Patents by Inventor Robert E. Jilek

Robert E. Jilek has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Publication number: 20260153801
    Abstract: Organometallic patterning compositions are modified with iodine to improve radiation sensitivity and reduce radiation dose without significant loss of pattern quality. Iodine can be introduced as ligands to the metal ion and/or through introduction of iodide containing additives. Iodine is found to survive, at least in part, pre-irradiation processing. Thus, iodide ions are maintained in some form in the films being irradiated.
    Type: Application
    Filed: December 1, 2025
    Publication date: June 4, 2026
    Inventors: Robert E. Jilek, Lauren B. McQuade, Alexander C. Marwitz, Munendra Yadav, Brian J. Cardineau
  • Patent number: 12630737
    Abstract: Organotin compositions having the formula RSnL3 and corresponding synthetic methods are described. R includes aromatic, cyclic and/or halogenated ether moieties, or polyethers, and L includes hydrolysable groups. The organotin compositions may be formed as radiation-patternable coatings on substrates. The coatings may have an average thickness from about 1 nm to about 75 nm and have the formula RSnOn(OH)3-2n, forming an oxo-hydroxo network, where R is a hydrocarbyl ether group with 1 to 30 carbon atoms and 0<n<3/2, wherein regions of the coating are soluble in 2-heptanone in a puddle development step following a bake at 150° C. for 120 seconds. The coatings may be radiation-patternable using UV, EUV or ion beam radiation, and corresponding methods are described.
    Type: Grant
    Filed: May 17, 2023
    Date of Patent: May 19, 2026
    Assignee: Inpria Corporation
    Inventors: Robert E. Jilek, Brian J. Cardineau, Lucy Su Xiao Huffman, Stephen T. Meyers
  • Patent number: 12595272
    Abstract: Synthesis reactions are described to efficiently and specifically form compounds of the structure RSnL3, where R is an organic ligand to the tin, and L is hydrolysable ligand or a hydrolysis product thereof. The synthesis is effective for a broad range of R ligands. The synthesis is based on the use of alkali metal ions and optionally alkaline earth (pseudo-alkaline earth) metal ions. Compounds are formed of the structures represented by the formulas RSn(C?CSiR?3)3, R?R?ACSnL3, where A is a halogen atom (F, Cl, Br or I) or an aromatic ring with at least one halogen substituent, R?R? (R?O) CSnL3 or R?R? (N?C) CSnZ3.
    Type: Grant
    Filed: August 24, 2021
    Date of Patent: April 7, 2026
    Assignee: Inpria Corporation
    Inventors: Joseph B. Edson, Brian J. Cardineau, William Earley, Kierra Huihui-Gist, Thomas J. Lamkin, Robert E. Jilek
  • Publication number: 20260049094
    Abstract: Synthesis reactions are described to efficiently and specifically form compounds of the structure RSnL3, where R is an organic ligand to the tin, and L is hydrolysable ligand or a hydrolysis product thereof. The synthesis is effective for a broad range of R ligands. The synthesis is based on the use of alkali metal ions and optionally alkaline earth (pseudo-alkaline earth) metal ions. Compounds are formed of the structures represented by the formulas RSn(C?CSiR?3)3, R?R?ACSnL3, where A is a halogen atom (F, Cl, Br or I) or an aromatic ring with at least one halogen substituent, R?R?(R??O)CSnL3 or R?R?(N?C)CSnZ3.
    Type: Application
    Filed: October 27, 2025
    Publication date: February 19, 2026
    Inventors: Joseph B. Edson, Brian J. Cardineau, William Earley, Kierra Huihui-Gist, Thomas J. Lamkin, Robert E. Jilek
  • Publication number: 20260042786
    Abstract: Synthesis reactions are described to efficiently and specifically form compounds of the structure RSnL3, where R is an organic ligand to the tin, and L is hydrolysable ligand or a hydrolysis product thereof. The synthesis is effective for a broad range of R ligands. The synthesis is based on the use of alkali metal ions and optionally alkaline earth (pseudo-alkaline earth) metal ions. Compounds are formed of the structures represented by the formulas RSn(C?CSiR?3)3, R?R?ACSnL3, where A is a halogen atom (F, Cl, Br or I) or an aromatic ring with at least one halogen substituent, R?R?(R??O)CSnL3 or R?R?(N?C)CSnZ3.
