IP Library › Granted Patent US 10,372,039
Granted Patent B2
US 10,372,039 · App. 14/439,791 · Granted Aug 6, 2019

Resist underlayer film forming composition containing silicon having ester group

Inventors: Yuta Kanno (Toyama, JP); Makoto Nakajima (Toyama, JP); Satoshi Takeda (Toyama, JP); Hiroyuki Wakayama (Toyama, JP)
Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
G03F7/0757C08G77/14C08G77/26C08G77/28C08G77/80C09D183/06C09D183/08G03F7/0752G03F7/091G03F7/094G03F7/30G03F7/322G03F7/325G03F7/36G03F7/40H01L21/02126H01L21/02282H01L21/0332
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Quick Facts
Patent No.
US 10,372,039
App. No.
14/439,791
Granted
Aug 6, 2019
Kind
B2
Abstract

A resist underlayer film forming composition for lithography for a resist underlayer film usable as a hardmask. A resist underlayer film forming composition for lithography, including: as a silane, a hydrolyzable silane, a hydrolysis product thereof, or a hydrolysis-condensation product thereof, wherein the hydrolyzable silane includes a hydrolyzable silane of Formula (1) or a hydrolyzable silane containing a combination of a hydrolyzable silane of Formula (1) with a hydrolyzable silane of Formula (2), and a content of the hydrolyzable silane of Formula (1) or the hydrolyzable silane containing a combination of a hydrolyzable silane of Formula (1) with a hydrolyzable silane of Formula (2) in all silanes is less than 50% by mole, R 1 a R 2 b Si(R 3 ) 4−(a+b)   Formula (1) R 4 a1 R 5 b1 Si(R 6 ) 4−(a1+b1)   Formula (2).

Claims (72)

1. A resist underlayer film forming composition for lithography, comprising:

as a silane, a hydrolyzable silane, a hydrolysis product thereof, or a hydrolysis-condensation product thereof, wherein

the hydrolyzable silane contains:

a hydrolyzable silane containing a combination of a hydrolyzable silane of Formula (1) with a hydrolyzable silane of Formula (2), and

an other hydrolyzable silane,

wherein the other hydrolyzable silane is at least one organic silicon compound selected from the group consisting of:

a compound of Formula (3):

R 7 a2 Si(R 8 ) 4−a2   Formula (3)

where in Formula (3), R 7 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, or a cyano group, and is bonded to a silicon atom through a Si—C bond; R 8 is an alkoxy group, an acyloxy group, or a halogen group; and a 2 is an integer of 0 to 3,

and a compound of Formula (4):

[R 9 c Si(R 10 ) 3−c ] 2 Y b2   Formula (4)

where in Formula (4), R 9 is an alkyl group and is bonded to a silicon atom through a Si—C bond; R 10 is an alkoxy group, an acyloxy group, or a halogen group; Y is an alkylene group or an arylene group; b 2 is an integer of 0 or 1; and c is an integer of 0 or 1, and

the other hydrolyzable silane contains a substituted phenyl silane and a methyl silane, and

a content of the hydrolyzable silane containing a combination of a hydrolyzable silane of Formula (1) with a hydrolyzable silane of Formula (2) in all silanes is 10 to 20% by mole,

R 1 a R 2 b Si(R 3 ) 4−(a+b)   Formula (1)

where in Formula (1), R 1 is a monovalent organic group containing a group of Formula (1-1), Formula (1-2), Formula (1-3), Formula (1-4), or Formula (1-5):

where in Formula (1-1), Formula (1-2), Formula (1-3), Formula (1-4), and Formula (1-5), each of T 1 and T 7 is an alkylene group, a cyclic alkylene group, an alkenylene group, an arylene group, a sulfur atom, an oxygen atom, an oxycarbonyl group, an amido group, a secondary amino group, or a combination of these groups and atoms; T 2 is an alkyl group; each of T 3 and T 5 is an aliphatic ring or an aromatic ring; T 4 is a cyclic alkylene group, an alkenylene group, an arylene group, a sulfur atom, an oxygen atom, an oxycarbonyl group, an amido group, a secondary amino group, or a combination of these groups and atoms; each of T 6 and T 8 is a lactone ring; and n is an integer of 1 or 2, and R 1 is bonded to a silicon atom through a Si—C bond; R 2 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 3 is an alkoxy group, an acyloxy group, or a halogen group; and a is an integer of 1, b is an integer of 0 or 1, and a+b is an integer of 1 or 2,

R 4 a1 R 5 b1 Si(R 6 ) 4−(a1+b1)   Formula (2)

where in Formula (2), R 4 is a monovalent organic group containing a group of Formula (2-1), Formula (2-2), or Formula (2-3):

and R 4 is bonded to a silicon atom through a Si—C bond; R 5 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 6 is an alkoxy group, an acyloxy group, or a halogen group; and a 1 is an integer of 1, b 1 is an integer of 0 or 1, and a 1 +b 1 is an integer of 1 or 2; wherein

the hydrolyzable silane does not contain:

a combination of a hydrolyzable silane of Formula (1) in which R 1 is a monovalent organic group containing Formula (1-1) with a hydrolyzable silane of Formula (2) in which R 4 is a monovalent organic group containing Formula (2-3),

a combination of a hydrolyzable silane of Formula (1) in which R 1 is a monovalent organic group containing Formula (1-4) with a hydrolyzable silane of Formula (2) in which R 4 is a monovalent organic group containing Formula (2-3), and

a combination of a hydrolyzable silane of Formula (1) in which R 1 is a monovalent organic group containing Formula (1-5) with a hydrolyzable silane of Formula (2) in which R 4 is a monovalent organic group containing Formula (2-3).

