US20230339986A1 - Stable alkenyl or alkynyl-containing organosilicon precursor compositions - Google Patents
Stable alkenyl or alkynyl-containing organosilicon precursor compositions Download PDFInfo
- Publication number
- US20230339986A1 US20230339986A1 US18/333,759 US202318333759A US2023339986A1 US 20230339986 A1 US20230339986 A1 US 20230339986A1 US 202318333759 A US202318333759 A US 202318333759A US 2023339986 A1 US2023339986 A1 US 2023339986A1
- Authority
- US
- United States
- Prior art keywords
- container
- alkynyl
- alkenyl
- tert
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000000304 alkynyl group Chemical group 0.000 title claims abstract description 50
- 125000003342 alkenyl group Chemical group 0.000 title claims abstract description 47
- 239000002243 precursor Substances 0.000 title abstract description 36
- 239000000203 mixture Substances 0.000 title abstract description 22
- 230000005540 biological transmission Effects 0.000 claims abstract description 22
- 150000003961 organosilicon compounds Chemical class 0.000 claims abstract description 21
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 claims description 38
- 239000012535 impurity Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000005227 gel permeation chromatography Methods 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 5
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- WCBPJVKVIMMEQC-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine Chemical group [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 WCBPJVKVIMMEQC-UHFFFAOYSA-N 0.000 claims description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims description 2
- ROHFBIREHKPELA-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enoic acid;methane Chemical compound C.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O ROHFBIREHKPELA-UHFFFAOYSA-N 0.000 claims description 2
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 claims description 2
- IMOYOUMVYICGCA-UHFFFAOYSA-N 2-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C=C1C(C)(C)C IMOYOUMVYICGCA-UHFFFAOYSA-N 0.000 claims description 2
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 claims description 2
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 claims description 2
- UDBVWWVWSXSLAX-UHFFFAOYSA-N 4-[2,3-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)C(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)CC1=CC(C(C)(C)C)=C(O)C=C1C UDBVWWVWSXSLAX-UHFFFAOYSA-N 0.000 claims description 2
- JTTMYKSFKOOQLP-UHFFFAOYSA-N 4-hydroxydiphenylamine Chemical compound C1=CC(O)=CC=C1NC1=CC=CC=C1 JTTMYKSFKOOQLP-UHFFFAOYSA-N 0.000 claims description 2
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 claims description 2
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N gallic acid propyl ester Natural products CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 2
- GTIBACHAUHDNPH-WHYMJUELSA-N n,n'-bis[(z)-benzylideneamino]oxamide Chemical compound C=1C=CC=CC=1\C=N/NC(=O)C(=O)N\N=C/C1=CC=CC=C1 GTIBACHAUHDNPH-WHYMJUELSA-N 0.000 claims description 2
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002990 phenothiazines Chemical class 0.000 claims description 2
- 235000019281 tert-butylhydroquinone Nutrition 0.000 claims description 2
- 239000011732 tocopherol Substances 0.000 claims description 2
- 229930003799 tocopherol Natural products 0.000 claims description 2
- 235000019149 tocopherols Nutrition 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 claims description 2
- 239000010497 wheat germ oil Substances 0.000 claims description 2
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 23
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000004806 packaging method and process Methods 0.000 abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 20
- 239000007788 liquid Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 15
- 229910001220 stainless steel Inorganic materials 0.000 description 12
- 239000010935 stainless steel Substances 0.000 description 12
- 230000032683 aging Effects 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 238000005229 chemical vapour deposition Methods 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000000151 deposition Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- -1 for example Chemical class 0.000 description 5
- 238000004255 ion exchange chromatography Methods 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000001307 helium Substances 0.000 description 4
- 229910052734 helium Inorganic materials 0.000 description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 238000000231 atomic layer deposition Methods 0.000 description 3
- 238000005137 deposition process Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000004224 UV/Vis absorption spectrophotometry Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- NNKJLYMBVRDUEI-UHFFFAOYSA-N chloro-tris(ethenyl)silane Chemical compound C=C[Si](Cl)(C=C)C=C NNKJLYMBVRDUEI-UHFFFAOYSA-N 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical group [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/20—Purification, separation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D25/00—Details of other kinds or types of rigid or semi-rigid containers
- B65D25/14—Linings or internal coatings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D65/00—Wrappers or flexible covers; Packaging materials of special type or form
- B65D65/02—Wrappers or flexible covers
- B65D65/16—Wrappers or flexible covers with provision for excluding or admitting light
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
- C07F7/0807—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0896—Compounds with a Si-H linkage
Definitions
- the present disclosure is related to the field of low dielectric constant materials prepared by chemical vapor deposition (CVD) methods which serve as insulating layers in electronic devices.
- the present disclosure is directed to an alkenyl or alkynyl-containing organosilicon precursor compositions for use as precursors to dielectric materials that eliminate process problems related to precipitation of impurities caused by self-polymerization in the liquid state.
- Alkenyl or alkynyl-containing organosilicon precursor compounds such as, for example, tetravinylsilane (TVS) have been identified as leading candidates for the deposition of silicon carbide (SiC), silicon oxycarbide (SiOC), and silicon carbonitirde (SiCN) films.
- a direct liquid injection (DLI) technique is employed to repeatedly deliver precisely controlled quantities of precursor compounds to the process tool deposition chamber.
- the deposition process can include chemical vapor deposition (CVD), atomic layer deposition (ALD), plasma enhanced chemical vapor deposition (PECVD), flowable chemical vapor deposition (FCVD), plasma enhanced atomic layer deposition (PEALD) or other methods to deposit these films.
- CVD chemical vapor deposition
- ALD atomic layer deposition
- PECVD plasma enhanced chemical vapor deposition
- FCVD flowable chemical vapor deposition
- PEALD plasma enhanced atomic layer deposition
- the unsaturated moiety of the organosilicon precursor compound is prone to polymerization and the organosilicon precursor compound will gradually degrade or polymerize and precipitate out at ambient temperature or at moderate temperatures that are often encountered during normal processing, purification or application of the particular chemical.
- Such build-up of residues/precipitate leads to a disruption in flow of vapor into the process chamber, which would severely impact the repeatability of film growth making the process unworthy of high volume manufacturing (HVM).
- HVM high volume manufacturing
- residues could include the residue left behind in the injector as a result of impurities in the alkenyl or alkynyl-containing organosilicon precursor compound, like chlorine-containing impurities that have less volatility relative to the alkenyl or alkynyl-containing organosilicon precursor compound, and higher molecular weight impurities resulting from self-initiated polymerization of the alkenyl or alkynyl-containing organosilicon precursor compound due to light absorption or the presence of other free radical generating impurities.
- impurities in the alkenyl or alkynyl-containing organosilicon precursor compound like chlorine-containing impurities that have less volatility relative to the alkenyl or alkynyl-containing organosilicon precursor compound, and higher molecular weight impurities resulting from self-initiated polymerization of the alkenyl or alkynyl-containing organosilicon precursor compound due to light absorption or the presence of other free radical generating impurities.
