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 Table
  • C07F7/22—Tin compounds
  • C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
• • 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
  • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
  • C07F15/04—Nickel compounds
• • 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
  • C07F17/00—Metallocenes
• • 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
  • C07F7/22—Tin compounds
  • C07F7/2224—Compounds having one or more tin-oxygen 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 Table
  • C07F7/22—Tin compounds
  • C07F7/2284—Compounds with one or more Sn-N linkages
• • C—CHEMISTRY; METALLURGY
  • 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
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/26—Processing photosensitive materials; Apparatus therefor
  • G03F7/30—Imagewise removal using liquid means
  • G03F7/32—Liquid compositions therefor, e.g. developers
  • G03F7/325—Non-aqueous compositions
• • C—CHEMISTRY; METALLURGY
  • 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
  • C23C16/22—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 inorganic material, other than metallic material
  • C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
  • C23C16/40—Oxides
  • C23C16/407—Oxides of zinc, germanium, cadmium, indium, tin, thallium or bismuth
• • C—CHEMISTRY; METALLURGY
  • 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
  • C23C16/455—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 introducing gases into reaction chamber or for modifying gas flows in reaction chamber
  • C23C16/45523—Pulsed gas flow or change of composition over time
  • C23C16/45525—Atomic layer deposition [ALD]
  • C23C16/45553—Atomic layer deposition [ALD] characterized by the use of precursors specially adapted for ALD

Definitions

• the present disclosure relates to organometallic compounds useful for the deposition of high purity tin oxide and highly purified forms of the organometallic compounds. More specifically, the present disclosure describes specific compounds useful in deposition of high purity tin oxide as well as compositions that result in improved reactivity and better stability.
• EUV Extreme ultraviolet
• lithography enables a superb resolution of patterns that have been transferred onto a wafer substrate to form microchips.
• traditional chemical amplified resists are highly transparent at an EUV wavelength of 13.5nm (92 eV).
• One strategy to increase the sensitivity of photosensitive materials is an incorporation of atoms with enhanced absorptivity in the EUV regime, such as Sn, into the resist composition.
• Sn enhanced absorptivity
• Ligands containing unsaturated hydrocarbons may provide increased bond energy of the Sn-C bond. By strengthening the Sn-C bond, some ligands bonded to Sn may be retained in the deposited film for further EUV treatment, which may be advantageous in particular uses.
• amino, alkoxy, or halide ligands enable reactivity with OH groups of wafers/substrate layers for effective ALD deposition.
• organometallics of tin having a combination of ligands containing unsaturated hydrocarbons and ligands containing amino, alkoxy, or halide ligands have improved properties for deposition, especially atomic layer deposition, and for use as a photosensitive material in patterning applications.
• organometallic compounds of Formula I below: (R) x Sn(A) 4-x Formula I wherein: US.357047440.01 2 R is substituted Cp, unsubstituted Cp, or a non-cyclic unsaturated hydrocarbon having 2 to 10 carbon atoms, or 2 to 8 carbon atoms, or 2 to 4 carbon atoms; A is NR 1 R 2 , OR 3 , pyrrolidinyl, pyrrolyl, or halide; R 1 and R 2 are each an alkyl group having from 1 to 10 carbon atoms; R 1 and R 2 can be the same or different; R 3 is an alkyl group having 2 to 8 carbon atoms; x is an integer from 1 to 3; and when A is NR 1 R 2 , pyrrolidinyl, pyrrolyl, or halide, R is substituted Cp or a non-cyclic unsaturated hydrocarbon having 2 to 10 carbon atoms, or 2 to
• R is an allyl or vinyl group.
• the allyl or vinyl group can be straight chain.
• R is Cp, which is a cyclopentadienyl group having R 12 , R 13 , R 14 , R 15 , and R 16 constituents. Depending on A, Cp can be substituted or unsubstituted.
• R 12 , R 13 , R 14 , R 15 , and R 16 each independently selected from H and an alkyl group having from 1 to 10 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, or decyl.
• R 12 , R 13 , R 14 , R 15 , and R 16 can be the same or different.
• A is NR 1 R 2 , pyrrolidinyl, US.357047440.01 3 pyrrolyl, or halide
• at least one of R 12 , R 13 , R 14 , R 15 , and R 16 is an alkyl group having from 1 to 10 carbon atoms.
• A is NR 1 R 2 .
• R 1 and R 2 are independently selected from an alkyl group having from 1 to 4 carbon atoms.
• R 1 and R 2 are methyl or ethyl.
• R 1 and R 2 are different.
• A can be OR 3 .
• R 3 is an alkyl group having from 1 to 4 carbon atoms.
• R 3 is methyl, ethyl, or tert-butyl.
• A is one of pyrrolyl, pyrrolidinyl, or halide.
• FIG.10 shows a 119 Sn NMR spectrum of Cp iPr Sn(NMe 2 ) 3 (186 MHz, C 6 D 6 ).
• FIG.11A shows a cross section of a deposited intermediate product.
• FIG.11B shows a cross section of a developed intermediate product. US.357047440.01 5
• FIG.11C shows a cross section of an etched intermediate product.
