Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
1999-06-24
2002-04-16
Lipman, Bernard (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S926000, C525S328200, C525S328300, C525S328800, C525S328900, C525S338000, C525S339000
Reexamination Certificate
active
06372854
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a novel hydrogenated ring-opening metathesis polymer and, more particularly, to a hydrogenated ring-opening metathesis polymer, which is superior in heat resistance, pyrolysis resistance and light transmission properties and which is suited for use as a photoresist polymer for microlithography by ultraviolet and far ultraviolet lights (including excimer lasers) in the production of semiconductor devices, and a method of producing the hydrogenated polymer.
2. Description of the Related Art
With the recent increase of integration level in integrated circuits on semiconductor devices, a large-scale integrated circuit (LSI) and a very-large-scale integrated circuit (VLSI) have been put to practical use and, at the same time, a minimum lithographic pattern in the integrated circuits would be reaching in sub-micron features, in future, it tends to be more microlithographic. In the formation of the microlithographic pattern, there is essentially required to use a lithography technique of coating a surface of a substrate with a resist material to form a thin film, selectively exposing the resulting resist film to light thereby to form a latent image of a desired pattern, developing the latent image to form a resist pattern, performing dry etching using this resist pattern as a mask, and removing the resist to obtain a desired pattern.
As an exposure light source used in this lithographic technique, for example, ultraviolet lights of g-lines (wavelength: 436 nm) or i-lines (wavelength: 365 nm) have been used. With the progress of the fine lithographic pattern, it has become popular to use an exposure light having a shorter wavelength such as far ultraviolet lights, vacuum ultraviolet lights, electron beams (EB) and X-rays as the light source. As the exposure light source, excimer laser (e.g. KrF laser having a wavelength of 248 nm, ArF laser having a wavelength of 193 nm, etc.) has attracted special interest recently and it is expected that the excimer laser is effective for formation of the fine lithographic pattern.
As a polymer or copolymer used as a resist material for formation of a sub-micron pattern using exposure light having a shorter wavelength within a vacuum ultraviolet region, for example, there have been suggested various polymers and copolymers, such as polymer or copolymer of an acrylic or &agr;-substituted acrylic ester having an adamantane skeleton and an acid cleavable protecting group at an ester portion (see Japanese Patent Kokai Publication No. 39665/1992), polymer or copolymer of an acrylic or &agr;-substituted acrylic ester having a norbornane skeleton and an acid cleavable protecting group at an ester portion (see Japanese Patent Kokai Publication No. 257281/1993), polymer or copolymer of cyclohexylmaleimide (see Japanese Patent Kokai Publication No. 257285/1993), polymer compound containing a cellulose skeleton in a principal chain, said principal chain being cleaved by an acid (see Japanese Patent Kokai Publication No. 342212/1994), polyvinyl alcohol or its derivative (see Japanese Patent Kokai Publication No. 333850/1995) and the like.
However, there have still not been obtained polymers and copolymers, which satisfy all of various properties required to be used as the polymer for the resist material, such as dry etching resistance, transparency to far ultraviolet lights, solubility in resist solvent, wettability by developer, adhesion to substrate such as silicon, solubility in releasant and the like, and a further development thereof is required.
On the other hand, a cyclic polymer in a photoresist composition (WO97/33198) comprising a polymer compound having an aliphatic cyclic hydrocarbon as a principal chain and containing pendant acid cleavable groups is superior in dry etching resistance and also superior in transparency to far ultraviolet lights. However, it had a problem that the solubility in resist solvent in high concentration, wettability by developer and adhesion to silicon substrate are inferior.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a hydrogenated ring-opening metathesis polymer, which satisfy all of the above various properties required to be used as a polymer for the resist material and also has a narrow molecular weight distribution, and to provide a method of producing the hydrogenated polymer.
Another object of the present invention to provide a resist material using the hydrogenated polymer, which is superior in dry etching resistance, transparency to far ultraviolet lights, solubility in resist solvent, wettability by developer, adhesion to substrate such as silicon, and solubility in releasant.
To solve the above problems, the present inventors have studied intensively about a possibility of using a hydrogenated ring-opening metathesis polymer obtained from a cyclic olefinic monomer or monomers as a polymer for resist material having excellent optical characteristics, electrical characteristics, high rigidity, heat resistance, adhesion to substrate and weathering resistance. As a result, they have found that a novel hydrogenated ring-opening metathesis polymer satisfies various performances as the resist material, thus completing the present invention.
That is, the present invention provides:
(i) A hydrogenated ring-opening metathesis polymer comprising at least a structural unit (A) represented by the following general formula (1):
wherein at least one of R
1
to R
4
is a substituent containing an acid cleavable group, and others are selected from hydrogen, an alkyl group having 1 to 20 carbon atoms, a halogen, a halogenated alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxyalkyl group having 2 to 20 carbon atoms, an alkylcarbonyloxy group having 2 to 20 carbon atoms, an arylcarbonyloxy group having 7 to 20 carbon atoms, an alkylsulfonyloxy group having 1 to 20 carbon atoms, an arylsulfonyloxy group having 6 to 20 carbon atoms, a carboxy group, a hydroxy group, a carboxyalkyl group having 2 to 20 carbon atoms, or a hydroxyalkyl group having 1 to 20 carbon atoms; X
1
is selected from —O—, —S—, —NR
5
—, —PR
5
— or —CR
5
2
— (R
5
represents hydrogen or an alkyl group having 1 to 20 carbon atoms) and may be the same or different; and m represents 0 or an integer of 1 to 3; a structural unit (B) represented by the following general formula (2):
wherein at least one of R
6
to R
9
is a substituent containing carboxy or hydroxy, and others are selected from hydrogen, an alkoxy group having 1 to 20 carbon atoms, an alkoxyalkyl group having 2 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a halogen, a halogenated alkyl group having 1 to 20 carbon atoms, an alkylcarbonyloxy group having 2 to 20 carbon atoms, an arylcarbonyloxy group having 7 to 20 carbon atoms, an alkylsulfonyloxy group having 1 to 20 carbon atoms, or an arylsulfonyloxy group having 6 to 20 carbon atoms; X
2
is selected from —O—, —S—, —NR
10
—, —PR
10
— or —CR
10
2
— (R
10
represents hydrogen or an alkyl group having 1 to 20 carbon atoms) and may be the same or different; and n represents 0 or an integer of 1 to 3; and a structural unit (C) represented by the following general formula (3):
wherein at least one of R
11
to R
14
is a substituent containing cyano or lactonyloxycarbonyl, and others are selected from hydrogen, a carboxy group, a hydroxy group, a carboxyalkyl group having 2 to 20 carbon atoms, a hydroxyalkyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkoxycarbonylalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxyalkyl group having 2 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a halogen, or a halogenated alkyl group having 1 to 20 carbon atoms; X
3
is selected from —O—, —S—, —NR
15
—, —PR
15
— or —CR
15
2
— (R
15
represents hydrogen or an alkyl group having 1 to 20 carbon atoms) and may be the same or different; and 1 represents 0 or an integer of 1 to 3,
where
Ikeda Keiichi
Kawahara Nobuo
Okita Masumi
Sunaga Tadahiro
Takao Toshiro
Burns Doane Swecker & Mathis L.L.P.
Lipman Bernard
Mitsui Chemicals Inc.
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