Benzocyclobutene/vinylphenyl-introduced polycarbosilanes with low dielectric constant, high temperature performance and photopatternability

Hu, Huan; Liu, Huan; Zheng, Liping; Zhao, Cui‐Hua; Huang, Yawen; Chang, Guanjun; Yang, Junxiao

doi:10.1016/j.polymer.2015.04.028

Cited by 42 publications

(33 citation statements)

References 53 publications

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“…Silacyclobutene was a type of cyclic structure which was generally used for ring‐opening polymerization to produce polycarbosilanes. Such polymers have been demonstrated as a high temperature and low dielectric material . From another point of view, silacyclobutene could also be taken as a reactive group to serve as crosslinking site.…”

Section: Introductionmentioning

confidence: 99%

Photoactive Polymers with Benzocyclobutene/Silacyclobutane Dual Crosslinked Structure and Low Dielectric Constant

Huang

Zhang

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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Low dielectric photopatternable materials have aroused much interest owing to their potential application as alternatives of conventional photoresists. Although a number of photosensitive groups have been established to construct photopatternable materials for many years, it is still a challenge to introduce them into polymer chains via a facile and control polymerization technique, such as living free radical polymerization. In this work, on the basis of the photoactive silaycyclobutene moiety, a new monomer, 1‐methyl‐1‐(4‐vinylphenyl) silacyclobutane (1‐MVPSCB), was synthesized and demonstrated successful to conduct atom transfer radical polymerization (ATRP). Subsequently, the copolymerization of 1‐MVPSCB with 4‐vinylbenzocyclobutene (4‐VBCB) and styrene produced a kind of benzocyclobutene/silacyclobutane double‐crosslinked polymer (BS‐DCP) with controlled benzocyclobutene/silacyclobutane ratios and low polydispersity index. Owing to the UV/thermally dual crosslinked structure, BS‐DCP possesses photapatternability, high dimensional stability and low dielectric constant (2.37 at 10 MHz). These properties make BS‐DCP a potential photoresist that could be directly used as interconnected dielectrics. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 1920–1928

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Section: Introductionmentioning

confidence: 99%

Photoactive Polymers with Benzocyclobutene/Silacyclobutane Dual Crosslinked Structure and Low Dielectric Constant

Huang

Zhang

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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“…On the other hand, the peaks assigned to methyl (1345 cm −1 ) and carbonyl (1725 cm −1 ) groups of the methacrylate moiety almost accorded before and after annealing of poly‐BCBMA. This result means that the dibenzocyclooctadiene structure was constructed with two units of BCB moieties between the side chains …”

Section: Resultsmentioning

confidence: 99%

Synthesis of polymethacrylate‐bearing benzocyclobutene structure and extension to networked polymer based on thermal isomerization

Komeda

Shintaro

Yoshida

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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1‐Benzocyclobutenyl methacrylate‐bearing methacrylate (BCBMA) backbone has been synthesized, and radical polymerization of the monomer was performed by utilizing 2, 2′‐azobisisobutyronitrile (AIBN) as initiator to result poly‐BCBMA. Differential scanning calorimetry (DSC) measurement of the derived poly‐BCBMA revealed the lowering of thermal isomerization temperature from that of nonsubstituted benzocyclobutene. The thermal decomposition temperature of BCBMA before and after thermal treatment was confirmed by thermogravimetric analysis (TGA). The results of the TGA observation did not show significant difference in both 5% and 10% weight loss temperature (Td5 and Td10). This result suggests that the thermal conversion of the poly‐BCBMA to the networked polymer take place without thermal decomposition of the main chain based on the methacrylate framework. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2175–2180

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“…Organosilicon polymeric resins are a family of resins based on polysiloxanes or polycarbosilanes. They are also considered as candidates for low‐ k polymeric materials because of their low k and high thermal resistance values . In particular, polysiloxane‐based resins have been studied extensively as well‐established and industrialized materials.…”

Section: Introductionmentioning

confidence: 99%

Low‐dielectric‐constant benzocyclobutene–organosilicon resins constructed from cyclotetrasiloxane

Huang

Zhang

Peng

et al. 2019

J of Applied Polymer Sci

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Organosilicon resins have been demonstrated to be promising materials for low-dielectric-constant (low-k) related applications. In this study, we proposed a method to further reduce the dielectric constant (k) value of organosilicon resins with [1,1-dimethyl,1-(4 0 -benzocyclobutenyl)silyl] cyclotetrasiloxane (BCB-D4) as a building block. This building block was prepared by the hydrosilylation reaction of tetravinyl cyclotetrasiloxane with dimethyl-benzocyclobutene-silane. The reaction of benzocyclobutene on BCB-D4 by bulk polymerization in modules directly produced a highly crosslinked resin (poly{[1,1-dimethyl,1-(4 0 -benzocyclobutenyl)silyl] cyclotetrasiloxane) [poly(BCB-D4)]). Poly(BCB-D4) exhibited a low k of about 2.70; this value was greatly lower than the k (~3.0) of conventional benzocyclobutene-organosilicon resins obtained by the curing of linear polysiloxane. The low k was possibly due to the porous structure, which was constructed from multifunctionalized and cyclic building blocks. In addition, poly(BCB-D4) also exhibited a relatively high modulus (5.0 GPa) without a sacrifice in the thermal resistance.

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Benzocyclobutene/vinylphenyl-introduced polycarbosilanes with low dielectric constant, high temperature performance and photopatternability

Cited by 42 publications

References 53 publications

Photoactive Polymers with Benzocyclobutene/Silacyclobutane Dual Crosslinked Structure and Low Dielectric Constant

Photoactive Polymers with Benzocyclobutene/Silacyclobutane Dual Crosslinked Structure and Low Dielectric Constant

Synthesis of polymethacrylate‐bearing benzocyclobutene structure and extension to networked polymer based on thermal isomerization

Low‐dielectric‐constant benzocyclobutene–organosilicon resins constructed from cyclotetrasiloxane

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