• FIG.11D shows a cross section of a final product.
• FIG.12 shows a schematic of a multistage vacuum distillation apparatus. DETAILED DESCRIPTION
• organometallic compounds of Formula I below: (R) x Sn(A) 4-x Formula I wherein: R is substituted Cp, unsubstituted Cp, or a non-cyclic unsaturated hydrocarbon having 2 to 10 carbon atoms, or 2 to 8 carbon atoms, or 2 to 4 carbon atoms; A is NR 1 R 2 , OR 3 , pyrrolidinyl, pyrrolyl, or halide; R 1 and R 2 are each an alkyl group having from 1 to 10 carbon atoms; R 1 and R 2 can be the same or different; R 3 is an alkyl group having 2 to 8 carbon atoms; x is an integer from 1 to 3; and when A is NR 1 R 2 , pyrrolidinyl, pyrrolyl, or halide, R is substituted Cp or a non- cyclic unsaturated hydrocarbon having 2 to 10 carbon atoms, or 2 to 8 carbon atoms, or 2 to 4
• organometallic compounds and methods of purifying the organometallic compounds.
• bulkier ligands such as substituted allyl, substituted vinyl, substituted or unsubstituted Cp, which is cyclopentadienyl, heavier amines, or heavier alkoxies in the compound of Formula I may be able to prevent side product creation and improve stability by reducing ligand exchange.
• R 4 , R 5 , R 6 , R 7 , and R 8 can be the same or different.
• R 4 and R 5 is not H, such as 1,1-dimethylallyl, wherein R 4 and R 5 are both methyl.
• R 6 is not H, such as 2-methylallyl.
• at least one of R 7 and R 8 is not H, such as 3,3-dimethylallyl.
• R 9 , R 10 , and R 11 can be the same or different.
• R 9 is not H, such as 1-ethylvinyl.
• at least one of R 10 and R 11 is not H, such as 2,2- dimethylvinyl.
• Any of the above-mentioned compounds of Formula I include those in which x is 1.
• Compounds of Formula I are represented by the following formula: (R)Sn(A) 3 , wherein R is a non-cyclic unsaturated hydrocarbon having 2 to 10 carbon atoms. US.357047440.01 8 Compounds of Formula I also include those in which x is 3.
• compounds of Formula I are represented by the following formula: (R) 3 Sn(A), wherein R is a non-cyclic unsaturated hydrocarbon having 2 to 10 carbon atoms.
• R is a non-cyclic unsaturated hydrocarbon having 2 to 10 carbon atoms.
• Any of the above-mentioned compounds of Formula I represented by the formula: (R) x Sn(A) 4-x include those in which R is a non-cyclic unsaturated hydrocarbon having 2 to 8 carbon atoms.
• Compounds of Formula I include those in which R is a non-cyclic unsaturated hydrocarbon having 2 to 4 carbon atoms.
• Any of the above-mentioned compounds of Formula I include those in which A is NR 1 R 2 .
• R 1 and R 2 are independently selected from H, alkyl groups having from 1 to 10 carbon atoms, aryl groups, or acyl groups.
• R 1 and R 2 can be the same or different.
• R 1 and R 2 are each alkyl groups having 1 to 10 carbons atoms.
• R 1 and R 2 are each alkyl groups having from 2 to 4 carbon atoms. More particularly, R 1 and R 2 can each be selected from the group consisting of methyl, ethyl, propyl, iso-propyl, tert-butyl, iso-butyl, and n-butyl.
• R can be either a straight-chain unsaturated hydrocarbon or a branched unsaturated hydrocarbon.
• Any of the above-mentioned compounds of Formula I also include those in which A is OR 3 .
• compounds of Formula I are represented by the formula: (R) x Sn(OR 3 ) 4-x , wherein R 3 is an alkyl group having 2 to 8 carbon atoms. In other embodiments, R 3 is selected from the group consisting of an alkyl group having from 1 to 4 carbon atoms.
• R 3 can be selected from the group consisting of methyl, ethyl, propyl, iso- propyl, tert-butyl, iso-butyl, and n-butyl.
• A is an alkoxy group, such as OR 3
• R can be Cp.
• compounds of Formula I are represented by the formula: (Cp) x Sn(OR 3 ) 4-x , wherein Cp is a cyclopentadienyl group having R 12 , R 13 , R 14 , R 15 , and R 16 constituents.
• Cp can be unsubstituted, wherein R 12 , R 13 , R 14 , R 15 , and R 16 are H, or substituted, wherein at least one of R 12 , R 13 , R 14 , R 15 , and R 16 is independently selected from an alkyl group having from 1 to 10 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, or decyl.
• R 12 , R 13 , R 14 , R 15 , and R 16 can be the same or different.
• R can be substituted Cp, wherein at least one of R 12 , R 13 , R 14 , R 15 , and R 16 is independently selected from an alkyl group having from 1 to 10 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, or decyl.
• R 12 , R 13 , R 14 , R 15 , and R 16 can be the same or different.
