Bisphosphonic heterocyclic organic electroluminescent compounds comprising spirofluorene structures, and synthetic method and application thereof

A spirofluorene structure and compound technology, which is 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: 2016-02-24
HENAN ACADEMY OF SCI CHEM RES INST CO LTD +1
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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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  • Bisphosphonic heterocyclic organic electroluminescent compounds comprising spirofluorene structures, and synthetic method and application thereof
  • Bisphosphonic heterocyclic organic electroluminescent compounds comprising spirofluorene structures, and synthetic method and application thereof
  • Bisphosphonic heterocyclic organic electroluminescent compounds comprising spirofluorene structures, and synthetic method and application thereof

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Embodiment 1

[0028] The synthesis of embodiment 1 compound Ia

[0029]

[0030] Synthesis of compound Ⅳ

[0031] 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 10h. 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%.

[0032] Synthesis of Compound V

[0033] 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 dropwise a...

Embodiment 2

[0042] The synthesis of embodiment 2 compound 1b

[0043]

[0044] Synthesis of compound Ⅵb

[0045] 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 yielded 2.0 g of a light yellow solid, with a yield of 78%.

[0046] Synthesis of Compound Ⅶb

[0047] 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) again to dissolve, dry over anhydrous magnesium sulfate, filter with suction, and spin dry; Silica gel column c...

Embodiment 3

[0052] The synthesis of embodiment 3 compound Ic

[0053]

[0054] Synthesis of Compound Ⅵc

[0055] 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 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%.

[0056] Synthesis of Compound Ⅶc

[0057] 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) again to dissolve, dry over anhydrous magnesium sulfate, filter with suction, and spin dry; Silica gel colu...

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Abstract

The invention discloses bisphosphonic heterocyclic organic electroluminescent compounds comprising spirofluorene structures, and a synthetic method and application thereof, and belongs to the field of organic electroluminescent materials. A general structural formula of the bisphosphonic heterocyclic organic electroluminescent compounds is as shown in the description, wherein X represents O, S or Se, and R is shown in the description. The organic electroluminescent compounds provided by the invention can be applied to luminescent layers of organic electroluminescent devices; luminescent properties of corresponding devices can be regulated by simple chemical modification of phosphine atoms; the organic electroluminescent compounds are excellent in thermal stability; through the spirofluorene structures, the packing effect among molecules can be effectively reduced, so that the efficiency of the corresponding organic electroluminescent devices can be significantly improved, and the service lives of the corresponding organic electroluminescent devices can be significantly prolonged.

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 a bisphosphine heterocyclic organic electroluminescent compound containing a spirofluorene structure, 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 mob...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6568C09K11/06H01L51/54
CPCC09K11/06C07F9/65685C09K2211/1007C09K2211/1096H10K85/657
Inventor 陈辉杨瑞娜杨振强段征张银龙孙敏青
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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