Diphenyl ether azole derivative bioelectronic transmission material, and its new preparing method and use

A technology of electron transport materials and azole derivatives, which can be used in light-emitting materials, chemical instruments and methods, organic chemistry, etc., and can solve problems such as shortage of materials that emit blue light.

Inactive Publication Date: 2006-05-24
郭鹏
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Luminescent materials in this band, especially those that emit blue light, are currently in short supply.

Method used

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  • Diphenyl ether azole derivative bioelectronic transmission material, and its new preparing method and use
  • Diphenyl ether azole derivative bioelectronic transmission material, and its new preparing method and use
  • Diphenyl ether azole derivative bioelectronic transmission material, and its new preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] In a three-necked flask equipped with a stirrer, a nitrogen inlet tube, and a reflux condenser, add o-aminophenol (24mmol) and anhydrous tetrahydrofuran (THF) (30ml) in sequence, stir, and add 4,4'-oxygen in 50 minutes. Heterodibenzoyl chloride (10mmol), reacted at room temperature for 4 hours, then poured the reaction solution into 150ml deionized water, a white solid was precipitated, filtered, dried, and washed with THF / H 2 O was recrystallized to give white crystals 4,4″-oxabis[2′-hydroxy-benzoanilide]. Put 4,4″-oxabis[2′-hydroxy-benzoanilide] into the quartz tube , evacuated to 1 mmHg, heated to 250-270 ° C for 4 hours, cooled, and recrystallized with toluene to obtain 2,2'-(oxabi-p-phenylene)bisbenzoxazole, the compound ( A), the yield is 85%, and the melting point is 246-247°C.

Embodiment 2

[0106] In a three-necked flask equipped with a stirrer, a nitrogen inlet tube, and a reflux condenser, add o-aminothiophenol (22mmol), 1,4-dioxane (30ml) successively, stir, and add 4 in 30 minutes, 4'-Oxadibenzoyl chloride (10mmol), reacted at room temperature for 8 hours, then poured the reaction solution into 250ml deionized water, a white solid was precipitated, filtered, dried, and washed with 1,4-dioxane / h 2 O recrystallized to obtain white crystal 4,4″-oxabis[2′-mercapto-benzoanilide]. Put 4,4″-oxabis[2′-mercapto-benzoanilide] into the quartz tube , vacuumize to 1mmHg, heat to 260-280°C for 8 hours, cool, and recrystallize with xylene to obtain 2,2'-(oxabi-p-phenylene)bisbenzothiazole, the compound ( B), yield 80%, melting point>280°C.

Embodiment 3

[0108] In a three-necked flask equipped with a stirrer, a nitrogen inlet tube, and a reflux condenser, N-phenyl-1,2-phenylenediamine (20mmol), N,N-dimethylformamide (DMF) (30ml ), stirred, and added 4,4'-oxadibenzoyl chloride (10mmol) in 15 minutes, reacted for 1 hour at room temperature, then poured the reaction solution into 200ml deionized water, white solids were precipitated, filtered, and dried , with DMF / H 2 O was recrystallized to give 4,4'-oxabis[N-[2-(anilino)phenyl]benzamide as white crystals. Put 4,4'-oxabis[N-[2-(anilino)phenyl]benzamide into a quartz tube, evacuate to 1mmHg, heat to 280-300°C for 6 hours, cool, use for solid Sublimation purification yielded 2,2'-(oxabi-p-phenylene)bis(3-phenylbenzimidazole), compound (L), with a yield of 75% and a melting point of 237-239°C.

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Abstract

The invention belongs to the technical field of organic luminous material, concretely relating to a diphenyl ether azole ramification electronic transmission material and its new preparing method and application. It uses diphenyl ester as the center in structure, containing nitrogen, sulfur and oxygen heteroaromatic cycles; and it is made by acylation and condensation reactions of aromatic amine; and it has very good thermal stability and film forming property, widely used as electronic transmission material for organic light emitting devices and doping material.

Description

technical field [0001] The invention belongs to the field of organic light-emitting materials, and in particular relates to a diphenyl ether-type azole derivative electron transport material and a new preparation method and application thereof. Background technique [0002] Since Tang et al. (Tang C.W., Vanslyke S A.Appl Phys Lett, 1987, 51 (12), 913.) reported low driving voltage, high brightness, high luminous efficiency organic small molecule thin film electroluminescent device and Burroughes etc. ( Since Burroughes J.H., Bradlyd O.C., Brown A.R., et al. Nature, 1990, 347, 539.) reported the first polymer electroluminescent device, research on organic / polymer electroluminescent devices has made great progress. Among them, efficient carrier transport materials play an important role. In particular, the development of efficient electron-transporting materials is considered to be the key to further improving the performance of organic electroluminescent devices. Because, c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D403/12C07D417/12C09K11/06
Inventor 吕银祥郭鹏
Owner 郭鹏
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