Poly(ester imide)s possessing low coefficients of thermal expansion (CTE) and low water absorption (III). Use of bis(4-aminophenyl)terephthalate and effect of substituents

Hasegawa, Masatoshi; Sakamoto, Yuichi; Tanaka, Yuma; Kobayashi, Yoshihiro

doi:10.1016/j.eurpolymj.2010.04.014

Cited by 90 publications

(49 citation statements)

References 24 publications

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“…To date, we have investigated aromatic poly(ester imide)s (PEsIs) as promising candidates for new dielectric substrate materials for FPC applications [11][12][13][14]. For example, longitudinal structural extension of ester-linked tetracarboxylic dianhydrides, as shown in Figure 1(left), was very effective in achieving excellent combined properties, i.e., a very high Tg, an ultralow coefficient of thermal expansion (CTE), an extremely low coefficient of hygroscopic expansion (CHE), high flame retardancy, sufficient film ductility, and a low tan δ at 10 GHz [14].…”

Section: Introductionmentioning

confidence: 99%

Poly(ester imide)s Possessing Low Coefficients of Thermal Expansion and Low Water Absorption (V). Effects of Ester-linked Diamines with Different Lengths and Substituents

Hasegawa

Hishiki

2020

Polymers

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A series of ester-linked diamines, with different lengths and substituents, was synthesized to obtain poly(ester imide)s (PEsIs) having improved properties. A substituent-free ester-linked diamine (AB-HQ) was poorly soluble in N-methyl-2-pyrrolidone at room temperature, which forced the need for polyaddition by adding tetracarboxylic dianhydride solid into a hot diamine solution. This procedure enabled the smooth progress of polymerization, however, accompanied by a significant decrease in the molecular weights of poly(amic acid)s (PAAs), particularly when using hydrolytically less stable pyromellitic dianhydride. On the other hand, the incorporation of various substituents (–CH3, –OCH3, and phenyl groups) to AB-HQ was highly effective in improving diamine solubility, which enabled the application of the simple polymerization process without the initial heating of the diamine solutions, and led to PAAs with sufficiently high molecular weights. The introduction of bulkier phenyl substituent tends to increase the coefficients of thermal expansion (CTE) of the PEsI films, in contrast to that of the small substituents (–CH3, –OCH3). The effects of ester-linked diamines, consisting of longitudinally further extended structures, were also investigated. However, this approach was unsuccessful due to the solubility problems of these diamines. Consequently, the CTE values of the PEsIs, obtained using longitudinally further extended diamines, were not as low as we had expected initially. The effects of substituent bulkiness on the target properties, and the dominant factors for water uptake (WA) and the coefficients of hygroscopic expansion (CHE), are also discussed in this study. The PEsI derived from methoxy-sustituted AB-HQ analog and 3,3′,4,4′-biphenyltetracarboxylic dianhydride achieved well-balanced properties, i.e., a very high Tg (424 °C), a very low CTE (5.6 ppm K−1), a low WA (0.41%), a very low CHE value (3.1 ppm/RH%), and sufficient ductility, although the 26 μm-thick film narrowly missed certification of the V-0 standard in the UL-94V test. This PEsI film also displayed a moderate εr (3.18) and a low tan δ (3.14 × 10−3) at 10 GHz under 50% RH and at 23 °C. Thus, this PEsI system is a promising candidate as a novel dielectric substrate material for use in the next generation of high-performance flexible printed circuit boards operating at higher frequencies (≥10 GHz).

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Section: Introductionmentioning

confidence: 99%

Poly(ester imide)s Possessing Low Coefficients of Thermal Expansion and Low Water Absorption (V). Effects of Ester-linked Diamines with Different Lengths and Substituents

Hasegawa

Hishiki

2020

Polymers

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“…Compared with the fluorine-containing CPI films, the semi-alicyclic ones usually have the advantages of lower curing temperature and higher optical transmittance; however, higher CTE values [24]. Various efforts have been carried out in the literature to reduce the CTE values of semi-alicyclic CPI films, which can be characterized by the systematical and pioneering work reported by Hasegawa and coworkers [25][26][27][28][29]. Rigid ester bonds and amide bonds have been introduced into the molecular structures of the CPIs and the optical films with apparently reduced CTEs were successfully achieved.…”

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confidence: 99%

Reduced Coefficients of Linear Thermal Expansion of Colorless and Transparent Semi-Alicyclic Polyimide Films via Incorporation of Rigid-Rod Amide Moiety: Preparation and Properties

Jiang

Wang

et al. 2020

Polymers

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Semi-alicyclic colorless and transparent polyimide (CPI) films usually suffer from the high linear coefficients of thermal expansion (CTEs) due to the intrinsic thermo-sensitive alicyclic segments in the polymers. A series of semi-alicyclic CPI films containing rigid-rod amide moieties were successfully prepared in the current work in order to reduce the CTEs of the CPI films while maintaining their original optical transparency and solution-processability. For this purpose, two alicyclic dianhydrides, hydrogenated pyromellitic anhydride (HPMDA, I), and hydrogenated 3,3',4,4'-biphenyltetracarboxylic dianhydride (HBPDA, II) were polymerized with two amide-bridged aromatic diamines, 2-methyl-4,4'-diaminobenzanilide (MeDABA, a) and 2-chloro-4,4'-diaminobenzanilide (ClDABA, b) respectively to afford four CPI resins. The derived CPI resins were all soluble in polar aprotic solvents, including N-methyl-2-pyrrolidone (NMP) and N,N-dimethylacetamide (DMAc). Flexible and tough CPI films were successfully prepared by casing the PI solutions onto glass substrates followed by thermally cured at elevated temperatures from 80 • C to 250 • C. The MeDABA derived PI-I a (HPMDA-MeDABA) and PI-II a (HBPDA-MeDABA) exhibited superior optical transparency compared to those derived from ClDABA (PI-I b and PI-II b ). PI-I a and PI-II a showed the optical transmittances of 82.3% and 85.8% at the wavelength of 400 nm with a thickness around 25 µm, respectively. Introduction of rigid-rod amide moiety endowed the HPMDA-PI films good thermal stability at elevated temperatures with the CTE values of 33.4 × 10 −6 /K for PI-I a and 27.7 × 10 −6 /K for PI-I b in the temperature range of 50-250 • C. Comparatively, the HBPDA-PI films exhibited much higher CTE values. In addition, the HPMDA-PI films exhibited good thermal stability with the 5% weight loss temperatures (T 5% ) higher than 430 • C and glass transition temperatures (T g ) in the range of 349-351 • C.The polymeric optical films with high thermal stability, high dimensional stability at elevated temperatures, high optical transparency, and high tensile properties are highly desired in modern optoelectronic areas, such as substrates or covering windows for flexible active matrix organic light-emitting diodes (AMOLED) devices, substrates for organic photovoltaic (OPV) solar cells, and so on [1][2][3]. Conventional polymeric optical films, such as polyolefin and polyester films usually suffer from the poor thermal and dimensional stability while the standard high-temperature resistant polymer films, such as the wholly aromatic polyimide (PI) films often exhibit highly colored appearance and poor optical transparency in the visible light region [4]. That is to say, the molecular structure factors that affect the optical and thermal properties of polymer films are usually contradictory. The structural factors that can improve the thermal stability of polymer films often reduce the optical properties of the films at the same time, and vice versa. Thus, it is a changeling research topic to dev...

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“…In addition to the properties mentioned above, other properties are also desired such as lower linear coe cients of thermal expansion, lower extents of moisture uptakes, low coe cients of humidity expansion and su cient toughness. The ester linkages in the title compound contribute to the sti ness of the structure, consequently reducing CTE of the derived PIs [2]. The introduction of uoro groups also decreases water absorption of the polyimide lms.…”

Section: Atom Sitementioning

confidence: 99%

Crystal structure of bis(2-fluoro-4-nitrophenyl) terephthalate C₂₀H₁₀F₂N₂O₈

Chen

Yang

2016

Zeitschrift Für Kristallographie - New Crystal Structures

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Poly(ester imide)s possessing low coefficients of thermal expansion (CTE) and low water absorption (III). Use of bis(4-aminophenyl)terephthalate and effect of substituents

Cited by 90 publications

References 24 publications

Poly(ester imide)s Possessing Low Coefficients of Thermal Expansion and Low Water Absorption (V). Effects of Ester-linked Diamines with Different Lengths and Substituents

Poly(ester imide)s Possessing Low Coefficients of Thermal Expansion and Low Water Absorption (V). Effects of Ester-linked Diamines with Different Lengths and Substituents

Reduced Coefficients of Linear Thermal Expansion of Colorless and Transparent Semi-Alicyclic Polyimide Films via Incorporation of Rigid-Rod Amide Moiety: Preparation and Properties

Crystal structure of bis(2-fluoro-4-nitrophenyl) terephthalate C₂₀H₁₀F₂N₂O₈

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Poly(ester imide)s possessing low coefficients of thermal expansion (CTE) and low water absorption (III). Use of bis(4-aminophenyl)terephthalate and effect of substituents

Cited by 90 publications

References 24 publications

Poly(ester imide)s Possessing Low Coefficients of Thermal Expansion and Low Water Absorption (V). Effects of Ester-linked Diamines with Different Lengths and Substituents

Poly(ester imide)s Possessing Low Coefficients of Thermal Expansion and Low Water Absorption (V). Effects of Ester-linked Diamines with Different Lengths and Substituents

Reduced Coefficients of Linear Thermal Expansion of Colorless and Transparent Semi-Alicyclic Polyimide Films via Incorporation of Rigid-Rod Amide Moiety: Preparation and Properties

Crystal structure of bis(2-fluoro-4-nitrophenyl) terephthalate C20H10F2N2O8

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Crystal structure of bis(2-fluoro-4-nitrophenyl) terephthalate C₂₀H₁₀F₂N₂O₈