Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Reexamination Certificate
2002-07-19
2004-06-01
Robertson, Jeffrey B. (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
C528S012000, C528S021000, C528S033000, C528S043000, C525S477000
Reexamination Certificate
active
06743885
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to resin composition for intermediate layer of a three-layer resist.
BACKGROUND OF THE INVENTION
In pattern formation of a semiconductor substrate in production of LSI and bubble memory element and the like, a lithography method combining an organic resist and X-ray exposure is used. Recently, with progress of finer pattern dimension, improvement in pattern precision is required, consequently, a three-layer resist method has been developed.
The three-layer resist method is a method in which a resist for I-line made of a novolak resin or the like is applied on a substrate, this is thermally hardened to form a flattened layer insoluble in an organic solvent, an intermediate layer is applied on this, and thermally hardened, finally, an upper layer resist is applied, and the upper layer resist is exposed and developed to form a pattern which is sequentially transferred to lower layers by dry etching, to process the substrate.
As the intermediate layer of a three-layer resist, spin on glass (SOG), silicone resin and the like are conventionally used.
However, a film of SOG tends to be cracked in hardening, and application liquid thereof tends to change in properties with time, such as hardening and gelling.
When ketone compounds, aromatic compounds and the like are used as a resist solvent, an intermediate layer of silicone resin is dissolved in applying an upper layer resist, and a mixing layer is formed at the interface with the upper layer resist.
An object of the present invention is to provide resin composition for intermediate layer of a three-layer resist which, when ketone compounds, aromatic compounds and the like are used as a resist solvent, does not cause dissolution of an intermediate layer in applying an upper layer resist and does not cause formation of a mixing layer at the interface with the upper layer resist, and which shows little change in properties with time, excellent in storage stability, and can form a hardened film without cracking.
SUMMARY OF THE INVENTION
The present inventors have intensively studied to find resin composition causing no problems as describe above, and resultantly found that a resin composition comprising a polyorganosilsesquioxane resin having two or more functional groups, which polymerize or condense at the presence of an acid, in the molecule and having a weight-average molecular weight of from 1000 to 50000, and a compound generating an acid by electromagnetic wave or heat; when ketone compounds, aromatic compounds and the like are used as a resist solvent; does not cause dissolution of an intermediate layer in applying an upper layer resist and does not cause formation of a mixing layer at the interface with the upper layer resist, and shows little change in properties with time, excellent in storage stability, can form a hardened film without cracking, and suitable for intermediate layer of a three-layer resist.
Namely, the present invention provides resin composition for intermediate layer of a three-layer resist comprising (A) a polyorganosilsesquioxane resin having a weight-average molecular weight of from 1000 to 50000 and having two or more functional groups, which polymerize or condense at the presence of a acid, in the molecule, and (B) a compound generating an acid by electromagnetic wave or heat.
DETAILED DESCRIPTION OF THE INVENTION
The polyorganosilsesquioxane resin (A) used in the present invention is required to have a weight-average molecular weight of from 1000 to 50000, and it is preferably from 1000 to 20000.
When the weight-average molecular weight of the polyorganosilsesquioxane resin of the present invention is less than 1000, or when over 50000, film formation property is deteriorated.
Additionally, the polyorganosilsesquioxane has two or more functional groups, which polymerize or condense at the presence of an acid.
The functional groups may include oxetan or an alkoxysily groups of the general formulae (12) to (15) as shown later.
The polyorganosilsesquioxane resin (A) having oxetan group may be obtained by reacting two or more molecules of an organosilicon compound of the general formula (1).
In the formula (1), R represents a methyl group or ethyl group.
R′ represent a methoxy group, ethoxy group, or a mono-valent organic group having 1 to 20 carbon atoms, and when a plurality of R
1
are present, they may be the same or different.
R
1
to R
7
represent a hydrogen atom or a mono-valent organic group having 1 to 20 carbon atoms, and they may be the same or different.
k, l, m represent an integer of 0 or more, and n represents an integer of 1 to 3.
The mono-valent organic group having 1 to 20 carbon atoms may be any of linear, branched and cyclic, and for example, linear aliphatic hydrocarbon groups having 1 to 20 carbon atoms, branched aliphatic hydrocarbon groups having 3 to 20 carbon atoms, cyclic aliphatic hydrocarbon groups having 3 to 20 carbon atoms, aromatic hydrocarbon groups having 6 to 20 carbon atoms optionally substituted by an alkyl group, and the like are listed, and preferable are linear hydrocarbon groups having 1 to 6 carbon atoms, branched hydrocarbon groups having 3 to 6 carbon atoms, cyclic hydrocarbon groups having 3 to 6 carbon atoms, aromatic hydrocarbon groups having 6 to 20 carbon atoms optionally substituted by an alkyl group.
The alkyl group, for example, may include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group, isobutyl group, tertiary butyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like.
The aliphatic hydrocarbon group, for example, may include a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group, isobutyl group, tertiary butyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, chloromethyl group, dichloromethyl group, 2-chloroethyl group, 2,2-dichloroethyl group, 1,2-dichloroethyl group, 1,1-dichloroethyl group and the like.
The aromatic hydrocarbon group having 6 to 20 carbon atoms optionally substituted by an alkyl group, for example, may include a phenyl group, naphthyl group, anthryl group, tolyl group, xylyl group, dimethylphenyl group, trimethylphenyl group, ethylphenyl group, diethylphenyl group, triethylphenyl group, propylphenyl group, butylphenyl group, methylnaphthyl group, dimethylnaphthyl group, trimethylnaphthyl group, vinylnaphthyl group, ethenylnaphthyl group, methylanthryl group, ethylanthryl group and the like.
The polyorganosilsesquioxane resin (A) having oxetane group may be obtained by reacting two or more molecules of an organosilicon compound of the general formula (1), and this reaction is preferably a hydrolysis reaction carried out in the presence of an acid catalyst or alkali catalyst.
As the acid catalyst, for example, hydrochloric acid, acetic acid and the like are listed, and as the alkali catalyst, for example, ammonia, triethylamine and the like are listed.
The polyorganosilsesquioxane resin (A) having oxetane group may also be obtained by reacting two or more molecules of an oxetanylalkoxysilane of the general formula (1) and at least one molecule of organoalkoxysilene of the general formulae (2) to (5).
(RO)
4
Si (2)
(RO)
3
SiR
8
(3)
(RO)
2
SiR
9
R
10
(4)
(RO)SiR
11
R
12
R
13
(5)
In the formulae, R represents a methyl group or ethyl group.
R
8
to R
13
represent a mono-valent organic group having 1 to 20 carbon atoms, and may be the same or different.
As the mono-valent organic group having 1 to 20 carbon atoms, the same organic groups as described above are listed.
The reaction of two or more molecules of an oxetanylalkoxysilane of the general formula (1) and at least one molecule of organoalkoxysilanes of the general formulae (2) to (5) is also preferably a hydrolysis reaction carried out in the presence of an acid catalyst or alkali catalyst.
The polyorganosilsesquioxane resin (A) having oxetane group may also be obtained by reacting at least one molecule of
Moriuma Hiroshi
Uetani Yasunori
Yahagi Isao
Robertson Jeffrey B.
Sumitomo Chemical Company Limited
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