    Type: Application
    Filed: October 22, 2025
    Publication date: February 12, 2026
    Inventors: Joseph B. Edson, Brian J. Cardineau, William Earley, Kierra Huihui-Gist, Thomas J. Lamkin, Robert E. Jilek
  • Publication number: 20250270240
    Abstract: Organometallic precursor compositions containing a polyene ligand, such as a diene ligand, are described. Corresponding films are also described and show promising solubility behavior. A synthesis technique is described for forming a polyene-containing organotin trialkoxide compound. The incorporation of polymerization inhibitors and/or blends of organotin compounds with different ligands are described as a way to design radiation sensitive films to have target solubility properties.
    Type: Application
    Filed: February 21, 2025
    Publication date: August 28, 2025
    Inventors: Robert E. Jilek, Christopher J. Reed, Matthew Voss
  • Publication number: 20250258432
    Abstract: As described herein, photosensitive composition comprises RSnL3, where R is a hydrocarbyl ligand with 1-20 carbon atoms and one or more silicon and/or germanium heteroatoms and L is an acetylide ligand (—C?CA, where A is a silyl group with 0 to 6 carbon atoms or an organo group with 1 to 10 carbon atoms). Methods are described wherein photosensitive compositions are synthesized by reacting RX, where X is a halide, and MSnL3, where M is an alkali metal, alkali earth metal or a pseudo-alkali earth metal, L is an acetylide or a dialkylamide. The radiation sensitive compositions are effective for radiation based patterning, such as with EUV light.
    Type: Application
    Filed: April 9, 2025
    Publication date: August 14, 2025
    Inventors: Robert E. Jilek, Kai Jiang, Amrit K. Narasimhan
  • Publication number: 20250251662
    Abstract: An organometallic precursor solution comprising an organic solvent, a radiation sensitive organometallic precursor composition with hydrolysable metal ligands, and a radical scavenger additive is described. The radical scavenger additive or a blend of radical scavenger additives can provide for improvements to the stability of an organometallic precursor solution, such as improvements to storage stability, shelf-life, and/or batch-to-batch reproducibility through mitigation of the effects of reactive compounds in the environment, such as oxygen. A structure having a substrate, a radiation patternable organometallic coating composition, and a radical scavenging additive is also described. The radical scavenger additive or a blend thereof can result in patterning improvements, such as by improving coating quality and reducing patterning variability. Methods of using a radical scavenging additive in the formation of a structure comprising a radiation patternable organometallic film are described.
    Type: Application
    Filed: January 31, 2025
    Publication date: August 7, 2025
    Inventors: Fabian Felix Eberle, Amy M. Jystad, Brian J. Cardineau, Kai Jiang, Ken Maruyama, Seitarou Hattori, Kazuki Kasahara, Colin T. Carver, Robert E. Jilek, Peter De Schepper
  • Patent number: 12298666
    Abstract: As described herein, photosensitive composition comprises RSnL3, where R is a hydrocarbyl ligand with 1-20 carbon atoms and one or more silicon and/or germanium heteroatoms and L is an acetylide ligand (—C?CA, where A is a silyl group with 0 to 6 carbon atoms or an organo group with 1 to 10 carbon atoms). Methods are described wherein photosensitive compositions are synthesized by reacting RX, where X is a halide, and MSnL3, where M is an alkali metal, alkali earth metal or a pseudo-alkali earth metal, L is an acetylide or a dialkylamide. The radiation sensitive compositions are effective for radiation based patterning, such as with EUV light.
    Type: Grant
    Filed: May 3, 2024
    Date of Patent: May 13, 2025
    Assignee: Inpria Corporation
    Inventors: Robert E. Jilek, Kai Jiang, Amrit K. Narasimhan
  • Publication number: 20250085627
    Abstract: Organotin patterning compositions can incorporate Sn—F bonds to improve pattering performance. A precursor solution for a radiation patterning composition can comprise a blend of an organic solvent, an organotin composition represented by the formula RSnL3, and a compound capable of generating Sn—F bonds wherein R is a substituted or unsubstituted hydrocarbyl ligand with 1 to 31 carbon atoms and an Sn—C bond and L is a hydrolysable ligand. The fluoride source can be an ammonium fluoride. The patterning structure on a substrate surface has RSnFn moieties, generally within an oxo-hydroxo network.
