Photopatternable insulating materials

Ahne, Hellmut; Rubner, Roland; Sezi, Recai

doi:10.1016/s0169-4332(96)00383-2

Cited by 23 publications

(15 citation statements)

References 5 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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“…Recently, photosensitive poly(benzoxazole)s (PBOs) have been attracting great attention as photosensitive and thermally stable polymers because of their high mechanical strength, thermal stability, and low dielectric constants with respect to PSPIs 5–13…”

Section: Introductionmentioning

confidence: 99%

New synthetic route for photosensitive poly(benzoxazole)

Ebara

Shibasaki

Ueda

2002

J. Polym. Sci. A Polym. Chem.

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A new positive working photosensitive poly(benzoxazole) (PBO) precursor based on poly(o‐hydroxyazomethine) (3) and 1‐{1,1‐bis[4‐(2‐diazo‐1‐(2H)naphthalenone‐5‐sulfonyloxy)phenyl]ethyl}‐4‐{1‐[4‐(2‐diazo‐1(2H)naphthalenone‐5‐sulfonyloxy)phenyl]methylethyl}benzene (S‐DNQ) as a photosensitive compound was developed. 3 was prepared by the condensation of 2,2‐bis(3‐amino‐4‐hydroxyphenyl)hexafluoropropane with isophthalaldehyde in 1‐methyl‐2‐pyrrolidinone/toluene under azeotropic conditions. The photosensitive PBO precursor containing 30 wt % S‐DNQ showed a sensitivity of 120 mJ cm−2 and a contrast of 2.2 when it was exposed to 436‐nm light and developed with a 2.38 wt % aqueous tetramethylammonium hydroxide solution at room temperature. A fine positive image featuring 10‐μm line and space patterns was observed on the film of the photoresist exposed to 200 mJ cm−2 ultraviolet light at 436 nm by the contact mode. The positive image was successfully converted into the PBO pattern by a thermal treatment. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 3399–3405, 2002

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“…Photosensitive polybenzoxazoles (PSPBOs) [1][2][3][4][5] are used as buffer coatings to protect bare chips from stresses induced by fillers or thermal mismatches between a passivation layer and molding materials. These compounds possess high mechanical strength, thermal stability, and low dielectric constants.…”

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confidence: 99%

Photosensitive Poly(benzoxazole) Based on Poly(o-hydroxy amide), Dissolution Inhibitor, Thermoacid Generator, and Photoacid Generator

Ogura

Yamaguchi

Shibasaki

et al. 2007

Polym J

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ABSTRACT:A positive-type photosensitive polybenzoxazole (PSPBO) based on a poly(o-hydroxy amide) (PHA), a dissolution inhibitor (DI) 9,9-bis(4-tert-butoxycarbonyloxyphenyl)fluorene (t-BocBHF), a thermoacid generator (TAG) isopropyl p-toluenesufonate (ITS), and a photoacid generator (PAG) (5-propylsulfonyloxyimino-5H-thiophene-2-ylidene)-(2-methylphenyl)acetonitrile (PTMA) has been developed. ITS was easily prepared by reaction of p-toluenesulfonyl chloride with isopropyl alcohol. The dissolution behavior of the PSPBO system was studied in relation to PTMA loadings, and post exposure baking (PEB) temperature and time. The PSPBO consisting of PHA (73 wt %), t-BocBHF (18 wt %), ITS (7.5 wt %), and PTMA (1.5 wt %) exhibited a sensitivity of 33 mJ/cm 2 and a contrast of 5.1 when exposed to 365 nm light (i-line) and developed with an aqueous alkaline developer, 2.38 wt % tetramethylammonium hydroxide solution (TMAHaq)/2.5 wt % iso-propanol (i-PrOH). A clear positive image with 3 mm features was produced by contact-printing and converted into a poly(benzoxazole) (PBO) pattern upon heating at 250 C for 20 min. Thus, the ITS is effective as a TAG for improving the sensitivity and low temperature cyclization of PHA into the PBO as well to meet practical requirement in the industry. 1-5 are used as buffer coatings to protect bare chips from stresses induced by fillers or thermal mismatches between a passivation layer and molding materials. These compounds possess high mechanical strength, thermal stability, and low dielectric constants. They have been developed to simplify processes in which a precursor of polybenzoxazoles (PBOs), poly(o-hydroxy amide) (PHA), is used as a polymer matrix. The phenolic hydroxyl groups in PHA promote solubility of 2.38 wt % tetramethylammonium hydroxide solution (TMAHaq), used as the aqueous alkaline developer. Previously, PHA obtained from 4,4 0 -(hexafluoroisopropylidene)bis(o-aminophenol) (6FAP) and 4,4 0 -oxybis(benzoic acid) derivatives was used because of its high transparency at a wavelength of 365 nm (i-line). A conventional PSPBO was formulated by adding the photo-sensitizer diazonaphthoquinone (DNQ) to PHA. The sensitivity of photopolymers is important in the design of photoresist materials. The conventional PSPBO based on DNQ, however, possesses low sensitivity (>100 mJ/cm 2 ) and a strong absorbance at 365 nm, and is difficult to use for thick patterns. To overcome these problems, a chemically amplified technique was introduced to develop PSPBOs coupled with a photoacid generator (PAG), 7 for which 9,9-bis(4-tert-butoxycarbonyloxyphenyl)fluorene (tBocBHF) was used as a dissolution inhibitor (DI). 8This three-component, positive-type, alkaline-developable PSPBO showed the sensitivity and contrast of 34 mJ/cm 2 and 5.8, respectively with i-line exposure, to produce a 20 mm image in 10 mm thick film. A positive image of PHA is converted into that of PBO by thermal treatment at 350 C. This high-temperature process is not applicable to conventional electronic applications containing on...

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Photopatternable insulating materials

Cited by 23 publications

References 5 publications

Recent Development of Photosensitive Polybenzoxazoles

Recent Development of Photosensitive Polybenzoxazoles

New synthetic route for photosensitive poly(benzoxazole)

Photosensitive Poly(benzoxazole) Based on Poly(o-hydroxy amide), Dissolution Inhibitor, Thermoacid Generator, and Photoacid Generator

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