Norbornene end-capped polyimide for low CTE and low residual stress with changes in the diamine linkages

Yoo, Taewon; Kim, Kwangin; Han, Patrick; Jang, Wonbong; Han, Haksoo

doi:10.1007/s13233-015-3104-3

Cited by 16 publications

(6 citation statements)

References 34 publications

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“…22,23 A few studies have been involved to look for the ways to decrease the CTE values of PIs. 24 –26 In this work, we found that CTE was influenced by the chain rigidity and the existence of –CN groups. For each series, the PMDA-based PI had the lowest CTE value, and the one from 6FDA had highest CTE.…”

Section: Resultsmentioning

confidence: 63%

Synthesis and properties of the novel polyimides containing cyano and biphenyl moieties

Liu

Shen

et al. 2017

High Performance Polymers

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A series of cyano-functionalized polyimides (CN-PIs) were prepared and derived from a novel diamine monomer having cyano and biphenyl groups. Meanwhile, another series of PIs without cyano groups (H-PIs) were prepared as counterparts for comparison purposes. Both series of PIs exhibited good solvent resistance, good thermal stability, remarkable film-forming ability, and excellent tensile properties. The Tg values of CN-PIs were 260–330°C, which were 10–17°C higher than the corresponding –CN free H-PIs. The CN-PIs exhibited no obvious decomposition below 470°C, and their 5% weight loss temperatures were above 568°C under nitrogen atmosphere. All the CN-PI films had high tensile strength and Young’s moduli, which were related to their rigid backbones and strong interactions between molecular chains. Due to their higher molar polarization, CN-PIs expressed the higher dielectric constants (3.29–3.69 at 1 MHz) in comparison with the corresponding H-PIs. CN-PIs exhibited the improved transparency, and both CN-PIs and H-PIs had better transparency than commercial Kapton® film. Introducing –CN groups could have an effect on the coefficient of thermal expansion and peel strength of the PIs. The peel strength of the PI, which was derived from cyano-functionalized diamine monomer and 4,4′-oxydiphthalic anhydride, could even reach 1.10 N mm-1, suggesting its strong interaction to copper matrix and potential use in flexible circuit board.

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Section: Resultsmentioning

confidence: 63%

Synthesis and properties of the novel polyimides containing cyano and biphenyl moieties

Liu

Shen

et al. 2017

High Performance Polymers

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“…The modulus and CTE play a leading role in determining the shrinkage behavior of epoxy resins. Therefore, cyclic stress is a function of the CTE and modulus of the film with temperature 33 . The stress values obtained by using the theoretical calculation equations from the modulus, CTE, and T g are also listed in Table 2.…”

Section: Resultsmentioning

confidence: 99%

Residual stress and thermal properties of rubber‐modified epoxy systems for semiconductor package

Zhang

Wang

et al. 2021

J of Applied Polymer Sci

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The thermal and mechanical breakage of epoxy coating due to easy cracking, poor toughness, and large residual stress, occurring during curing and thermal aging process, is the key factor responsible for damage of silicon device on semiconductor elements. In this study, modified epoxy resins containing an imide ring and polybutadiene rubber‐modified epoxy resin used as the toughening agents were prepared to investigate the residual stress generated during the curing and thermal aging process. The curing process and the thermal properties of the modified epoxy systems were assessed by differential scanning calorimetry and rotational rheometry, dynamic thermomechanical analysis, thermomechanical analysis, and thermogravimetric analysis. A thin film stress analyzer was used to analyze the changes in thermal stress of the modified epoxy systems during curing and cyclic stress and compared with the data from theoretical calculation. The results show that, with the increase in content of the toughening agent, the toughness of the modified epoxy systems was significantly improved, and the curing and thermal cycle stresses could be simultaneously reduced. Besides, we also envision the extension of the comprehensive evaluation method for residual stress described in this study to enable the modification of epoxy coatings prepared using a toughening agent, in the near future.

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“…Although the exact mechanism of CTE is uncertain and controversial, 40 many works also reported that the value of CTE decreases with the development of intra-chain rigidity. [41][42][43] In our previous work, 44 we raised the possible mechanism of negative CTE on b-H-H-APA+PMDA PI. And now, for b-H-MeO-APA+PMDA PI, its CTE value is also negative, which further confirming that the thermal shrinkage behavior in the in-plane direction is possibly an essential feature for b-H-H(MeO)-APA+ PMDA PIs.…”

Section: Thermal and Mechanical Properties Of B-h-meo-apis Filmsmentioning

confidence: 99%

The role of intramolecular and intermolecular hydrogen bonding effect for adenine-containing polyimide films

Chen

Zheng

et al. 2022

High Performance Polymers

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A series of adenine-containing polyimides (APIs) with intramolecular hydrogen bonding (HB) were prepared from N 1 -(9-(4-aminophenyl)- 9H-purin-6-yl)-2-methoxybenzene-1,4-diamine (b-H-MeO-APA) and commercial dianhydrides. And a systematic comparison between intramolecular and intermolecular HB effects was made using APIs with (b-H-MeO-APIs) and without (b-H-H-API) methoxy group. FTIR indicated that the occurrence of intramolecular HB originated from the side MeO group ortho to -NH-. XRD indicated that the introduction of side group MeO and corresponding intramolecular HB could destroy the orderly stacking of b-H-H-APIs. Birefringence and polarized ATR FTIR studies showed that the groups and chains in b-H-MeO-APIs films could also be simultaneously self-arranged in the in-plane direction. In contrast, the orientation degree in the in-plane direction is generally lower than that of b-H-H-APIs. The b-H-MeO-APIs films showed lower water absorption, higher Tg, and lower CTE compared to b-H-H-APIs films, which indicates that the introduction of intramolecular HB may have some positive influence in controlling water absorption, Tg, and CTE.

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Norbornene end-capped polyimide for low CTE and low residual stress with changes in the diamine linkages

Cited by 16 publications

References 34 publications

Synthesis and properties of the novel polyimides containing cyano and biphenyl moieties

Synthesis and properties of the novel polyimides containing cyano and biphenyl moieties

Residual stress and thermal properties of rubber‐modified epoxy systems for semiconductor package

The role of intramolecular and intermolecular hydrogen bonding effect for adenine-containing polyimide films

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