Composition for resist underlayer film, process for forming resist underlayer film, patterning process, and fullerene derivative

• US 9,076,738 B2
• Filed: 07/14/2011
• Issued: 07/07/2015
• Est. Priority Date: 08/23/2010
• Status: Active Grant

• Current Assignee: Shin-Etsu Chemical Company Limited
• Original Assignee: Shin-Etsu Chemical Company Limited
• Inventors: Watanabe, Takeru, Fujii, Toshihiko, Kinsho, Takeshi, Ogihara, Tsutomu
• Primary Examiner(s): Toledo, Fernando L
• Assistant Examiner(s): Newton, Valerie N
• Application Number:
  US13/183,175
• Publication Number:
  US 20120045900A1
• Time in Patent Office: 1,454 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07C 2604/00 Fullerenes, e.g. C60 buckminsterfullerene or C70
• CPC Class Codes: C07C 69/753 of polycyclic acids
• CPC Class Codes: G03F 7/11 having cover layers or intermediate layers, e.g. subbing layers G03F7/091 - G03F7/093, B41N3/03 take precedence
• CPC Class Codes: H01L 21/0271 comprising organic layers
• CPC Class Codes: H01L 21/31116 by dry-etching
• CPC Class Codes: H01L 21/31144 using masks

Abstract

The invention provides a composition for a resist underlayer film, the composition for a resist underlayer film to form a resist underlayer film of a multilayer resist film used in lithography, wherein the composition comprises at least (A) a fullerene derivative that is a reaction product of a substance having a fullerene skeleton with a 1,3-diene compound derivative having an electron-withdrawing group and (B) an organic solvent. There can be a composition for a resist underlayer film for a multilayer resist film used in lithography, the composition giving a resist underlayer film having excellent high dry etching resistance, capable of suppressing wiggling during substrate etching with high effectiveness, and capable of avoiding a poisoning problem in upperlayer patterning that uses a chemical amplification resist; a process for forming a resist underlayer film; a patterning process; and a fullerene derivative.

Claims

1. A composition for a resist underlayer film of a multilayer resist film used in lithography, wherein the composition comprises at least (A) a fullerene derivative having an electron-withdrawing group and that is a reaction product of a substance having a fullerene skeleton with a 1,3-diene compound derivative having an electron-withdrawing group and (B) an organic solvent.

2. The composition for a resist underlayer film according to claim 1, wherein the fullerene derivative contains “

n”

numbers of a partial structure shown by the following general formula (1);

3. The composition for a resist underlayer film according to claim 1, wherein the electron-withdrawing group is any of a cyano group, a carboxyl group, a nitro group, a sulfo group, an acyl group, an alkoxy carbonyl group, an alkane sulfonyl group, and a trifluoromethyl group.

4. The composition for a resist underlayer film according to claim 2, wherein the electron-withdrawing group is any of a cyano group, a carboxyl group, a nitro group, a sulfo group, an acyl group, an alkoxy carbonyl group, an alkane sulfonyl group, and a trifluoromethyl group.

5. The composition for a resist underlayer film according to claim 1, wherein the 1,3-diene compound derivative having an electron-withdrawing group is a sorbate ester.

6. The composition for a resist underlayer film according to claim 2, wherein the 1,3-diene compound derivative having an electron-withdrawing group is a sorbate ester.

7. The composition for a resist underlayer film according to claim 3, wherein the 1,3-diene compound derivative having an electron-withdrawing group is a sorbate ester.

8. The composition for a resist underlayer film according to claim 4, wherein the 1,3-diene compound derivative having an electron-withdrawing group is a sorbate ester.

9. The composition for a resist underlayer film according claim 1, wherein the fullerene derivative contains “

n”

numbers of a partial structure shown by the following general formula (1a);

10. The composition for a resist underlayer film according claim 2, wherein the fullerene derivative contains “

n”

numbers of a partial structure shown by the following general formula (1a);

11. The composition for a resist underlayer film according claim 3, wherein the fullerene derivative contains “

n”

numbers of a partial structure shown by the following general formula (1a);

12. The composition for a resist underlayer film according claim 4, wherein the fullerene derivative contains “

n”

numbers of a partial structure shown by the following general formula (1a);

13. The composition for a resist underlayer film according claim 5, wherein the fullerene derivative contains “

n”

numbers of a partial structure shown by the following general formula (1a);

14. The composition for a resist underlayer film according claim 6, wherein the fullerene derivative contains “

n”

numbers of a partial structure shown by the following general formula (1a);

15. The composition for a resist underlayer film according claim 7, wherein the fullerene derivative contains “

n”

numbers of a partial structure shown by the following general formula (1a);

16. The composition for a resist underlayer film according claim 8, wherein the fullerene derivative contains “

n”

numbers of a partial structure shown by the following general formula (1a);

17. The composition for a resist underlayer film according to claim 1, further comprising (C) a resin having an aromatic ring.

18. The composition for a resist underlayer film according to claim 16, further comprising (C) a resin having an aromatic ring.

19. The composition for a resist underlayer film according to claim 17, wherein (C) the resin having an aromatic ring contains a naphthalene ring.

20. The composition for a resist underlayer film according to claim 18, wherein (C) the resin having an aromatic ring contains a naphthalene ring.

