WO2013088959A1 - Élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage - Google Patents

Élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage Download PDF

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WO2013088959A1
WO2013088959A1 PCT/JP2012/080815 JP2012080815W WO2013088959A1 WO 2013088959 A1 WO2013088959 A1 WO 2013088959A1 JP 2012080815 W JP2012080815 W JP 2012080815W WO 2013088959 A1 WO2013088959 A1 WO 2013088959A1
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general formula
organic
represented
light
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大津　信也
大野　香織
三浦　紀生
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コニカミノルタ株式会社
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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 Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • H—ELECTRICITY
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    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
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    • 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
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    • 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
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1425—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/145—Heterocyclic containing oxygen as the only heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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    • 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

Definitions

  • the present invention relates to an organic electroluminescence element, a display device, and a lighting device.
  • An organic electroluminescence element (hereinafter also referred to as an organic EL element) has a structure in which a light emitting layer containing a light emitting compound is sandwiched between a cathode and an anode, and recombines by injecting electrons and holes into the light emitting layer.
  • a light emitting layer containing a light emitting compound is sandwiched between a cathode and an anode, and recombines by injecting electrons and holes into the light emitting layer.
  • Non-Patent Document 1 Since an organic EL device using phosphorescence emission from an excited triplet with an upper limit of internal quantum efficiency of 100% has been reported by Princeton University (for example, see Non-Patent Document 1), Research has become active (see, for example, Non-Patent Document 2 and Patent Document 1).
  • Non-Patent Document 3 As a material exhibiting phosphorescence at room temperature, a heavy metal complex such as an iridium complex has been studied (for example, see Non-Patent Document 3).
  • Non-patent Document 2 a tris (2-phenylpyridine) iridium complex is widely known (Non-patent Document 2), and a silyl group is added to the tris (2-phenylpyridine) skeleton for the purpose of improving the durability and luminous efficiency of the dopant.
  • An iridium complex having an introduced ligand is disclosed (for example, see Patent Document 2).
  • Patent Document 2 An iridium complex having an introduced ligand is disclosed (for example, see Patent Document 2).
  • Patent Document 2 an organic EL device using these dopants, sufficient device performance including a light emission lifetime has not been obtained.
  • iridium complexes having phenylimidazole ligands and carbene ligands are disclosed as other than tris (2-phenylpyridine) iridium complexes (see, for example, Patent Documents 3 and 4). These materials are very interesting because they can emit shortwave light compared to complexes composed of phenylpyridine ligands.
  • the luminous efficiency and lifetime of the organic EL element are not sufficient, and further improvement in performance is required.
  • An object of the present invention is to provide an organic electroluminescence element that exhibits high light emission efficiency, has a long light emission lifetime, and can suppress an increase in voltage during driving, and an illumination device and a display device including the element.
  • an organic electroluminescence device having at least one light emitting layer between an anode and a cathode
  • an organic electroluminescence device characterized by containing a hexadentate ortho metal iridium complex represented by the following general formula (I).
  • V represents a divalent linking group and is linked to L 2 and L 3 by a covalent bond.
  • L 1 to L 3 are each represented by the following general formula (II), wherein X 5 and Ir in the general formula (II) are coordinated, and X 7 and Ir in the general formula (II) form a covalent bond. ing.
  • X 1 to X 5 are an element group forming a nitrogen-containing heterocycle, selected from a carbon atom or a nitrogen atom, and at least one of X 4 and X 5 represents a nitrogen atom.
  • X 6 to X 11 are an element group forming an aromatic 5-membered ring or an aromatic 6-membered ring, and are selected from a carbon atom or a nitrogen atom. However, when X 6 to X 11 form an aromatic 5-membered ring, X 11 represents a simple bond.
  • a display device comprising the organic electroluminescence element is provided.
  • a lighting device comprising the organic electroluminescence element.
  • an organic electroluminescence element that exhibits high light emission efficiency, has a long light emission lifetime, and can suppress an increase in voltage during driving, and an illumination device and a display device including the element.
  • an organic electroluminescence device that has high luminous efficiency and a long half-life, and can suppress an increase in voltage during driving.
  • a display device and a lighting device including the organic electroluminescence element can be provided.
  • the light emitting layer unit may have a non-light emitting intermediate layer between a plurality of light emitting layers, and may have a multi-photon unit configuration in which the intermediate layer is a charge generation layer.
  • the charge generation layer includes ITO (indium tin oxide), IZO (indium zinc oxide), ZnO 2 , TiN, ZrN, HfN, TiO x , VO x , CuI, InN, GaN, CuAlO 2.
  • the light emitting layer in the organic EL element of the present invention is preferably a white light emitting layer, and an illumination device using these is preferable.
  • the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is in the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.
  • the total film thickness of the light emitting layer is not particularly limited, but from the viewpoint of improving the uniformity of the film, preventing unnecessary application of high voltage during light emission, and improving the stability of the emission color with respect to the drive current. It is preferably adjusted to a range of 2 nm to 5 ⁇ m, more preferably adjusted to a range of 2 nm to 200 nm, and particularly preferably a range of 5 nm to 100 nm.
  • a light-emitting dopant or a host compound which will be described later, is used. And the like can be formed by a method, an inkjet method, a printing method, a spray coating method, a curtain coating method, an LB method (Langmuir Brodgett method, etc.).
  • a hexadentate ortho metal iridium complex based on this invention it is preferable to form into a film by a wet process.
  • the light emitting layer of the organic EL device of the present invention contains a light emitting dopant (phosphorescent dopant (also referred to as phosphorescent dopant, phosphorescent dopant group) or fluorescent dopant) compound and a light emitting host compound. Is preferred.
  • a light emitting dopant phosphorescent dopant (also referred to as phosphorescent dopant, phosphorescent dopant group) or fluorescent dopant) compound and a light emitting host compound. Is preferred.
