Innovation via Photosensitive Polyimide and Poly(benzoxazole) Precursors-a Review by Inventor

Rubner, Roland

doi:10.2494/photopolymer.17.685

Cited by 26 publications

(20 citation statements)

References 2 publications

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“…To obviate such complex procedures, DNQ, which functions as a dissolution inhibitor, is added to the PHA solution to form a photosensitive polymer solution (Scheme 1) in a typical formulation of PSPBO first developed by R. Rubner. [7][8][9] The use of PSPBOs allows simple and safe fabrication of electronic devices owing to the elimination of additional photoresist.…”

Section: Typical Preparation Of a Pspbo Systemmentioning

confidence: 99%

Recent Development of Photosensitive Polybenzoxazoles

Fukukawa

Ueda

2006

Polym J

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ABSTRACT:Photosensitive polybenzoxazoles (PSPBOs) have been attracting great attention as insulating materials in microelectronic industry, and can be directly patterned to simplify processing steps. This article reviews recent works on development of PSPBOs. After brief introduction, a typical formulation method of PSPBOs was described, followed by a facile synthetic method of a precursor of PBOs, highly sensitive PSPBOs, highly transparent poly(ohydroxy amide)s (PHAs), an efficient catalyst for low-temperature cyclization of PHA, and finally other applications of PSPBOs.

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Section: Typical Preparation Of a Pspbo Systemmentioning

confidence: 99%

Recent Development of Photosensitive Polybenzoxazoles

Fukukawa

Ueda

2006

Polym J

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“…Indeed, a few 2.38 wt% aqueous tetramethylammonium hydroxide TMAHaq.-developable positive-type PSPIs have been reported [10][11][12], in which highly fluorinated or partially esterified PAAs are used to reduce the dissolution rate in TMAHaq. On the other hand, PSPBOs based on poly(o-hydroxy amide) (PHA) derived from 4,4'-(hexafluoroisopropylidene)bis(o-aminophenol) (6FAP) and 4,4'-oxybis(benzoic acid) derivatives with a photosensitive compound are widely used [4,5,7]. PSPBO has been developed to significantly simplify the processes because phenolic hydroxyl groups in PHA, a precursor polymer of PBO, provide an adequate solubility in an aqueous alkaline developer.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, they simplify processing and avoid the use of photoresists in the microelectric industry [1][2][3][4][5][6]. The commercially available PSPIs usually consist of poly(amic acid) (PAA) derivatives with methacryloyl pendant groups as cross-linking sites [7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Development of Thermally Stable and Photosensitive Polymers

Higashihara

Shibasaki

Ueda

2012

J. Photopol. Sci. Technol.

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Photosensitive polyimides (PSPIs) and photosensitive polybenzoxazoles (PSPBOs) have been used in the semiconductor industry as interlevel insulators, buffer coat materials, α-ray shielding layers, etc., because of their excellent thermal stabilities, good mechanical properties, and relatively low dielectric constants. These thermally stable and photosenstive polymers (TSPSPs) are also expected to improve their performance with the increased developments in the semiconductor industry. In this short review, we describe several TSPSPs that were recently developed by our groups. These TSPSPs have several advantages compared to conventional PSPIs and PSPBOs, such as a simple formulation of the resists, an environmentally-friendly fabrication and patterning process, high sensitivity, low-temperature cyclization, low dielectric constant, low CTE, etc.

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“…[3][4][5][6][7][8][9][10][11][12] The commercially available PSPBO is based on poly(o-hydroxy amide) (PHA), which is usually prepared by polycondensation of 4,4 0 -(hexafluoroisopropylidene)bis(o-aminophenol) (12) and 4,4 0 -oxybis-(benzoic acid) (8a) using a condensation agent, because of its high transparency at 365 nm wavelength (i-line). 13,14 There is an increasing demand for thicker films for small package to act as a buffer layer andray shielding applications, 15,16 consequently, it is quite important to develop a novel photosensitive polymer with higher transparency for UV lithography. The absorption of PI and PBO in i-line region corresponds to the excitation of electrons such as transitions involving p, s, and n electrons, charge-transfer (CT) electrons, and d and f electrons.…”

mentioning

confidence: 99%

Highly Transparent Photosensitive Polybenzoxazole: Poly(o-hydroxy amide) Derived from 4,4′-(Hexafluoroisopropylidene)bis(o-aminophenol) and o-Substituted Dicarboxylic Acid Chlorides

