CN1990492A - 用于金属硅氮化物、氧化物或氮氧化物的ALD/CVD的Ti、Ta、Hf、Zr及相关金属硅氨化物 - Google Patents
用于金属硅氮化物、氧化物或氮氧化物的ALD/CVD的Ti、Ta、Hf、Zr及相关金属硅氨化物 Download PDFInfo
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- 229910052751 metal Inorganic materials 0.000 title claims abstract description 59
- 239000002184 metal Substances 0.000 title claims abstract description 59
- -1 silicon amides Chemical class 0.000 title claims abstract description 27
- 229910052719 titanium Inorganic materials 0.000 title claims abstract description 8
- 229910052710 silicon Inorganic materials 0.000 title abstract description 16
- 239000010703 silicon Substances 0.000 title abstract description 16
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 63
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 51
- 229910052581 Si3N4 Inorganic materials 0.000 claims abstract description 30
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 230000000737 periodic effect Effects 0.000 claims abstract description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 4
- 229910052715 tantalum Inorganic materials 0.000 claims abstract description 4
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 13
- 238000005137 deposition process Methods 0.000 claims abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 40
- 238000005516 engineering process Methods 0.000 claims description 39
- 238000005229 chemical vapour deposition Methods 0.000 claims description 37
- 239000002243 precursor Substances 0.000 claims description 29
- 150000001408 amides Chemical class 0.000 claims description 27
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 24
- 229910021529 ammonia Inorganic materials 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 239000003153 chemical reaction reagent Substances 0.000 claims description 15
- 238000000151 deposition Methods 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 13
- 239000010936 titanium Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- KVKAPJGOOSOFDJ-UHFFFAOYSA-N CN(C)[Ta] Chemical compound CN(C)[Ta] KVKAPJGOOSOFDJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 238000000137 annealing Methods 0.000 claims description 5
- 238000000280 densification Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052721 tungsten Chemical group 0.000 claims description 4
- 239000010937 tungsten Chemical group 0.000 claims description 4
- PWVDYRRUAODGNC-UHFFFAOYSA-N CCN([Ti])CC Chemical compound CCN([Ti])CC PWVDYRRUAODGNC-UHFFFAOYSA-N 0.000 claims description 3
- ZLOKVAIRQVQRGC-UHFFFAOYSA-N CN(C)[Ti] Chemical compound CN(C)[Ti] ZLOKVAIRQVQRGC-UHFFFAOYSA-N 0.000 claims description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical group [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 8
- 210000002469 basement membrane Anatomy 0.000 claims 8
- 239000013049 sediment Substances 0.000 claims 7
