Photosensitive Polyimide-silicone Copolymer based on Reaction Development Patterning (RDP)

Ōyama, Toshiyuki; Kasahara, Aya; Yasuda, Megumi; Takahashi, Akio

doi:10.2494/photopolymer.29.273

Cited by 6 publications

(3 citation statements)

References 19 publications

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“…Accordingly, the photosensitivity or responsibility of photosensitive groups is among the important factors for determining the resolution of micropatterns. 18 So far, numerous photosensitive groups have been used for PSPI, such as t-Boc, 19 DNQ groups, [20][21][22][23] and onitrobenzyl group (Nb) 17,[24][25][26][27][28] derivatives. Among them, Nb derivatives are well-known to be photocleavages by rearrangement mechanisms.…”

Section: Introductionmentioning

confidence: 99%

The improved photosensitivity of photosensitive polyimides containing o‐nitrobenzyl ether groups induced by the addition of photoacid generator

Song

Heo

Baek

et al. 2021

Journal of Polymer Science

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In this article, photosensitive polyimides (PSPIs) with photosensitive groups, o‐nitrobenzyl ether groups (Nb), were successfully synthesized based on 2,2′‐dihydroxy benzophenone‐3,3′,4,4′‐tetracarboxylic dianhydride and on diamine containing ethylene glycol chains (ODA). Also, a series of polyimide (PI), ODA‐1‐PI, ODA‐3‐PI, and ODA‐5‐PI with a number of ethylene glycol chains of 1, 3, and 5 were prepared to investigate the relationship between structure and solubility. Interestingly, ODA‐5‐PI, which possesses a large number of ethylene glycols, exhibited the most excellent solubility. Therefore, due to the good solubility of ODA‐5‐PI in organic solvents and alkaline solutions, a PSPI, poly(1,4‐phenyleneoxy‐3,6,9,12,15‐pentaoxaoctane‐1,4‐phenylene‐2,2′‐di[2‐nitrobenzyloxy]benzophenone‐3,3′,4,4′‐tetracarboxdiimide), named ODA‐5‐PSPI, was synthesized by linking Nb, which is a photosensitive group. Aiming at producing positive tone patterns, the synthesized ODA‐5‐PSPI was exposed to UV irradiation and then to a post‐exposure bake. Afterward, it was developed using a 2.38 wt% tetramethylammonium hydroxide solution. Furthermore, a photoacid generator (PAG) was additionally incorporated for a micropatterning process. Notably, in the presence of the PAG, the photocleavage of ODA‐5‐PSPI occurred not only by the intramolecular rearrangement of Nb but also by its hydrolysis reaction. As a result, due to the synergistic effect of photocleavage, the micropatterning of ODA‐5‐PSPI with PAG could be clearly obtained with less energy (2.0 J/cm2) compared with that without PAG (3.6 J/cm2). Therefore, through the addition of PAG, the photosensitivity was improved by 45%.

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Section: Introductionmentioning

confidence: 99%

The improved photosensitivity of photosensitive polyimides containing o‐nitrobenzyl ether groups induced by the addition of photoacid generator

Song

Heo

Baek

et al. 2021

Journal of Polymer Science

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“…Polyimide (PI) is one of the high-performance polymers. It exhibits excellent thermal, electrical, and mechanical properties, and consequently, it has been widely used in aerospace, electronics, and other industries. − PI can be copolymerized with a polyamide. The commercial polyamideimide (PAI) with the brand name of TorlonVR 4000TF has the superior properties of both polyamides and PIs, such as high mechanical strength, thermal resistance, and wide chemical resistance; hence, there are many developments for its application, including gas separation, nanofiltration, osmotic power generation, pervaporation, and so forth .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Thermostable Polyamideimides from Bis(2-aminoethyl)terephthalamide and Dianhydrides

et al. 2020

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Bis(2-aminoethyl)terephthalamide, an amide-containing diamine, was obtained from the aminolysis of waste poly(ethylene terephthalate) bottles. This diamine reacts with various aromatic dianhydrides to form novel polyamideimides (PAIs). The formation of amic acid or ammonium carboxylate salt intermediates depends strongly on the substituents of the dianhydrides. The electron-withdrawing substituents promote the creation of an ammonium carboxylate salt, whereas the electron donors assist with the amic acid intermediate formation. These salts and amic acids were further converted into polyimides by thermal treatment. The structures of the intermediates and PAIs were characterized by Fourier transform infrared, 1H nuclear magnetic resonance (NMR), and 13C NMR spectroscopies, and their thermal properties were determined by differential scanning calorimetry and thermogravimetry. X-ray diffraction patterns and inherent viscosity values of these PAIs were also reported. By using these chemical transformations, waste poly(ethylene terephthalate) bottles were converted into high-performance PAIs. These PAIs can be used as membrane-modifying agents for industrial separation applications.

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“…Organic polymer/silica hybrids often increase thermal stability, surface planarity and optical transparency as compared with the corresponding organic polymers [12][13][14]. In our previous work, PI-silicone copolymer afforded negative-tone pattern by RDP using tetramethylammonium hydroxide/water/NMP/methanol as developer [15]. The successful pattern formation probably indicated that RDP could be applied to any hybrid copolymers containing (-C(O)-X-) bonds.…”

Section: Introductionmentioning

confidence: 99%

Formation of Fine Pattern from Polyarylate-Silicone Copolymer by the Application of Reaction Development Patterning

Tokoro

Miyoshi

Ōyama

2017

J. Photopol. Sci. Technol.

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Multi-block copolymers between polyester (polyarylate) and polydimethylsiloxane were prepared by polycondensation using polydimethylsiloxane having p-hydroxyphenyl groups at its both chain ends as a diol monomer. The copolymer gave positive-tone fine pattern by the reaction development patterning with developer containing ethanolamine as a nucleophile. The silicone unit hybridized with polyarylate enabled pattern formation from dry film by contributing not only to high photosensitivity but also to high dissolution rate at the photoirradiated area. Use of polyarylate instead of the copolymer resulted in unsuccessful pattern formation from dry film.

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Photosensitive Polyimide-silicone Copolymer based on Reaction Development Patterning (RDP)

Cited by 6 publications

References 19 publications

The improved photosensitivity of photosensitive polyimides containing o‐nitrobenzyl ether groups induced by the addition of photoacid generator

The improved photosensitivity of photosensitive polyimides containing o‐nitrobenzyl ether groups induced by the addition of photoacid generator

Synthesis of Novel Thermostable Polyamideimides from Bis(2-aminoethyl)terephthalamide and Dianhydrides

Formation of Fine Pattern from Polyarylate-Silicone Copolymer by the Application of Reaction Development Patterning

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