Resist underlayer film forming composition containing silicon having nitrogen-containing ring
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, includes as a silane compound, a hydrolyzable organosilane, a hydrolysis product thereof, or a hydrolysis-condensation product thereof, wherein the hydrolyzable organosilane is a hydrolyzable organosilane of Formula (1): R 1 a R 2 b Si(R 3 ) 4−(a+b) Formula (1) wherein R 1 is Formula (2): in which R 4 is an organic group, and R 5 is a C 1-10 alkylene group, a hydroxyalkylene group, a sulfide bond, an ether bond, an ester bond, or a combination thereof, X 1 is Formula (3), Formula (4), or Formula (5): R 2 is an organic group, and R 3 is a hydrolysable group.
1. A resist underlayer film forming composition for lithography, comprising a silane compound, wherein the silane compound is a hydrolyzable organosilane, a hydrolysis product thereof, or a hydrolysis-condensation product thereof, wherein
the composition comprises as the hydrolyzable organosilane both (1) a hydrolyzable organosilane of Formula (1), and (2) a hydrolyzable organosilane of Formula (6), and wherein the composition comprises at least the hydrolysis-condensation product of the hydrolyzable organosilane of Formula (1) and the hydrolyzable silane of Formula (6) as a polymer:
R 1 a R 2 b Si(R 3 ) 4−(a+b) Formula (1)
where R 1 is Formula (2):
where in Formula (2), R 4 is a hydrogen atom, a C 1-10 alkyl group, an alkenyl group, an epoxy group, a sulfonyl group, or an organic group containing these groups and containing no Si atoms; R 5 is a C 1-10 alkylene group, a hydroxyalkylene group, a sulfide bond, an ether bond, an ester bond, or a combination thereof; and X 1 is Formula (3), Formula (4), or Formula (5):
where in Formula (3), Formula (4), and Formula (5), R 6 to R 10 are independently a hydrogen atom, a C 1-10 alkyl group, an alkenyl group, an epoxy group, a sulfonyl group, or an organic group containing these groups, and R 1 is bonded to a silicon atom through a Si—C bond;
where R 2 is an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl 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, or a combination thereof, and is bonded to a silicon atom through a Si—C bond;
where R 3 is an alkoxy group, an acyloxy group, or a halogen group; and
where a is an integer of 1 and b is an integer of 0 or 1, and where a+b is an integer of 1 or 2;
R 11 c Si(R 12 ) 4−c Formula (6)
where R 11 is an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, a sulfonyl group, a sulfide bond, an ether bond, an ester bond, a sulfonamide group, or a cyano group, or a combination thereof, and is bonded to a silicon atom through a Si—C bond;
where R 12 is an alkoxy group, an acyloxy group, or a halogen group; and
where c is an integer of 0 to 3.
2. The composition according to claim 1 , wherein the composition further comprises a hydrolyzable organosilane of Formula (7):
R 13 d R 14 e Si(R 15 ) 4−(d+e) Formula (7)
where R 13 is a cyclic amine or an organic group containing the same, and is bonded to a silicon atom through a Si—N bond or a Si—C bond;
where R 14 is an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, or a cyano group, or a combination thereof, and is bonded to a silicon atom through a Si—C bond;
where R 15 is an alkoxy group, an acyloxy group, or a halogen group; and
where d is an integer of 1 or 2 and e is an integer of 0 or 1, and where d+e is an integer of 1 or 2,
or a hydrolysis product thereof, or a hydrolysis-condensation product thereof.
3. The composition according to claim 1 , wherein the composition further comprises a hydrolyzable organosilane of Formula (8):
R 16 f R 17 g Si(R 18 ) 4−(f+g) Formula (8)
where R 16 is an alkoxyphenyl group, an acyloxyphenyl group, or an organic group containing these groups, and is bonded to a silicon atom through a Si—C bond;
where R 17 is an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, or a cyano group, or a combination thereof, and is bonded to a silicon atom through a Si—C bond;
where R 18 is an alkoxy group, an acyloxy group, or a halogen group; where R 16 and R 17 together optionally form a ring; and
where f is an integer of 1 or 2 and g is an integer of 0 or 1, where f+g is an integer of 1 or 2,
or a hydrolysis product thereof, or a hydrolysis-condensation product thereof.
4. The composition according to claim 1 , further comprising an acid.
5. The composition according to claim 1 , further comprising a salt.
6. The composition according to claim 1 , further comprising water.
7. The composition according to claim 1 , further comprising bisphenol S or a derivative thereof.
8. The composition according to claim 1 , wherein the hydrolyzable organosilane of Formula (1) is a hydrolyzable organosilane containing diallyl isocyanurate and the hydrolyzable silane of Formula (6) is a tetraalkoxysilane.
9. The composition according to claim 1 , wherein the hydrolyzable organosilane of Formula (1) is a hydrolyzable organosilane containing diallyl isocyanurate and the hydrolyzable organosilane of Formula (6) is a tetraalkoxysilane and an unsubstituted or substituted phenyltrialkoxysilane.
10. The composition according to claim 3 , wherein the hydrolyzable organosilane of Formula (1) is a silane compound containing diallyl isocyanurate, the hydrolyzable silane of Formula (6) is a tetraalkoxysilane, and the hydrolyzable organosilane of Formula (8) is a silane compound containing an alkoxyphenyl group.
11. The composition according to claim 3 , wherein the hydrolyzable organosilane of Formula (1) is a silane compound containing diallyl isocyanurate, the hydrolyzable silane of Formula (6) is a tetraalkoxysilane and an unsubstituted or substituted phenyltrialkoxysilane, and the hydrolyzable organosilane of Formula (8) is a hydrolyzable organosilane containing an alkoxyphenyl group.
12. 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 resultant coating film.
13. A production method of a semiconductor device, comprising:
applying the resist underlayer film forming composition as claimed in claim 1 on a semiconductor substrate and baking the resultant coating film to form a resist underlayer film;
applying a resist film forming composition on the underlayer film to form a resist film;
exposing the resist film to light;
developing the resist film after the exposure to obtain a patterned resist film;
etching the resist underlayer film according to the patterned resist film to pattern the resist underlayer film; and
processing the semiconductor substrate according to the patterned resist film and the patterned resist underlayer film.
14. A production method of a semiconductor device, comprising:
forming an organic underlayer film on a semiconductor substrate;
applying the resist underlayer film forming composition as claimed in claim 1 on the organic underlayer film and baking the resultant coating film to form a resist underlayer film;
applying a resist film forming composition on the resist underlayer film to form a resist film;
exposing the resist film to light;
developing the resist film after the exposure to obtain a patterned resist film;
etching the resist underlayer film according to the patterned resist film to pattern the resist underlayer film;
etching the organic underlayer film according to the pattered resist film and the patterned resist underlayer film; and
processing the semiconductor substrate according to the patterned organic underlayer film.
15. The composition according to claim 1 , wherein the silane comprises 20% by mass or more of the composition on a solids basis.
16. The composition according to claim 1 , wherein the silane comprises 50% to 100% by mass of the composition on a solids basis.