- the alkenyl or alkynyl-containing organosilicon precursor compound which includes a concentration of impurities that falls within a given range for both low and higher molecular weight impurities. Accordingly, there is a need for an alkenyl or alkynyl-containing organosilicon precursor compound that is produced as pure as possible and which remains pure over time, once it is packaged.
- the present disclosure provides a method for producing an alkenyl or alkynyl-containing organosilicon precursor composition, the method comprising the steps of: distilling at least once a composition comprising an alkenyl or alkynyl-containing organosilicon compound having the formula R n SiR 1 4-n wherein R is selected from a linear or branched C 2 to C 6 alkenyl group, a linear or branched C 2 to C 6 alkynyl group; R 1 is selected from hydrogen, a linear or branched C 1 to C 10 alkyl group, a C 3 to C 10 cyclic alkyl group, and a C 3 to C 10 aryl group; and n is a number selected from 1 to 4, and wherein a distilled alkenyl or alkynyl-containing organosilicon precursor composition is produced after distilling; and packaging the distilled alkenyl or alkynyl-containing organosilicon precursor composition in a container, wherein the container permits transmission into the container of no more
- the present disclosure provides a system for storing an alkenyl or alkynyl-containing organosilicon compound, the system comprising: a container, wherein the container permits transmission into the container of no more than 10% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm; and contained within the container, a distilled alkenyl or alkynyl-containing organosilicon compound having the formula R n SiR 1 4-n wherein R is selected a linear or branched C 2 to C 6 alkenyl group, a linear or branched C 2 to C 6 alkynyl group; R 1 is selected from hydrogen, a linear or branched C 1 to C 10 alkyl group, a C 3 to C 10 cyclic alkyl group, and a C 3 to C 10 aryl group and; and n is a number selected from 1 to 4.
- Described is a method for producing an alkenyl or alkynyl-containing organosilicon precursor composition comprising the steps of: distilling at least once a composition comprising an alkenyl or alkynyl-containing organosilicon compound having the formula R n SiR 1 4-n wherein R is selected a linear or branched C 2 to C 6 alkenyl group, a linear or branched C 2 to C 6 alkynyl group; R 1 is selected from hydrogen, a linear or branched C 1 to C 10 alkyl group, a C 3 to C 10 cyclic alkyl group, and a C 3 to C 10 aryl group; and n is a number selected from 1 to 4, wherein a distilled alkenyl or alkynyl-containing organosilicon precursor composition is produced after distilling; and packaging the distilled alkenyl or alkynyl-containing organosilicon precursor composition in a container, wherein the container permits transmission into the container of no more than 10% of
- the precursors of various embodiments include alkenyl (vinyl) and/or alkynyl groups.
- the precursors in their intended use, are exposed to reactive radicals to initiate a radical induced polymerization in the deposition chamber.
- the method of the present disclosure further comprises adding a stabilizer compound to the distilled alkenyl or alkynyl-containing organosilicon precursor composition prior to said packing step.
- composition comprising a crude (i.e., prior to purification by distillation according to the present disclosure) alkenyl or alkynyl-containing organosilicon compound such as, for example, one having a residual chloride or other halide impurity
- the majority of the chloride-containing components can be removed from the crude alkenyl or alkynyl-containing organosilicon compound through distillation.
- Exemplary compounds for the alkenyl or alkynyl-containing organosilicon compound having the formula R n SiR 1 4-n include, but are not limited to, the following:
- the alkenyl or alkynyl-containing organosilicon compound comprises tetravinylsilane (TVS).
- linear or branched alkyl denotes a linear functional group having from 1 to 10, 3 to 10, or 1 to 6 carbon atoms.
- branched alkyl denotes a branched functional group having from 3 to 10, or 3 to 6 carbon atoms.
- Exemplary linear or branched alkyl groups include, but are not limited to, methyl (Me), ethyl (Et), isopropyl (Pr i ), isobutyl (Bu i ), sec-butyl (Bu s ), tert-butyl (Bu t ), iso-pentyl, tert-pentyl (am), isohexyl, and neohexyl.
- the alkyl group may have one or more functional groups such as, but not limited to, an alkoxy group, a dialkylamino group or combinations thereof, attached thereto. In other embodiments, the alkyl group does not have one or more functional groups attached thereto.
- the alkyl group may be saturated or, alternatively, unsaturated.
- cyclic alkyl denotes a cyclic group having from 3 to 10 or 5 to 10 atoms.
- exemplary cyclic alkyl groups include, but are not limited to, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl groups.
- the cyclic alkyl group may have one or more C 1 to C 10 linear, branched substituents, or substituents containing oxygen or nitrogen atoms.
- the cyclic alkyl group may have one or more linear or branched alkyls or alkoxy groups as substituents, such as, for example, a methylcyclohexyl group or a methoxycyclohexyl group.
- aryl denotes an aromatic cyclic functional group having from 3 to 10 carbon atoms, from 5 to 10 carbon atoms, or from 6 to 10 carbon atoms.
- exemplary aryl groups include, but are not limited to, phenyl, benzyl, chlorobenzyl, tolyl, and o-xylyl.
- alkenyl group denotes a group which has one or more carbon-carbon double bonds and has from 2 to 12, from 2 to 10, or from 2 to 6 carbon atoms.
- alkenyl groups include, but are not limited to, vinyl or allyl groups.
- alkynyl group denotes a group which has one or more carbon-carbon triple bonds and has from 2 to 12 or from 2 to 6 carbon atoms.
- the term “unsaturated” as used herein means that the functional group, substituent, ring or bridge has one or more carbon double or triple bonds.
- An example of an unsaturated ring can be, without limitation, an aromatic ring such as a phenyl ring.
- the term “saturated” means that the functional group, substituent, ring or bridge does not have one or more double or triple bonds.
- one or more of the alkyl group, alkenyl group, alkynyl group, aryl group, and/or cyclic alkyl group in the formulae may be “substituted” or have one or more atoms or group of atoms substituted in place of, for example, a hydrogen atom.
- substituents include, but are not limited to, oxygen, sulfur, halogen atoms (e.g., F, Cl, I, or Br), nitrogen, alkyl groups, and phosphorous.
- one or more of the alkyl group, alkenyl group, alkynyl group, aromatic and/or aryl group in the formulae may be unsubstituted.
- the organosilicon compounds according to the present disclosure are preferably substantially free of halide.
- halide ions such as, for example, chlorides (i.e. chloride-containing species such as HCl or organosilicon compounds having at least one Si—Cl bond) and fluorides, bromides, and iodides, means less than 100 ppm (by weight) measured by ion chromatography (IC), preferably less than 50 ppm measured by IC and more preferably less than 10 ppm measured by IC and most preferably 0 ppm measured by IC.
- IC ion chromatography
- the organosilicon compounds are preferably substantially free of metal ions such as Li + , Na + , K + , Mg 2+ , Ca 2+ , Al 3+ , Fe 2+ , Fe 3+ , Ni 2+ , Cr 3+ .
- metal ions such as Li + , Na + , K + , Mg 2+ , Ca 2+ , Al 3+ , Fe 2+ , Fe 3+ , Ni 2+ , Cr 3+ .