- MHMBUJVKUFAYFM-UHFFFAOYSA-N C(C)N(C)[Ta] Chemical compound C(C)N(C)[Ta] MHMBUJVKUFAYFM-UHFFFAOYSA-N 0.000 claims 6
- OTSOGXNIABDRQR-UHFFFAOYSA-N C(C)N(CC)[Ta] Chemical compound C(C)N(CC)[Ta] OTSOGXNIABDRQR-UHFFFAOYSA-N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 claims 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 4
- 229910044991 metal oxide Inorganic materials 0.000 claims 4
- IUBCUJZHRZSKDG-UHFFFAOYSA-N C(C)N(C)[Hf] Chemical compound C(C)N(C)[Hf] IUBCUJZHRZSKDG-UHFFFAOYSA-N 0.000 claims 2
- FWDQDBTTXSRLHJ-UHFFFAOYSA-N C(C)N(C)[Zr] Chemical compound C(C)N(C)[Zr] FWDQDBTTXSRLHJ-UHFFFAOYSA-N 0.000 claims 2
- YMDJRROUOWZFPN-UHFFFAOYSA-N C(C)N(CC)[W] Chemical compound C(C)N(CC)[W] YMDJRROUOWZFPN-UHFFFAOYSA-N 0.000 claims 2
- LJWMXWPHTQLTNI-UHFFFAOYSA-N CCN(C)[Ti] Chemical compound CCN(C)[Ti] LJWMXWPHTQLTNI-UHFFFAOYSA-N 0.000 claims 2
- VLYNEXSJZWRPQG-UHFFFAOYSA-N CCN([Hf])CC Chemical compound CCN([Hf])CC VLYNEXSJZWRPQG-UHFFFAOYSA-N 0.000 claims 2
- DVOBFBBUJSCXOR-UHFFFAOYSA-N CCN([Zr])CC Chemical compound CCN([Zr])CC DVOBFBBUJSCXOR-UHFFFAOYSA-N 0.000 claims 2
- YWATTXMDZQWERV-UHFFFAOYSA-N CN(C)[Hf] Chemical compound CN(C)[Hf] YWATTXMDZQWERV-UHFFFAOYSA-N 0.000 claims 2
- PTDGQDJPIFTKJL-UHFFFAOYSA-N CN(C)[W] Chemical compound CN(C)[W] PTDGQDJPIFTKJL-UHFFFAOYSA-N 0.000 claims 2
- PULVCHXDNLGASZ-UHFFFAOYSA-N CN(C)[Zr] Chemical compound CN(C)[Zr] PULVCHXDNLGASZ-UHFFFAOYSA-N 0.000 claims 2
- SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 claims 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 2
- PPJPTAQKIFHZQU-UHFFFAOYSA-N bis(tert-butylimino)tungsten;dimethylazanide Chemical compound C[N-]C.C[N-]C.CC(C)(C)N=[W]=NC(C)(C)C PPJPTAQKIFHZQU-UHFFFAOYSA-N 0.000 claims 2
- 239000006227 byproduct Substances 0.000 claims 2
- ZYLGGWPMIDHSEZ-UHFFFAOYSA-N dimethylazanide;hafnium(4+) Chemical compound [Hf+4].C[N-]C.C[N-]C.C[N-]C.C[N-]C ZYLGGWPMIDHSEZ-UHFFFAOYSA-N 0.000 claims 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 2
- 230000008676 import Effects 0.000 claims 2
- 238000010926 purge Methods 0.000 claims 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical group [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 2
- GMNCNDKLAZDHRJ-UHFFFAOYSA-N C(C)N(C)[W] Chemical compound C(C)N(C)[W] GMNCNDKLAZDHRJ-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical group [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- 125000006309 butyl amino group Chemical group 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 239000011733 molybdenum Chemical group 0.000 claims 1
- 229910052758 niobium Inorganic materials 0.000 claims 1
- 239000010955 niobium Chemical group 0.000 claims 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical group [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052814 silicon oxide Inorganic materials 0.000 abstract 1
