CA2502669A1 - Stabilized semiconductor nanocrystals - Google Patents

Stabilized semiconductor nanocrystals Download PDF

Info

Publication number
CA2502669A1
CA2502669A1 CA002502669A CA2502669A CA2502669A1 CA 2502669 A1 CA2502669 A1 CA 2502669A1 CA 002502669 A CA002502669 A CA 002502669A CA 2502669 A CA2502669 A CA 2502669A CA 2502669 A1 CA2502669 A1 CA 2502669A1
Authority
CA
Canada
Prior art keywords
substituted
group
nanocrystal
unsubstituted
independently
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002502669A
Other languages
French (fr)
Other versions
CA2502669C (en
Inventor
Moungi G. Bawendi
Sungjee Kim
Nathan E. Stott
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Massachusetts Institute of Technology
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2502669A1 publication Critical patent/CA2502669A1/en
Application granted granted Critical
Publication of CA2502669C publication Critical patent/CA2502669C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B19/00—Selenium; Tellurium; Compounds thereof
    • C01B19/007—Tellurides or selenides of metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G11/00—Compounds of cadmium
    • C01G11/02—Sulfides
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G13/00—Compounds of mercury
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G21/00—Compounds of lead
    • C01G21/21—Sulfides
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G28/00—Compounds of arsenic
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G9/00—Compounds of zinc
    • C01G9/08—Sulfides
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5004—Acyclic saturated phosphines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/56—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing sulfur
    • C09K11/562—Chalcogenides
    • C09K11/565—Chalcogenides with zinc cadmium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/88—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing selenium, tellurium or unspecified chalcogen elements
    • C09K11/881—Chalcogenides
    • C09K11/883—Chalcogenides with zinc or cadmium
    • C—CHEMISTRY; METALLURGY
    • C30—CRYSTAL GROWTH
    • C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
    • C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
    • C30B29/60—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape characterised by shape
    • C—CHEMISTRY; METALLURGY
    • C30—CRYSTAL GROWTH
    • C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
    • C30B7/00—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/30—Particle morphology extending in three dimensions
    • C01P2004/40—Particle morphology extending in three dimensions prism-like
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/12—All metal or with adjacent metals
    • Y10T428/12493—Composite; i.e., plural, adjacent, spatially distinct metal components [e.g., layers, joint, etc.]
    • Y10T428/12535—Composite; i.e., plural, adjacent, spatially distinct metal components [e.g., layers, joint, etc.] with additional, spatially distinct nonmetal component
    • Y10T428/12597—Noncrystalline silica or noncrystalline plural-oxide component [e.g., glass, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
    • Y10T428/2995—Silane, siloxane or silicone coating
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
    • Y10T428/2996—Glass particles or spheres
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2998—Coated including synthetic resin or polymer

Abstract

A semiconductor nanocrystal associated with a polydentate ligand. The polydentate ligand stabilizes the nanocyrstal.

Claims (59)

1. A semiconductor nanocrystal comprising:
a semiconductor nanocrystal; and an outer layer including a polydentate ligand bound to the nanocrystal by three or more donor groups, each donor group independently selected from the group consisting of P, N, P=O, and N=O.
2. The nanocrystal of claim 1, wherein the polydentate ligand has the formula:
wherein n is 1, 2, 3, 4 or 5, m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, each k is 1, 2, 3, or 4, each X independently is a donor group selected from the group consisting of N, P, P=O, and N=O, each Y is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted aryloxy, and L is a linking group optionally terminated by O and includes at least one carbonate, carbamate, amide, ester or ether linkage.
3. The nanocrystal of claim 1, wherein the polydentate ligand has the formula:
wherein n is 1, 2 or 3, m is 1, 2, 3, 4, or 5, each k is 1 or 2, each X
independently is a donor group selected from the group consisting of N, P, P=O, and N=O, each Y is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted aryloxy, and L is a linking group optionally terminated by O and includes at least one carbonate, carbamate, amide, ester or ether linkage.
4. The nanocrystal of claim 3, wherein each X is P or P=O, and L includes at least one carbamate linkage.
5. The nanocrystal of claim 4, wherein each Y is unsubstituted alkyl.
6. The nanocrystal of claim 4, wherein each Y includes a carboxylic acid.
7. The nanocrystal of claim 4, wherein each Y includes an acrylate group.
8. The nanocrystal of claim 1, wherein the polydentate ligand has the formula:
wherein each n independently is 1, 2 or 3, each m independently is 1, 2, 3, 4, or 5, each k is 1 or 2, each X independently is a donor group selected from the group consisting of N, P, P=O, and N=O, each Y is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted aryloxy, L is a linking group optionally terminated by O and includes at least one carbonate, carbamate, amide, ester or ether linkage, L' is a bond or a cross-linking group, and Y'-L'-Y' is derived from cross-linking of Y.
9. The nanocrystal of claim 1 wherein the polydentate ligand has the formula:
wherein p is 1 or 2, each m is 1, 2, 3, 4, or 5, each k is 1 or 2, each j is 0 or 1, each p is 0 or 1, q is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, each X independently is a donor group selected from the group consisting of N, P, P=O, and N=O, each Y is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted aryloxy, and L is a linking group optionally terminated by O and includes at least one carbonate, carbamate, amide, ester or ether linkage.
10. The nanocrystal of claim 1, wherein the polydentate ligand has the formula:
wherein n is 1, 2 or 3, m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, each k is 1 or 2, each x independently is 0 or 1, each of Z1 and Z2, independently, is an ether, amide, ester, carbamate or carbonate linkage, each R1 and R2, independently, is an alkylene optionally interrupted by S, O, NH, N-lower alkyl, arylene, heteroarylene, or aralkylene and optionally terminated by S, O, NH, N-lower alkyl, arylene, heteroarylene, or aralkylene, and each R is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted aryl.
11. The nanocrystal of claim 10, wherein Z1 is a carbamate linkage and Z2 is a carbamate linkage.
12. The nanocrystal of claim 10, wherein R1 is an alkylene and R2 is an alkylene.
13. The nanocrystal of claim 11, wherein R1 is an alkylene and R2 is an alkylene.
14. The nanocrystal of claim 1, wherein the polydentate ligand has the formula:
wherein n is 1, 2 or 3, m is 1, 2, 3, 4, or 5, each k is 1 or 2, each x independently is 0 or 1, Z is an ether, carbamate, or carbonate linkage, each R1 and each R2, independently, is an alkylene optionally interrupted by S, O, NH, N-lower alkyl, arylene, heteroarylene, or aralkylene, and optionally terminated by S, O, NH, N-lower alkyl, arylene, heteroarylene, or aralkylene, and each R is substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, and each R is bonded to R1 via an ether, ester, amide, carbamate or carbonate linkage.
15. The nanocrystal of claim 1, wherein the polydentate ligand has the formula:
wherein n is 1, 2 or 3, m is 1, 2, 3, 4, or 5, each k is 1 or 2, each x independently is 0 or 1, and each R is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted aryl.
16. The nanocrystal of claim 15, wherein R has the formula:
17. The nanocrystal of claim 15, wherein R has the formula:
18. The nanocrystal of claim 15, wherein R has the formula:
19. The nanocrystal of claim 15, wherein R has the formula:
20. The nanocrystal of claim 1, wherein the polydentate ligand has the formula:

