Radiation imagery chemistry: process – composition – or product th – Diazo reproduction – process – composition – or product – Composition or product which contains radiation sensitive...
Patent
1999-04-02
2000-09-19
Chu, John S.
Radiation imagery chemistry: process, composition, or product th
Diazo reproduction, process, composition, or product
Composition or product which contains radiation sensitive...
430192, 430193, 534557, 568720, G03F 7023
Patent
active
061209694
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a novel polyphenol compound, a quinonediazide ester thereof and positive photoresist compositions using the same. It also relates to positive photoresist compositions excellent in sensitivity, definition, exposure margin, focal depth range properties and sectional shape. In particular, the compositions have a large exposure margin and hence are advantageous in the formation of fine patterns of half a micron or narrower.
BACKGROUND ART
Positive photoresist compositions comprising an alkali soluble resin and a quinonediazide ester are excellent in definition, sensitivity and etching resistance and hence have been satisfactorily used for the production of semiconductor devices and liquid crystal devices.
In the current manufacture of ultralarge-scale integrated circuit (ultra LSI), a high definition of not more than half a micron, for example, of 0.4 .mu.m, 0.35 .mu.m or the like is required. In addition, there are demands on photoresist compositions which can form a resist pattern satisfactory in definition, exposure margin, focal depth range properties and having a good sectional shape.
It is, however, difficult to form a resist pattern having an excellent sectional shape in the formation of a fine pattern of half a micron or thinner. With a pattern becoming finer, the rate of change of the pattern shape due to exposure change increases (i.e., the exposure margin is small), and thus, a little difference in exposure conditions invites a large difference in pattern shape. Therefore, the exposure with the use of any of conventional photoresist compositions must be controlled within a very narrow range in order to obtain a good pattern shape of the exact size of a mask pattern.
It is, therefore, an object of the present invention to provide a positive photoresist composition having a high definition, a high sensitivity and a large exposure margin, and to provide a novel polyphenol compound and a quinonediazide ester thereof which can be constituents of the composition.
DISCLOSURE OF INVENTION
After intensive investigations, the present inventors found that the above object can be achieved by using a specific quinonediazide ester as a photosensitizer, or by using a specific polyphenol compound as a sensitizer (sense amplifier). The invention has been accomplished based on the above finding.
To be more specific, the present invention provides a polyphenol compound represented by the following formula (I): ##STR1##
The present invention provides a quinonediazide ester represented by the following formula (II): ##STR2## (wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently a hydrogen atom or a naphthoquinone-1,2-diazidesulfonyl group, and wherein at least one is a naphthoquinone-1,2-diazidesulfonyl group).
The present invention also provides the aforementioned quinonediazide ester, in which at least two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are naphthoquinone-1,2-diazidesulfonyl groups.
The present invention further provides a positive photoresist composition containing (A) an alkali-soluble resin and (B) a photosensitizer, in which the photosensitizer is the aforementioned quinonediazide ester.
Further, the invention provides a positive photoresist composition containing (A) an alkali-soluble resin, (B) a photosensitizer and (C) a sensitizer, in which the sensitizer is the aforementioned polyphenol compound.
Incidentally, photoresist compositions respectively using any of photosensitizers specifically described in Japanese Patent Laid-Open Nos. 6-167805, 7-159990, 7-219220 and 8-339079 or a photosensitizer described in Japanese Patent Laid-Open No. 8-245461 are insufficient in the improvement of exposure margin.
BRIEF DESCRIPTION OF DRAWINGS
FIG. 1 is a diagram illustrating the results of mass spectrometry of crystals of bis(2,5-dimethyl-3-(2-hydroxy-5-ethylbenzyl)-4-hydroxyphenyl)methane prepared in Synthetic Example 1.
FIG. 2 is a diagram illustrating the results of .sup.1 H-NMR analysis of crystals of bis(2,5-dimethyl-3-(2-hydroxy-5-ethylb
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Doi Kousuke
Hagihara Mitsuo
Kohara Hidekatsu
Nakajima Tetsuya
Nakayama Toshimasa
Chu John S.
Tokyo Ohka Kogyo Co. Ltd.
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