Radiation imagery chemistry: process – composition – or product th – Diazo reproduction – process – composition – or product – Composition or product which contains radiation sensitive...
Reexamination Certificate
2002-08-27
2004-02-10
Chu, John S. (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Diazo reproduction, process, composition, or product
Composition or product which contains radiation sensitive...
C430S165000, C430S192000, C430S193000, C430S287100, C430S288100
Reexamination Certificate
active
06689531
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a resist composition used for fine processing of semiconductors.
2. Prior Art
In general, a photolithography process is used for producing integrated circuits and liquid crystal display elements. It is known that as the resist used in such a process, compositions containing a novolak resin and a dissolution inhibiting agent having a quinone diazide group are suitable, and such compositions are used widely in lithography using g line, i line and the like. However, even these resists revealed a necessity for improvement in close adherence in a wet etching process and heat resistance in a plasma etching process, for precise formation of fine patterns.
Recently, with progress in higher integration, there occurs a requirement for capability of precise formation of submicron fine patterns. Excimer laser lithography is paid to attention since it enables production of 64 M DRAM to 1 G DRAM. As the resist suitable for such an excimer laser lithography process, there is a tendency to adoption of a so-called chemical amplification type resist utilizing chemical amplification effect of an acid catalyst. In the case of the chemical amplification type resist, an acid is generated from an acid generating agent at parts irradiated with radiation, and solubility of the irradiated parts in an alkali developer is changed in a reaction using this acid as a catalyst, by the subsequent heat treatment (post exposure bake: hereinafter, abbreviated as PEB) in some cases. By this, positive or negative patterns are provided.
These resists are generally a composition showing high transparency at exposure wavelength, since high resolution is required. For example, as the resist for KrF excimer laser lithography, often used are poly(p-hydroxystyene) based resins in which a part of phenolic hydroxyl groups is protected with a group dissociating by the action of an acid. However, when wet etching treatment and the like are conducted using these chemical amplification type resists, there is a problem that peeling of a formed pattern from the edge due to insufficient close adherence at the interface of a substrate with a resist, reverse influence due to impregnation of etching liquid and the like are caused.
SUMMARY OF THE INVENTION
The object of the present invention is to provide a resist composition, particularly a positive resist composition giving improved close adherence at the interface of a substrate with a resist, improving the problems in wet etching treatment, and excellent in sensitivity, resolution and heat resistance.
The present inventors have intensively studied, and resultantly found that by containing a specific compound, a resist composition giving improved close adherence at the interface of a substrate with a resist and capable of improving the problems in wet etching treatment is obtained. Based on this findings and further various studies, the present invention was completed.
Namely, the present invention relates to [1] a resist composition comprising a compound of the general formula (I):
wherein, R
1
and R
2
represent each independently a hydrogen atom or an alkyl group, R
3
represents a hydrogen atom, alkyl group, aryl group, aralkyl group, alkenyl group, alkylcarbonyl group, arylcarbonyl group or aralkylcarbonyl group provided that the alkyl group, aryl group, aralkyl group, alkenyl group, alkylcarbonyl group, arylcarbonyl group and aralkylcarbonyl group may be optionally substituted with a carboxy group, oxycarbonyl group, hydroxy group, alkoxy group or alkyl group, n represents an integer of 1 to 40, m represents an integer of 1 to 5, and l represents an integer of 1 to 5.
Further, the present invention relates to [2] a positive resist composition comprising an alkali-soluble resin, a dissolution inhibiting agent and a compound of the general formula (I).
Furthermore, the present invention relates to [3] a chemical amplification type positive resist composition comprising a resin insoluble or poorly soluble itself in an alkali aqueous solution but becoming soluble in an alkali aqueous solution by the action of an acid, an acid generating agent and a compound of the above-mentioned general formula (I).
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The resist composition of the present invention is characterized in that it comprises a compound of the above-mentioned formula (I). The compound of the formula (I) can be used alone or in combination of two or more.