wherein n is 1, 2 or 3, m is 1, 2, 3, 4, or 5, and each k is 1 or 2, each x independently is 0 or 1, each R is substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, L' is a bond or a cross-linking group, and R'-L'-R' is derived from cross-linking of R.
21. The nanocrystal of claim 20, wherein each R includes a carboxylic acid and R'-L'-R' includes the fragment:

wherein A is alkylene or arylene.
22. The nanocrystal of claim 20, wherein each R includes an acrylate group and R'-L'-R' includes the fragment:

wherein A' is H or C1-C4 alkyl.
23. The nanocrystal of claim 1, wherein the semiconductor nanocrystal includes a core of a first semiconductor material.
24. The nanocrystal of claim 23, wherein the first semiconductor material is a Group II-VI compound, a Group II-V compound, a Group III-VI compound, a Group III-V compound, a Group IV-VI compound, a Group I-III-VI compound, a Group II-IV-VI
compound, or a Group II-IV-V compound.
25. The nanocrystal of claim 23, wherein the first semiconductor material is ZnS, ZnSe, ZnTe, CdS, CdSe, CdTe, HgS, HgSe, HgTe, AlN, AlP, AlAs, AlSb, GaN, GaP, GaAs, GaSb, GaSe, InN, InP, InAs, InSb, TlN, TlP, TIAs, TlSb, PbS, PbSe, PbTe, or mixtures thereof.
26. The nanocrystal of claim 23, wherein the semiconductor nanocrystal includes a second semiconductor material overcoated on the first semiconductor material.
27. The nanocrystal of claim 26, wherein the first semiconductor material has a first band gap, and the second semiconductor material has a second band gap that is larger than the first band gap.
28. The nanocrystal of claim 26, wherein the second semiconductor material is a Group II-VI compound, a Group II-V compound, a Group III-VI compound, a Group III-V compound, a Group IV-VI compound, a Group I-III-VI compound, a Group II-IV-VI compound, or a Group II-IV-V compound.
29. The nanocrystal of claim 26, wherein the second semiconductor material is ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, MgO, MgS, MgSe, MgTe, HgO, HgS, HgSe, HgTe, AlN, AlP, AlAs, AlSb, GaN, GaP, GaAs, GaSb, InN, InP, InAs, InSb, TlN, TlP, TlAs, TlSb, TlSb, PbS, PbSe, PbTe, or mixtures thereof.
30. A semiconductor nanocrystal, comprising a semiconductor nanocrystal and an outer layer including a polydentate ligand bound to the nanocrystal by three or more donor groups, each donor group independently selected from the group consisting of P, N, P=O, and N=O, wherein the luminescence of the nanocrystal decreases by no more than 50% after incubating for 24 hours in fetal bovine serum maintained at 37 °C.
31. A semiconductor nanocrystal comprising:
a semiconductor nanocrystal; and an outer layer including a plurality of polydentate ligands, each polydentate ligand bound to the nanocrystal by three or more donor groups, each donor group independently selected from the group consisting of P, N, P=O, and N=O, the plurality of polydentate ligands being a distribution of oligomers.
32. A method of making a stabilized nanocrystal comprising contacting a nanocrystal with a polydentate ligand having three or more donor groups, each donor group independently selected from the group consisting of P, N, P=O, and N=O, to form the stabilized nanocrystal.
33. The method of claim 32, wherein the polydentate ligand is a member of a distribution of oligomers.
34. The method of claim 32, further comprising cross-linking the polydentate ligand after contacting.
35. The method of claim 34, wherein the polydentate ligand includes a carboxylic acid group.
36. The method of claim 35, wherein cross-linking includes contacting the polydentate ligand with a diamine and a coupling agent.
37. The method of claim 34, wherein the polydentate ligand includes an acrylate group.
38. The method of claim 37, wherein cross-linking includes contacting the polydentate ligand with a radical initiator.
39. A polydentate ligand of formula:
wherein n is 1, 2, 3, 4 or 5, m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, each k is 1, 2, 3, or 4, each X independently is a donor group selected from the group consisting of N, P, P=O, and N=O, each Y is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted aryloxy, and L is a linking group optionally terminated by O and includes at least one carbonate, carbamate, amide, ester or ether linkage.
40. A polydentate ligand of formula:
wherein n is 1, 2 or 3, m is 1, 2, 3, 4, or 5, each k is 1 or 2, each X
independently is a donor group selected from the group consisting of N, P, P=O, and N=O, each Y is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted aryloxy, and L is a linking group optionally terminated by O and includes at least one carbonate, caxbamate, amide, ester or ether linkage.
41. A distribution of polydentate ligands of formula:
wherein n is 1, 2 or 3, m is 1, 2, 3, 4, or 5, each k is 1 or 2, each X
independently is a donor group selected from the group consisting of N, P, P=O, and N=O, each Y is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted aryloxy, L is a linking group optionally terminated by O and includes at least one carbonate, carbamate, amide, ester or ether linkage, and the distribution includes at least two members with different values of m.
42. A polydentate ligand of formula:
wherein p is 1 or 2, each m is 1, 2, 3, 4, or 5, each k is 1 or 2, each j is 0 or 1, each p is 0 or 1, q is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, each X independently is a donor group selected from the group consisting of N, P, P=O, and N=O, each Y is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted aryloxy, and L is a linking group optionally terminated by O and includes at least one carbonate, carbamate, amide, ester or ether linkage.
43. A polydentate ligand of formula:
wherein n is 1, 2 or 3, m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, each k is 1 or 2, each x independently is 0 or 1, each of Z1 and Z2, independently, is an ether, amide, ester, carbamate or carbonate linkage, each R1 and R2, independently, is an alkylene optionally interrupted by S, O, NH, N-lower alkyl, arylene, heteroarylene, or aralkylene and optionally terminated by S, O, NH, N-lower alkyl, arylene, heteroarylene, or aralkylene, and each R is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted aryl.
44. A polydentate ligand of formula:
wherein n is 1, 2 or 3, m is 1, 2, 3, 4, or 5, each k is 1 or 2, each x independently is 0 or 1, Z is an ether, carbamate, amide, ester or carbonate linkage, each R1 and each R2, independently, is an alkylene optionally interrupted by S, O, NH, N-lower alkyl, arylene, heteroarylene, or aralkylene, and optionally terminated by S, O, NH, N-lower alkyl, arylene, heteroarylene, or aralkylene, and each R is substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, and each R is bonded to R1 via an ether, ester, amide, carbamate or carbonate linkage.
45. A polydentate ligand of formula:
wherein n is 1, 2 or 3, m is 1, 2, 3, 4, or 5, each k is 1 or 2, each x indenpendently is 0 or 1, and each R is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted aryl.
46. The ligand of claim 45, wherein at least one x is 0.
47. The ligand of claim 45, wherein each x is 0.
48. The ligand of claim 45, wherein each R is unsubstituted alkyl.
49. The ligand of claim 45, wherein each R includes a carboxylic acid group.
50. The ligand of claim 45, wherein each R includes an acrylate group.
51. A method of making a polydentate ligand comprising contacting a monomeric, polyfunctional phosphine with a polyfunctional oligomerization reagent to form an oligomeric phosphine.
52. The method of claim 51, wherein the monomeric, polyfunctional phosphine is trishydroxypropylphosphine.
53. The method of claim 52, wherein the polyfunctional oligomerization reagent is a diisocyanate.
54. The method of claim 51, further comprising contacting the oligomeric phosphine with an isocyanate of formula: R'-L-NCO, wherein L is C2-C24 alkylene, and R' has the formula:

