IP Library Granted Patent US 10,036,954
Granted Patent B2
US 10,036,954 · App. 15/267,923 · Granted Jul 31, 2018

Pattern-forming method, resin, and composition

Inventors: Shun Aoki (Tokyo, JP); Hiromitsu Tanaka (Tokyo, JP); Goji Wakamatsu (Tokyo, JP); Yoshio Takimoto (Tokyo, JP); Masayoshi Ishikawa (Tokyo, JP); Toru Kimura (Tokyo, JP)
Assignee: JSR CORPORATION
G03F7/11C07C217/18C07C279/08C08G8/04C08G8/20C08G8/36C08L61/06C09D161/14C09D183/04G03F7/075G03F7/094G03F7/26G03F7/322G03F7/38G03F7/405H01L21/02057H01L21/0274H01L21/3081H01L21/30604Y02P20/582
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Quick Facts
Patent No.
US 10,036,954
App. No.
15/267,923
Granted
Jul 31, 2018
Kind
B2
Abstract

A pattern-forming method comprises: forming a resist underlayer film on an upper face side of a substrate; forming a silicon-containing film on an upper face side of the resist underlayer film; and removing at least a part of the resist underlayer film and at least a part of the silicon-containing film with a basic aqueous solution. Preferably, the pattern-forming method further comprises, after the forming of the silicon-containing film and before the removing of the resist underlayer film and the silicon-containing film, forming a resist pattern on an upper face side of the silicon-containing film, and etching the silicon-containing film using the resist pattern as a mask.

Claims (80)

1. A pattern-forming method comprising:

forming a resist underlayer film on an upper face side of a substrate;

forming a silicon-containing film on an upper face side of the resist underlayer film;

forming a resist pattern on an upper face side of the silicon-containing film;

etching the silicon-containing film using the resist pattern as a mask; and

removing at least a part of the resist underlayer film and at least a part of the silicon-containing film with a basic aqueous solution.

2. The pattern-forming method according to claim 1 , wherein the basic aqueous solution is a liquid comprising tetraalkylammonium hydroxide and water, or a liquid obtained by mixing ammonia, hydrogen peroxide and water.

3. The pattern-forming method according to claim 1 , wherein the basic aqueous solution comprises none of hydrogen fluoride, a salt thereof, and a salt of a fluorine compound.

4. The pattern-forming method according to claim 1 , wherein the removing of the resist underlayer film and the silicon-containing film is carried out at a temperature of less than 100° C.

5. The pattern-forming method according to claim 1 , wherein the resist underlayer film is formed from a composition that comprises an aromatic ring-containing resin.

6. The pattern-forming method according to claim 5 , wherein the aromatic ring-containing resin is a novolak resin, an acenaphthylene resin or a combination thereof.

7. The pattern-forming method according to claim 6 , wherein the resin comprises a resin comprising a structural unit represented by formula (1):

wherein, in the formula (1),

Z 1 represents a substituted or unsubstituted alkanediyl group, a substituted or unsubstituted arenediyl group or a substituted or unsubstituted oxyalkanediyl group;

p1 represents number of Z 1 that bonds to the aromatic ring, and is an integer of 1 to 10, wherein p1 is no less than 2, a plurality of Z 1 s are identical or different;

R 1 and R 5 each independently represent a monovalent organic group having 1 to 20 carbon atoms;

m1 is an integer of 0 to 6, wherein in a case where m1 is no less than 2, a plurality of R 1 s are identical or different;

m3 is an integer of 0 to 6, wherein in a case where m3 is no less than 2, a plurality of R 5 s are identical or different;

R 2 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms;

m2 is an integer of 1 to 8, wherein in a case where m2 is no less than 2, a plurality of R 2 s are identical or different; and

n is an integer of 0 to 2,

wherein a sum of m1, m2, m3 and p1 is no greater than 10.

8. The pattern-forming method according to claim 7 , wherein R 2 in the formula (1) represents —R 3 —COOR 4 , wherein R 3 represents a divalent organic group having 1 to 20 carbon atoms, and R 4 represents an organic group having 1 to 20 carbon atoms.

9. The pattern-forming method according to claim 8 , wherein R 3 represents a group obtained by removing one hydrogen atom from at least one group selected from the group consisting of an alkyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a glycidyl ether group, and an alkylglycidyl ether group, wherein the number of carbon atoms of the alkyl moiety of the alkylglycidyl group is 1 to 6.

10. The pattern-forming method according to claim 9 , wherein R 4 represents a tertiary alkyl group.

11. The pattern-forming method according to claim 8 , wherein R 3 represents a group obtained by removing one hydrogen atom from at least one group selected from the group consisting of an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a glycidyl ether group, and an alkylglycidyl ether group, wherein the number of carbon atoms of the alkyl moiety of the alkylglycidyl group is 1 to 6.

12. The pattern-forming method according to claim 11 , wherein R 4 represents a tertiary alkyl group.

13. The pattern-forming method according to claim 8 , wherein R 4 represents a tertiary alkyl group.

14. The pattern-forming method according to claim 1 , wherein the resist underlayer film is formed from a composition that comprises a calixarene compound.

15. The pattern-forming method according to claim 14 , wherein the calixarene compound is represented by formula (2):

wherein, in the formula (2),

R 6 represents a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms;

r is an integer of 4 to 12;

Y represents a hydrocarbon group having 1 to 10 carbon atoms;

k is 0 or 1;

m4 is an integer of 1 to 3;

m5 is an integer of 0 to 7, wherein a sum of m4 and m5 is no greater than 8; and

X 1 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms or a hydrogen atom,

wherein

in a case where m4 is no less than 2, a plurality of R 6 s are identical or different,

in a case where m5 is no less than 2, a plurality of Ys are identical or different, and

in a case where r is no less than 2, a plurality of X 1 s are identical or different, a plurality of ks are identical or different, a plurality of m4s are identical or different and a plurality of m5s are identical or different.

