Use of water and acidic water to purify liquid MOCVD precursors
First Claim
Patent Images
1. In a process for the removal of β
- -diketone byproducts from a reaction mixture containing a monovalent copper β
-diketone complex product prepared by reacting a reactive copper compound with an H form or K form of a fluorinated β
-diketone and, optionally, a stabilizing organic ligand (L), contaminated with the unreacted H form or K form fluorinated β
-diketone and a divalent copper β
-diketone complex byproduct, the improvement for removing the unreacted H form or K form fluorinated β
-diketone from the reaction mixture which comprises;
contacting the reaction mixture with an effective amount of double deionized water for solubilizing the H form or K form fluorinated β
-diketone;
forming an aqueous phase containing the H form or K form fluorinated β
-diketone and an organic phase containing the monovalent copper β
-diketone complex product;
separating the aqueous phase from the organic phase; and
, recovering the monovalent copper β
-diketone complex product.
2 Assignments
0 Petitions
Accused Products
Abstract
This invention relates to an improvement in a purification process for producing those liquid copper based complexes of β-diketones and, particularly the monovalent copper complexes of β-diketones, which are suited for application by chemical vapor deposition in the electronics industry. In the basic process for preparing a copper based complex, a reactive copper compound is reacted with a fluorinated β-diketonate and an organo source such as an olefinic source or one having acetylenic unsaturation. Purification is effected by contacting reaction product with a double deionized deoxygenated water source and preferably an acid/water source. An aqueous layer and an organic layer are formed with the aqueous layer containing byproducts and the organic phase containing product.
-
Citations
30 Claims
-
1. In a process for the removal of β
- -diketone byproducts from a reaction mixture containing a monovalent copper β
-diketone complex product prepared by reacting a reactive copper compound with an H form or K form of a fluorinated β
-diketone and, optionally, a stabilizing organic ligand (L), contaminated with the unreacted H form or K form fluorinated β
-diketone and a divalent copper β
-diketone complex byproduct, the improvement for removing the unreacted H form or K form fluorinated β
-diketone from the reaction mixture which comprises;contacting the reaction mixture with an effective amount of double deionized water for solubilizing the H form or K form fluorinated β
-diketone;
forming an aqueous phase containing the H form or K form fluorinated β
-diketone and an organic phase containing the monovalent copper β
-diketone complex product;
separating the aqueous phase from the organic phase; and
,recovering the monovalent copper β
-diketone complex product.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30)
- -diketone byproducts from a reaction mixture containing a monovalent copper β
-
5. The process of claim 4 wherein L is the anion of the β
- -diketone selected from the group consisting of 1,1,1,5,5,5-hexafluoro-2,4-pentanedione;
4-(2,2,2-trifluoroethyl)imino-1, 1,1 ,5,5,5-hexafluoro-2-pentanone;
5-(2,2,2-trifluoroethyl)imino-1,1,1,2,2,6,6,6-octafluoro-3-hexanone, and 6-(2,2,2-trifluoroethyl)imino-1,1,1,2,2,3,3,7,7,7, -decafluoro-4-heptanone.
- -diketone selected from the group consisting of 1,1,1,5,5,5-hexafluoro-2,4-pentanedione;
-
6. The process of claim 4 wherein the monovalent copper β
- -diketone complex product has a structural formula selected from the group consisting of;
wherein R1 and R3 are each independently C1-C8 fluoroalkyl, R2 is H, F or C1-C8 alkyl or fluoroalkyl, R4 is H, C1-C8 alkyl, or Si(R6)3, each R5 is independently H or C1-C8 alkyl and each R6 is independently phenyl or C1-C8 alkyl; and
,wherein R1 and R3 are each independently C1-C8 fluoroalkyl, R2 is H, F or C1-C8 fluoroalkyl, R4 is H, C1-C8 alkyl, or Si(R5)3, and each R5 is independently H or C1-C8 alkyl or phenyl.
- -diketone complex product has a structural formula selected from the group consisting of;
-
7. The process of claim 6 wherein the monovalent copper β
- -diketone complex product has the structural formula;
- -diketone complex product has the structural formula;
-
8. The process of claim 7 wherein R1 and R3 are trifluoromethyl.
-
9. The process of claim 8 wherein R2 is H.
-
10. The process of claim 9 wherein each R5 is H.
-
11. The process of claim 10 wherein R6 is a methyl group.
-
12. The process of claim 11 wherein R4 is H.
-
13. The process of claim 4 wherein the fluorinated β
- -ketone is 1,1,1,5,5,5-hexafluoro-2,4-pentanedione and L is trimethylvinyl silane.
-
14. The process of claim 6 wherein the monovalent copper β
- -diketone complex product has the structural formula
wherein R1 and R3 are each independently trifluoromethyl, R2 is H, R4 is H, and each R5 is independently H.
