TWI588151B - 由有機釕化合物構成的化學蒸鍍用原料及使用該化學蒸鍍用原料之化學蒸鍍法 - Google Patents
由有機釕化合物構成的化學蒸鍍用原料及使用該化學蒸鍍用原料之化學蒸鍍法 Download PDFInfo
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- TWI588151B TWI588151B TW104132178A TW104132178A TWI588151B TW I588151 B TWI588151 B TW I588151B TW 104132178 A TW104132178 A TW 104132178A TW 104132178 A TW104132178 A TW 104132178A TW I588151 B TWI588151 B TW I588151B
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- 238000005229 chemical vapour deposition Methods 0.000 title claims description 31
- 239000002994 raw material Substances 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 19
- 150000001875 compounds Chemical class 0.000 title description 25
- -1 pentadienyl Chemical group 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 150000003304 ruthenium compounds Chemical class 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052715 tantalum Inorganic materials 0.000 claims description 7
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 3
- 230000008016 vaporization Effects 0.000 claims description 2
- 239000010408 film Substances 0.000 description 44
- 238000000354 decomposition reaction Methods 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 11
- 238000005755 formation reaction Methods 0.000 description 11
- 229910052707 ruthenium Inorganic materials 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000000231 atomic layer deposition Methods 0.000 description 3
- 229910000420 cerium oxide Inorganic materials 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 description 3
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- YFYOYTXPSRDFQB-UHFFFAOYSA-N CC(=C[Ru]C1=C(C(=CCC1(C)C)CC)C)C=C(C)C Chemical compound CC(=C[Ru]C1=C(C(=CCC1(C)C)CC)C)C=C(C)C YFYOYTXPSRDFQB-UHFFFAOYSA-N 0.000 description 2
- UQOAEOAWAAMSML-UHFFFAOYSA-N CC(=C[Ru]C1=C(C=C(CC1(C)C)C)C)C=C(C)C Chemical compound CC(=C[Ru]C1=C(C=C(CC1(C)C)C)C)C=C(C)C UQOAEOAWAAMSML-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- RADGOBKLTHEUQO-UHFFFAOYSA-N ruthenium(4+) Chemical compound [Ru+4] RADGOBKLTHEUQO-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LXQPBCHJNIOMQU-UHFFFAOYSA-N 2,4-dimethylpent-1-ene Chemical compound CC(C)CC(C)=C LXQPBCHJNIOMQU-UHFFFAOYSA-N 0.000 description 1
- OXJUCLBTTSNHOF-UHFFFAOYSA-N 5-ethylcyclopenta-1,3-diene;ruthenium(2+) Chemical compound [Ru+2].CC[C-]1C=CC=C1.CC[C-]1C=CC=C1 OXJUCLBTTSNHOF-UHFFFAOYSA-N 0.000 description 1
- HDWDVUXQIOWBEP-UHFFFAOYSA-N C(C)C1(C=CC=C1)[Ru] Chemical compound C(C)C1(C=CC=C1)[Ru] HDWDVUXQIOWBEP-UHFFFAOYSA-N 0.000 description 1
