2007 Fiscal Year Final Research Report Summary
Development of Photosensitive Polybenzoxazole for Next Generation Protecting Layer
| Project/Area Number |
18350059
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Polymer chemistry
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
UEDA Mitsuru Tokyo Institute of Technology, Dept. of Organic&Polymeric Materials, Professor (20007199)
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| Co-Investigator(Kenkyū-buntansha) |
SHIBASAKI Yuji Iwate University, Dept. Applied Chemistry, Associate Professor (90323790)
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| Project Period (FY) |
2006 – 2007
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| Keywords | Photosensitive polymer / Polybenzoxazole / Photoacid genrator / Chemical Amplification / Dissolution inhibitor / Direct esterification / Thermal acid generator / Low temperature cyclization |
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| Research Abstract |
1. We developed the facile synthesis of active p-nitropheny diester from aromatic dicarboxylic acid and p-nitrophenol catalyzed by p-toluenesulfonic acid, and poly(o-hydroxy amide) PHA with high molecular weights could be obtained by polycondensation of active diester and bis(o-aminophenol). This process will provide a potentially efficient and versatile route for the synthesis of PHA.
2. We developed a positive-type photosensitive polybenzoxazole (PSPBO) based on a poly(o-hydroxy amide) (PHA), dissolution inhibitor (DI), 9,9-bis(4-tert-butoxycarbonyloxyphenyl)fluorene (t-BocBHF), and the photoacid generator (PAG) (5-propylsulfonyloxyimino-5H-thiophene-2-ylidene) -(2-methylphenyl)acetonitrile (PTMA). The t-BocBHF was easily prepared by reaction of 9,9-bis(4-hydroxyphenyl)fluorene with di-tert-butyl dicarbonate. The dissolution behavior of this PSPBO system was studied in relation to PTMA and t-BocBHF loadings, and post exposure baking (PEB) temperature. The PSPBO consisting of PHA (77 w
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t%), t-BocBHF (20 wt%), and PTMA (3 wt%) exhibited a sensitivity of 34 mJ/cm2 and contrast of 5.8 when exposed to 365-nm light (i-line) and developed with the aqueous alkaline developer, 2.38 wt% tetramethylammonium hydroxide solution (TMAHaq) / 5 wt% iso-propanol (iPrOH). A clear positive image with 8-pm features was produced by contact-printing and converted into the poly(benzoxazole) pattern upon heating at 3500C for 1 h.
3. We developed 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/cm2 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 (/PrOH). A clear positive image with 3-pm features was produced by contact-printing and converted into a poly(benzoxazole) (PBO) pattern upon heating at 250 ℃ 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. Less
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[Journal Article] Photosensitive Poly(benzoxazole) Based on Poly(o-hydroxy amide), Dissolution Inhibitor, Thermoacid Generator, and Photoacid Generator2007
Author(s)
T., Ogura, K., Yamaguchi, Y., Shibasaki, M., Ueda
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Journal Title
Polym. J 39
Pages: 245-251
Description
「研究成果報告書概要(欧文)」より
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[Presentation] A Negative-type Photosensitive Polymer Based on Poly(2,6-dimethyl -1,4-phenylene Ether), a Cross-linker and a Photoacid Generator2007
Author(s)
K., Mizoguchi, K., Tsuchiya, Y., Shibasaki, M., Ueda
Organizer
23th International Conference of Photopolymer Science and Technology
Year and Date
2007-06-28
Description
「研究成果報告書概要(欧文)」より
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