16. The pattern-forming method according to claim 1 , wherein the silicon-containing film is formed from a composition comprising:

a hydrolytic condensation product of a silane compound comprising a compound represented by formula (3); and

an organic solvent,

R 7 a SiX 2 4-a   (3)

wherein, in the formula (3),

R 7 represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 5 carbon atoms, a cyano group, a cyanoalkyl group, an alkylcarbonyloxy group, an acid anhydride group, an alkenyl group, an aryl group or an aralkyl group, wherein the alkyl group is unsubstituted or substituted with a fluorine atom, and the aryl group and the aralkyl group are unsubstituted or substituted;

X 2 represents a halogen atom or —OR 8 , wherein R 8 represents a monovalent organic group; and

a is an integer of 0 to 3, wherein

in a case where R 7 is present in a plurality of number, a plurality of R 7 s are identical or different, and

in a case where X 2 is present in a plurality of number, a plurality of X 2 s are identical or different.

17. A resin comprising a structural unit represented by formula (1-1):

wherein, in the formula (1-1),

Z 1 represents a substituted or unsubstituted alkanediyl group, a substituted or unsubstituted arenediyl group or a substituted or unsubstituted oxyalkanediyl group;

p1 represents number of Z 1 that bonds to the aromatic ring, and is an integer of 1 to 10, wherein in a case where p1 is no less than 2, a plurality of Z 1 s are identical or different;

R 1 and R 5 each independently represent a monovalent organic group having 1 to 20 carbon atoms;

m1 is an integer of 0 to 6, wherein in a case where m1 is no less than 2, a plurality of R 1 s are identical or different;

m3 is an integer of 0 to 6, wherein in a case where m3 is no less than 2, a plurality of R 5 s are identical or different;

m2 is an integer of 1 to 8;

R 3 represents a group obtained by removing one hydrogen atom from at least one group selected from the group consisting of an alkyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a glycidyl ether group, and an alkylglycidyl ether group, wherein the number of carbon atoms of the alkyl moiety of the alkylglycidyl group is 1 to 6;

R 4 represents a tertiary alkyl group,

wherein in a case where m2 is no less than 2, a plurality of R 3 s are identical or different and a plurality of R 4 s are identical or different; and

n is an integer of 0 to 2,

wherein a sum of m1, m2, m3 and p1 is no greater than 10.

18. The resin according to claim 17 , wherein R 3 represents a group obtained by removing one hydrogen atom from at least one group selected from the group consisting of an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a glycidyl ether group, and an alkylglycidyl ether group, wherein the number of carbon atoms of the alkyl moiety of the alkylglycidyl group is 1 to 6.

19. A composition comprising a solvent and a resin which comprises a structural unit represented by formula (1-1):

wherein, in the formula (1-1),

Z 1 represents a substituted or unsubstituted alkanediyl group, a substituted or unsubstituted arenediyl group or a substituted or unsubstituted oxyalkanediyl group;

p1 represents number of Z 1 that bonds to the aromatic ring, and is an integer of 1 to 10, wherein in a case where p1 is no less than 2, a plurality of Z 1 s are identical or different;

R 1 and R 5 each independently represent a monovalent organic group having 1 to 20 carbon atoms;

m1 is an integer of 0 to 6, wherein in a case where m1 is no less than 2, a plurality of R 1 s are identical or different;

m3 is an integer of 0 to 6, wherein in a case where m3 is no less than 2, a plurality of R 5 s are identical or different;

m2 is an integer of 1 to 8;

R 3 represents a group obtained by removing one hydrogen atom from at least one group selected from the group consisting of an alkyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a glycidyl ether group, and an alkylglycidyl ether group, wherein the number of carbon atoms of the alkyl moiety of the alkylglycidyl group is 1 to 6;

R 4 represents a tertiary alkyl group,

wherein in a case where m2 is no less than 2, a plurality of R 3 s are identical or different and a plurality of R 4 s are identical or different; and

n is an integer of 0 to 2,

wherein a sum of m1, m2, m3 and p1 is no greater than 10.

20. The composition according to claim 19 , wherein R 3 represents a group obtained by removing one hydrogen atom from at least one group selected from the group consisting of an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, a glycidyl ether group, and an alkylglycidyl ether group, wherein the number of carbon atoms of the alkyl moiety of the alkylglycidyl group is 1 to 6.

Assignments (3)
MERGER Recorded Mar 23, 2026
From: JSR CORPORATION
To: JICC-02, CO., LTD
Reel/Frame 075191/0149 →
CHANGE OF NAME Recorded Mar 23, 2026
From: JICC-02 CO., LTD
To: JSR CORPORATION
Reel/Frame 075192/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2016
From: AOKI, SHUN; TANAKA, HIROMITSU; WAKAMATSU, GOJI; TAKIMOTO, YOSHIO; ISHIKAWA, MASAYOSHI; KIMURA, TORU
To: JSR CORPORATION
Reel/Frame 039768/0111 →
Priority Claims (1)
JP 2014-060960 · Mar 24, 2014 · national
Continuity (2)
Continuation PCTJP2015056424 · Mar 4, 2015
Related Publication 20170003595A1 · Jan 5, 2017