Synthesis and characterization of a novel quaternary copolymerized thermoplastic copolyimide with excellent heat resistance, thermoplasticity, and solubility

Cao, Xiaohuan; Cai, Wei; He, Guoshan; Liu, X.

doi:10.3144/expresspolymlett.2020.62

Cited by 7 publications

(3 citation statements)

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“…Polyimide (PI) with high thermal stability has been widely applied in chip fabrication and the IC industry to promote the rapid development of aerospace, microelectronics, consumer electronics, and other fields. − In particular, thermoplastic polyimide (TPI), which incorporates excellent thermal stability and solubility as well as superior UV absorption and adhesion on various substrates, has attracted lots of attention from academia and industry, showing great potential in the application of advanced electronic packages. − However, the application of TPI in the field of TBDB materials is rarely reported. Very recently, our group proposed a series of quaternary copolymer TPIs, which were carefully tailored by introducing rigid biphenyl groups of 2,3,3′,4′-biphenyl tetracarboxylic dianhydride (a-BPDA), a flexible monomeric dianhydride of 2,3,3′,4′-oxidiphthalic anhydride (a-ODPA), and a rigid-flexible monomer diamine of 9,9′-bis (4-aminophenyl) fluorene (BAFL) and 1,3-bis (4′-aminophenoxy) benzene (TPE-R).…”

Section: Introductionmentioning

confidence: 99%

Controlled Thermal Imidization of Thermoplastic Polyimide for Temporary Bonding and Debonding in Advanced Packages

Huang

Liu

et al. 2022

ACS Appl. Polym. Mater.

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Temporary bonding and debonding (TBDB) is a key technology in the semiconductor field to enable 2.5D/3D integration of devices. However, the conventional polyimides, which serve as the laser-response material in TBDB, exhibit extremely poor solubility in aprotic polar solvents due to high-temperature imidization, limiting the cleaning process for wafers after debonding. Herein, a feasible method of controlling the curing temperature to enhance the solubility of thermoplastic polyimide (TPI) has been developed. The results proved that the ultimate solubility of TPI cured at 200 °C (TPI-200 °C) could be as high as 28.4 wt %. Besides, TPI-200 °C exhibits excellent heat resistance, outstanding mechanical properties, and ultrahigh absorptivity (99.96%) at a 355 nm UV wavelength. Meanwhile, we demonstrate the feasibility of the as-prepared TPI material for application in the TBDB process, showing excellent efficiency and low cost, and the follow-up elemental analysis of the cleaned wafer surfaces proved that TPI-200 °C can be completely removed after debonding. All these results demonstrate that TPI materials that can be used for TBDB are promising for ultrathin chip packaging and wafer level packaging (WLP) in the field of advanced electronic packaging.

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Section: Introductionmentioning

confidence: 99%

Controlled Thermal Imidization of Thermoplastic Polyimide for Temporary Bonding and Debonding in Advanced Packages

Huang

Liu

et al. 2022

ACS Appl. Polym. Mater.

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“…Cao et al. [ 15 ] prepared a new class of novel quaternary copolymerized thermoplastic polyimides and found that the large fluorenyl cardo groups, the noncoplanar structure, and the side methyl group can significantly reduce the interaction between PI molecular chains, resulting in the improvement of solubility and melt processability (thermoplasticity) of PI films. Furthermore, the large fluorenyl cardo groups of BAFL greatly enhanced the rigidity of the molecular skeleton, which significantly increased the heat resistance of polyimide.…”

Section: Introductionmentioning

confidence: 99%

Achieving Hydrophobic Ultralow Dielectric Constant Polyimide Composites: Combined Efforts of Fluorination and Porous Fillers

