Silicon-containing resist underlayer film forming composition having urea group
There is provided a resist underlayer film forming composition for lithography for forming a resist underlayer film capable of being used as a hardmask. A resist underlayer film forming composition for lithography comprising: a hydrolyzable organosilane having a urea group; a hydrolysis product thereof; or a hydrolysis-condensation product thereof. The hydrolyzable organosilane is for example a compound of Formula (1): where at least one of three groups T 1 , T 2 , and T 3 is a group of Formula (2):
1. A resist underlayer film forming composition for lithography comprising:
(i) a composition of a hydrolysis product of the hydrolyzable organosilane of Formula (1) and at least one organic silicon compound selected from the group consisting of the organic silicon compound of Formula (4) and the organic silicon compound of Formula (5), and
(ii) a solvent,
wherein a solid content of the composition is 0.5% by mass to 50% by mass, and
wherein the hydrolyzable organosilane of Formula (1) is:
where:
at least one of T 1 , T 2 , and T 3 is a group of Formula (2):
where:
R 3 is an alkylene group, an arylene group, a halogenated alkylene group, a halogenated arylene group, an alkenylene group, or a divalent linking group derived from an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group,
n is 0 or 1,
R 4 is an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group,
R 5 is an alkoxy group, an acyloxy group, or a halogen atom, and
m is an integer of 0 or 1,
the others of T 1 , T 2 , and T 3 that are not a group of Formula (2) are independently a hydrogen atom, R 1 , or R 2 , where R 1 and R 2 are independently an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group, where R 1 and R 2 together optionally form a ring;
the organic silicon compound of Formula (4) is:
R 6 a Si(R 7 ) 4-a Formula (4)
where
R 6 is an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group, and is bonded to a silicon atom through a Si—C bond,
R 7 is an alkoxy group, an acyloxy group, or a halogen atom, and
a is an integer of 0 to 3; and
the organic silicon compound of Formula (5) is:
[R 8 c Si(R 9 ) 3-c ] 2 Y b Formula (5)
where
R 8 is an alkyl group,
R 9 is an alkoxy group, an acyloxy group, or a halogen atom,
Y is an alkylene group or an arylene group,
b is an integer of 0 or 1, and
c is an integer of 0 or 1; and
wherein in the at least one organic silicon compound selected from the group consisting of an organic silicon compound of Formula (4) and an organic silicon compound of Formula (5), phenyltrimethoxysilane or phenyltriethoxysilane is included.
2. The resist underlayer film forming composition according to claim 1 , wherein the hydrolyzable organosilane of Formula (1) is a compound obtained by reacting an isocyanate compound of Formula (3):
where R 3 , R 4 , R 5 , n, and m are the same as those defined in Formula (2) with ammonia, a primary amine, or a secondary amine.
3. The resist underlayer film forming composition according to claim 1 , wherein the hydrolyzable organosilane of Formula (1) is a compound obtained by reacting a hydrolyzable organosilane containing an amino group or an imino group with an isocyanate compound.
4. The resist underlayer film forming composition for lithography according to claim 1 , comprising:
a polymer of the hydrolysis-condensation product of a hydrolyzable organosilane of Formula (1), and
a polymer of the hydrolysis-condensation product of an organic silicon compound of Formula (4).
5. The resist underlayer film forming composition according to claim 1 , further comprising a curing catalyst.
6. A resist underlayer film obtained by applying the resist underlayer film forming composition as claimed in claim 1 on a semiconductor substrate and baking the composition.
7. The resist underlayer film forming composition according to claim 1 , wherein the composition (i) further comprises one or more selected from the group consisting of (a) the hydrolyzable organosilane of Formula (1) and at least one organic silicon compound selected from the group consisting of the organic silicon compound of Formula (4) and the organic silicon compound of Formula (5), and (b) a hydrolysis-condensation product of the hydrolyzable organosilane of Formula (1) and at least one organic silicon compound selected from the group consisting of the organic silicon compound of Formula (4) and the organic silicon compound of Formula (5).
