An anthracene-based bisphosphine heterosix-membered ring organic electroluminescent compound, synthesis method and application thereof

A compound and six-membered ring technology, applied in the field of organic electroluminescent materials, to achieve the effects of good thermal stability, reduced LUMO orbital, and improved electron injection and transport capabilities

Active Publication Date: 2017-03-22
濮阳惠成新材料产业技术研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there have been no relevant research reports on this type of compound

Method used

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  • An anthracene-based bisphosphine heterosix-membered ring organic electroluminescent compound, synthesis method and application thereof
  • An anthracene-based bisphosphine heterosix-membered ring organic electroluminescent compound, synthesis method and application thereof
  • An anthracene-based bisphosphine heterosix-membered ring organic electroluminescent compound, synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of embodiment 1 compound Ia

[0028]

[0029] Synthesis of compound Ⅳ

[0030] Under argon protection, 9-anthraceneboronic acid (2.2g), 2,5-dibromoiodobenzene (3.6g), tetrahydrofuran (30mL), water (30mL), tetrakis(triphenylphosphine) were added successively to the flask Palladium (100mg), potassium carbonate (2.7g), heated under reflux for 10-12 hours. Stop the reaction, extract three times with ethyl acetate, combine the organic phases, and then wash to neutrality; separate the organic phases, add anhydrous magnesium sulfate to dry, suction filter, and spin dry; silica gel column chromatography gives 3.6 g of white solids, the yield 88%.

[0031] Synthesis of compound V

[0032] Under argon protection, compound IV (3.0 g) and tetrahydrofuran (50 mL) were added to the flask, then the system was cooled to -78 ° C, and a 2.5 M n-hexane solution containing n-butyllithium (6 mL) was added dropwise to the system. ), react at -78°C for 1 hour after the dr...

Embodiment 2

[0040] ESI, m / z: [M+H] + calcd for C 44 h 29 NO 2 P 2 , theoretical value: 665.1674; measured value: 665.1678. The synthesis of embodiment 2 compound 1b

[0041]

[0042] Synthesis of compound Ⅵb

[0043] Compound V (3.0 g) obtained according to the synthesis method of Example 1, toluene (20 mL), and 10% palladium carbon (100 mg) were added to the flask, and the reaction was heated under reflux for 10 hours. After returning to room temperature, excess sulfur powder was added to the system, reacted for 5 hours, and spin-dried; silica gel column chromatography gave 2.0 g of a light yellow solid, with a yield of 78%.

[0044]Synthesis of Compound Ⅶb

[0045] Add compound VIb (2.0 g), glacial acetic acid (20 mL), and liquid bromine (2 g) into the flask, and heat to reflux for 5 hours. Stop the reaction, add saturated sodium thiosulfate solution (20 mL), extract three times with ethyl acetate, combine the organic phases, remove the solvent, add ethyl acetate (10 mL) agai...

Embodiment 3

[0049] ESI, m / z: [M+H] + calcd for C 44 h 29 NS 2 P 2 , theoretical value: 697.1217; measured value: 697.1213. The synthesis of embodiment 3 compound Ic

[0050]

[0051] Synthesis of Compound Ⅵc

[0052] Compound V (3.0 g) obtained according to the synthesis method of Example 1, toluene (20 mL), and 10% palladium carbon (100 mg) were added to the flask, and the reaction was heated under reflux for 12 hours. After returning to room temperature, excess selenium powder was added to the system, reacted for 5 hours, and spin-dried; silica gel column chromatography yielded 2.3 g of a light yellow solid, with a yield of 76%.

[0053] Synthesis of Compound Ⅶc

[0054] Add compound VIc (2.0 g), glacial acetic acid (20 mL), and liquid bromine (2 g) into the flask, and heat to reflux for 7 hours. Stop the reaction, add saturated sodium thiosulfate solution (20 mL), extract three times with ethyl acetate, combine the organic phases, remove the solvent, add ethyl acetate (10 mL...

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Abstract

The invention discloses an anthracene-based bisphosphine hetero six-membered ring organic electroluminescent compound, a synthesis method and an application thereof, belonging to the field of organic electroluminescent materials. This type of compound has the general structural formula shown in formula I, I, wherein X is O, S or Se, and R is phenyl or 1-naphthyl. The organic electroluminescent compound of the present invention can be applied to the light-emitting layer of an organic electroluminescent device, and the light-emitting performance of the device can be effectively changed by simple chemical modification of the phosphine atom; this type of compound has good thermal stability and has good charge injection and The transport capability can significantly improve the efficiency and lifetime of the corresponding organic electroluminescent devices.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a phosphine-containing organic electroluminescent compound, in particular to an anthracene-based bisphosphine hetero six-membered ring organic electroluminescent compound, a synthesis method and an application thereof. Background technique [0002] As a new type of display technology, organic electroluminescent devices have self-illumination, wide viewing angles, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, flexible, bendable and The unique advantages of transparent display panels and environmental friendliness can be applied to flat panel displays and new generation lighting, and can also be used as LCD backlight. Since their invention in the late 1980s, organic electroluminescent devices have found industrial applications, such as screens for cameras and mobile pho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6568C09K11/06H01L51/54
CPCC09K11/06C07F9/65685C09K2211/1014C09K2211/1011C09K2211/1007C09K2211/1096H10K85/636H10K85/633H10K85/631H10K85/657
Inventor 陈辉杨瑞娜张银龙杨振强段征周铎
Owner 濮阳惠成新材料产业技术研究院有限公司
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