R' has the formula:

or R' is hydrogen, wherein R a is hydrogen or C1-C4 alkyl.
55. A method of making a nanocrystal-biomolecule conjugate comprising contacting a nanocrystal including a polydentate ligand including a reactive group with a biomolecule.
56. The method of claim 55, wherein the biomolecule is a polypeptide.
57. The method of claim 55, further comprising contacting the nanocrystal and the biomolecule with a cross-linking agent.
58. The method of claim 57, wherein the reactive group is a carboxylic acid.
59. The method of claim 58, wherein the biomolecule includes an amino group and the cross-linking agent is a carbodiimide.
CA2502669A 2002-08-15 2003-08-15 Stabilized semiconductor nanocrystals Expired - Lifetime CA2502669C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US40336702P 2002-08-15 2002-08-15
US60/403,367 2002-08-15
PCT/US2003/025613 WO2004042784A2 (en) 2002-08-15 2003-08-15 Stabilized semiconductor nanocrystals

Publications (2)

Publication Number Publication Date
CA2502669A1 true CA2502669A1 (en) 2004-05-21
CA2502669C CA2502669C (en) 2012-10-23

Family

ID=32312445

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2502669A Expired - Lifetime CA2502669C (en) 2002-08-15 2003-08-15 Stabilized semiconductor nanocrystals

Country Status (6)

Country Link
US (3) US7160613B2 (en)
EP (1) EP1576655B1 (en)
JP (2) JP2006502232A (en)
AU (1) AU2003301769A1 (en)
CA (1) CA2502669C (en)
WO (1) WO2004042784A2 (en)

