# US 12,180,404 B2 · Light-emitting body, method for producing light-emitting body, and biological material labeling agent > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,180,404 B2 - Document ID: US12180404B2 - Status: Granted - Kind: B2 - Application number: 17/507,055 - Filed: 2021-10-21 - Published: 2022-02-10 - Granted: 2024-12-31 - Earliest claimed: 2019-06-04 - Assignees: Murata Manufacturing Co., Ltd. - Applicants: Murata Manufacturing Co., Ltd. - Inventors: Takayoshi Murakami; Norikazu Fujihira - Web page: https://patentgrep.com/patent/US12180404B2 ## CPC - C01B 19/002: {Compounds containing, besides selenium or tellurium, more than one other element, with -O- and -OH not being considered as anions} - C09K 11/88: containing selenium, tellurium or unspecified chalcogen elements - C01G 15/006: {Compounds containing gallium, indium or thallium, with or without oxygen or hydrogen, and containing two or more other elements} - C09K 11/025: {non-luminescent particle coatings or suspension media} - C09K 11/08: containing inorganic luminescent materials - C09K 11/881: {Chalcogenides} - G01N 33/582: {with fluorescent label} - G01N 33/587: {Nanoparticles} - G01N 33/68: involving proteins, peptides or amino acids {(involving lipoproteins G01N33/92)} - B82Y 5/00: Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery - B82Y 20/00: Nanooptics, e.g. quantum optics or photonic crystals - B82Y 40/00: Manufacture or treatment of nanostructures - C01P 2004/64: Nanometer sized, i.e. from 1-100 nanometer - C01P 2006/60: Optical properties, e.g. expressed in CIELAB-values - C01B: NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; {METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C} - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - C01G: COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F (metal hydrides {monoborane, diborane or addition complexes thereof} C01B6/00; salts of oxyacids of halogens C01B11/00; peroxides, salts or peroxyacids C01B15/00; thiosulfates, dithionites, polythionates C01B17/64; compounds containing selenium, or tellurium C01B19/00; binary compounds of nitrogen with metals C01B21/06; azides C01B21/08; {compounds containing nitrogen, other non-metals and metal C01B21/082}; metal amides C01B21/092; nitrites C01B21/50; {compounds of noble gases C01B23/0005}; phosphides C01B25/08; salts of oxyacids of phosphorus C01B25/16; carbides C01B32/90; compounds containing silicon C01B33/00; compounds containing boron C01B35/00; compounds having molecular sieve properties but not having base-exchange properties C01B37/00; compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites, C01B39/00; cyanides C01C3/08; salts of cyanamide C01C3/16; thiocyanates C01C3/20) - G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q) - B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES - C01P: INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS ## Abstract A dispersion that includes water and a light-emitting body dispersed in the water. The light-emitting body contains a nanoparticle of a AgInSe compound semiconductor, and a film to which hydrophilicity is imparted by ultrasonic irradiation on a surface of the nanoparticle. The film has a double structure having a first organic molecular film containing an alkylthiol and a second organic molecular film composed mainly of a fatty acid. The light-emitting body has an emission quantum yield of 10% or more, an emission intensity peak wavelength in the range of 650 to 1000 nm, and a half-width ΔH of 100 nm or less at the emission intensity peak wavelength. ## Claims ### Claim 1 A dispersion comprising: water; and a light-emitting body dispersed in the water, the light-emitting body comprising: a nanoparticle of a compound semiconductor containing at least a Ag component, an In component, and a Se component; and a film with hydrophilicity on a surface of the nanoparticle, wherein the light-emitting body has an emission quantum yield of 10% or more and/or an emission intensity peak wavelength in a range of 650 to 1000 nm and a half-width of 100 nm or less at the emission intensity peak wavelength, the film has a double structure having a first organic molecular film containing at least an alkylthiol and a second organic molecular film composed mainly of a fatty acid with a plurality of alkyl groups and the hydrophilicity is imparted by ultrasonic irradiation. ### Claim 2 (depends on 1) The dispersion according to claim 1, wherein the emission quantum yield is 50% or less. ### Claim 3 (depends on 1) The dispersion according to claim 1, wherein the alkylthiol is 1-dodecanethiol. ### Claim 4 (depends on 1) The dispersion according to claim 1, wherein the fatty acid is oleic acid. ### Claim 5 (depends on 1) The dispersion according to claim 1, wherein the alkyl groups of the fatty acid have a longer chain length than the