- 239000010408 film Substances 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 150000004767 nitrides Chemical class 0.000 description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000004062 sedimentation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- 229910007991 Si-N Inorganic materials 0.000 description 3
- 229910006294 Si—N Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910000474 mercury oxide Inorganic materials 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- AWFPGKLDLMAPMK-UHFFFAOYSA-N dimethylaminosilicon Chemical compound CN(C)[Si] AWFPGKLDLMAPMK-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
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- 239000011229 interlayer Substances 0.000 description 1
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- 238000001819 mass spectrum Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000012686 silicon precursor Substances 0.000 description 1
- DVHMVRMYGHTALQ-UHFFFAOYSA-N silylhydrazine Chemical compound NN[SiH3] DVHMVRMYGHTALQ-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
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- 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
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
-
- 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 Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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 Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
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- 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 Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/005—Compounds of elements of Group 5 of the Periodic Table without metal-carbon linkages
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Abstract
本发明涉及用于金属硅氮化物、氧化物或氮氧化物的ALD/CVD的Ti、Ta、Hf、Zr及相关金属硅氨化物，具体而言，所述金属硅氨化物为一种由下列结构表示的有机金属络合物：其中M是选自元素周期表4族的金属，R1－4可以相同或不同，选自二烷基酰胺、二氟代烷基酰胺、氢、烷基、烷氧基、氟代烷基和烷氧基、环脂族基和芳基，额外条件是当R1和R2是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷基和烷氧基时，它们可以连接成环。也公开了相关的化合物。还包括使用该络合物的CVD和ALD工艺。
Description
相关申请的交叉参考
本申请要求2005年10月7日提交的美国临时申请No.60/724,757的利益。在此合并该临时申请公开的内容作为参考。
技术领域
本发明涉及集成电路的制备中的铜扩散阻挡层，其用于避免在制备金属线(metal line)的沉积和后续处理过程中作为金属线沉积到绝缘层和其他层、特征和半导体材料中的铜或其他金属的迁移。本发明还涉及半导体工业中作为电极或介电层的薄膜。
发明内容
本发明是下列结构表示的有机金属络合物(complex)：
其中M是选自元素周期表4族的金属，R1-4可以相同或不同，选自二烷基酰胺、二氟代烷基酰胺、氢、烷基、烷氧基、氟代烷基和烷氧基、氟代烷氧基、环脂族基以及芳基，额外条件是当R1和R2是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷基或烷氧基或氟代烷氧基时，它们可以连接成环。
在优选实施方案中，本发明是下式表示的双(N，N’-二(叔丁基)-二氨基甲硅烷基)钛。
下列结构表示的有机金属络合物：
其中M是选自元素周期表4族的金属，R5-10可以相同或不同，选自氢、烷基、烷氧基、氟代烷基和烷氧基、氟代烷氧基、环脂族基以及芳基，额外条件是当R5、R6、R9和R10是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷基烷氧基或氟代烷氧基时，它们可以连接成环。
下列结构表示的有机金属络合物：
其中M是选自元素周期表5族的金属，R11-16可以相同或不同，选自氢、烷基、烷氧基、氟代烷基和烷氧基、氟代烷氧基、环脂族基以及芳基；n＝1，2，m＝5-2n，其中当R11、R12、R15和R16是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基、氟代烷基或烷氧基时，它们可以连接成环。