- the term “substantially free” as it relates to Li, Na, K, Mg, Ca, Al, Fe, Ni, Cr means less than 5 ppm (by weight), preferably less than 3 ppm, and more preferably less than 1 ppm, and most preferably 0.1 ppm as measured by ICP-MS.
- the organosilicon compounds are preferably also substantially free of water or organosilane impurities such as other alkenyl or alkynyl-containing organosilicon compounds either from starting materials or by-products from the synthesis, as used herein, the term “substantially free” as it relates to water is less than 100 ppm (by weight) as analyzed by Karl Fisher, preferably less than 50 ppm, and more preferably less than 10 ppm; the sum of all organosilane impurities such as trivinylchlorosilane as analyzed by gas chromatography (GC) is less than 1.0 wt. %, preferably less than 0.5 wt. %, and preferably less than 0.1 wt. %.
- GC gas chromatography
- a stabilizer compound added to the distilled alkenyl or alkynyl-containing organosilicon precursor composition is a stabilizer compound.
- exemplary stabilizer compounds include 2,6-di-tert-butyl-4-methyl phenol (or BHT for butylhydroxytoluene), 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, propyl ester 3,4,5-trihydroxy-benzoic acid, 2-(1,1-dimethylethyl)-1,4-benzenediol, diphenylpicrylhydrazyl, 4-tert-butylcatechol, N-methylaniline, p-methoxydiphenylamine, diphenylamine, N,N′-diphenyl-p-phenylenediamine, p-hydroxydiphenylamine, phenol, octadecyl-3-(3,5-d
- the method of the present development comprises the step of packaging the distilled alkenyl or alkynyl-containing organosilicon precursor composition in a container, wherein the container permits transmission into the container of no more than 10% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
- the packaged distilled alkenyl or alkynyl-containing organosilicon precursor composition in the container as described herein is referred to as a “system.”
- the container permits transmission of no more than 7% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. In other embodiments, the container permits transmission of no more than 5% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. In other embodiments, the container permits transmission of no more than 3% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. In other embodiments, the container permits transmission of no more than 2% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. In yet another embodiments, the container permits transmission of no more than 1% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. In still other embodiments, the container permits 0% transmission into the container of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
- the percent of UV and visible light transmission through a solid medium can be measured by any method known to those skilled in the art such as, for example, UV-VIS absorption spectroscopy, where a sample is illuminated from one side, and the intensity of the light that exits from the sample in every direction is measured.
- Any UV-VIS absorption instrument commercially available may be employed to measure transmission of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm according to the present disclosure.
- the container is made of stainless steel. If a glass or quartz container is employed, then either the container has walls thick enough to prevent the transmission of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm or the walls of such container are covered with a layer of material to prevent the transmission of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. Examples of such materials include metal foils and synthetic resin coatings.
- the container once filled with the distilled alkenyl or alkynyl-containing organosilicon precursor composition of the present disclosure is stored at a temperature of from 15° C. to 30° C., and more preferably at room temperature.
- Example 1 Samples from two different sources of tetravinylsilanes (TVS) were analyzed by Gel Permeation Chromatography (GPC) to determine the concentration of higher molecular weight (HMW) species present in the liquid.
- Table 1 shows the comparative samples showing TVS containing >1 wt. % of HMW species (>1000 atomic mass unit (amu), for example species or oligomers having molecular weight ranging from 1000 to 20000 amu) and TVS containing 0.1 wt. % (1000 ppm) higher molecular weight species (>1000 amu).
- the two sources of TVS would have significantly differing impacts on the continuous delivery of TVS through the DLI system and into the CVD process chamber.
- Example 2 The impact of TVS with higher concentration of impurities having amu of 1000 or higher
- a flow test was done on Versum Materials DLI (direct liquid injection) test system with Horiba STEC LF-410A liquid flow meter and MV1000 vapor injector.
- 840 g of Tetravinylsilane (TVS) chemical was transferred under inert atmosphere to a Versum materials ChemguardTM liquid containment system.
- the TVS chemical assay was 96 wt. %
- HMW impurity was 1.8 wt. %
- chloride content was 97 ppm
- H 2 O content was 1076 ppm.
- the injector temperature was set to 100° C.
- the injector downstream line was heated to 110° C.
- Helium gas set at a pressure of 30 pisg was used to push the liquid to the vapor injector.
- the liquid flow was set at 0.3 g/min.
- the liquid flow was periodically turned ON for 8 minutes and turned OFF for 2 mins controlled by PLC.
- the liquid flow rate and line pressure and injector control voltage were stable throughout the test until the chemical supply ran out after 27 hours of flow test.
- the TVS container was unloaded from the ChemguardTM tool and a container with hexane was installed into the ChemguardTM.
- a hexane flush was performed with the same tool set up. The hexane flow was stable, indicating that no oligomers/polymers were impeding the delivery of chemical through the DLI and to the tool.
- Example 4 The stability or shelf life of TVS is impacted by the initial concentration of higher molecular weight impurities.
- Example 5 The Effect of the Water and Chloride Levels of TVS on the Corrosion of Stainless Steel.
- Test Sample #1 had low chloride and low water; Sample #2 had low chloride and high water; Sample #3 had high chloride and low water; and Sample #4 had high chloride and high water.
- These 4 samples of TVS were analyzed for their stainless steel metals content (Fe, Cr, Ni, Mn and Mo) by ICP-MS (inductively coupled plasma-mass spectrometry) before and after heat treatment. These were also analyzed by GC (gas chromatography) before and after heating to assess the impact of ageing on the TVS purity. A summary of these four samples and the analytical results are in Table 3 below.
Abstract
A method for producing an alkenyl or alkynyl-containing organosilicon precursor composition, the method comprising the steps of distilling at least once a composition comprising an alkenyl or alkynyl-containing organosilicon compound having the formula RnSiR14-n wherein R is selected a linear or branched C2 to C6 alkenyl group, a linear or branched C2 to C6 alkynyl group; R1 is selected from hydrogen, a linear or branched C1 to C10 alkyl group, and a C3 to C10 cyclic alkyl group; and n is a number selected from 1 to 4, wherein a distilled alkenyl or alkynyl-containing organosilicon precursor composition is produced after distilling; and packaging the distilled alkenyl or alkynyl-containing organosilicon precursor composition in a container, wherein the container permits transmission into the container of no more than 10% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
Description
- This application is a divisional of U.S. application Ser. No. 16/547,468, filed on Aug. 21, 2019, which claims the benefit of U.S. Provisional Application No. 62/722,090, filed on Aug. 23, 2018, and the entire contents of both applications are incorporated herein by reference thereto for all allowable purposes.
- The present disclosure is related to the field of low dielectric constant materials prepared by chemical vapor deposition (CVD) methods which serve as insulating layers in electronic devices. In particular, the present disclosure is directed to an alkenyl or alkynyl-containing organosilicon precursor compositions for use as precursors to dielectric materials that eliminate process problems related to precipitation of impurities caused by self-polymerization in the liquid state.
