IP Library Granted Patent US 9,291,900
Granted Patent B2
US 9,291,900 · App. 13/981,142 · Granted Mar 22, 2016

Composition for forming resist underlayer film, containing silicon that bears diketone-structure-containing organic group

Inventors: Yuta Kanno (Toyama, JP); Daisuke Sakuma (Funabashi, JP); Makoto Nakajima (Toyama, JP)
Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
G03F7/0752C08L83/06C09D4/00C09D183/06G03F7/0755G03F7/0757G03F7/091G03F7/094G03F7/11G03F7/2041G03F7/30G03F7/36H01L21/3081H01L21/3088C08G77/14Y10T428/31663
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Quick Facts
Patent No.
US 9,291,900
App. No.
13/981,142
Granted
Mar 22, 2016
Kind
B2
Abstract

A composition for forming a lithographic resist underlayer film, including, as a silane, a hydrolyzable organosilane, a hydrolysate thereof, or a hydrolytic condensate thereof, wherein the silane includes a hydrolyzable organosilane of Formula (1) below: [(R 1 ) a Si(R 2 ) (3-a) ] b (R 3 )  Formula (1) [where R 3 is a group of Formula (2), (3), or (4): (in Formulae (2), (3), and (4), at least one from among R 4 , R 5 , and R 6 is a group bonded to a silicon atom directly or through a linking group.), R 1 is an alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide 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, R 2 is an alkoxy group, an acyloxy group, or a halogen atom].

Claims (50)

1. A method for producing a semiconductor device, comprising the steps of:

coating a composition for forming a lithographic resist underlayer film on a semiconductor substrate and performing baking to form a resist underlayer film;

coating a composition for forming a resist film on the underlayer film and forming a resist film;

exposing the resist film;

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 obtain a patterned resist underlayer film; and

processing the semiconductor substrate according to the patterned resist film and the patterned resist underlayer film,

wherein the composition for forming a resist underlayer film comprises as a silane, a hydrolyzable organosilane, a hydrolysate thereof, or a hydrolytic condensate thereof, wherein the silane includes a hydrolyzable organosilane of Formula (1) below:

[(R 1 ) a Si(R 2 ) (3-a) ] b (R 3 )  Formula (1)

[where R 3 is a group of Formula (2), (3), or (4):

(in Formulae (2), (3), and (4), at least one from among R 4 , R 5 , and R 6 is a group bonded to a silicon atom by a single bond or as a linking group; when R 4 is not bonded to the silicon atom, R 4 is a hydrogen atom, or an alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide 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;

when R 5 and R 6 are not bonded to the silicon atom, each of R 5 and R 6 is independently a linear alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide 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;

when any of R 4 , R 5 or R 6 is a group bonded to the silicon atom as a linking group, the group bonded to the silicon atom is a divalent group obtained by removing one hydrogen atom from the respective group defined above; however, when R 6 in Formula (3), R 5 in Formula (4), and R 6 in Formula (4) are bonded to the silicon atom, these groups are groups each bonded to the silicon atom as a linking group, rather than by a single bond);

each R 1 is independently an alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide 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; each R 2 is independently an alkoxy group, an acyloxy group, or a halogen atom; a is integer of 0 to 2, b is integer of 1 to 3].

2. The method according to claim 1 , wherein the hydrolyzable organosilane comprises at least one selected from a group consisting of a combination of at least one organosilicon compound selected from a group consisting of an organosilicon compound of Formula (5) below:

R 1 a Si(R 2 ) 4-a   Formula (5)

(where each R 1 is independently an alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an alkoxyaryl group, an acyloxyaryl group, or a cyano group, or a combination thereof, and is a group bonded to the silicon atom by a Si—C bond; each R 2 is independently an alkoxy group, an acyloxy group, or a halogen atom; a is integer of 0 to 3), and

an organosilicon compound of Formula (6) below:

[R 1 c Si(R 2 ) 3-c ] 2 Y b   Formula (6)

(where R 1 is an alkyl group, each R 2 is independently an alkoxy group, an acyloxy group, or a halogen atom, Y is an alkylene group or an arylene group, b is integer of 0 or 1, and c is integer of 0 or 1), and the hydrolyzable organosilane of Formula (1), hydrolysates thereof, and hydrolytic condensates thereof.

3. The method according to claim 1 , wherein the hydrolytic condensate of the hydrolyzable organosilane of Formula (1), or the hydrolytic condensate of the hydrolyzable organosilane of Formula (1) and the organosilicon compound of Formula (5) is contained as a polymer.

