Radiation imagery chemistry: process – composition – or product th – Diazo reproduction – process – composition – or product – Composition or product which contains radiation sensitive...
Reexamination Certificate
1999-09-17
2001-06-12
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...
C430S192000, C430S196000, C430S197000, C430S270100, C430S920000
Reexamination Certificate
active
06245478
ABSTRACT:
The present invention relates to a resist composition, which is sensitive to radiations such as ultraviolet rays to give a positive or negative pattern and is suited for use in a fine working of semiconductors.
A resist causes a chemical change on irradiation with radiation and gives a positive or negative pattern by the following development. Known examples thereof include resist developed with an organic solvent and resist developed with an aqueous alkali solution. Examples of the resist developed with the aqueous alkali solution include novolak/quinonediazide type positive resists comprising an alkali-soluble novolak resin as a binder component and a quinonediazide compound as a radiation-sensitive component, novolak/azide type negative resists comprising the same alkali-soluble novolak resin as a binder component and an azide compound as a radiation-sensitive component, and chemical amplification type positive or negative resists comprising an alkali-soluble resin or a resin capable of being alkali-solubilized, as a binder component, and an active compound capable of generating an acid or base due to an action of radiation, as a radiation-sensitive component. The said chemical amplification type positive or negative resists utilize a catalytic action of the acid or base generated from the radiation-sensitive component.
With a recent trend of increased integration of integrated circuits, the formation of a submicron pattern has been required. As a result, resists having excellent resolution as well as excellent profile (shape of pattern) have been required. The finer the pattern becomes, the more a round top or a taper between the top and bottom of the pattern becomes conspicuous, thereby making it difficult to accurately reflect the shape of a mask on patterning exposure in the resulting pattern. Therefore, an improved resist composition capable of giving good profile has been required.
A simplest mean for improving the profile is that transparency of the resist is enhanced, for example, the amount of the radiation-sensitive component is decreased. However, the profile is not improved markedly only by decreasing the amount of the radiation-sensitive component to enhance the transparency. Further a decrease in amount of the radiation-sensitive component generally lowers the sensitivity.
An object of the present invention is to provide a resist composition capable of giving a profile having an excellent shape without impairing resist performances such as sensitivity and resolution.
The present inventors have intensively studied to attain such an object. As a result, they have found that a profile can be markedly improved by incorporating a certain compound into a resist composition containing a binder component and a radiation-sensitive component. Thus, the present invention was completed.
The present invention provides a resist composition comprising a binder component, a radiation-sensitive component, and a succinimide compound represented by the following formula (I):
wherein Q
1
represents an alkyl group which may be optionally substituted with alkoxy, halogen or nitro, an alicyclic hydrocarbon residue, an aryl group, or an aralkyl group; and Q
2
, which may be the same as or different from Q
1
, represents hydrogen, an alkyl group which may be optionally substituted with alkoxy, halogen or nitro, an alicyclic hydrocarbon residue, an aryl group, or an aralkyl group.
The present applicant has already filed a Japanese patent application (JP-A-10-261757) for a invention of a chemical amplification type positive resist composition comprising a resin having a structural unit represented by the following formula:
wherein R
1
and R
2
each independently represents an alkyl group or a cycloaklyl group, and total number of carbon atoms of the both is from 4 to 10, an acid generator, and a photo-base generator which has a substituted carbamoyloxy group represented by the following formula:
wherein R
3
represents a hydrocarbon residue, and is decomposed by an action of radiation to produce an amine. The present invention has been attained based on such a finding that a specific one among the aforementioned compounds having a substituted carbamoyloxy group as an effect of particularly improving a profile to various resist compositions.
In the resist composition of the present invention, a succinimide compound represented by the aforementioned formula (I) is incorporated, together with a binder component and a radiation-sensitive component. Q
1
and Q
2
in the formula (I) each independently represents an alkyl group, an alicyclic hydrocarbon residue, an aryl group, or an aralkyl group; with the proviso that Q
2
may also be hydrogen. Among them, the alkyl group may be substituted with alkoxy, halogen or nitro. The alkyl group may be an alkyl group having about 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isoproyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl or the like. The alkoxy, with which the alkyl group may be substituted, may be an alkoxy having about 1 to 4 carbon atoms. Halogen, with which the alkyl group may be substituted, may be chlorine, bromine or the like. Specific examples of the substituted alkyl group include 2-methoxyethyl and 2-chlorethyl. The alicyclic hydrocarbon residue, represented by Q
1
and Q
2
in the formula (I), may be monocyclic cycloaklyl or crosslinked polycyclic one, and usually has about 5 to 12 carbon atoms. Specific examples thereof include cyclopentyl, cyclohexyl, bornyl and admantyl. Examples of the aryl group include phenyl, tolyl, xylyl, methoxyphenyl and chlorophenyl. The aryl group usually has about 6 to 10 carbon atoms. Examples of the aralkyl group include benzyl, anisyl and phenyethyl. The aralkyl group usually has about 7 to 12 carbon atoms.
Among the succimimide compound represented by the formula (I), those wherein Q
2
is hydrogen, that is, N-(monosubstituted-carbamoyloxy)succinimide represented by the following formula (Ia):
is preferred.
Some of the succinimide compounds represented by the formula (I) are described in K. Takeda et al., Tetrahydron Letters, Vol. 24, 4569-4572 (1983). Therefore, the succinimide compounds are publicly known. This compound can be produced, for example, by reacting N-hydroxysuccinimide with carbamoyl chloride having groups represented by Q
1
and Q
2
in the formula (I), or with isocyanate having a group represented by Q
1
in case where Q
2
in the formula (I) is hydrogen, in the presence of a base, if necessary. These reactions are represented by the following reaction formulas:
wherein Q
1
and Q
2
are as defined above.
Alternatively, the succinimide compound of the formula (I) can also be produced, for example, by reacting succinimidyl chlorocarbonate with a primary or secondary amine having groups represented by Q
1
and Q
2
in the formula (I) in the presence of a base as a dehydrochlorinating agent according to the following reaction formula:
wherein Q
1
and Q
2
are as defined above. Succinimidyl chlorocarbonate used herein can be produced, for example, by the method described in T. Konakahara et al., SNYTHESIS, 103-106 (1993).
Examples of the succinimide compound represented by the formula (I) includes:
N-(methycarbamoyloxy)succinimide,
N-(ethylcarbamoyloxy)succinimide,
N-(hexylcarbamoyloxy)succinimide,
N-(cyclohexylcarbamoyloxy)succinimide,
N-(phenylcarbamoyloxy)succinimide,
N-(dimethylcarbamoyloxy)succinimde,
N-(diethylcarbamoyloxy)succinimide, and
N-(dicyclohexylcarbamoyloxy)succinimide.
By incorporating the succinimide compound represented by the formula (I) in the resist composition, the profile of a pattern obtained by irradiating a resist film formed from the composition with a radiation and developing can be improved. This reason is considered that this compound is hydrolyzed when coming into contact with a developer to generate a base (amine), thereby changing polarity of the compounds.
therefore, this succinimide compound is particularly effective for a resist composition developed with an aqueous alkali solution. As described hereinabove, the resist compo
Takemoto Ichiki
Uetani Yasunori
Birch & Stewart Kolasch & Birch, LLP
Chu John S.
Sumitomo Chemical Company Limited
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