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R-- C23c I6/40 (2006.01) H R8 O R3| W USOO80O3814B2 (12) United States Patent (10) Patent No.: US 8,003,814 B2 Wada et al. (45) Date of Patent: Aug. 23, 2011 (54) METALALKOXIDE COMPOUND, MATERIAL JP 6-60406 8, 1994 FOR FORMING THIN FILM, AND METHOD E. 39: 33: FOR PRODUCING THIN FILM JP 2002-93804 3, 2002 JP 2005-340405 12/2005 (75) Inventors: Senji Wada, Tokyo (JP); Tetsuji Abe, JP 2006-182709 T 2006 Tokyo (JP); Atsushi Sakurai, Tokyo KR 100156980 B1 7, 1998 (JP); Takashi Higashino, Tokyo (JP); Ryusaku Fujimoto, Tokyo (JP); OTHER PUBLICATIONS Masako Shimizu, Tokyo (JP) S.C. Goeletal.—Methyl Butenoxy Derivatives of Various Elements, Z. anorg. allg. Chem. 447, pp. 253-256, Dec. 31, 1978. (73) Assignee: Adeka Corporation, Tokyo (JP) Chinese Official Action 200710152709.3–Apr. 26, 2011. (*) Notice: Subject to any disclaimer, the term of this * cited by examiner patent is extended or adjusted under 35 U.S.C. 154(b) by 1014 days. Primary Examiner — Porfirio Nazario Gonzalez (21) Appl. No.: 11/854,109 (74) Attorney, Agent, or Firm — Young & Thompson (22) Filed: Sep. 12, 2007 (57) ABSTRACT (65) Prior Publication Data A metal alkoxide compound represented by the following US 2008/O187662 A1 Aug. 7, 2008 general formula (1), (30) Foreign Application Priority Data (1) Sep. 15, 2006 (JP) ................................. 2006-251575 HC Sc (51) Int. Cl. C07F 7/00 (2006.01) R-- C23C I6/40 (2006.01) H R8 O R3| W"CH (52) U.S. Cl. ......................................... 556/54; 106/1.25 C-C-O-M-O-C-C (58) Field of Classification Search .................... 556/54; A | H 106/1.25 HC R7 O R4 See application file for complete search history. R-- (56) References Cited HC Sch, U.S. PATENT DOCUMENTS 2,684.972 A * 7/1954 Haslam ........................... 556/54 2007/O190249 A1 8, 2007 Hosokawa et al. wherein each of R' to R is independently ahydrogenatom or a methyl group; M is a titanium, a Zirconium or a hafnium FOREIGN PATENT DOCUMENTS atOm. JP 60-258132 12/1985 JP O1-172390 7, 1989 JP 5-2396.50 9, 1993 6 Claims, 4 Drawing Sheets U.S. Patent Aug. 23, 2011 Sheet 1 of 4 US 8,003,814 B2 FIG. P U.S. Patent Aug. 23, 2011 Sheet 2 of 4 US 8,003,814 B2 F.G.2 s 600 5.75 550 525 500 475 45 40 135 1.30 f U.S. Patent Aug. 23, 2011 Sheet 3 of 4 US 8,003,814 B2 FG.3 8 H Tetrakis (ethylmethylamino)zirconium Compound No.9 AO 10) 20 300 4. 500 SO Temperature (C) FIG.4 Tetrakis(ethylmethylaminohafnium Compound No.15 . I-1, - t-sis- Tetrakis(tert-butoxy) hafnium CO 200 3OO 400 500 600 Temperature ("C) U.S. Patent Aug. 23, 2011 Sheet 4 of 4 US 8,003,814 B2 PIG.5 se- Purge gas re- Reactive gas Material container s Exhat St Automatic pressure controller WacuumC pimp Cooling trap US 8,003,814 B2 1. 2 METALALKOXIDE COMPOUND, MATERIAL Tetrakis-dialkylamide compounds have problems in ther FOR FORMING THIN FILM, AND METHOD mal stability, and have a disadvantage in stable production of FOR PRODUCING THIN FILM thin films. Further, tetrakis-alkoxide compounds are not suf ficiently decomposed on thin film deposition, and have prob BACKGROUND OF THE INVENTION lems in productivity. 1. Field of the Invention SUMMARY OF THE INVENTION The present invention relates to a metal alkoxide com An object of the present invention is to allow, in a thin film pound having a novel specific structure, a material for form production process involving a vaporization step, the precur ing a thin film containing the compound, and a method for 10 Sor that Supplies titanium, Zirconium and hafnium to a thin producing a thin film using the material. film to have favorable decomposition properties by heat and/ 2. Description of the Related Art or oxidation, thermal stability, vapor pressure and others that A thin film that contains titanium, Zirconium or hafnium is meet the requirements needed as a material for forming thin used as an electronic member for electronic components such films, particularly as a material for CVD. as high-dielectric capacitors, ferroelectric capacitors, gate 15 As a result of intensive studies, the present inventors found insulating films and barrier films, or an optical member for that the above problems were resolved by a metal alkoxide optical communication devices such as optical wave guides, compound having a specific structure, and completed the optical Switches, and optical amplifiers. present invention. As a method for producing the above thin film, there may Namely, the present invention has achieved the above be mentioned flame deposition, sputtering, ion plating, MOD objective by providing a metal alkoxide compound repre Such as coating thermal decomposition and sol-gel processes, sented by the following general formula (1). chemical vapor deposition, or