- Alkenyl or alkynyl-containing organosilicon precursor compounds such as, for example, tetravinylsilane (TVS) have been identified as leading candidates for the deposition of silicon carbide (SiC), silicon oxycarbide (SiOC), and silicon carbonitirde (SiCN) films. During a conventional deposition process, a direct liquid injection (DLI) technique is employed to repeatedly deliver precisely controlled quantities of precursor compounds to the process tool deposition chamber. The deposition process can include chemical vapor deposition (CVD), atomic layer deposition (ALD), plasma enhanced chemical vapor deposition (PECVD), flowable chemical vapor deposition (FCVD), plasma enhanced atomic layer deposition (PEALD) or other methods to deposit these films.
- During deposition it is necessary to deliver a constant flow of alkenyl or alkynyl-containing organosilicon precursor compound and alkenyl or alkynyl-containing organosilicon precursor compound-like precursors to the process tool using the combination of a liquid mass flow controller (LMFC) and a heated vaporizing injector system that will volatize the precursor, which will be swept away from the injector through a heated delivery line to the process chamber. During this process it is critical that non-volatile residues or components do not accumulate in the LMFC, injector, or chemical delivery line. The unsaturated moiety of the organosilicon precursor compound is prone to polymerization and the organosilicon precursor compound will gradually degrade or polymerize and precipitate out at ambient temperature or at moderate temperatures that are often encountered during normal processing, purification or application of the particular chemical. Such build-up of residues/precipitate leads to a disruption in flow of vapor into the process chamber, which would severely impact the repeatability of film growth making the process unworthy of high volume manufacturing (HVM).
- Such examples of residues could include the residue left behind in the injector as a result of impurities in the alkenyl or alkynyl-containing organosilicon precursor compound, like chlorine-containing impurities that have less volatility relative to the alkenyl or alkynyl-containing organosilicon precursor compound, and higher molecular weight impurities resulting from self-initiated polymerization of the alkenyl or alkynyl-containing organosilicon precursor compound due to light absorption or the presence of other free radical generating impurities. In such instances it is believed that the higher molecular weight impurities would remain soluble in the alkenyl or alkynyl-containing organosilicon precursor compound until they passed thru the injector and would then begin to either thicken or condense and fall out into the gas delivery line where they would accumulate, eventually obstructing the flow of gas into the process chamber.
- To prevent such disruptive phenomena from occurring it is necessary to have the proper composition of the alkenyl or alkynyl-containing organosilicon precursor compound, which includes a concentration of impurities that falls within a given range for both low and higher molecular weight impurities. Accordingly, there is a need for an alkenyl or alkynyl-containing organosilicon precursor compound that is produced as pure as possible and which remains pure over time, once it is packaged.
- The present disclosure provides a method for producing an alkenyl or alkynyl-containing organosilicon precursor composition, the method comprising the steps of: distilling at least once a composition comprising an alkenyl or alkynyl-containing organosilicon compound having the formula RnSiR1 4-n wherein R is selected from a linear or branched C2 to C6 alkenyl group, a linear or branched C2 to C6 alkynyl group; R1 is selected from hydrogen, a linear or branched C1 to C10 alkyl group, a C3 to C10 cyclic alkyl group, and a C3 to C10 aryl group; and n is a number selected from 1 to 4, and wherein a distilled alkenyl or alkynyl-containing organosilicon precursor composition is produced after distilling; and packaging the distilled alkenyl or alkynyl-containing organosilicon precursor composition in a container, wherein the container permits transmission into the container of no more than 10% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
- In another aspect, the present disclosure provides a system for storing an alkenyl or alkynyl-containing organosilicon compound, the system comprising: a container, wherein the container permits transmission into the container of no more than 10% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm; and contained within the container, a distilled alkenyl or alkynyl-containing organosilicon compound having the formula Rn SiR1 4-n wherein R is selected a linear or branched C2 to C6 alkenyl group, a linear or branched C2 to C6 alkynyl group; R1 is selected from hydrogen, a linear or branched C1 to C10 alkyl group, a C3 to C10 cyclic alkyl group, and a C3 to C10 aryl group and; and n is a number selected from 1 to 4.
- The various embodiments of the disclosure can be used alone or in combinations with each other.
- Described is a method for producing an alkenyl or alkynyl-containing organosilicon precursor composition, the method comprising the steps of: distilling at least once a composition comprising an alkenyl or alkynyl-containing organosilicon compound having the formula RnSiR1 4-n wherein R is selected a linear or branched C2 to C6 alkenyl group, a linear or branched C2 to C6 alkynyl group; R1 is selected from hydrogen, a linear or branched C1 to C10 alkyl group, a C3 to C10 cyclic alkyl group, and a C3 to C10 aryl group; and n is a number selected from 1 to 4, wherein a distilled alkenyl or alkynyl-containing organosilicon precursor composition is produced after distilling; and packaging the distilled alkenyl or alkynyl-containing organosilicon precursor composition in a container, wherein the container permits transmission into the container of no more than 10% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
- The precursors of various embodiments include alkenyl (vinyl) and/or alkynyl groups. In one or more embodiments, in their intended use, the precursors are exposed to reactive radicals to initiate a radical induced polymerization in the deposition chamber.
- In one embodiment, the method of the present disclosure further comprises adding a stabilizer compound to the distilled alkenyl or alkynyl-containing organosilicon precursor composition prior to said packing step.
- To the extent that a composition comprising a crude (i.e., prior to purification by distillation according to the present disclosure) alkenyl or alkynyl-containing organosilicon compound such as, for example, one having a residual chloride or other halide impurity, the majority of the chloride-containing components can be removed from the crude alkenyl or alkynyl-containing organosilicon compound through distillation.
- Exemplary compounds for the alkenyl or alkynyl-containing organosilicon compound having the formula RnSiR1 4-n include, but are not limited to, the following:
- In certain embodiments, the alkenyl or alkynyl-containing organosilicon compound comprises tetravinylsilane (TVS).
- In the formula above and throughout the description, the term “linear or branched alkyl” denotes a linear functional group having from 1 to 10, 3 to 10, or 1 to 6 carbon atoms. In the formulae above and throughout the description, the term “branched alkyl” denotes a branched functional group having from 3 to 10, or 3 to 6 carbon atoms. Exemplary linear or branched alkyl groups include, but are not limited to, methyl (Me), ethyl (Et), isopropyl (Pri), isobutyl (Bui), sec-butyl (Bus), tert-butyl (But), iso-pentyl, tert-pentyl (am), isohexyl, and neohexyl. In certain embodiments, the alkyl group may have one or more functional groups such as, but not limited to, an alkoxy group, a dialkylamino group or combinations thereof, attached thereto. In other embodiments, the alkyl group does not have one or more functional groups attached thereto. The alkyl group may be saturated or, alternatively, unsaturated.
- In the formulae above and throughout the description, the term “cyclic alkyl” denotes a cyclic group having from 3 to 10 or 5 to 10 atoms. Exemplary cyclic alkyl groups include, but are not limited to, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl groups. In certain embodiments, the cyclic alkyl group may have one or more C1 to C10 linear, branched substituents, or substituents containing oxygen or nitrogen atoms. In this or other embodiments, the cyclic alkyl group may have one or more linear or branched alkyls or alkoxy groups as substituents, such as, for example, a methylcyclohexyl group or a methoxycyclohexyl group.