  • Luminescent dopant compound A luminescent dopant compound (a luminescent dopant, also simply referred to as a dopant) will be described.
  • a fluorescent dopant also referred to as a fluorescent compound
  • a phosphorescent dopant also referred to as a phosphorescent emitter, a phosphorescent compound, a phosphorescent compound, or the like
  • a fluorescent dopant also referred to as a fluorescent compound
  • a phosphorescent dopant also referred to as a phosphorescent emitter, a phosphorescent compound, a phosphorescent compound, or the like
  • the phosphorescent dopant according to the present invention is a compound in which light emission from an excited triplet is observed, specifically, a compound that emits phosphorescence at room temperature (25 ° C.), and has a phosphorescence quantum yield of 25. Although it is defined as a compound of 0.01 or more at ° C., a preferable phosphorescence quantum yield is 0.1 or more.
  • the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence dopant according to the present invention achieves the phosphorescence quantum yield (0.01 or more) in any solvent. That's fine.
  • the phosphorescent dopant There are two types of light emission of the phosphorescent dopant in principle. One is the recombination of carriers on the host compound to which carriers are transported to generate an excited state of the luminescent host compound, and this energy is used as the phosphorescent dopant. It is an energy transfer type in which light emission from a phosphorescent dopant is obtained by moving to. The other is a carrier trap type in which a phosphorescent dopant serves as a carrier trap, carrier recombination occurs on the phosphorescent dopant, and light emission from the phosphorescent dopant compound is obtained. In any case, it is a condition that the excited state energy of the phosphorescent dopant is lower than the excited state energy of the host compound.
  • At least one of the light-emitting layers contains a phosphorescent organometallic complex (also referred to as a phosphorescent dopant or a phosphorescent dopant).
  • a phosphorescent organometallic complex also referred to as a phosphorescent dopant or a phosphorescent dopant.
  • a hexadentate ortho metal iridium complex represented by the general formula (I), which is an organic EL device material according to the present invention.
  • an ortho metal iridium complex having a 5-membered ring as a component of the ligand can emit light at a shorter wavelength than a phenylpyridine-based ortho metal iridium complex composed of only a 6-membered ring, but is still practical. Possible device lifetime and high luminous efficiency have not been achieved.
  • a complex in which a plurality of ligands constituting the iridium complex are connected to each other is known, and these have improved thermal stability by connecting a plurality of ligands to each other.
  • the device life is improved.
  • the iridium complex becomes rigid, and the stability of the excited state, radical anion, and radical cation decreases. Therefore, it has been found that by making the iridium complex into a structure represented by the general formula (I) according to the present invention, both the thermal stability and the stability of the excited state, radical anion, and radical cation can be improved. It was. Furthermore, as a result, it has been found that the device life of the organic EL device can be improved and the voltage rise during driving can be suppressed.
  • the orthometaliridium complex according to the present invention will be described.
  • the ortho metal iridium complex according to the present invention can be used in any one of the constituent layers of the organic EL device of the present invention, but the effect of the present invention (the light emission efficiency of the device (specifically, the external extraction quantum efficiency, simply From the viewpoint of sufficiently improving efficiency), increasing half-life, and reducing driving voltage), it is used as a light-emitting dopant (also simply referred to as a dopant) in the light-emitting layer of an organic EL device and further in the light-emitting layer. It is preferable.
  • the ortho metal iridium complex of the present invention is specifically represented by the following general formula (I).
  • V represents a divalent linking group and is covalently bonded to L 2 and L 3 to form an Ir multidentate ligand, and preferably represents the following structure.
  • * represents a bonding site with L 2 and L 3
  • n represents 1 or 2
  • R represents a hydrogen atom, an alkyl group, an aryl group, or an aromatic heterocyclic group.
  • L 1 to L 3 are each represented by the following general formula (II), and X 5 and Ir in the general formula (II) form a coordination bond, and X in the general formula (II) 7 and Ir form a covalent bond. Note that L 1 to L 3 may have the same structure or different structures.
  • X 1 to X 5 are an element group forming a nitrogen-containing heterocyclic ring, selected from a carbon atom or a nitrogen atom, and at least one of X 4 and X 5 represents a nitrogen atom.
  • the nitrogen-containing heterocycle represented by X 1 to X 5 is preferably an imidazole, pyrazole, or triazole ring, and more preferably an imidazole ring.
  • X 6 to X 11 are an element group forming an aromatic 5-membered ring or an aromatic 6-membered ring, and are selected from a carbon atom or a nitrogen atom. However, when X 6 to X 11 form an aromatic 5-membered ring, X 11 represents a simple bond.
  • the aromatic 5-membered ring represented by X 6 to X 11 is preferably a thiophene ring, an imidazole ring, a pyrazole ring or a triazole ring.
  • the aromatic 6-membered ring represented by X 6 to X 11 is preferably a benzene ring or a pyridine ring, and more preferably a benzene ring.
  • the aromatic 5-membered ring or aromatic 6-membered ring represented by X 6 to X 11 may further have a substituent, and these substituents are bonded to form a condensed ring. It may be formed.
  • substituents include an alkyl group (for example, methyl group, ethyl group, trifluoromethyl group, isopropyl group), an alkoxy group (for example, methoxy group, ethoxy group, etc.), a halogen atom (for example, fluorine atom), cyano Group, nitro group, dialkylamino group (for example, dimethylamino group, etc.), trialkylsilyl group (for example, trimethylsilyl group, etc.), triarylsilyl group (for example, triphenylsilyl group, etc.), triheteroarylsilyl group (for example, Such as a tripyridylsilyl group), a benzyl group, an aryl group (eg, a phenyl group), a heteroaryl group (eg, a pyridyl group, a carbazolyl group, etc.), and the condensed ring includes 9,9'-dimethylfluoren
  • General formula (II) is preferably represented by the following general formula (III).
  • R 1 represents an aryl group.
