# US 12,180,234 B2 · Metal organic compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,180,234 B2 - Document ID: US12180234B2 - Status: Granted - Kind: B2 - Application number: 17/263,195 - Filed: 2019-07-26 - Published: 2021-07-01 - Granted: 2024-12-31 - Earliest claimed: 2018-07-27 - Assignees: Umicore AG & Co. KG - Applicants: Umicore AG & Co. KG - Inventors: Nicholas Rau; Joerg Sundermeyer; Andreas Rivas Nass; Ralf Karch; Annika Frey; Angelino Doppiu; Eileen Woerner - Web page: https://patentgrep.com/patent/US12180234B2 ## CPC - C07F 15/0046: {Ruthenium compounds} - C23C 16/18: from metallo-organic compounds - C23C 16/45553: {characterized by the use of precursors specially adapted for ALD} - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - 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 (making metal-coated products by extrusion B21C23/22; covering with metal by connecting pre-existing layers to articles, see the relevant places, e.g. B21D39/00, B23K; metallising of glass C03C; metallising mortars, concrete, artificial stone, ceramics or natural stone C04B41/00; enamelling of, or applying a vitreous layer to, metals C23D; treating metal surfaces or coating of metals by electrolysis or electrophoresis C25D; single-crystal film growth C30B; by metallising textiles D06M11/83; decorating textiles by locally metallising D06Q1/04) ## Abstract The invention relates to the synthesis and provision of a new class of volatile metal organic compounds based on bis(alkylimine)glyoxal and bis(dialkylhydrazone)glyoxal ligands in combination with cyclopentadienide and alkyl ligands for use in ALD and CVD processes. ## Claims ### Claim 1 Compound having formula or formula [(CpR21R22R23R24R25)Ru(R4R5 (DAD) R6R7) R3], wherein R3 is selected from H, C1-C3 linear alkyl, or C3-C5 branched alkyl, wherein (R4R5 (DAD) R6R7) is selected from a chelating 1,4-diazadiene or a bis-hydrazone derivative of the general formula (R4)—N—CR5—CR6—N—(R7); wherein R4 and R7 are independently selected from the group consisting of C1-C3 linear alkyl, C3-C5 branched alkyl, and C3-C6 cyclic alkyl; or R4 is (R8,R9)N— and R7 is (R12,R13)N—, and R8, R9, R12 and R13 are independently selected from the group consisting of H, C1-C3 linear alkyl, C3-C5 branched alkyl, or two neighboring groups, selected from R8 and R9 or R12 and R13, which form a C3-C6 saturated or unsaturated cyclic alkyl, which optionally contain a heteroatom selected from O or S; R5 and R6 are independently selected from the group consisting of H, C1-C6 linear alkyl, C3-C6 branched alkyl, and C3-C6 cyclic alkyl; wherein R21, R22, R23, R24 and R25 are, independently from each other, selected from the group consisting of C1-C3 linear alkyl, C3-C6 branched alkyl, C3-C6 cyclic alkyl and NR312, wherein R31 is selected from the group consisting of H, methyl, ethyl, and isopropyl or two of R21,R22,R23,R24 and R25 are so linked to each other to form a phenylene. ### Claim 2 (depends on 1) A compound according to claim 1, wherein (R4R5 (DAD) R6R7) is a chelating 1,4-diazadiene derivative of the general formula (R4)—N═CR5—CR6—N—(R7) wherein R4 and R7, are independently selected from the group consisting of C1-C3 linear alkyl, and C3-C5 branched alkyl; R5 and R6 are independently selected from the group consisting of H, C1-C3 linear alkyl, and C3-C5 branched alkyl; R21, R22, R23, R24 and R25 are, independently from each other, selected from the group consisting of C1-C3 linear alkyl, and C3-C6 branched alkyl. ### Claim 3 (depends on 1) A compound of claim 1, wherein R21,R22,R23,R24 and R25 are, independently from each other, selected from the group consisting of methyl, ethyl, isopropyl and tert.-butyl. ### Claim 4 (depends on 1) A compound of claim 1, wherein R21 to R25 are not identical; or at least one of R21 to R25 is different. ### Claim 5 (depends on 1) A compound of claim 1, wherein R21 to R25 are identical. ### Claim 6 (depends on 1) A compound of claim 1, wherein R4 and R7 are, independently from each other, selected from the group consisting of methyl, ethyl, isopropyl and tert.-butyl. ### Claim 7 (depends on 1) A compound of claim 1, wherein R5 and R6 are, independently from each other, selected from the group consisting of H, methyl, ethyl, isopropyl and tert.-butyl. ### Claim 8 (depends on 1) A compound of claim 1, wherein R4 to R7 are not identical, or at least one of R4 to R7 is different. ### Claim 9 (depends on 1) A compound of claim 1, wherein R4 and R7 are identical. ### Claim 10 (depends on 1) A compound of claim 1, wherein R8, R9, R12 and R13 are independently from each other, selected from C1-C3 linear alkyl, C3-C5 branched alkyl or two neighboring groups, R8 and R9 or R12 and R13 together forming a C4 to C6 saturated cyclic alkyl, which optionally contain a heteroatom selected from O or S. ### Claim 11 (depends on 1) A compound of claim 1, wherein R8, R9, R12 and R13 are independently from each other, selected from methyl, ethyl, isopropyl, tert.-butyl, pyrrolidinyl, piperidinyl or morpholinyl. ### Claim 12 (depends on 1) A compound of claim 1, wherein (R4R5 (DAD) R6R7) being selected from the group consisting of (R8,R9)N—N═CR5—CR6—N—N(R12,R13), R4—N═CR5—CR6—N—N(R12,R13) with R4 being different from (R8,R9)N, (R8,R9)N—N═CR5—CR6—N—R7 with R7 being different from (R12,R13)N, R4—N—CR5—CR6—N—R7 with R4 being different from (R8,R9)N and R7 being different from (R12,R13)N. ### Claim 13 (depends on 1) A compound of claim 1, wherein R3 is selected from H, methyl or ethyl. ### Claim 14 (depends on 1) A compound of claim 1, wherein the (CpR21R22R23R24R25) is a pentamethyl substituted cyclopentadienide ligand Cp*.