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WO2018047951A1 - Matériau électroluminescent, encre et dispositif électroluminescent - Google Patents

Matériau électroluminescent, encre et dispositif électroluminescent Download PDF

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Publication number
WO2018047951A1
WO2018047951A1 PCT/JP2017/032523 JP2017032523W WO2018047951A1 WO 2018047951 A1 WO2018047951 A1 WO 2018047951A1 JP 2017032523 W JP2017032523 W JP 2017032523W WO 2018047951 A1 WO2018047951 A1 WO 2018047951A1
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Prior art keywords
rare earth
light emitting
atom
luminescent material
group
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English (en)
Japanese (ja)
Inventor
中西　貴之
翼 岡井
長谷川　靖哉
北川　裕一
公志 伏見
一生 田中
正行 権
中條　善樹
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Hokkaido University NUC
Kyoto University NUC
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Hokkaido University NUC
Kyoto University NUC
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Priority to JP2018538491A priority Critical patent/JPWO2018047951A1/ja
Publication of WO2018047951A1 publication Critical patent/WO2018047951A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • 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

Definitions

  • the present invention relates to a light emitting material, and an ink and a light emitting device using the light emitting material.
  • Circularly polarized light emission is usually created by combining a linear polarization filter and a circular polarization filter. Instead, a luminescent material that can supply circularly polarized light without a filter has been proposed (for example, Non-Patent Document 1).
  • An object according to one aspect of the present invention is to provide a light-emitting material exhibiting circularly polarized light emission characteristics with a high anisotropy factor.
  • One aspect of the present invention includes a rare earth atom, a polyoxometalate containing a metal atom and an oxygen atom and coordinated to the rare earth atom, and an organic ligand coordinated to the rare earth atom.
  • a light emitting material including a rare earth complex.
  • the organic ligand contains an optically active compound, and the amount of one substance in the pair of enantiomers of the optically active compound in the light emitting material is larger than the amount of the other substance.
  • the rare earth complex has a remarkably high anisotropy by combining polyoxometalate and an organic ligand which is an optically active compound and has a large proportion of one enantiomer.
  • the circularly polarized light emission characteristics of the factor can be shown.
  • the rare earth complex may emit light by excitation light having a wavelength in the range of 400 to 550 nm.
  • a rare earth complex having an organic ligand exhibits absorption based on charge transfer from the organic ligand to the rare earth atom (CTS absorption), but according to the knowledge of the present inventors, the wavelength of CTS absorption that generates light emission. And anisotropy factor.
  • CTS absorption that produces light emission is in the range of 400 to 550 nm
  • the rare earth complex is considered to exhibit circularly polarized light emission characteristics with a high anisotropy factor.
  • a light emitting material exhibiting circularly polarized light emission characteristics with a high anisotropy factor can be provided.
  • FIG. 1 is a schematic view showing an embodiment of a light emitting material.
  • the light emitting material 20 shown in FIG. 1 is composed of a rare earth complex 10 and a plurality of amphiphilic compounds 4 surrounding the rare earth complex 10.
  • the rare earth complex 10 has a rare earth atom 1, a polyoxometalate 3 and an organic ligand 2 coordinated to the rare earth atom 1.
  • the organic ligand 2 is an optically active compound that can constitute at least one pair of enantiomers, and the ratio of one of the at least one pair of enantiomers of the optically active compound in the entire light emitting material 20 is greater than the other.
  • the amphiphilic compound 4 forms a micelle-like structure, and a plurality of molecules of the rare earth complex 10 can be contained inside each micelle.
  • the light emitting material 20 may include a crystal composed of the rare earth complex 10 and the amphiphilic compound 4.
  • the rare earth complex 10 in FIG. 1 has a so-called sandwich structure in which a rare earth atom 1 is sandwiched between two opposing polyoxometalates 3. Two rare earth atoms may be sandwiched between two polyoxometalates. However, the rare earth complex does not necessarily have to form a sandwich structure.
  • the rare earth atom 1 is not limited to the trivalent europium (Eu) in FIG. 1, for example, Sc, Y and lanthanoids (La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Er , Tm, Yb, Lu).
  • the rare earth atom 1 may be a lanthanoid, or may be at least one selected from the group consisting of Eu, Tb, Sm, Nd, Yb, Tm, Ce, Er and Pr. It may be Eu.
  • Rare earth atoms are usually present in the form of ions in rare earth complexes.
  • the valence of the rare earth atom is not particularly limited and can be appropriately selected.
  • Polyoxometalate 3 (POM) coordinated to rare earth atom 1 is generally composed of a plurality of metal atoms (M) and a plurality of oxygen atoms (O) coordinated thereto.
  • the polyoxometalate can be, for example, a Lindkvist type or Keggin type polyacid.
  • Polyoxometalates include, for example, MO 4 tetrahedron, MO 5 pentahedron, or MO 6 octahedron structures formed by metal atoms and oxygen atoms.
  • the polyoxometalate may have an octahedral structure (MO 6 octahedron) portion including one metal atom and six oxygen atoms coordinated to the metal atom.
  • the polyoxometalate may be an isopolyoxometalate composed of one kind of metal atom and oxygen atom, or a heteropolyoxometalate containing a hetero atom in addition to the isopolyoxometalate.