  • examples of the aryl group represented by R 1 include a phenyl group, a naphthyl group, a biphenyl group, and a terphenyl group, and a phenyl group is preferable.
  • Examples of the substituent substituted on the phenyl group include an alkyl group (for example, a methyl group, an ethyl group, a trifluoromethyl group, and an isopropyl group), an alkoxy group (for example, a methoxy group and an ethoxy group), and a halogen atom (for example, fluorine Atoms, etc.), cyano groups, nitro groups, dialkylamino groups (eg, dimethylamino groups, etc.), trialkylsilyl groups (eg, trimethylsilyl, etc.), triarylsilyl groups (eg, triphenylsilyl groups, etc.), triheteroaryls Examples include silyl groups (for example, tripyridylsilyl group), benzyl groups, aryl groups (for example, phenyl group), heteroaryl groups (for example, pyridyl group, carbazolyl group, etc.), preferably alkyl groups, aryl
  • R 2 and R 3 each represent a hydrogen atom or a substituent.
  • the substituent represented by R 2 and R 3 has an aromatic 5-membered ring or an aromatic 6-membered ring represented by X 6 to X 11 in the general formula (II). The thing similar to the substituent which you may have is mentioned.
  • the general formula (II) is preferably represented by the following general formula (IV).
  • R 1 represents an aryl group.
  • examples of the aryl group represented by R 1 include the same aryl groups represented by R 1 in the general formula (III).
  • R 2 and R 3 each represent a hydrogen atom or a substituent.
  • the substituent represented by R 2 and R 3 has an aromatic 5-membered ring or an aromatic 6-membered ring represented by X 6 to X 11 in the general formula (II). The thing similar to the substituent which you may have is mentioned.
  • the general formula (II) is preferably represented by the following general formula (V).
  • R 1 represents an aryl group.
  • the aryl group represented by R 1 those in the general formula (III) the same as the aryl group represented by R 1 can be mentioned.
  • R 2 and R 3 each represent a hydrogen atom or a substituent.
  • the substituent represented by R 2 and R 3 has an aromatic 5-membered ring or an aromatic 6-membered ring represented by X 6 to X 11 in the general formula (II). The thing similar to the substituent which you may have is mentioned.
  • the general formula (II) is preferably represented by the following general formula (VI).
  • R 1 represents an aryl group.
  • examples of the aryl group represented by R 1 include the same aryl groups represented by R 1 in the general formula (III).
  • R ⁇ 2 > represents a hydrogen atom or a substituent respectively.
  • the substituent represented by R 2 may have an aromatic 5-membered ring or an aromatic 6-membered ring represented by X 6 to X 11 in the general formula (II). The thing similar to a good substituent is mentioned.
  • the general formula (II) is preferably represented by the following general formula (VII).
  • R 1 represents an aryl group.
  • examples of the aryl group represented by R 1 include the same aryl groups represented by R 1 in the general formula (III).
  • R 2 is each a hydrogen atom or a substituent.
  • the substituent represented by R 2 may be an aromatic 5-membered ring or an aromatic 6-membered ring represented by X 6 to X 11 in the general formula (II). The thing similar to a good substituent is mentioned.
  • Japanese Patent Laid-Open No. 2002-24175 No. 1 JP-A No. 2001-319779, JP-A No. 2001-319780, JP-A No. 2002-62824, JP-A No. 2002-1000047, JP-A No. 2002-203679, JP-A No. 2002-343572 JP-A-2002-203678.
  • the organic layer was dried over magnesium sulfate, and after removal, the solvent was concentrated and purified by silica gel column chromatography to obtain 2.0 g of ligand A1.
  • a precursor was obtained.
  • the structure of the precursor of ligand A1 was confirmed by mass spectrum and 1 H-NMR.
  • Step 6 Under a nitrogen atmosphere, 350 mg of the ligand A1 obtained in Step 5, 150 mg of the ligand A2, 263 mg of tris (acetylacetonato) iridium (III), 35 ml of ethylene glycol and 10 ml of glycerin were added and heated at an internal temperature of 160 ° C. for 15 hours. The reaction solution was returned to room temperature, diluted with 50 ml of methanol, and the precipitate was collected by filtration. Further, the obtained precipitate was washed with methanol and dried to obtain 110 mg of Compound Example (III) -2. The structure of Compound Example (III) -2 was confirmed by mass spectrum and 1 H-NMR.
  • Fluorescent dopant also called fluorescent compound
  • fluorescent dopants coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes, stilbene dyes , Polythiophene dyes, rare earth complex phosphors, and the like, and compounds having a high fluorescence quantum yield such as laser dyes.
  • the luminescent dopant according to the present invention may be used in combination of a plurality of compounds, and combinations of phosphorescent dopants having different structures, phosphorescent dopants and fluorescence.
  • a combination of dopants may be used.
  • the specific example of the conventionally well-known light emission dopant which may be used in combination with the metal complex represented with general formula (I) based on this invention as a light emission dopant is given, this invention is not limited to these.
  • Luminescent host compound (also referred to as luminescent host)
  • the host compound has a mass ratio of 20% or more in the layer, and the phosphorescence quantum yield of phosphorescence emission is 0 at room temperature (25 ° C.). Defined as less than 1 compound.
  • the phosphorescence quantum yield is preferably less than 0.01.
  • the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.
  • the light-emitting host that can be used in the present invention is not particularly limited, and compounds conventionally used in organic EL devices can be used.
  • a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of light from being increased in wavelength, and has a high Tg (glass transition temperature) is preferable.
  • a conventionally known light-emitting host may be used alone, or a plurality of types may be used in combination.
  • the movement of charges can be adjusted, and the organic EL element can be made highly efficient.
  • it becomes possible to mix different light emission by using multiple types of the metal complex of this invention used as said phosphorescence dopant, and / or a conventionally well-known compound, and, thereby, arbitrary luminescent colors can be obtained.
