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Preparation and Properties of Liquid Crystal Polyesterimides Terminated with Benzocyclobutene
- Acta Polymerica Sinica Pages: 1-10(2024)
- 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：
Zuo-gang Huang, E-mail: zghuang@pku.org.cn
Xue-qing Liu, E-mail: xqliu@ihun.edu.cn
- 基金信息：
DOI：10.11777/j.issn1000-3304.2024.24030
CLC：-
Published Online：24 April 2024，
Received：23 January 2024，
Revised：17 March 2024，
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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, 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, doi: 10.11777/j.issn1000-3304.2024.24030
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, doi: 10.11777/j.issn1000-3304.2024.24030 DOI：
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, doi: 10.11777/j.issn1000-3304.2024.24030 DOI：
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
3
5-三烯-3-基)-5-羟基-1
H
-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
3
5-三烯-3-基)-1
H
-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
N
-(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(
T
m
=200 ℃，以及较高的玻璃化转变温度(
T
g
=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(
D
k
=3.364 @10 GHz)，介电损耗更低(
D
f
=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
3
5-triene-3-yl)-5-hydroxy-1
H
-isoindole-1
3(2H)-diketone (BCB-HP) and 2
3-dihydro-1
3-dioxo-2-(dicyclo[4.2.0]oct-1
3
5-triene-3-yl)-1
H
-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
N
-(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 (
T
d
5%
= 416.7-454.8 ℃) in thermo-gravimetric analysis (TGA) under nitrogen gas. Compared with the commercially available Vectra A950 LCP and non-BCB-containing LCPEI-22/44
LCPEI-22/44-BCB have better solubility (4/1 v/v chloroform-pentafluorophenol)
lower melting temperature (
T
m
200 ℃)
higher glass transition temperature (
T
g
149-167 ℃)
and lower isotropic temperature (
T
i
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
K
-1
)
a higher storage modulus (
E'
3.48 versus 0.53 GPa)
higher elastic modulus (
E
r
10.83 versus 9.40 GPa)
and higher hardness (
H
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 (
D
k
=3.364) and excellent low dielectric loss (
D
f
=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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