Photosensitive polymer containing Si, Ge or Sn and resist...

Details Photosensitive polymer containing Si, Ge or Sn and resist... Photosensitive polymer containing Si, Ge or Sn and resist...

2001-09-13

2004-01-13

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

C430S325000, C430S326000, C430S905000, C430S910000, C430S914000, C430S921000, C430S925000, C526S240000, C526S241000, C526S271000, C526S279000, C526S270000, C526S328000

Reexamination Certificate

active

06677100

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a chemically amplified resist composition, and more particularly, to a photosensitive polymer containing silicon and a resist composition comprising the same.
2. Description of the Related Art
As processes for manufacturing semiconductor devices become more complicated and the integration density of semiconductor devices increases, the need to form finer patterns becomes more pronounced. Furthermore, to manufacture semiconductor memory devices having a capacity of 1 Gigabit or more, a pattern size having a design rule of 0.2 &mgr;m or less is needed. Accordingly, there is a limitation in forming such a fine pattern using conventional photoresist materials using a KrF excimer laser (248 nm). For this reason, a lithography technique using a new exposure light source, the ArF excimer laser (193 nm), has emerged.
However, a resist material suitable for use in lithography with the ArF excimer laser causes many problems for practical use, compared with conventional resist materials. The most serious problem is the collapse of patterns with respect to an increase in the aspect ratio. Therefore, patterns must be formed using resist layers having a thickness of 4000 angstroms or less. Other problems associated with the ArF resist include the transmittance of the polymer. The ArF resist has inferior transmittance as compared to the KrF resist. This is another reason why the thickness of the ArF resist layer must be reduced.
Almost all well-known ArF resists have a resistance to dry etching that is equal or inferior to that of the KrF resist. Therefore, when an underlying layer is patterned by lithography using resist patterns obtained from the conventional resist materials, a satisfactory profile cannot be obtained.
Recently, to solve the foregoing problems, a technique using a bi-layer resist (BLR) has been suggested. In a process using BLR, the lithography is performed using a resist material containing silicon. Silicon atoms within the resist material are glassed in the form of SiO
X
during dry etching by O
2
plasma to form a cured layer, and the cured layer is used as an etching mask during a subsequent dry etching process. Therefore, when the aspect ratio is large, resistance to dry etching is increased by the curing layer, so that it is easy to form patterns, and collapse of patterns can also be prevented. As a result, patterns having a large aspect ratio can be formed with high resolving power.
The amount of silicon in a polymer is an important factor for a BLR. Generally, as the amount of silicon increases, the likelihood that there will be problems due to a reduction in the thermal stability of the resist layer and the wettability to a developer increases. Therefore, the polymer must contain the right amount of silicon for a BLR process, and development of a resist material having excellent thermal stability and wettability to a developer becomes a serious requirement.
SUMMARY OF THE INVENTION
It is a feature of the present invention to provide a photosensitive polymer that has a sufficient silicon content, that has a reduced manufacturing cost, and that provides excellent lithography characteristics when used as a resist material.
It is another feature of the present invention to provide a resist composition having a silicon content sufficient to be used as a BLR for ArF excimer laser lithography, and at the same time, has excellent thermal stability and wettability to a developer.
In accordance with one aspect of the present invention, there is provided a photosensitive polymer comprising a copolymer including acrylate or methacrylate monomer unit having a group indicated as the following formula (I), and a maleic anhydride monomer unit,
wherein R
1
, R
2
, and R
3
are independently a hydrogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, a benzyl group, a phenoxy group, or —M(R′)
3
, wherein M is Si, Ge, Sn, or OSi, and each R′ independently is a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, or a phenoxy group.
In a more particular embodiment, the photosensitive polymer comprises a copolymer having the following structural formula (II):
wherein R
4
is a hydrogen atom or a C
1
-C
4
alkyl group, R
5
, R
6
, and R
7
are independently a hydrogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, a benzyl group, a phenoxy group, or —M(R′)
3
, wherein M is Si, Ge, Sn or OSi, and each R′ independently is a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, or a phenoxy group, and m/(m+n) is between about 0.2-0.9.
In another more particular embodiment, the photosensitive polymer comprises a copolymer having the following structural formula (III):
wherein R
4
is a hydrogen atom or a C
1
-C
4
alkyl group, R
5
, R
6
, R
7
, R
8
, and R
9
are independently a hydrogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, a benzyl group, a phenoxy group, or —M(R′)
3
, wherein M is Si, Ge, Sn or OSi, and each R′ independently is a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, or a phenoxy group, and m/(m+n) is between about 0.2-0.9.
In a further more particular embodiment, the photosensitive polymer comprises a copolymer having the following structural formula (IV):
wherein R
4
is a hydrogen atom or a C
1
-C
4
alkyl group, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, and R
11
are independently a hydrogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, a benzyl group, a phenoxy group, or —M(R′)
3
, wherein M is Si, Ge, Sn or OSi, and each R′ independently is a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, or a phenoxy group, and m/(m+n) is between about 0.2-0.9.
In accordance with another aspect of the present invention, there is provided a photosensitive polymer comprising a terpolymer including an acrylate or methacrylate monomer unit having a group indicated as the following formula (I), a maleic anhydride monomer unit, and a cyclic vinyl ether monomer unit,
wherein R
1
, R
2
, and R
3
are independently a hydrogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, a benzyl group, a phenoxy group, or —M(R′)
3
, wherein M is Si, Ge, Sn, or OSi, and each R′ independently is a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, or a phenoxy group.
In a more particular embodiment, the photosensitive polymer comprises a terpolymer having the following structural formula (V):
wherein, R
4
is a hydrogen atom or a C
1
-C
4
alkyl group, R
5
, R
6
, and R
7
are independently a hydrogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, a benzyl group, a phenoxy group, or —M(R′)
3
, wherein M is Si, Ge, Sn, or OSi, and each R′ independently is a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, or a phenoxy group, k is an integer from 1 to 6, and m/(m+n) is between about 0.2-0.9.
In another more particular embodiment, the photosensitive polymer comprises a terpolymer having the following structural formula (VI):
wherein R
4
is a hydrogen atom or a C
1
-C
4
alkyl group, R
5
, R
6
, R
7
, R
8
, and R
9
are independently a hydrogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, a benzyl group, a phenoxy group, or —M(R′)
3
, wherein M is Si, Ge, Sn, or OSi, and each R′ independently is a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, or a phenoxy group, k is an integer from 1 to 6, and m/(m+n) is between about 0.2-0.9.
In a further more particular embodiment, the photosensitive polymer comprises a terpolymer having the following structural formula (VII):
wherein R
4
is a hydrogen atom or a C
1
-C
4
alkyl group, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, and R
11
are independently a hydrogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a phenyl group, a benzyl group, a phenoxy group, or —M(R′)
3
, where

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