  • the light emitting host used in the present invention may be a low molecular compound, a high molecular compound having a repeating unit, or a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (polymerizable light emitting host). Of course, one or more of such compounds may be used.
  • a compound represented by the following general formula (B) is particularly preferable as the light emitting host of the light emitting layer of the organic EL device of the present invention.
  • Xa represents O or S
  • Xb, Xc, Xd, and Xe each represents a hydrogen atom, a substituent, or a group represented by the following general formula (C)
  • Xb, Xc, Xd , Xe represents a group represented by the following general formula (C)
  • at least one of the groups represented by the general formula (C) represents Ar as a carbazolyl group.
  • L 4 represents a divalent linking group derived from an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • n represents 0 or an integer of 1 to 3, and when n is 2 or more, the plurality of L 4 may be the same or different.
  • * represents a linking site with the general formula (B).
  • Ar represents a group represented by the following general formula (D).
  • Xf represents N (R ′′), O or S
  • E 1 to E 8 represent C (R ′′ 1 ) or N
  • R ′′ and R ′′ 1 are hydrogen atoms, substituents or it represents a linking site with L 4. * Represents a linking site of the L 4.
  • a compound represented by the following general formula (B ′) is particularly preferably used as a light-emitting host of the light-emitting layer of the organic EL device of the present invention.
  • Xa represents O or S
  • Xb and Xc each represents a substituent or a group represented by the above general formula (C)
  • at least one of Xb and Xc is the above
  • Ar represents a carbazolyl group in at least one of the groups represented by the formula (C).
  • At least one of Xb and Xc is represented by the general formula (C), and more preferably, Ar in the general formula (C) has a substituent. It represents a carbazolyl group which may have, and more preferably represents a carbazolyl group linked to L 4 at the N-position where Ar in the general formula (C) may have a substituent.
  • the compound represented by the general formula (B ′) that is preferably used as the host compound (also referred to as a light-emitting host) of the light-emitting layer of the organic EL device of the present invention is specifically a specific example that is previously used as a light-emitting host. OC-9, OC-11, OC-12, OC-14, OC-18, OC-18, OC-29, OC-30, OC-31, and OC-32 mentioned above, but the present invention is not limited thereto. .
  • the electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • the electron transport layer can be provided with a single layer or a plurality of layers.
  • the electron transport layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer.
  • any conventionally known compound may be selected and used in combination. Is possible.
  • electron transport materials examples include polycyclic aromatic hydrocarbons such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, Ring tetracarboxylic anhydride, carbodiimide, fluorenylidenemethane derivative, anthraquinodimethane and anthrone derivative, oxadiazole derivative, carboline derivative, or at least carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative Derivatives having a ring structure, one of which is substituted with a nitrogen atom, hexaazatriphenylene derivatives and the like.
  • polycyclic aromatic hydrocarbons such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, Ring tetracarboxylic anhydride, carbod
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, or a quinoxaline derivative having a quinoxaline ring known as an electron-withdrawing group can also be used as an electron transport material. It is also possible to use a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain.
  • metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and the like, and the central metals of these metal complexes are In, Mg, Metal complexes replaced with Cu, Ca, Sn, Ga or Pb can also be used as the electron transport material.
  • metal-free or metal phthalocyanine, or those having terminal ends substituted with an alkyl group or a sulfonic acid group can also be used as the electron transport material.
  • An inorganic semiconductor such as n-type-Si and n-type-SiC can also be used as an electron transport material.
  • the electron transport layer is made of an electron transport material such as a vacuum deposition method, a wet method (also referred to as a wet process, such as a spin coating method, a casting method, a die coating method, a blade coating method, a roll coating method, an ink jet method, a printing method, or a spraying method.
  • the film is preferably formed by thinning by a coating method, curtain coating method, LB method (Langmuir Brodgett method, etc.).
  • the film thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5000 nm, preferably 5 nm to 200 nm.
  • This electron transport layer may have a single layer structure composed of one or more of the above materials.
  • an n-type dopant such as a metal compound such as a metal complex or a metal halide may be doped.
  • cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 nm to 200 nm.
  • a transparent or semi-transparent cathode can be produced by producing the above metal on the cathode in a thickness of 1 nm to 20 nm and then producing a conductive transparent material mentioned in the explanation of the anode described later. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
  • Injection layer electron injection layer (cathode buffer layer), hole injection layer >> The injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, and as described above, it exists between the anode and the light emitting layer or the hole transport layer and between the cathode and the light emitting layer or the electron transport layer. May be.
  • An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance.
  • Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) ) ”, Chapter 2,“ Electrode Materials ”(pages 123 to 166), which has a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
  • anode buffer layer hole injection layer
  • copper phthalocyanine is used.
  • cathode buffer layer (electron injection layer) The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc.
  • Metal buffer layer typified by, alkali metal compound buffer layer typified by lithium fluoride and potassium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride and cesium fluoride, typified by aluminum oxide Examples thereof include an oxide buffer layer.
  • the buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 ⁇ m, although it depends on the material.
  • ⁇ Blocking layer hole blocking layer, electron blocking layer>
  • the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A Nos. 11-204258 and 11-204359, and “Organic EL elements and the forefront of industrialization (published by NTT Corporation on November 30, 1998)” on page 237. There is a hole blocking (hole blocking) layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the structure of the electron transport layer described above can be used as a hole blocking layer according to the present invention, if necessary.
  • the hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
  • the hole blocking layer includes a carbazole derivative, a carboline derivative, a diazacarbazole derivative (the diazacarbazole derivative is a nitrogen atom in which any one of carbon atoms constituting the carboline ring is mentioned as the host compound described above. It is preferable to contain (represented by).
  • the light emitting layer having the shortest wavelength of light emission is preferably closest to the anode among all the light emitting layers.
  • 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer.
  • the ionization potential is defined by the energy required to emit electrons at the HOMO (highest occupied orbital) level of the compound to the vacuum level, and can be determined by, for example, the following method.
