Chemistry of inorganic compounds – Treating mixture to obtain metal containing compound – Radioactive metal
Reexamination Certificate
2002-03-27
2003-09-23
Moore, Margaret G. (Department: 1712)
Chemistry of inorganic compounds
Treating mixture to obtain metal containing compound
Radioactive metal
Reexamination Certificate
active
06623711
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a siloxane-based resin and a method for forming insulating film between interconnect layers in semiconductor devices by using the same. More specifically, the present invention relates to a siloxane-based resin prepared by hydrolyzing and polycondensing cyclic and/or cage-shape siloxane compounds, optionally with at least one silane compound, in an organic solvent in the presence of a catalyst and water. The present invention also relates to a method for forming insulating film between interconnect layers in semiconductor devices, wherein the siloxane-based resin described above is used as low dielectric insulating materials.
BACKGROUND OF THE INVENTION
As the circuit density in multilevel integrated circuit devices increases, the reduction of feature size in a semiconductor device is strongly required. But, there are fatal problems such as R(resistance)×C(capacitance) delay due to crosstalk between interconnect lines. Therefore, dielectric constant of interlayer insulating films should be lowered so as to decrease the RC delay as much as possible. For this purpose, there have been various attempts to develop low dielectric materials for use in the insulating film.
For example, polysilsesquioxanes having dielectric constant of approximately 2.5~3.1 has replaced SiO
2
having dielectric constant of 4.0 in chemical vapor deposition(CVD). Such polysilsesquioxanes can be also applied to a spin coating method due to its excellent planation property.
The polysilsesquioxanes as well as preparing methods thereof are well known in the art. For example, U.S. Pat. No. 3,615,272 discloses a method for preparing completely condensed soluble hydrogensilsesquioxane resins, which comprises the steps of condensing trichlorosilanes in a sulfuric acid medium, and then washing the resulting resins with water or aqueous sulfuric acid. U.S. Pat. No. 5,010,159 discloses a method for synthesizing soluble condensed hydridosilicon resins, which comprises the steps of hydrolyzing hydridosilanes in an arylsulfuric acid hydrate-containing hydrolysis medium, and then contacting the resulting resins with a neutralizing agent. U.S. Pat. No. 6,232,424 describes a highly soluble silicone resin composition having excellent solution stability, which was prepared by hydrolyzing and polycondensing tetraalkoxysilane, organosilane and organotrialkoxysilane monomers in the presence of water and a catalyst. U.S. Pat. No. 6,000,339 teaches that a silica-based compound, which may be useful for improving the resistance and physical properties as well as thickness of a coating film, can be obtained from a reaction of a monomer selected from the group consisting of alkoxysilane, fluorine-containing alkoxysilane and alkylalkoxysilane and a titanium- or zirconium-alkoxide compound in the presence of water and a catalyst. U.S. Pat. No. 5,853,808 describes that silsesquioxane polymers that are useful for preparing SiO
2
-rich ceramic coatings can be obtained as the polymeric reaction products from the hydrolysis and condensation of organosilanes having a &bgr;-substituted alkyl group.
However, the prior polysilsesquioxane resins have not accomplished very low dielectric constant that is currently required for insulating film between interconnect layers in semiconductor devices. Additionally, they have been required to improve in mechanical properties, thermal stability, crack-resistance, and so on.
SUMMARY OF THE INVENTION
A feature of the present invention is a method for forming low dielectric insulating film between interconnect layers in semiconductor devices by using a siloxane-based resin having very low dielectric constant, wherein the resin is obtained from the copolymerization of cyclic and/or cage-shape siloxane compounds optionally with one or more silane compounds.
An aspect of the present invention relates to siloxane-based resins that are prepared by hydrolyzing and polycondensing a cyclic siloxane compound of formula (1) and a cage-shape siloxane compound of any of formulas (2a)-(2c) in an organic solvent in the presence of a catalyst and water:
wherein,
R is H, C
1-3
alkyl, C
3-10
cycloalkyl, or C
6-15
aryl;
each of X
1
, X
2
, and X
3
is, independently, C
1-3
alkyl, C
1-10
alkoxy, or halo, provided that at least one is alkoxy or halo;
p is an integer from 3 to 8; and
m is an integer from 1 to 10;
in the above formulas (2a)-(2c),
each of X
1
, X
2
, and X
3
is, independently, C
1-3
alkyl, C
1-10
alkoxy, or halo,
provided that at least one is alkoxy or halo; and
n is an integer from 1 to 12.