下列结构表示的有机金属络合物：
其中M是选自元素周期表6族的金属，R17-22可以相同或不同，选自氢、烷基、烷氧基、氟代烷基和烷氧基、环脂族基以及芳基；p＝1，2，3，q＝6-2p，其中当R17、R18、R21和R22是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基、氟代烷基或烷氧基时，它们可以连接成环。
也期望使用这些络合物的化学气相沉积(CVD)和原子层沉积(ALD)工艺。
附图说明
图1是用于含钛硅氮化物膜的CVD或ALD的双(N，N’二(叔丁基)-二氨基甲硅烷基)钛单晶体结构。
图2是双(N，N’-二(叔丁基)-二氨基甲硅烷基)钛的热重分析(TGA)图。几乎全部的重量损失表明它是易挥发的以及在典型CVD或ALD工艺中可容易地释放到反应室中。因此，有和没有氨或其他合适的含氮试剂时它是合适的制备含钛硅氮化物膜的前体。
图3示出有和没有氨时，沉积压力为1.5托，He载气流速为46sccm，作为基底温度函数的Ti-Si-N膜的沉积速率(/min)。
图4示出了在各种温度的钛硅氮化物膜的组成。通过使用Ti(H2Si(NBUt) 2)2作为有机金属前体由化学气相沉积形成钛硅氮化物膜。
具体实施方式
由于铜良好的电导率和高电迁移阻抗，它现在有效地替代铝作为半导体逻辑器件的互连金属。然而，铜可以快速并破坏性地扩散通过器件中其他材料例如硅或层间电介质从而导致最终产物中电功能失调。由于这些原因有必要使用扩散阻挡层封装铜。金属氮化物和金属硅氮化物薄膜是用于这些扩散阻挡层的备选材料。它们也可以作为栅极材料在接近晶体管的硅表面使用，在此它们不会对硅产生污染并可在较高温度下处理。使用金属氮化物层，例如，氮化钛(TiN)层作为阻挡层来阻挡在半导体器件结构例如触点、通路和沟槽中的扩散，包括铜扩散。然而，由于期望阻挡层对铜互联尽可能提供最小的额外电阻，因此阻挡层必须是相当薄的以适应当前器件的高纵横比。这些阻挡层必须是化学惰性的并必须阻挡相邻材料相互扩散通过它，具有低电阻率(显示高导电性)、低接触或通道电阻和低结漏电(junction leakage)。
金属氮化物趋向于具有晶体结构的金属化合物，而金属氮化物/硅氮化物膜趋向为非晶态的。在前者的情况中，由于铜扩散可能沿着它的晶粒边界发生，因此膜的结晶度可以提供其阻挡层性能的击穿。在后者的情况中，由于材料是非晶态的，没有晶粒边界因此改善了阻挡性能。可选择地，在金属氮化物中硅氮化物成分用于阻断(block)晶粒边界。
然而，随着更多的硅氮化物添加到金属氮化物中以获得这种非晶特性，材料的电阻增加，因此需要小心控制硅氮化物的含量。典型地这些阻挡薄膜必须长成为能够在具有精确控制的膜厚度的硅片上均匀涂覆深度蚀刻特征的高保形(conformal)薄膜。这些特征最终填充铜从而在硅片表面晶体管器件之间提供互联电通道。经常使用化学气相沉积(“CVD”)使这些膜生长成保形薄膜，但是由于器件的尺寸连续缩小，需要阻挡膜的厚度是10埃数量级。在这一点上，CVD面临挑战，而原子层沉积(“ALD”)变得更有吸引力。在任何情况下，都需要挥发性金属化合物作为前体。对于金属氮化物膜，例如可以使用氮化钛、氮化钽或氮化钨、金属氨基或氨基/亚氨基化合物(metal amide or amide/imidecompound)。在ALD或CVD工艺中，这些化合物与如氨等合适的试剂反应来沉积金属氮化物。CVD工艺的实例，是使用前体四(二乙基氨基)钛与氨反应得到TiN。可选择地，在CVD工艺中前体可以在晶片表面上热分解得到碳氮化钛材料的连续薄膜，之后用氢/氮等离子体退火以致密化膜并降低碳的含量从而得到主要为氮化钛的膜。
用于后者工艺的合适的前体实例是四(二甲基氨基)钛。可选择地，可以在ALD工艺中使用前体五(二甲基氨基)钽与氨反应的ALD工艺中生长氮化钽膜。可选择地，可以通过使用前体(ButN＝)2W(NMe2)2与氨在交替循环中反应生长氮化钨膜。如果将氮化硅导入到这些膜中，通常通过金属氮化物前体和氮化硅前体，例如硅烷或如四(二甲基氨基)硅等硅酰胺化合物，共同反应来实现。因此，含金属(M)的前体、含硅的前体和如氨等氮源共同反应得到MSiN膜。因此，硅的掺入程度在一定程度上依赖于工艺中精确控制硅前体的计量的能力。
当前在三重膜的形成中，通过循环沉积依次在基底上沉积金属氨化物(metalamide)、硅烷和氨，但是该工艺产生处理问题。硅烷是自燃气体，产生潜在的安全隐患。另外，在循环工艺中使用三种前体需要三个沉积步骤以及各自的清洗步骤。另一方面，据报道可以使用氨基硅烷或肼基硅烷与氨形成氮化硅。重要地，尽管已发现这些膜中通过化学气相沉积或原子层沉积形成的金属硅氮化物中没有直接金属-硅键，暗示在得到的膜中金属氮化物和氮化硅是独立的相，即用金属氮化物被氮化硅填充。对于生长MSiN膜，本发明是可能地更好方法，其使用已经在其结构中具有金属和硅两者的前体，从而使得这两种元素以精确固定比例在相同分子中输送，尽管在由处理这种前体得到的膜中，金属与硅的精确比例也可以作为精确工艺条件如压力、温度、能量输入和流出的函数来控制。通过下面提及的几个非限定性实施例阐述本发明。
实施例1：双(N，N’-二(叔丁基)-二氨基甲硅烷基)钛、Ti(H2Si(NBut)2)2的合成
在干燥的氮气气氛中，将7.0克(40mmole)的双(四丁基氨基)硅烷溶于100毫升无水四氢呋喃溶剂中并冷却至-78℃。将32.0毫升(840mmole)的2.5M的在已烷中的正丁基锂在10分钟内逐滴加入到该溶液中，在-78℃搅拌得到的混合物额外30分钟从而形成白色沉淀。然后将这种混合物加热到室温额外20分钟，之后再次将其冷却至-78℃。在氮气气氛下缓慢地将2.14毫升(10mmole)四氯化钛加入到含10毫升无水四氢呋喃的单独容器中从而形成黄色沉淀。然后在-78℃下将后来得到的沉淀加入到首次得到的沉淀中，然后加热到室温并搅拌过夜。然后在真空中完全除去四氢呋喃和已烷溶剂并在氮气气氛下将得到的黄-绿色固体与100毫升新鲜的无水已烷混合，过滤得到的混合物并在动态真空下将得到的绿色油状物加热到110℃并蒸馏提取橙色固体到用液氮冷却的收集容器中，产量＝3.6克(45％)。然后通过在65-70℃升华进一步提纯粗产物。通过单晶X-射线分析(参见图1)确定结构。
1H NMR：(500MHz，C6D6)：δ＝1.35(s，36H)，δ＝5.41(s，4H).
13C NMR：(500MHz，C6D6)：δ＝35.25(s，12C)，δ＝58.97(s，4C).
质谱在387m/z显示强峰(即393m/z母体减去15m/z的CH3)。
还可以使用可选择的合成，其中在-78℃下将双(四丁基氨基)硅烷二价阳离子的两种等价物添加到已烷或无水四氢呋喃中的四氯化钛中，并且如上述处理得到的混合物。
图2是双(N，N’-二(叔丁基)-二氨基甲硅烷基)钛的热重分析(TGA)图。几乎全部的重量损失表明它是易挥发的并能在典型CVD或ALD工艺中容易地输送到反应室中。因此，有和没有氨或其他合适的含氮试剂时，它是合适的制备含钛硅氮化物的膜的前体。
实施例2：HSi(NMe2)(ButN)2Ti(NMe2)2的合成
在干燥的氮气气氛中，将3.48克(20mmole)的双(四丁基氨基)硅烷溶于100毫升无水四氢呋喃溶剂中并冷却至-78℃。将24.4毫升(40mmole)的1.6M的在己烷中的正丁基锂在10分钟内逐滴加入到该溶液中，并且在-78℃搅拌得到的混合物额外30分钟从而形成白色沉淀。然后将这种混合物加热到室温额外20分钟，之后再次将其冷却至-78℃。在氮气气氛下缓慢地将0.55毫升(5mmole)四氯化钛加入到含10毫升无水四氢呋喃的单独容器中形成黄色沉淀。然后在-78℃下将这种钛沉淀加入到锂化的混合物中。维持在-78℃下将20克(20mmole)5wt％二甲基氨基锂加入到这种混合物中。然后将得到的混合物加热到室温并搅拌一夜。然后除去溶剂并在氮气气氛下将得到的粗产物与100毫升无水已烷混合，在真空下过滤从而除去已烷。然后在动态真空下将得到的油状物加热到110℃并蒸馏提取橙色固体到用液氮冷却的收集容器中。然后通过在60℃真空升华提纯该橙色产物。
实施例3：通过使用Ti(H2Si(NBut)2)2作为有机金属前体由CVD工艺形成Ti-Si-N膜
使用已知的CVD技术在常规的CVD装置中使用Ti(H2Si(NBUt)2)2作为有机金属前体用于形成金属硅氮化物膜。
在90℃在鼓泡器中蒸发Ti(H2Si(NBut)2)2并输送到CVD室中与有和没有NH3的含氮源混合。CVD室是具有热基底夹持架的冷壁系统。基底维持在400℃到500℃范围内的温度。室压维持在1到2托。
图3示出在沉积压力为1.5托，He载气流速为46sccm时，作为基底温度函数的Ti-Si-N膜的沉积速率。NH3的流速范围是0sccm(没有NH3)到75sccm。沉积速率随着基底温度的提高而提高。无NH3沉积的沉积速率最低，表明NH3的存在促进钛硅氮化物膜的形成。
在各种温度下用NH3作为含氮源沉积的钛硅氮化物膜的EDX分析表明膜含有钛、硅和氮原子(如图4所示)。
Claims (34)
1、一种由下列结构表示的有机金属络合物：
其中M是选自元素周期表4族的金属，R1-4可以相同或不同，选自二烷基酰胺、二氟代烷基酰胺、氢、烷基、烷氧基、氟代烷氧基、氟代烷基和烷氧基、环脂族基以及芳基，额外条件是当R1和R2是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环。
2、根据权利要求1的有机金属络合物，其中M选自钛、锆和铪。
3、根据权利要求1的有机金属络合物，包括双(N，N’-二(叔丁基)-二氨基甲硅烷基)钛。
4、一种在基底上形成保形金属硅氮化物薄膜的沉积工艺，其中将权利要求1的有机金属络合物引入到沉积室、气化并沉积在基底上。
5、根据权利要求4的沉积工艺，其选自原子层沉积(ALD)工艺和化学气相沉积(CVD)工艺，任选使用氨。
6、一种ALD或CVD工艺，其使用根据权利要求1的前体与选自氨、肼、二甲基肼和氮的含氮试剂反应以形成金属硅氮化物基膜，反应条件选自热、等离子体、远程等离子体和其他供能环境(energizing environment)。
7、一种ALD或CVD工艺，其使用根据权利要求1的前体与选自氧化剂以及含氧化剂和含氮试剂的混合物的试剂反应以形成金属硅氧化物或氮氧化物基膜，反应条件选自热、等离子体、远程等离子体和其他供能环境。
8、根据权利要求4的工艺，其使用额外处理步骤用于最后的膜致密化或膜退火，选自热、臭氧、等离子体、UV和微波。
9、一种由下列结构表示的有机金属络合物：
其中M是选自元素周期表4族的金属，R5-10可以相同或不同，选自氢、烷基、烷氧基、氟代烷基烷氧基、氟代烷氧基、环脂族基以及芳基，额外条件是当R5、R6、R9和R10是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环。
10、根据权利要求9的有机金属络合物，其中M选自钛、锆和铪。
11、一种在基底上形成保形金属硅氮化物薄膜的沉积工艺，其中将权利要求9的有机金属络合物引入到沉积室、气化并沉积在基底上。
12、根据权利要求11的沉积工艺，其选自原子层沉积(ALD)工艺和化学气相沉积(CVD)工艺，任选使用氨。
13、一种ALD或CDV工艺，其中根据权利要求9的前体与选自氨、肼、二甲基肼和氮的含氮试剂反应以形成金属硅氮化物基膜，反应条件选自热、等离子体、远程等离子体和其他供能环境。
