WO2022009930A1 - Matériau électroluminescent, encre électroluminescente, corps électroluminescent et dispositif électroluminescent - Google Patents

Matériau électroluminescent, encre électroluminescente, corps électroluminescent et dispositif électroluminescent Download PDF

Info

Publication number
WO2022009930A1
WO2022009930A1 PCT/JP2021/025663 JP2021025663W WO2022009930A1 WO 2022009930 A1 WO2022009930 A1 WO 2022009930A1 JP 2021025663 W JP2021025663 W JP 2021025663W WO 2022009930 A1 WO2022009930 A1 WO 2022009930A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
rare earth
hfa
tppo
light emitting
Prior art date
Application number
PCT/JP2021/025663
Other languages
English (en)
Japanese (ja)
Inventor
靖哉 長谷川
テン ツァン
裕一 北川
Original Assignee
国立大学法人北海道大学
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 国立大学法人北海道大学 filed Critical 国立大学法人北海道大学
Publication of WO2022009930A1 publication Critical patent/WO2022009930A1/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
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/50—Sympathetic, colour changing or similar inks
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials

Definitions

  • the present disclosure relates to light emitting materials, light emitting inks, light emitting bodies and light emitting devices.
  • Patent Document 1 Attempts have been made to immobilize a luminescent rare earth complex on a substrate containing silica or the like (for example, Patent Document 1 and Non-Patent Document 1).
  • Patent Document 1 discloses a method for obtaining a phosphor by surface-treating a fired product obtained by adding an aqueous solution of aluminum nitrate and an aqueous solution of europium nitrate to porous silica, mixing them, drying and firing them with a silane coupling agent. do. Although aluminum and europium are fixed on silica, it is not clear what kind of form they are, and it is considered that they adhere unevenly.
  • Non-Patent Documents 1 and 2 disclose europium complex-containing particles in which a bidentate ligand such as a phosphine oxide ligand or a bipyridine ligand is bonded to silica via one linker group.
  • a bidentate ligand such as a phosphine oxide ligand or a bipyridine ligand is bonded to silica via one linker group.
  • one aspect of the present disclosure provides a novel luminescent material containing a rare earth complex immobilized on a substrate and exhibiting high luminescence quantum efficiency.
  • One aspect of the present disclosure is a substrate containing at least one of a metal oxide or a metal sulfide, two or more linker groups attached to the substrate, and one phosphine oxide attached to each of the linker groups.
  • a luminescent material containing a phosphine oxide ligand having a group and a rare earth ion.
  • a rare earth complex is formed by one of the rare earth ions and two or more of the phosphine oxide ligands.
  • Another aspect of the present disclosure is to provide a luminescent ink comprising the luminescent material and a dispersion medium in which the luminescent material is dispersed.
  • Yet another aspect of the present disclosure is to provide a light emitting body containing the above light emitting material and a light emitting device including the light emitting body.
  • a novel luminescent material containing a rare earth complex immobilized on a substrate and exhibiting high luminescence quantum efficiency is provided.
  • An example of a luminescent material has a substrate containing at least one of a metal oxide or a metal sulfide, two or more linker groups attached to the substrate, and one phosphine oxide group attached to the linker group. Contains multiple phosphine oxide ligands and multiple rare earth ions. A rare earth complex is formed by one rare earth ion and two or more phosphine oxide ligands.
  • X represents a substrate
  • Ln (III) is Shows rare earth ions.
