Radiation imagery chemistry: process – composition – or product th – Imaging affecting physical property of radiation sensitive... – Radiation sensitive composition or product or process of making
Reexamination Certificate
1999-04-14
2001-03-27
Chu, John S. (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Imaging affecting physical property of radiation sensitive...
Radiation sensitive composition or product or process of making
C430S905000, C430S910000
Reexamination Certificate
active
06207343
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a positive photosensitive composition for use in the production of semiconductor integrated circuit element, mask for the production of integrated circuit, printed-wiring board, liquid crystal panel, etc.
BACKGROUND OF THE INVENTION
As a positive photosensitive composition there is disclosed chemically-sensitized positive resist compositions in U.S. Pat. No. 4,491,628 and EP 29,139. The chemically-sensitized positive resist composition is a pattern-forming material which, upon irradiation with radiation such as far infrared rays, produces at the exposed area an acid which is then used as a catalyst in the presence of which a reaction is effected to cause change in the solubility of the irradiated area and unirradiated area in a developing solution, thereby forming a pattern on the board.
The foregoing chemically-sensitized positive resist compositions can be roughly divided into three groups, i.e., ternary positive resist composition comprising an alkali-soluble resin composition, a compound which generates an acid upon irradiation with radiation (photo-acid generator) and a compound having an acid-decomposable group for inhibiting dissolution of the alkali-soluble resin, binary positive resist composition comprising a resin having a group which becomes alkali-soluble upon decomposition by the reaction with an acid and a photo-acid generator and hybrid positive resist composition a resin having a group which becomes alkali-soluble upon decomposition by the reaction with an acid, a low molecular dissolution inhibitive compound having an acid-decomposable group and a photo-acid generator.
JP-A-2-19847 (The term “JP-A” as used herein means an “unexamined published Japanese patent application”) discloses a resist composition comprising a resin having the phenolic hydroxyl group in a poly(p-hyroxystyrene) entirely or partially protected by a tetrahydropyranyl group.
Similarly, JP-A-4-219757 discloses a resist composition comprising a resin having the phenolic hydroxyl group in a poly(p-hydroxystyrene) substituted by an acetal group in a proportion of from 20% to 70%.
Further, JP-A-5-249682 discloses a photoresist composition comprising a resin similarly protected by an acetal group. Moreover, JP-A-8-123032 discloses a photoresist composition comprising a ternary polymer containing a group substituted by an acetal group.
Further, JP-A-8-253534 discloses a photoresist composition comprising a partly-crosslinked polymer containing a group substituted by an acetal group.
Further, JP-A-8-15864 discloses a positive resist composition comprising as a resin composition a mixture of a polyhydroxystyrene having its hydroxyl group substituted by t-butoxycarbonyloxy group in a proportion of from 10 to 60 mol % and a polyhydroxystyrene having its hydroxyl group substituted by ethoxyethoxy group in a proportion of from 10 to 60 mol %.
Further, JP-A-9-319092 discloses that a resin comprising an acetal group having an oxy bond incorporated therein exerts an effect of lessening standing wave.
However, these prior art photoresist compositions comprising a resin containing an acid-decomposable group leave something to be desired in rectangularity of pattern profile. In particular, these prior art photoresist compositions are disadvantageous in that the corners of the top of profile are rounded.
Further, these prior art photoresist compositions comprising a resin containing an acid-decomposable group are disadvantageous in that they generate marked standing wave and give a pattern profile stained on the side wall thereof. It has thus been desired to overcome these difficulties.
SUMMARY OF THE INVENTION
It is therefore an object of the present invention to provide a chemically-sensitized positive photosensitive composition excellent in the shape of pattern profile, particularly the regularity of pattern profile, and the reproducibility of lone pattern and having a high resolution.
It is another object of the present invention to provide an excellent chemically-sensitized positive photosensitive composition excellent in the shape of pattern profile, particularly the smoothness in the shape of side wall of pattern, which exhibits a high dry etching resistance, a high sensitivity and a high resolution and generates no standing wave.
These and other objects of the present invention will become more apparent from the following detailed description and examples.
The inventors made extensive studies of the foregoing difficulties. As a result, it was found that the use of a first positive photosensitive composition comprising a compound containing an acid-decomposable group having a specific structure makes it possible to accomplish the foregoing former object of the present invention. The present invention has thus been worked out.
The first positive photosensitive composition according to the present invention has the following constitutions:
(1) A positive photosensitive composition, comprising:
(a) a compound having a group represented by the following general formula (Ia) which decomposes by the action of an acid to enhance its solubility in an alkaline developing solution; and
(b) a compound which generates an acid upon irradiation with actinic rays or radiation:
wherein R
1a
and R
2a
may be the same or different and each represent a hydrogen atom or a C
1-4
alkyl group; W
a
represents a single bond or a divalent organic group; and R
3a
represents a group which decomposes the action of an acid.
(2) The positive photosensitive composition according to Clause (1), wherein said component (a) is a resin having a group represented by the general formula (Ia) which decomposes by the action of an acid to enhance its solubility in an alkaline developing solution.
(3) The positive photosensitive composition according to Clause (1) or (2), further comprising a resin which is insoluble in water but soluble in an alkaline aqueous solution.
Further, the use of the following second positive photosensitive composition makes it possible to accomplish the foregoing latter object of the present invention. Thus, the present invention has been worked out.
The second positive photosensitive composition according to the present invention has the following constitutions:
(4) A positive photosensitive composition, comprising:
(a) a resin having a group represented by the following general formula (Ib) which decomposes by the action of an acid to enhance its solubility in an alkaline developing solution; and
(b) a compound which generates an acid upon irradiation with actinic rays or radiation:
wherein R
1b
and R
2b
may be the same or different and each represent a hydrogen atom or a C
1-4
alkyl group; W
b
represents a divalent organic group; and R
3b
represents a C
11-20
chain alkyl group which may have substituents, a C
11-20
cyclic alkyl group which may have substituents, a C
11-30
aryl group which may have substituents or a C
12-30
aralkyl group which may have substituents.
(5) The positive photosensitive composition according to Clause (4), wherein R
b
and R
2b
may be the same or different and each represent a hydrogen atom or a C
1-4
alkyl group; W
b
represents a divalent organic group; and R
3b
represents a C
11-30
aryl group which may have substituents or a C
12-30
aralkyl group which may have substituents.
(6) The positive photosensitive composition according to Clause (4) or (5), further comprising a compound which decomposes by the action of an acid to enhance its solubility in an alkaline developing solution.
DETAILED DESCRIPTION OF THE INVENTION
The present invention will be further described hereinafter.
The compound (a) having a group represented by the foregoing general formula (Ia) which decomposes by the action of an acid to enhance its solubility in an alkaline developing solution will be further described below.
Examples of the alkyl group represented by R
1a
in the general formula (Ia) include C
1-4
alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group an
Fujimori Toru
Tan Shiro
Chu John S.
Fuji Photo Film Co. , Ltd.
Sughrue Mion Zinn Macpeak & Seas, PLLC
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