  • Gaussian 98 Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.
  • a molecular orbital calculation software manufactured by Gaussian, USA.
  • eV unit converted value As a value (eV unit converted value) calculated by performing structure optimization using B3LYP / 6-31G *. This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
  • the ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy. For example, a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd. or a method known as ultraviolet photoelectron spectroscopy can be suitably used.
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved.
  • the structure of the hole transport layer described later can be used as an electron blocking layer as necessary.
  • the film thickness of the hole blocking layer and the electron transport layer according to the present invention is preferably 3 nm to 100 nm, and more preferably 5 nm to 30 nm.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has any one of hole injection or transport and electron barrier properties, and may be either organic or inorganic.
  • triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • azatriphenylene derivatives such as those described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as hole transport materials.
  • the above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl; N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminoph
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
  • JP-A-11-251067 J. Org. Huang et. al.
  • a so-called p-type hole transport material described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used.
  • these materials are preferably used because a light-emitting element with higher efficiency can be obtained.
  • the hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can.
  • the thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • the hole transport layer may have a single layer structure composed of one or more of the above materials.
  • a hole transport layer having a high p property doped with impurities can be used.
  • examples thereof include JP-A-4-297076, JP-A-2000-196140, and JP-A-2001-102175. Appl. Phys. 95, 5773 (2004), and the like.
  • anode As the anode in the organic EL element, an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such electrode substances include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
  • these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not so high (about 100 ⁇ m or more)
  • a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
  • a wet film forming method such as a printing method or a coating method can be used.
  • the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, it is usually selected in the range of 10 nm to 1000 nm, preferably 10 nm to 200 nm.
  • a support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention, there is no particular limitation on the type of glass, plastic, etc., and it is transparent. May be opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.
  • polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfone , Polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylates, cyclone resins such as Arton (trade name JSR) or Appel (trade name Mits
  • an inorganic film, an organic film or a hybrid film of both may be formed on the surface of the resin film.
  • the water vapor permeability (25 ⁇ 0.5 ° C.) measured by a method according to JIS K 7129-1992. , Relative humidity (90 ⁇ 2)% RH) is preferably 0.01 g / (m 2 ⁇ 24 h) or less, and further, oxygen measured by a method according to JIS K 7126-1987.
  • a high barrier film having a permeability of 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less and a water vapor permeability of 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less is preferable.
  • the material for forming the barrier film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
  • the method for forming the barrier film is not particularly limited.
  • the vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma weight A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, and the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.
  • the opaque support substrate examples include metal plates such as aluminum and stainless steel, films, opaque resin substrates, ceramic substrates, and the like.
  • the external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, and more preferably 5% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element ⁇ 100.
  • a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination.
  • the ⁇ max of light emission of the organic EL element is preferably 480 nm or less.
  • a thin film made of a desired electrode material for example, an anode material, is formed on a suitable substrate so as to have a thickness of 1 ⁇ m or less, preferably 10 nm to 200 nm, and an anode is manufactured.
  • a thin film containing an organic compound such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, or a cathode buffer layer, which is an element material, is formed thereon.
  • the thin film can be formed by a vacuum deposition method, a wet method (also referred to as a wet process), or the like.
  • Wet methods include spin coating, casting, die coating, blade coating, roll coating, ink jet, printing, spray coating, curtain coating, and LB, but precise thin films can be formed.
  • a method having high suitability for a roll-to-roll method such as a die coating method, a roll coating method, an ink jet method, and a spray coating method is preferable. Different film formation methods may be applied for each layer.
  • liquid medium for dissolving or dispersing the organic EL material according to the present invention examples include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, and mesitylene.
  • Aromatic hydrocarbons such as cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, and organic solvents such as DMF and DMSO can be used.
  • a dispersion method it can disperse
  • a thin film made of a cathode material is formed thereon so as to have a thickness of 1 ⁇ m or less, preferably in the range of 50 to 200 nm, and a desired organic EL device can be obtained by providing a cathode. .
  • the cathode, cathode buffer layer, electron transport layer, hole blocking layer, light emitting layer, hole transport layer, hole injection layer, and anode can be formed in the reverse order.
  • the organic EL device of the present invention it is preferable to produce from the hole injection layer to the cathode consistently by a single evacuation, but it may be taken out halfway and subjected to different film forming methods. At that time, it is preferable to perform the work in a dry inert gas atmosphere.
  • ⁇ Sealing> As a sealing means used for this invention, the method of adhere
  • the sealing member may be disposed so as to cover the display area of the organic EL element, and may be a concave plate shape or a flat plate shape. Further, transparency and electrical insulation are not particularly limited.
  • Specific examples include a glass plate, a polymer plate / film, and a metal plate / film.
  • the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the polymer plate include those formed from polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like.
  • Examples of the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
  • a polymer film and a metal film can be preferably used because the element can be thinned.
  • the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 ⁇ 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less, and a method according to JIS K 7129-1992. It is preferable that the water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH) measured in (1) is 1 ⁇ 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less.
  • sealing member For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.
  • the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to.
  • hot-melt type polyamide, polyester, and polyolefin can be mentioned.
  • a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
  • an organic EL element may deteriorate by heat processing, what can be adhesively cured from room temperature to 80 ° C. is preferable.
  • a desiccant may be dispersed in the adhesive.
  • coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.
  • the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film.
  • the material for forming the film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
  • vacuum deposition sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma
  • a polymerization method a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil
  • a vacuum is also possible.
  • a hygroscopic compound can also be enclosed inside.
  • hygroscopic compound examples include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
  • metal oxides for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
  • sulfates for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate.
  • metal halides eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.
  • perchloric acids eg perchloric acid Barium, magnesium perchlorate, and the like
  • anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.
  • a protective film or a protective plate may be provided on the outer side of the sealing film on the side facing the support substrate with the organic layer interposed therebetween or on the sealing film.