  • Ar 1 and Ar 2 each independently represent an aryl group which may have a substituent.
  • Z indicates an n-position ligand forming a coordinate bond with the rare earth ion Ln (III).
  • a rare earth complex is formed with one rare earth ion Ln (III), two phosphine oxide ligands, and 6 / n ligands Z.
  • the number of phosphine oxide groups attached to one linker group L is typically one.
  • the rare earth complex Although only one rare earth complex is shown in the formula (I), a large number of rare earth complexes are usually bonded to the base material X via the linker group L. According to the findings of the present inventors, by immobilizing the rare earth complex on the base material X via two or more linker groups, the rare earth complex is stably immobilized on the base material X, and the rare earth complex is stably immobilized on the base material X. It can emit light with a higher quantum yield compared to unfixed rare earth complexes.
  • the shape of the base material X is not particularly limited, and for example, the base material X may be a particle, a film, or a plate-like body.
  • the base material X is a particle
  • the light emitting material into which the rare earth complex is introduced is also usually in the form of particles.
  • the particulate luminescent material is expected to be applied as, for example, a luminescent ink or fluorescent particles used in the biomedical field.
  • the film as a base material may be, for example, a plastic film.
  • the plate-like body as the base material may be, for example, a glass plate.
  • the base material X When the base material X is a particle, its average particle size may be 1000 nm or less, 500 nm or less, or 100 nm or less, or 10 nm or more.
  • a particulate light-emitting material having nanoparticles having a nano-order particle size as a base material X tends to have good dispersibility with respect to various dispersion media.
  • the particle size of the light emitting material into which the rare earth complex is introduced may be 1000 nm or less, 500 nm or less, or 100 nm or less, or 10 nm or more.
  • Base material X contains metal oxides, metal sulfides, or both.
  • metal oxides include silicon dioxide (silica), zinc oxide, calcium oxide, titanium oxide, aluminum oxide, and indium tin oxide (ITO).
  • metal sulfides include zinc sulfide and cadmium sulfide.
  • the base material X may be a glass body (for example, silica glass, ITO glass, fluorine glass) or a crystal.
  • the total content of metal oxides and metal sulfides in the base material X is 50 to 100% by mass, 60 to 100% by mass, 70 to 100% by mass, 80 to 100% by mass, based on the mass of the base material X. Alternatively, it may be 90 to 100% by mass.
  • the linker group L has a functional group forming a bond with the metal oxide or metal sulfide of the base material X.
  • the functional group can be, for example, a residue of a hydrolyzable silyl group.
  • the linker group L may further have an arylene group bonded to a phosphine oxide group.
  • the linker group containing the residue of the hydrolyzable silyl group and the arylene group may be, for example, a portion of the group represented by the following formula (1) excluding X.
  • X represents a base material
  • R 1 represents a divalent organic group
  • R 2 represents an alkyl group having 1 to 5 or 1 to 3 carbon atoms
  • Ar 3 represents a phosphine oxide group.
  • the attached arylene group (for example, a phenylene group, a biphenylene group, a naphthylene group) is shown.
  • p represents an integer of 1 to 3 corresponding to the number of three oxygen atoms bonded to Si that are bonded to the base material X.
  • * Indicates the portion of the phosphine oxide group bonded to the phosphorus atom.
  • R 1 is usually an organic group derived from a synthetic pathway that induces a linker group.
