields such as organic electroluminescent device, organic solar cell, organic thin film transistor, organic photoreceptor, or the like. The invention also provides an organic electroluminescent device, which comprises an anode, a cathode, and an organic layer. The organic layer comprises at least one of luminescent layer, hole injecting layer,hole transporting layer, hole blocking layer, electron injecting layer, and electron transporting layer and at least comprises a layer containing compounds represented by the structural formula I. The organic electroluminescent device prepared from the phenanthrene derivatives has the advantages of good electroluminescent 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 a phenanthrene derivative 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 e...

Claims

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Application Information

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IPC IPC(8): C07D401/10C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/10C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1059H10K85/626H10K85/654H10K50/14H10K50/16H10K50/15H10K50/11Y02E10/549
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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