21. The composition for a resist underlayer film according to claim 17, wherein (C) the resin having an aromatic ring contains at least a compound (C1) that is obtained by polycondensation of a compound shown by the following general formula (2) and a compound shown by the following general formula (3) under an acidic condition:

A-CHO 

 

(3)

wherein

each R⁴ independently represents a hydrogen atom or a hydrocarbon group having 6 to 20 carbon atoms;

each R⁵ independently represents a benzene ring or a naphthalene ring;

1≦

m1+m2≦

2 and 1≦

m3+m4≦

2;

n1 and n2 are 0 or 1, respectively; and

A represents any of a hydrogen atom, a linear, a branched, or a cyclic saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, and an aromatic hydrocarbon group having 6 to 20 carbon atoms, wherein A may contain an ether group, a nitro group, a hydroxy group, or a chlorine group.

22. The composition for a resist underlayer film according to claim 20, wherein (C) the resin having an aromatic ring contains at least a compound (C1) that is obtained by polycondensation of a compound shown by the following general formula (2) and a compound shown by the following general formula (3) under an acidic condition:

A-CHO 

 

(3)

wherein

each R⁴ independently represents a hydrogen atom or a hydrocarbon group having 6 to 20 carbon atoms;

each R⁵ independently represents a benzene ring or a naphthalene ring;

1≦

m1+m2≦

2 and 1≦

m3+m4≦

2;

n1 and n2 are 0 or 1, respectively; and

A represents any of a hydrogen atom, a linear, a branched, or a cyclic saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, and an aromatic hydrocarbon group having 6 to 20 carbon atoms, wherein A may contain an ether group, a nitro group, a hydroxy group, or a chlorine group.

23. The composition for a resist underlayer film according to claim 1, further comprising at least one selected from the group consisting of (D) a phenolic-hydroxy group containing compound, (E) an acid generator, (F) a crosslinking agent, and (G) a surfactant.

24. The composition for a resist underlayer film according to claim 22, further comprising at least one selected from the group consisting of (D) a phenolic-hydroxy group containing compound, (E) an acid generator, (F) a crosslinking agent, and (G) a surfactant.

25. A process for forming a resist underlayer film of a multilayer resist film used in lithography, comprising applying the composition for a resist underlayer film according to claim 1 onto a substrate, and then curing the composition for a resist underlayer film by heat-treatment at a temperature of 200°

C. or higher and 600°

C. or lower and a time of 10 to 600 seconds to form a resist underlayer film.

26. A process for forming a resist underlayer film of a multilayer resist film used in lithography, comprising applying the composition for a resist underlayer film according to claim 1 onto a substrate, and then curing the composition for a resist underlayer film by baking under an atmosphere of oxygen concentration of 0.1% or higher and 21% or lower to form a resist underlayer film.

27. A patterning process for forming a pattern on a substrate by lithography, wherein the process comprises at least:

forming a resist underlayer film on a substrate by using the composition for a resist underlayer film according to claim 1,

forming, over the resist underlayer film, a resist intermediate film by using a silicon-containing composition for a resist intermediate film,

forming, over the resist intermediate film, a resist upperlayer film by using a composition for a resist upperlayer film comprised of a photo resist composition thereby forming a multilayer resist film,

forming a resist pattern of the resist upperlayer film by developing with a developer after a pattern circuit area of the resist upperlayer film is exposed,

etching the resist intermediate film by using a mask of the resist upperlayer film formed with the pattern,

etching the resist underlayer film by using a mask of the resist intermediate film at least formed with a pattern, and

etching the substrate by using a mask of the resist underlayer film at least formed with a pattern thereby forming a pattern on the substrate.

28. The patterning process according to claim 27, wherein etching of the resist underlayer film by using a mask of the resist intermediate film is carried out in an etching gas mainly comprised of an oxygen gas or a hydrogen gas.

29. A patterning process for forming a pattern on a substrate by lithography, wherein the process comprises at least:

forming a resist underlayer film on a substrate by using the composition for a resist underlayer film according to claim 1,

forming, over the resist underlayer film, an inorganic hard mask intermediate film selected from a silicon oxide film, a silicon nitride film, and a silicon oxynitride film,

forming, over the inorganic hard mask intermediate film, a resist upperlayer film by using a composition for a resist upperlayer film comprised of a photo resist composition,

forming a resist pattern of the resist upperlayer film by developing with a developer after a pattern circuit area of the resist upperlayer film is exposed,

etching the inorganic hard mask intermediate film by using the obtained resist pattern as an etching mask,

etching the resist underlayer film by using the obtained inorganic hard mask intermediate film pattern as an etching mask, and

etching the substrate by using the obtained resist underlayer film pattern as an etching mask thereby forming a pattern on the substrate.

30. A patterning process for forming a pattern on a substrate by lithography, wherein the process comprises at least:

forming a resist underlayer film on a substrate by using the composition for a resist underlayer film according to claim 1,

forming, over the resist underlayer film, an inorganic hard mask intermediate film selected from a silicon oxide film, a silicon nitride film, and a silicon oxynitride film,

forming, over the inorganic hard mask intermediate film, an organic anti-reflective film,

forming, over the organic anti-reflective film, a resist upperlayer film by using a composition for a resist upperlayer film comprised of a photo resist composition,

forming a resist pattern of the resist upperlayer film by developing with a developer after a pattern circuit area of the resist upperlayer film is exposed,

etching the organic anti-reflective film and the inorganic hard mask intermediate film by using the obtained resist pattern as an etching mask,

etching the resist underlayer film by using the obtained inorganic hard mask intermediate film pattern as an etching mask, and

etching the substrate by using the obtained resist underlayer film pattern as an etching mask to form a pattern on the substrate.

31. The patterning process according to claim 29, wherein the inorganic hard mask intermediate film is formed by a CVD method or an ALD method.

32. The patterning process according to claim 30, wherein the inorganic hard mask intermediate film is formed by a CVD method or an ALD method.

33. A fullerene derivative having “

n”

numbers of a partial structure shown by the following general formula (1a);