8. A production method of a semiconductor device comprising:
applying a resist underlayer film forming composition on a semiconductor substrate and baking the composition to form a resist underlayer film;
applying a composition for a resist on the resist underlayer film to form a resist film;
exposing the resist film to light;
developing the resist after the exposure to produce a resist pattern;
etching the resist underlayer film through the resist pattern; and
processing the semiconductor substrate using the patterned resist and the patterned resist underlayer film,
wherein the resist underlayer film forming composition comprises:
(i) a composition selected from the group consisting of (a) a hydrolyzable organosilane of Formula (1) and at least one organic silicon compound selected from the group consisting of an organic silicon compound of Formula (4) and an organic silicon compound of Formula (5), (b) a hydrolysis product of the hydrolyzable organosilane of Formula (1) and at least one organic silicon compound selected from the group consisting of the organic silicon compound of Formula (4) and the organic silicon compound of Formula (5), (c) a hydrolysis-condensation product of the hydrolyzable organosilane of Formula (1) and at least one organic silicon compound selected from the group consisting of the organic silicon compound of Formula (4) and the organic silicon compound of Formula (5), and (d) combinations thereof, and
(ii) a solvent,
wherein a solid content of the composition is 0.5% by mass to 50% by mass, and
wherein the hydrolyzable organosilane of Formula (1) is:
where:
at least one of T 1 , T 2 , and T 3 is a group of Formula (2):
where:
R 3 is an alkylene group, an arylene group, a halogenated alkylene group, a halogenated arylene group, an alkenylene group, or a divalent linking group derived from an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group,
n is 0 or 1,
R 4 is an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group,
R 5 is an alkoxy group, an acyloxy group, or a halogen atom, and
m is an integer of 0 or 1,
the others of T 1 , T 2 , and T 3 that are not a group of Formula (2) are independently a hydrogen atom, R 1 , or R 2 , where R 1 and R 2 are independently an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group, where R 1 and R 2 together optionally form a ring;
the organic silicon compound of Formula (4) is:
R 6 a Si(R 7 ) 4-a Formula (4)
where
R 6 is an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group, and is bonded to a silicon atom through a Si—C bond,
R 7 is an alkoxy group, an acyloxy group, or a halogen atom, and
a is an integer of 0 to 3; and
the organic silicon compound of Formula (5) is:
[R 8 c Si(R 9 ) 3-c ] 2 Y b Formula (5)
where
R 8 is an alkyl group,
R 9 is an alkoxy group, an acyloxy group, or a halogen atom,
Y is an alkylene group or an arylene group,
b is an integer of 0 or 1, and
c is an integer of 0 or 1; and
wherein in the at least one organic silicon compound selected from the group consisting of an organic silicon compound of Formula (4) and an organic silicon compound of Formula (5), phenyltrimethoxysilane or phenyltriethoxysilane is included.
9. A production method of a semiconductor device comprising:
forming an organic film on a semiconductor substrate;
applying a resist underlayer film forming composition on the organic film and baking the composition to form a resist underlayer film;
applying a composition for a resist on the resist underlayer film to form a resist film;
exposing the resist film to light;
developing the resist after the exposure to produce a resist pattern;
etching the resist underlayer film through the resist pattern;
etching the organic underlayer film using the patterned resist underlayer film; and
processing the semiconductor substrate using the patterned organic underlayer film,
wherein the resist underlayer film forming composition comprises:
(i) a composition selected from the group consisting of (a) a hydrolyzable organosilane of Formula (1) and at least one organic silicon compound selected from the group consisting of an organic silicon compound of Formula (4) and an organic silicon compound of Formula (5), (b) a hydrolysis product of the hydrolyzable organosilane of Formula (1) and at least one organic silicon compound selected from the group consisting of the organic silicon compound of Formula (4) and the organic silicon compound of Formula (5), (c) a hydrolysis-condensation product of the hydrolyzable organosilane of Formula (1) and at least one organic silicon compound selected from the group consisting of the organic silicon compound of Formula (4) and the organic silicon compound of Formula (5), and (d) combinations thereof, and
(ii) a solvent,
wherein a solid content of the composition is 0.5% by mass to 50% by mass, and
wherein the hydrolyzable organosilane of Formula (1) is:
where:
at least one of T 1 , T 2 , and T 3 is a group of Formula (2):
where:
R 3 is an alkylene group, an arylene group, a halogenated alkylene group, a halogenated arylene group, an alkenylene group, or a divalent linking group derived from an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group,
n is 0 or 1,
R 4 is an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group,
R 5 is an alkoxy group, an acyloxy group, or a halogen atom, and
m is an integer of 0 or 1,
the others of T 1 , T 2 , and T 3 that are not a group of Formula (2) are independently a hydrogen atom, R 1 , or R 2 , where R 1 and R 2 are independently an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group, where R 1 and R 2 together optionally form a ring;
the organic silicon compound of Formula (4) is:
R 6 a Si(R 7 ) 4-a Formula (4)
where
R 6 is an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group, and is bonded to a silicon atom through a Si—C bond,
R 7 is an alkoxy group, an acyloxy group, or a halogen atom, and
a is an integer of 0 to 3; and
the organic silicon compound of Formula (5) is:
[R 8 c Si(R 9 ) 3-c ] 2 Y b Formula (5)
where
R 8 is an alkyl group,
R 9 is an alkoxy group, an acyloxy group, or a halogen atom,
Y is an alkylene group or an arylene group,
b is an integer of 0 or 1, and
c is an integer of 0 or 1; and
wherein in the at least one organic silicon compound selected from the group consisting of an organic silicon compound of Formula (4) and an organic silicon compound of Formula (5), phenyltrimethoxysilane or phenyltriethoxysilane is included.