- In the formulae above and throughout the description, the term “aryl” denotes an aromatic cyclic functional group having from 3 to 10 carbon atoms, from 5 to 10 carbon atoms, or from 6 to 10 carbon atoms. Exemplary aryl groups include, but are not limited to, phenyl, benzyl, chlorobenzyl, tolyl, and o-xylyl.
- In the formulae above and throughout the description, the term “alkenyl group” denotes a group which has one or more carbon-carbon double bonds and has from 2 to 12, from 2 to 10, or from 2 to 6 carbon atoms. Exemplary alkenyl groups include, but are not limited to, vinyl or allyl groups.
- The term “alkynyl group” denotes a group which has one or more carbon-carbon triple bonds and has from 2 to 12 or from 2 to 6 carbon atoms.
- In the formulae above and through the description, the term “unsaturated” as used herein means that the functional group, substituent, ring or bridge has one or more carbon double or triple bonds. An example of an unsaturated ring can be, without limitation, an aromatic ring such as a phenyl ring. The term “saturated” means that the functional group, substituent, ring or bridge does not have one or more double or triple bonds.
- In certain embodiments, one or more of the alkyl group, alkenyl group, alkynyl group, aryl group, and/or cyclic alkyl group in the formulae may be “substituted” or have one or more atoms or group of atoms substituted in place of, for example, a hydrogen atom. Exemplary substituents include, but are not limited to, oxygen, sulfur, halogen atoms (e.g., F, Cl, I, or Br), nitrogen, alkyl groups, and phosphorous. In other embodiments, one or more of the alkyl group, alkenyl group, alkynyl group, aromatic and/or aryl group in the formulae may be unsubstituted.
- The organosilicon compounds according to the present disclosure are preferably substantially free of halide. As used herein, the term “substantially free” as it relates to halide ions (or halides) such as, for example, chlorides (i.e. chloride-containing species such as HCl or organosilicon compounds having at least one Si—Cl bond) and fluorides, bromides, and iodides, means less than 100 ppm (by weight) measured by ion chromatography (IC), preferably less than 50 ppm measured by IC and more preferably less than 10 ppm measured by IC and most preferably 0 ppm measured by IC. Significant levels of chloride in the final product can cause leaching metals from the stainless steel container during storage or use into the organosilicon precursor in presence of moisture or water and the leached metal ions may catalyze polymerization of the organosilicon precursor to form high molecular weight impurities. The gradual degradation of the organosilicon compounds may directly impact the film deposition process making it difficult for the semiconductor manufacturer to meet film specifications. In addition, the shelf-life or stability is negatively impacted by the higher degradation rate of the organosilicon compounds, thereby making it difficult to guarantee a 1-2 year shelf-life. The organosilicon compounds are preferably substantially free of metal ions such as Li+, Na+, K+, Mg2+, Ca2+, Al3+, Fe2+, Fe3+, Ni2+, Cr3+. As used herein, the term “substantially free” as it relates to Li, Na, K, Mg, Ca, Al, Fe, Ni, Cr means less than 5 ppm (by weight), preferably less than 3 ppm, and more preferably less than 1 ppm, and most preferably 0.1 ppm as measured by ICP-MS. The organosilicon compounds are preferably also substantially free of water or organosilane impurities such as other alkenyl or alkynyl-containing organosilicon compounds either from starting materials or by-products from the synthesis, as used herein, the term “substantially free” as it relates to water is less than 100 ppm (by weight) as analyzed by Karl Fisher, preferably less than 50 ppm, and more preferably less than 10 ppm; the sum of all organosilane impurities such as trivinylchlorosilane as analyzed by gas chromatography (GC) is less than 1.0 wt. %, preferably less than 0.5 wt. %, and preferably less than 0.1 wt. %.
- In some embodiments, added to the distilled alkenyl or alkynyl-containing organosilicon precursor composition is a stabilizer compound. Exemplary stabilizer compounds include 2,6-di-tert-butyl-4-methyl phenol (or BHT for butylhydroxytoluene), 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, propyl ester 3,4,5-trihydroxy-benzoic acid, 2-(1,1-dimethylethyl)-1,4-benzenediol, diphenylpicrylhydrazyl, 4-tert-butylcatechol, N-methylaniline, p-methoxydiphenylamine, diphenylamine, N,N′-diphenyl-p-phenylenediamine, p-hydroxydiphenylamine, phenol, octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, tetrakis (methylene (3,5-di-tert-butyl)-4-hydroxy-hydrocinnamate) methane, phenothiazines, alkylamidonoisoureas, thiodiethylene bis (3,5,-di-tert-butyl-4-hydroxy-hydrocinnamate, 1,2,-bis (3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl) hydrazine, tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, cyclic neopentanetetrayl bis (octadecyl phosphite), 4,4′-thiobis (6-tert-butyl-m-cresol), 2,2′-methylenebis (6-tert-butyl-p-cresol), oxalyl bis (benzylidenehydrazide) and naturally occurring antioxidants such as raw seed oils, wheat germ oil, tocopherols and gums. The function of the stabilizer compound is to prevent self-polymerization or oligomerization of the alkenyl or alkynyl-containing organosilicon precursor.
- The method of the present development comprises the step of packaging the distilled alkenyl or alkynyl-containing organosilicon precursor composition in a container, wherein the container permits transmission into the container of no more than 10% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. As used herein, the packaged distilled alkenyl or alkynyl-containing organosilicon precursor composition in the container as described herein is referred to as a “system.”
- In some embodiments, the container permits transmission of no more than 7% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. In other embodiments, the container permits transmission of no more than 5% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. In other embodiments, the container permits transmission of no more than 3% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. In other embodiments, the container permits transmission of no more than 2% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. In yet another embodiments, the container permits transmission of no more than 1% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. In still other embodiments, the container permits 0% transmission into the container of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
- The percent of UV and visible light transmission through a solid medium can be measured by any method known to those skilled in the art such as, for example, UV-VIS absorption spectroscopy, where a sample is illuminated from one side, and the intensity of the light that exits from the sample in every direction is measured. Any UV-VIS absorption instrument commercially available may be employed to measure transmission of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm according to the present disclosure.
- The material from which the container is made and the thickness of the container's wall structure operably inhibits transmission of light through the container wall structure having a wavelength between about 290 nm to 450 nm. In some embodiments, the container is made of stainless steel. If a glass or quartz container is employed, then either the container has walls thick enough to prevent the transmission of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm or the walls of such container are covered with a layer of material to prevent the transmission of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm. Examples of such materials include metal foils and synthetic resin coatings.
- An example of a container that can be employed in the present disclosure is the high-purity chemical container disclosed in U.S. Pat. No. 7,124,913 to Air Products and Chemicals, Inc. (Allentown, PA), and incorporated herein by reference.
- Preferably, the container once filled with the distilled alkenyl or alkynyl-containing organosilicon precursor composition of the present disclosure is stored at a temperature of from 15° C. to 30° C., and more preferably at room temperature.