Families Citing this family (121)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6607829B1 (en) * 1997-11-13 2003-08-19 Massachusetts Institute Of Technology Tellurium-containing nanocrystalline materials
US6207392B1 (en) 1997-11-25 2001-03-27 The Regents Of The University Of California Semiconductor nanocrystal probes for biological applications and process for making and using such probes
JP2006502232A (en) * 2002-08-15 2006-01-19 モウンギ ジー． バウエンディ Stabilized semiconductor nanocrystals
US7767260B2 (en) * 2003-01-22 2010-08-03 The Board Of Trustees Of The University Of Arkansas Monodisperse core/shell and other complex structured nanocrystals and methods of preparing the same
US7229497B2 (en) * 2003-08-26 2007-06-12 Massachusetts Institute Of Technology Method of preparing nanocrystals
US7742322B2 (en) * 2005-01-07 2010-06-22 Invisage Technologies, Inc. Electronic and optoelectronic devices with quantum dot films
US7773404B2 (en) * 2005-01-07 2010-08-10 Invisage Technologies, Inc. Quantum dot optical devices with enhanced gain and sensitivity and methods of making same
US7326908B2 (en) 2004-04-19 2008-02-05 Edward Sargent Optically-regulated optical emission using colloidal quantum dot nanocrystals
US7746681B2 (en) * 2005-01-07 2010-06-29 Invisage Technologies, Inc. Methods of making quantum dot films
US20070045777A1 (en) * 2004-07-08 2007-03-01 Jennifer Gillies Micronized semiconductor nanocrystal complexes and methods of making and using same
US7229690B2 (en) * 2004-07-26 2007-06-12 Massachusetts Institute Of Technology Microspheres including nanoparticles
US7316967B2 (en) * 2004-09-24 2008-01-08 Massachusetts Institute Of Technology Flow method and reactor for manufacturing noncrystals
US8891575B2 (en) * 2004-11-30 2014-11-18 Massachusetts Institute Of Technology Optical feedback structures and methods of making
CA2519608A1 (en) 2005-01-07 2006-07-07 Edward Sargent Quantum dot-polymer nanocomposite photodetectors and photovoltaics
US8134175B2 (en) 2005-01-11 2012-03-13 Massachusetts Institute Of Technology Nanocrystals including III-V semiconductors
JP4846241B2 (en) * 2005-01-21 2011-12-28 株式会社東芝 Photorefractive index change element
US7811479B2 (en) * 2005-02-07 2010-10-12 The Trustees Of The University Of Pennsylvania Polymer-nanocrystal quantum dot composites and optoelectronic devices
CN101208605A (en) * 2005-05-04 2008-06-25 新加坡科技研究局 New type water-solubility nanocrystalline containing low molecular weight coating agent and preparation method thereof
US8845927B2 (en) * 2006-06-02 2014-09-30 Qd Vision, Inc. Functionalized nanoparticles and method
US9297092B2 (en) * 2005-06-05 2016-03-29 Qd Vision, Inc. Compositions, optical component, system including an optical component, devices, and other products
US8718437B2 (en) 2006-03-07 2014-05-06 Qd Vision, Inc. Compositions, optical component, system including an optical component, devices, and other products
WO2007021757A2 (en) 2005-08-15 2007-02-22 Massachusetts Institute Of Technology Fluorescent sensor and methods
JP2009526370A (en) * 2006-02-09 2009-07-16 キユーデイー・ビジヨン・インコーポレーテツド Devices and methods comprising layers comprising semiconductor nanocrystals and doped organic materials
US8835941B2 (en) * 2006-02-09 2014-09-16 Qd Vision, Inc. Displays including semiconductor nanocrystals and methods of making same
KR100713745B1 (en) * 2006-02-27 2007-05-07 연세대학교 산학협력단 Water-soluble magnetic or metal oxide nanoparticles coated with ligands and preparation method thereof
US9874674B2 (en) 2006-03-07 2018-01-23 Samsung Electronics Co., Ltd. Compositions, optical component, system including an optical component, devices, and other products
EP2041478B1 (en) * 2006-03-07 2014-08-06 QD Vision, Inc. An article including semiconductor nanocrystals
WO2007143197A2 (en) * 2006-06-02 2007-12-13 Qd Vision, Inc. Light-emitting devices and displays with improved performance
US9701899B2 (en) * 2006-03-07 2017-07-11 Samsung Electronics Co., Ltd. Compositions, optical component, system including an optical component, devices, and other products
US8849087B2 (en) * 2006-03-07 2014-09-30 Qd Vision, Inc. Compositions, optical component, system including an optical component, devices, and other products
WO2007112088A2 (en) * 2006-03-24 2007-10-04 Qd Vision, Inc. Hyperspectral imaging device
US20080038558A1 (en) * 2006-04-05 2008-02-14 Evident Technologies, Inc. I-iii-vi semiconductor nanocrystals, i-iii-vi water stable semiconductor nanocrystals, and methods of making same
WO2007117668A2 (en) * 2006-04-07 2007-10-18 Qd Vision, Inc. Methods and articles including nanomaterial
WO2007120877A2 (en) * 2006-04-14 2007-10-25 Qd Vision, Inc. Transfer surface for manufacturing a light emitting device
US8941299B2 (en) * 2006-05-21 2015-01-27 Massachusetts Institute Of Technology Light emitting device including semiconductor nanocrystals
US9212056B2 (en) * 2006-06-02 2015-12-15 Qd Vision, Inc. Nanoparticle including multi-functional ligand and method
WO2007143227A2 (en) * 2006-06-10 2007-12-13 Qd Vision, Inc. Materials,thin films,optical filters, and devices including same
WO2008105792A2 (en) * 2006-06-24 2008-09-04 Qd Vision, Inc. Methods for depositing nanomaterial, methods for fabricating a device, methods for fabricating an array of devices and compositions
WO2008108798A2 (en) 2006-06-24 2008-09-12 Qd Vision, Inc. Methods for depositing nanomaterial, methods for fabricating a device, and methods for fabricating an array of devices