Zhao

et al. 2022

Macro Materials & Eng

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The advancement of the microelectronics industry necessitates the use of interlayer insulation materials with low dielectric constants and high mechanical properties. In this paper, a new type of copolymerized fluorinated polyimide (PI) is synthesized, and mixed with polyhedral oligomeric silsesquioxane (POSS) functionalized mesoporous silica (MCM-41@POSS). The PI/MCM-41@POSS composites exhibit good hydrophobicity. With the addition of 3 wt% MCM-41@POSS, the PI composite attained an ultralow dielectric constant (k = 1.88) and low dielectric loss (0.01) at 1 MHz, which is attributed to the mesoporous structure of MCM-41 and the restriction of polarization in the bonded region. The decorated POSS effectively prevents the penetration of PI molecular chains into the mesopores of MCM-41. In addition, the PI composites containing 3 wt% of MCM-41@POSS obtain the highest maximum stress of 104.03 MPa with an elongation at break of 13.73%. The hydrophobic PI composites with ultralow-k are expected to be good candidates as interlayer materials in microelectronics devices.

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“…In recent years, chemists have made many attempts to solve the solubility problem of polyimides. A series-copolymerized thermoplastic polyimides were successfully prepared using 3,4 0 -oxydiphthalic anhydride (a-ODPA), 4,4 0 -oxydiphthalicanhydride (s-ODPA), 9,9 0bis(4-aminophenyl)fluorene (BAFL), and 2,2-bis [4-(4-aminophenoxy)phenyl]propane (BAPP) by Cao et al 28 They reported the glass transition temperature (T g ) of these polyimides, with different ratios, to be in the range of 235-305 C. They were completely soluble in DMF, DMAc, and NMP within 3 h, indicating that they had excellent solubility. Furthermore, Kuang et al 29 successfully prepared a new diamine, namely, 10,10-bis [4-(4-aminophenoxy)-3-methylphenyl]-9(10H)-anthrone (BAMPA), which contains bulky 9(10H)-anthrone units.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of melt‐processable polyimides derived from diaminodiphenylsulfone and benzophenone tetracarboxylic dianhydride with excellent heat resistance and thermoplasticity

Zhou

Zhang

Mao

et al. 2021

J of Applied Polymer Sci

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Polyimide has excellent heat resistance, dielectric properties, and mechanical properties, and has a wide range of applications in aerospace, electronic packaging, and insulating materials. However, traditional polyimide is difficult to melt and dissolve, and its processing is difficult, which has become an important reason limiting its practical application. Therefore, the development of high temperature-resistant thermoplastic polyimide has become a research hotspot. To prepare high temperature-resistant thermoplastic polyimide materials, a series of thermoplastic polyimides was successfully prepared using 3,3 0 ,4,4 0 -benzophenone tetracarboxylic dianhydride, 3,3 0 -diaminodiphenylsulfone, 2,3 0 ,3,4 0 -benzophenone tetracarboxylic dianhydride, 9,9-bis(4-aminophenyl) fluorene, and 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane via a two-step method. The effects of non-coplanar structure and bulky groups on the solubility, processability, and thermal properties of polyimide were studied. The structure, heat resistance and thermoplasticity of polyimide were characterized via various methods. The results show that the glass transition temperature of the prepared thermoplastic polyimide is between 292 and 302 C, and has excellent thermal resistance. The processing viscosity of polyimides is as low as 9210 Pa.s, and it has a certain degree of processing properties. It may be designed to be used in high temperature-resistant hot melt adhesives for structural components, high temperature-resistant melt processing resins, or thermoplastic composite materials used in the field of aerospace in the future.

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Synthesis and characterization of a novel quaternary copolymerized thermoplastic copolyimide with excellent heat resistance, thermoplasticity, and solubility

Cited by 7 publications

References 0 publications

Controlled Thermal Imidization of Thermoplastic Polyimide for Temporary Bonding and Debonding in Advanced Packages

Controlled Thermal Imidization of Thermoplastic Polyimide for Temporary Bonding and Debonding in Advanced Packages

Achieving Hydrophobic Ultralow Dielectric Constant Polyimide Composites: Combined Efforts of Fluorination and Porous Fillers

Synthesis and characterization of melt‐processable polyimides derived from diaminodiphenylsulfone and benzophenone tetracarboxylic dianhydride with excellent heat resistance and thermoplasticity

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