• Compounds of Formula I include those in which A is pyrrolidinyl or pyrrolyl. Such embodiments are respectively represented by the general formula: (R) x Sn(Pyrrolidinyl) 4-x or (R) x Sn(Pyrrolyl) 4-x . It is contemplated that A could also be a halide, such as chloro, bromo, or iodo.
• R is Cp
• compounds of Formula I, (Cp) x Sn(A) 4-x may be synthesized as follows. In a glovebox, load a 1L round bottom flask with SnCl 4 and anhydrous hexanes. Add 1 equiv.
• Example 8 Synthesis of Cp iPr Sn(NMe 2 ) 3 [0074] In the glovebox, a small Schlenk flask was loaded with 1.2mL of Sn(NMe 2 ) 4 (4.7mmol) and ca.13mL of anhydrous THF. Add 0.679g of NaCp iPr (5.2mmol). Transfer this Schlenk flask onto the double manifold and proceed with reflux at 76°C for 4 hours. NMR analysis of the reaction mixture confirms formation of Cp iPr Sn(NMe 2 ) 3 .
• Compounds of Formula I could have improved thermal stability and surface reactivity compared to those known in the art, which may result in improved ALD films. Poor thermal stability can hinder reactivity of the precursor with the substrate surface during ALD deposition, that is, the precursor should not decompose prior to ALD deposition.
• ALD in CVD processes, high energy and temperature are used to react the precursors at process temperature. Then, the already-reacted precursors react on the substrate. Because the CVD process uses substantially larger energy and breaks apart the precursors prior to the reaction, the reactivity of the precursors is not as important in CVD processes as in ALD processes.
• FIG. 11A–11D show an exemplary process of negative resist deposition using a compound of Formula I.
• a multi-layer substrate 10 is provided.
• layer 10A is the only layer of the substrate that is to be patterned.
• a layer of photosensitive material 30 including the compound of Formula I is subsequently deposited onto the layer 10A.
• mask(s) 40 is selectively applied over portions of the layer of photosensitive material 30 such that unexposed portions 30A of the layer of photosensitive material 30 are covered by the mask 40 and exposed portions 30B of the layer of photosensitive material 30 are not covered by the mask 40.
• a mask glass layer 50 is applied over the mask(s) 40 and layer of photosensitive material 30.
• a deposited intermediate part 1a as shown in Figure 11A.
• US.357047440.01 18 The deposited intermediate part 1a is then illuminated with extreme ultraviolet (EUV) light through the mask(s) 40 resulting in a photolytic cleavage of Sn—C bonds that promotes cross-linking. After illumination, the deposited intermediate part 1a is baked to densify the SnO 2 layers. Then, the glass mask 50 is removed.
• a development step is illustrated in Figure 11B. During the development step, the unexposed portion 30A of the layer of photosensitive material 30 that was not exposed to EUV light during illumination is removed such that only the exposed portion 30B of the layer of photosensitive material 30 remains.
• the unexposed portion 30B is positioned over the layer 10A of the multi-layer substrate 10, as shown in Figure 11B. Thus, forming a developed intermediate product 1b as shown in Figure 11B.
• the layer 10A of the multi-layer substrate 10 is etched to produce a desired pattern. The etching results in layer 10B, which is covered by the exposed portion 30B of the layer of photosensitive material 30. Thus, forming an etched intermediate product 1c as shown in Figure 11C.
• the exposed portion 30B of the layer of photosensitive material 30 is removed, leaving behind the desired pattern.
• Figure 11D illustrates that resulting pattern. Thus, forming the product 1 as shown in Figure 11D.
• Compounds of Formula I are particularly advantageous for negative resist deposition methods because tuning the bond energy of Sn—C by using allyl or vinyl ligands improves performance of the Sn photosensitive materials. It is contemplated that photolytic cleavage of Sn—C bonds during exposure to EUV light will promote cross-linking, thus making these materials superior over those known in the art. US.357047440.01 19 Multistage Distillation [0083] From theoretical modeling of the activation energy required to strip off ligands from molecules via hydrolysis reaction, a wide range in activation energies between molecules is observed. Hence differences in reactivity are observed.
• multiple-effect or multistage distillation is a distillation process often used for sea water desalination. It consists of multiple stages or "effects".
• the first stage is at the top. Top areas of each stage are vapor, bottom areas of each stage are liquid feed material. The material running through the pipe along the left side of the figure and in the bottom of the VC is condensate. It is not shown how feed material enters other stages than the first, however those should be readily understood.
• VC is the last-stage cooler.
• the feed material is heated by steam in tubes. Some of the feed material US.357047440.01 20 evaporates, and this steam flows into the tubes of the next stage, heating and evaporating more of the distillate. Each stage essentially reuses the energy from the previous stage.
• the apparatus can be seen as a sequence of closed spaces separated by tube walls, with a heat source at one end and a heat sink at the other. Each space is at pressure below atmospheric conditions via vacuum. Each space consists of two communicating subspaces, the exterior of the tubes of stage n and the interior of the tubes in stage n+1. Each space has a lower temperature and pressure than the previous space, and the tube walls have intermediate temperatures between the temperatures of the fluids on each side.

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