the like. Among these, chemi cal vapor deposition (hereinafter, may be simply referred to as “CVD) including Atomic Layer Deposition (ALD) is an (1) appropriate production process, because of its many advan 25 H2CsSo tages including excellent properties in composition control and step coverage, Suitability for mass production, capability of providing hybrid integration, and the like. R8 O R3 CH In the CVD process, a metal compound having organic H A ligands is used as a precursor Supplying metal atoms Source 30 C-C-O-M-O-C-C for a thin film. A compound (precursor) suitable for materials A | H used in CVD is required to have such properties as being HC R7 O R transportable in a liquid state upon vaporization and at trans portation, having a high vapor pressure and being easy to R-- evaporate, and being stable against heat. In addition, upon 35 HC thin film deposition, the decomposition is easily progressed Sch, by thermal and/or chemical reaction. As the precursors of titanium, Zirconium and hafnium, tetrakis-dialkylamide com wherein each of R' to R is independently a hydrogenatom pounds and tetrakis-alkoxide compounds have been exam or a methyl group; M is a titanium, a Zirconium or a hafnium ined. 40 atOm. Patent Documents 1 to 4 disclose tetrakis-amide com Further, the present invention has achieved the above pounds. Patent Documents 5 to 7 disclose tetrakis-alkoxide objective by providing a material for forming a thin film that compounds. Patent Document 8 discloses tetrakis-amide contains the above metal alkoxide compound. compounds, tetrakis-alkoxide compounds and the like. Fur Still further, the present invention has achieved the above ther, in claim 1 of Patent Document 9, a metal alkoxide 45 objective by providing a method for producing a thin film, compound represented by M(OR") (R' is an alkyl group or wherein the vapor that is obtained by vaporizing the above alkenyl group that has 2 to 21 carbon atoms and may be materials for forming a thin film and contains the metal alkox branched; and M is Zirconium, hafnium or titanium) is dis ide compound is introduced over a Substrate; and the vapor is closed. However, regarding the alkenyl group, no specific decomposed and/or chemically reacted so as to deposit a thin structure is disclosed. 50 film on the substrate. Patent Document 1: Japanese Patent Laid-Open Publica Still further, the present invention has achieved the above tion No. 2002-93803 objective by providing a thin film that is deposited on a Patent Document 2: Japanese Patent Laid-Open Publica Substrate by using the above method for producing a thin film. tion No. 2002-93804. The metal alkoxide compound of the present invention Patent Document 3: Korean Patent No. 156980 55 allows, in a thin film production process involving a vapor Patent Document 4: Japanese Patent Laid-Open Publica ization step, the precursor that Supplies titanium, Zirconium tion No. 2006-182709 and hafnium to a thin film to have favorable decomposition Patent Document 5: Japanese Patent Laid-Open Publica properties by heat and/or oxidation, thermal stability, vapor tion No. H5-239.650 pressure and others that meet the requirements needed as a Patent Document 6: Japanese Patent Application Publica 60 material for forming thin films, particularly as a material for tion No. H6-60406 CVD. Patent Document 7: Japanese Patent Laid-Open Publica tion No. 2002-69641 BRIEF DESCRIPTION OF THE DRAWINGS Patent Document 8: Japanese Patent Laid-Open Publica tion No. 2005-340405 65 FIG. 1 shows the 'H-NMR chart of the metal compound Patent Document 9: Japanese Patent Laid-Open Publica (compound No. 9) of the present invention obtained in tion No. S60-258132 Example 1. US 8,003,814 B2 3 4 FIG. 2 shows the 'H-NMR chart of the metal compound -continued (compound No. 15) of the present invention obtained in Compound No. 3 Example 2. HC Sc FIG. 3 shows the measurement results of differential ther mal analysis (DTA) for the metal compound (compound No. 5 HC-C-CH 9) of the present invention, and the comparative compounds CH3 O CH3 CH of tetrakis(ethylmethylamino)Zirconium and tetrakis(tert-bu H / " toxy)Zirconium. g--O-Ti-O-- FIG. 4 shows the measurement results of differential ther- 10 HC CH O CH mal analysis (DTA) for the metal compound (compound No. 15) of the present invention, and the comparative compounds HC-C-CH of tetrakis(ethylmethylamino)hafnium and tetrakis(tert-bu toxy)hafnium. Sch, Compound No. 4 FIG. 5 is a diagrammatic illustration of an exemplary CVD 15 apparatus used in Examples that is used in the method for producing a thin film of the present invention. HC-C-CH O CH DESCRIPTION OF THE PREFERRED H M EMBODIMENT C-C-O-Ti-O-C-C / H2 H.
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