    Type: Application
    Filed: September 11, 2024
    Publication date: March 13, 2025
    Inventors: Brian J. Cardineau, Robert E. Jilek, Kai Jiang, Alexander C. Marwitz
  • Publication number: 20250074930
    Abstract: Organotin patterning compositions have radiation sensitive ligands with acetal functional groups. Precursor compositions are compositions comprising (OR4)(OR3)R2CR1SnL3, where the R groups are substituted or unsubstituted hydrocarbyl groups and L is a hydrolysable ligand. The precursors can be formed into coating that can be patterned with radiation, in particular EUV radiation. Coatings formed with blended precursors with hydrocarbyl-based ligands with some having acetal groups and others lacking acetal groups can be particularly effective for improving positive tone patterning.
    Type: Application
    Filed: August 27, 2024
    Publication date: March 6, 2025
    Inventors: Alexander C. Marwitz, Kai Jiang, Bryan T. Novas, Robert E. Jilek, Christopher J. Reed, Brian J. Cardineau, Munendra Yadav
  • Publication number: 20240427239
    Abstract: Organotin compositions suitable for radiation based patterning have ligands providing fluorinated groups and unsaturated carbon-carbon bonds, such as C?C bonds. The fluorinated groups and unsaturated carbon-carbon bonds may or may not be located on the same ligand. Blends of precursors with different ligands provide added flexibility with respect to precursor design. Fluorinated organometallic compounds can be represented by the formula RUFSn(OR?)3, wherein RUF is an organo group with 1 to 31 carbon atoms with at least one C?C bond and at least one fluorine atom bonded to a carbon, with the organo group forming a C—Sn bond, wherein R? is an organo group with 1 to 10 carbon atoms. Precursors are suitable for solution based deposition or vapor based deposition.
    Type: Application
    Filed: June 3, 2024
    Publication date: December 26, 2024
    Inventors: Robert E. Jilek, Christopher J. Reed
  • Publication number: 20240337941
    Abstract: As described herein, photosensitive composition comprises RSnL3, where R is a hydrocarbyl ligand with 1-20 carbon atoms and one or more silicon and/or germanium heteroatoms and L is an acetylide ligand (—C?CA, where A is a silyl group with 0 to 6 carbon atoms or an organo group with 1 to 10 carbon atoms). Methods are described wherein photosensitive compositions are synthesized by reacting RX, where X is a halide, and MSnL3, where M is an alkali metal, alkali earth metal or a pseudo-alkali earth metal, L is an acetylide or a dialkylamide. The radiation sensitive compositions are effective for radiation based patterning, such as with EUV light.
    Type: Application
    Filed: May 3, 2024
    Publication date: October 10, 2024
    Inventors: Robert E. Jilek, Kai Jiang, Amrit K. Narasimhan
  • Patent number: 12032291
    Abstract: As described herein, photosensitive composition comprises RSnL3, where R is a hydrocarbyl ligand with 1-20 carbon atoms and one or more silicon and/or germanium heteroatoms and L is an acetylide ligand (—C?CA, where A is a silyl group with 0 to 6 carbon atoms or an organo group with 1 to 10 carbon atoms). Methods are described wherein photosensitive compositions are synthesized by reacting RX, where X is a halide, and MSnL3, where M is an alkali metal, alkali earth metal or a pseudo-alkali earth metal, L is an acetylide or a dialkylamide. The radiation sensitive compositions are effective for radiation based patterning, such as with EUV light.
    Type: Grant
    Filed: February 28, 2022
    Date of Patent: July 9, 2024
    Assignee: Inpria Corporation
    Inventors: Robert E. Jilek, Kai Jiang, Amrit K. Narasimhan
  • Publication number: 20240199658
    Abstract: Synthesis techniques are described for forming organotin trialkoxide compounds via direct alkylation of tin alkoxides. A first method involves reacting an alkali metal tin trialkoxide with an organohalide compound (RXn, where X is a halide atom and n?1) to form a monoorgano tin trialkoxide represented by the formula R[Sn(OR?)3]n. The method can be used to form polytin trialkoxide compounds with a plurality of radiation sensitive C—Sn bonds. R and R? include organo groups and can optionally comprise hetero-atoms and/or unsaturated bonds. A second method involves the ultraviolet light-driven reaction of a di-tin tetraalkoxide with an organohalide compound (RX) to form a monoorgano trialkoxide represented by the formula RSn(OR?)3. A third method involves the visible or ultraviolet light-driven reaction of a di-tin tetraalkoxide or an alkali metal tin trialkoxide with an fluorinated organohalide compound (RFX) to form a fluorinated monoorgano trialkoxide represented by the formula RFSn(OR?)3.
