Additives to prevent degradation of cyclic alkene derivatives

• US 7,931,823 B2
• Filed: 09/12/2006
• Issued: 04/26/2011
• 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.
• Primary Examiner(s): ANTHONY, JOSEPH DAVID
• Application Number:
  US11/519,579
• Publication Number:
  US 20070057235A1
• Time in Patent Office: 1,687 Days
• Field of Search: 443/12, 444/42, 444/43, 444/45, 252/182.29
• US Class Current: 252/182.29
• CPC Class Codes: C07C 13/00 Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
• CPC Class Codes: C07C 13/64 with a bridged ring system
• 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

Abstract

A stabilized cyclic alkene composition comprising one or more cyclic alkenes, and at least one antioxidant compound having the formula (I),

wherein R¹ through R⁵ can each independently be H, OH, C₁-C₈ linear, branched, or cyclic alkyl, C₁-C₈ linear, branched, or cyclic alkoxy or substituted or unsubstituted aryl, and wherein the antioxidant compound is present in an amount between 1 ppm and 200 ppm and has a boiling point lower than 265° C. A method for forming a layer of carbon-doped silicon oxide on a substrate, which uses the stabilized alkene composition and a silicon containing compound.

Claims

1. A composition, comprising:

one or more cyclic alkenes, and

at least one antioxidant compound of Formula (I),

2. The composition of claim 1, wherein the antioxidant compound is at least one compound selected from the group consisting of:

phenol, 4-methylphenol, 3-methylphenol, 2-methylphenol, 4-ethylphenol, 4-propylphenol, 4-isopropylphenol, 4-butylphenol, 4-sec-butylphenol, 4-iso-butylphenol, 4-tert-butylphenol, 4-methoxyphenol, 3-methoxyphenol, 2-methoxyphenol, 4-ethoxyphenol, 2-(1-methylbutyl)phenol, 2-tert-butyl-6-methylphenol, and 1,2-dihydroxybenzene.

3. The composition of claim 2, wherein the antioxidant compound is 4-methoxyphenol.

4. The composition of claim 1, wherein the antioxidant compound is present in an amount between about 1 ppm to about 100 ppm.

5. The composition of claim 1, wherein the antioxidant compound is present in a concentration between about 100 ppm and about 200 ppm.

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

2x−

yR_y, wherein n is an integer from 4 to 18, x is an integer where 1≦

x≦

n/2, y is an integer wherein 0≦

y≦

2n−

2x, and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated, or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated, or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

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

(2x+2)−

yR_y, wherein n is an integer from 5 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

y≦

2n−

(2x+2), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

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

(2x+4)−

1R_y, wherein n is an integer from 7 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

y≦

2n−

(2x+4), R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

9. 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.

10. 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, and wherein the antioxidant compound is 4-methoxyphenol.

28. The composition of claim 1, wherein one of R¹ through R⁵ is OH.

29. The composition of claim 1, wherein R¹ is OH.

30. The composition of claim 1, wherein the antioxidant compound is 1,2-dihydroxybenzene.

11. A method for stabilizing a cyclic alkene, comprising combining at least one antioxidant compound of formula (I):

12. The method of claim 11, wherein the antioxidant compound is at least one compound selected from the group consisting of:

phenol, 4-methylphenol, 3-methylphenol, 2-methylphenol, 4-ethylphenol, 4-propylphenol, 4-isopropylphenol, 4-butylphenol, 4-sec-butylphenol, 4-iso-butylphenol, 4-tert-butylphenol, 4-methoxyphenol, 3-methoxyphenol, 2-methoxyphenol, 4-ethoxyphenol, 2-(1-methylbutyl)phenol, 2-tert-butyl-6-methylphenol, and 1,2-dihydroxybenzene.

13. The method of claim 12, wherein the antioxidant compound is 4-methoxyphenol.

14. The method of claim 11, wherein the cyclic alkene has the general formula C_nH_2n−

2x−

yR_y, wherein n is an integer from 4 to 18, x is an integer where 1≦

x≦

n/2, y is an integer wherein 0≦

y≦

2n−

2x, and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated, or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated, or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

15. The method of claim 11, wherein the cyclic alkene has the general formula C_nH_2n−

(2x+2)−

yR_y, wherein n is an integer from 5 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

y≦

2n−

(2x+2), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

16. The method of claim 11, wherein the cyclic alkene has the general formula C_nH_2n−

(2x+4)−

yR_y, wherein n is an integer from 7 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

y≦

2n−

(2x+4), R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

17. The method of claim 11, 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.

18. The method of claim 11, 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, and wherein the antioxidant compound is 4-methoxyphenol.

31. The method of claim 11, wherein one of R¹ through R⁵ is OH.

32. The method of claim 11, wherein R¹ is OH.

33. The method of claim 11, wherein the antioxidant compound is 1,2-dihydroxybenzene.

19. A method of forming a layer of carbon-doped silicon oxide on a substrate, the method comprising the steps of:

providing a cyclic alkene composition, a silicon containing compound, and a substrate; and

forming the layer of the carbon-doped silicon oxide on the substrate,

wherein the cyclic alkene composition comprises;

one or more cyclic alkenes; and

at least one antioxidant compound of formula (I);

20. The method of claim 19, further comprising the steps of:

providing the cyclic alkene composition in a first container, the silicon containing compound in a second container, a film deposition tool, a 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 a connection into the film deposition chamber, wherein the substrate is disposed within the film deposition chamber of the film deposition tool;

connecting the first and second containers to the film deposition chamber within the film deposition tool;

introducing vapors of the cyclic alkene composition and the silicon containing compound into the carrier gas stream; and

transporting the vapors of the cyclic alkene composition and the silicon containing compound into the film deposition chamber.

21. The method of claim 20, wherein the cyclic alkene has the general formula C_nH_2n−

2x−

yR_y, wherein n is an integer from 4 to 18, x is an integer where 1≦

x≦

n/2, y is an integer wherein 0≦

y≦

2n−

2x, and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated, or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated, or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

22. The method of claim 20, wherein the cyclic alkene has the general formula C_nH_2n−

(2x+2)−

yR_y, wherein n is an integer from 5 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

y≦

2n−

(2x+2), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

23. The method of claim 20, wherein the cyclic alkene has the general formula C_nH_2n−

(2x+4)−

yR_y, wherein n is an integer from 7 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

y≦

2n−

(2x+4), R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

24. The method of claim 20, 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.

25. The method of claim 20, wherein the antioxidant compound is at least one compound selected from the group consisting of:

phenol, 4-methylphenol, 3-methylphenol, 2-methylphenol, 4-ethylphenol, 4-propylphenol, 4-isopropylphenol, 4-butylphenol, 4-sec-butylphenol, 4-iso-butylphenol, 4-tertbutylphenol, 4-methoxyphenol, 3-methoxyphenol, 2-methoxyphenol, 4-ethoxyphenol, 2-(1-methylbutyl)phenol, 2-tert-butyl-6-methylphenol, 1,2-dihydroxybenzene.

26. The method of claim 25, wherein the antioxidant compound is 4-methoxyphenol.

27. The method of claim 20, 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, and wherein the antioxidant compound is 4-methoxyphenol.

34. The method of claim 19, wherein one of R¹ through R⁵ is OH.

35. The method of claim 19, wherein R¹ is OH.

36. The method of claim 19, wherein the antioxidant compound is 1,2-dihydroxybenzene.

37. A composition, comprising:

one or more cyclic alkenes selected from the group consisting of phellandrene, alpha-terpinene, gamma-terpinene, alpha-pinene, 3-carene, terpinolene, norbornene, norbornadiene, 5-vinyl-2-norbornene, and 5-ethylidene-2-norbornene, and

at least one antioxidant compound of Formula (I),

38. The composition of claim 37, wherein R¹ is OH.

39. The composition of claim 37, wherein the antioxidant compound is 1,2-dihydroxybenzene, 1,3-dihydroxybenzene, hydroquinone, or 3-tert-butyl-1,2-dihydroxybenzene.

40. A method for stabilizing a cyclic alkene, comprising combining the cyclic alkene with at least one antioxidant compound of formula (I):

41. The method of claim 40, wherein R¹ is OH.

42. The method of claim 40, wherein the antioxidant compound is 1,2-dihydroxybenzene, 1,3-dihydroxybenzene, hydroquinone, or 3-tert-butyl-1,2-dihydroxybenzene.

43. A method of forming a layer of carbon-doped silicon oxide on a substrate, the method comprising the steps of:

providing a cyclic alkene composition, a silicon containing compound, and a substrate; and

forming the layer of the carbon-doped silicon oxide on the substrate, wherein the cyclic alkene composition comprises;

one or more cyclic alkenes selected from the group consisting of phellandrene, alpha-terpinene, gamma-terpinene, alpha-pinene, 3-carene, terpinolene, norbornene, norbornadiene, 5-vinyl-2-norbornene, and 5-ethylidene-2-norbornene; and

at least one antioxidant compound of formula (I);

44. The method of claim 43, wherein R¹ is OH.

45. The method of claim 43, wherein the antioxidant compound is 1,2-dihydroxybenzene, 1,3-dihydroxybenzene, hydroquinone, or 3-tert-butyl-1,2-dihydroxybenzene.

46. A composition, comprising:

one or more cyclic alkenes 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

at least one antioxidant compound of Formula (I),

47. The composition of claim 46, wherein R¹ is OH.

48. The composition of claim 46, wherein the antioxidant compound is 1,2-dihydroxybenzene.

49. A method for stabilizing a cyclic alkene, comprising combining the cyclic alkene with at least one antioxidant compound of formula (I):

50. The method of claim 49, wherein R¹ is OH.

51. The method of claim 49, wherein the antioxidant compound is 1,2-dihydroxybenzene.

52. A method of forming a layer of carbon-doped silicon oxide on a substrate, the method comprising the steps of:

providing a cyclic alkene composition, a silicon containing compound, and a substrate; and

forming the layer of the carbon-doped silicon oxide on the substrate,

wherein the cyclic alkene composition comprises;

one or more cyclic alkenes 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

at least one antioxidant compound of formula (I);

53. The method of claim 52, wherein R¹ is OH.

54. The method of claim 52, wherein the antioxidant compound is 1,2-dihydroxybenzene.