  • R 1 may be a group containing an amide group, and an example of the linker group L in that case is represented by the following formula (1a).
  • R 3 in the formula (1a) represents an alkylene group.
  • the carbon number of the alkylene group as R 3 may be, for example, 1 or more or 2 or more, and may be 20 or less, 15 or less, or 10 or less.
  • Ar 1 and Ar 2 in the formula (I) each independently represent an aryl group which may have a substituent.
  • the aryl group as Ar 1 or Ar 2 can be a residue obtained by removing one hydrogen atom from an aromatic compound.
  • Specific examples of aryl groups include substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, or substituted or unsubstituted phenanthrene with one hydrogen atom removed. ..
  • Ar 1 and Ar 2 may be substituted or unsubstituted phenyl groups.
  • the substituent contained in the aryl group may be a halogen atom.
  • the rare earth ion constituting the rare earth complex introduced into the luminescent material is usually a trivalent rare earth ion.
  • Rare earth ions can be appropriately selected depending on the emission color and the like.
  • Rare earth ions include, for example, Eu (III) ion, Tb (III) ion, Gd (III) ion, Sm (III) ion, Yb (III) ion, Nd (III) ion, Er (III) ion, Y ( It can be at least one selected from the group consisting of III) ions, Dy (III) ions, Ce (III) ions, and Pr (III) ions. From the viewpoint of obtaining high emission intensity, the rare earth ion may be Eu (III) ion, Tb (III) ion, Gd (III) ion or a combination thereof.
  • the luminescent material exemplified as the formula (I) further has an n-position ligand Z other than the phosphine oxide ligand having a linker group L, which forms a coordinate bond with the rare earth complex.
  • the ligand Z may be a bidentate ligand, and examples thereof include a diketone ligand represented by the following formula (2).
  • the diketone ligand can contribute to further improvement of the emission intensity and the like of the rare earth complex by the photosensitizing action.
  • R 11 and R 12 represent an aliphatic group which may independently have a substituent or an aromatic group which may have a substituent
  • R 13 is a hydrogen atom. It indicates an aliphatic group which may have a substituent or an aromatic group which may have a substituent, and R 13 may be bonded to R 11 or R 12 to have a substituent. It may form a cyclic group. R 13 may be a deuterium atom.
  • R 11 , R 12 and R 13 may each independently be an alkyl group (eg, a methyl group, a tert-butyl group), an alkyl halide group, an aryl group or an aryl halide group.
  • the alkyl group and the halogenated alkyl group may have 1 to 10 carbon atoms.
  • the alkyl halide group as R 11 , R 12 or R 13 is a fluoroalkyl group having 1 to 5 carbon atoms (for example, trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluorobutyl group, perfluoropentyl). It may be a group).
  • the aryl group as R 11 , R 12 or R 13 may be a phenyl group, a naphthyl group, or a thienyl group, and these may be halogenated.
  • the cyclic group formed by binding R 13 to R 11 or R 12 may be a cyclic aliphatic group, an aromatic group, or a group consisting of a combination thereof, which may have a substituent.
  • the ligand Z may have optical activity.
  • the optically active ligand Z By introducing the optically active ligand Z into the light emitting material, the light emitting material can be imparted with circularly polarized light characteristics.
  • the optically active ligand Z may be, for example, a camphor derivative represented by the following formula (20) or an enantiomer thereof. The two enantiomers may be combined in any ratio.
  • R 21 is synonymous with R 11 in equation (2).
  • R 22 , R 23 and R 24 each represent a hydrocarbon group which may have a substituent independently, and R 25 , R 26 , R 27 and R 28 independently represent a hydrogen atom, a halogen atom, or a substituent, respectively. Indicates a hydrocarbon group which may have a group.