alkyl group of the alkylthiol. ### Claim 6 (depends on 1) The dispersion according to claim 1, wherein the first organic molecular film contains a surface protective agent containing n-octyl thioglycolate. ### Claim 7 (depends on 1) The dispersion according to claim 1, wherein the first organic molecular film contains a surface protective agent containing 1-dodecanethiol. ### Claim 8 (depends on 1) The dispersion according to claim 1, wherein the emission quantum yield is 30% or more. ### Claim 9 (depends on 1) The dispersion according to claim 1, wherein the nanoparticle contains a Ga component. ### Claim 10 (depends on 1) The dispersion according to claim 1, wherein the light-emitting body has a transmittance of 90% or more in a wavelength range of 1000 to 1100 nm. ### Claim 11 (depends on 1) The dispersion according to claim 1, wherein the In component is contained in a larger amount than a stoichiometric composition. ### Claim 12 (depends on 1) The dispersion according to claim 1, wherein the film is covered with a surface modifier containing a cationic cell-penetrating peptide. ### Claim 13 (depends on 12) The dispersion according to claim 12, wherein the cell-penetrating peptide is octaarginine. ### Claim 14 (depends on 12) The dispersion according to claim 12, wherein the light-emitting body introduced into an adipose-derived stem cell at 160 nmol/L on a molar concentration basis has a cell survival rate of 80% or more. ### Claim 15 A method for producing a dispersion, the method comprising: preparing a nonpolar nanoparticle dispersion liquid in which nanoparticles of a compound semiconductor containing at least a Ag component, an In component, and a Se component are dispersed in a nonpolar solvent; preparing a precursor dispersion liquid by adding organic molecules including at least an alkylthiol to the nonpolar nanoparticle dispersion liquid to form a first organic molecular film on a surface of each nanoparticle; preparing a fatty acid aqueous solution in which a fatty acid with a plurality of alkyl groups is dissolved in water in the presence of an alkali; mixing the precursor dispersion liquid and the fatty acid aqueous solution to prepare a phase-separated solution containing a nonpolar solvent phase and an aqueous phase; applying ultrasonic waves to the phase-separated solution to form a film with hydrophilicity on a surface of each nanoparticle; and dispersing the nanoparticles in water to prepare an aqueous nanoparticle dispersion. ### Claim 16 (depends on 15) The method for producing a dispersion according to claim 15, wherein the forming of the film on the surface of each nanoparticle includes forming an oil-in-water microemulsion by the ultrasonic irradiation so as to confine the nanoparticles with the first organic molecular film formed thereon and the fatty acid in the microemulsion to adsorb the fatty acid on the surface of each nanoparticle. ### Claim 17 (depends on 15) The method for producing a dispersion according to claim 15, wherein the preparing of the nonpolar nanoparticle dispersion liquid includes: dissolving a Ag compound and an In compound in a solvent to prepare a Ag—In solution; dissolving a Se powder in a solvent to prepare a Se solution; injecting the Se solution into the Ag—In solution while the Ag—In solution is heated to a predetermined temperature to prepare a mixed solution; and heating the mixed solution at a reaction temperature higher than the predetermined temperature for a predetermined reaction time to produce a nanoparticle of a compound semiconductor covered with a surface protective agent. ### Claim 18 (depends on 15) The method for producing a dispersion according to claim 15, wherein the preparing of the nonpolar nanoparticle dispersion liquid includes: dissolving a Ag compound, an In compound, and a Ga compound in a solvent to prepare a Ag—In—Ga solution; dissolving a Se powder in a solvent to prepare a Se solution; injecting the Se solution into the Ag—In—Ga solution while the Ag—In—Ga solution is heated to a predetermined temperature to prepare a mixed solution; and heating the mixed solution at a reaction temperature higher than the predetermined temperature for a predetermined reaction time to produce a nanoparticle of a compound semiconductor covered with a surface protective agent. ### Claim 19 (depends on 15) The method for producing a dispersion according to claim 15, further comprising mixing the nanoparticles with the film formed thereon and a surface modifier comprising a cationic cell-penetrating peptide so as to cover a surface of the film with the surface modifier. ### Claim 20 (depends on 19) The method for producing a dispersion according to claim 19, wherein the cell-penetrating peptide is octaarginine. ### Claim 21 (depends on 1) A biological material labeling agent comprising the dispersion according to claim 1.