    Type: Application
    Filed: November 30, 2023
    Publication date: June 20, 2024
    Inventors: Robert E. Jilek, Christopher J. Reed, Bryan Novas
  • Publication number: 20230374338
    Abstract: Organotin compositions having the formula RSnL3 and corresponding synthetic methods are described. R includes aromatic, cyclic and/or halogenated ether moieties, or polyethers, and L includes hydrolysable groups. The organotin compositions may be formed as radiation-patternable coatings on substrates. The coatings may have an average thickness from about 1 nm to about 75 nm and have the formula RSnOn(OH)3-2n, forming an oxo-hydroxo network, where R is a hydrocarbyl ether group with 1 to 30 carbon atoms and 0<n<3/2, wherein regions of the coating are soluble in 2-heptanone in a puddle development step following a bake at 150° C. for 120 seconds. The coatings may be radiation-patternable using UV, EUV or ion beam radiation, and corresponding methods are described.
    Type: Application
    Filed: May 17, 2023
    Publication date: November 23, 2023
    Inventors: Robert E. Jilek, Brian J. Cardineau, Lucy Su Xiao Huffman, Stephen T. Meyers
  • Publication number: 20220411446
    Abstract: Organotin compounds are presented that are represented by the formula RSnL3, wherein R is a deuterated hydrocarbyl group and L is a hydrolysable ligand. Two different synthesis techniques are described for synthesizing these compositions. A first method involves reacting a primary halide hydrocarbyl compound (R—X, where X is a halide atom) with an organometallic composition comprising SnL3 moieties associated with metal cations M, where M is an alkali metal, alkaline earth metal, and/or pseudo-alkaline earth metal (Zn, Cd, or Hg), and L is either an amide ligand resulting in an alkali metal tin triamide compound or an acetylide ligand resulting in an alkali metal tin triacetylide, to form correspondingly a monohydrocarbyl tin triamide (RSn(NR?2)3) or a monohydrocarbyl tin triacetylide (RSn(C?CRs)3).
    Type: Application
    Filed: February 28, 2022
    Publication date: December 29, 2022
    Inventors: Robert E. Jilek, Brian J. Cardineau, Kierra Huihui-Gist, Stephen T. Meyers
  • Publication number: 20220397826
    Abstract: As described herein, photosensitive composition comprises RSnL3, where R is a hydrocarbyl ligand with 1-20 carbon atoms and one or more silicon and/or germanium heteroatoms and L is an acetylide ligand (—C?CA, where A is a silyl group with 0 to 6 carbon atoms or an organo group with 1 to 10 carbon atoms). Methods are described wherein photosensitive compositions are synthesized by reacting RX, where X is a halide, and MSnL3, where M is an alkali metal, alkali earth metal or a pseudo-alkali earth metal, L is an acetylide or a dialkylamide. The radiation sensitive compositions are effective for radiation based patterning, such as with EUV light.
    Type: Application
    Filed: February 28, 2022
    Publication date: December 15, 2022
    Inventors: Robert E. Jilek, Kai Jiang, Amrit K. Narasimhan
  • Publication number: 20220064192
    Abstract: Synthesis reactions are described to efficiently and specifically form compounds of the structure RSnL3, where R is an organic ligand to the tin, and L is hydrolysable ligand or a hydrolysis product thereof. The synthesis is effective for a broad range of R ligands. The synthesis is based on the use of alkali metal ions and optionally alkaline earth (pseudo-alkaline earth) metal ions. Compounds are formed of the structures represented by the formulas RSn(C?CSiR?3)3, R?R?ACSnL3, where A is a halogen atom (F, Cl, Br or I) or an aromatic ring with at least one halogen substituent, R?R?(R??O)CSnL3 or R?R?(N?C)CSnZ3.
    Type: Application
    Filed: August 24, 2021
    Publication date: March 3, 2022
    Inventors: Joseph B. Edson, Brian J. Cardineau, William Earley, Kierra Huihui-Gist, Thomas J. Lamkin, Robert E. Jilek
  • Patent number: 11063297
    Abstract: An electrolyte, an electrochemical cell including the electrolyte, and a battery including the electrochemical cell are disclosed. Exemplary electrolytes allow for electrochemical cells and batteries with relatively high efficiency and stability that can be charged to relatively high voltages.
    Type: Grant
    Filed: December 19, 2018
    Date of Patent: July 13, 2021
    Assignee: Viking Power Systems Pte, Ltd.
    Inventors: Jocelyn M. Newhouse, Robert Ellis Doe, Craig M. Downie, Robert E. Jilek, Matthew J. Trahan