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
1999-10-18
2001-07-24
Baxter, Janet (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
C430S270100, C430S296000, C430S966000, C430S942000, C430S281100
Reexamination Certificate
active
06265135
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a positive-working electron beam or X-ray resist composition, and particularly to a positive-working electron beam or X-ray resist composition excellent in a pattern profile obtained by exposure to an electron beam or X-ray and having a small number of development defects.
BACKGROUND OF THE INVENTION
In i-line resists, KrF excimer laser resists and ArF excimer laser resists, bottom portions of the resists become lower in exposure than exposed surfaces thereof, because the resists have absorption at exposure wavelengths. In the case of positive-working resists, therefore, a pattern profile called a “taper form” is generally formed.
In the case of electron beam resist or X-ray resist, however, incident electron or X-ray has a charge, and interacts with atomic nuclei and electrons of substances constituting the resists, so that the incidence of an electron beam or X-ray into a resist film is necessarily accompanied by scattering. Accordingly, with respect to an exposed area, the bottom portion becomes larger in exposure area than the surface of the resist film. For this reason, the positive-working resist has the problem that a pattern profile called a “reverse taper form” is formed.
Further, even when exposure is carried out with reduced beam diameter for resolving a fine pattern, the scattering widens the exposure area to thereby deteriorate the resolution.
Furthermore, with recent miniaturization of processed patterns, development defects have posed a serious problem, and resists having less development defects have been desired.
Furthermore, the conventional resists have a low sensitivity, which causes a problem of so-called “throughput” in the production of integrated circuits. From this standpoint, a resist having a high sensitivity as compared with the conventional electron beam or X-ray resists has been desired.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a positive-working electron beam or X-ray resist composition which has high resolution, can give a rectangular excellent pattern profile, and is improved in development defects.
According to the present invention, the following positive-working electron beam or X-ray resist composition is provided, and the above-mentioned object of the present invention is attained.
1. A positive-working electron beam resist composition comprising:
(a) a compound capable of generating an acid by irradiation of an electron beam;
(b) a resin containing a group which is decomposable by action of an acid to increase solubility in an alkali developing solution; and
(c) a fluorine and/or silicon surfactant,
the compound capable of generating an acid by irradiation of an electron beam being a compound which generates benzenesulfonic acid, naphthalenesulfonic acid or anthracenesulfonic acid which is substituted by at least one fluorine atom and/or at least one group containing a fluorine atom.
2. A positive-working X-ray resist composition comprising:
(a) a compound capable of generating an acid by irradiation of an X-ray;
(b) a resin containing a group which is decomposed by action of an acid to increase solubility in an alkali developing solution; and
(c) a fluorine and/or silicon surfactant,
the compound capable of generating an acid by irradiation of an X-ray being a compound which generates benzenesulfonic acid, naphthalenesulfonic acid or anthracenesulfonic acid which is substituted by at least one fluorine atom and/or at least one group containing a fluorine atom.
3. The positive-working electron beam or X-ray resist composition of the above item 1 or 2, which further comprises (d) a low molecular weight dissolution inhibitive compound having a molecular weight of 3,000 or less which has a group decomposable with an acid and increases the rate of dissolution in the alkali developing solution by action of an acid.
4. A positive-working electron beam resist composition comprising:
(a) a compound capable of generating an acid by irradiation of an electron beam;
(c) a fluorine and/or silicon surfactant;
(d) a low molecular weight dissolution inhibitive compound having a molecular weight of 3,000 or less which has a group decomposable with an acid and increases the rate of dissolution in an alkali developing solution by action of the acid; and
(e) a resin insoluble in water and soluble in the alkali developing solution,
the compound capable of generating an acid by irradiation of an electron beam (component (a)) being a compound which generates benzenesulfonic acid, naphthalenesulfonic acid or anthracenesulfonic acid which is substituted by at least one fluorine atom and/or at least one group containing a fluorine atom.
5. A positive-working electron beam resist composition comprising:
(a) a compound capable of generating an acid by irradiation of an electron beam;
(c) a fluorine and/or silicon surfactant;
(d) a low molecular weight dissolution inhibitive compound having a molecular weight of 3,000 or less which has a group decomposable with an acid and increases the rate of dissolution in an alkali developing solution by action of the acid; and
(e) a resin insoluble in water and soluble in the alkali developing solution,
the compound capable of generating an acid by irradiation of an electron beam (component (a)) being a compound which generates benzenesulfonic acid, naphthalenesulfonic acid or anthracenesulfonic acid which is substituted by at least one fluorine atom and/or at least one group containing a fluorine atom.
6. The positive-working electron beam or X-ray resist compositions of the above items 1 to 5, wherein the compound capable of generating an acid by irradiation of an electron beam or X-ray (component (a)) is at least one compound selected from the group consisting of compounds represented by formulae (I) to (III) which generate an acid by irradiation of an X-ray:
wherein R
1
to R
37
, which may be the same or different, each represents a hydrogen atom, a straight-chain, branched or cyclic alkyl group, a straight-chain, branched or cyclic alkoxyl group, a hydroxyl group, a halogen atom or —S—R
38
, wherein R
38
represents a straight-chain, branched or cyclic alkyl group or an aryl group, and two or more of R
1
to R
15
, R
16
to R
27
or R
28
to R
37
may combine to form a ring containing one or two or more selected from the group consisting of a single bond, carbon, oxygen, sulfur and nitrogen; and X
−
represents an anion of benzenesulfonic acid, naphthalenesulfonic acid or anthracenesulfonic acid containing at least one selected from the group consisting of at least one fluorine atom, a straight-chain, branched or cyclic alkyl group substituted by at least one fluorine atom, a straight-chain, branched or cyclic alkoxyl group substituted by at least one fluorine atom, an acyl group substituted by at least one fluorine atom, an acyloxy group substituted by at least one fluorine atom, an alkyl or aryl sulfonyl group substituted by at least one fluorine atom, an alkyl or aryl sulfonyloxy group substituted by at least one fluorine atom, an alkyl or aryl sulfonylamino group substituted by at least one fluorine atom, an aryl group substituted by at least one fluorine atom, an aralkyl group substituted by at least one fluorine atom, and an alkoxycarbonyl group substituted by at least one fluorine atom.
DETAILED DESCRIPTION OF THE INVENTION
The positive-working electron beam or X-ray resist compositions of the present invention will be described in detail below.
[1] (a) Compounds Represented by General Formulae (I) to (III) (also Hereinafter Referred to as “Component (a)”)
Component (a) is a compound which generates an acid by irradiation of an electron beam or X-ray, preferably a compound which generates, by irradiation of an electron beam or X-ray, benzenesulfonic acid, naphthalenesulfonic acid or anthracenesulfonic acid which is substituted by at least one fluorine atom and/or at least one group containing at least one fluorine atom, more preferably the compounds represented by formulae (I) to (III).
In general formulae (I)
Aoai Toshiaki
Kodama Kunihiko
Uenishi Kazuya
Baxter Janet
Clarke Yvette M.
Fuji Photo Film Co. , Ltd.
Sughrue Mion Zinn Macpeak & Seas, PLLC
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