- The following working examples show the importance of obtaining alkenyl and alkynal blends with low levels of impurities such as higher molecular weight species, moistures and halogens such as chloride
- Example 1: Samples from two different sources of tetravinylsilanes (TVS) were analyzed by Gel Permeation Chromatography (GPC) to determine the concentration of higher molecular weight (HMW) species present in the liquid. Table 1 below shows the comparative samples showing TVS containing >1 wt. % of HMW species (>1000 atomic mass unit (amu), for example species or oligomers having molecular weight ranging from 1000 to 20000 amu) and TVS containing 0.1 wt. % (1000 ppm) higher molecular weight species (>1000 amu). The two sources of TVS would have significantly differing impacts on the continuous delivery of TVS through the DLI system and into the CVD process chamber.
-
TABLE 1 Sample wt. % species~150 amu wt. % species > 1000 amu 1 98.4 1.6 2 99.9 0.1 - Example 2: The impact of TVS with higher concentration of impurities having amu of 1000 or higher
- A flow test was done on Versum Materials DLI (direct liquid injection) test system with Horiba STEC LF-410A liquid flow meter and MV1000 vapor injector. 840 g of Tetravinylsilane (TVS) chemical was transferred under inert atmosphere to a Versum materials Chemguard™ liquid containment system. The TVS chemical assay was 96 wt. %, HMW impurity was 1.8 wt. %, chloride content was 97 ppm and H2O content was 1076 ppm. The injector temperature was set to 100° C. The injector downstream line was heated to 110° C. Helium gas set at a pressure of 30 pisg was used to push the liquid to the vapor injector. An additional 100 sccm of helium was used as an inert carrier gas across the injector interface. The liquid flow was set at 0.3 g/min. The liquid flow was periodically turned ON for 8 minutes and turned OFF for 2 mins controlled by PLC. The liquid flow and pressure in the line initially were very stable. After 11 hours of chemical flow cycling, the liquid flow rate and line pressure started to fluctuate, indicating a disruption in stable flow of chemical to the process chamber. After the test, the TVS container was unloaded from the Chemguard™ tool and a container with 1 kg of hexane was installed onto Chemguard™. A hexane solvent flush was performed with the same tool set up. The hexane flow was not stable, confirming the injector was partially clogged. After the flow test was complete, the injector and tubing located post injector was inspected for residue. Some amount of brownish polymer material was found in the injector and tubing post injector. The hexane flush results also indicated that the oligomers/polymers formed from TVS with a high HMW impurity level could not be solubilized using hexane. Not to be bound by theory, these results suggest that the oligomers/polymers are accumulated in a region of the DLI system where the solvent has been vaporized and thus not capable of solvating the oligomers, causing unstable flow of chemical into the process chamber.
- Comparative Example 3: High purity TVS flow test.
- For comparison, a flow test was done on Versum Materials DLI (direct liquid injection) test system with Horiba STEC LF-410A liquid flow meter and MV1000 vapor injector with distilled high purity TVS chemical. 860 g of distilled TVS chemical was transferred under inert atmosphere to a Versum materials Chemguard™ liquid containment system. The TVS chemical assay was 99.5%, chloride content was 0.2 ppm and H2O content was 35 ppm. The injector temperature was set to 100° C. The injector downstream line was heated to 110° C. Helium gas at a pressure of 30 pisg was used to push the liquid to the vapor injector. An additional 100 sccm of helium was used as an inert carrier gas across the injector interface. The liquid flow was set at 0.3 g/min. The liquid flow was periodically turned ON for 8 minutes and turned OFF for 2 mins controlled by PLC. The liquid flow rate and line pressure and injector control voltage were stable throughout the test until the chemical supply ran out after 27 hours of flow test. After the test, the TVS container was unloaded from the Chemguard™ tool and a container with hexane was installed into the Chemguard™. A hexane flush was performed with the same tool set up. The hexane flow was stable, indicating that no oligomers/polymers were impeding the delivery of chemical through the DLI and to the tool.
- Example 4: The stability or shelf life of TVS is impacted by the initial concentration of higher molecular weight impurities.
- An accelerated aging test was performed by heating TVS samples at 125° C. to determine how impurity concentration can increase over time. Observed in Table 2 was an increase in higher molecular weight (HMW) impurities (>1000 amu such as) determined by GPC after heating of the samples and exposure for 1-3 days. Without intending to be bound by a particular theory, it is believed that this increase is observed resulting from self-polymerization of the TVS. The consequences of this polymerization would be the observed reduction of chemical flow into the deposition chamber as discussed above. Oligomers or high molecular weight impurities was determined by GPC. Results indicate that lower initial HMW impurity concentrations will result in more gradual increases over the lifetime of material, which should greatly reduce the risk of chemical delivery interruptions.
-
TABLE 2 High Molecular Weight Impurity Conc Sample Aging Condition (wt. %) (>1000 amu) 1 Unheated (control) 0.10 Heated 1 day 125° C. 0.19 Heated 2 days 125° C. 0.35 Heated 3 days 125° C. 0.67 2 Unheated (control) 0.29 Heated 1 day 125° C. 0.37 Heated 2 days 125° C. 0.70 Heated 3 days 125° C. 0.96 - Example 5: The Effect of the Water and Chloride Levels of TVS on the Corrosion of Stainless Steel.
- Experiments were done to assess the effect of water and chloride in TVS (tetravinylsilane) on the corrosion of stainless steel. TVS with different levels of water and chloride were heated in electropolished 316L stainless steel tubes to simulate prolonged storage conditions at room temperature.
- Four samples of TVS with different amounts of water and chloride were heated in separate stainless steel tubes for 7 days at 80° C. One week at 80° C. is intended to simulate the ageing that would normally occur over one year at ambient temperature. For the purpose of this experiment accelerated aging is assumed to follow the Arrhenius principle using the modified 10-degree rule methodology. For any age, at an accelerated aging temperature, the equivalent room temperature age can be estimated by the equation below where trt is the room temperature equivalent age, tAA is the age at the accelerated aging temperature, TAA is the accelerated aging temperature in ° C., Trt is room temperature (22° C.), and Q10 is the reaction rate coefficient that is set to 2 for the current test. A further description of accelerated aging method can be found in ASTM method F1980-07.
-
- Test Sample #1 had low chloride and low water; Sample #2 had low chloride and high water; Sample #3 had high chloride and low water; and Sample #4 had high chloride and high water. These 4 samples of TVS were analyzed for their stainless steel metals content (Fe, Cr, Ni, Mn and Mo) by ICP-MS (inductively coupled plasma-mass spectrometry) before and after heat treatment. These were also analyzed by GC (gas chromatography) before and after heating to assess the impact of ageing on the TVS purity. A summary of these four samples and the analytical results are in Table 3 below.
- No increase in any of the stainless steel metals was observed after ageing TVS Sample #1 (low chloride, low water). This was not the case for TVS Samples #2-4. Increases in Ni, Cr and Mn were observed for the TVS Samples #2-4, all of which had high chloride, high water or high chloride and high water. An increase in the stainless steel metals content after heating is an indication of the corrosion that would occur after storage of the TVS in a stainless steel vessel after one year at room temperature. The overall purity as measured by GC did not change significantly after the heat treatment. No color change was evident before/after ageing of any of the TVS samples, irrespective of the chloride or water content.
