IP Library Granted Patent US 6,989,457
Granted Patent B2
US 6,989,457 · App. 10/345,616 · Granted Jan 24, 2006

Chemical vapor deposition precursors for deposition of tantalum-based materials

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Quick Facts
Patent No.
US 6,989,457
App. No.
10/345,616
Granted
Jan 24, 2006
Kind
B2
Abstract

Tantalum precursors suitable for chemical vapor deposition of tantalum-containing material, e.g., tantalum, TaN, TaSiN, etc., on substrates. The tantalum precursors are substituted cyclopentadienyl tantalum compounds. In one aspect of the invention, such compounds are silylated to constitute tantalum/silicon source reagents. The precursors of the invention are advantageously employed in semiconductor manufacturing applications to form diffusion barriers in connection with copper metallization of the semiconductor device structure.

Claims (79)

1. A compound of the formula:

wherein:

n is an integer having a value of from 1 to 5;

each R can be the same or different and each is independently selected fr re the group consisting of D, H, CH 3 , C 2 H 5 , i-C 3 H 7 , C 4 H 9 and Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl; and

each of R′ can be the same or different and each is independently selected f in the group consisting of D, H, C 1 -C 4 alkyl, and Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl;

with the provisos that (i) each of the R groups and R′ are not simultaneously all H, and (ii) when each of R′ is H, and n is 1, both R groups are not simultaneously trimethylsilyl.

2. The compound of claim 1 , wherein at least one of R, R′ is Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl.

3. The compound of claim 1 , wherein at least one of R, R′ is trimethysilyl.

4. The compound of claim 1 , wherein n is 1 for each cyclopentadienyl ring.

5. The compound of claim 4 , wherein R on each cyclopentadienyl ring is trimethylsilyl.

6. The compound of claim 1 , wherein each of the R group and R are independently selected from H, methyl, isopropyl, t-butyl, trimethylsilyl, and t-butylsilyl.

7. The compound of claim 6 , wherein at least one of the R groups and R′ is trimethylsilyl.

8. The compound of claim 7 , wherein n is 1 for each cyclopentadienyl ring.

9. The compound of claim 8 , wherein R on each cyclopentadienyl ring is trimethylsilyl.

10. The compound of claim 1 , wherein each of the R group and R′ are independently selected from H and Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl.

11. The compound of claim 10 , wherein n is 1 for each cyclopentadienyl ring.

12. The compound of claim 11 , wherein R on each cyclopentadienyl ring is trimethysilyl.

13. The compound of claim 11 , wherein each R is H.

14. The compound of claim 13 , wherein at least one of R′ is Si(R″) wherein each R″ is independently selected from H and C 1 -C 4 alkyl.

15. The compound of claim 14 , wherein one of R 1 , R 2 and R 3 is Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl.

16. The compound of claim 15 , wherein Si(R″) 3 is alkylsilyl.

17. The compound of claim 16 , wherein said alkylsilyl is t-butylsilyl.

18. A compound of the formula:

wherein TMS is trimethylsilyl and R′ is selected from the group consisting of D, C 1 -C 4 alkyl, and Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl.

19. A compound of the formula:

20. A method of forming a tantalum-containing material in a substrate, comprising contacting the substrate with a vapor of a tantalum precursor under chemical vapor deposition conditions, wherein said tantalum precursor comprises a compound of the formula:

wherein:

n is an integer having a value of from 1 to 5;

each R can be the same or different and each is independently selected from the group consisting of D, H, CH 3 , C 2 H 5 , i-C 3 H 7 , C 4 H 9 and Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl; and

each of R′ can be the same or different and each is independently selected from the group consisting of D, H, C 1 -C 4 alkyl, and Si(R″) 3 wherein each R″ is independently elected from H and C 1 -C 4 alkyl.

with the provisios that (i) each of the R groups and R′ are not simultaneously all H, and (ii) when each of R′ is H, and n is 1, both R groups are not simultaneously trimethylsilyl.

21. The method of claim 20 , wherein at least one of R′ is Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl.

22. The method of claim 20 , wherein at least one of R,R′ is trimethysilyl.

23. The method of claim 20 , wherein n is 1 for each cyclopentadienyl ring.

24. The method of claim 23 , wherein R on each cyclopentadienyl ring is trimethylsilyl.

25. The method of claim 20 , wherein each of the R group and R′ are independently selected from H, methyl, isopropyl, t-butyl, trimethylsilyl, and t-butylsilyl.

26. The method of claim 25 , wherein at least one of the R group and R′ is trimethylsilyl.

27. The method of claim 26 , wherein n is 1 for each cyclopentadienyl ring.

28. The method of claim 27 , wherein R on each cyclopentadienyl ring is trimethylsilyl.

29. The method of claim 20 , wherein each of the R group and R′ are independently selected from H and Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl.

30. The method of claim 29 , wherein n is 1 for each cyclopentadienyl ring.

31. The method of claim 30 , wherein R on each cyclopentadienyl ring is trimethylsilyl.

32. The method of claim 30 , wherein each R is H.

33. The method of claim 32 , wherein at least one of R′ is Si(R″), wherein each R″ is independently selected from H and C 1 -C 4 alkyl.

34. The method of claim 33 , wherein one of R′ is Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl.

35. The method of claim 34 , wherein Si(R″) 3 is alkylsilyl.

36. The method of claim 35 , wherein said alkylsilyl is t-butylsilyl.

37. The method of claim 20 , wherein said precursor comprises:

wherein TMS is trimethylsilyl and R′ is selected from the group consisting of D, C 1 -C 4 alkyl, and Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl.