Another aspect of the present invention relates to siloxane-based resins that are prepared by hydrolyzing and polycondensing a cyclic siloxane compound of formula (1) and a cage-shape siloxane compound of any of formulas (2a)-(2c), together with a silane compound of formula (3) and/or a silane compound of formula (4), in an organic solvent in the presence of a catalyst and water:
wherein,
R is H, C
1-3
alkyl, C
3-10
cycloalkyl, or C
6-15
aryl;
each of X
1
, X
2
, and X
3
is, independently, C
1-3
alkyl, C
1-10
alkoxy, or halo, provided that at least one is alkoxy or halo;
p is an integer from 3 to 8; and
m is an integer from 1 to 10;
in the above formulas 2(a)-2(c),
each of X
1
, X
2
, and X
3
is, independently, C
1-3
alkyl, C
1-10
alkoxy, or halo, provided that at least one is alkoxy or halo; and
n is an integer from 1 to 12;
SiX
1
X
2
X
3
X
4
(3)
wherein,
each of X
1
, X
2
, X
3
, and X
4
is, independently, C
1-10
alkoxy, or halo;
RSiX
1
X
2
X
3
(4)
wherein,
R is H, C
1-3
alky, C
3-10
cycloalkyl, or C
6-15
aryl; and
each of X
1
, X
2
, and X
3
is, independently, C
1-3
alkyl, C
1-10
alkoxy, or halo, provided that at least one is alkoxy or halo.
Still another aspect of the present invention relates to siloxane-based resins that are prepared by hydrolyzing and polycondensing a cyclic siloxane compound of formula (1), together with a silane compound of formula (3) and/or a silane compound of formula (4), in an organic solvent in the presence of a catalyst and water:
wherein,
R is H, C
1-3
alkyl, C
3-10
cycloalkyl, or C
6-15
aryl;
each of X
1
, X
2
, and X
3
is, independently, C
1-3
alkyl, C
1-10
alkoxy, or halo, provided that at least one is alkoxy or halo;
p is an integer from 3 to 8; and
m is an integer from 1 to 10;
SiX
1
X
2
X
3
X
4
(3)
wherein,
each of X
1
, X
2
, X
3
, and X
4
is, independently, C
1-10
alkoxy, or halo;
RSiX
1
X
2
X
3
(4)
wherein,
R is H, C
1-3
alkyl, C
3-10
cycloalkyl, or C
6-15
aryl; and
each of X
1
, X
2
, and X
3
is, independently, C
1-3
alkyl, C
1-10
alkoxy, or halo, provided that at least one is alkoxy or halo.
Still another aspect of the present invention relates to siloxane-based resins that are prepared by hydrolyzing and polycondensing a cage-shape siloxane compound of any of formulas (2a)-(2c), together with a silane compound of formula (3) and/or a silane compound of formula (4), in an organic solvent in the presence of a catalyst and water:
in the above formulas (2a)-(2c),
each of X
1
, X
2
, and X
3
is, independently, C
1-3
alkyl, C
1-10
alkoxy, or halo, provided that at least one is alkoxy or halo; and
n is an integer from 1 to 12;
SiX
1
X
2
X
3
X
4
(3)
wherein,
each of X
1
, X
2
, X
3
, and X
4
is, independently, C
1-10
alkoxy, or halo;
RSiX
1
X
2
X
3
(4)
wherein,
R is H, C
1-3
alkyl, C
3-10
cycloalkyl, or C
6-15
aryl; and
each of X
1
, X
2
, and X
3
is, independently, C
1-3
alkyl, C
1-10
alkoxy, or halo, provided that at least one is alkoxy or halo.
Still another aspect of the present invention relates to a method for forming insulating film between interconnect layers in semiconductor devices, the method comprising the steps of: providing a resinous solution by dissolving the siloxane-based resin described above in an organic solvent; coating a silicon wafer with the resinous solution; and heat-curing the resulting coating film.
All of the above feature
Hwang Il Sun
Jeong Hyun Dam
Kim Jung Hyung
Lyu Yi Yeol
Mah Sang Kook
Birch & Stewart Kolasch & Birch, LLP
Moore Margaret G.
Samsung Electronics Co,. Ltd.
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