High optical transparency, low dielectric constant and light color of organosoluble fluorinated polyimides based on 10,10-bis[4-(4-amino-3-trifluoromethylphenoxy)phenyl]-9(10H)-anthrone

Zhang, Ting; Pan, Yang; Cheng, Song; Huang, Bin; Huang, Zhengkai

doi:10.1007/s00289-019-02955-0

Cited by 13 publications

(5 citation statements)

References 35 publications

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“…The characteristic absorption band of PAA carboxyl group from 3200 to 2600 cm −1 was not observed in the spectra, and the characteristic peaks at 1378 cm −1 were attributed to CN stretching vibration of imide ring, which was newly formed after imidization. The peaks at 1780 and 1720 cm −1 belong to the asymmetric stretching vibration, symmetric stretching vibration of the imide ring, respectively, and peaks at 720 cm −1 were assigned to flexural vibration of the imide ring 29 . The results of FTIR proved the successful synthesis of PIs.…”

Section: Resultsmentioning

confidence: 83%

Synthesis and characterization of high fluorine‐containing polyimides with low‐dielectric constant

Cai

Cheng

2021

J of Applied Polymer Sci

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Aromatic polyimides (PI) with low‐dielectric constant are becoming more and more important with the continuous development of high‐speed communication technology. Herein, high fluorine‐containing PI with low‐dielectric constant was prepared. First, a novel aromatic diamine monomer 4,4′‐(3,3′‐bis[trifluoromethyl]biphenyl‐4,4′‐diyl)bis(oxy)bis(3‐[trifluoromethyl]aniline) bearing multi‐trifluoromethyl groups (12FDA) was synthesized and characterized. Subsequently, a series of PI with high‐fluorine content (HFPI) were obtained by two‐step polymerization of 12FDA with three commercial dianhydrides. The polymer films cured at a maximum temperature of 310°C showed excellent thermal and mechanical properties with high‐glass transition temperatures (>250°C) and high‐storage modulus (> = 2.0 GPa). The 5% weight loss temperatures of HFPIs were all above 500°C, which indicated that HFPIs exhibited excellent thermostability. Meanwhile, HFPI exhibited low‐water absorption (<0.3%) and low‐dielectric constant (2.40–2.68 at 1 MHz). The excellent thermal, mechanical, and electrical properties make it a promising dielectric material in electronics and communication industry.

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Section: Resultsmentioning

confidence: 83%

Synthesis and characterization of high fluorine‐containing polyimides with low‐dielectric constant

Cai

Cheng

2021

J of Applied Polymer Sci

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“…Excitingly, the enhanced refractive index of the PIDC was 0.1368 compared with PIC, which meant that the improvement effect of DAQ on the refractive index of PC was significantly better than that of BPEF. The structural difference of DAQ compared to BPEF lay in DAQ’s unique modified six-membered cardo-ring containing carbonyl groups, which made its molecular refractive index larger than that of BPEF, further inhibiting the close packing of polymer chains, thus facilitating the synthesis of PC with a higher refractive index . In addition, the birefringence of PCs was influenced by their structure and processing procedures.…”

Section: Results and Discussionmentioning

confidence: 99%

“…The structural difference of DAQ compared to BPEF lay in DAQ's unique modified sixmembered cardo-ring containing carbonyl groups, which made its molecular refractive index larger than that of BPEF, further inhibiting the close packing of polymer chains, thus facilitating the synthesis of PC with a higher refractive index. 43 In addition, the birefringence of PCs was influenced by their structure and processing procedures. In general, introducing aromatic rings into the polymer structure could lead to high birefringence due to the influence of the dipole moment.…”

Section: Optical Properties Of Pic and Pidcsmentioning

confidence: 99%

Design and Synthesis of Optical Biobased Polycarbonates with High Refractive Index and Low Birefringence

Li,

Wang,

Yan

et al. 2024

Ind. Eng. Chem. Res.

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Biobased poly(isosorbide carbonate) (PIC) has the advantages of renewable sources, nontoxic environmental resistance, and high transparency. However, the optical properties of PIC are limited by the rigid alicyclic skeleton within polymer chains, resulting in a low refractive index and high birefringence. In this work, a novel diether anthraquinone (DAQ) monomer containing an aromatic cardo-ring and carbonyl-modified side group was designed and synthesized, which successfully improved the refractive index and inhibited the birefringence by reducing optical anisotropy combined with increasing the molar refractive index of repeating units. To overcome the potential steric effect of DAQ and low activity of endo-OH groups on isosorbide (ISB), highly active choline tartaric acid (ChTa) ionic liquid catalysts were designed and evaluated systematically, resulting in a series of copolymers with sufficient M w (up to 140,800 g/mol). Notably, poly(ISB-co-DAQ carbonate) with 30/70 mol % of ISB/DAQ (PI 30 D 70 C) exhibited excellent optical properties with ignorable birefringence (Δn = 0.0005) and high transmittance (89%), and especially higher refractive index (n d = 1.6207) than PIC (n d = 1.4966) at 589 nm. Additionally, the copolycarbonates had excellent thermal, mechanical, and hydrophobicity properties, indicating their potential for optical applications and providing a strategy for designing optical polycarbonates.

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“…Due to the trifluoromethyl being a strong electronwithdrawing group with low electronic polarizability, the number of polarizable groups per unit volume is less. [33][34][35] In addition, the fluorinated substituent of HFBAPP has a high molar volume, which reduces the chain accumulation and the polarization density, so the dielectric constant of PI-5 is much lower than that of PI-1. In conclusion, because of the low ratio of polarizability over volume, the incorporation of fluorinated substituents polyimide has low dielectric constants and dielectric loss.…”

Section: Dielectric Propertiesmentioning

confidence: 99%

Synthesis of quaternary copolymerized fluorine-containing polyimides with good thermal properties and low dielectric constant

Zhao

Huang

et al. 2022

High Performance Polymers

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Novel fluorine-containing polyimides were synthesized through copolymerization by using 2,3,3′,4′-biphenyltetracarboxylic dianhydride (α-BPDA) and 4,4′-(4,4′-isopropydenediphenox-y) bis-(phthalic anhydride) (BPADA) as dianhydrides and 4,4′-oxydianiline (ODA) and 2,2 - Bis [4-(4-aminophenoxy)phenyl]-hexafluoropropanane (HFBAPP) as diamines. Noncoplanar structure, flexible ether bond, and trifluoromethyl give the polyimide good thermoplastic, solubility, and heat resistance. The glass transition temperatures of polyimide films are 232.5°C∼262.2°C, the 5% weight loss temperatures are 521.5°C∼531.0°C, and the residual mass is more than 50% as heating to 800°C. With the increase of HFBAPP content in diamine, the dielectric constant of the material decreases from 3.21 to 2.78, and the dielectric loss decreases from 0.00962 to 0.00687 at 1 MHz, which greatly improves the dielectric properties of the material.

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High optical transparency, low dielectric constant and light color of organosoluble fluorinated polyimides based on 10,10-bis[4-(4-amino-3-trifluoromethylphenoxy)phenyl]-9(10H)-anthrone

Cited by 13 publications

References 35 publications

Synthesis and characterization of high fluorine‐containing polyimides with low‐dielectric constant

Synthesis and characterization of high fluorine‐containing polyimides with low‐dielectric constant

Design and Synthesis of Optical Biobased Polycarbonates with High Refractive Index and Low Birefringence

Synthesis of quaternary copolymerized fluorine-containing polyimides with good thermal properties and low dielectric constant

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