38. The method of claim 20 , wherein said precursor comprises:

39. The method of claim 20 , wherein the substrate comprises a semiconductor substrate.

40. The method of claim 20 , wherein the substrate comprises a microelectronic device structure.

41. The method of claim 20 , wherein the tantalum-containing material comprises a silicon-doped tantalum material.

42. The method of claim 20 , wherein said chemical vapor deposition conditions comprise a nitrogen atmosphere.

43. The method of claim 20 , wherein said tantalum-containing material comprises TaN.

44. The method of claim 43 , wherein said chemical vapor deposition conditions comprise a nitrogen source for nitrogen in said TaN.

45. The method of claim 20 , wherein said tantalum-containing material comprises TaSiN.

46. The method of claim 45 , wherein said chemical vapor deposition conditions comprise a nitrogen source for nitrogen in said TaSiN.

47. The method of claim 20 , wherein said substrate is a semiconductor substrate, and the tantalum-containing material comprises a material selected from the group consisting of TaN and TaSiN.

48. The method of claim 47 , wherein the tantalum-containing material forms a diffusion barrier layer for copper metallization on said substrate.

49. The method of claim 48 , wherein said copper metallization on said substrate has a line dimension of less than about 0.18 μm.

50. A method of synthesizing a cyclopentadienyl tantalum compound of the formula [(R) n Cp] 2 Ta(R′) 3

wherein:

n is an integer having a value of from 1 to 5;

each R can be the same or different and each is independently selected from the group consisting of D, H, CH 3 , C 2 H 5 , i-C 3 H 7 , C 4 H 9 and Si(R″) 3 wherein each R″ is independently selected from H and C 1 -C 4 alkyl; and

each of R′ can be the same or different and each is independently selected in the group consisting of D, H, C 1 -C 4 alkyl, and Si(R″) 3 wherein each R″ is independently elected from H and C 1 -C 4 alkyl;

with the proviso that each of the R groups and R′ are not simultaneously all H,

said method comprising

reacting tantalum pentachioride with a cyclopentadienyllithium compound of the formula [(R) n Cp] 2 Li in a 1:2 ratio and stepwise addition of sodium borohydride compound of the formula NaBH(R′) 3 to yield said cyclopentadienyl tantalum compound according to the following formula:

51. The method of claim 50 , wherein said reacting step is conduct in a protic solvent medium.

52. The method of claim 51 , wherein said protic solvent medium comprises tetrahydrofuran.

53. The method of claim 50 , wherein said cyclopentadienyl tantalum compound is:

wherein TMS is trimethylsilyl.

54. The method of claim 50 , further comprising reacting said cyclopentadienyl tantalum compound with a silane form a cyclopentadienylsilyltantalum compound.

55. The method of claim 54 , wherein said silane comprises an alkylsiane.

56. The method of claim 55 , wherein said alkylsilane comprises t-butysilane.

57. The method of claim 54 , wherein said cyclopentadienylsilyltantalum compound comprises:

wherein TMS is trimethylsilyl.

58. The method of claim 54 , wherein said cyclopentadienylsilyltantalum compound comprises:

Assignments (9)
SECURITY INTEREST Recorded Jul 8, 2022
From: ENTEGRIS, INC.; ENTEGRIS GP, INC.; POCO GRAPHITE, INC.; CMC MATERIALS, INC.; INTERNATIONAL TEST SOLUTIONS, LLC; QED TECHNOLOGIES INTERNATIONAL, INC.
To: TRUIST BANK, AS NOTES COLLATERAL AGENT
Reel/Frame 060613/0072 →
ASSIGNMENT OF PATENT SECURITY INTEREST RECORDED AT REEL/FRAME 048811/0679 Recorded Nov 5, 2019
From: GOLDMAN SACHS BANK USA
To: MORGAN STANLEY SENIOR FUNDING, INC.
Reel/Frame 050965/0035 →
SECURITY INTEREST Recorded Nov 13, 2018
From: ENTEGRIS, INC.; SAES PURE GAS, INC.
To: GOLDMAN SACHS BANK USA
Reel/Frame 048811/0679 →
RELEASE OF SECURITY INTEREST Recorded Nov 8, 2018
From: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
To: ENTEGRIS, INC.; POCO GRAPHITE, INC.; ATMI, INC.; ATMI PACKAGING, INC.; ADVANCED TECHNOLOGY MATERIALS, INC.
Reel/Frame 047477/0032 →
RELEASE OF SECURITY INTEREST Recorded Nov 8, 2018
From: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
To: ENTEGRIS, INC.; POCO GRAPHITE, INC.; ATMI, INC.; ATMI PACKAGING, INC.; ADVANCED TECHNOLOGY MATERIALS, INC.
Reel/Frame 047477/0151 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2015
From: ADVANCED TECHNOLOGY MATERIALS, INC.
To: ENTEGRIS, INC.
Reel/Frame 034894/0025 →
SECURITY INTEREST Recorded May 2, 2014
From: ENTEGRIS, INC.; POCO GRAPHITE, INC.; ATMI, INC.; ADVANCED TECHNOLOGY MATERIALS, INC.; ATMI PACKAGING, INC.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 032812/0192 →
SECURITY INTEREST Recorded May 1, 2014
From: ENTEGRIS, INC.; POCO GRAPHITE, INC.; ATMI, INC.; ADVANCED TECHNOLOGY MATERIALS, INC.; ATMI PACKAGING, INC.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 032815/0852 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 28, 2003
From: KAMEPALLI, SMURUTHI; BAUM, THOMAS H.
To: ADVANCED TECHNOLOGY MATERIALS, INC.
Reel/Frame 013995/0256 →