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WO2010032395A1 - Nanocristaux de complexe de terre rare et leurs applications - Google Patents

Nanocristaux de complexe de terre rare et leurs applications Download PDF

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Publication number
WO2010032395A1
WO2010032395A1 PCT/JP2009/004411 JP2009004411W WO2010032395A1 WO 2010032395 A1 WO2010032395 A1 WO 2010032395A1 JP 2009004411 W JP2009004411 W JP 2009004411W WO 2010032395 A1 WO2010032395 A1 WO 2010032395A1
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WO
WIPO (PCT)
Prior art keywords
group
rare earth
thiophene
branched
heterocyclic ring
Prior art date
Application number
PCT/JP2009/004411
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English (en)
Japanese (ja)
Inventor
長谷川靖哉
河合壯
中川哲也
Original Assignee
国立大学法人奈良先端科学技術大学院大学
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Publication of WO2010032395A1 publication Critical patent/WO2010032395A1/fr

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    • 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 Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5345—Complexes or chelates of phosphine-oxides or thioxides with metallic compounds or metals
    • 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 Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5329—Polyphosphine oxides or thioxides
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium
    • 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
    • C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
    • 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

Definitions

  • the present invention relates to a rare earth complex having luminescent properties, and more particularly to a rare earth complex nanocrystal, a luminescent material and a light emitting device using the nanocrystal.
  • rare earth ions emit light in a wide wavelength range from ultraviolet to infrared. These luminescences are based on electronic transitions derived from f-orbitals that are not easily affected by external fields such as ligand fields. For this reason, the wavelength width of the emission band is very narrow compared to organic phosphors and the like, and in principle, the color purity is extremely useful. In addition, organic phosphors are inferior in stability to heat, light, and excitation. Moreover, since rare earth ions are non-toxic, they are easy to use industrially. Thus, since rare earth ions have excellent characteristics, rare earth complexes in which various ligands are coordinated with rare earth ions are used in various applications. Specifically, it is used for various applications such as luminescent ink and organic electroluminescence element.
  • Non-Patent Document 1 discloses that when the ligand coordinated to Eu (III) is variously changed, the emission characteristics of the complex change depending on the structure of the ligand. Furthermore, the present inventors have developed many rare earth complexes so far (see, for example, Patent Documents 1 to 4).
  • the luminous efficiency of the rare earth complexes used so far is 40-50% at most, and the excitation energy is not effectively utilized.
  • the present invention has been made in view of the above problems, and an object of the present invention is to provide a light-emitting material having improved light emission efficiency and improved light emission efficiency of the rare earth complex.
  • the luminescent material according to the present invention has the general formulas (I) to (III)
  • the nanocrystals are more preferably dispersed or suspended.
  • Ln is a rare earth atom
  • R 1 to R 4 and R 6 may be the same as or different from each other, and the number of carbon atoms having a straight or branched chain
  • R 5 and R 7 may be the same or different from each other, and
  • the rare earth complex used in the present invention has the structure as described above, light energy for exciting the rare earth ions is difficult to be released as thermal energy, and as a result, the rare earth ions are sufficiently excited, Strong emission intensity is maintained.
  • the rare earth complex exists in a nanocrystalline state, it is not easily affected by the dispersion medium (for example, a polymer or the like), and exhibits strong light emission characteristics. Further, since the rare earth complex in a crystalline state is hardly affected by oxygen or water, it has high durability.
  • the crystal size is preferably 200 nm or less, and more preferably 100 nm or less because the visible light transmittance is very high.
  • the luminescent material according to the present invention includes a rare earth complex crystal represented by any one of the above-described general formulas (I) to (III) in order to emit light using excitation by ultraviolet light. It is characterized by that. Since the extinction coefficient in the ultraviolet light of the rare earth complex existing in the crystalline state is several orders of magnitude higher than the extinction coefficient in the visible light, high emission can be provided by emitting light using excitation by ultraviolet light. .
  • the ultraviolet light applied to the luminescent material according to the present invention is preferably 370 nm or less, and more preferably 200 to 365 nm.
  • the ink according to the present invention is characterized by containing the above-described luminescent material.
  • the ink according to the present invention may be used for offset printing or inkjet.
