CYCLIC AMINO COMPOUNDS FOR LOW-K SILYLATION

• US 20100233829A1
• Filed: 03/10/2010
• Published: 09/16/2010
• Est. Priority Date: 03/10/2009
• Status: Active Grant

• Current Assignee: American Air Liquide Incorporated (L'Air Liquide SA)
• Original Assignee: American Air Liquide Incorporated (L'Air Liquide SA)
• Inventors: McANDREW, James J.F., Anderson, Curtis, Dussarrat, Christian
• Granted Patent: US 8,999,734 B2
• Time in Patent Office: Days
• US Class Current: 438/4
• CPC Class Codes: C07F 7/10 containing nitrogen having a Si-N linkage
• CPC Class Codes: H01L 21/02343 treatment by exposure to a liquid
• CPC Class Codes: H01L 21/02359 treatment to change the surface groups of the insulating layer

Abstract

Disclosed herein are mono-functional silylating compounds that may exhibit enhanced silylating capabilities. Also disclosed are method of synthesizing and using these compounds. Finally methods to determine effective silylation are also disclosed.

Claims

1. A silylation compound of the formula R₃SiL, wherein each R is independently selected from the group consisting of H, methyl, and ethyl;

L is a nitrogen-containing ring selected from the group consisting of 1,2,3-triazole, piperidine, 1-methylpiperazine, pyrrolidine, and pyrazole; and

one nitrogen in the nitrogen-containing ring is bonded directly to the Si atom; and

a total concentration of metal contaminants in the compound is less than 10 ppmw.

2. The silylation compound of claim 1, wherein the compound is selected from the group consisting of trimethylsilylpyrrolidine, trimethylsilylpyrazole, trimethylsilyl-1,2,3-triazole, trimethylsilylpiperidine, and trimethylsilyl-4-methylpiperazine.

3. The silylation compound of claim 2, wherein the total concentration of metal contaminants is less than 1 ppmw.

4. The silylation compound of claim 1, further comprising a boiling point of less than approximately 200°

C.

5. The silylation compound of claim 4, wherein the boiling point is between approximately 100°

C. and approximately 200°

C.

6. A silylation chemistry delivery device comprising:

a canister having an inlet conduit and an outlet conduit and containing a silylating agent having a formula R₃SiL, wherein each R is independently selected from the group consisting of H, methyl, and ethyl;

L is a nitrogen-containing ring selected from the group consisting of 1,2,3-triazole, piperidine, 1-methylpiperazine, pyrrolidine, and pyrazole; and

one nitrogen in the nitrogen-containing ring is bonded directly to the Si atom.

7. The silylation chemistry delivery device of claim 6, wherein the silylating agent has a total concentration of metal contaminants of less than 10 ppmw.

8. The silylation chemistry delivery device of claim 7, wherein the silylating agent is selected from the group consisting of trimethylsilylpyrrolidine, trimethylsilylpyrazole, trimethylsilyl-1,2,3-triazole, trimethylsilylpiperidine, and trimethylsilyl-4-methylpiperazine.

9. The silylation chemistry deliver device of claim 6, wherein an end of the inlet conduit end is located above a surface of the silylating agent and an end of the outlet conduit is located below the surface of the silylating agent.

10. The silylation chemistry deliver device of claim 6, wherein an end of the inlet conduit end is located below a surface of the silylating agent and an end of the outlet conduit is located above the surface of the silylating agent.

11. A method of repairing a dielectric film, the method comprising the steps of:

Introducing the dielectric film into a chamber;

Introducing into the chamber a repair agent having a formula R₃SiL, wherein each R is independently selected from the group consisting of H, methyl, and ethyl;

L is a nitrogen-containing ring selected from the group consisting of 1,2,3-triazole, piperidine, 1-methylpiperazine, pyrrolidine, and pyrazole; and

one nitrogen in the nitrogen-containing ring is bonded directly to the Si atom; and

Contacting the repair agent and the dielectric film.

12. The method of claim 11, further comprising heating the dielectric film after introduction into the chamber and prior to introduction of the repair agent.

13. The method of claim 11, further comprising allowing the repair agent to react with the dielectric film for a suitable length of time following the contacting step.

14. The method of claim 13, further comprising annealing the dielectric film following the repair agent reaction step.

15. The method of claim 11, wherein the repair agent is selected from the group consisting of trimethylsilylpyrrolidine, trimethylsilylpyrazole, trimethylsilyl-1,2,3-triazole, trimethylsilylpiperidine, and trimethylsilyl-4-methylpiperazine.

16. The method of claim 15, wherein the repair agent has a total concentration of metal contaminants of less than 10 ppmw.