In the formula (I), R
1
and R
2
represent each independently a hydrogen atom or an alkyl group, preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, further preferably a hydrogen atom or a methyl group.
R
3
represents a hydrogen atom, alkyl group, aryl group, aralkyl group, alkenyl group, alkylcarbonyl group, arylcarbonyl group or aralkylcarbonyl group, preferably a hydrogen atom, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 15 carbon atoms, aralkyl group having 7 to 15 carbon atoms, alkenyl group having 2 to 10 carbon atoms, alkylcarbonyl group having 2 to 10 carbon atoms, arylcarbonyl group having 7 to 15 carbon atoms or aralkylcarbonyl group having 7 to 15 carbon atoms. Among the above, a hydrogen atom, alkylcarbonyl group having 2 to 10 carbon atoms, arylcarbonyl group having 7 to 15 carbon atoms and aralkylcarbonyl group having 7 to 15 carbon atoms are more preferable.
The alkyl group, aryl group, aralkyl group, alkenyl group, alkylcarbonyl group, arylcarbonyl group or aralkylcarbonyl group may be optionally substituted with a carboxy group, oxycarbonyl group, hydroxy group, alkoxy group or alkyl group.
The alkyl group, alkenyl group include straight chain, branched and cyclic groups.
As R
3
, particularly a group represented by the following formula (II) is preferable.
n represents an integer of 1 to 40, preferably of 1 to 20. m represents an integer of 1 to 5, and l represents an integer of 1 to 5.
The end of the compound of the formula (I) is a hydrogen atom.
The compound of the general formula (I) preferably has a weight-average molecular weight measured by gel permeation chromatography (GPC) in terms of polystyrene of 500 to 20000.
Specific examples of the compound corresponding to the formula (I) include the following compounds.
A compound of the formula (I) wherein R
3
represents H, such as a compound of the formula (IIIc) is obtained by adding an unsaturated monocarboxylic acid such as acrylic acid, methacrylic acid or the like, according to a known method, to a novolak epoxy resin such as a cresol novolak epoxy resin, phenol novolak epoxy resin or the like. Further, by effecting an addition reaction to the hydroxyl group (esterification) according to a known method, compounds of the formula (I) wherein R
3
represents various groups are obtained. For example, if tetrahydrophthalic anhydride is reacted with a novolak epoxy resin, compounds corresponding to the formula (IIIa) and the formula (IIIb) are obtained.
The compounds of the formula (I) are also commercially available, and exemplified are resins manufactured by Showa Kobunshi K.K. (trade name: PR-310), and the like.
The alkali-soluble resin used in the resist composition of the present invention (composition [2]) is not particularly restricted, and those known in the art can be used. Preferably used are novolak resins. The novolak resin is usually obtained by condensation of a phenol-based compound and an aldehyde in the presence of an acid catalyst. Examples of the phenol-based compound used in production of the novolak resins include phenol, o-, m- or p-cresol, 2,3-, 2,5-, 3,4- or 3,5-xylenol, 2,3,5-trimethylphenol, 2-, 3- or 4-tert-butylphenol, 2-tert-butyl-4- or 5-methylphenol, 2-, 4- or 5-methylresorcinol, 2-, 3- or 4-methoxyphenol, 2,3-, 2,5- or 3,5-dimethoxyphenol, 2-methoxyresorcinol, 4-tert-butylcatechol, 2-, 3- or 4-ethylphenol, 2,5- or 3,5-diethylphenol, 2,3,5-triethylphenol, 2-naphthol, 1,3-, 1,5- or 1,7-dihydroxynaphthalene, polyhydroxytriphenylmethane-based compounds ob
Kang Seung Jin
Kim Sang Tae
Suetsugu Masumi
Sung Shi Jin
Yamada Airi
Chu John S.
Sumitomo Chemical Company Limited
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