Preparations and properties of novel positive photosensitive polyimides

Rumiko Horiguchi Hayase; Naoko Kihara; Naohiko Oyasato; S. Matake; Masayuki Oba

doi:10.1117/12.46392

1 June 1991 Preparations and properties of novel positive photosensitive polyimides

Rumiko Horiguchi Hayase, Naoko Kihara, Naohiko Oyasato, S. Matake, Masayuki Oba

Proceedings Volume 1466, Advances in Resist Technology and Processing VIII; (1991) https://doi.org/10.1117/12.46392
Event: Microlithography, 1991, San Jose, CA, United States

Abstract

Polyamic acid esters with phenol moieties (Ph-ES) were synthesized from diamines and dicarboxylic acids bonding to phenol moieties through ester linkage. To synthesize the dicarboxylic acids, 1 mol of BTDA was reacted with 2 mol of m-hydroxybenzyl alcohol in NMP. The resultant dicarboxylic acid are predominantly benzyl esters, not phenyl esters, was condensed with ODA, using DCC as condensing agent. The polyimide precursors Ph-ES was actually soluble in basic aqueous solutions. However, its dissolution rate was too low for binder resins used for resists. To increase the resist dissolution rate, polyamic acid PA, which is assumed to be more soluble in the base developer, was added to Ph-ES. The PA was synthesized from BTDA and ODA. Resists containing Ph-ES (60 wt%), PA (20 wt%) and naphthoquinone diazide (20 wt%) gave 4 micron line and space pattern with 5 micron thickness. There was no pattern deformation, even after the polyamic acid ester was heated at 320 degree(s)C to form the polyimides. The PA content was critical to the high resolution achievement. As the content of the PA to Ph-ES increases, the pattern shape of the resist deteriorated rapidly. At more than 40 wt% PA rate, patterns could not be obtained, because fine patterns peeled off form the silicon wafer substrate during the development. This proved that adjusting dissolution rates in basic aqueous solutions is one of the significant points for realizing fine resist patterns.

Citation Download Citation

Rumiko Horiguchi Hayase, Naoko Kihara, Naohiko Oyasato, S. Matake, and Masayuki Oba "Preparations and properties of novel positive photosensitive polyimides", Proc. SPIE 1466, Advances in Resist Technology and Processing VIII, (1 June 1991); https://doi.org/10.1117/12.46392

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