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Tertiary butyl-containing spirobifluorene compound and preparation and application thereof

A spirobifluorene and tert-butyl technology, applied in the field of organic electroluminescent materials, can solve the problems of small adjustability, difficulty in obtaining blue light, and low energy efficiency

Inactive Publication Date: 2016-12-14
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the research and application of inorganic electroluminescent materials have been carried out for a long time, there have always been some difficult problems in inorganic electroluminescent materials, such as: few types of materials, small adjustability, low energy efficiency, and the use of Harsh conditions, difficult to obtain Blu-ray, etc.

Method used

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  • Tertiary butyl-containing spirobifluorene compound and preparation and application thereof
  • Tertiary butyl-containing spirobifluorene compound and preparation and application thereof
  • Tertiary butyl-containing spirobifluorene compound and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] (1) Preparation of tert-butyl chloride

[0109]

[0110] Add 32mL of tert-butanol to a 500mL single-necked round-bottom flask, measure 82mL of concentrated hydrochloric acid with a graduated cylinder, and add it to the reaction flask several times. Vigorously oscillate after adding each time. During the oscillating process, attention should be paid to release the gas generated by the reaction. Oscillate until no gas is produced (the whole process lasts about 10 minutes). Transfer the obtained liquid into a separatory funnel and let it stand for a period of time. After the layers were separated, the lower aqueous layer was removed, and then the organic layer obtained by liquid separation was washed with 30 mL each of water, saturated sodium bicarbonate solution and water respectively, and the organic layer was collected, dried by adding a small amount of anhydrous calcium chloride, and stored for future use;

[0111] (2) Preparation of 4,4'-di-tert-butylbiphenyl

[0...

Embodiment 2

[0139] Preparation of 2-tert-butyl-2',7-bis(carbazolyl)-9,9'-spirobifluorene (SPF-BCZ)

[0140] (1) 2-tert-butyl-2', 7-bromo-9, the preparation method of 9'-spirobifluorene is the same as in Example 1.

[0141] (2) Preparation of 2-tert-butyl-2',7-bis(carbazolyl)-9,9'-spirobifluorene

[0142]

[0143] In a 10mL single-necked round bottom flask, add 250mg (0.47mmol) B, 250mg carbazole, 166.7mg copper powder, 50mg18-crown-6 ether, 625mg potassium carbonate, vacuumize, fill with nitrogen protection, add 2.5mL o-dichlorobenzene , heated to reflux at 180°C, stirring continuously, stopped after 72h, filtered with suction, washed the filter cake with ethyl acetate, and removed the solvent in the filtrate by rotary evaporation. The crude product was separated and purified by column chromatography to obtain a yellow solid. Yield: 60.8%. Mp: >280°C. Detection shows that 2-tert-butyl-2' prepared by the present invention, 7-bis(carbazolyl)-9,9'-spirobifluorene 1 H NMR, 13 The C NM...

Embodiment 3

[0146] Example 3: Preparation of 2-tert-butyl-2', 7-bis((two-p-methoxyphenyl)amino)-9,9'-spirobifluorene (SPF-BMO)

[0147] (1) 2-tert-butyl-2', the preparation method of 7-diamino-9,9'-spirobifluorene is the same as in Example 1.

[0148] (2) Preparation of 2-tert-butyl-2',7-bis((di-p-methoxyphenyl)amino)-9,9'-spirobifluorene

[0149]

[0150] In a 10mL single-necked round bottom flask, add 200mg (0.50mmol) A, 507mg 4-iodoanisole, 38.4mg cuprous iodide, 41.2mg o-phenanthroline, 504mg potassium hydroxide, vacuumize and fill with nitrogen gas protection. Add 2.5mL xylene, heat to 140°C, stir and reflux, stop after 72h, filter with suction, wash the filter cake with ethyl acetate, remove the solvent in the filtrate by rotary evaporation, and separate the crude product by column chromatography to obtain an off-white solid. Yield: 82.4%. Mp: 137-139°C. Detection shows that the 2-tert-butyl-2' prepared by the present invention, 7-two ((two p-methoxy)amino)-9,9'-spirobifluoren...

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Abstract

The invention relates to a tertiary butyl-containing spirobifluorene compound and preparation and application thereof. The material has the following general formula (I) shown in the description, wherein R is a structure shown in the description; -Ar shown in the description, wherein -Ar is selected from at least one of the following structural units or derivatives of the following structural units: shown in the description; in the above mentioned structural formulas, m and n are integers of 0 to 8, and R1, R2, R3 and R4 are hydrogen, or straight chains or branched chains or ring alkyl or oxyalkyl chains with 1 to 22 carbon atoms, and can be the same or different. Compared with the prior art, the tertiary butyl-containing spirobifluorene compound disclosed by the invention has the advantages that 4,4'-ditert-butyl-2-brominated biphenyl with low cost replaces 2-brominated biphenyl which is generally used in the conventional 9,9'-spirobifluorene preparation process and is high in cost, and the synthesis method has the characteristics of low cost, simple synthesis route, high yield, easiness in industrial production and the like; a spirobifluorene hole-transmission / electroluminescent material is high in hole-transmission performance and electroluminescent performance.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a tert-butyl-containing spirobifluorene compound and its preparation. Background technique [0002] Electroluminescence (EL) refers to a physical phenomenon in which light-emitting materials directly convert electrical energy into light energy through electronic transitions under the action of an electric field. Although the research and application of inorganic electroluminescent materials have been carried out for a long time, there have always been some difficult problems in inorganic electroluminescent materials, such as: few types of materials, small adjustability, low energy efficiency, and the use of The conditions are harsh, and it is difficult to obtain Blu-ray, etc. Therefore, it is extremely important to explore new luminescent materials. [0003] As a hotspot of international research in recent years, organic electroluminescent materials (OLEDs) a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54C07C217/92C07D209/86C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C211/54C07C217/92C07D209/86C09K2211/1014C09K2211/1007C09K2211/1011C09K2211/1029H10K85/624H10K85/633H10K85/631H10K85/6572H10K50/11
Inventor 肖海波丁宁韩中英檀晶晶张武李少志黄丹宇万建勇
Owner SHANGHAI NORMAL UNIVERSITY
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