  • the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, and the like used for the sealing can be used, but the polymer film is light and thin. Is preferably used.
  • the organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said. This is because light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light undergoes total reflection between the light and the light, and the light is guided through the transparent electrode or the light emitting layer.
  • a method of improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate and preventing total reflection at the transparent substrate and the air interface (US Pat. No. 4,774,435), A method for improving efficiency by giving light condensing property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method of forming a reflective surface on the side surface of an element (Japanese Patent Laid-Open No. 1-220394), light emission from a substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the bodies (Japanese Patent Laid-Open No.
  • these methods can be used in combination with the organic EL device of the present invention.
  • a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, transparent A method of forming a diffraction grating between any layers of the electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
  • the low refractive index layer examples include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less.
  • the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave that has exuded by evanescent enters the substrate.
  • the method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency.
  • This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction.
  • Light that cannot be emitted due to total internal reflection between layers is diffracted by introducing a diffraction grating in any layer or medium (in a transparent substrate or transparent electrode), and the light is removed. I want to take it out.
  • the diffraction grating to be introduced has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much.
  • the refractive index distribution a two-dimensional distribution
  • the light traveling in all directions is diffracted, and the light extraction efficiency is increased.
  • the position where the diffraction grating is introduced may be in any of the layers or in the medium (in the transparent substrate or the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.
  • the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium.
  • the arrangement of the diffraction grating is preferably two-dimensionally repeated such as a square lattice, a triangular lattice, or a honeycomb lattice.
  • the organic EL device of the present invention is processed on the light extraction side of the substrate so as to provide, for example, a microlens array structure, or combined with a so-called condensing sheet, for example, with respect to a specific direction, for example, the device light emitting surface.
  • a specific direction for example, the device light emitting surface.
  • quadrangular pyramids having a side of 30 ⁇ m and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate.
  • One side is preferably 10 ⁇ m to 100 ⁇ m. If it becomes smaller than this, the effect of diffraction will generate
  • the condensing sheet for example, a sheet that has been put into practical use for an LED backlight of a liquid crystal display device can be used.
  • a sheet for example, a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
  • BEF brightness enhancement film
  • the shape of the prism sheet for example, the base material may be formed with a triangle stripe having a vertex angle of 90 degrees and a pitch of 50 ⁇ m, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.
  • a light diffusion plate / film may be used in combination with the light collecting sheet.
  • a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.
  • the organic EL element of the present invention can be used as a display device, a display, and various light emission sources.
  • lighting devices home lighting, interior lighting
  • clock and liquid crystal backlights billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light
  • the light source of a sensor etc. are mentioned, It is not limited to this, It can use effectively for the use as a backlight of a liquid crystal display device, and an illumination light source especially.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like during film formation, if necessary.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned.
  • a conventionally known method is used. Can do.
  • the light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with a total of CS-1000 (manufactured by Konica Minolta Sensing Co., Ltd.) is applied to the CIE chromaticity coordinates.
  • the display device of the present invention comprises the organic EL element of the present invention.
  • the display device of the present invention may be single color or multicolor, the multicolor display device will be described here.
  • a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by vapor deposition, casting, spin coating, ink jet, printing, or the like.
  • the method is not limited. However, the vapor deposition method, the ink jet method, the spin coating method, and the printing method are preferable.
  • the configuration of the organic EL element included in the display device is selected from the above-described configuration examples of the organic EL element as necessary.
  • the manufacturing method of an organic EL element is as having shown in the one aspect
  • a DC voltage When a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 V to 40 V with the positive polarity of the anode and the negative polarity of the cathode. Further, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the-state.
  • the alternating current waveform to be applied may be arbitrary.
  • the multicolor display device can be used as a display device, a display, and various light sources.
  • a display device or display full-color display is possible by using three types of organic EL elements of blue, red, and green light emission.
  • Display devices and displays include televisions, personal computers, mobile devices, AV devices, teletext displays, information displays in automobiles, and the like. In particular, it may be used as a display device for reproducing still images and moving images, and the driving method when used as a display device for reproducing moving images may be either a simple matrix (passive matrix) method or an active matrix method.
  • Light sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, light sources for optical sensors, etc.
  • the present invention is not limited to these examples.
  • FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements. It is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.
  • the display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
  • the control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside, and the pixels for each scanning line respond to the image data signal by the scanning signal.
  • the image information is sequentially emitted to scan the image and display the image information on the display unit A.
  • FIG. 2 is a schematic diagram of the display unit A.
  • the display unit A includes a wiring unit including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3 and the like on a substrate.
  • the main members of the display unit A will be described below.
  • FIG. 2 shows a case where the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).
  • the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions (details are illustrated). Not) When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6 and emits light according to the received image data. Full-color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.
  • FIG. 3 is a schematic diagram of a pixel.
  • the pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like.
  • a full color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 in a plurality of pixels, and juxtaposing them on the same substrate.
  • an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6.
  • a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5
  • the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is supplied to the capacitor 13 and the driving transistor 12. Is transmitted to the gate.
  • the capacitor 13 is charged according to the potential of the image data signal, and the drive transistor 12 is turned on.
  • the drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10.
  • the power supply line 7 connects the organic EL element 10 to the potential of the image data signal applied to the gate. Current is supplied.
  • the driving of the switching transistor 11 is turned off.
  • the driving of the driving transistor 12 is kept on and the next scanning signal is applied. Until then, the light emission of the organic EL element 10 continues.
  • the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
  • the organic EL element 10 emits light by the switching transistor 11 and the drive transistor 12 that are active elements for the organic EL elements 10 of the plurality of pixels, and the organic EL elements 10 of the plurality of pixels 3 emit light. It is carried out.
  • Such a light emitting method is called an active matrix method.
  • the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or by turning on / off a predetermined light emission amount by a binary image data signal. Good.