- -diketone complex product has the structural formula
-
16. The process of claim 4 wherein the solution of acid and water contains from 0.1 to 2 percent by weight acid.
-
17. The process of claim 16 wherein the acid employed in forming the solution of acid and water is selected from the group consisting of nitric acid, sulfuric acid, hydrochloric acid, hydrofluoric acid, acetic acid, and mixtures thereof.
-
18. The process of claim 1 wherein the water is degassed and deoxygenated.
-
19. The process of claim 18 wherein the water is added to the reaction mixture in an amount of from 10 to 1000 weight percent by weight of the reaction mixture.
-
20. The process of claim 18 wherein the monovalent copper β
- -diketone complex product is represented by the formula;
- -diketone complex product is represented by the formula;
-
21. The process of claim 20 wherein L is the anion of the β
- -diketone selected from the group consisting of 1,1,1,5,5,5-hexafluoro-2,4-pentanedione;
4-(2,2,2-trifluoroethyl)imino-1, 1,1,5,5,5-hexafluoro-2-pentanone;
5-(2,2,2-trifluoroethyl)imino-1,1, 1,2,2,6,6,6-octafluoro-3-hexanone, and 6-(2,2,2-trifluoroethyl)imino-1,1,1,2,2,3,3,7,7,7, -decafluoro-4-heptanone.
- -diketone selected from the group consisting of 1,1,1,5,5,5-hexafluoro-2,4-pentanedione;
-
22. The process of claim 20 wherein the monovalent copper β
- -diketone complex product has a structural formula selected from the group consisting of;
wherein R1 and R3 are each independently C1-C8 fluoroalkyl, R2 is H, F or C1-C8 alkyl or fluoroalkyl, R4 is H, C1-C8 alkyl, or Si(R6)3, each R5 is independently H or C1-C8 alkyl and each R6 is independently phenyl or C1-C8 alkyl; and
,wherein R1 and R3 are each independently C1-C8 fluoroalkyl, R2 is H, F or C1-C8 fluoroalkyl, R4 is H, C1-C8 alkyl, or Si(R5)3, and each R5 is independently H or C1-C8 alkyl or phenyl.
- -diketone complex product has a structural formula selected from the group consisting of;
-
23. The process of claim 22 wherein the monovalent copper β
- -diketone complex product has the structural formula;
- -diketone complex product has the structural formula;
-
24. The process of claim 23 wherein R1 and R3 are trifluoromethyl.
-
25. The process of claim 24 wherein R2 is H.
-
26. The process of claim 25 wherein each R5 is H.
-
27. The process of claim 26 herein R6 is a methyl group.
-
28. The process of claim 27 wherein R4 is H.
-
29. The process of claim 20 wherein the fluorinated β
- -ketone is 1,1,1,5,5,5-hexafluoro-2,4-pentanedione and L is trimethylvinyl silane.
-
30. The process of claim 22 wherein the monovalent copper β
- -diketone complex product has the structural formula
wherein R1 and R3 are each independently trifluoromethyl, R2 is H, R4 is H, and each R5 is independently H.
- -diketone complex product has the structural formula
-
15. In a process for the removal of β
- -diketone byproducts from a reaction mixture containing a monovalent copper β
-diketone complex product prepared by reacting a reactive copper compound with an H form or K form fluorinated β
-diketone and, optionally, a stabilizing organic ligand contaminated with unreacted H form or K form of a fluorinated β
-diketone and a divalent copper β
-diketone complex byproduct, the improvement for removing the unreacted H form or K form of the fluorinated β
-diketone and the divalent copper β
-diketone complex byproduct from the reaction mixture which comprises;contacting the reaction mixture with an effective amount of a solution of acid and double deionized water for solubilizing the H form or K form fluorinated β
-diketonate and divalent copper β
-diketone complex byproduct;
forming an aqueous phase containing the H form or K form fluorinated β
-diketone and divalent copper β
-diketone complex byproduct and an organic phase containing the monovalent copper β
-diketone complex product;
separating the aqueous phase from the organic phase; and
,recovering the monovalent copper β
-diketone complex product.
- -diketone byproducts from a reaction mixture containing a monovalent copper β
Specification
-
- Resources
Litigation Campaign Assessment
Thank you for your request. You will receive a custom alert email when the Litigation Campaign Assessment is available.
×
-
Current AssigneeVersum Materials US, LLC (Merck & Co., Inc.)
-
Original AssigneeAir Products and Chemicals Incorporated (Linde Plc)
-
InventorsZorich, Robert Sam, Thurmond, James Richard, Roberts, David Allen
-
Primary Examiner(s)NAZARIO GONZALEZ, PORFIRIO
-
Application NumberUS10/037,739Time in Patent Office446 DaysField of Search556/12, 556/40, 556/41, 556/112, 556/117, 427/587US Class Current556/41CPC Class CodesC07F 7/0803 Compounds with Si-C or Si-S...
