苯并环丁烯封端的液晶聚酯酰亚胺的制备与性能

吴文虎; 李洋; 余华光; 刘继延; 黄祚刚; 刘学清

doi:10.11777/j.issn1000-3304.2024.24030

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苯并环丁烯封端的液晶聚酯酰亚胺的制备与性能

研究论文 | 更新时间：2024-11-26

- 苯并环丁烯封端的液晶聚酯酰亚胺的制备与性能
- Preparation and Properties of Liquid Crystal Polyesterimides Terminated with Benzocyclobutene
- 高分子学报 2024年55卷第9期页码：1241-1250
- 作者机构：
  
  江汉大学光电材料与技术学院光电化学材料与器件教育部重点实验室武汉 430056
- 作者简介：
  
  E-mail: hzg19@jhun.edu.cn
  xqliu@jhun.edu.cn
- 基金信息：
  
  国家重点研发计划(2022YFB3603702);江汉大学一流学科建设重大专项(2023XKZ004)
- DOI：10.11777/j.issn1000-3304.2024.24030
  中图分类号：
- 纸质出版日期：2024-09-20，
  
  网络出版日期：2024-05-29，
  
  收稿日期：2024-01-23，
  
  录用日期：2024-03-17
- 稿件说明：
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吴文虎, 李洋, 余华光, 刘继延, 黄祚刚, 刘学清. 苯并环丁烯封端的液晶聚酯酰亚胺的制备与性能. 高分子学报, 2024, 55(9), 1241-1250

Wu, W. H.; Li, Y.; Yu, H. G.; Liu, J. Y.; Huang, Z. G.; Liu, X. Q. Preparation and properties of liquid crystal polyesterimides terminated with benzocyclobutene. Acta Polymerica Sinica, 2024, 55(9), 1241-1250
吴文虎, 李洋, 余华光, 刘继延, 黄祚刚, 刘学清. 苯并环丁烯封端的液晶聚酯酰亚胺的制备与性能. 高分子学报, 2024, 55(9), 1241-1250 DOI： 10.11777/j.issn1000-3304.2024.24030.

Wu, W. H.; Li, Y.; Yu, H. G.; Liu, J. Y.; Huang, Z. G.; Liu, X. Q. Preparation and properties of liquid crystal polyesterimides terminated with benzocyclobutene. Acta Polymerica Sinica, 2024, 55(9), 1241-1250 DOI： 10.11777/j.issn1000-3304.2024.24030.

摘要

设计并合成了具有苯并环丁烯(BCB)结构的含酚羟基的酰亚胺2-(二环[4.2.0

]

辛-1

5-三烯-3-基)-5-羟基-1

-异吲哚-1

3(2H)-二酮(BCB-HP)和含芳酸的酰亚胺2

3-二氢-1

3-二氧-2-(二环[4.2.0

]

辛-1

5-三烯-3-基)-1

-异吲哚-5-羧酸(BCB-CP)，与4-羟基苯甲酸(4-HBA)、6-羟基-2-萘甲酸(HNA)和

-(3-羧基苯基)-4-羟基邻苯二甲酰亚胺(3-CHP)通过溶液缩聚共聚合成了液晶聚酯酰亚胺(LCPEI). 与不含热活性BCB基团的LCPEI比较，BCB型LCPEI具有更好的溶解度、较低的熔融温度(

=200 ℃，以及较高的玻璃化转变温度(

=149 ℃)，具有良好的加工和应用潜力. LCPEI-22-BCB (含22 mol% CHP)制备的薄膜相较于LCPEI-22，弹性模量更高，介电常数相近(

=3.364 @10 GHz)，介电损耗更低(

=0.0019)，具有作为挠性覆铜板材料的应用前景.

Abstract

Combining features of liquid crystal polyester (LCP) and benzocyclobutene (BCB)

two BCB-containing compounds

2-(dicyclo[4.2.0

]

oct-1

5-triene-3-yl)-5-hydroxy-1

-isoindole-1

3(2H)-diketone (BCB-HP) and 2

3-dihydro-1

3-dioxo-2-(dicyclo[4.2.0

]

oct-1

5-triene-3-yl)-1

-isoindole-5-carboxylic acid (BCB-CP)

were designed and prepared as terminal capping compounds for LCP synthesis. Liquid crystal polyesterimides (LCPEIs) were synthesized by solution condensation copolymerization of the phenolic BCB-HP

the carboxylic BCB-CP

4-hydroxybenzoic acid (4-HBA)

and 6-hydroxy‍-2-naphthoic acid (HNA)

along with

-‍(3-carboxyphenyl)‍-4-hydroxyphthalimide (3-CHP)

in the presence of esterification reagents and conditions

diphenyl chlorophosphate (DPCP)

LiCl and pyridine at room to reflux temperature

and subsequent methanol precipitation and drying as fine powder. Films of LCPEI-22/44-BCB (with 22 mol%/44 mol% 3-CHP) were generated by hot-pressing and curing procedures

and the curing temperature is around 270 ℃

which is favorably lower than those of 3-ethynylaniline (3-EA

310 ℃) and 4-phenylethynylphthalic anhydride (PEPA

370 ℃)

two alkyne-type thermal reactive terminal groups used in literature. These BCB-type LCPEIs have good thermal stabilities (

= 416.7-454.8 ℃) in thermo-gravimetric analysis (TGA) under nitrogen gas. Compared with the commercially available Vect

ra A950 LCP and non-BCB-containing LCPEI-22/44

LCPEI-22/44-BCB have better solubility (4/1

chloroform-pentafluorophenol)

lower melting temperature (

200 ℃)

higher glass transition temperature (

= 149-167 ℃)

and lower isotropic temperature (

350 ℃)

indicating processing convenience and application potential. Compared to LCPEI-22

film of LCPEI-22-BCB has a favorably lower linear thermal expansion coefficient (CTE

41.13 versus 73.29×10

-6

-1

)

a higher storage modulus (

3.48 versus 0.53 GPa)

higher elastic modulus (

10.83 versus 9.40 GPa)

and higher hardness (

0.66 versus 0.58 GPa). Film of LCPEI-22-BCB also has better hydrophobicity with increased water contact angle (124.7° versus 114.3°). Film of LCPEI-22-BCB exhibits good and comparable low dielectric constant (

=3.364) and excellent low dielectric loss (

=0.0019) at 10 GHz high frequency and room temperature. Merits of the above features would make the BCB-type LCPEIs promising materials for flexible copper clad laminates.

关键词

液晶聚酯聚酯酰亚胺苯并环丁烯低介电常数

Keywords

Liquid crystal polyesterPolyesterimideBenzocyclobuteneLow dielectric constant

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