  • R 22 , R 23 and R 24 may be an alkyl group which may have a substituent and may have 1 to 5 carbon atoms. Specific examples of R 22 , R 23 and R 24 include a methyl group.
  • R 25 , R 26 , R 27 and R 28 may each be an independently substituted alkyl group and may have 1 to 5 carbon atoms.
  • R 25 , R 26 , R 27 and R 28 may be hydrogen atoms.
  • Specific examples of the camphor derivative represented by the formula (20) and its enantiomer include 3- (trifluoroacetyl) camphorate (tfc) and 3- (perfluorobutyryl)-( ⁇ ) -camphorate. Be done.
  • the luminescent material includes, for example, a linker group containing a functional group (for example, a hydrolyzable silyl group) forming a bond with the metal oxide or metal sulfide of the base material X, and a phosphine oxide ligand containing a phosphine oxide group. It can be obtained by a method including a step of binding the compound to the base material X and a step of forming a rare earth complex with a phosphine oxide ligand bonded to the base material X via a linker group and a rare earth ion.
  • a linker group containing a functional group for example, a hydrolyzable silyl group
  • the following formula (3) shows an example of a compound having a linker group containing a hydrolyzable silyl group and a phosphine oxide ligand that can be used in the production of a light emitting material.
  • R 1 , R 2 , Ar 1 , Ar 2 and Ar 3 in the formula (3) have the same meanings as described above.
  • the compound of the formula (3) includes, for example, a compound having a hydrolyzable silyl group and an amino group represented by the following formula (11), and a phosphine oxide group and a carboxyl group represented by the following formula (12). It can be obtained by reacting with a compound or a derivative thereof. Not limited to the reaction of an amino group and a carboxyl group as in the formulas (11) and (12), a compound containing a combination of functional groups capable of forming a chemical bond by the reaction can be arbitrarily applied.
  • An example of the luminescent ink can include a particulate luminescent material and a dispersion medium in which the luminescent material is dispersed.
  • a film of a light emitting body can be formed by a printing method using light emitting ink or the like.
  • the dispersion medium is not particularly limited, but may be, for example, methanol, ethanol, water, acetone, hexane, chloroform, dichloromethane, diethyl ether, ethyl acetate, benzene, toluene, or a combination thereof.
  • the luminescent ink may contain styrene, acrylic acid, methacrylic acid, acrylic acid derivatives, methacrylic acid derivatives (methyl methacrylate, ethyl methacrylate, etc.), or polymers (polystyrene, polymethyl methacrylate, etc.).
  • An example of a light emitting body includes a light emitting material according to the above-described embodiment.
  • This light emitting body can form various light emitting devices or security materials.
  • Examples of light emitting devices include micro LEDs, display devices such as traffic signs and illuminated signs, liquid crystal backlights, and lighting displays.
  • Eu (hfa) 3 (H 2 O) 2 was dehydrated by heating at 135 ° C. for 4 hours under a reduced pressure of 1 ⁇ 10 -3 mbar.
  • Dehydrated Eu (hfa) 3 (H 2 O) 2 (90 mg, 0.11 mmol) is placed in a Schlenk tube, dry ethanol (10 mL) is added under a nitrogen atmosphere, and then TPPO-Si (OEt) 3 (115 mL) is added. mg. 0.22 mmol) was added. The yellow solution formed was stirred at room temperature for 5 hours.
  • Silica nanoparticles Ammonia solution (28%, 9.5 mL), triethoxysilane (7.0 mL), and absolute ethanol (183 mL) were placed in a round bottom flask. The formed solution was stirred at 45 ° C. overnight to obtain a milky white dispersion containing silica nanoparticles. Silica nanoparticles were recovered by centrifugation at 4000 rpm and dispersed in absolute ethanol (185 mL) by ultrasonic method.
