PRODUCTION OF ANHYDROUS QUATERNARY AMMONIUM HYDROXIDES
A method for the synthesis of anhydrous quaternary ammonium hydroxides having the formula (NR 1 R 2 R 3 R 4 ) OH, wherein R 1 , R 2 , R 3 and R 4 are the same as or different from one another and are each individually selected from H, C 1 -C 10 alkyls including linear or cyclo alkyls, and C 6 -C 12 aryls by reacting an alkylene oxide with a tertiary amine having the formula R 1 R 2 R 3 N wherein R 1 , R 2 , and R 3 are the same or different and are each individually selected from C 1 -C 10 alkyls including linear and cyclo alkyls, C 1 -C 10 hydroxyalkyls, C 6 -C 12 aryls, and formulations having anhydrous quaternary ammonium hydroxides.
1 . A method for the synthesis of an anhydrous quaternary ammonium hydroxide comprising:
reacting an alkylene oxide with a tertiary amine having the formula R1R2R3N wherein R1, R2, and R3 are the same or different and are each individually selected from C 1 -C 10 alkyls, C 1 -C 10 hydroxyalkyls and C 6 -C 12 aryls, to produce an anhydrous quaternary ammonium hydroxide having the formula (NR 1 R 2 R 3 R 4 ) OH, wherein R 1 , R 2 , R 3 , and R 4 are the same as or different from one another and are each individually selected from H, C 1 -C 10 alkyls, C 1 -C 10 hydroxyalkyls and C 6 -C 12 aryls.
2 . The method of claim 1 , wherein the alkylene oxide is selected from ethylene oxide, propylene oxide, butylene oxide, allyl glycidyl ether, hexene oxide, styrene oxide, epichlorohydrin, cyclohexene oxide and spiro-epoxy oxindole.
3 . The method of claim 1 , wherein the tertiary amine is selected from trimethylamine, triethylamine, tripropylamine, dimethylethylamine, diethylmethylamine, dimethylethanolamine, methyldiethanolamine, triethanolamine, dimethylpropanolamine, diethylethanolamine and methylethylpropanolamine.
4 . The method of claim 1 , wherein the reaction is performed in an aqueous environment.
5 . The method of claim 1 , wherein the reaction produces byproducts including water and unreacted amine.
6 . The method of claim 5 , wherein the reaction produces less than about 5% by weight water as byproduct.
7 . An electronic application formulation comprising an anhydrous quaternary ammonium hydroxide as claimed in claim 1 .
8 . The electronic application formulation of claim 7 , further comprising a solvent including isopropyl alcohol or an ethylene oxide reactive solvent.
9 . The electronic application formulation of claim 7 , further comprising water.
10 . An anhydrous quaternary ammonium hydroxide composition obtained by reacting an alkylene oxide with a tertiary amine having the formula R1R2R3N wherein R1, R2, and R3 are the same or different and are each individually selected from C 1 -C 10 alkyls, C 1 -C 10 hydroxyalkyls and C 6 -C 12 aryls.
11 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein the alkylene oxide is selected from ethylene oxide, propylene oxide, butylene oxide, allyl glycidyl ether, hexene oxide, styrene oxide, epichlorohydrin, cyclohexene oxide, and spiro-epoxy oxindole.
12 . The anhydrous quaternary ammonium hydroxide composition of claim 11 , wherein the alkylene oxide is ethylene oxide.
13 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein R1, R2 and R3 are individually selected from C 1 -C 10 alkyls.
14 . The anhydrous quaternary ammonium hydroxide composition of claim 13 , wherein R1, R2 and R3 are individually selected from methyl and ethyl.
15 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein R1, R2 and R3 are individually selected from C 1 -C 10 hydroxyalkyls.
16 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein a molar ratio of alkylene oxide to tertiary amine present in the reaction ranges from about 6:1 to about 1:3.
17 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein the reaction is performed in the presence of a solvent including N-methyl-2-pyrrolidone, dimethyl sulfoxide, dimethylacetamide, t-butyl alcohol, ethylene glycol, or propylene glycol.
18 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein the reaction is conducted at a temperature in the range from about 30° C. to about 60° C.
19 . The anhydrous quaternary ammonium hydroxide composition of claim 18 , wherein the reaction is conducted at a pressure less than about 60 psi.
20 . A method for etching, stripping or cleaning a surface of a semiconductor device including contacting the surface with the electronic application formulation of claim 7 .