  • the polyoxometalate may be a complex including a plurality of the polyhedral structure parts and bonded to each other.
  • the metal atom contained in the polyoxometalate is not particularly limited, but may be at least one selected from the group consisting of Mo, W, V, Si, P, Ge, Al, and As, for example.
  • the metal atom contained in the polyoxometalate may be a hexavalent metal atom such as Mo and W, and these can form an octahedral structure.
  • the rare earth complex is not limited to the compound specifically shown in FIG. 1, and can contain any optically active compound as an organic ligand.
  • one substance amount (mole number) of a pair of enantiomers of the optically active compound is larger than the other substance amount (mole number).
  • the enantiomeric excess (ee) of the optically active compound exceeds 0%.
  • This enantiomeric excess is 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more. May be.
  • the enantiomeric excess is high, chirality is generated in the luminescent material, and as a result, the anisotropy factor in circularly polarized light emission is considered to be larger.
  • the optically active compound as the organic ligand can be an anion or a neutral ligand.
  • the optically active compound may be a ligand having a photosensitizing action capable of effectively exciting a rare earth atom.
  • enolates derived from diketones There are enolates derived from diketones. Specific examples of enolate which is an optically active compound include compounds represented by the following formula (I) and enantiomers thereof.
  • R 1 represents an optionally substituted hydrocarbon group
  • R 2 , R 3, and R 4 each independently represents an optionally substituted hydrocarbon group
  • R 5 , R 6 , R 7 And R 8 each independently represents a hydrogen atom, a halogen atom or an optionally substituted hydrocarbon group.
  • R 1 may be an optionally substituted alkyl group, and may have 1 to 10 carbon atoms.
  • R 1 may be a fluorinated alkyl group, and examples thereof include a trifluoromethyl group (—CF 3 ) and a perfluoropentyl group (—CF 2 CF 2 CF 3 ).
  • R 2 , R 3 and R 4 may be an alkyl group which may be substituted, and may have 1 to 5 carbon atoms. Specific examples of R 2 , R 3 and R 4 include a methyl group.
  • R 5 , R 6 , R 7 and R 8 may each independently be an optionally substituted alkyl group, and the carbon number thereof may be 1-5.
  • R 5 , R 6 , R 7 and R 8 may be a hydrogen atom.
  • Examples of the set of enantiomers of the optically active compound represented by the formula (I) include a combination of a compound represented by the following formula (1a) and a compound represented by the following formula (1b).
  • R 1 in these formulas is as defined above, and may be a fluorinated alkyl group in particular.
  • the substance amount of the compound of formula (1a) contained in the luminescent material may be larger than the substance amount of the compound of formula (1b) contained in the luminescent material, or vice versa.
  • Ar 1 in the formula (II) represents an optionally substituted aryl group, and specific examples thereof include a phenyl group.
  • R 11 represents an optionally substituted alkyl group or an optionally substituted aryl group
  • R 12 represents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted group.
  • An aryl group is shown.
  • R 11 and R 12 may each independently be an alkyl group having 1 to 5 carbon atoms, and specific examples thereof include a methyl group and an isopropyl group. Specific examples of the aryl group as R 11 or R 12 include a phenyl group.
  • Organic ligands can also be selected based on wavelengths that produce absorption (CTS absorption) based on charge transfer from organic ligands to rare earth atoms.
  • CTS absorption absorption
  • the rare earth complex tends to exhibit a particularly high anisotropy factor. Therefore, the effect of increasing the anisotropy factor can be even more remarkable by using as the organic ligand an optically active compound whose rare earth complex exhibits blue belt CTS absorption.
  • the rare earth complex emits light by absorption of blue-banded CTS means that in the excitation spectrum using a solution in which the rare earth complex is dissolved as a sample, fluorescence in the visible light range (380 to 750 nm) is in the range of excitation light of 400 to 550 nm. This can be confirmed by observation.
  • the rare earth complex When the number of oxygen atoms coordinated to one rare earth atom (oxygen coordination number) is large, the rare earth complex tends to have blue-band CTS absorption. Specifically, the oxygen coordination number in the rare earth complex may be 7 to 11. Furthermore, if the energy levels of the organic ligands HOMO and LUMO are high, the rare earth complex tends to have blue-band CTS absorption. Therefore, pay attention to the energy levels of HOMO and LUMO. It is also possible to design a rare earth complex having a blue belt color CTS absorption.
  • One or two or more optically active compounds can coordinate to one rare earth atom in the rare earth complex.
  • the rare earth complex may further contain other organic ligands in addition to the optically active compound.
  • the amphiphilic compound 4 is arranged around the rare earth complex 10 so that the hydrophilic group 4a is on the rare earth complex 10 side, and the hydrophilic group 4a and the rare earth complex 10 interact with each other.
  • the content of the amphiphilic compound in the light emitting material may be 1 to 100 or 2 to 20 with respect to the mass of the rare earth complex.
  • the amphiphilic compound 4 is a molecule that has a hydrophilic group 4a and a hydrophobic group 4b and functions as a micelle forming agent also called a surfactant.
  • the rare earth complex forms a complex with the amphiphilic compound, the rare earth complex can have good solubility in a solvent.
  • the hydrophilic group of the amphiphilic compound may be a cationic group.
  • the hydrophilic group include an ammonium group, a pyridinium group, a carboxylate group, a sulfate group, and a sulfonate group.