  • Luminescent material having an Eu complex immobilized on silica nanoparticles SiO 2- Eu (hfa) 3 [TPPO-Si (O) 3 ] 2 )
  • FIG. 1 is a transmission electron micrograph of unmodified silica nanoparticles
  • FIG. 2 shows transmission electrons of a particulate luminescent material (SiO 2- Eu (hfa) 3 [TPPO-Si (O) 3 ] 2 ). It is a micrograph.
  • FIG. 3 is an EDS spectrum of SiO 2- Eu (hfa) 3 [TPPO-Si (O) 3 ] 2.
  • FIG. 4 shows the FT- of TPPO-Si (OEt) 3 , Eu (hfa) 3 [TPPO-Si (OEt) 3 ] 2 , and SiO 2- Eu (hfa) 3 [TPPO-Si (O) 3 ] 2 . IR spectrum.
  • thermogravimetric analysis By thermogravimetric analysis, the decomposition temperatures of Eu (hfa) 3 [TPPO-Si (OEt) 3 ] 2 and SiO 2 -Eu (hfa) 3 [TPPO-Si (O) 3 ] 2 are respectively. It was confirmed that the temperature was 208 ° C and 306 ° C.
  • FIG. 5 shows Eu (hfa) 3 (H 2 O) 2 , Eu (hfa) 3 [TPPO-Si (OEt) 3 ] 2 , and SiO 2 -Eu (hfa) in the solid state.
  • 3 [TPPO-Si (O) 3 ] 2 is the excitation spectrum.
  • Eu (hfa) 3 [TPPO-Si (OEt) 3 ] 2 and SiO 2- Eu (hfa) 3 [TPPO-Si (O) 3 ] 2 there is a ⁇ - ⁇ * transition at 304 nm and 334 nm. Widespread absorption due to it was observed.
  • FIG. 6 shows Eu (hfa) 3 (H 2 O) 2 , Eu (hfa) 3 [TPPO-Si (OEt) 3 ] 2 , and SiO 2 -Eu (hfa) 3 [TPPO-Si (O) in the solid state. ) 3 ] 2 emission spectrum (excitation light: 356 nm). SiO 2 -Eu (hfa) 3 [TPPO-Si (O) 3 ] 2 compared to Eu (hfa) 3 (H 2 O) 2 and Eu (hfa) 3 [TPPO-Si (OEt) 3 ] 2. It showed a remarkably strong luminescence.
  • Figure 7 shows Eu (hfa) 3 (H 2 O) 2 , Eu (hfa) 3 [TPPO-Si (OEt) 3 ] 2 , and SiO 2 -Eu (hfa) 3 [TPPO-Si (O) in the solid state. ) 3 ] 2 , and a graph showing the emission attenuation of Eu (hfa) 3 [TPPO-Si (OEt) 3 ] 2 in solution.
  • Table 1 shows the photophysical characteristics of each Eu complex (emission lifetime ⁇ obs, radiation rate constant k r , non-radiation rate constant k nr , emission quantum efficiency ⁇ ff of 4f-4f transition, and total emission quantum yield ⁇ . tot ) is shown.
  • SiO 2- Eu (hfa) 3 [TPPO-Si (O) 3 ] 2 showed a relatively large kr and a small knr.
  • SiO 2- Eu (hfa) 3 [TPPO-Si (O) 3 ] 2 has a rare earth complex on the base material X due to immobilization of the rare earth complex on the base material X using two or more linker groups. It is considered that stable immobilization makes it possible to increase the radiation velocity and suppress the heat deactivation process, and to show high emission quantum efficiency.
  • Luminescent material having an Eu complex immobilized on silica nanoparticles SiO 2- Gd (hfa) 3 [TPPO-Si (O) 3 ] 2 ) SiO 2- Eu (hfa) 3 [TPPO-Si (O) 3 ] 2 ) except that Gd (hfa) 3 (H 2 O) 2 was used instead of Eu (hfa) 3 (H 2 O) 2.
  • Silica nanoparticles modified with a Gd complex SiO 2- Gd (hfa) 3 [TPPO-Si (O) 3 ] 2 ) were synthesized by the same procedure as in the synthesis of.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Luminescent Compositions (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne un matériau électroluminescent comprenant : un substrat qui comprend un oxyde métallique et/ou un sulfure métallique ; au moins deux groupes de liaison liés au substrat ; un ligand d'oxyde de phosphine lié à chacun des groupes de liaison, chaque ligand d'oxyde de phosphine présentant un groupe d'oxyde de phosphine unique ; et un ion de terre rare. Un complexe de terre rare est formé par un seul ion de terre rare et au moins deux ligands d'oxyde de phosphine.
PCT/JP2021/025663 2020-07-10 2021-07-07 Matériau électroluminescent, encre électroluminescente, corps électroluminescent et dispositif électroluminescent WO2022009930A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020119391A JP2023123882A (ja) 2020-07-10 2020-07-10 発光材料、発光インク、発光体及び発光デバイス
JP2020-119391 2020-07-10