WO2008111947A1 (en) * 2006-06-24 2008-09-18 Qd Vision, Inc. Methods and articles including nanomaterial
US8643058B2 (en) * 2006-07-31 2014-02-04 Massachusetts Institute Of Technology Electro-optical device including nanocrystals
JP2010508620A (en) * 2006-09-12 2010-03-18 キユーデイー・ビジヨン・インコーポレーテツド Electroluminescent display useful for displaying a predetermined pattern
WO2008033388A2 (en) * 2006-09-12 2008-03-20 Qd Vision, Inc. A composite including nanoparticles, methods, and products including a composite
DE102006047103A1 (en) * 2006-09-28 2008-04-03 Siemens Ag Powder for cold gas spraying
WO2008133660A2 (en) 2006-11-21 2008-11-06 Qd Vision, Inc. Nanocrystals including a group iiia element and a group va element, method, composition, device and other prodcucts
WO2008063653A1 (en) 2006-11-21 2008-05-29 Qd Vision, Inc. Semiconductor nanocrystals and compositions and devices including same
WO2008063652A1 (en) 2006-11-21 2008-05-29 Qd Vision, Inc. Blue emitting semiconductor nanocrystals and compositions and devices including same
WO2008063658A2 (en) 2006-11-21 2008-05-29 Qd Vision, Inc. Semiconductor nanocrystals and compositions and devices including same
WO2008063657A2 (en) * 2006-11-21 2008-05-29 Qd Vision, Inc. Light emitting devices and displays with improved performance
US8836212B2 (en) * 2007-01-11 2014-09-16 Qd Vision, Inc. Light emissive printed article printed with quantum dot ink
US8222061B2 (en) * 2007-03-30 2012-07-17 The Penn State Research Foundation Mist fabrication of quantum dot devices
JP5773646B2 (en) 2007-06-25 2015-09-02 キユーデイー・ビジヨン・インコーポレーテツド Compositions and methods comprising depositing nanomaterials
WO2009002551A1 (en) * 2007-06-26 2008-12-31 Qd Vision, Inc. Photovoltaic devices including quantum dot down-conversion materials useful for solar cells and materials including quantum dots
US8947516B2 (en) * 2007-09-26 2015-02-03 Massachusetts Institute Of Technology High-resolution 3D imaging of single semiconductor nanocrystals
WO2009099425A2 (en) 2008-02-07 2009-08-13 Qd Vision, Inc. Flexible devices including semiconductor nanocrystals, arrays, and methods
WO2009145813A1 (en) 2008-03-04 2009-12-03 Qd Vision, Inc. Particles including nanoparticles, uses thereof, and methods
KR101995369B1 (en) 2008-04-03 2019-07-02 삼성 리서치 아메리카 인코포레이티드 Light-emitting device including quantum dots
US9525148B2 (en) 2008-04-03 2016-12-20 Qd Vision, Inc. Device including quantum dots
EP2297762B1 (en) 2008-05-06 2017-03-15 Samsung Electronics Co., Ltd. Solid state lighting devices including quantum confined semiconductor nanoparticles
WO2009137053A1 (en) 2008-05-06 2009-11-12 Qd Vision, Inc. Optical components, systems including an optical component, and devices
US9207385B2 (en) 2008-05-06 2015-12-08 Qd Vision, Inc. Lighting systems and devices including same
US8765223B2 (en) * 2008-05-08 2014-07-01 Air Products And Chemicals, Inc. Binary and ternary metal chalcogenide materials and method of making and using same
US8507040B2 (en) 2008-05-08 2013-08-13 Air Products And Chemicals, Inc. Binary and ternary metal chalcogenide materials and method of making and using same
AU2009288017A1 (en) * 2008-09-03 2010-03-11 Emory University Quantum dots, methods of making quantum dots, and methods of using quantum dots
WO2010039897A2 (en) * 2008-10-03 2010-04-08 Life Technologies Corporation Nanocrystals with functional ligands
US20100264371A1 (en) * 2009-03-19 2010-10-21 Nick Robert J Composition including quantum dots, uses of the foregoing, and methods
US8263639B2 (en) * 2009-04-21 2012-09-11 The United States Of America, As Represented By The Secretary Of The Navy Multifunctional metal-chelating ligands
JP5710597B2 (en) 2009-04-28 2015-04-30 キユーデイー・ビジヨン・インコーポレーテツド Optical material, optical component and method
US20100278734A1 (en) * 2009-04-29 2010-11-04 General Electric Company Nanoparticle contrast agents for diagnostic imaging
US20100278748A1 (en) * 2009-04-29 2010-11-04 General Electric Company Nanoparticle contrast agents for diagnostic imaging
US20100278749A1 (en) * 2009-04-29 2010-11-04 General Electric Company Nanoparticle contrast agents for diagnostic imaging
US8106420B2 (en) * 2009-06-05 2012-01-31 Massachusetts Institute Of Technology Light emitting device including semiconductor nanocrystals
CN102598313B (en) 2009-08-14 2016-03-23 Qd视光有限公司 Luminescent device, for the optical element of luminescent device and method
US8894891B2 (en) * 2009-08-16 2014-11-25 Massachusetts Institute Of Technology Copolymer-associated nanomaterial
WO2011031876A1 (en) 2009-09-09 2011-03-17 Qd Vision, Inc. Formulations including nanoparticles
EP2475717A4 (en) 2009-09-09 2015-01-07 Qd Vision Inc Particles including nanoparticles, uses thereof, and methods
KR101791580B1 (en) 2009-10-17 2017-10-30 삼성전자주식회사 An optical component, products including same, and methods for making same
WO2011060180A1 (en) 2009-11-11 2011-05-19 Qd Vision, Inc. Device including quantum dots
US8222449B2 (en) * 2009-12-08 2012-07-17 The United States Of America, As Represented By The Secretary Of The Navy Metal oxide-chelating ligands
US9382470B2 (en) 2010-07-01 2016-07-05 Samsung Electronics Co., Ltd. Thiol containing compositions for preparing a composite, polymeric composites prepared therefrom, and articles including the same
US8399939B2 (en) 2010-12-03 2013-03-19 Massachusetts Institute Of Technology Color selective photodetector and methods of making