2. The resist underlayer film forming composition according to claim 1 , wherein

a hydrolyzable silane of Formula (2) is a hydrolyzable silane in which R 4 is an organic group containing a group of Formula (2-1), a hydrolyzable silane in which R 4 is an organic group containing a group of Formula (2-2), a hydrolyzable silane in which R 4 is an organic group containing a group of Formula (2-3), or a mixture of these hydrolyzable silanes.

3. The resist underlayer film forming composition according to claim 1 , wherein

a hydrolyzable silane containing a combination of a hydrolyzable silane of Formula (1) with a hydrolyzable silane of Formula (2) contains a hydrolyzable silane of Formula (1) and a hydrolyzable silane of Formula (2) in a molar ratio of 1:0.01 to 1:10.

4. A resist underlayer film forming composition comprising:

a hydrolysis product of a hydrolyzable silane containing a combination of a hydrolyzable silane of Formula (1) with a hydrolyzable silane of Formula (2), and a hydrolyzable silane of Formula (3) as claimed in claim 1 , as a polymer,

wherein the hydrolyzable silane containing a combination of a hydrolyzable silane of Formula (1) with a hydrolyzable silane of Formula (2) contains a hydrolyzable silane of Formula (1) and a hydrolyzable silane of Formula (2) in a molar ratio of 1:0.01 to 1:10.

5. The resist underlayer film forming composition according to claim 1 , further comprising an acid as a hydrolysis catalyst.

6. The resist underlayer film forming composition according to claim 1 , further comprising water.

7. A resist underlayer film obtained by applying the resist underlayer film forming composition as claimed in claim 1 onto a semiconductor substrate, and baking the composition.

8. A method for producing a semiconductor device, the method comprising:

applying the resist underlayer film forming composition as claimed in claim 1 onto a semiconductor substrate and baking the composition to form a resist underlayer film;

applying a composition for a resist onto the underlayer film to form a resist film;

exposing the resist film to light;

developing the resist after the exposure to obtain a resist pattern;

etching the resist underlayer film using the resist pattern; and

processing the semiconductor substrate using the patterned resist and the patterned resist underlayer film.

9. A method for producing a semiconductor device, the method comprising:

forming an organic underlayer film on a semiconductor substrate;

applying the resist underlayer film forming composition as claimed in claim 1 , onto the organic underlayer film and baking the composition to form a resist underlayer film;

applying a composition for a resist onto the resist underlayer film to form a resist film;

exposing the resist film to light;

developing the resist after the exposure to obtain a resist pattern;

etching the resist underlayer film using 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.

10. A resist underlayer film forming composition for lithography, comprising:

as a silane, a hydrolyzable silane, a hydrolysis product thereof, or a hydrolysis-condensation product thereof, wherein

the hydrolyzable silane contains:

a hydrolyzable silane of Formula (1), and

an other hydrolyzable silane,

wherein the other hydrolyzable silane is at least one organic silicon compound selected from the group consisting of:

a compound of Formula (3):

R 7 a2 Si(R 8 ) 4−a2   Formula (3)

where in Formula (3), R 7 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, or a cyano group, and is bonded to a silicon atom through a Si—C bond; R 8 is an alkoxy group, an acyloxy group, or a halogen group; and a 2 is an integer of 0 to 3,

and a compound of Formula (4):

[R 9 c Si(R 10 ) 3−c ] 2 Y b2   Formula (4)

where in Formula (4), R 9 is an alkyl group and is bonded to a silicon atom through a Si—C bond; R 10 is an alkoxy group, an acyloxy group, or a halogen group; Y is an alkylene group or an arylene group; b 2 is an integer of 0 or 1; and c is an integer of 0 or 1, and

the other hydrolyzable silane contains a substituted phenyl silane and a methyl silane, and

a content of the hydrolyzable silane of Formula (1) in all silanes is 10 to 20% by mole,

R 1 a R 2 b Si(R 3 ) 4−(a+b)   Formula (1)

where in Formula (1),

R 1 is a monovalent organic group containing a group of Formula (1-1), Formula (1-2), or Formula (1-3):

where in Formula (1-1), Formula (1-2), and Formula (1-3), T 1 an alkylene group, a cyclic alkylene group, an alkenylene group, an arylene group, a sulfur atom, an oxygen atom, an oxycarbonyl group, an amido group, a secondary amino group, or a combination of these groups and atoms; T 2 is an alkyl group; T 3 is an aliphatic ring or an aromatic ring; T 4 is a cyclic alkylene group, an alkenylene group, an arylene group, a sulfur atom, an oxygen atom, an oxycarbonyl group, an amido group, a secondary amino group, or a combination of these groups and atoms; and n is an integer of 1 or 2;

R 1 is bonded to a silicon atom through a Si—C bond;

R 2 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 3 is an alkoxy group, an acyloxy group, or a halogen group; and

a is an integer of 1, b is an integer of 0 or 1, and a+b is an integer of 1 or 2.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2015
From: KANNO, YUTA; NAKAJIMA, MAKOTO; TAKEDA, SATOSHI; WAKAYAMA, HIROYUKI
To: NISSAN CHEMICAL INDUSTRIES, LTD.
Reel/Frame 035536/0347 →
Priority Claims (2)
JP 2012-240249 · Oct 31, 2012 · national
JP 2012-249620 · Nov 13, 2012 · national
Continuity (1)
Related Publication 20150316849A1 · Nov 5, 2015