Additives to Prevent Degradation of Cyclic Alkene Derivatives

• US 20090291210A1
• Filed: 07/07/2009
• Published: 11/26/2009
• Est. Priority Date: 09/12/2005
• Status: Active Grant

• Current Assignee: Fujifilm Electronic Materials USA Incorporated (Fujifilm Holdings Corporation)
• Original Assignee: Fujifilm Electronic Materials USA Incorporated (Fujifilm Holdings Corporation)
• Inventors: Chagolla, John L., Teff, Daniel J.
• Granted Patent: US 7,871,536 B2
• Time in Patent Office: Days
• US Class Current: 427/255.6
• CPC Class Codes: C07C 13/20 with a cyclohexene ring
• CPC Class Codes: C07C 13/21 Menthadienes
• CPC Class Codes: C07C 13/23 with a cyclohexadiene ring
• CPC Class Codes: C07C 13/39 with a bicyclo ring system containing seven carbon atoms
• CPC Class Codes: C07C 13/42 with a bicycloheptene ring structure
• CPC Class Codes: C07C 13/43 substituted by unsaturated acyclic hydrocarbon
• CPC Class Codes: C07C 13/61 with a bridged indene ring, e.g. dicyclopentadiene
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 2602/42 the bicyclo ring system containing seven carbon atoms
• CPC Class Codes: C07C 2603/68 Dicyclopentadienes; Hydrogenated dicyclopentadienes
• CPC Class Codes: C07C 39/04 Phenol
• CPC Class Codes: C07C 39/06 Alkylated phenols
• CPC Class Codes: C07C 7/20 Use of additives, e.g. for stabilisation
• CPC Class Codes: C09K 15/08 containing a phenol or quinone moiety
• CPC Class Codes: C23C 16/401 containing silicon
• CPC Class Codes: C23C 16/448 characterised by the method used for generating reactive gas streams, e.g. by evaporation or sublimation of precursor materials
• CPC Class Codes: H10K 71/15 characterised by the solvent used

Abstract

This disclosure relates to compositions that includes (a) one or more substituted or unsubstituted cyclic alkenes, and (b) an antioxidant composition including at least one compound of Formula (I):

R¹ through R⁴ in Formula (I) are described in the specification.

Claims

1. A composition, comprising:

(a) one or more substituted or unsubstituted cyclic alkenes, and

(b) an antioxidant composition comprising at least one compound of Formula (I),

2. The composition of claim 1, wherein one of R¹ through R⁴ is methyl, ethyl, methoxy, or ethoxy.

3. The composition of claim 2, wherein at least one of the remaining R¹ through R⁴ is H.

4. The composition of claim 2, wherein all of the remaining R¹ through R⁴ are H.

5. The composition of claim 1, wherein R² or R³ is methyl or methoxy.

6. The composition of claim 5, wherein at least one of the remaining R¹ through R⁴ are H.

7. The composition of claim 1, wherein the antioxidant composition comprises 4-methyl-1,2-dihydroxybenzene.

8. The composition of claim 1, wherein the antioxidant composition comprises 3-methoxy-1,2-dihydroxybenzene.

9. The composition of claim 1, wherein the antioxidant composition is present in a concentration between about 1 ppm and about 200 ppm.

10. The composition of claim 1, wherein the antioxidant composition is present in a concentration between about 50 ppm and about 150 ppm.

11. The composition of claim 1, wherein the cyclic alkene has the general formula C_nH_2n-2x-yR_y, in which n is an integer from 4 to 18, x is an integer and 1≦

x≦

n/2, y is an integer and 0≦

y≦

2n−

2x, and each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent.

12. The composition of claim 1, wherein the cyclic alkene has the general formula C_nH_2n−

(2x+2)−

yR_y, in which n is an integer from 5 to 18, x is an integer and x≦

n/2, y is an integer and 0≦

y≦

2n−

(2x+2), and each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent.

13. The composition of claim 1, wherein the cyclic alkene has the general formula C_nH_2n−

(2x+4)−

yR_y, in which n is an integer from 7 to 18, x is an integer and x≦

n/2, y is an integer and 0≦

y≦

2n−

(2x+4), each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent.

14. The composition of claim 1, wherein the cyclic alkene is at least one compound selected from the group consisting of dipentene, phellandrene, dicyclopentadiene, alpha-terpinene, gamma-terpinene, limonene, alpha-pinene, 3-carene, terpinolene, norbornene, norbornadiene, 5-vinyl-2-norbornene, and 5-ethylidene-2-norbornene.

15. The composition of claim 1, wherein at least one of R¹ through R⁴ is not H, or if one of R¹ through R⁴ is t-butyl, at least one of the remaining R¹ through R⁴ is not H.

16. A process, comprising treating a substrate in a film deposition chamber with at least one cyclic alkene composition and at least one silicon containing compound to form a carbon doped silicon oxide film on the substrate,

wherein the cyclic alkene composition comprises:

(a) one or more substituted or unsubstituted cyclic alkenes, and

(b) an antioxidant composition comprising at least one compound of Formula (I),

17. The process of claim 16, further comprising, prior to the treatment step, providing the cyclic alkene composition in a first container, the silicon containing compound in a second container, a film deposition tool containing the film deposition chamber, a connector configured to connect the first and second containers to the film deposition chamber within the film deposition tool, and a stream of carrier gas to sweep the cyclic alkene composition and the silicon containing compound through the connector into the film deposition chamber.

18. The process of claim 17, further comprising, prior to the treatment step, introducing vapors of the cyclic alkene composition and the silicon containing compound into the carrier gas stream.

19. The process of claim 18, further comprising, prior to the treatment step, transporting the vapors of the cyclic alkene composition and silicon containing compound into the film deposition chamber via the carrier gas stream.

20. The process of claim 16, wherein one of R¹ through R⁴ is methyl, ethyl, methoxy, or ethoxy.

21. The process of claim 20, wherein at least one of the remaining R¹ through R⁴ is H.

22. The process of claim 21, wherein all of the remaining R¹ through R⁴ are H.

23. The process of claim 16, wherein R² or R³ is methyl or methoxy.

24. The process of claim 23, wherein at least one of the remaining R¹ through R⁴ is H.

25. The process of claim 16, wherein the antioxidant composition comprises 4-methyl-1,2-dihydroxybenzene.

26. The process of claim 16, wherein the antioxidant composition comprises 3-methoxy-1,2-dihydroxybenzene.

27. The process of claim 16, wherein the antioxidant composition is present in a concentration between about 1 ppm and about 200 ppm.

28. The process of claim 16, wherein the antioxidant composition is present in a concentration between about 50 ppm and about 150 ppm.

29. The process of claim 16, wherein the cyclic alkene has the general formula C_nH_2n-2x-yR_y, in which n is an integer from 4 to 18, x is an integer and 1≦

x≦

n/2, y is an integer and 0≦

y≦

2n−

2x, and each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent.

30. The process of claim 16, wherein the cyclic alkene has the general formula C_nH_2n−

(2x+2)−

yR_y, in which n is an integer from 5 to 18, x is an integer and x≦

n/2, y is an integer and 0≦

y≦

2n−

(2x+2), and each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent.

31. The process of claim 16, wherein the cyclic alkene has the general formula C_nH_2n−

(2x+2)−

yR_y, in which n is an integer from 7 to 18, x is an integer and x≦

n/2, y is an integer and 0≦

y≦

2n−

(2x+4), each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent.

32. The process of claim 16, wherein the cyclic alkene is at least one compound selected from the group consisting of dipentene, phellandrene, dicyclopentadiene, alpha-terpinene, gamma-terpinene, limonene, alpha-pinene, 3-carene, terpinolene, norbornene, norbornadiene, 5-vinyl-2-norbornene, and 5-ethylidene-2-norbornene.

33. The process of claim 16, wherein at least one of R¹ through R⁴ is not H, or if one of R¹ through R⁴ is t-butyl, at least one of the remaining R¹ through R⁴ is not H.

34. A composition, comprising:

(a) a cyclic alkene selected from the group consisting of dipentene, phellandrene, dicyclopentadiene, alpha-terpinene, gamma-terpinene, limonene, alpha-pinene, 3-carene, terpinolene, norbornene, norbornadiene, 5-vinyl-2-norbornene, and 5-ethylidene-2-norbornene, and

(b) an antioxidant composition comprising 4-methyl-1,2-dihydroxybenzene or 3-methoxy-1,2-dihydroxybenzene,

wherein the antioxidant composition is present in a concentration between about 50 ppm and about 150 ppm.

35. The composition of claim 34, wherein the antioxidant composition comprises 4-methyl-1,2-dihydroxybenzene.

36. The composition of claim 34, wherein the antioxidant composition is present in a concentration of about 100 ppm.

37. A process, comprising treating a substrate in a film deposition chamber with at least one cyclic alkene composition and at least one silicon containing compound to form a carbon doped silicon oxide film on the substrate,

wherein the cyclic alkene composition comprises:

(a) a cyclic alkene selected from the group consisting of dipentene, phellandrene, dicyclopentadiene, alpha-terpinene, gamma-terpinene, limonene, alpha-pinene, 3-carene, terpinolene, norbornene, norbornadiene, 5-vinyl-2-norbornene, and 5-ethylidene-2-norbornene, and

(b) an antioxidant composition comprising 4-methyl-1,2-dihydroxybenzene or 3-methoxy-1,2-dihydroxybenzene,

wherein the antioxidant composition is present in a concentration between about 50 ppm and about 150 ppm.

38. An apparatus, comprising:

a sealed container comprising a cyclic alkene composition, the cyclic alkene composition comprising

(a) at least one substituted or unsubstituted cyclic alkene, and

(b) at least one antioxidant composition,

wherein the cyclic alkene composition generates at most about 200 ppm of residue after one year of storage in the sealed container at room temperature.

39. The apparatus of claim 38, wherein the cyclic alkene composition generates at most about 100 ppm of residue after one year of storage in a sealed container at room temperature.

40. An apparatus, comprising:

a sealed container comprising from about 0 ppm to about 150 ppm oxygen and a cyclic alkene composition, the composition comprising

(a) at least one substituted or unsubstituted cyclic alkene, and

(b) at least one antioxidant composition,

wherein the cyclic alkene composition generates at most about 20 ppm of residue after being heated at 80°

C. for 12 hours in the sealed container.

41. The apparatus of claim 40, wherein the sealed container comprises about 150 ppm oxygen and the cyclic alkene composition generates at most about 20 ppm of residue after being heated at 80°

C. for 12 hours in the sealed container.

42. The apparatus of claim 40, wherein the sealed container comprises about 25 ppm oxygen and the cyclic alkene composition generates at most about 5 ppm of residue after being heated at 80°

C. for 12 hours in the sealed container.

43. The apparatus of claim 40, wherein the sealed container comprises about 0 ppm oxygen and the cyclic alkene composition generates at most about 5 ppm of residue after being heated at 80°

C. for 12 hours in the sealed container.

44. A process, comprising:

storing a cyclic alkene composition in a sealed container for at least 6 months, and

after storing the cyclic alkene composition, using the cyclic alkene composition together with at least one silicon-containing compound in a chemical vapor deposition process to form a carbon doped silicon oxide film on a substrate,

wherein the cyclic alkene composition comprises;

(a) one or more substituted or unsubstituted cyclic alkenes, and

(b) an antioxidant composition comprising at least one compound of Formula (I),

45. A process for stabilizing a cyclic alkene, comprising:

adding at least one compound of Formula (I) to the cyclic alkene,

46. The process of claim 45, wherein adding at least one compound of Formula (I) comprises (a) adding the at least one compound of Formula (I) in a receiving vessel in a distillation system for purifying the cyclic alkene, and (b) distilling the cyclic alkene through the distillation system into the receiving vessel.

47. The process of claim 45, wherein adding at least one compound of Formula (I) comprises (a) adding the at least one compound of Formula (I) at a point between a condenser and a receiving vessel in a distillation system for purifying the cyclic alkene, and (b) distilling the cyclic alkene through the distillation system so that the distilled cyclic alkene passes from the condenser into the receiving vessel, thereby solubilizing the at least one compound of Formula (I) in the distilled cyclic alkene.

48. The process of claim 45, wherein adding at least one compound of Formula (I) comprises (a) distilling the cyclic alkene through a distillation system into a receiving vessel, and (b) adding the at least one compound of Formula (I) into the receiving vessel.