  • the pigment according to the present invention is characterized by containing the above-mentioned luminescent material.
  • Art objects to which the pigments according to the invention are applied are also within the scope of the invention.
  • the information identification medium according to the present invention is characterized by containing the above-mentioned luminescent material.
  • the information identification medium according to the present invention may be applied to an ID card.
  • the light emitting device includes a rare earth complex crystal represented by any one of the above general formulas (I) to (III), a light emitting material containing the crystal, and a light source capable of emitting light in the ultraviolet region. It is characterized by having. More preferably, the light-emitting device according to the present invention further includes a filter that blocks visible light to infrared light from the light source.
  • the crystal of the rare earth complex is preferably a nanocrystal, the crystal size is more preferably 200 nm or less, and further preferably 100 nm or less.
  • the light emitting device is a light source that emits visible light. It can provide much stronger light than those equipped with.
  • the method of emitting light of the rare earth complex according to the present invention is to irradiate the crystal of the rare earth complex represented by any one of the above general formulas (I) to (III) or a light emitting material containing the crystal with ultraviolet light. It includes the process of performing.
  • the present invention it is possible to obtain light emission with higher color purity and higher light emission intensity than inorganic light emitters. Accordingly, it is possible to provide a luminescent polymer and a luminescent ink with higher emission intensity, and an illumination device, a signal device, and a display device with higher emission intensity.
  • the present invention provides a luminescent material comprising nanocrystals of a rare earth complex.
  • the luminescent material according to the present invention is a composition containing dispersed nanocrystals of the rare earth complex described above.
  • the luminescent material according to the present invention is a composition containing suspended nanocrystals of the rare earth complex described above.
  • the rare earth complex mentioned above may be contained singly or in combination.
  • the content of the rare earth complex in the luminescent material according to the present embodiment is not particularly limited, and can be appropriately set according to the specific application and the type of the dispersion medium.
  • a specific ligand is coordinated to a rare earth ion.
  • the rare earth ion is not particularly limited as long as it is a rare earth metal ion, but is preferably a trivalent lanthanoid ion, and particularly Eu 3+ , Sm 3+ , Tb 3+ , Yb 3+ , Nd 3+ , Ce 3+ , Dy 3+. More preferably, Er 3+ , Pr 3+ or Tm 3+ .
  • the rare earth ions used in the present invention are more preferably Eu 3+ , Sm 3+ , Tb 3+ , Yb 3+ or Nd 3+ .
  • the luminescent material according to the present invention has the general formulas (I) to (III)
  • nanocrystal of the rare earth complex represented by either, It is preferable that the said nanocrystal is disperse
  • Ln in the general formulas (I) to (III) is a rare earth atom, and the rare earth atom is preferably Eu, Sm, Tb, Yb, Nd, Ce, Dy, Er, Pr, or Tm, and Eu, Sm More preferably, Tb, Yb or Nd.
  • R 1 to R 4 and R 6 may be the same as or different from each other, and may be a linear or branched alkyl group or alkenyl group. Or an alkynyl group, a cycloalkyl group, a cycloalkenyl group, an aryl group or a heteroaryl group, a heterocyclic ring (excluding thiophene), a halogen group, a hydroxyl group, a sulfonic acid group, a carbonyl group, a nitro group, a cyano group, or an amino group R 5 and R 7, which may be the same or different from each other, are a linear or branched alkylene group, arylene group, alkenyl group or alkynyl group, or cycloalkyl group, cycloalkenyl group An aryl or heteroaryl group, or oxygen, nitrogen or sulfur, or a heterocyclic ring (thioph)
  • the alkyl group preferably has 1 to 20 carbon atoms, and more preferably 1 to 8 carbon atoms.
  • the alkenyl group and alkynyl group preferably have 2 to 20 carbon atoms, and more preferably 2 to 8 carbon atoms.
  • the cycloalkyl group and cycloalkenyl group preferably have 3 to 20 carbon atoms, and more preferably 4 to 11 carbon atoms.
  • the aryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 10 carbon atoms, and further preferably a phenyl group, a naphthyl group, a biphenyl group, an anthracenyl group, or a phenanthryl group.
  • the heteroaryl group preferably has 3 to 20 carbon atoms, and more preferably 4 to 11 carbon atoms.
  • the heterocyclic ring is preferably a 5-membered or 6-membered ring, a single ring or 2 to 6 condensed rings.
  • Examples of the 5-membered heterocyclic ring include furan, pyrrole, oxazole, isoxazole, thiazole, imidazole, and pyrazole.
  • Examples of the 6-membered heterocyclic ring include pyridine, pyran, triazine, and the like.
  • 6-membered condensed ring examples include benzofuran, coumarin, benzopyran, carbazole, xanthene, quinoline, dibenzofuran, and the like, but are not limited thereto as long as they do not have a thiophene structure.
  • the alkylene group preferably has 1 to 20 carbon atoms, and more preferably 1 to 8 carbon atoms.