  • the hydrophilic group may be a cationic group selected from an ammonium group and a pyridinium group.
  • the hydrophobic group include an alkyl group having 6 to 18 carbon atoms, an alkylbenzene group having 6 to 16 carbon atoms, an alkylnaphthalene group, a perfluoroalkyl group having 4 to 9 carbon atoms, polypropylene oxide, and polysiloxane.
  • the alkyl group may be linear or branched alkyl.
  • Amphiphilic compounds include cetyltrimethylammonium bromide (CTA), dimethyldioctadecylammonium bromide (DODA), dodecyltrimethylammonium bromide (DDTA), dodecyl-11 methacryloxyundecyldimethylammonium bromide (DMDA), and di11 hydroxyun. It may be at least one selected from the group consisting of decyldimethylammonium bromide (DODHA).
  • CBDA cetyltrimethylammonium bromide
  • DODA dimethyldioctadecylammonium bromide
  • DDTA dodecyltrimethylammonium bromide
  • DMDA dodecyl-11 methacryloxyundecyldimethylammonium bromide
  • DODHA decyldimethylammonium bromide
  • the light emitting material contains a rare earth complex and an amphiphilic compound as main components.
  • the total content of the rare earth complex and the amphiphilic compound in the luminescent material may be 80% by mass or more, 90% by mass or more, or 95% by mass or more based on the mass of the luminescent material.
  • the light-emitting material includes, for example, a step of dissolving a complex of an inorganic rare earth complex having a rare earth atom and a polyoxometalate coordinated with the rare earth atom in an organic solvent, and an optically active rare earth atom in the organic solvent. And a step of coordinating an organic ligand containing a compound, in this order.
  • the optically active compound those optically resolved in advance by a usual method can be used.
  • An inorganic rare earth complex containing a rare earth atom and a polyoxometalate can be prepared by an ordinary method understood by those skilled in the art. For example, methods for preparing europium-polyoxometalate complexes are described in References: Yamase et al., Chem. Rev. 1998, vol 98, p307-325.
  • a complex of an inorganic rare earth complex and an amphiphilic compound can be obtained, for example, by reacting an inorganic rare earth complex and an amphiphilic compound in a solution. The produced complex may be purified by recrystallization or the like.
  • the organic solvent used in this reaction may be a halogen-based organic solvent, and examples thereof include chloroform and dichloromethane.
  • the generated light emitting material (a complex of a rare earth complex and an amphiphilic compound) may be purified by recrystallization or the like.
  • the light emitting material has excellent circularly polarized light emission characteristics
  • application to various uses such as an ink for forming a light emitting layer, a light emitting film, or a circularly polarized light emitting device is assumed.
  • the ink may contain, for example, a light emitting material and a solvent that dissolves or disperses the light emitting material.
  • the light emitting layer or light emitting film containing the light emitting material can contain, for example, the light emitting material and a polymer matrix in which the light emitting material is dissolved or dispersed.
  • chloroform layer was recovered from the reaction solution using a separatory funnel, and magnesium sulfate was added thereto for dehydration. After removing the magnesium sulfate, chloroform was distilled off using an evaporator. Chloroform was added to the residue, and a complex of Eu-POM and CTA (CTA-Eu-POM, white solid) was obtained by recrystallization.
  • the obtained Eu ((+)-facam) (POM) was analyzed by X-ray diffraction (XRD) and infrared spectroscopy.
  • FIG. 2 shows an infrared absorption spectrum of Eu ((+)-facam) (POM)
  • FIG. 3 shows an XRD pattern of Eu ((+)-facam) (POM). From the analysis results including these, it was confirmed that a complex of rare earth complex coordinated with (+)-facam and CTA was formed. It was also confirmed that Eu ((+)-facam) (POM) was dissolved in dichloromethane and chloroform to form a transparent solution.
  • FIG. 4 shows the excitation spectrum of Eu ((+)-facam) (POM).
  • Eu ((+)-facam) (POM) a rare earth complex
  • Eu ((+)-facam) (POM) was confirmed to absorb excitation light in the blue region (400 to 550 nm) and emit fluorescence in the visible region.
  • Eu ((-)-facam) (POM) Europium (Eu) was prepared in the same manner as the (+) form except that 3- (trifluoromethylhydroxymethylene)-( ⁇ )-camphorate (( ⁇ )-facam) was used instead of (+)-facam.
  • a europium complex having a polyoxometalate containing tungsten (W) and 3- (trifluoromethylhydroxymethylene)-( ⁇ )-camphorate as an organic ligand, and cetyl as an amphiphilic molecule
  • a luminescent material composed of trimethylammonium bromide (Eu (( ⁇ )-facam) (POM)) was synthesized.
  • Eu (( ⁇ )-facam) (POM) it was confirmed by the same analysis as Eu ((+)-facam) (POM) that a complex of rare earth complex and CTA was formed. It was.
  • Eu ((+)-fpcam) (POM) Eu (( ⁇ )-fpcam) (POM) Instead of (+)-facam, 3- (perfluoropropylhydroxymethylene)-(+)-camphorate ((+)-fpcam), or 3- (perfluoropropylhydroxymethylene)-( ⁇ )-camphorate (( ⁇ ) -Fpcam) in the same procedure as Eu ((+)-facam) (POM), and a polyoxometalate containing europium (Eu), tungsten (W), and an organic ligand.
  • Eu europium
  • W tungsten
  • FIG. 5 shows circularly polarized emission spectra of Eu ((+)-facam) (POM) and Eu (( ⁇ )-facam) (POM).
  • FIG. 6 shows the circular polarized emission spectra of Eu ((+)-fpcam) (POM) and Eu (( ⁇ )-fpcam) (POM).
  • Table 1 were obtained from these circularly polarized emission spectra, 7 F 0 - shows 5 D 2 g value corresponding to the transition (g CPL) - 5 D 1 transition or 7 F 0.
  • the luminescent material exhibited a very high g value exceeding 1.0.
  • SYMBOLS 1 Rare earth atom, 2 ... Organic ligand, 3 ... Polyoxometalate, 4 ... Amphiphilic compound, 4a ... Hydrophilic group, 4b ... Hydrophobic group, 10 ... Rare earth complex, 20 ... Luminescent material.

