Molecular design, synthesis and characterization of intrinsically black polyimide films with high thermal stability and good electrical properties

Zhang, Yan; Tan, Yansong; Liu, Jingang; Zhi, Xin‐xin; Huangfu, Meng‐ge; Jiang, Ganglan; Wu, Xiaowen; Zhang, Xiumin

doi:10.1007/s10965-019-1835-0

Cited by 27 publications

(15 citation statements)

References 26 publications

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“…Thus, it is a changeling research topic to develop polymer optical films with both of excellent thermal stability and good optical transparency [5][6][7].In recent years, the research progress of colorless and transparent polyimide (CPI) films has attracted great attention in the research and development of high performance polymer optical films [8][9][10]. 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].…”

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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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“…N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), and other solvents were obtained from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan) and purified by distillation prior to use. 4,4 -Iminodianiline (NDA) was synthesized in our laboratory [26] and purified by recrystallization from absolute ethanol under the protection of high-purity nitrogen. Pure NDA diamine was obtained as colorless needles with the purity of 99.5% according to the gas chromatography analysis.…”

Section: Methodsmentioning

confidence: 99%

“…In our previous work, a series of intrinsically black PI films were developed by the introduction of imino (-NH-) units in the standard PMDA-ODA film via the copolymerization of an aromatic diamine, 4,4 -iminodianiline (NDA) [26]. The imino (-NH-) unit present in the NDA molecular structure can be oxidized in the presence of trace oxygen, resulting in the black color of the PI films.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Properties of Inherently Black Polyimide Films with Extremely Low Coefficients of Thermal Expansion and Potential Applications for Black Flexible Copper Clad Laminates

et al. 2020

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In the current work, a series of black polyimide (PI) films with excellent thermal and dimensional stability at elevated temperatures were successfully developed. For this purpose, two aromatic diamines including 4,4′-iminodianline (NDA) and 2-(4-aminophenyl)-5- aminobenzimidazole (APBI) were copolymerized with pyromellitic dianhydride (PMDA) to afford PIs containing imino groups (–NH–) in the molecular structures. The referenced PI film, PI-ref, was simultaneously prepared from PMDA and 4,4′-oxydianiline (ODA). The introduction of imino groups endowed the PI films with excellent blackness and opaqueness with the optical transmittance lower than 2% at the wavelength of 600 nm at a thickness of 25 μm and lightness (L*) below 10 for the CIE (Commission International Eclairage) Lab optical parameters. Meanwhile, the introduction of rigid benzimidazole units apparently improved the thermal and dimensional stability of the PI films. The PI-d film based on PMDA and mixed diamines (NDA:APBI = 70:30, molar ratio) showed a glass transition temperature (Tg) of 445.5 °C and a coefficient of thermal expansion (CTE) of 8.9 × 10−6/K in the temperature range of 50 to 250 °C, respectively. It is obviously superior to those of the PI-a (PMDA-NDA, Tg = 431.6 °C; CTE = 18.8 × 10−6/K) and PI-ref (PMDA-ODA, Tg = 418.8 °C; CTE: 29.5 × 10−6/K) films.

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“…They first prepared an intrinsic BPI by polymerizing an electron-rich aromatic diamine, 4,4′-diaminodiphenylamine, with 1,2,4,5-benzenetetracarboxylic dianhydride (PMDA). Compared with the Kapton film with a UV cut-off wavelength (λ cut ) of 428 nm, its λ cut increased to 555 nm . Subsequently, with the purpose of application in flexible circuit boards, the authors co-polymerized a benzimidazole monomer into the BPI backbone to decrease its thermal expansion coefficient .…”

Section: Introductionmentioning

confidence: 99%

Intrinsically Black Polyimide with Retained Insulation and Thermal Properties: A Black Anthraquinone Derivative Capable of Linear Copolymerization

et al. 2021

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Black polyimide (BPI) is increasingly in demand for the development of photoelectric devices in place of yellow transparent polyimide, but BPI doped with carbon black shows serious insulation and mechanical performance deficiencies due to pinholes and uneven dispersion. Intrinsically BPI has thus attracted increasing interest in science and industry. Anthraquinone derivatives have an ample high molar extinction coefficient (ε), and appending as many auxochromes (−OH and −NH2) as possible on the anthraquinone skeleton can extend its light absorption range, thereby achieving complete UV–visible light absorption. However, the greatest obstacle to its application in BPI is retaining the monomer bifunctionality to avoid gel formation. In this work, a linearly polymerizable anthraquinone derivative, 2,4,5,7-tetraamino-1,8-dihydroxyanthracene-9,10-dione (4NADA), has been developed. Structural analysis of this monomer bearing multiple active groups by 1H NMR, Fourier-transform infrared, and theoretical calculations has demonstrated that the auxochrome groups show different nucleophilic activities owing to the formation of intramolecular hydrogen bonds, such that only p-amino groups (2- and 7-positions) can participate in the polymerization reaction. Subsequently, 4NADA was copolymerized into a Kapton-type polyimide. We found that low-level introduction of 4NADA (4%) afforded a spectrally BPI film that maintained the electrical insulation and heat resistance properties of polyimide. This method, equivalent to embedding a black monomer in polyimide chains, has merits of economy, universality, process consistency, ready accessibility, and superior performance.

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Molecular design, synthesis and characterization of intrinsically black polyimide films with high thermal stability and good electrical properties

Cited by 27 publications

References 26 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

Preparation and Properties of Inherently Black Polyimide Films with Extremely Low Coefficients of Thermal Expansion and Potential Applications for Black Flexible Copper Clad Laminates

Intrinsically Black Polyimide with Retained Insulation and Thermal Properties: A Black Anthraquinone Derivative Capable of Linear Copolymerization

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