14、一种ALD或CVD工艺，其中根据权利要求9的前体与选自氧化剂以及氧化剂和含氮试剂的混合物的试剂反应以形成金属硅氧化物或氮氧化物基膜，反应条件选自热、等离子体、远程等离子体和其他供能环境。
15、根据权利要求11的工艺，其使用额外处理步骤用于最后的膜致密化或膜退火，选自热、臭氧、等离子体、UV和微波。
16、一种由下列结构表示的有机金属络合物：
其中M是选自元素周期表5族的金属，R11-16可以相同或不同，选自氢、烷基、烷氧基、氟代烷氧基、氟代烷基和环脂族基以及芳基；n＝1，2，m＝5-2n，其中当R11、R12、R15和R16是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环。
17、根据权利要求16的有机金属络合物，其中M选自钒、铌和钽。
18、一种在基底上形成保形金属硅氮化物薄膜的沉积工艺，其中将权利要求16的有机金属络合物引入到沉积室、气化并沉积在基底上。
19、根据权利要求18的沉积工艺，其选自原子层沉积(ALD)工艺和化学气相沉积(CVD)工艺，任选使用氨。
20、一种ALD或CVD工艺，其中根据权利要求16的前体与选自氨、肼、二甲基肼和氮的含氮试剂反应以形成金属硅氮化物基膜，反应条件选自热、等离子体、远程等离子体和其他供能环境。
21、一种ALD或CVD工艺，其中根据权利要求16的前体与选自氧化剂以及氧化剂和含氮试剂的混合物的试剂反应以形成金属硅氧化物或氮氧化物基膜，反应条件选自热、等离子体、远程等离子体和其他供能环境。
22、根据权利要求18的工艺，其使用额外处理步骤用于最后的膜致密化或膜退火，选自热、臭氧、等离子体、UV和微波。
23、一种由下列结构表示的有机金属络合物：
其中M是选自元素周期表6族的金属，R17-22可以相同或不同，选自氢、烷基、烷氧基、氟代烷基和烷氧基、环脂族基以及芳基；p＝1，2，3，q＝6-2p，其中当R17、R18、R21和R22是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环。
24、根据权利要求23的有机金属络合物，其中M选自铬、钼和钨。
25、一种在基底上形成保形金属硅氮化物薄膜的沉积工艺，其中将权利要求23的有机金属络合物引入到沉积室、气化并沉积在基底上。
26、根据权利要求25的沉积工艺，其选自原子层沉积(ALD)工艺和化学气相沉积(CVD)工艺，任选使用氨。
27、一种ALD或CVD工艺，其中根据权利要求23的前体与选自氨、肼、二甲基肼和氮的含氮试剂反应以形成金属硅氮化物基膜，反应条件选自热、等离子体、远程等离子体和其他供能环境。
28、一种ALD或CVD工艺，其中根据权利要求23的前体与选自氧化剂以及氧化剂和含氮试剂的混合物的试剂反应来形成金属硅氧化物或氮氧化物基膜，反应条件选自热、等离子体、远程等离子体和其他供能环境。
29、一种在基底上形成金属硅氮化物膜的循环沉积工艺，包括以下步骤：
将有机金属前体导入到沉积室中并在加热的基底上沉积膜；
吹扫沉积室以除去未反应的有机金属前体和任何副产物；
导入金属氨化物以在加热的基底上沉积膜；
吹扫沉积室以除去任何未反应的金属氨化物和副产物；以及
重复循环沉积工艺直到形成期望的膜厚度。
30、根据权利要求29的工艺，其中有机金属络合物选自以下物质：
其中M是选自元素周期表4族的金属，R1-4可以相同或不同，选自二烷基酰胺、二氟代烷基酰胺、氢、烷基、烷氧基、氟代烷氧基、氟代烷基和烷氧基、环脂族基以及芳基，额外条件是当R1和R2是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环；
其中M是选自元素周期表4族的金属，R5-10可以相同或不同，选自氢、烷基、烷氧基、氟代烷基烷氧基、氟代烷氧基、环脂族基以及芳基，额外条件是当R5、R6、R9和R10是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环；
其中M是选自元素周期表5族的金属，R11-16可以相同或不同，选自氢、烷基、烷氧基、氟代烷氧基、氟代烷基和环脂族基以及芳基；n＝1，2，m＝5-2n，其中当R11、R12、R15和R16是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环；以及
(d)
其中M是选自元素周期表6族的金属，R17-22可以相同或不同，选自氢、烷基、烷氧基、氟代烷基和烷氧基、环脂族基以及芳基；p＝1，2，3，q＝6-2p，其中当R17、R18、R21和R22是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环。
31、根据权利要求29的工艺，其中金属氨化物选自四(二甲基氨基)钛(TDMAT)、四(二乙基氨基)钛(TDEAT)、四(乙基甲基氨基)钛(TEMAT)、四(二甲基氨基)锆(TDMAZ)、四(二乙基氨基)锆(TDEAZ)、四(乙基甲基氨基)锆(TEMAZ)、四(二甲基氨基)铪(TDMAH)、四(二乙基氨基)铪(TDEAH)、四(乙基甲基氨基)铪(TEMAH)、叔丁基亚氨基三(二乙基氨基)钽(TBTDET)、叔丁基亚氨基三(二甲基氨基)钽(TBTDMT)、叔丁基亚氨基三(乙基甲基氨基)钽(TBTEMT)、乙基亚氨基三(二乙基氨基)钽(EITDET)、乙基亚氨基三(二甲基氨基)钽(EITDMT)、乙基亚氨基三(乙基甲基氨基)钽(EITEMT)、叔戊基亚氨基三(二甲基氨基)钽(TAIMAT)、叔戊基亚氨基三(二乙基氨基)钽、五(二甲基氨基)钽、叔戊基亚氨基三(乙基甲基氨基)钽、双(叔丁基亚氨基)双(二甲基氨基)钨(BTBMW)、双(叔丁基亚氨基)双(二乙基氨基)钨、双(叔丁基亚氨基)双(乙基甲基氨基)钨及其混合物。
32、根据权利要求29的工艺，选自原子层沉积(ALD)工艺和化学气相沉积(CVD)工艺，任选使用氨。
33、根据权利要求29的工艺，其使用额外的处理步骤用于最终膜致密化和膜退火，选自热、臭氧、等离子体、UV和微波。
34、一种任选使用氨的CVD工艺，使用以下物质的混合物：
(A)选自以下的前体
其中M是选自元素周期表4族的金属，R1-4可以相同或不同，选自二烷基酰胺、二氟代烷基酰胺、氢、烷基、烷氧基、氟代烷氧基、氟代烷基和烷氧基、环脂族基以及芳基，额外条件是当R1和R2是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环；
其中M是选自元素周期表4族的金属，R5-10可以相同或不同，选自氢、烷基、烷氧基、氟代烷基烷氧基、氟代烷氧基、环脂族基以及芳基，额外条件是当R5、R6、R9和R10是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环；
其中M是选自元素周期表5族的金属，R11-16可以相同或不同，选自氢、烷基、烷氧基、氟代烷氧基、氟代烷基和环脂族基以及芳基；n＝1，2，m＝5-2n，其中当R11、R12、R15和R16是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环；和
其中M是选自元素周期表6族的金属，R17-22可以相同或不同，选自氢、烷基、烷氧基、氟代烷基和烷氧基、环脂族基以及芳基；p＝1，2，3，q＝6-2p，其中当R17、R18、R21和R22是二烷基酰胺、二氟代烷基酰胺、烷氧基、氟代烷氧基或氟代烷基时，它们可以连接成环；
(B)金属氨化物，选自四(二甲基氨基)钛(TDMAT)、四(二乙基氨基)钛(TDEAT)、四(乙基甲基氨基)钛(TEMAT)、四(二甲基氨基)锆(TDMAZ)、四(二乙基氨基)锆(TDEAZ)、四(乙基甲基氨基)锆(TEMAZ)、四(二甲基氨基)铪(TDMAH)、四(二乙基氨基)铪(TDEAH)、四(乙基甲基氨基)铪(TEMAH)、叔丁基亚氨基三(二乙基氨基)钽(TBTDET)、叔丁基亚氨基三(二甲基氨基)钽(TBTDMT)、叔丁基亚氨基三(乙基甲基氨基)钽(TBTEMT)、乙基亚氨基三(二乙基氨基)钽(EITDET)、乙基亚氨基三(二甲基氨基)钽(EITDMT)、乙基亚氨基三(乙基甲基氨基)钽(EITEMT)、叔戊基亚氨基三(二甲基氨基)钽(TAIMAT)、叔戊基亚氨基三(二乙基氨基)钽、五(二甲基氨基)钽、叔戊基亚氨基三(乙基甲基氨基)钽、双(叔丁基亚氨基)双(二甲基氨基)钨(BTBMW)、双(叔丁基亚氨基)双(二乙基氨基)钨、双(叔丁基氨基)双(乙基甲基亚氨基)钨及其混合物。
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| US11/522,768 US7754906B2 (en) | 2005-10-07 | 2006-09-18 | Ti, Ta, Hf, Zr and related metal silicon amides for ALD/CVD of metal-silicon nitrides, oxides or oxynitrides |
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| US6403465B1 (en) * | 1999-12-28 | 2002-06-11 | Taiwan Semiconductor Manufacturing Company | Method to improve copper barrier properties |
| JP3819660B2 (ja) | 2000-02-15 | 2006-09-13 | 株式会社日立国際電気 | 半導体装置の製造方法および半導体製造装置 |
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| AR038680A1 (es) | 2002-02-19 | 2005-01-26 | Synthes Ag | Implante intervertebral |
