Synthesis and Properties of High Performance Functional Polyimides Containing Rigid Nonplanar Conjugated Fluorene Moieties

Yi-Wu Liu; Li-Shuang Tang; Lun-Jun Qu; Si-Wei Liu; Zhen-Guo Chi; Yi Zhang; Jia-Rui Xu

doi:10.1007/s10118-019-2225-0

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Synthesis and Properties of High Performance Functional Polyimides Containing Rigid Nonplanar Conjugated Fluorene Moieties

ARTICLE | Updated：2021-02-18

- Synthesis and Properties of High Performance Functional Polyimides Containing Rigid Nonplanar Conjugated Fluorene Moieties
- Chinese Journal of Polymer Science Vol. 37, Issue 4, Pages: 416-427(2019)
- Affiliations：
  
  a.PCFM Lab, GD HPPC Lab, Guangdong Engineering Technology Research Centre for High-performance Organic and Polymer Photoelectric Functional Films, State Key Laboratory of Optoelectronic Materials and Technologies, School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China
  b.Key Laboratory of Advanced Packaging Materials and Technology of Hunan Province, School of Packaging and Materials Engineering, Hunan University of Technology, Zhuzhou 412007, China
- Author bio：
  
  ceszy@mail.sysu.edu.cn
- Funds：
- DOI：10.1007/s10118-019-2225-0
  CLC：
- Received：18 December 2018，
  
  Revised：2019-1-13，
  
  Accepted：14 January 2019，
  
  Online First：15 February 2019，
  
  Published：2019-04
- Accepted：
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Citation: Liu, Y. W.; Tang, L. S.; Qu, L. J.; Liu, S. W.; Chi, Z. G.; Zhang, Y.; Xu, J. R. Synthesis and properties of high performance functional polyimides containing rigid nonplanar conjugated fluorene moieties. Chinese J. Polym. Sci. 2019, 37, 416–427

Yi-Wu Liu, Li-Shuang Tang, Lun-Jun Qu, et al. Synthesis and Properties of High Performance Functional Polyimides Containing Rigid Nonplanar Conjugated Fluorene Moieties[J]. Chinese Journal of Polymer Science, 2019, 37(4): 416-427.
Citation: Liu, Y. W.; Tang, L. S.; Qu, L. J.; Liu, S. W.; Chi, Z. G.; Zhang, Y.; Xu, J. R. Synthesis and properties of high performance functional polyimides containing rigid nonplanar conjugated fluorene moieties. Chinese J. Polym. Sci. 2019, 37, 416–427 DOI： 10.1007/s10118-019-2225-0.

Yi-Wu Liu, Li-Shuang Tang, Lun-Jun Qu, et al. Synthesis and Properties of High Performance Functional Polyimides Containing Rigid Nonplanar Conjugated Fluorene Moieties[J]. Chinese Journal of Polymer Science, 2019, 37(4): 416-427. DOI： 10.1007/s10118-019-2225-0.

摘要

Abstract

A diamine (WuFDA) containing vertical rigid non-planar conjugated fluorene moiety and low polarizability group (C―F) was designed and synthesized through three steps of reactions (halogenated reaction

Suzuki coupling reaction

and reduction reaction). Four kinds of high performance functional polyimides (WuFPI-6F

WuFPI-BP

WuFPI-BT

and WuFPI-PM) were thus prepared by the condensation polymerization of WuFDA with four commercial dianhydride 6FDA

BPDA

BTDA

and PMDA

respectively. The polyimides exhibited low dielectric constant

excellent thermal stability

outstanding solubility

good film-forming property

and mechanical properties. The dielectric constants of the polyimides were in the range of 2.28−2.88 (

= 10

Hz). The 5% weight-loss temperatures (

d5%

) in nitrogen were in the range of 555−584 °C

and the glass transition temperatures (

) were in the range of 408−448 °C. The weight loss of WuFPI-BP maintaining at 450 and 500 °C for half an hour was only 0.33% and 1.26%

respectively. All the WuFPIs could be dissolved in almost all organic solvents

even chloroform. The tensile strength and tensile modulus of these films were in the ranges of 78.6−85.7 MPa and 3.1−3.2 GPa

respectively. In addition

the polyimides displayed light color with special fluorescent and resistive switching (ON-OFF) characteristics; the maximum fluorescence emission was observed at 422−424 nm in NMP solution and at 470−548 nm in film state. The memory devices with the configuration of indium tin oxide/WuFPIs/aluminum (ITO/WuFPIs/Al) exhibited distinct volatile memory characteristics of static random access memory (SRAM)

with an ON/OFF current ratio of 10

−10

. These functional polyimides showed attractive potential applications in the field of high performance flexible polymer photoelectronic devices or polymer memory devices.

关键词

Keywords

references

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