  • the potential of the capacitor 13 may be held continuously until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
  • a passive matrix light emission drive in which the organic EL element emits light according to the data signal only when the scanning signal is scanned.
  • FIG. 4 is a schematic diagram of a passive matrix display device.
  • a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
  • the scanning signal of the scanning line 5 is applied by sequential scanning, the pixels 3 connected to the applied scanning line 5 emit light according to the image data signal.
  • the pixel 3 has no active element, and the manufacturing cost can be reduced.
  • the lighting device of the present invention has the said organic EL element.
  • the organic EL element of the present invention may be used as an organic EL element having a resonator structure.
  • the purpose of use of the organic EL element having such a resonator structure is as follows.
  • the light source of a machine, the light source of an optical communication processing machine, the light source of an optical sensor, etc. are mentioned, However It is not limited to these. Moreover, you may use for the said use by making a laser oscillation.
  • the organic EL element of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a device (display).
  • the driving method when used as a display device for moving image reproduction may be either a simple matrix (passive matrix) method or an active matrix method.
  • a full color display device can be produced by using two or more organic EL elements of the present invention having different emission colors.
  • the organic EL material of the present invention can be applied to an organic EL element that emits substantially white light as a lighting device.
  • a plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials to obtain white light emission by color mixing.
  • the combination of a plurality of emission colors may include three emission maximum wavelengths of the three primary colors of red, green and blue, or two using the complementary colors such as blue and yellow, blue green and orange.
  • the thing containing the light emission maximum wavelength may be used.
  • a combination of light emitting materials for obtaining a plurality of emission colors is a combination of a plurality of phosphorescent or fluorescent materials, a light emitting material that emits fluorescence or phosphorescence, and light from the light emitting material as excitation light. Any of those combined with a dye material that emits light may be used, but in the white organic EL device according to the present invention, only a combination of a plurality of light-emitting dopants may be mixed.
  • an electrode film can be formed by a vapor deposition method, a cast method, a spin coating method, an ink jet method, a printing method, etc., and productivity is also improved. According to this method, unlike the white organic EL device in which light emitting elements of a plurality of colors are arranged in parallel in an array, the elements themselves are luminescent white.
  • a luminescent material used for a light emitting layer For example, if it is a backlight in a liquid crystal display element, the metal complex which concerns on this invention so that it may suit the wavelength range corresponding to CF (color filter) characteristic, Any one of known light emitting materials may be selected and combined to be whitened.
  • CF color filter
  • One aspect of the lighting device of the present invention that includes the organic EL element of the present invention will be described.
  • the non-light-emitting surface of the organic EL device of the present invention is covered with a glass case, a glass substrate having a thickness of 300 ⁇ m is used as a sealing substrate, and an epoxy-based photocurable adhesive (LUX TRACK manufactured by Toagosei Co., Ltd.) is used as a sealing material around.
  • LC0629B is applied, and this is overlaid on the cathode and brought into close contact with the transparent support substrate, irradiated with UV light from the glass substrate side, cured and sealed, and as shown in FIG. 5 and FIG. Can be formed.
  • FIG. 5 shows a schematic diagram of a lighting device, and the organic EL element 101 of the present invention is covered with a glass cover 102 (in addition, the sealing operation with the glass cover is to bring the organic EL element 101 into contact with the atmosphere. And a glove box under a nitrogen atmosphere (in an atmosphere of high-purity nitrogen gas having a purity of 99.999% or more).
  • FIG. 6 shows a cross-sectional view of the lighting device.
  • 105 denotes a cathode
  • 106 denotes an organic EL layer
  • 107 denotes a glass substrate with a transparent electrode.
  • the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
  • a poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) diluted to 70% with pure water was used to spin. After forming a thin film by the coating method, it was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 30 nm.
  • a hole transport material Poly N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl)) benzidine (manufactured by American Dye Source, ADS- A thin film was formed by spin coating using the chlorobenzene solution of No. 254). It heat-dried at 150 degreeC for 1 hour, and provided the 2nd hole transport layer with a film thickness of 40 nm.
  • a thin film was formed by spin coating using a 1-butanol solution of ET-11 as an electron transport material, and an electron transport layer having a thickness of 20 nm was provided.
  • This substrate was attached to a vacuum deposition apparatus, and the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa.
  • 1.0 nm of lithium fluoride was deposited as an electron injection layer and 110 nm of aluminum was deposited as a cathode, thereby fabricating an organic EL device 1-1.
  • the organic EL elements 1-2 to 1-12 of the present invention show higher efficiency than the organic EL element 1-1 of the comparative example, the half-life is improved, and the voltage rise during driving is suppressed. It can be seen that the characteristics as an element are improved.
  • External extraction quantum efficiency (also simply referred to as efficiency) The same procedure as described in Example 1 was performed.
  • the external extraction quantum efficiency was expressed as a relative value with the organic EL element 2-1 (comparative example) as 100.
  • the organic EL elements 2-2 to 2-8 of the present invention produced using the hexadentate orthometal iridium complex according to the present invention compared to the organic EL element 2-1 of the comparative example are as follows: It is clear that the characteristics of the device are improved, such as high efficiency for each, and suppression of dark spots and voltage rise.
  • ⁇ Preparation of organic EL element 3-1 A transparent substrate provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) as an anode on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm.
  • the supporting substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.
  • PEDOT / PSS polystyrene sulfonate
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of ⁇ -NPD is placed in a molybdenum resistance heating boat as a hole transport material and OC-as a host compound in another molybdenum resistance heating boat.
  • 200 mg of 30 was put, 200 mg of ET-8 as an electron transport material was put in another resistance heating boat made of molybdenum, and 100 mg of Comparative 1 was put as a dopant compound in another resistance heating boat made of molybdenum, and attached to a vacuum deposition apparatus.
  • the pressure in the vacuum chamber was reduced to 4 ⁇ 10 ⁇ 4 Pa, and the heating boat containing ⁇ -NPD was energized and heated, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second.