| US6846516B2 (en) * | 2002-04-08 | 2005-01-25 | Applied Materials, Inc. | Multiple precursor cyclical deposition system |
| US6875271B2 (en) * | 2002-04-09 | 2005-04-05 | Applied Materials, Inc. | Simultaneous cyclical deposition in different processing regions |
| US20040009336A1 (en) * | 2002-07-11 | 2004-01-15 | Applied Materials, Inc. | Titanium silicon nitride (TISIN) barrier layer for copper diffusion |
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2006
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- 2006-09-30 CN CN2006101444378A patent/CN1990492B/zh not_active Expired - Fee Related
- 2006-10-03 EP EP06255104A patent/EP1772460B1/en not_active Not-in-force
- 2006-10-03 DE DE602006005877T patent/DE602006005877D1/de active Active
- 2006-10-03 AT AT06255104T patent/ATE426606T1/de not_active IP Right Cessation
- 2006-10-03 TW TW095136762A patent/TWI336732B/zh active
- 2006-10-04 KR KR1020060097693A patent/KR100862263B1/ko active IP Right Grant
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102027603B (zh) * | 2007-09-26 | 2013-11-20 | 伊斯曼柯达公司 | 沉积有机材料的方法 |
| US10533023B2 (en) | 2013-06-28 | 2020-01-14 | Wayne State University | Bis(trimethylsilyl) six-membered ring systems and related compounds as reducing agents for forming layers on a substrate |
| CN106544001A (zh) * | 2016-10-21 | 2017-03-29 | 河南大学 | 一种耐温性好的胍胶压裂液纳米交联剂及其制备方法 |
| CN106544001B (zh) * | 2016-10-21 | 2019-12-31 | 河南大学 | 一种耐温性好的胍胶压裂液纳米交联剂及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1772460A1 (en) | 2007-04-11 |
| JP2007131616A (ja) | 2007-05-31 |
| US20070082500A1 (en) | 2007-04-12 |
| US7754906B2 (en) | 2010-07-13 |
| JP5118169B2 (ja) | 2013-01-16 |
| KR100862263B1 (ko) | 2008-10-09 |
| CN1990492B (zh) | 2011-06-08 |
| TWI336732B (en) | 2011-02-01 |
| EP1772460B1 (en) | 2009-03-25 |
| KR20070038914A (ko) | 2007-04-11 |
| DE602006005877D1 (de) | 2009-05-07 |
| JP4555272B2 (ja) | 2010-09-29 |
| JP2010222362A (ja) | 2010-10-07 |
| ATE426606T1 (de) | 2009-04-15 |
| TW200714738A (en) | 2007-04-16 |
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