Shibasaki

Toyokawa

Ando

et al. 2006

Polym J

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ABSTRACT:A novel poly(o-hydroxyamide) (PHA) as a precursor of photosensitive polybenzoxazole (PSPBO) that exhibits high transparency at 365 nm wavelength (i-line) has been developed. Time-dependent density functional theory (TD-DFT) calculations using the B3LYP hybrid functional were performed to predict the transparencies of various o-hydroxyamides in the i-line region. Based on these results, 2,2 0 -dimethyl-biphenyl-3,3 0 -dicarboxylic acid chloride was prepared and polymerized with 4,4 0 -(hexafluoroisopropylidene)bis(o-aminophenol). The resulting PHA-3 showed a high transparency (92%, 1:0 Â 10 À3 mol/L in N,N-dimethylacetamide (DMAc)), superior to that of the conventional PHA-1 (83% at the same concentration in DMAc) derived from 4, The thermal and dielectric characteristics of photosensitive polyimide (PSPI) are acceptable for a number of applications in the semiconductor industry, and a wide variety of PSPI has been developed and are made commercially available to meet requirements of different applications, such as inter-level insulation, stress buffer layer, and -ray shielding layers of semiconductor devices.1 PI, however, has numerous imide groups that increase water uptake and dielectric constant.2 Polybenzoxazole (PBO) is known as an super engineering thermoplastics, and its properties are comparable with PI. In addition, the absence of carbonyl group in PBO results in lower water uptake and dielectric constant.2 Thus, the photosensitive polybenzoxazole (PSPBO) is attracting great attention as substitute for conventional PSPI in recent years. 3-12The commercially available PSPBO is based on poly(o-hydroxy amide) (PHA), which is usually prepared by polycondensation of 4,4 0 -(hexafluoroisopropylidene)bis(o-aminophenol) (12) and 4,4 0 -oxybis-(benzoic acid) (8a) using a condensation agent, because of its high transparency at 365 nm wavelength (i-line). 13,14 There is an increasing demand for thicker films for small package to act as a buffer layer andray shielding applications, 15,16 consequently, it is quite important to develop a novel photosensitive polymer with higher transparency for UV lithography. The absorption of PI and PBO in i-line region corresponds to the excitation of electrons such as transitions involving p, s, and n electrons, charge-transfer (CT) electrons, and d and f electrons. Recently, we have demonstrated that the time-dependent density functional theory (TD-DFT) calculations using the B3LYP hybrid functional with the 6-311++G(d,p) basis set can well reproduce UV spectra in the measurements of model compounds without incorporation of empirical corrections.17 Utilizing this method, the absorption in i-line region of the above mentioned PHA was found to be the CT type transition between the benzoic acid and the o-hydroxyamide rings. Therefore, we designed and prepared a novel transparent PSPBO based on 4,4 0 -sulfonylbis(o-aminophenol) (13) and 4,4 0 -oxybis(benzoyl chloride) (8b) for i-line lithography.18 Introduction of a sulfone group as a substitute for hexafluoroisopropylidene...

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Innovation via Photosensitive Polyimide and Poly(benzoxazole) Precursors-a Review by Inventor

Cited by 26 publications

References 2 publications

Recent Development of Photosensitive Polybenzoxazoles

Recent Development of Photosensitive Polybenzoxazoles

Development of Thermally Stable and Photosensitive Polymers

Highly Transparent Photosensitive Polybenzoxazole: Poly(o-hydroxy amide) Derived from 4,4′-(Hexafluoroisopropylidene)bis(o-aminophenol) and o-Substituted Dicarboxylic Acid Chlorides

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