  • the arylene group preferably has 6 to 18 carbon atoms, more preferably 6 to 10 carbon atoms, and still more preferably a phenylene group, a naphthylene group, a biphenylene group, an anthracenylene group, or a phenanthrylene group.
  • Examples of the C 1 -C 20 linear or branched group that does not contain a hydrogen atom include perhalogenated alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, cycloalkenyl groups, aromatic groups, Examples include, but are not limited to, a heteroaromatic group or an aralkyl group, and may be an ether, ester, or ketone in which one or more —O— or the like is interposed between any of these C—C bonds. .
  • one or more of the halogen atoms bonded to the aromatic ring of the perhalogenated aromatic group, the perhalogenated heteroaromatic group, or the perhalogenated aralkyl group is a substituent that does not contain a hydrogen atom (for example, cyano, nitro, Nitroso, C 1 -C 4 perhalogenated alkoxy, C 2 -C 5 perhalogenated alkoxycarbonyl, C 2 -C 20 perhalogenated alkylcarbonyloxy, etc.).
  • the group having a C 1 to C 20 straight or branched chain that does not contain a hydrogen atom is more preferably a perfluorinated alkyl group or a perfluorinated alkenyl group, and is preferably C 1 to C 4. More preferred is CF 3 .
  • the rare earth complex used in the present invention is:
  • the dispersion medium used for the luminescent material according to the present embodiment is not particularly limited, and a preferable medium can be appropriately selected depending on the application.
  • preferable media include resins, inorganic materials, and organic-inorganic hybrid materials.
  • the resin include polyimide resin, polyamide resin, polymethyl methacrylic resin, polyacrylate, polystyrene resin, polyethylene naphthalate resin, polyester resin, polyurethane, polycarbonate resin, epoxy resin, polyethylene terephthalate resin, and chloride.
  • Examples thereof include vinyl resins, vinylidene chloride resins, acrylonitrile butadiene styrene (ABS) resins, acrylonitrile styrene (AS) resins, cycloolefin resins, siloxane polymers, and halides or deuterides thereof. These resins may be used alone or in combination of two or more.
  • Examples of the inorganic material include glass prepared by a sol-gel method.
  • an additive for imparting a specific function may be further added to the luminescent material according to the present embodiment, depending on its application.
  • additives include additives such as antioxidants, inorganic fillers, stabilizers, antistatic agents, dyes, pigments, flame retardants, inorganic fillers, and elastomers for improving impact resistance. it can.
  • additives, such as a lubricant can also be added for the purpose of improving the workability of the luminescent material according to this embodiment.
  • a leveling agent may be added when casting the luminescent material which concerns on this embodiment, and shape
  • antioxidants examples include 2,6-di-t-butyl-4-methylphenol, 2,2′-dioxy-3,3′-di-t-butyl-5,5′-dimethylphenylmethane. Tetrakis [methylene-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] methane, 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) Butane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxybenzyl-benzene, stearyl- ⁇ - (3,5-di-t-butyl-4 -Hydroxyphenyl) propionate, 2,2'-dioxy-3,3'-di-t-butyl-5,5'-diethylphenylmethane, 3,9-bis [1,1-dimethyl-2- [ ⁇ - (3-t-butyl-4- Hydroxy
  • examples of the inorganic filler include calcium carbonate, carbon fiber, and metal oxide.
  • leveling agent examples include a fluorine-based nonionic surfactant, a special acrylic resin leveling agent, and a silicone leveling agent.
  • the shape of the luminescent material according to the present embodiment is not particularly limited, and examples thereof include a plate shape, a powder shape, a granular shape, a granular shape, a paste shape, a liquid shape, and an emulsion shape. Since the luminous efficiency is improved by existing in a crystalline state, a plate shape, a powder shape, a granular shape, and a granular shape are preferable.
  • the method for producing the luminescent material according to the present embodiment is not particularly limited, and a suitable method may be selected as appropriate according to the composition, shape, application, and the like.
  • the luminescent material is a powder
  • the rare earth complex, the medium, and, if necessary, other additives as exemplified above are mixed in a twin screw extruder, Brabender, roll kneader, etc. It can be produced by a method of pelletizing using an extruder or a method of further pulverizing pellets by a pulverizer to form a powder.
  • the luminescent material according to the present invention may be in the form of a carrier carrying the above-mentioned rare earth complex nanocrystals on the surface.
  • a carrier carrying the above-mentioned rare earth complex nanocrystals on the surface.
  • One kind of the above-mentioned rare earth complex may be supported on such a support, or a plurality of kinds may be mixed and supported.
  • the amount of the rare earth complex supported on the luminescent material according to the present embodiment is not particularly limited, and can be appropriately set according to the specific application and the type of the carrier.
  • the manufacturing method of the luminescent material according to the present embodiment is not particularly limited.
  • it can be produced by casting a dispersion or suspension of a luminescent material on a carrier (polymer or substrate) and subjecting the resulting solution layer to removal treatment of the dispersion medium or the like.