- JIAUFQXJLHVZEF-UHFFFAOYSA-N CC(=C[Ru]C1=C(C=CCC1(C)C)C)C=C(C)C Chemical compound CC(=C[Ru]C1=C(C=CCC1(C)C)C)C=C(C)C JIAUFQXJLHVZEF-UHFFFAOYSA-N 0.000 description 1
- MXKMPPKIDDYUKU-UHFFFAOYSA-N CC1(C)CC=CC(C)=C1[Ru]C1=C(C)C=CCC1(C)C Chemical compound CC1(C)CC=CC(C)=C1[Ru]C1=C(C)C=CCC1(C)C MXKMPPKIDDYUKU-UHFFFAOYSA-N 0.000 description 1
- DFKXMNBINMIQFU-UHFFFAOYSA-N CC1=C(C(CC(=C1)C)(C)C)[Ru+] Chemical compound CC1=C(C(CC(=C1)C)(C)C)[Ru+] DFKXMNBINMIQFU-UHFFFAOYSA-N 0.000 description 1
- NOAYLKZHHDROFC-UHFFFAOYSA-N CC1=C(C(CC=C1)(C)C)C2=C(C=CC3=C2CC4=CC=CC=C43)C=C(C)C=C(C)C Chemical compound CC1=C(C(CC=C1)(C)C)C2=C(C=CC3=C2CC4=CC=CC=C43)C=C(C)C=C(C)C NOAYLKZHHDROFC-UHFFFAOYSA-N 0.000 description 1
- WEMUQDNXQWNCIF-UHFFFAOYSA-N CC1=C(C(CC=C1)(C)C)[Ru+] Chemical compound CC1=C(C(CC=C1)(C)C)[Ru+] WEMUQDNXQWNCIF-UHFFFAOYSA-N 0.000 description 1
- BOQKGWFIYQVXMG-UHFFFAOYSA-N CCC([Ru]C(CC)=CC=CC)=CC=CC Chemical compound CCC([Ru]C(CC)=CC=CC)=CC=CC BOQKGWFIYQVXMG-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000004024 organic sulfonium compounds Chemical class 0.000 description 1
- 150000002908 osmium compounds Chemical class 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003482 tantalum compounds Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- ZTWIEIFKPFJRLV-UHFFFAOYSA-K trichlororuthenium;trihydrate Chemical compound O.O.O.Cl[Ru](Cl)Cl ZTWIEIFKPFJRLV-UHFFFAOYSA-K 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/06—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material
- C23C16/18—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material from metallo-organic compounds
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
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- C07F17/00—Metallocenes
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- C09D1/00—Coating compositions, e.g. paints, varnishes or lacquers, based on inorganic substances
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- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/44—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating
- C23C16/448—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating characterised by the method used for generating reactive gas streams, e.g. by evaporation or sublimation of precursor materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/28—Manufacture of electrodes on semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/268
