A Negative Type Photosensitive Polymer Based on Poly(naphthylene ether), a Cross-Linker, and a Photoacid Generator with Low Dielectric Constant

Tsuchiya, Kousuke; Shibasaki, Yuji; Ueda, Mitsuru

doi:10.1295/polymj.pj2006213

Cited by 10 publications

(11 citation statements)

References 17 publications

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“…PPE has a low dielectric constant (ε), which should be kept in the PSPPE. The ε of a polymer film at 1 MHz is estimated from the refractive index ( n ) of the film according to the modified Maxwell's equation, ε = 1.0 n 2 AV 5, 11, 12. The films of PPE and PSPPE on quartz were prepared by spin‐casting from their toluene solutions, and then these films were dried at 150 °C for 6 h in vacuo .…”

Section: Resultsmentioning

confidence: 99%

“…Photosensitive poly(imide)s (PSPIs) and poly (benzoxazole)s (PSPBOs) have been widely applied as stress buffer and insulation layers in semiconductor manufacturing because of their excellent thermal and reasonably dielectric properties 1–4. The next generation microelectronic devices require high‐performance dielectrics having a low dielectric constant (ε), a low dissipation factor, low moisture uptake, and thermal stability such as high glass transition temperature ( T g ) 5, 6. Unfortunately, PSPIs and PSPBOs cannot promise the aforementioned demands such as the low dielectric constant because of the existence of polar units in polymer backbone, except for costly perfluorinated and semialicyclic ones 7, 8…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3][4] The next generation microelectronic devices require high-performance dielectrics having a low dielectric constant (e), a low dissipation factor, low moisture uptake, and thermal stability such as high glass transition temperature (T g ). 5,6 Unfortunately, PSPIs and PSPBOs cannot promise the aforementioned demands such as the low dielectric constant because of the existence of polar units in polymer backbone, except for costly perfluorinated and semialicyclic ones. 7,8 A typical engineering plastic poly(2,6-dimethyl-1,4-phenylene ether) (PPE) is one of the potential candidates due to the low-e (2.5) and low moisture uptake (<0.05 wt %), but its T g is about 210 8C, which is inadequate for solder resistance.…”

Section: Introductionmentioning

confidence: 99%

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Negative‐type photosensitive poly(phenylene ether) based on poly(2,6‐dimethyl‐1,4‐phenylene ether), a crosslinker, and a photoacid generator

Mizoguchi¹,

Ueda²

2008

J. Polym. Sci. A Polym. Chem.

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A negative‐type photosensitive poly(phenylene ether) (PSPPE) based on poly(2,6‐dimethyl‐1,4‐phenylene ether) (PPE), a novel crosslinker 4,4′‐methylene‐bis [2,6‐bis(methoxymethyl)phenol] (MBMP) having good compatibility with PPE, and diphenylidonium 9,10‐dimethoxy anthracene‐2‐sulfonate (DIAS) as a photoacid generator (PAG) has been developed. This resist consisting of PPE (73 wt %), MBMP (20 wt %) and DIAS (7 wt %) showed a high sensitivity (D0.5) of 58 mJ/cm2 and a contrast (γ0.5) of 9.5 when it was exposed to i‐line (365 nm wavelength light), postexposure baked at 145 °C for 10 min, and developed with toluene at 25 °C. A fine negative image featuring 6 μm line‐and‐space pattern was obtained on the film exposed to 300 mJ/cm2 of i‐line by a contact‐printed mode. The resulting polymer film cured at 300 °C for 1 h under nitrogen had a low dielectric constant (ε = 2.46) comparable to that of PPE and a higher Tg than that of PPE. In addition, the cured PSPPE film was pretty low water absorption (<0.05%) as same as PPE. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 4949–4958, 2008

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Negative‐type photosensitive poly(phenylene ether) based on poly(2,6‐dimethyl‐1,4‐phenylene ether), a crosslinker, and a photoacid generator

Mizoguchi¹,

Ueda²

2008

J. Polym. Sci. A Polym. Chem.

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“…This eletrophilic substitution reaction is novel to the best of our knowledge, although the similar reaction based on arylene compounds has been reported. 12 High-resolution patterns of CPs are expected from this approach.…”

