Preparation of positive photoreactive polyimides and their characterization

Kubota, Shigeru; Moriwaki, T.; Ando, Torahiko; Fukami, Akira

doi:10.1002/app.1987.070330528

Cited by 54 publications

(36 citation statements)

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“…To overcome this problem, the system consisting of PAA having hydrophobic structure and DNQ was investigated (eq. (11,12)). These PSPI precursors have a high sensitivity and good resolution [14].…”

Section: -1 2-nitrobenzylester-typementioning

confidence: 99%

Recent Development in Photosensitive Polyimide (PSPI)

Mochizuki

Ueda

2001

J. Photopol. Sci. Technol.

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Section: -1 2-nitrobenzylester-typementioning

confidence: 99%

Recent Development in Photosensitive Polyimide (PSPI)

Mochizuki

Ueda

2001

J. Photopol. Sci. Technol.

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“…[3] On the other hand, the positive type PSPIs consist of poly (amic acid)s and dissolution inhibitors such as o-diazonaphthoquinone (DNQ), 1,4-dihydropyridine derivatives, [4,5] and o-nitrobenzyl esters of polyamic acid. [6] However, these resist systems require high thermal treatment for the imidization after development, which is not suitable for semiconductor manufacturing. Therefore, positive type alkaline developable PSPIs based on poly (hydroxyimide)s and DNQ have been reported.…”

Section: Introductionmentioning

confidence: 99%

New Positive Type Photosensitive Polyimide: Hyperbranched Poly (Ether imide) with Diazonaphthoquinone

Okazaki

Shibasaki

Ueda

2001

J. Photopol. Sci. Technol.

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A positive working photosensitive polyimide based on hyperbranched poly (ether imide) (H-PEI) and 2,3,4-tris[1-oxo-2-diazonaphthoquinone-5-sulfonyloxy] benzophenone (D5SB) as a photoreactive compound has been developed. H-PEI was prepared by polycondensation of 3,5-di-tert-butyldimethylsilyloxyphenyl-4-fluorophthalimide, followed by deprotection of tert-butyldimethylsilyl group with KF-HBr. The H-PEI has an excellent transparency to UV light. The photosensitive polyimide containing 30 wt% of D5SB showed a sensitivity of 120 mJ•cm 2 and a contrast of 2.8 when it was exposed to 365 nm light followed by developing with a 2.38 % aqueous tetramethylammonium hydroxide (TMAH) solution at room temperature.

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“…9 From the point of polyimide base development, Kubota reported a different posi PSPI by introduction of o-nitirobenzyl group to carboxylic acid in PAA. 10 Omote reported chemical amplification system by mixing with t-butyl protected PAA and photo-acid-generators. 11 Okabe invented the posiPSPI by mixing with phenolic group containing poly(amic ester) and dinaphthoquinone diazide to reduce the dissolution of polyimide precursor.…”

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confidence: 99%

Novel Partial Esterification Reaction in Poly(amic acid) and Its Application for Positive-Tone Photosensitive Polyimide Precursor

2009

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We found novel quantitative esterification in poly(amic acid) (PAA) by reacting with N,N-dimethylformamide dialkyl acetals (DFAs). Different alkyl ester was obtained by changing the alkyl group in DFAs. The esterification ratio was determined by amount of DFAs. The reaction proceeds under mild condition without any catalysis. It has not been reported such a kind of quantitative partial esterification before. The partial esterification allowed us to control the solubility of PAA to alkaline solutions. The strict solubility rate control to alkaline solution of PAA was quite important for positive tone photosensitive polyimide (posi PSPI). The partial esterification of PAA gave us a way to strict dissolution control. By using it, we could obtain posi PSPI just mixing with diazonaphthoquinone compound. Polyimides are widely used for semiconductor applications such as inter-layer dielectrics, protection layers (buffer coatings), and re-distribution layers for wafer level package.1 For these applications, polyimide is required to make a fine pattern by photo-lithographic technique. In early times polyimide was patterned by chemical etching through photo-resist pattern. In order to simplify the polyimide pattering process, several groups developed the addition of photosensitivity to polyimide precursor namely PSPI.2,3 Most of the PSPIs were negative tone type, which made exposed area insoluble by photoreaction. In order to progress semiconductor, polyimide is required fine pattern such as 5 mm or less. To realize such a fine pattern, posi PSPI was desired. First posi PSPI was reported by Loprest et al. 4 The posi PSPI was composed of PAA and naphthoquinone diazide compound which is popular for novolak photo resist system. But it was not realized due to high solubility of PAA to alkaline solution. In order to obtain suitable solubility of PAA, Simmons reported partial protection by reaction with 1,4-dihydropyrane.5 There were few drawbacks for this reaction. One was that the reaction did not proceed quantitatively. Another was that reaction condition needs acidic catalyst. Excess amount of 1,4-dihydropyrane with acidic catalyst and long reaction time were required. Posi PSPI from special PAA structure was reported by Sakayori et al. 6On the other hand, Rubner reported positive tone photosensitive polybenzoxazole precursor.7 Polybenzoxazole precursor was poly(hydroxyamide) which has phenolic groups in the polymer chain. The acidity of phenol group was much weaker than that of aromatic carboxylic acid. The positive tone photosensitive polybenzoxazole precursor was applied for buffer coating of semiconductor devices. 8 Recently Watanabe et al. reported the negative tone photosensitive polybenzoxazole precursor by using acid catalysis cross linking. 9From the point of polyimide base development, Kubota reported a different posi PSPI by introduction of o-nitirobenzyl group to carboxylic acid in PAA.10 Omote reported chemical amplification system by mixing with t-butyl protected PAA and photo-acid-generators.11 Okabe invented...

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Preparation of positive photoreactive polyimides and their characterization

Cited by 54 publications

References 1 publication

Recent Development in Photosensitive Polyimide (PSPI)

Recent Development in Photosensitive Polyimide (PSPI)

New Positive Type Photosensitive Polyimide: Hyperbranched Poly (Ether imide) with Diazonaphthoquinone

Novel Partial Esterification Reaction in Poly(amic acid) and Its Application for Positive-Tone Photosensitive Polyimide Precursor

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