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Bipolar phosphorescent iridium complex based on fluorenyl-oxadiazole, and preparation method and applications thereof

A technology of phosphorescent iridium complexes and oxadiazoles, which is applied in the field of organic phosphorescent materials, can solve the problems of oxadiazoles that are rarely reported, and achieve the effects of simple preparation, improved luminous efficiency, and improved efficiency

Inactive Publication Date: 2019-01-11
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, oxadiazoles are used as electron acceptors and electron transfer units with strong electron affinity in electroluminescent materials in relevant literature reports, but oxadiazoles with bipolar phosphorescent OLEDs are rarely reported

Method used

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  • Bipolar phosphorescent iridium complex based on fluorenyl-oxadiazole, and preparation method and applications thereof
  • Bipolar phosphorescent iridium complex based on fluorenyl-oxadiazole, and preparation method and applications thereof
  • Bipolar phosphorescent iridium complex based on fluorenyl-oxadiazole, and preparation method and applications thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0045] (1) Synthesis and characterization of 2-bromo-7-iodo-9,9-dihexylfluorene.

[0046] Weigh 2-bromo-7-iodo-fluorene (25.641g, 68.01mmol), a mixture of bromo-n-hexane (33.664g, 204.02mmol) and sodium hydroxide (11.002g, 275.1mmol) was dissolved in DMSO, at 55 After reacting at constant temperature for 10 hours at ℃, the DMSO solvent was removed by repeated extraction with water and ethyl acetate, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, and use petroleum ether as an eluent for column chromatography to obtain a white product; dry, weigh, and calculate to obtain a product yield of 90%.

[0047]

[0048] (2) Synthesis and characterization of 2-N,N-diphenyl-7-bromo-9,9-dihexyl-fluorene.

[0049] Weigh 2-bromo-7-iodo-9,9-dihexylfluorene (7.64g, 14.12mmol), diphenylamine (2.213g, 12.82mmol), CuI (0.139g, 0.715) and potassium tert-butoxide (t -BuOK) (4.853g, 42.38mmol) was put into a three-necked flask, and after the nitrogen was replaced three times, 1...

Embodiment 2

[0069] (1) Synthesis of 2-bromo-7-iodo-9,9-dihexylfluorene.

[0070] Weigh 2-bromo-7-iodo-fluorene (25.641g, 68.01mmol), a mixture of bromo-n-hexane (33.664g, 204.02mmol) and sodium hydroxide (11.002g, 275.1mmol) was dissolved in DMSO, at 55 After reacting at constant temperature for 10 hours, extract with water and ethyl acetate to remove the DMSO solvent, dry the organic phase with anhydrous Na2SO4, and use petroleum ether as the eluent for column chromatography to obtain a white product; dry and weigh , The calculated product yield is 90%.

[0071] (2) Synthesis of 2-N,N-diphenyl-7-bromo-9,9-dihexyl-fluorene.

[0072] Weighed 2-bromo-7-iodo-9,9-dihexylfluorene (7.64g, 14.12mmol), diphenylamine (2.213g, 12.82mmol), CuI (0.139g, 0.715) and t-BuOK (4.853g , 42.38mmol) into a three-necked flask, and after replacing nitrogen three times, 15ml of toluene was added to these mixtures as a reaction solvent, and reacted at 110° C. for 8 hours. The reaction was extracted with dichl...

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Abstract

The invention discloses a bipolar phosphorescent iridium complex based on fluorenyl-oxadiazole, and a preparation method and applications thereof. According to the preparation method, a bipolar main body based on fluorenyl-oxadiazole is taken as a base, group A is introduced onto the fluorenyl, group R2 is introduced onto oxadiazole; the bipolar phosphorescent iridium complex based on fluorenyl-oxadiazole is composed of a B type compound and a FB type compound, and the structures are disclosed in the invention, wherein the group A is a diphenylamine group, the group R1 is an alkyl chain, and the group R2 is an electron withdrawing group. The bipolar phosphorescent iridium complex can be taken as an OLED device auxiliary doping material, and prepared devices are excellent in performance; the synthesis patch is simple; material cost is low; and it is beneficial for development of iridium complex phosphorescent materials.

Description

technical field [0001] The invention relates to a bipolar phosphorescent iridium complex based on fluorenyl-oxadiazole and its preparation method and application, belonging to the technical field of organic phosphorescent materials. Background technique [0002] Due to its own advantages, phosphorescent iridium complexes have attracted widespread attention from researchers and businesses. With the development of science and technology, the research and development of new host materials is becoming more and more important. Both hole transport materials and electron transport materials are required in the luminescent process. Hole transport materials generally require ligands with good hole transport capabilities. We often use carbazole groups, indole groups, fluorene groups, etc.; electron transport materials usually have good electron transport capabilities, that is, they have electron-withdrawing groups. Commonly used groups include diphenoxyphosphine, oxadiazole, pyridine,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0086C09K2211/185H10K85/342H10K50/11
Inventor 李咏华陆晴琚飞飞刘加伟黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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