Process stability of NBDE using substituted phenol stabilizers

• US 8,173,213 B2
• Filed: 05/21/2009
• Issued: 05/08/2012
• Est. Priority Date: 05/28/2008
• Status: Active Grant

• Current Assignee: Versum Materials US, LLC (Merck & Co., Inc.)
• Original Assignee: Air Products and Chemicals Incorporated (Linde Plc)
• Inventors: Mayorga, Steven Gerard, Haas, Mary Kathryn, O'Neill, Mark Leonard, Sinatore, Dino
• Primary Examiner(s): Daniels, Matthew
• Assistant Examiner(s): CORDRAY, DENNIS R
• Application Number:
  US12/470,002
• Publication Number:
  US 20090297711A1
• Time in Patent Office: 1,083 Days
• Field of Search: 427/250, 427/255.18, 427/255.19, 427/255.23, 427/255.29, 427/255.31, 427/255.37, 427/255.4, 427/255.28, 585/6, 252/182.29, 252/404, 438/758, 438/778
• US Class Current: 427/255.37
• 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 15/00 Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
• 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 stabilizer compound having the Formula (I),
R¹,R²,R³,R⁴,R⁵(C₆)OH  Formula (I)

• • wherein R′ 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 stabilizer compound is present in an amount greater than 200 ppm up to 20,000 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 method of forming a layer of carbon-doped silicon oxide on a substrate, the method comprising the steps of:

providing a cyclic alkene composition in a first container, wherein the cyclic alkene is at least one compound selected from the group consisting of;

dipentene, phellandrene, dicyclopentadiene, alpha-terpinene, gamma-terpinene, limonene, alphapinene, 3-carene, terpinolene, norbornene, norbomadiene, 5-vinyl-2-norbornene, and 5-ethylidene-2-norbornene, a silicon containing compound in a second container, a film deposition tool, a film deposition chamber within said film deposition tool, and a stream of carrier gas to sweep said cyclic alkene composition and said silicon containing compound through a connection into the film deposition chamber, wherein said substrate is disposed within said film deposition chamber of said film deposition tool;

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

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

transporting said vapors of said cyclic alkene composition and said silicon containing compound into said film deposition chamber via the carrier gas stream; and

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

a stabilizer compound selected form the group consisting of;

phenol, 4-methylphenol, 3-methylphenol, 2-methylphenol, 4-ethylphenol, 4-propylphenol, 4-iso-propylphenol, 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, 2,4-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol (BHT), 1,3-dihydroxybenzene, hydroquinone, 2-(benzyloxy)phenol, 3,4,5-trimethoxyphenol, 3-ethoxy-4-methylphenol, 4-benzyloxyphenol, 4-benzy1-2,6-di-tert-butylphenol, 2-(2-butenyl)phenol, 4-propoxyphenol, 4-butoxyphenol, 2-(4-methylbenzyl)phenol, 2,4,6-tris-benzyloxyphenol, 2,4-dicyclohexy1-5-methylphenol, 6-tert-butyl-1,2-dihydroxybenzene and mixtures thereof,

wherein the stabilizer composition is present in a concentration of from 500 ppm up to 10,000 ppm, and wherein said stabilizer compound has a boiling point lower than 265°

C.

2. The method of claim 1, wherein said stabilizer compound is 4-methoxyphenol.

3. The method of claim 1 wherein the stabilizer is present in the range of from 1000 to 5000 ppm.

4. The method of claim 1 wherein the stabilizer is present in the range of from 3000 to 5000 ppm.