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confidence: 99%

A Negative-Type Photosensitive Poly(3-hexylthiophene) with Cross-Linker and Photoacid Generator

et al. 2009

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“…10 These findings prompted us to develop a PSTSP based on a common matrix such as commercially available engineering plastics, a crosslinker, and a PAG, which will provide a versatile, promising, straightforward route for the formation of PSTSP without a high thermal treatment. This paper presents development of a negative-type chemically amplified PSPEES consisting of PEES, a cross-linker MBMP having good compatibility with PEES and DIAS as a PAG.…”

mentioning

confidence: 99%

Direct Patterning of Poly(ether ether sulfone) Using a Cross-linker and a Photoacid Generator

Mizoguchi

Ueda

2008

Polym J

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A negative-type photosensitive poly(ether ether sulfone) (PSPEES) based on a commercially available engineering plastic poly (oxybiphenyl-4,4 0 -diyloxy-1,4-phenylenesulfonyl-1,4-phenylene) (PEES), a cross-linker 4,4 0 -methylenebis[2,6-bis(methoxymethyl)phenol] (MBMP) having good compatibility with PEES, and diphenylidonium 9,10-dimethoxyanthracene-2-sulfonate (DIAS) as a photoacid generator (PAG) has been developed. The resist consisting of PEES (85 wt %), MBMP (10 wt %) and DIAS (5 wt %) showed a high sensitivity (D 0:5 ) of 21 mJ/cm 2 and a contrast ( 0:5 ) of 2.1 when it was exposed to i-line (365 nm wavelength light), post-exposure baked (PEB) at 170 C for 3 min, and developed with N,Ndimethylacetamide (DMAc) at room temperature. A fine negative-image featuring 4 mm line-and-space pattern was obtained on the film. Thus, this photolithographic system has a highly potential to be utilized in the industry for next generation, because most of engineering plastics having aromatic ring are available as matrix polymers, and this process is not necessary high thermal curing treatment after development.KEY WORDS: Photosensitive Polymer / Photoacid Generator / Poly(ether ether sulfone) / Cross-linker / High-performance engineering plastics such as polyimides (PIs), polybenzoxazoles (PBOs), poly(ether ether sulfone)s (PEESs), poly(phenylene ether)s (PPEs), and poly(ether ether keton)s (PEEKs) are continuously receiving considerable attention for their potential application in automobile, electronics, optical devices and related markets. Particularly, photosensitive polyimides (PSPIs) and polybenzoxazoles (PSPBOs) are widely used as stress buffer and insulation layers of multichip package in micro-electronics field, because they possess excellent thermal stability and mechanical properties, and reasonably low dielectric constant.1-3 As PIs and PBOs are generally not soluble in organic solvents, poly(amic acid)s (PAAs) and poly(o-hydroxy amide)s are used as PI and PBO precursors, respectively, and require an extremely high temperature about 350 C to convert into corresponding PIs and PBOs. This high-temperature process is not applicable to electronic applications because the thickness of silicon wafers is less than 100 mm, and thus the less thermal stress is required. Therefore, we have reported a series of low temperature cyclization methods for PSPIs and PSPBOs to produce more useful applications in the micro-electronics industry. [3][4][5][6][7] It is also important to develop a photosensitive and thermally stable polymer (PSTSP) which does not require high thermal curing treatment.In previous papers, we reported a negative-type PSPI based on PAA, a cross-linker 4,4 0 -methylenebis[2,6-bis(hydroxylmethyl)]phenol (MBHP), and (5-propylsulfonyl oxyimino-5H-thiophene-2-ylidene)-2-(methylphenyl)acetonitrile (PTMA) as a PAG.8,9 A negative-type photosensitive polymer based on poly(naphthylene ether), PTMA, and hexa(methoxymethyl)-melamine as a cross-linker was also reported. 10 These findings prompted us to develop a PST...

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A Negative Type Photosensitive Polymer Based on Poly(naphthylene ether), a Cross-Linker, and a Photoacid Generator with Low Dielectric Constant

Cited by 10 publications

References 17 publications

Negative‐type photosensitive poly(phenylene ether) based on poly(2,6‐dimethyl‐1,4‐phenylene ether), a crosslinker, and a photoacid generator

Negative‐type photosensitive poly(phenylene ether) based on poly(2,6‐dimethyl‐1,4‐phenylene ether), a crosslinker, and a photoacid generator

A Negative-Type Photosensitive Poly(3-hexylthiophene) with Cross-Linker and Photoacid Generator

Direct Patterning of Poly(ether ether sulfone) Using a Cross-linker and a Photoacid Generator

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