WO2013019299A2 (en) 2011-05-11 2013-02-07 Qd Vision, Inc. Method for processing devices including quantum dots and devices
WO2012158832A2 (en) 2011-05-16 2012-11-22 Qd Vision, Inc. Method for preparing semiconductor nanocrystals
TW201248894A (en) 2011-05-16 2012-12-01 Qd Vision Inc Device including quantum dots and method for making same
WO2013028253A1 (en) 2011-08-19 2013-02-28 Qd Vision, Inc. Semiconductor nanocrystals and methods
KR101575139B1 (en) 2011-12-09 2015-12-08 삼성전자주식회사 Backlight Unit and Liquid Crystal Display Including Same
WO2013103440A1 (en) 2012-01-06 2013-07-11 Qd Vision, Inc. Light emitting device including blue emitting quantum dots and method
US9176219B2 (en) 2012-03-07 2015-11-03 The Boeing Company Frequency field scanning
KR102093258B1 (en) 2012-08-06 2020-03-26 루미리즈 홀딩 비.브이. Highly stable qds-composites for solid state lighting and the method of making them through initiator-free polymerization
WO2014147570A1 (en) 2013-03-20 2014-09-25 Koninklijke Philips N.V. Encapsulated quantum dots in porous particles
JP6407286B2 (en) 2013-12-17 2018-10-17 スリーエム イノベイティブ プロパティズ カンパニー Composite nanoparticles containing phthalic acid derivatives
CN105814169B (en) 2013-12-17 2018-05-25 3M创新有限公司 Composite nanoparticle comprising malonate derivative
CN105940081B (en) 2014-02-04 2020-06-09 亮锐控股有限公司 Complex inorganic ligands based on coordinated oxygen and hydroxyl for quantum dots
US10340427B2 (en) 2014-02-04 2019-07-02 Lumileds Llc Quantum dots with inorganic ligands in an inorganic matrix
JP6600640B2 (en) 2014-03-10 2019-10-30 スリーエム イノベイティブ プロパティズ カンパニー Composite nanoparticles containing thiol-substituted silicone
WO2015153148A1 (en) 2014-04-02 2015-10-08 3M Innovative Properties Company Composite nanoparticles including a thioether ligand
JP6589318B2 (en) * 2015-03-23 2019-10-16 コニカミノルタ株式会社 Color gamut expansion film
JP6729554B2 (en) * 2015-03-23 2020-07-22 コニカミノルタ株式会社 Composition and optically functional film containing the same
CN108026444B (en) 2015-09-15 2020-08-04 3M创新有限公司 Additive stabilized composite nanoparticles
US10829687B2 (en) 2015-09-15 2020-11-10 3M Innovative Properties Company Additive stabilized composite nanoparticles
EP3163372B1 (en) * 2015-10-26 2020-04-29 Samsung Electronics Co., Ltd. Quantum dot having polymeric outer layer, photosensitive compositions including the same, and quantum dot polymer composite pattern produced therefrom
WO2017087170A1 (en) 2015-11-18 2017-05-26 3M Innovative Properties Company Copolymeric stabilizing carrier fluid for nanoparticles
US10899961B2 (en) 2016-02-17 2021-01-26 3M Innovative Properties Company Quantum dots with stabilizing fluorochemical copolymers
WO2017142781A1 (en) 2016-02-17 2017-08-24 3M Innovative Properties Company Matrix for quantum dot film article
KR20180128956A (en) 2016-04-01 2018-12-04 쓰리엠 이노베이티브 프로퍼티즈 컴파니 Quantum dots with fluorochemical stabilizers
CN109790452A (en) 2016-05-20 2019-05-21 3M创新有限公司 Quantum dot with mixed amine and mercaptan ligand
KR20190031505A (en) 2016-07-20 2019-03-26 쓰리엠 이노베이티브 프로퍼티즈 컴파니 Stabilized styrene polymers for quantum dots
US11345849B2 (en) 2016-07-20 2022-05-31 3M Innovative Properties Company Stabilizing styrenic polymer for quantum dots
WO2018051269A1 (en) 2016-09-19 2018-03-22 3M Innovative Properties Company Fluorescent nanoparticles stabilized with a functional aminosilicone
US20200115630A1 (en) 2017-03-14 2020-04-16 3M Innovative Properties Company Additive stabilized composite nanoparticles
KR101828214B1 (en) * 2017-07-18 2018-02-09 성균관대학교산학협력단 Inorganic nanoparticle structure, film, optical member, light-emitting device and quantum dot display apparatus having the same
US11608394B2 (en) 2018-02-06 2023-03-21 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Nanoparticles and formulations for printing
US11364479B2 (en) * 2018-03-16 2022-06-21 Exxonmobil Research And Engineering Company Ligand-exchanged zeolite imidazolate frameworks
JP7434181B2 (en) * 2018-05-03 2024-02-20 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング cross-linked ligand
EP3818130B1 (en) * 2018-07-05 2022-12-07 Merck Patent GmbH Composition comprising semiconducting light emitting nanoparticles
CN113120952B (en) * 2019-12-30 2022-11-29 Tcl科技集团股份有限公司 Zinc sulfide nano material and preparation method thereof, zinc sulfide thin film and quantum dot light-emitting diode
KR102399434B1 (en) * 2020-11-18 2022-05-19 덕산네오룩스 주식회사 Semiconductor nanoparticle-ligand composite, manufacturing method of thereof, photosensitive resin composition, optical film, electroluminescent diode and electronic device
KR102399431B1 (en) * 2020-11-18 2022-05-20 덕산네오룩스 주식회사 Semiconductor nanoparticle-ligand composite, photosensitive resin composition, optical film, electroluminescent diode and electronic device
US20240008304A1 (en) * 2020-11-18 2024-01-04 Duk San Neolux Co., Ltd. Semiconductor-nanoparticle-ligand complex, preparation method therefor, photosensitive resin composition, optical film, electroluminescent diode and electronic device
JP7355724B2 (en) 2020-12-07 2023-10-03 信越化学工業株式会社 Quantum dot surface treatment method and surface treatment device
KR102367520B1 (en) * 2021-07-15 2022-02-24 덕산네오룩스 주식회사 Semiconductor nanoparticle-ligand composite, manufacturing method of thereof, photosensitive resin composition, optical film, electroluminescent diode and electronic device