- These experiments demonstrate the importance of low chloride and low water in TVS to avoid corrosion of the stainless steel containers which would lead to leaching of the stainless steel metals, such as Fe, Cr, Ni, Mn and Mo, into the TVS liquid.
-
TABLE 3 Summary of analytical results for the 4 test samples. Test Sample # #1 #2 #3 #4 Description low Cl/ low Cl/ high Cl/ high Cl/ low H2O high H2O low H2O high H2O Cl (ppm) 0.1 1.0 79 79 Water (ppm) 28 610 17 2350 GC purity before heat (%) 99.47 99.15 97.96 98.73 GC purity after heat (%) 99.46 99.15 97.95 98.94 Conc before Fe 11 94 24 133 heat (ppb) Cr 1 4 2 6 Ni 1 7 6 10 Mo 0 2 1 1 Mn 0 1 1 1 Avg conc after Fe 10 95 22 122 beat (ppb) Cr 1 9 1 10 Ni 1 53 23 32 Mo 0 2 1 2 Mn 0 3 5 5 Conc. change Fe −1 1 −2 −11 (pps) Cr 0 5 −1 4 Ni 0 46 17 22 Mo 0 0 0 1 Mn 0 2 4 4 - Although certain principles of the disclosure have been described above in connection with aspects or embodiments, it is to be clearly understood that this description is made only by way of example and not as a limitation of the scope of the disclosure.
Claims (13)
1. A system for storing an alkenyl or alkynyl-containing organosilicon compound, the system comprising:
a container, wherein the container permits transmission into the container of no more than 10% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm; and
contained within the container, at least one distilled alkenyl or alkynyl-containing organosilicon compound having a formula RnSiR1 4-n wherein R is selected from the group consisting of a linear or branched C2 to C6 alkenyl group, and a linear or branched C2 to C6 alkynyl group; R1 is selected from the group consisting of hydrogen, a linear or branched C1 to C10 alkyl group, a C3 to C10 cyclic alkyl group, and a C3 to C10 aryl group; and n is 1 to 4.
3. The system of claim 2 , wherein the at least one distilled alkenyl or alkynyl-containing organosilicon compound comprises tetravinylsilane.
4. The system of claim 1 , wherein a stabilizer compound is further contained within the container.
5. The system of claim 4 , wherein the stabilizer compound is selected from the group consisting of 2,6-di-tert-butyl-4-methyl phenol (BHT), 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, propyl ester 3,4,5-trihydroxy-benzoic acid, 2-(1,1-dimethylethyl)-1,4-benzenediol, diphenylpicrylhydrazyl, 4-tert-butylcatechol, N-methylaniline, p-methoxydiphenylamine, diphenylamine, N,N′-diphenyl-p-phenylenediamine, p-hydroxydiphenylamine, phenol, octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, tetrakis (methylene (3,5-di-tert-butyl)-4-hydroxy-hydrocinnamate) methane, phenothiazines, alkylamidonoisoureas, thiodiethylene bis (3,5,-di-tert-butyl-4-hydroxy-hydrocinnamate, 1,2,-bis (3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl) hydrazine, tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, cyclic neopentanetetrayl bis (octadecyl phosphite), 4,4′-thiobis (6-tert-butyl-m-cresol), 2,2′-methylenebis (6-tert-butyl-p-cresol), oxalyl bis (benzylidenehydrazide), raw seed oils, wheat germ oil, tocopherols and gums.
6. The system of claim 1 , wherein the at least one distilled alkenyl or alkynyl-containing organosilicon compound has than 100 ppm (0.01 wt. %) of >1000 amu impurities as determined by Gel Permeation Chromatography (GPC).
7. The system of claim 1 , wherein the container permits transmission into the container of no more than 7% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
8. The system of claim 7 , wherein the container permits transmission into the container of no more than 5% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
9. The system of claim 8 , wherein the container permits transmission into the container of no more than 2% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
10. The system of claim 9 , wherein the container permits transmission into the container of no more than 1% of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
11. The system of claim 10 , wherein the container permits 0% transmission into the container of ultraviolet and visible light having a wavelength of between 290 nm to 450 nm.
12. The system of claim 1 , wherein less than 50 ppm water impurity is contained within the container.
13. The system of claim 1 , wherein less than 10 ppm halide impurity is contained within the container
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18/333,759 US20230339986A1 (en) | 2018-08-23 | 2023-06-13 | Stable alkenyl or alkynyl-containing organosilicon precursor compositions |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201862722090P | 2018-08-23 | 2018-08-23 | |
US16/547,468 US11713328B2 (en) | 2018-08-23 | 2019-08-21 | Stable alkenyl or alkynyl-containing organosilicon precursor compositions |
US18/333,759 US20230339986A1 (en) | 2018-08-23 | 2023-06-13 | Stable alkenyl or alkynyl-containing organosilicon precursor compositions |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/547,468 Division US11713328B2 (en) | 2018-08-23 | 2019-08-21 | Stable alkenyl or alkynyl-containing organosilicon precursor compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
US20230339986A1 true US20230339986A1 (en) | 2023-10-26 |
Family
ID=69584330
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/547,468 Active US11713328B2 (en) | 2018-08-23 | 2019-08-21 | Stable alkenyl or alkynyl-containing organosilicon precursor compositions |
US18/333,759 Pending US20230339986A1 (en) | 2018-08-23 | 2023-06-13 | Stable alkenyl or alkynyl-containing organosilicon precursor compositions |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/547,468 Active US11713328B2 (en) | 2018-08-23 | 2019-08-21 | Stable alkenyl or alkynyl-containing organosilicon precursor compositions |
Country Status (9)
Country | Link |
---|---|
US (2) | US11713328B2 (en) |
EP (1) | EP3841104A4 (en) |
JP (2) | JP7288500B2 (en) |
KR (2) | KR20230167156A (en) |
CN (1) | CN112585146B (en) |
IL (1) | IL280861A (en) |
SG (1) | SG11202100929WA (en) |
TW (2) | TWI781539B (en) |
WO (1) | WO2020041576A1 (en) |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1360469A (en) * | 1962-07-02 | 1964-05-08 | Dow Corning | Stabilization of acryloxypropylmethoxysilanes |
BE787750A (en) * | 1971-08-20 | 1973-02-19 | Union Carbide Corp | PROCESS FOR INHIBITING THE POLYMERIZATION OF ACRYLATES AND METHACRYLATES DURING THEIR DISTILLATION |