Publications (1)

Publication Number Publication Date
WO2022009930A1 true WO2022009930A1 (fr) 2022-01-13

Family

ID=79553159

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2021/025663 WO2022009930A1 (fr) 2020-07-10 2021-07-07 Matériau électroluminescent, encre électroluminescente, corps électroluminescent et dispositif électroluminescent

Country Status (2)

Country Link
JP (1) JP2023123882A (fr)
WO (1) WO2022009930A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08310108A (ja) * 1994-12-28 1996-11-26 Hitachi Maxell Ltd 印刷物、インク組成物および熱転写記録媒体
JPH09249834A (ja) * 1996-03-14 1997-09-22 Hitachi Maxell Ltd 蛍光インク組成物およびこの蛍光インク組成物で形成される蛍光マ−ク
JP2003081986A (ja) * 2001-09-07 2003-03-19 Kansai Tlo Kk 希土類錯体並びにそれを用いた光機能材料及び発光装置
JP2009242385A (ja) * 2008-03-11 2009-10-22 Nara Institute Of Science & Technology 希土類金属錯体並びにそれを用いた波長変換材料
US20110220844A1 (en) * 2008-10-03 2011-09-15 Eric Tulsky Sulfonate modified nanocrystals
WO2016143561A1 (fr) * 2015-03-09 2016-09-15 国立大学法人北海道大学 Complexe polymère et procédé de production s'y rapportant
WO2019098286A1 (fr) * 2017-11-17 2019-05-23 国立大学法人北海道大学 Composé de terre rare, corps électroluminescent, dispositif électroluminescent, matériau de conversion de longueur d'onde et matériau de sécurité
WO2020004656A1 (fr) * 2018-06-28 2020-01-02 国立大学法人北海道大学 Complexe d'éléments des terres rares, agent d'imagerie optique pour radiothérapie, scintillateur pour détection de neutrons et dérivé de carborane

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08310108A (ja) * 1994-12-28 1996-11-26 Hitachi Maxell Ltd 印刷物、インク組成物および熱転写記録媒体
JPH09249834A (ja) * 1996-03-14 1997-09-22 Hitachi Maxell Ltd 蛍光インク組成物およびこの蛍光インク組成物で形成される蛍光マ−ク
JP2003081986A (ja) * 2001-09-07 2003-03-19 Kansai Tlo Kk 希土類錯体並びにそれを用いた光機能材料及び発光装置
JP2009242385A (ja) * 2008-03-11 2009-10-22 Nara Institute Of Science & Technology 希土類金属錯体並びにそれを用いた波長変換材料
US20110220844A1 (en) * 2008-10-03 2011-09-15 Eric Tulsky Sulfonate modified nanocrystals
WO2016143561A1 (fr) * 2015-03-09 2016-09-15 国立大学法人北海道大学 Complexe polymère et procédé de production s'y rapportant
WO2019098286A1 (fr) * 2017-11-17 2019-05-23 国立大学法人北海道大学 Composé de terre rare, corps électroluminescent, dispositif électroluminescent, matériau de conversion de longueur d'onde et matériau de sécurité
WO2020004656A1 (fr) * 2018-06-28 2020-01-02 国立大学法人北海道大学 Complexe d'éléments des terres rares, agent d'imagerie optique pour radiothérapie, scintillateur pour détection de neutrons et dérivé de carborane

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DUARTE ADRIANA P., MAULINE LÉÏLA, GRESSIER MARIE, DEXPERT-GHYS JEANNETTE, ROQUES CHRISTINE, CAIUT JOSÉ MAURÍCIO A., DEFFUNE ELENIC: "Organosilylated Complex [Eu(TTA) 3 (Bpy-Si)]: A Bifunctional Moiety for the Engeneering of Luminescent Silica-Based Nanoparticles for Bioimaging", LANGMUIR, AMERICAN CHEMICAL SOCIETY, US, vol. 29, no. 19, 14 May 2013 (2013-05-14), US , pages 5878 - 5888, XP055885259, ISSN: 0743-7463, DOI: 10.1021/la400365c *
FRANCIS BIJU, NEUHAUS BERNHARD, REDDY M. L. P., EPPLE MATTHIAS, JANIAK CHRISTOPH: "Amine‐Functionalized Silica Nanoparticles Incorporating Covalently Linked Visible‐Light‐Excitable Eu 3+ Complexes: Synthesis, Characterization, and Cell‐Uptake Studies", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, WILEY-VCH VERLAG , WENHEIM, DE, vol. 2017, no. 25, 7 July 2017 (2017-07-07), DE , pages 3205 - 3213, XP055885258, ISSN: 1434-1948, DOI: 10.1002/ejic.201700240 *
ITO KAZUYA, SEIJI WATASE, MITSURU WATANABE, NOBORU NISHIOKA, KIMIHIRO MATSUKAWA: "Coordination Hybrid of Silsesquioxane Containing Phosphine Oxide and an Europium Complex", JAPANESE JOURNAL OF POLYMER SCIENCE AND TECHNOLOGY, SOCIETY OF POLYMER SCIENCE JP, JP, vol. 67, no. 7, 1 July 2010 (2010-07-01), JP , pages 412 - 415, XP055885249, ISSN: 0386-2186, DOI: 10.1295/koron.67.412 *
NAKAJIMA AYAKO, NAKANISHI TAKAYUKI, KITAGAWA YUICHI, SEKI TOMOHIRO, ITO HAJIME, FUSHIMI KOJI, HASEGAWA YASUCHIKA: "Hyper-stable organo-EuIII luminophore under high temperature for photo-industrial application", SCIENTIFIC REPORTS, vol. 6, no. 1, 1 July 2016 (2016-07-01), pages 1 - 9, XP055885255, DOI: 10.1038/srep24458 *