Family Cites Families (61)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5505928A (en) 1991-11-22 1996-04-09 The Regents Of University Of California Preparation of III-V semiconductor nanocrystals
US5262357A (en) 1991-11-22 1993-11-16 The Regents Of The University Of California Low temperature thin films formed from nanocrystal precursors
EP0613585A4 (en) 1991-11-22 1995-06-21 Univ California Semiconductor nanocrystals covalently bound to solid inorganic surfaces using self-assembled monolayers.
US6136222A (en) * 1991-12-11 2000-10-24 Bend Research, Inc. Liquid absorbent solutions for separating nitrogen from natural gas
US5674698A (en) 1992-09-14 1997-10-07 Sri International Up-converting reporters for biological and other assays using laser excitation techniques
US6048616A (en) 1993-04-21 2000-04-11 Philips Electronics N.A. Corp. Encapsulated quantum sized doped semiconductor particles and method of manufacturing same
US5537000A (en) 1994-04-29 1996-07-16 The Regents, University Of California Electroluminescent devices formed using semiconductor nanocrystals as an electron transport media and method of making such electroluminescent devices
US5677545A (en) 1994-09-12 1997-10-14 Motorola Organic light emitting diodes with molecular alignment and method of fabrication
US5985353A (en) 1994-12-01 1999-11-16 University Of Massachusetts Lowell Biomolecular synthesis of quantum dot composites
US5585640A (en) 1995-01-11 1996-12-17 Huston; Alan L. Glass matrix doped with activated luminescent nanocrystalline particles
GB9518910D0 (en) 1995-09-15 1995-11-15 Imperial College Process
US5876480A (en) 1996-02-20 1999-03-02 The United States Of America As Represented By The Secretary Of The Navy Synthesis of unagglomerated metal nano-particles at membrane interfaces
EP1818417B1 (en) 1996-07-29 2014-02-12 Nanosphere, Inc. Nanoparticles having oligonucleotides attached thereto and uses therefor
US6103868A (en) 1996-12-27 2000-08-15 The Regents Of The University Of California Organically-functionalized monodisperse nanocrystals of metals
US5939021A (en) 1997-01-23 1999-08-17 Hansen; W. Peter Homogeneous binding assay
AUPP004497A0 (en) 1997-10-28 1997-11-20 University Of Melbourne, The Stabilized particles
US6322901B1 (en) 1997-11-13 2001-11-27 Massachusetts Institute Of Technology Highly luminescent color-selective nano-crystalline materials
US6607829B1 (en) 1997-11-13 2003-08-19 Massachusetts Institute Of Technology Tellurium-containing nanocrystalline materials
US5985173A (en) 1997-11-18 1999-11-16 Gray; Henry F. Phosphors having a semiconductor host surrounded by a shell
US5990479A (en) 1997-11-25 1999-11-23 Regents Of The University Of California Organo Luminescent semiconductor nanocrystal probes for biological applications and process for making and using such probes
US6139585A (en) 1998-03-11 2000-10-31 Depuy Orthopaedics, Inc. Bioactive ceramic coating and method
US6501091B1 (en) 1998-04-01 2002-12-31 Massachusetts Institute Of Technology Quantum dot white and colored light emitting diodes
US6864626B1 (en) 1998-06-03 2005-03-08 The Regents Of The University Of California Electronic displays using optically pumped luminescent semiconductor nanocrystals
US6337117B1 (en) 1998-07-01 2002-01-08 Mitsubishi Chemical Corporation Optical memory device
US6294401B1 (en) 1998-08-19 2001-09-25 Massachusetts Institute Of Technology Nanoparticle-based electrical, chemical, and mechanical structures and methods of making same
US6214729B1 (en) * 1998-09-01 2001-04-10 Micron Technology, Inc. Metal complexes with chelating C-, N-donor ligands for forming metal-containing films
US6326144B1 (en) 1998-09-18 2001-12-04 Massachusetts Institute Of Technology Biological applications of quantum dots
US6306610B1 (en) * 1998-09-18 2001-10-23 Massachusetts Institute Of Technology Biological applications of quantum dots
JP4404489B2 (en) * 1998-09-18 2010-01-27 マサチューセッツ インスティテュート オブ テクノロジー Water-soluble fluorescent semiconductor nanocrystal
US6617583B1 (en) * 1998-09-18 2003-09-09 Massachusetts Institute Of Technology Inventory control
US6251303B1 (en) * 1998-09-18 2001-06-26 Massachusetts Institute Of Technology Water-soluble fluorescent nanocrystals
JP2000104058A (en) 1998-09-28 2000-04-11 Sony Corp Production of luminescent material
US6114038A (en) 1998-11-10 2000-09-05 Biocrystal Ltd. Functionalized nanocrystals and their use in detection systems
AU1911700A (en) 1998-11-10 2000-05-29 Biocrystal Limited Functionalized nanocrystals as visual tissue-specific imaging agents, and methods for fluorescence imaging
WO2000027365A1 (en) 1998-11-10 2000-05-18 Biocrystal Limited Functionalized nanocrystals and their use in detection systems
WO2000028089A1 (en) 1998-11-10 2000-05-18 Biocrystal Limited Functionalized nanocrystals and their use in labeling for strand synthesis or sequence determination
US6261779B1 (en) 1998-11-10 2001-07-17 Bio-Pixels Ltd. Nanocrystals having polynucleotide strands and their use to form dendrimers in a signal amplification system
WO2000028598A1 (en) 1998-11-10 2000-05-18 Biocrystal Limited Methods for identification and verification
DE60128458T2 (en) * 2000-03-20 2008-01-10 Massachusetts Institute Of Technology, Cambridge INORGANIC PARTICLE CONJUGATES
US6797412B1 (en) 2000-04-11 2004-09-28 University Of Connecticut Full color display structures using pseudomorphic cladded quantum dot nanophosphor thin films
JP2002020740A (en) * 2000-05-01 2002-01-23 Mitsubishi Chemicals Corp Semiconductive crystal ultrafine particle having ligand with hyperbranched structure
JP2002121549A (en) * 2000-06-26 2002-04-26 Mitsubishi Chemicals Corp Ultrafine semiconductor particle
JP3835135B2 (en) * 2000-07-27 2006-10-18 三菱化学株式会社 Semiconductor ultrafine particles formed by bonding amino groups
JP2002105090A (en) * 2000-09-27 2002-04-10 Mitsubishi Chemicals Corp Reactive phosphine oxides and semiconductor ultrafine particle having the same as ligand
JP2004510678A (en) 2000-10-04 2004-04-08 ザ　ボード　オブ　トラスティーズ　オブ　ザ　ユニバーシティ　オブ　アーカンソー Synthesis of colloidal nanocrystals
US6576291B2 (en) 2000-12-08 2003-06-10 Massachusetts Institute Of Technology Preparation of nanocrystallites
US6846565B2 (en) 2001-07-02 2005-01-25 Board Of Regents, The University Of Texas System Light-emitting nanoparticles and method of making same
WO2003092043A2 (en) 2001-07-20 2003-11-06 Quantum Dot Corporation Luminescent nanoparticles and methods for their preparation
EP1430549A2 (en) 2001-09-04 2004-06-23 Koninklijke Philips Electronics N.V. Electroluminescent device comprising quantum dots
US7205048B2 (en) 2001-09-17 2007-04-17 Invitrogen Corporation Functionalized fluorescent nanocrystal compositions and methods of making
US6955855B2 (en) 2001-09-17 2005-10-18 Biocrystal, Ltd. Nanocrystals
ATE431567T1 (en) * 2001-09-17 2009-05-15 Massachusetts Inst Technology SEMICONDUCTOR NANOCRYSTAL COMPOSITE
CA2474494A1 (en) * 2002-01-25 2003-08-07 Savvas E. Hadjikyriacou Photovoltaic cell components and materials
JP2003286292A (en) * 2002-01-28 2003-10-10 Mitsubishi Chemicals Corp Semiconductor ultrafine particle and filmy molded product containing the same
AU2003213381A1 (en) * 2002-03-15 2003-09-29 Fujitsu Limited Multidentate ligand, multi-nucleus metal complex, metal complex chain, metal complex integrated structure, and preparation method thereof
JP2006513458A (en) 2002-08-02 2006-04-20 ウルトラドッツ・インコーポレイテッド Quantum dots, nanocomposites with quantum dots, optical devices with quantum dots, and related manufacturing methods
JP2006502232A (en) * 2002-08-15 2006-01-19 モウンギ ジー． バウエンディ Stabilized semiconductor nanocrystals
AU2003298998A1 (en) * 2002-09-05 2004-04-08 Nanosys, Inc. Oriented nanostructures and methods of preparing
US20040265622A1 (en) 2003-06-24 2004-12-30 Eastman Kodak Company Light emitting display
US20060088713A1 (en) 2004-05-05 2006-04-27 Dykstra Tieneke E Surface modification of nanocrystals using multidentate polymer ligands
US7229690B2 (en) * 2004-07-26 2007-06-12 Massachusetts Institute Of Technology Microspheres including nanoparticles

Also Published As

Publication number Publication date
JP2011006412A (en) 2011-01-13
US7160613B2 (en) 2007-01-09
JP5356318B2 (en) 2013-12-04
WO2004042784A8 (en) 2004-07-15
US20100102277A1 (en) 2010-04-29
EP1576655A2 (en) 2005-09-21
WO2004042784A2 (en) 2004-05-21
US7601424B2 (en) 2009-10-13
AU2003301769A8 (en) 2009-05-07
EP1576655B1 (en) 2014-05-21
US20040091710A1 (en) 2004-05-13
US20070160838A1 (en) 2007-07-12
WO2004042784A3 (en) 2009-04-09
AU2003301769A1 (en) 2004-06-07
US8481162B2 (en) 2013-07-09
JP2006502232A (en) 2006-01-19
EP1576655A4 (en) 2010-05-05
CA2502669C (en) 2012-10-23

Similar Documents

Publication Publication Date Title
CA2502669A1 (en) Stabilized semiconductor nanocrystals
CA2403620A1 (en) Inorganic chromophore bioconjugates
CA2344478A1 (en) Biological applications of semiconductor nanocrystals
US10181565B2 (en) Quantum dots composite particles and their preparation method, photoelectric elements and photoelectric equipments
JP2006508012A5 (en)
CA2344479A1 (en) Water-soluble fluorescent semiconductor nanocrystals
ATE261892T1 (en) DEVICE FOR MONITORING A CONVEYOR SYSTEM
DK165221C (en) COATED TRANSPLANTS AND PROCEDURES FOR COATING THESE
DK1070255T3 (en) Method for detecting the complex of IGFBP-3 with IGF and / or ALS
WO2000023573A3 (en) Cd20-specific redirected t cells and their use in cellular immunotherapy of cd20+ malignancies
CA2344145A1 (en) Inventory control
NO20021055D0 (en) Insulating glass with a structural primary sealing system
WO2007068313A3 (en) Targeting and tracing of antigens in living cells
CN104518072B (en) Light emitting diode
WO2001025438A3 (en) Ifn-alpha homologues
TW358077B (en) Conveyor system and seal therefor
WO2002070793A1 (en) Ii-vi group or iii-v group based single crystal ferromagnetic compound and method for adjusting its ferromagnetic characteristics
ATE396213T1 (en) METHOD FOR LAMINATION USING SPECIAL CROSSLINKERS WITH CARBODIIMIDE GROUPS
DE60042527D1 (en) METHOD FOR FORMING A PEPTIDE RECEPTOR COMPLEX WITH ZSIG33 POLYPEPTIDES.
KR101507424B1 (en) sealing for cell phone using adsorption
US3874037A (en) Pressure sealing slide fastener
WO2004018418A3 (en) Hydrophilic chemiluminescent acridinium labeling reagents
EP0270321A3 (en) Monoclonal antibodies effective in promoting growth
ES2039192B1 (en) PREPARATION PROCEDURES FOR SUBSTITUTED PIRIDONE AMINO ACID AZETIDINYL DERIVATIVES.
CN217397536U (en) High-temperature-resistant adhesive conveying belt

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20230815