JPS60239491A (en) * | 1984-05-15 | 1985-11-28 | Kanegafuchi Chem Ind Co Ltd | Method for stabilizing silicon-containing methacrylic acid ester |
US5138081A (en) * | 1991-04-30 | 1992-08-11 | The Dow Chemical Company | Process for purifying vinylically-unsaturated organosilicon compounds |
US5616753A (en) * | 1995-03-20 | 1997-04-01 | Osi Specialties, Inc. | Stabilizers for unsaturated, polymerizable organosilicon compounds |
DE19616556A1 (en) * | 1996-04-25 | 1997-10-30 | Wacker Chemie Gmbh | Process for the stabilization of hydridic silanes |
JPH11124386A (en) * | 1997-10-17 | 1999-05-11 | Asahi Denka Kogyo Kk | Stabilization of trimethoxysilane |
US7423166B2 (en) * | 2001-12-13 | 2008-09-09 | Advanced Technology Materials, Inc. | Stabilized cyclosiloxanes for use as CVD precursors for low-dielectric constant thin films |
US6858697B2 (en) | 2001-12-21 | 2005-02-22 | Air Products And Chemicals, Inc. | Stabilizers to inhibit the polymerization of substituted cyclotetrasiloxane |
DE10308579B3 (en) * | 2003-02-27 | 2004-06-24 | Wacker-Chemie Gmbh | Stabilization of unsaturated organosilicon compounds, used for e.g. glass fiber size, crosslinker or filler treatment, involves preparation from haloalkylsilane and salt of unsaturated organic acid in presence of alkylene bis(dialkylphenol) |
JP4297708B2 (en) * | 2003-03-25 | 2009-07-15 | 東レ・ダウコーニング株式会社 | Method for distillation of acryloxy group- or methacryloxy group-containing organosilicon compound |
US7124913B2 (en) | 2003-06-24 | 2006-10-24 | Air Products And Chemicals, Inc. | High purity chemical container with diptube and level sensor terminating in lowest most point of concave floor |
JP4479190B2 (en) | 2003-08-22 | 2010-06-09 | 東ソー株式会社 | Insulating film material comprising alkenyl group-containing organosilane compound, insulating film and semiconductor device using the same |
JP2007521242A (en) * | 2003-09-24 | 2007-08-02 | ダウ グローバル テクノロジーズ インコーポレイティド | Metal surfaces that inhibit the polymerization of ethylenically unsaturated monomers |
US20050196974A1 (en) | 2004-03-02 | 2005-09-08 | Weigel Scott J. | Compositions for preparing low dielectric materials containing solvents |
DE102008040475A1 (en) * | 2008-07-16 | 2010-01-21 | Wacker Chemie Ag | Process for preventing the polymerization of unsaturated organosilicon compounds |
ES2910551T3 (en) * | 2008-09-22 | 2022-05-12 | Becton Dickinson Co | A system for coating the interior of a container using a photolysis-assisted chemical vapor deposition method |
DE102009046432A1 (en) * | 2009-11-05 | 2010-07-22 | Wacker Chemie Ag | Preparing organosilicon compounds comprises reacting silicon compounds with Grignard compounds in the presence of tertiary amine compounds |
US8912353B2 (en) * | 2010-06-02 | 2014-12-16 | Air Products And Chemicals, Inc. | Organoaminosilane precursors and methods for depositing films comprising same |
SG10201603129PA (en) | 2011-10-21 | 2016-05-30 | Oerlikon Advanced Technologies Ag | Direct liquid deposition |
JP6766475B2 (en) * | 2016-06-30 | 2020-10-14 | 住友ゴム工業株式会社 | Hollow golf club head |
CN109477214A (en) * | 2016-07-19 | 2019-03-15 | 应用材料公司 | The deposition of flowable silicon-containing film |
CN113717208A (en) * | 2016-09-27 | 2021-11-30 | 中央硝子株式会社 | Method for purifying unsaturated bond-containing silane compound and method for producing the same |
JP7007555B2 (en) * | 2016-09-27 | 2022-02-10 | セントラル硝子株式会社 | Purification method and production method of unsaturated bond-containing silane compound |
JP7172015B2 (en) * | 2017-09-12 | 2022-11-16 | セントラル硝子株式会社 | Additive for non-aqueous electrolyte, electrolyte for non-aqueous electrolyte battery, and non-aqueous electrolyte battery |
US20190376178A1 (en) * | 2018-06-11 | 2019-12-12 | Versum Materials Us, Llc | Compositions and Methods Using Same for Deposition of Silicon-Containing Film |
-
2019
- 2019-08-21 US US16/547,468 patent/US11713328B2/en active Active
- 2019-08-22 WO PCT/US2019/047683 patent/WO2020041576A1/en unknown
- 2019-08-22 CN CN201980055159.4A patent/CN112585146B/en active Active
- 2019-08-22 KR KR1020237041255A patent/KR20230167156A/en not_active Application Discontinuation
- 2019-08-22 EP EP19851299.8A patent/EP3841104A4/en active Pending
- 2019-08-22 SG SG11202100929WA patent/SG11202100929WA/en unknown
- 2019-08-22 KR KR1020217008241A patent/KR102610107B1/en active IP Right Grant
- 2019-08-22 JP JP2021510031A patent/JP7288500B2/en active Active
- 2019-08-23 TW TW110107257A patent/TWI781539B/en active
- 2019-08-23 TW TW108130210A patent/TWI723510B/en active
-
2021
- 2021-02-14 IL IL280861A patent/IL280861A/en unknown
-
2023
- 2023-05-26 JP JP2023087090A patent/JP2023099830A/en active Pending
- 2023-06-13 US US18/333,759 patent/US20230339986A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
WO2020041576A1 (en) | 2020-02-27 |
EP3841104A4 (en) | 2022-05-04 |
TW202009238A (en) | 2020-03-01 |
TWI723510B (en) | 2021-04-01 |
JP2023099830A (en) | 2023-07-13 |
KR20210034111A (en) | 2021-03-29 |
EP3841104A1 (en) | 2021-06-30 |
CN112585146B (en) | 2024-03-22 |
IL280861A (en) | 2021-04-29 |
JP2021534210A (en) | 2021-12-09 |
TW202122404A (en) | 2021-06-16 |
KR20230167156A (en) | 2023-12-07 |
TWI781539B (en) | 2022-10-21 |
US11713328B2 (en) | 2023-08-01 |
CN112585146A (en) | 2021-03-30 |
SG11202100929WA (en) | 2021-02-25 |
JP7288500B2 (en) | 2023-06-07 |
KR102610107B1 (en) | 2023-12-04 |
US20200062787A1 (en) | 2020-02-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7300995B2 (en) | Stabilizers to inhibit the polymerization of substituted cyclotetrasiloxane | |
KR102434249B1 (en) | Compositions and methods for depositing silicon-containing films | |
JP4897510B2 (en) | Method and composition for stabilization of cyclotetrasiloxane | |
US11713328B2 (en) | Stable alkenyl or alkynyl-containing organosilicon precursor compositions | |
US20080042105A1 (en) | Stabilizers To Inhibit The Polymerization of Substituted Cyclotetrasiloxane |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: VERSUM MATERIALS US, LLC, ARIZONA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:RIDGEWAY, ROBERT G.;VRTIS, RAYMOND N.;LEI, XINJIAN;AND OTHERS;SIGNING DATES FROM 20190918 TO 20191009;REEL/FRAME:063932/0565 |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION |