Radiation imagery chemistry: process – composition – or product th – Imaging affecting physical property of radiation sensitive... – Radiation sensitive composition or product or process of making
Patent
1995-05-30
1998-02-10
Hamilton, Cynthia
Radiation imagery chemistry: process, composition, or product th
Imaging affecting physical property of radiation sensitive...
Radiation sensitive composition or product or process of making
4302881, 4302801, 522 52, 522 53, 522 59, 546136, 546134, 558 46, 558 47, 552211, 548157, 548169, 548165, G03F 7039, G03F 7038, C07C30963
Patent
active
057167567
DESCRIPTION:
BRIEF SUMMARY
The invention relates to sulfonic acid esters and radiation-sensitive, positive-working or negative-working mixtures prepared therewith and comprising bond (for a positive-working mixture) or a compound having at least two acid-crosslinkable groups (for a negative-working mixture) and in aqueous alkaline solutions.
The invention furthermore relates to radiation-sensitive recording materials which are produced therefrom and which are suitable for the production of photoresists, electronic components and printing plates or for chemical milling.
Radiation-sensitive mixtures containing sulfonic acid esters as acid formers are particularly suitable for exposure to "deep-UV" radiation having a wavelength of 220 to 300 nm, in particular of 248 nm (KrF excimer lasers emit at this wavelength). Sulfonates of substituted phenols (JP-A 03-223 864) or of hydroxymethylbenzoins (DE-A 19 19 678), 2-nitrobenzylsulfonates (EP-A 0 330 386), pyrogallolsulfonates (T. Ueno et al. in "Polymers for Microelectronics--Science and Technology", Ed. Y. Tabata et al., Kodansha-Weinheim-New York, 1989, pages 66-67), N-sulfonyloxyimides (EP-A 0 388 343) or 1-sulfonyloxypyridones (DE-A 41 12 967) have been used to date as sulfonic acid esters. The disadvantages of these compounds are an excessively high intrinsic absorption in the DUV range, insufficient sensitivity (owing to too low a quantum yield in the acid-forming reaction) or insufficient solubility. This leads to deficiencies in the quality of image reproduction, to low throughput speeds of the wafers to be structured or to separation problems.
Many positive-working photoresist layers also contain compounds having acid-clearable groups in addition to the acid-forming aromatic sulfonic acid esters. If such layers are exposed imagewise, it is found that the line width obtained after development is influenced by the storage time between irradiation and heating step (post-exposure bake) and deviations from the original thus occur. The irradiation dose must therefore be adapted to the storage time. This dependence of the image quality on the storage time is a major technical problem which has not been solved to date. It presumably has a plurality of causes. Thus, it is assumed that photolysis products which are unstable and react in an undesirable manner during the storage time are formed from many of the acid-forming compounds used to date. In addition, relatively long storage times frequently lead to the formation of insoluble top layers whose prolonged development times lead to complications with the substantial automation of semiconductor production.
It was therefore the object of the invention to provide a radiation-sensitive mixture which has high sensitivity in particular to DUV radiation and at the same time high resolution down to the region of less than 500 nm. Regardless of the storage time between imagewise exposure and post-exposure bake, it should be simple to process and combine high process stability and processing range with accurate reproducibility and reliability.
The object is achieved by the provision of a radiation-sensitive, positive-working or negative-working mixture comprising bond (for a positive-working mixture) or a compound having at least two acid-crosslinkable groups (for a negative-working mixture) and in aqueous alkaline solutions, unfused or fused (C.sub.6 -C.sub.14)aryl or (C.sub.4 -C.sub.11)heteroaryl radical containing oxygen, sulfur or nitrogen as a heteroatom and in the compounds of the formula II is a divalent or trivalent radical of a mononuclear or polynuclear unfused or fused (C.sub.6 -C.sub.14)aromatic or (C.sub.4 -C.sub.12)heteroaromatic containing oxygen, sulfur or nitrogen as a heteroatom or a divalent radical of the formula --C.sub.6 H.sub.4 13 X--C.sub.6 H.sub.4 --, in which X is an oxygen atom, a carbonyl or sulfonyl group or a group CR.sup.7 R.sup.8, in which R.sup.7 and R.sup.8 are identical or different and are a methyl or trifluoromethyl radical, formula II is a straight-chain or branched, unsubstituted or substituted (C.sub.1 -C.su
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Appel Wolfgang
Herr Walter
Pawlowski Georg
Roeschert Horst
Spiess Walter
Hamilton Cynthia
Herberts GmbH
Hoechst Aktiengesellschaft
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