  • the second hole transport layer was provided.
  • the heating boat containing OC-30 as a host compound and Comparative Example 1 as a dopant compound was energized and heated, and on the second hole transport layer at a deposition rate of 0.1 nm / second and 0.006 nm / second, respectively.
  • a light emitting layer having a thickness of 40 nm was provided by co-evaporation.
  • the heating boat containing ET-8 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride was vapor-deposited to form a cathode buffer layer having a thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a thickness of 110 nm.
  • an organic EL element 3-1 was produced.
  • External extraction quantum efficiency (also simply referred to as efficiency) The same procedure as described in Example 1 was performed.
  • the external extraction quantum efficiency was expressed as a relative value with the organic EL element 3-1 (comparative example) as 100.
  • the organic EL elements 3-3 to 3-13 of the present invention were compared with the organic EL elements 3-1 and 3-2 of the comparative example. It can be seen that the characteristics as an element are improved, such as high light emission luminance and suppression of voltage increase during driving.
  • a poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) diluted to 70% with pure water was used to spin. After forming a thin film by the coating method, it was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 30 nm.
  • a hole transport material Poly N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl)) benzidine (manufactured by American Dye Source, ADS- A thin film was formed by spin coating using the chlorobenzene solution of No. 254). It heat-dried at 150 degreeC for 1 hour, and provided the 2nd hole transport layer with a film thickness of 40 nm.
  • a solution prepared by dissolving OC-11 (100 mg) as a host compound and Compound Example (III) -25 (16 mg) as a dopant compound in 6 ml of hexafluoroisopropanol (HFIP) was used, and at 2000 rpm, A thin film was formed by spin coating under conditions of 30 seconds and vacuum dried at 60 ° C. for 1 hour to form a second light emitting layer.
  • This substrate is fixed to a substrate holder of a vacuum deposition apparatus, the vacuum chamber is depressurized to 4 ⁇ 10 ⁇ 4 Pa, and then ET-9 is deposited on the second light emitting layer to form an electron transport layer having a thickness of 30 nm. Subsequently, lithium fluoride was vapor-deposited to form a cathode buffer layer having a thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a thickness of 110 nm. Thus, an organic EL element 4-1 was produced. .
  • a poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) diluted to 70% with pure water was used to spin. After forming a thin film by the coating method, it was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 30 nm.
  • a hole transport material Poly N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl)) benzidine (manufactured by American Dye Source, ADS- A thin film was formed by spin coating using the chlorobenzene solution of No. 254). It heat-dried at 150 degreeC for 1 hour, and provided the 2nd hole transport layer with a film thickness of 40 nm.
  • This substrate was fixed to a substrate holder of a vacuum deposition apparatus, and the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa, and then ET-15 was deposited on the light emitting layer to form an electron transport layer having a thickness of 30 nm. Subsequently, lithium fluoride was vapor-deposited to form a cathode buffer layer having a thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a thickness of 110 nm. Thus, an organic EL element 5-1 was produced.
  • Preparation of white light-emitting organic EL element 6-1 A transparent substrate provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) as an anode on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm.
  • the supporting substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of ⁇ -NPD is added as a hole transport material to a molybdenum resistance heating boat, and compound 9 as a host compound is added to another molybdenum resistance heating boat.
  • each of the heating boats containing ⁇ -NPD was separately energized and deposited on the transparent support substrate at a deposition rate of 0.1 nm / sec.
  • a first hole transport layer was provided.
  • the deposition rate of Compound 9, Compound Example (III) -20, and D-10 was energized by energizing the heated boat containing Compound 9 as the host compound and Compound Example (III) -20 and D-10 as the dopant compound.
  • the heating boat containing ET-11 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride was vapor-deposited to form a cathode buffer layer having a thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a thickness of 110 nm.
  • an organic EL element 6-1 was produced.
  • the present invention provides an organic electroluminescence element that exhibits high light emission efficiency, has a long light emission lifetime, and can suppress an increase in voltage during driving, and an illumination device and a display device including the element. Suitable for

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Abstract

La présente invention concerne un élément électroluminescent organique, comportant au moins une couche électroluminescente entre une électrode positive et une électrode négative, et contenant un complexe d'iridium orthométalaté coordonné hexadentate représenté par la formule générale (I). Dans cette formule générale (I), V représente un groupe de liaison bivalente ; L2 et L3 sont liés par covalence l'un à l'autre ; chacun des L1 à L3 représente un groupe représenté par la formule générale (II) ; X5 et Ir sont liés par coordination l'un à l'autre ; et X7 et Ir sont liés par covalence l'un à l'autre. Dans la formule générale (II), X1 à X5 forment une chaîne hétérocyclique contenant de l'azote ; X6 à X11 forment une chaîne aromatique à cinq éléments ou une chaîne aromatique à six éléments ; et chacun des X1 à X11 représente un atome de carbone ou un atome d'azote, X4 et/ou X5 étant un atome d'azote. Dans le cas où X6 à X11 forment une chaîne aromatique à cinq éléments, X11 représente une simple liaison.
PCT/JP2012/080815 2011-12-14 2012-11-29 Élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage WO2013088959A1 (fr)

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US9847496B2 (en) 2013-12-23 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US11744142B2 (en) 2017-08-10 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices

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WO2007018067A1 (fr) * 2005-08-05 2007-02-15 Idemitsu Kosan Co., Ltd. Composé complexe de métaux de transition et dispositif électroluminescent organique l’utilisant
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WO2015008851A1 (fr) * 2013-07-17 2015-01-22 住友化学株式会社 Composition et élément électroluminescent utilisant cette composition
JP5867650B2 (ja) * 2013-07-17 2016-02-24 住友化学株式会社 組成物およびそれを用いた発光素子
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US11744142B2 (en) 2017-08-10 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices

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