  • the method for casting on a carrier is not particularly limited.
  • a coating film of the luminescent material according to the present embodiment can be manufactured by forming a coating film of the luminescent material according to the present embodiment on the surface of the carrier.
  • a conventionally known method for example, brush coating method, dip coating method, spray coating method, plate coating method, spinner coating method, bead coating method, curtain coating method
  • wet methods gravure printing methods, screen printing methods, offset printing methods, letterpress printing methods, and other film forming methods
  • the carrier used for the luminescent material according to the present embodiment is not particularly limited, and a preferable carrier can be appropriately selected according to the application.
  • Preferred carriers include the above-described resins, inorganic materials, organic-inorganic hybrid materials, and the like.
  • the present invention provides a light-emitting device including a rare-earth complex crystal or a light-emitting material containing the crystal, and a light source capable of emitting light in the ultraviolet region.
  • the rare earth complex used in the light emitting device according to the present invention is not particularly limited as long as it is described above.
  • the light source is not particularly limited as long as it is a light source capable of emitting light in the ultraviolet region.
  • short wavelength semiconductor lasers As the light source used in the present invention, a light source that irradiates only ultraviolet light is preferable.
  • the light emitting device according to the present invention includes a filter that blocks visible light to infrared light together with the various light sources described above. Only ultraviolet light can be supplied.
  • the present invention also provides a method for causing a rare earth complex to emit light.
  • the light-emitting method according to the present invention includes a step of irradiating ultraviolet light to a crystal of a rare earth complex or a light-emitting material containing the crystal. There is no particular limitation.
  • the rare earth complex used in the present invention has different emission characteristics depending on the type of organic ligand and rare earth ions constituting the complex. That is, each of the rare earth complexes used in the present invention has unique emission characteristics. Further, by changing the combination of the organic ligand and the rare earth ion, the light emission characteristics of the rare earth complex used in the present invention can be changed.
  • the luminescent material according to the present invention can be used as an information identification medium.
  • the present invention provides an information recording medium (for example, an ID card) for recording or storing information and signals.
  • An information recording medium according to the present invention is characterized by containing the above-described luminescent material.
  • the luminescent material according to the present invention can be used for an information identification medium such as an ID card.
  • the shape and form of the information identification medium according to the present invention are not particularly limited.
  • the information identification medium according to the present invention can be in the shape and form of, for example, a card, a film, a seal, an armband, etc., molded from a resin containing the luminescent material according to the present invention.
  • images, figures, and characters printed or printed using the ink containing the luminescent material according to the present invention can be used as the information identification medium.
  • the kind of rare earth complex contained in the information identification medium based on this invention may be one, it is preferable that it is multiple types.
  • the light emission pattern described above includes not only light emission from a rare earth complex composed of a single rare earth ion (eg, Eu 3+ ) but also light emission from a rare earth complex composed of other rare earth ions (eg, Sm 3+ , Tb 3+, etc.). It may be.
  • a new information recording medium can also be obtained by using a rare earth complex nanocrystal having a photochromic ligand. That is, a change in light emission characteristics (intensity, etc.) can also be used for identification. As a result, the discrimination power (security) of the information identification medium can be enhanced.
  • inks for printing or printing images, figures and characters, and pigments for producing artworks such as paintings are also within the scope of the present invention.
  • the present invention provides an ink or pigment.
  • the ink or pigment according to the present invention is characterized by containing the above-described luminescent material.
  • the ink according to the present invention may be used for offset printing or inkjet.
  • art objects coated with the pigment according to the present invention are also within the scope of the present invention.
  • Luminescence efficiency can be greatly improved by using rare earth complexes in a nanocrystalline state. Therefore, this invention can provide the luminescent ink and / or organic electroluminescent element which were far superior to the past.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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Abstract

