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A kind of compound containing benzocyclobutene structure, its preparation method, application and polyarylene ether polymer material

A polymer material and polyarylene ether technology, which is applied in the field of high-performance polymer synthesis, can solve the problems of low glass transition temperature and high preparation reaction temperature of polymers, and achieves reduced signal transmission loss, low dielectric constant, and low dielectric constant. The effect of electrical losses

Active Publication Date: 2022-07-08
FUDAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation reaction temperature is high, and the glass transition temperature of the obtained polymer is relatively low (139-210°C).

Method used

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  • A kind of compound containing benzocyclobutene structure, its preparation method, application and polyarylene ether polymer material
  • A kind of compound containing benzocyclobutene structure, its preparation method, application and polyarylene ether polymer material
  • A kind of compound containing benzocyclobutene structure, its preparation method, application and polyarylene ether polymer material

Examples

Experimental program
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preparation example Construction

[0049] The preparation method of the compound of the structure shown in the above general formula I, comprises the following steps (1), step (2) and optional step (3):

[0050] Step (1): Use a phenol represented by one of formulas II-1 to II-3 as a raw material (wherein, the phenol raw material represented by II-3 uses High Performance Polymers, 24(5), 425-431; 2012 reference Synthesis), with trimethylchlorosilane, triethylchlorosilane or tert-butyldimethylchlorosilane to protect the phenolic hydroxyl group of the raw material represented by one of formulas II-1 to II-3 to obtain a compound whose phenolic hydroxyl group is protected ;

[0051]

[0052]Step (2): use the compound whose phenolic hydroxyl group is protected and the benzocyclobutene-4-boronic acid ester represented by one of formulas III-1 to III-3 to carry out a Suzuki coupling reaction catalyzed by a palladium catalyst (Suzuki coupling reaction) reaction) to obtain a silyl ether of a benzocyclobutene-containi...

Embodiment 1 2

[0077] Example 1 Protection of diphenols

[0078] 1.1 Use triethylchlorosilane to protect 4-bromoresorcinol: 4-bromoresorcinol (structural formula II-2) (2.21g, 11.7mmol), triethylchlorosilane ((3.77g, 25.1mmol) ), imidazole (1.84g, 27mmol), and 40mL of dry tetrahydrofuran were added to a 100mL single-necked flask, the upper end of the flask was connected to a condenser tube equipped with a nitrogen balloon, and heated to 50 ° C for reaction for 10h. After the reaction was completed, it was cooled to room temperature and filtered, and rinsed with THF, 100 mL of deionized water was added to the filtrate, and extracted with petroleum ether (50 mL × 3 times). The organic phases were combined and dried with anhydrous magnesium sulfate for 6 h. After filtration, the filtrate was concentrated with a rotary evaporator, and the concentrated solution was separated by column chromatography to obtain White solid. The white solid was dried in a vacuum oven at 50° C. for 12 h to obtain 4.3...

Embodiment 2

[0087] Example 2 Benzocyclobutene Functionalization

[0088] 2.1 White powder of 2-(4'-bromophenyl) hydroquinone protected by tert-butyldimethylchlorosilane obtained in Example 1.2 (1.25 g, 2.53 mmol) and benzocyclobutene-4- Pinacol borate (0.64g, 2.8mmol), potassium carbonate (0.70g, 5.06mmol), tetrakis(triphenylphosphine)palladium (0.1g), 16mL of dioxane, 12mL of deionized water were added to the tape. In a 50mL single-neck flask with a stirrer, the flask mouth was connected to a condenser tube with a nitrogen bulb, the reaction system was placed in an oil bath, and replaced with a nitrogen system three times by a water pump, the reaction temperature was 80 °C, and the reaction time was 10h. After the reaction is completed, filter, add 20 mL of distilled water to the filtrate, repeatedly extract 3 times with petroleum ether (50 mL), combine the organic phases, dry the organic phase with anhydrous magnesium sulfate for 6 h, filter, and concentrate the filtrate with a rotary e...

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Abstract

The invention belongs to the technical field of high-performance polymer synthesis, and specifically relates to a class of compounds containing a benzocyclobutene structure, a preparation method thereof, and a post-curing polyarylene ether prepared by using the compound containing a benzocyclobutene structure. polymer material. According to the technical solution of the present invention, a type of post-curing polyarylene ether polymer material with low dielectric constant, low dielectric loss and high glass transition temperature at the same time can be obtained. When this type of material is used as an insulating dielectric layer in the field of 5G communication materials, its higher glass transition temperature improves the processing performance of the material, and a smaller dielectric constant is beneficial to reduce signal delay, and significantly reduce the dielectric The loss is beneficial to reduce the signal transmission loss in the communication technology. At the same time, since this type of post-cured fluorine-containing polyarylene ether material contains a benzocyclobutene structure, a cross-linking reaction can occur under heating conditions, thereby improving the dimensional stability of the material and reducing the thermal expansion coefficient of the material.

Description

technical field [0001] The invention belongs to the technical field of high-performance polymer synthesis, and in particular relates to a class of compounds containing benzocyclobutene structure, a preparation method and application thereof, and a post-curing polyarylene prepared by using the compound containing benzocyclobutene structure. Ether polymer material. Background technique [0002] Polyarylene ether is a kind of excellent high temperature resistant polymer material. It also has the advantages of small dielectric constant, low dielectric loss and low water absorption. It is expected to be used as an insulating medium layer in the field of 5G communication materials. However, the glass transition temperature of this type of material is not high enough to meet the needs of processing; in addition, when it is used as a dielectric layer material, the high dielectric constant and large dielectric loss can cause signal delay and signal delay. transmission loss. Therefo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/055C07C39/17C07F7/18C08G65/40
CPCC07C39/17C07F7/188C07F7/1804C08G65/4006C08G65/4093C07C2602/06Y02P20/55
Inventor 程元荣李君毅王珺
Owner FUDAN UNIV