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/28—Manufacture of electrodes on semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/268
- H01L21/283—Deposition of conductive or insulating materials for electrodes conducting electric current
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- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/28—Manufacture of electrodes on semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/268
- H01L21/283—Deposition of conductive or insulating materials for electrodes conducting electric current
- H01L21/285—Deposition of conductive or insulating materials for electrodes conducting electric current from a gas or vapour, e.g. condensation
- H01L21/28506—Deposition of conductive or insulating materials for electrodes conducting electric current from a gas or vapour, e.g. condensation of conductive layers
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- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/28—Manufacture of electrodes on semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/268
- H01L21/283—Deposition of conductive or insulating materials for electrodes conducting electric current
- H01L21/285—Deposition of conductive or insulating materials for electrodes conducting electric current from a gas or vapour, e.g. condensation
- H01L21/28506—Deposition of conductive or insulating materials for electrodes conducting electric current from a gas or vapour, e.g. condensation of conductive layers
- H01L21/28512—Deposition of conductive or insulating materials for electrodes conducting electric current from a gas or vapour, e.g. condensation of conductive layers on semiconductor bodies comprising elements of Group IV of the Periodic Table
- H01L21/28556—Deposition of conductive or insulating materials for electrodes conducting electric current from a gas or vapour, e.g. condensation of conductive layers on semiconductor bodies comprising elements of Group IV of the Periodic Table by chemical means, e.g. CVD, LPCVD, PECVD, laser CVD
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Description
本發明係關於用以藉由化學蒸鍍法(化學氣相蒸鍍法(CVD法)、及原子層蒸鍍法(ALD法))製造釕薄膜或釕化合物薄膜之由有機釕化合物構成的化學蒸鍍用原料。詳細而言係關於分解溫度低,並且具有適度的熱安定性之化學蒸鍍用原料。
作為DRAM、FERAM等之半導體裝置的薄膜電極材料係可使用釕或釕化合物。作為此等薄膜之製造法係可適用CVD法(化學氣相蒸鍍法)、ALD法(原子層蒸鍍法)之化學蒸鍍法。作為在如此之化學蒸鍍法中使用的原料化合物,已知以往較多為有機釕化合物。
一般而言,作為對化學蒸鍍用之有機釕化合物所要求的特性係為了有效率地形成薄膜而要求高蒸氣
壓。又,若考慮操作性,則較佳為於常溫時為液體狀態者。在如此之觀點的基礎下,可使用環狀或鏈狀二烯基之配位的有機釕化合物。環狀或鏈狀二烯基之配位的化合物係在空氣中之安定性相對較高,而操作容易者居多。
例如,作為具有環戊二烯基之化合物係有下述式所示之雙(乙基環戊二烯基)釕Ru(EtCp)2、或(2,4-二甲基戊二烯基)(乙基環戊二烯基)釕Ru(EtCp)(Me2PD)(非專利文獻1),作為配位有2個戊二烯基之化合物係有雙(2,4-二甲基戊二烯基)釕Ru(Me2PD)2、或雙(1-乙基戊二烯基)釕Ru(EtPD)2(非專利文獻1、專利文獻1),作為配位有環己二烯基之化合物係可列舉雙(2,6,6-三甲基環己二烯基)釕Ru(Me3CHD)2(專利文獻2)。
上述式中,EtCp為乙基環戊二烯基
Me2PD為2,4-二甲基戊二烯基
EtPD為1-乙基戊二烯基
Me3CHD為2,6,6-三甲基環己二烯基
上述化合物係蒸氣壓相對較高,在常溫下為
液體者居多。尤其,若著眼於分解溫度,則Ru(EtCp)(Me2PD)係約270℃,Ru(Me2PD)2係約210℃之低溫,此等化合物即使在低溫下也容易成膜。
[專利文獻1]日本特開2008-69453號公報
[專利文獻2]日本特表2010-513467號公報
[非專利文獻1] Materials Research Society Symposium Proceedings 1155-C09-11 (2009)
在此,在將釕薄膜或釕化合物薄膜成膜於半導體等之裝置上時,有時無法處於高溫條件,而要求有在極低溫下可成膜之有機釕化合物的提供。因此,較佳為即使在比Ru(EtCp)(Me2PD)的分解溫度,即270℃更低溫(例如,250℃左右)下也可成膜的化合物。另一方面,若僅考慮分解溫度,則雖Ru(Me2PD)2之分解溫度為210℃之低溫,但由於極端的分解溫度之低度因此熱安定性低,而操作為困難。例如,由於為了防止成膜時之熱分解,而降低試料加熱溫度(約80℃以下),因此導致成膜時之蒸氣壓變
低。
在如此之背景的基礎下,本發明係提供一種具有對於CVD化合物之要求特性,亦即,蒸氣壓高,在低溫(約250℃以下)下可成膜,且適度的熱安定性之化學蒸鍍用原料。
解決上述課題之本發明係關於一種化學蒸鍍用原料,其係用以藉由化學蒸鍍法製造釕薄膜或釕化合物薄膜之化學蒸鍍用原料,其係由下述式所示之於釕上配位有環己二烯基或其衍生物,及戊二烯基或其衍生物之有機釕化合物所成。
上述式中,取代基R1~R12分別為氫原子、鏈狀或環狀烴、胺、亞胺、醚、酮、酯之任一者。取代基R1~R12之碳數分別為6以下。
本發明之化學蒸鍍用原料係由具有環己二烯基與戊二烯基作為配位子之有機釕化合物所成。該化合物
係由於分解溫度低(250℃左右),而可低溫成膜,並且具有適度的熱安定性,因此操作性為良好。
於本發明之化學蒸鍍用原料中係如上所述般,於具有環己二烯基及戊二烯基之兩配位子的點上具有特徵。此點,本發明者們係著眼於釕之配位子,依據其種類,針對配位子與釕之鍵結的強度,或化合物之熱安定性,而有如以下般的傾向。
Ru-環戊二烯基>Ru-環己二烯基>Ru-戊二烯基(鏈狀二烯基)
接著,發現在成為於釕上具有環己二烯基及戊二烯基之兩配位子的化合物之情況,係如以下般地成為具有適度的熱特性之化合物,因而想到上述本發明。
Ru(EtCp)2《分解溫度350℃》>Ru(Me3CHD)2>Ru(EtCp)(Me2PD)《分解溫度270℃》>本發明之化合物>Ru(Me2PD)2《分解溫度210℃》
以下,關於本發明之化學蒸鍍用原料的各構成詳細地說明。
「環己二烯基或其衍生物」係具有取代基R1~R7。取代基R1~R7係氫原子、鏈狀或環狀之烴、胺、亞胺、醚、酮、酯之任一者。取代基R1~R7較佳為氫原子
或碳數1以上、6以下之直鏈或分支鏈之烴。作為烴較佳為甲基或乙基。取代基R1~R7之碳數為6以下,較佳為3以下,特佳為2以下。又,取代基R1~R7當中,較佳係2個以上、4個以下之取代基為氫原子,其餘取代基為甲基或乙基,取代基R6及R7較佳為甲基或乙基。在對氫原子而言烷基取代基之數目過多的情況,或在烷基取代基之碳鏈過長的情況,蒸氣壓會變低,作為化學蒸鍍用原料較不理想。
「戊二烯基或其衍生物」係具有取代基R8~R12。取代基R8~R12係氫原子、鏈狀或環狀之烴、胺、亞胺、醚、酮、酯之任一者。取代基R1~R7較佳為氫原子或碳數1以上、6以下之直鏈或分支鏈之烴。作為烴較佳為甲基或乙基。尤其,取代基R8~R12當中,較佳係R8、R10及R12為氫原子,其餘取代基R9及R11為甲基、乙基或氫原子。取代基R8~R12之碳數為6以下,較佳為3以下,特佳為2以下。在對氫原子而言烷基取代基之數目過多的情況,或在烷基取代基之碳鏈過長的情況,由於蒸氣壓會變低,因此作為化學蒸鍍用原料較不理想。
又,作為戊二烯基或其衍生物,較佳係具有2個甲基作為取代基之二甲基戊二烯基。尤其,較佳係R9及R11為甲基之2,4-二甲基戊二烯基。
作為有機釕化合物之具體例係可列舉如下述式般之化合物。該化合物係成為在分解溫度為250℃左右下容易低溫成膜者。
本發明之化學蒸鍍用原料係可用於以化學蒸鍍法所致之釕薄膜形成。在化學蒸鍍法中,藉由使作為原料之有機釕化合物在真空中進行加熱而氣化,來產生原料氣體。藉由將此原料氣體吹附於加熱後的基板表面,使錯合物進行熱分解而形成釕薄膜的方法,使用以上說明的原料作為有機釕化合物。
成膜時之基板加熱溫度係可設為150℃以上、500℃以下。由於使基板加熱溫度成為低溫側一事為本發明的目的之一,因此基板加熱溫度較佳係設為150℃以上、400℃以下,更佳為220℃以上、350℃以下。在未達150℃時,成膜反應難以進行而難以得到必要的膜厚。若溫度過高,則變得難以形成均勻的薄膜,在將釕膜進行成膜時,容易於膜中混入雜質。
本發明之化學蒸鍍用原料係具有蒸氣壓高,適度的熱安定性,並且分解溫度低(約250℃以下),在低溫下之成膜性優異。
[第1圖]係本實施形態之化合物的TG-DTA測定結果圖。
[第2圖]係本實施形態之釕薄膜的SEM觀察照片。
以下,針對本發明之最佳的實施形態進行說明。
於本實施形態中係製造下述式所示之3種有機釕化合物。又,分解溫度之評估,及所形成的薄膜之性
能亦進行評估。
作為化合物A係將(2,4-二甲基戊二烯基)(2,6,6-三甲基環己二烯基)釕(II)藉由下述步驟進行合成。