L'invention porte sur des matériaux électroluminescents contenant des nanocristaux de complexe de terre rare. Les nanocristaux du complexe de terre rare sont de préférence dispersés ou en suspension, et le rendement d'émission de lumière est amélioré par l'utilisation du complexe de terre rare sous la forme de cristaux, et notamment sous la forme de nanocristaux. Un niveau élevé d'émission de lumière peut être obtenu, même avec une lumière d'excitation extrêmement faible, par excitation de tels matériaux électroluminescents avec de la lumière ultraviolette. Ainsi, le rendement d'émission de lumière du complexe de terre rare peut être amélioré et des matériaux électroluminescents avec un excellent rendement d'émission de lumière peuvent être élaborés.
PCT/JP2009/004411 2008-09-19 2009-09-07 Nanocristaux de complexe de terre rare et leurs applications WO2010032395A1 (fr)

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JP2008-241703 2008-09-19

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Cited By (10)

* Cited by examiner, † Cited by third party
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JP2011157279A (ja) * 2010-01-29 2011-08-18 Toshiba Corp 希土類錯体、及びそれを用いた蛍光媒体、発光素子、セキュリティー媒体並びに照明装置
JP2012061794A (ja) * 2010-09-17 2012-03-29 Toshiba Corp 情報記録媒体、その真偽判定方法、及び真偽判定システム
JP2013121921A (ja) * 2011-12-09 2013-06-20 Nara Institute Of Science & Technology 円偏光発光性希土類錯体
CN103728852A (zh) * 2012-10-16 2014-04-16 富士施乐株式会社 透明的静电荷图像显影用色调剂、其制造方法、显影剂、色调剂盒、图像形成方法及设备
JP2014094983A (ja) * 2012-11-07 2014-05-22 Laser System:Kk 発光性複合材料および発光体ナノ結晶
JP2014112643A (ja) * 2012-10-03 2014-06-19 Bridgestone Corp 太陽電池用封止膜及びこれを用いた太陽電池
JP2016044227A (ja) * 2014-08-22 2016-04-04 パナソニック株式会社 蛍光体含有硬化物とその製造方法
WO2018155557A1 (fr) * 2017-02-27 2018-08-30 国立大学法人北海道大学 Complexe de terre rare et élément électroluminescent
WO2019053963A1 (fr) * 2017-09-15 2019-03-21 大日本印刷株式会社 Composition d'encre, matière imprimée et procédé de détermination d'authenticité
WO2019053962A1 (fr) * 2017-09-15 2019-03-21 大日本印刷株式会社 Composition d'encre et imprimé

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JPWO2019053963A1 (ja) * 2017-09-15 2020-10-15 大日本印刷株式会社 インキ組成物、印刷物、及び、真贋判定方法
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