Synthesis and properties of high heat-resistant transparent polyimides containing terphenyl skeleton

IF 5.8 2区化学 Q1 POLYMER SCIENCE

European Polymer Journal Pub Date : 2025-03-31 DOI:10.1016/j.eurpolymj.2025.113924

Jinglei Xing , Lei Yang , Tianci Ma , Xingzhong Fang , Guofei Chen

{"title":"Synthesis and properties of high heat-resistant transparent polyimides containing terphenyl skeleton","authors":"Jinglei Xing , Lei Yang , Tianci Ma , Xingzhong Fang , Guofei Chen","doi":"10.1016/j.eurpolymj.2025.113924","DOIUrl":null,"url":null,"abstract":"<div><div>Colorless polyimide (CPI) films have good application prospects in flexible optoelectronic devices due to their excellent heat resistance and transparency. In this study, a diamine monomer containing a terphenyl skeleton and CF<sub>3</sub> group substituted at <em>ortho</em>-position of amino group, 1,4-bis(3-(trifluoromethyl)-4-aminophenyl)benzene (6FTD), was successfully designed and synthesized, and a series of corresponding polyimides (PIs) were obtained by copolymerization of 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA), 6FTD and 2,2′-bis(trifluoromethyl)benzidine (TFDB). The introduction of rigid and linear terphenyl structure in 6FTD was beneficial to improve the heat resistance and mechanical properties of PI films. In addition, the CF<sub>3</sub> group derived from 6FTD effectively inhibited the rotation between the imide ring and the benzene, so that the 6FTD-containing PI film had a high glass transition temperature (<em>T</em><sub>g</sub>). At the same time, the CF<sub>3</sub> groups caused a large free volume between molecular chains, which ensured the excellent optical transparency and solubility. In particular, PI-50 exhibited high <em>T</em><sub>g</sub> of 399 °C, transmittance of 82% at 450 nm, tensile strength of 146 MPa and tensile modulus of 3.9 GPa. These results indicate that the design of rigid skeleton and side group provides an effective method for developing heat-resistant transparent PI.</div></div>","PeriodicalId":315,"journal":{"name":"European Polymer Journal","volume":"231 ","pages":"Article 113924"},"PeriodicalIF":5.8000,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Polymer Journal","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0014305725002125","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"POLYMER SCIENCE","Score":null,"Total":0}

引用次数: 0

Abstract

Colorless polyimide (CPI) films have good application prospects in flexible optoelectronic devices due to their excellent heat resistance and transparency. In this study, a diamine monomer containing a terphenyl skeleton and CF₃ group substituted at ortho-position of amino group, 1,4-bis(3-(trifluoromethyl)-4-aminophenyl)benzene (6FTD), was successfully designed and synthesized, and a series of corresponding polyimides (PIs) were obtained by copolymerization of 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA), 6FTD and 2,2′-bis(trifluoromethyl)benzidine (TFDB). The introduction of rigid and linear terphenyl structure in 6FTD was beneficial to improve the heat resistance and mechanical properties of PI films. In addition, the CF₃ group derived from 6FTD effectively inhibited the rotation between the imide ring and the benzene, so that the 6FTD-containing PI film had a high glass transition temperature (T_g). At the same time, the CF₃ groups caused a large free volume between molecular chains, which ensured the excellent optical transparency and solubility. In particular, PI-50 exhibited high T_g of 399 °C, transmittance of 82% at 450 nm, tensile strength of 146 MPa and tensile modulus of 3.9 GPa. These results indicate that the design of rigid skeleton and side group provides an effective method for developing heat-resistant transparent PI.

Abstract Image

查看原文本刊更多论文

含terphenyl骨架的高耐热透明聚酰亚胺的合成及性能

无色聚酰亚胺（CPI）薄膜具有优良的耐热性和透明性，在柔性光电器件中具有良好的应用前景。本研究成功地设计并合成了一种含有三苯基骨架和邻位取代的CF3基团的二胺单体1,4-二（3-（三氟甲基）-4-氨基苯基）苯（6FTD），并通过4,4 ' -（六氟异丙基）二苯酐（6FDA）、6FTD和2,2 ' -二（三氟甲基）联苯胺（TFDB）的共聚得到了一系列相应的聚酰亚胺（pi）。在6FTD中引入刚性和线性三苯基结构有利于提高PI薄膜的耐热性和力学性能。此外，由6FTD衍生的CF3基团有效地抑制了亚胺环与苯之间的旋转，使得含6FTD的PI膜具有较高的玻璃化转变温度（Tg）。同时，CF3基团在分子链之间形成了较大的自由体积，保证了优异的光学透明性和溶解性。其中，PI-50的Tg高达399℃，在450 nm处透光率高达82%，抗拉强度为146 MPa，抗拉模量为3.9 GPa。这些结果表明，刚性骨架和侧组的设计为开发耐热透明PI提供了一种有效的方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

European Polymer Journal 化学-高分子科学

CiteScore

9.90

自引率

10.00%

发文量

691

审稿时长

23 days

期刊介绍： European Polymer Journal is dedicated to publishing work on fundamental and applied polymer chemistry and macromolecular materials. The journal covers all aspects of polymer synthesis, including polymerization mechanisms and chemical functional transformations, with a focus on novel polymers and the relationships between molecular structure and polymer properties. In addition, we welcome submissions on bio-based or renewable polymers, stimuli-responsive systems and polymer bio-hybrids. European Polymer Journal also publishes research on the biomedical application of polymers, including drug delivery and regenerative medicine. The main scope is covered but not limited to the following core research areas: Polymer synthesis and functionalization • Novel synthetic routes for polymerization, functional modification, controlled/living polymerization and precision polymers. Stimuli-responsive polymers • Including shape memory and self-healing polymers. Supramolecular polymers and self-assembly • Molecular recognition and higher order polymer structures. Renewable and sustainable polymers • Bio-based, biodegradable and anti-microbial polymers and polymeric bio-nanocomposites. Polymers at interfaces and surfaces • Chemistry and engineering of surfaces with biological relevance, including patterning, antifouling polymers and polymers for membrane applications. Biomedical applications and nanomedicine • Polymers for regenerative medicine, drug delivery molecular release and gene therapy The scope of European Polymer Journal no longer includes Polymer Physics.