High-Contrast Chemically Amplified Photodefinable Poly(benzoxazole) Using Dissolution Reversers

Minegishi, Tomonori; Takusari, Hisanori; Katoh, Kohji

doi:10.2494/photopolymer.17.247

Cited by 8 publications

(3 citation statements)

References 16 publications

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“…For this method, t ‐Boc groups must be introduced into PHA through polymer reactions; that is, two extra steps, such as the modification of PHA with di‐ tert ‐butyl dicarbonate and the isolation of t ‐Boc PHA, are required, and they are tedious. Recently, Minegishi et al18 reported a more convenient method that is widely applicable and provides an easy resist formulation involving a three‐component system consisting of PHA, a PAG, and a dissolution reverser based on acid‐labile esters. However, the dissolution contrast (DC) to 2.38 wt % TMAHaq between the exposed and unexposed areas is nearly 10; a high DC is required to obtain a fine pattern.…”

Section: Introductionmentioning

confidence: 99%

Photosensitive polybenzoxazole based on a poly(o‐hydroxy amide), a dissolution inhibitor, and a photoacid generator

Ogura

Ueda

2007

J. Polym. Sci. A Polym. Chem.

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A positive-type photosensitive polybenzoxazole (PSPBO), based on a poly (o-hydroxy amide) (PHA), the dissolution inhibitor (DI) 9,9-bis(4-tert-butoxycarbonyloxyphenyl)fluorene (t-Boc BHF), and the photoacid generator (5-propylsulfonyloxyimino-5H-thiophene-2-ylidene)-(2-methylphenyl)acetonitrile (PTMA), was developed. Several new tert-butoxycarbonylated compounds as DIs for PSPBOs were prepared from phenolic compounds having a cardolike structure with di-tert-butyl dicarbonate in the presence of 4-dimethylaminopyridine. Among them, t-Boc BHF and 5,5 0 ,6,6 0 -tetra(tert-butoxycarbonyl)-3,3,3 0 ,3 0 -tetramethyl-1,1 0 -spirobiindane acted as excellent DIs, giving a large dissolution contrast between the exposed and unexposed areas in a 2.38 wt % tetramethylammonium hydroxide solution (TMAHaq)/5 wt % iso-propanol (i-PrOH). The dissolution behavior of this PSPBO system was studied in relation to the PTMA and t-Boc BHF loadings and postexposure baking temperature. A PSPBO consisting of PHA (77 wt %), t-Boc BHF (20 wt %), and PTMA (3 wt %) exhibited a sensitivity of 34 mJ/cm 2 and a contrast of 5.8 when exposed to 365-nm light (i-line) and developed with an aqueous alkaline developer, 2.38 wt % TMAHaq/5 wt % i-PrOH. A clear, positive image with 6-lm features and a 10-lmthick pattern with high sensitivity and contrast was produced by contact printing and converted into polybenzoxazole patterns upon heating at 350 8C for 1 h. a The temperature was determined at a heating rate of 5 8C min À1 under nitrogen.

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Section: Introductionmentioning

confidence: 99%

Photosensitive polybenzoxazole based on a poly(o‐hydroxy amide), a dissolution inhibitor, and a photoacid generator

Ogura

Ueda

2007

J. Polym. Sci. A Polym. Chem.

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“…24 A three-component positive-type PSPBO system consisting of PHA, PAG, and an acid-labile dissolution reverser has been developed (Figure 8), where the dissolution reverser acted as a dissolution inhibitor to 2.38 wt % TMAHaq before photo-irradiation, and a dissolution promoter after photo-irradiation. 25 A negative-type chemically amplified PSPBO has also been reported, 26 which was based on PHA capped with norbornene imide (PHA-NI), 4,4 0 -methylenebis-[2,6-di(hydroxymethyl)]phenol (MBHP) as a crosslinker, [27][28][29] and (5-propylsulfonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)acetonitrile (PTMA) as a PAG 30 (Scheme 6). PHA-NI was easily prepared as described above except using 5-norbornene-endo-2,3-dicarboxylic anhydride as an end-capping agent.…”

Section: Development Of Extremely Sensitive Pspbo Resistmentioning

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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“…In the meantime, there were some studies on adding low molecular lipophilic compounds to conventional twocomponent CA photoresists [13][14][15][16]. This new photoresist is called the three-component CA photoresist.…”

Section: Introductionmentioning

confidence: 99%

Dissolution Promotion Effect of Addition of Low Molecular Compounds to Positive Tone Chemically Amplified Photoresist System

Kazuma

Nishiyama

Sato

et al. 2017

J. Photopol. Sci. Technol.

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Three-component chemically amplified photoresists which are consisted of a base resin, a photo acid generator and a dissolution inhibitor are promising because the high sensitivity and the high resolution can be satisfied at the same time. We studied about the dissolution promotion effect of hydroquinone (HQ) in the exposed area. HQ is a model compound of the photo induced product of the dissolution inhibitor. We disclosed that HQ depressed a glass transition temperature (T g ) of the base resin and the sensitivity was improved by enhancing the dissolution rate in the exposed area. It is expected that the dissolution rate was promoted when the post exposure bake temperature exceeded T g because the acid diffuse more easily.

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High-Contrast Chemically Amplified Photodefinable Poly(benzoxazole) Using Dissolution Reversers

Cited by 8 publications

References 16 publications

Photosensitive polybenzoxazole based on a poly(o‐hydroxy amide), a dissolution inhibitor, and a photoacid generator

Photosensitive polybenzoxazole based on a poly(o‐hydroxy amide), a dissolution inhibitor, and a photoacid generator

Recent Development of Photosensitive Polybenzoxazoles

Dissolution Promotion Effect of Addition of Low Molecular Compounds to Positive Tone Chemically Amplified Photoresist System

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