Also Published As

Publication number Publication date
JP2023123882A (ja) 2023-09-06

Similar Documents

Publication Publication Date Title
CN110218220B (zh) 一种功能化金属-有机框架化合物、其形成的复合物及其制备方法和应用
Divya et al. Highly efficient visible light sensitized red emission from europium tris [1-(4-biphenoyl)-3-(2-fluoroyl) propanedione](1, 10-phenanthroline) complex grafted on silica nanoparticles
JP5737719B2 (ja) 希土類錯体及びその利用
JP2018505127A (ja) 金属錯体およびこれを含む色変換フィルム
WO2010032395A1 (fr) Nanocristaux de complexe de terre rare et leurs applications
CN111406059B (zh) 铕络合物
JP2019532912A (ja) 化合物およびこれを含む色変換フィルム
CN109593105A (zh) 金属配合物、有机电致发光器件、有机电致发光材料
WO2022009930A1 (fr) Matériau électroluminescent, encre électroluminescente, corps électroluminescent et dispositif électroluminescent
JP2008222885A (ja) 蛍光膜
JP2007326846A (ja) アゾベンゼン誘導体、蛍光性粒子およびその製造方法
CN115160588A (zh) 一类全光谱发光的、纳米级锆基金属有机框架材料及其制备方法
JP7274134B2 (ja) 希土類化合物、発光体、発光デバイス、波長変換材料及びセキュリティ材料
KR102677298B1 (ko) 피로메텐붕소 착체, 색변환 조성물, 색변환 필름, 광원 유닛, 디스플레이 및 조명 장치
CN110312729B (zh) 用于制备量子点的膦前体及由其制备的量子点
Li et al. Novel photoactive lanthanide hybrids covalently grafted on functionalized periodic mesoporous organosilicons (PMOs) by Schiff-base derivative
JP2022146969A (ja) フェナントロリン配位子を有する希土類錯体
JP7522554B2 (ja) ホスフィン前駆体、ホスフィン前駆体の製造方法、量子ドット製造用前駆体組成物、量子ドットを製造する方法
Celedón et al. Highly emissive host–guest based on nanoclay intercalated with an Eu 3+ complex bearing a new Ru 2+ organometallic ligand
WO2023167278A1 (fr) Matériau électroluminescent, capteur d'oxygène et matériau de revêtement
CN112384518B (zh) 稀土配合物、发光材料、发光体、发光装置、夹层玻璃用中间膜、夹层玻璃、车辆用挡风玻璃、波长转换材料以及安全材料
JP4660721B2 (ja) アゾベンゼン誘導体化合物、粒子およびその製造方法
WO2021132373A1 (fr) Complexe d'éléments des terres rares
WO2020241498A1 (fr) Complexe d'europium luminescent
KR20120119934A (ko) 실리카 나노 튜브, 그 제조방법 및 멀티 센서로 응용

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: 21837235

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21837235

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP