WO2014035159A1 - Point quantique électroluminescent à lumière blanche - Google Patents

Point quantique électroluminescent à lumière blanche Download PDF

Info

Publication number
WO2014035159A1
WO2014035159A1 PCT/KR2013/007772 KR2013007772W WO2014035159A1 WO 2014035159 A1 WO2014035159 A1 WO 2014035159A1 KR 2013007772 W KR2013007772 W KR 2013007772W WO 2014035159 A1 WO2014035159 A1 WO 2014035159A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
light emitting
quantum dot
white light
emitting
Prior art date
Application number
PCT/KR2013/007772
Other languages
English (en)
Korean (ko)
Inventor
이종호
김근태
안현철
Original Assignee
주식회사 동진쎄미켐
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 주식회사 동진쎄미켐 filed Critical 주식회사 동진쎄미켐
Priority to JP2015529678A priority Critical patent/JP6396297B2/ja
Priority to CN201380045599.4A priority patent/CN104603231A/zh
Priority claimed from KR1020130102868A external-priority patent/KR102243668B1/ko
Publication of WO2014035159A1 publication Critical patent/WO2014035159A1/fr

Links

Images

Classifications

    • 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
    • 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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/002—Osmium 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033—Iridium 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046—Ruthenium 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0086—Platinum 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • 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
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
    • Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps

Definitions

  • the present invention relates to a white light emitting quantum dot, and more particularly, to a white light emitting quantum dot capable of white light emission as one quantum dot alone and a method of manufacturing the same.
  • Quantum Dot is a nano-scale semiconductor material that exhibits a quantum confinement effect.
  • a quantum dot receives light from an excitation source and reaches an energy excited state, the corresponding energy bandgap is itself. To release energy.
  • the electrical and optical characteristics can be adjusted so that the light emission wavelength can be adjusted only by controlling the size of the quantum dot, and because it can exhibit characteristics such as excellent color purity and high luminous efficiency, It can be applied to various devices such as photoelectric change devices.
  • a quantum dot as a light emitting device that has been studied in the past has been disclosed for emitting only a wavelength of one color gamut, such as US Pat. No. 6,501,109 and WO2012 / 013272, but it was impossible to emit white light with only one quantum dot, and to realize white light.
  • In order to provide a separate filter layer there is a difficulty in changing the wavelength of the light emitted, and thus many quantum dots have not been reported for quantum dots emitting white light by themselves, despite many necessities.
  • the present invention is capable of providing white light by itself, and to provide a white light emitting quantum dot, a manufacturing method thereof and a light emitting device including the same that can exhibit excellent color purity, high stability and high luminous efficiency.
  • the purpose is capable of providing white light by itself, and to provide a white light emitting quantum dot, a manufacturing method thereof and a light emitting device including the same that can exhibit excellent color purity, high stability and high luminous efficiency.
  • a quantum dot comprising a structure of the core / shell and a ligand attached to the surface of the shell
  • the ligand comprises a light emitting group
  • the light emitting group of the core / shell structure and the ligand provides a white light emitting quantum dot characterized in that the light emits white light as a whole by emitting a color complementary to each other.
  • the structure of the core / shell may emit light in the region of 400 to less than 500 nm or light in the region of 500 to 800 nm,
  • the light emitting group When the structure of the core / shell emits light in the region of 400 to less than 500 nm, the light emitting group emits light in the region of 500 to 800 nm and the structure of the core / shell emits light in the region of 500 to 800 nm.
  • the light emitting group may be a quantum dot that emits white light by emitting light in an area of 400 or more and less than 500 nm.
  • the present invention provides a method for producing a white light emitting quantum dot comprising the step of adding a ligand containing a light emitting group to a solution in which the structure of the core / shell dispersed.
  • the present invention provides a light emitting device comprising the white light emitting quantum dots as a light emitting material.
  • the present invention provides a method of manufacturing a light emitting device comprising the step of forming a light emitting layer with the white light emitting quantum dots.
  • the white light emitting quantum dots according to the present invention can emit white light by itself without providing a separate filter layer, the white light emitting quantum dots have a simple structure when applied to the light emitting device and have excellent color purity, high stability and high luminous efficiency compared to the conventional light emitting device. can do.
  • FIG. 1 shows a schematic diagram of a white light emitting quantum dot according to an embodiment of the present invention.
  • Figure 2 shows a schematic diagram of a white light emitting quantum dot according to another embodiment of the present invention.
  • FIG. 3 is a schematic diagram of CdSe / ZnS synthesis used in a white light emitting quantum dot according to an embodiment of the present invention.
  • FIG. 4 is a schematic diagram showing the synthesis of white light emitting quantum dots according to an exemplary embodiment of the present invention.
  • 5 is an FT-IR spectra of a white light emitting quantum dot according to an embodiment of the present invention.
  • UV absorption and PL spectra of a white light emitting quantum dot according to an embodiment of the present invention.
  • FIG. 7 is a graph illustrating device light emission efficiency of a white light emitting quantum dot according to an exemplary embodiment of the present invention.
  • FIG. 8 illustrates an emission spectrum of a white light emitting quantum dot according to an embodiment of the present invention.
  • the white light emitting quantum dot of the present invention is a quantum dot including a core / shell structure and a ligand attached to the surface of the shell, wherein the ligand includes a light emitting group, and the light emitting group of the core / shell structure and the ligand is complementary to each other.
  • the light emission wavelength of the ligand containing the light emitting group and the structure of the core / shell having a complementary color relationship can be arbitrarily adjusted.
  • the structure of the core / shell emits light in the region of 400 nm to less than 500 nm, or Can emit light in the range of 500 to 800 nm
  • the light emitting group When the structure of the core / shell emits light in the region of 400 to less than 500 nm, the light emitting group emits light in the region of 500 to 800 nm and the structure of the core / shell emits light in the region of 500 to 800 nm. In this case, the light emitting group emits light in an area of 400 or more and less than 500 nm so that the quantum dots emit white light as a whole.
  • the ligand includes a light emitting group and a linking group connecting the shell and the light emitting group, and may include a spacer between the linking group and the light emitting group, if necessary.
  • Structural formula 1 shows a schematic diagram of a white light emitting quantum dot according to an embodiment of the present invention.
  • A represents a light emitting group
  • L represents a spacer
  • X represents a linking group
  • a core / shell structure may be a known core / shell structure.
  • the core / shell structure described in Korean Patent Publication No. 2010-35466 may be used.
  • the core / shell structure may comprise a) a first element selected from group 2, 12, 13 and 14 and a second element selected from group 16; b) a first element selected from group 13 and a second element selected from group 15; And c) Group 14 elements; one material selected from the group consisting of, or these forms a structure of the core / shell, for example, MgO, MgS, MgSe, MgTe, CaO, CaS, CaSe, CaTe , SrO, SrS, SrSe, SrTe, BaO, BaS, BaSe, BaTE, ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, HgO, HgS
  • the average diameter of the structure of the core / shell can be arbitrarily adjusted in consideration of the complementary color relationship, it can be used 1-12 nm.
  • the structure of the core / shell which emits light in the range of 500 to 800 nm or less has a diameter of 5-12 nm
  • the structure of the core / shell which emits light in the region of 400 or more and less than 500 nm may have a diameter of 1-3 nm.
  • the structure of the core / shell emits light in the region of 500 or more and 800 nm or less. It is good to use that.
  • a light emitting group capable of emitting a color that is complementary to the light emitting color of the core / shell structure contained in the ligand and emits white light as a whole is applied.
  • the light emitting group when the structure of the core / shell emits light in an area of 400 or more and less than 500 nm, the light emitting group emits light in an area of 500 or more and less than 800 nm and the structure of the core / shell is in an area of more than 500 and less than 800 nm.
  • the light emitting group uses a group that emits light in a range of 400 to less than 500 nm.
  • the light emitting group may be a known light emitting group, and for example, a fluorescent or phosphorescent light emitting group may be used. More specifically, the group for emitting light in the region of 400 or more and less than 500 nm may be one of the following FL1 to FL38, or PL1 to PL59, and the group for emitting the light in the region of 500 or more and less than 800 nm may be one of the following FL1 to FL38, Or PL1 to PL59.
  • R1 to R16 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1 -C 40 alkyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2 -C 40 alkenyl group; C 1 ⁇ C 40 Alkoxy group; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 Heterocycloalkyl group; C 6 -C 40 aryl group; C 3 ⁇ C 40 heteroaryl group; An aralkyl group of C 3 ⁇ C 40; C 3 -C 40 aryloxy group; C 3 -C 40 arylthio group or Si.
  • R 1 to R 16 may combine with each
  • the light emitting group is a group for emitting light in the region of 400 to less than 500 nm.
  • the linking group in the white light emitting quantum dot of the present invention is not particularly limited as long as the linking group is attached to the shell and can be connected to the light emitting group or the spacer, for example, a thiol group, a carboxyl group, an amine group, or a phosphine group. And at least one group selected from the group consisting of phosphide groups can be used.
  • the linking group is a thiol group.
  • the white light emitting quantum dot of the present invention may further include a spacer between the light emitting group and the connecting group.
  • the spacers may increase the number of light emitting groups that may be attached to the core / shell structure, and may facilitate dispersion of a ligand including a light emitting material into a solvent when preparing white light emitting quantum dots.
  • the spacer may be substituted or unsubstituted saturated or unsaturated C 1 ⁇ C 30 alkyl group, C 3 ⁇ C 40 cycloalkyl group, Si 1 ⁇ Si 30 silane may be used, but is not limited thereto.
  • the present invention includes all of the light emitting group, the spacer and the linking group, for example, may have a structure as follows.
  • the H portion of -SH is a portion that bonds with the core / shell structure.
  • Structures suitable for emitting light in the region of 400 to less than 500 nm are:
  • the size of the whole white light-emitting quantum dot including the light emitting group in the ligand can be arbitrarily adjusted, preferably 5 to 30 nm, more preferably 10-20 nm.
  • the light emission intensity of the core / shell structure and the light emitting group can be arbitrarily adjusted.
  • the difference in the light emission intensity ratio of the core / shell structure and the light emitting group in the complementary color relationship is within 30%. Do. That is, when the emission intensity in the region of 400 to less than 500 nm is 1, the emission intensity of the region of 500 to 800 nm is preferably 0.7-1.3. When the intensity is 0.7 or less, the color purity is blue shifted.
  • Red shifting may make it difficult to emit white light.
  • the emission intensity in the region of 500 to 800 nm is 1, the emission intensity of the region of 400 to 500 nm is preferably 0.7-1.3.
  • the intensity is 0.7 or less, the color purity is red shifted. As a result, the quantum dot may be difficult to emit white light.
  • Structural formula 2 shows a schematic diagram of a white light emitting quantum dot according to a specific example of the present invention, and since the light emitting material emits light in an area of 400 to less than 500 nm, the core / shell structure emits light in an area of 500 to 800 nm or less.
  • the core may use CdSe and the shell may use ZnS.
  • the white light emitting quantum dots according to the present invention may be prepared by adding a ligand containing a light emitting group to a solution in which the structure of the core / shell is dispersed, followed by stirring.
  • the preparation of the structure of the core / shell in the above can be used well known methods, of course, can be specifically followed the synthesis method described in FIG.
  • the ligand may be prepared by binding a linking group to the light emitting group or by including a spacer between the light emitting group and the linking group through the procedures of Schemes 1 and 2 below.
  • the stirring may be performed at room temperature to 100 °C for 0.1 to 100 hours.
  • the present invention also provides a light emitting device (QLED) using the white light emitting quantum dots and a method of manufacturing the same.
  • the light emitting device may be applied to other known technologies except for the light emitting layer formed by using the white light emitting quantum dots according to the present invention.
  • the light emitting device may be configured such that a substrate-a cathode-a light emitting layer formed of a white light emitting quantum dot according to the present invention-an anode may be sequentially formed, and an electron transport layer is further formed between the cathode and the light emitting layer. It is also possible to further form a hole transport layer between the light emitting layer and the anode. In addition, if necessary, a hole suppression layer may be further included between the electron transport layer and the light emitting layer, and a buffer layer may be formed between each layer.
  • a light emitting device (QLED) using a white light emitting quantum dot may be formed by a conventional manufacturing method, and the thickness of each organic film including the light emitting layer may be manufactured to be 30 to 100 nm.
  • a buffer layer may be formed between each layer, and as a material of such a buffer layer, Materials may be used, for example copper phthalocyanine, polythiophene, polyaniline, polyacetylene, polypyrrole, polyphenylene vinylene, or Derivatives thereof may be used, but are not limited thereto.
  • the material of the hole transport layer a material commonly used may be used.
  • polytriphenylamine may be used, but is not limited thereto.
  • the material of the electron transport layer a material commonly used may be used, for example, polyoxadiazole may be used, but is not limited thereto.
  • a material commonly used as the material of the hole suppression layer may be used, for example, LiF, BaF 2 or MgF 2 may be used, but is not limited thereto.
  • the light emitting device of the present invention may be manufactured according to the method described in FIG.
  • the light emitting device according to the present invention manufactured as described above can emit white light by itself without having a separate filter layer, so that the light emitting layer is formed of white light emitting quantum dots, so that the structure is simple and high in stability, compared to the conventional light emitting device. It has excellent color purity and high luminous efficiency.
  • Synthesis Example 3 was repeated in Synthesis Example 1, except that 1,5-dibrompentane was used instead of 1.10-dibromodeken in Synthesis Example 2, and Pale yellow DJ-A-2 was synthesized.
  • Synthesis Example 1 the procedure of Synthesis Example 3 was repeated, except that 9- (4-bromopheneyl) -10-phenylanthracene was used instead of 9-bromo-10-phenyl anthracene in Synthesis Example 1, and white solid DJ-A-3 was used. Synthesized.
  • Synthesis Example 1 the procedure of Synthesis Example 3 was repeated, except that 9-brom-10- (2-napthyl) anthracene was used instead of 9-bromo-10-phenyl anthracene in Synthesis Example 1, yellow solid DJ-A-5 was synthesized.
  • the reaction temperature was maintained at 310 °C for 10 minutes and then cooled to room temperature.
  • the resulting quantum dots were purified with 20 mL of chloroform and excess acetone (at least 3 times). Quantum dots were redispersed in chloroform or hexane at a concentration of 5.0 mg / mL.
  • ZnO nanoparticles are used as the electron transport layer
  • ZnO nanoparticle synthesis was used the following method. That is, 30 mL of zinc acetate dimethyl sulfoxide (DMSO, 0.5 M) was added, and tetramethylammonium hydride (TMAH, 0.55 M) mixture was stirred in ethanol for 1 hour. It was then centrifuged and washed with ethanol and excess acetone mixture. The synthesized ZnO nanoparticles were dispersed in ethanol at a concentration of 30 mg / mL and used as an electron transport layer material for the LED manufacturing apparatus.
  • DMSO zinc acetate dimethyl sulfoxide
  • TMAH tetramethylammonium hydride
  • white light-emitting quantum dots were synthesized. That is, a CdSe / ZnS solution (0.2 ml, 5 mg / ml in hexane) was prepared using the quantum dots prepared in Synthesis Example 9, and a light emitting material (0.5 ml, 3 mM in hexane) prepared in Synthesis Example 3 was added thereto. Stirred at room temperature for 30 minutes. Methanol was added to the reaction flask to solidify and centrifuged to produce white light-emitting quantum dots. Ligand exchange results were confirmed by IR DATA, UV absorption and PL spectra.
  • 5 is an FT-IR spectra of the prepared white light emitting quantum dots, (a) shows Synthesis Example 3 (DJ-A-1), and (b) shows Example 1 (DJ-A-1 + CdSe / ZnS). It is measured. 6 is UV absorption and PL spectra, (a) shows Synthesis Example 8 (QDs), (b) shows Synthesis Example 3 and (c) Example 1;
  • QD-LED was fabricated on an indium tin oxide coated glass (ITO / glass) substrate (sheet resistance ⁇ 10 ⁇ / ⁇ ).
  • ITO / glass indium tin oxide coated glass
  • the ITO glass was washed with acetone and isopropyl alcohol using ultrasonic waves for 1 minute and plasma treated with argon / oxygen for 1 minute.
  • poly (3,4-ethylene dioxythiophene): poly (styrene sulfonate) (PEDOT: PSS, Baytron P AI 4083) was diluted with isopropyl alcohol in a 9: 1 volume ratio and spin-coated at 4,000 rpm for 30 seconds.
  • PEDOT PSS coated ITO glass was baked in a hot plate at 120 ° C. for 10 minutes in air.
  • the coated substrate was spin-coated with polyvinylcarbazole (PVK, 0.01 g / mL of chlorobenzene) at 3,000 rpm for 30 seconds in a glove box filled with N 2 , followed by baking the substrate at 180 ° C. for 30 minutes, Used as a hole transport layer.
  • PVK polyvinylcarbazole
  • the white light emitting quantum dot solution prepared in Example 1 was spin coated for 1,500 rpm for 20 seconds.
  • the ZnO nanoparticle (30 mg / mL) solution was spin coated at 1,500 rpm for 30 seconds, and the substrate was baked at 150 ° C. for 30 minutes. Finally, the multilayer thin film substrate was placed in a high vacuum deposition chamber (background pressure ⁇ 5 ⁇ 10 ⁇ 6 torr) and an aluminum cathode (100 nm thick) was deposited.
  • Example 2 instead of the white light emitting quantum dots, Orange light emitting quantum dots of Synthesis Example 9 was used as the light emitting layer.
  • Example 2 DJ-A-1 of Synthesis Example 3 was used as a light emitting layer instead of the white light emitting quantum dots.
  • Example 2 The IVL characteristics and EL spectra of the electroluminescent (EL) devices of Example 2 and Comparative Examples 1 and 2 prepared above were confirmed.
  • the maximum light emission intensity is 2,000 cd / m 2, and the light emission efficiency of each device is shown in Table 1 and Graph 7 below.
  • (A) of FIG. 7 shows current density and luminance versus driving voltage, and (b) shows luminance power efficiency versus luminance.
  • the white light emitting quantum dots according to the present invention can emit white light by itself without providing a separate filter layer, the white light emitting quantum dots have a simple structure when applied to the light emitting device and have excellent color purity, high stability and high luminous efficiency compared to the conventional light emitting device. can do.

Abstract

La présente invention concerne un point quantique électroluminescent à lumière blanche. Plus particulièrement, la présente invention concerne un point quantique et son procédé de fabrication, le point quantique comprenant une structure cœur/écorce et un ligand fixé à la surface de l'écorce. Le ligand comprend un groupe électroluminescent. La structure cœur/écorce et le groupe électroluminescent du ligand peuvent émettre une lumière ayant des couleurs complémentaires, émettant ainsi globalement une lumière blanche. Le point quantique électroluminescent à lumière blanche selon la présente invention peut émettre seul de la lumière blanche sans utiliser de couche filtrante séparée. De ce fait, le dispositif électroluminescent qui adopte le point quantique électroluminescent à lumière blanche de la présente invention peut avoir une structure simple tout en présentant d'excellentes propriétés de pureté des couleurs, une stabilité élevée, et une efficacité élevée de l'électroluminescence comparativement à des dispositifs électroluminescents classiques.
PCT/KR2013/007772 2012-08-29 2013-08-29 Point quantique électroluminescent à lumière blanche WO2014035159A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2015529678A JP6396297B2 (ja) 2012-08-29 2013-08-29 白色発光量子ドット
CN201380045599.4A CN104603231A (zh) 2012-08-29 2013-08-29 发白光量子点

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20120095010 2012-08-29
KR10-2012-0095010 2012-08-29
KR1020130102868A KR102243668B1 (ko) 2012-08-29 2013-08-29 백색 발광 양자점
KR10-2013-0102868 2013-08-29

Publications (1)

Publication Number Publication Date
WO2014035159A1 true WO2014035159A1 (fr) 2014-03-06

Family

ID=50183892

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2013/007772 WO2014035159A1 (fr) 2012-08-29 2013-08-29 Point quantique électroluminescent à lumière blanche

Country Status (1)

Country Link
WO (1) WO2014035159A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9312500B2 (en) 2012-08-31 2016-04-12 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
CN106164214A (zh) * 2014-02-24 2016-11-23 中央科学研究中心 具有聚集诱导型发射的发光杂化纳米材料
CN106957650A (zh) * 2017-03-22 2017-07-18 深圳市华星光电技术有限公司 一种修饰量子点的制备方法及修饰量子点薄膜
US9902687B2 (en) 2014-09-19 2018-02-27 Idemitsu Kosan Co., Ltd. Compound
US9947879B2 (en) 2013-03-15 2018-04-17 Idemitsu Kosan Co., Ltd. Anthracene derivative and organic electroluminescence element using same
CN111933673A (zh) * 2020-08-17 2020-11-13 京东方科技集团股份有限公司 显示面板及其制作方法、显示装置

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
AHN, JIN H. ET AL.: "White organic light-emitting devices incorporating nanoparticles of II VI semiconductors.", NANOTECHNOLOGY., vol. 18, no. 335202, 2007, pages 1 - 5 *
KRZYSZTOF, DANEL ET AL.: "Blue-emitting anthracenes with end-capping diarylamines.", CHEMISTRY OF MATERIALS., vol. 14, 2002, pages 3860 - 3865 *
PARK, JONG HYEOK ET AL.: "White emission from polymer/quantum dot ternary nanocomposites by incomplete energy transfer.", NANOTECHNOLOGY., vol. 15, 2004, pages 1217 - 1220 *
PARK, SANGHYUK ET AL.: "A White-light-emitting molecule: frustrated energy transfer between constituent emitting centers.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 131, 2009, pages 14043 - 14049 *
ROGACH, ANDREY L. ET AL.: "Light-emitting diodes with semiconductor nanocrystals.", ANGEWANDTE CHEMIE INTERNATIONAL EDITION., vol. 47, 2008, pages 6538 - 6549 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9312500B2 (en) 2012-08-31 2016-04-12 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
US9947879B2 (en) 2013-03-15 2018-04-17 Idemitsu Kosan Co., Ltd. Anthracene derivative and organic electroluminescence element using same
CN106164214A (zh) * 2014-02-24 2016-11-23 中央科学研究中心 具有聚集诱导型发射的发光杂化纳米材料
US10519365B2 (en) 2014-02-24 2019-12-31 Centre National De La Recherche Scientifique Luminescent hybrid nanomaterials with aggregation induced emission
CN106164214B (zh) * 2014-02-24 2020-03-06 中央科学研究中心 具有聚集诱导型发射的发光杂化纳米材料
US9902687B2 (en) 2014-09-19 2018-02-27 Idemitsu Kosan Co., Ltd. Compound
US10118889B2 (en) 2014-09-19 2018-11-06 Idemitsu Kosan Co., Ltd. Compound
US10435350B2 (en) 2014-09-19 2019-10-08 Idemitsu Kosan Co., Ltd. Organic electroluminecence device
CN106957650A (zh) * 2017-03-22 2017-07-18 深圳市华星光电技术有限公司 一种修饰量子点的制备方法及修饰量子点薄膜
CN111933673A (zh) * 2020-08-17 2020-11-13 京东方科技集团股份有限公司 显示面板及其制作方法、显示装置

Similar Documents

Publication Publication Date Title
WO2014035159A1 (fr) Point quantique électroluminescent à lumière blanche
WO2012173370A2 (fr) Composés originaux et dispositif électronique organique utilisant ces composés
WO2020045924A1 (fr) Nouveau composé et diode électroluminescente organique utilisant ce composé
WO2013009079A1 (fr) Composé à base de triphénylène et diode électroluminescente organique l'utilisant
WO2013055132A2 (fr) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant et dispositif électronique correspondant
WO2010131855A2 (fr) Composé contenant un hétérocycle à 5 éléments, diode électroluminescente organique dans laquelle il est employé, et borne destinée à cette dernière
WO2011115378A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2010005266A2 (fr) Nouveau dérivé d'anthracène et dispositif électronique organique utilisant un tel dérivé
WO2010114266A2 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant
WO2011139125A2 (fr) Composé de phénanthrocarbazole, et dispositif électroluminescent organique utilisant ce composé
WO2010126234A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2011010842A2 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique associé
WO2011010843A1 (fr) Composés électroluminescents organiques innovants et dispositif électroluminescent organique les utilisant
WO2013109030A1 (fr) Dispositif électroluminescent organique comprenant les composés électroluminescents organiques
WO2010114256A2 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2011010839A1 (fr) Nouveau composé organique électroluminescent et dispositif organique électroluminescent utilisant ce dernier
WO2011108901A2 (fr) Composé de spiro-carbazole comprenant un squelette spiro, et élément électronique organique utilisant celui-ci et terminal de celui-ci
WO2010005268A2 (fr) Nouveau dérivé d'anthracène et dispositif organique électronique utilisant ledit dérivé
KR20140071256A (ko) 발광 양자점
WO2010114262A2 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant
WO2014084612A1 (fr) Nouveau composé et élément électronique organique l'utilisant
WO2010058946A2 (fr) Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés
WO2015068987A1 (fr) Nouveau composé organique, et élément électroluminescent organique et dispositif électronique comprenant ce composé
WO2010085087A2 (fr) Nouveaux dérivés de cycloalcène et dispositifs électroniques organiques utilisant ces dérivés de cycloalcène
KR102243668B1 (ko) 백색 발광 양자점

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13832538

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2015529678

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13832538

Country of ref document: EP

Kind code of ref document: A1