於裝有乙醇900ml的燒瓶中,依序分別添加乙腈2.38ml、2,4-二甲基1,3-戊二烯基35.3g(366.4mmol)、碳酸鋰13.5g(183.2mmol)、二-μ-氯二氯-雙[(1-3η):(6-8η)-2,7-二甲基辛二烯二基]釕(IV)28.2g(45.8mmol)而成為懸浮液。在將該懸浮液進行加熱並進行攪拌回流4小時之後,冷卻至室溫。冷卻後的液體係添加了2,6,6-三甲基-1,3-環己二烯基5.6g(45.8mmol)之後,進行加熱並進行攪拌回流6小時。反應結束後,冷卻至室溫,進行濃縮而得到泥狀之反應混合物。從所得到的泥狀之反應混合物以戊烷進行萃取,針對萃取液,將二氧化矽凝膠
(或氧化鋁)作為載體,將戊烷作為溶析液來進行管柱層析,進一步進行昇華純化,藉此得到作為目的物之(2,4-二甲基戊二烯基)(2,6,6-三甲基環己二烯基)釕(II)2.0g(6.3mmol)(產率7%,熔點104℃)。
作為化合物B係將(2,4-二甲基戊二烯基)(2,4,6,6-四甲基環己二烯基)釕(II)藉由下述步驟進行合成。
於裝有乙醇400ml的燒瓶中,依序分別添加乙腈1.04ml、2,4-二甲基1,3-戊二烯基15.4g(160mmol)、碳酸鋰6.0g(80mmol)、二-μ-氯二氯-雙[(1-3η):(6-8η)-2,7-二甲基辛二烯二基]釕(IV)12.4g(20mmol)而成為懸浮液。在將該懸浮液進行加熱並進行攪拌回流4小時之後,冷卻至室溫。冷卻後的液體係添加了1,3,5,5-四甲基-1,3-環己二烯基2.8g(20mmol)之後,進行加熱並進行攪拌回流6小時。反應結束後,冷卻至室溫,進行濃縮而得到泥狀之反應混合物。從所得到的泥狀之反應混合物以戊烷進行
萃取,針對萃取液,將二氧化矽凝膠(或氧化鋁)作為載體,將戊烷作為溶析液來進行管柱層析,進一步進行昇華純化,藉此得到作為目的物之(2,4-二甲基戊二烯基)(2,4,6,6-四甲基環己二烯基)釕(II)1.3g(3.92mmol)(產率10%,熔點67℃)。
作為化合物C係將(2,4-二甲基戊二烯基)(3-乙基-2,6,6-三甲基環己二烯基)釕(II)藉由下述步驟進行合成。
於裝有乙醇200ml的燒瓶中,依序分別添加乙腈0.52ml、2,4-二甲基1,3-戊二烯基7.7g(80mmol)、碳酸鋰3.0g(40mmol)、二-μ-氯二氯-雙[(1-3η):(6-8η)-2,7-二甲基辛二烯二基]釕(IV)6.2g(10mmol)而成為懸浮液。在將該懸浮液進行加熱並進行攪拌回流4小時之後,冷卻至室溫。冷卻後的液體係添加了2-乙基-1,5,5-三甲基-1,3-環己二烯基2.7g(20mmol)之後,進行加熱並進行攪拌回流6小時。反應結束後,冷卻至室溫,進行濃縮而得到泥狀之反應混合物。從所得到的泥狀之反應混合物以戊烷進行萃
取,針對萃取液,將二氧化矽凝膠(或氧化鋁)作為載體,將戊烷作為溶析液來進行管柱層析,進一步進行蒸餾,藉此得到作為目的物之(2,4-二甲基戊二烯基)(3-乙基-2,6,6-三甲基環己二烯基)釕(II)0.8g(3.92mmol)(產率12%,熔點-20℃以下)。
針對化合物C亦以下述方法進行合成。
於裝有鋅20.0g(3.06mol)的燒瓶中,依序分別添加2,4-二甲基1,3-戊二烯基114.4g(1.19mol)、2-乙基-1,5,5-三甲基-1,3-環己二烯基31.1g(0.21mol)而成為懸浮液。使氯化釕3水合物30.0g(0.12mol)於乙醇500ml中溶解後的溶液在室溫下一邊進行攪拌一邊緩緩地滴下於該懸浮液中。在30分鐘、室溫下進行攪拌之後,進行加熱並攪拌回流4小時。反應結束後,冷卻至室溫,從反應溶液將鋅藉由過濾而去除,進行濃縮而得到反應混合物。從所得到的反應混合物以己烷進行萃取,針對萃取液,將二氧
化矽凝膠作為載體,將己烷作為溶析液來進行管柱層析,進一步進行蒸餾,藉此得到作為目的物之(2,4-二甲基戊二烯基)(3-乙基-2,6,6-三甲基環己二烯基)釕(II)13.1g(0.038mol)(產率33%,熔點-20℃以下)。
另外,亦可利用與上述之化合物C之合成(2)相同的方法,將(2,4-二甲基戊二烯基)(2,6,6-三甲基環己二烯基)釕(II)及(2,4-二甲基戊二烯基)(2,4,6,6-四甲基環己二烯基)釕(II)進行合成。
針對上述合成之化合物A、B及C,進行以DSC所致之熱特性的評估。
熱量測定(DSC):利用TAInstruments公司製Q2000,將各化合物(樣品重量3.8mg)填充於不鏽鋼製耐壓計中,在氮環境下,在昇溫速度10℃/min、測定溫度範圍室溫~300℃,觀察熱量變化。將結果顯示於下述表中。將針對下述以往例之有機釕化合物(X1~X3)之分解溫度之非專利文獻2記載之值一併記載於表中。
[非專利文獻2] Electrochemical and Solid-State Letters Vol.12 No.10 pD80-83 (2009)
如上述結果般,化合物A~C之分解溫度皆為250℃以下,可低溫成膜,並且任一者在操作中皆不會越
進行分解而分解溫度越低,而具有適度的熱安定性。
示差熱-熱重量同時測定(TG-DTA):以BRUKER公司製TG-DTA2000SA,將化合物A、B及C(樣品重量5mg)填充於不鏽鋼製元件中,在氮環境下,在昇溫速度5℃/min、測定溫度範圍室溫~500℃,觀察熱量及重量變化。將結果顯示於第1圖。
依據第1圖,化合物A、B、C任一者於TG中在210℃下皆觀察到減量,而可推測為適合於低溫(250℃以下)之成膜。
成膜試驗:將化合物C作為原料,使用冷壁式之成膜裝置,藉由CVD法形成釕薄膜。於試驗No.1中,將形成薄膜之基板設為矽,試料加熱溫度為90℃,基板加熱溫度為210℃,以20sccm供給氫作為反應氣體,設為壓力150torr、成膜時間180分鐘之成膜條件。又,在將基板設為氧化矽的情況,或使基板加熱溫度變化的情況等,亦以下述表所示之條件進行試驗No.2~6之成膜。
針對以上述各基板加熱溫度所製作的釕膜,進行藉由SEM觀察所致之膜厚測定與比電阻之測定。將針對試驗No.3~5之SEM觀察照片顯示於第2圖。又,將比電阻顯示於下述表中。
SEM觀察的結果,以任一基板加熱溫度製作出的釕膜皆成為均勻且連續的膜厚者,且無觀察到龜裂、洞、島狀之凝聚等。
又,針對比電阻,以上述試驗例之條件所製作出的釕膜,皆顯示出比電阻60μΩcm以下之低的值。尤其,將成膜時之基板加熱溫度設為220℃以上、350℃以下之試驗No.3~5之釕膜,尤其比電阻為30μΩcm以下之低的值。
本發明之原料係蒸氣壓高,具有適度的熱安定性,並且分解溫度低(約250℃以下),在低溫下之成膜性優異,比電阻亦低。因此,亦適於作為DRAM、FERAM等之半導體裝置的薄膜電極材料之使用。
Claims (2)
- 一種化學蒸鍍用原料,其係利用化學蒸鍍法製造釕薄膜或釕化合物薄膜用之化學蒸鍍用原料,其係由下述式所示之於釕上配位有環己二烯基之衍生物及戊二烯基之衍生物之有機釕化合物所成,
- 一種化學蒸鍍法,其係使由有機釕化合物所成之原料氣化作成原料氣體,一面將前述原料氣體導入基板表面一方面加熱之釕薄膜或釕化合物薄膜之化學蒸鍍法,其中使用如請求項1之化學蒸鍍用原料作為前述原料。
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JP7148377B2 (ja) * | 2018-12-03 | 2022-10-05 | 田中貴金属工業株式会社 | ルテニウム錯体からなる化学蒸着用原料及び該化学蒸着用原料を用いた化学蒸着法 |
US20220372056A1 (en) * | 2019-06-21 | 2022-11-24 | Adeka Corporation | Ruthenium compound, thin-film forming raw material, and method of producing thin film |
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TW200844252A (en) * | 2006-12-22 | 2008-11-16 | Air Liquide | Method for the deposition of a ruthenium containing film |
TWI372150B (en) * | 2004-02-04 | 2012-09-11 | Praxair Technology Inc | High nucleation density organometallic compounds |
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JP4152028B2 (ja) * | 1999-01-25 | 2008-09-17 | 株式会社Adeka | ルテニウム系薄膜の製造方法 |
EP1887102B1 (en) | 2006-08-08 | 2020-04-08 | L'AIR LIQUIDE, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Precursors having open ligands for ruthenium containing films deposition |
KR20100060482A (ko) * | 2008-11-27 | 2010-06-07 | 주식회사 유피케미칼 | 루테늄 금속 또는 루테늄 산화물 박막 증착용 유기 금속 전구체 화합물 및 이를 이용한 박막 증착 방법 |
JP5579019B2 (ja) * | 2010-10-25 | 2014-08-27 | Jsr株式会社 | ルテニウム化合物の製造方法 |
TWI610932B (zh) * | 2012-12-07 | 2018-01-11 | 東曹股份有限公司 | 釕錯合物及其製造方法、陽離子性三腈錯合物及其製造方法、以及含釕薄膜的製造方法 |
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TWI372150B (en) * | 2004-02-04 | 2012-09-11 | Praxair Technology Inc | High nucleation density organometallic compounds |
TW200844252A (en) * | 2006-12-22 | 2008-11-16 | Air Liquide | Method for the deposition of a ruthenium containing film |
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JP5892668B1 (ja) | 2016-03-23 |
TW201625652A (zh) | 2016-07-16 |
US10131987B2 (en) | 2018-11-20 |
WO2016052288A1 (ja) | 2016-04-07 |
JP2016074929A (ja) | 2016-05-12 |
EP3202949A4 (en) | 2018-06-13 |
EP3202949A1 (en) | 2017-08-09 |
US20170218509A1 (en) | 2017-08-03 |
KR20170057402A (ko) | 2017-05-24 |
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