Colorless polyimides derived from 2R,5R,7S,10S-naphthanetetracarboxylic dianhydride

Hu, Xiaofan; Jiang, Yan; Wang, Yongxia; Mu, Hongliang; Wang, Zikun; Cheng, Haiyang; Zhao, Fengyu; Zhen, Wang

doi:10.1039/c7py01048f

Cited by 65 publications

(53 citation statements)

References 56 publications

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“…Based on the previous decades of research on the origination of coloration in traditional all-aromatic PI films, the researchers revealed many effective procedures to prohibit the formation of intra-or intermolecular charge transfer complexes (CTC) between the electron-donating diamine moiety and the electron-accepting dianhydride moiety so as to improve the optical transparency of the PI films [11][12][13]. At present, the effective means to develop CPI films mainly include introducing groups with high electronegativity characteristics, such as trifluoromethyl groups, sulphone groups, or substituents with non-conjugated characteristics, such as aliphatic or alicyclic groups, or groups with large molar volume-such as naphthalene, fluorene, or cardo groups-into the PI molecular chains [14][15][16][17][18][19][20]. Although various CPI films have been developed in the literature by these methodologies, much of them still cannot be practically used due to the absence of dimensional stability at elevated temperatures.…”

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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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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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“…Hu et al. prepared an alicyclic dianhydride, 2R,5R,7S,10S‐naphthanetetracarboxylic dianhydride (HNTDA), through the hydrogenation of tetramethyl‐1,4,5,8‐naphthalenetetracarboxylate, followed by hydrolysis, acidification, and dehydration ( Scheme ) . HNTDA‐based PIs were colorless or pale‐yellow, depending on the structures of the diamines.…”

Section: Recent Design Approaches To Prepare Cpismentioning

confidence: 99%

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

Tapaswi

2019

Macro Chemistry & Physics

165

155

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Recently, colorless and transparent plastic substrates with high glass transition temperature and suitable thermo‐mechanical properties are in high demand in optoelectronic device industries, due to their various optical applications. Colorless polyimides (CPIs) exhibit both high thermo‐mechanical stability as well as high transparency that are suitable for optoelectronic applications. The most recent (2010–2018) developments on CPIs, in terms of design and synthesis of new monomers and their effects on the thermo‐optical properties of the obtained CPIs, are reviewed in this article.

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“…Simultaneously these approaches could also improve the processability of PIs, but inevitably accompanying with the thermostability of PIs decreasing and the CTE or synthetic cost increasing. 7–15…”

Section: Introductionmentioning

confidence: 99%

Optically Transparent and Thermal‐Stable Polyimide Films Derived from a Semi‐Aliphatic Diamine: Synthesis and Properties

Chen

et al. 2020

Macro Chemistry & Physics

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A novel semi‐aliphatic diamine with bulky cyclohexyl and ortho‐substituted tertiary butyl groups (4,4'‐(cyclohexylmethylene)bis(2‐(tert‐butyl)aniline), CHMBTBA) is synthesized via Mannich and rearrangement reactions of cyclohexanecarboxaldehyde and 2‐tert‐butylaniline. Afterward, several semi‐aliphatic polyimides are prepared by the high‐temperature one‐pot polymerization of CHMBTBA with various aromatic dianhydrides respectively. The resulting PIs exhibit outstanding solubility in common organic solvents (i.e., trichloromethane, etc.) and are easily processed into light color or colorless transparent films (thickness: 25 ± 1 µm) by the blade coating of polymer solution. The transmittance of all resulting films is above 86% in the visible light region (400–760 nm). Their glass transition temperatures exceed 310 °C and reach even to 374 °C (by differential scanning calorimetry). They also display low water absorption (0.29–0.87%) and good mechanical properties (tensile strength: 50.9–87.7 MPa, Young's modulus: 2.0‐2.5 GPa, elongation at break: 3.8–7.6%). Thus, they are promising potential candidates for flexible display substrates.

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Colorless polyimides derived from 2R,5R,7S,10S-naphthanetetracarboxylic dianhydride

Abstract: Colorless polyimides with excellent thermal and mechanical properties were developed from 2R,5R,7S,10S-naphthanetetracarboxylic dianhydride, and their properties were systematically compared with those based on 1S,2R,4S,5R-cyclohexanetetracarboxylic dianhydride.

Cited by 65 publications

References 56 publications

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

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

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

Optically Transparent and Thermal‐Stable Polyimide Films Derived from a Semi‐Aliphatic Diamine: Synthesis and Properties

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