4. The method according to claim 1 , wherein the hydrolyzable organosilane of Formula (1) has a pKa value of 8.00 to 20.00.

5. The method according to claim 1 , wherein the composition for forming a lithographic resist underlayer film further comprises an acid as a hydrolysis catalyst.

6. The method according to claim 1 , wherein the composition for forming a lithographic resist underlayer film further comprises water.

7. A method for producing a semiconductor device, comprising the steps of:

forming an organic underlayer film on a semiconductor substrate;

coating a composition for forming a lithographic resist underlayer film on the organic underlayer film and performing baking to forrrl a resist underlayer film;

coating a composition for forming a resist film on the resist underlayer film and forming a resist film;

exposing the resist film;

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 obtain a patterned resist underlayer film;

etching the organic underlayer film according to the patterned resist underlayer film; and

processing the semiconductor substrate according to the patterned organic underlayer film,

wherein the composition for forming a lithographic resist underlayer film comprises as a silane, a hydrolyzable organosilane, a hydrolysate thereof, or a hydrolytic condensate thereof, wherein the silane includes a hydrolyzable organosilane of Formula (1) below:

[(R 1 ) a Si(R 2 ) (3-a) ] b (R 3 )  Formula (1)

[where R 3 is a group of Formula (2), (3), or (4):

(in Formulae (2), (3), and (4), at least one from among R 4 , R 5 , and R 6 is a group bonded to a silicon atom by a single bond or as a linking group; when R 4 is not bonded to the silicon atom, R 4 is a hydrogen atom, or an alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide 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;

when R 5 and R 6 are not bonded to the silicon atom, each of R 5 and R 6 is independently a linear alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide 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;

when any of R 4 , R 5 or R 6 is a group bonded to the silicon atom as a linking group, the groin bonded to the silicon atom is a divalent group obtained by removing one hydrogen atom from the respective group defined above; however, when R 6 in Formula (3), R 5 in Formula (4), and R 6 in Formula (4) are bonded to the silicon atom, these groups are groups each bonded to the silicon atom as a linking group, rather than by a single bond);

each R 1 is independently an alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide 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; each R 2 is independently an alkoxy group, an acyloxy group, or a halogen atom; a is integer of 0 to 2, b is integer of 1 to 3].

8. The method according to claim 7 , wherein the hydrolyzable organosilane comprises at least one selected from a group consisting of a combination of at least one organosilicon compound selected from a group consisting of an organosilicon compound of Formula (5) below:

R 1 a Si(R 2 ) 4-a   Formula (5)

(where each R 1 is independently an alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide group, an alkenyl group, or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an alkoxyaryl group, an acyloxyaryl group, or a cyano group, or a combination thereof, and is a group bonded to the silicon atom by a Si—C bond; each R 2 is independently an alkoxy group, an acyloxy group, or a halogen atom; a is integer of 0 to 3), and

an organosilicon compound of Formula (6) below:

[R 1 c Si(R 2 ) 3-c ] 2 Y b   Formula (6)

(where R 1 is an alkyl group, each R 2 is independently an alkoxy group, an acyloxy group, or a halogen atom, Y is an alkylene group or an arylene group, b is integer of 0 or 1, and c is integer of 0 or 1), and the hydrolyzable organosilane of Formula (1), hydrolysates thereof, and hydrolytic condensates thereof.

9. The method according to claim 7 , wherein the hydrolytic condensate of the hydrolyzable organosilane of Formula (1), or the hydrolytic condensate of the hydrolyzable organosilane of Formula (1) and the organosilicon compound of Formula (5) is contained as a polymer.

10. The method according to claim 7 , wherein the hydrolyzable organosilane of Formula (1) has a pKa value of 8.00 to 20.00.

11. The method according to claim 7 , wherein the composition for forming a lithographic resist underlayer film further comprises an acid as a hydrolysis catalyst.

12. The method according to claim 7 , wherein the composition for forming a lithographic resist underlayer film further comprises water.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 23, 2013
From: KANNO, YUTA; SAKUMA, DAISUKE; NAKAJIMA, MAKOTO
To: NISSAN CHEMICAL INDUSTRIES, LTD.
Reel/Frame 030900/0366 →
Priority Claims (1)
JP 2011-012338 · Jan 24, 2011 · national
Continuity (1)
Related Publication 20130302991A1 · Nov 14, 2013