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Abstract

L'invention concerne un matériau électroluminescent contenant un complexe de terre rare qui a : un atome de terre rare ; un polyoxométalate qui est coordonné à l'atome de terre rare et contient un atome de métal et un atome d'oxygène ; et un ligand organique qui est coordonné à l'atome de terre rare. Le ligand organique contient un composé optiquement actif ; et la quantité de substance d'un énantiomère d'une paire d'énantiomères du composé optiquement actif dans le matériau électroluminescent est plus élevée que la quantité de substance de l'autre énantiomère.
PCT/JP2017/032523 2016-09-09 2017-09-08 Matériau électroluminescent, encre et dispositif électroluminescent Ceased WO2018047951A1 (fr)

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Citations (11)

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WO2016143562A1 (fr) * 2015-03-09 2016-09-15 国立大学法人北海道大学 Complexe de terres rares, matériau luminescent et procédé de fabrication de celui-ci, et feuille luminescente et son procédé de production
JP2017137415A (ja) * 2016-02-03 2017-08-10 東ソー株式会社 キラル型希土類錯体ポリマーおよびそれを用いた光学機能材料

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JP2005111704A (ja) * 2003-10-03 2005-04-28 Dainippon Ink & Chem Inc 識別マーク、及び該識別マークの判別方法、及び判別システム、並びに該識別マークを形成するためのラベル、及び転写箔
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WO2016143562A1 (fr) * 2015-03-09 2016-09-15 国立大学法人北海道大学 Complexe de terres rares, matériau luminescent et procédé de fabrication de celui-ci, et feuille luminescente et son procédé de production
JP2017137415A (ja) * 2016-02-03 2017-08-10 東ソー株式会社 キラル型希土類錯体ポリマーおよびそれを用いた光学機能材料

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YUICHI KITAGAWA ET AL.: "Kidorui Sakutai no Haiishi ni Izon shita Jiki En Henko Nishokusei Kyodo", ANNUAL MEETING ON PHOTOCHEMISTRY KOEN YOSHISHU, 8 September 2015 (2015-09-08) *

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