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WO2008035595A1 - Dispositifs électroluminescents organiques - Google Patents

Dispositifs électroluminescents organiques Download PDF

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Publication number
WO2008035595A1
WO2008035595A1 PCT/JP2007/067714 JP2007067714W WO2008035595A1 WO 2008035595 A1 WO2008035595 A1 WO 2008035595A1 JP 2007067714 W JP2007067714 W JP 2007067714W WO 2008035595 A1 WO2008035595 A1 WO 2008035595A1
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organic
dopant material
emitting layer
light emitting
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PCT/JP2007/067714
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English (en)
Japanese (ja)
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Mitsuyoshi Naito
Yoshiyuki Suzuri
Aki Nakata
Hiroshi Kita
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Konica Minolta Holdings, Inc.
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Priority to JP2008535328A priority Critical patent/JP5470849B2/ja
Publication of WO2008035595A1 publication Critical patent/WO2008035595A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07F15/0086—Platinum compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
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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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/80—Composition varying spatially, e.g. having a spatial gradient
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • H—ELECTRICITY
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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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
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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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Definitions

  • the present invention relates to an organic electoluminescence element.
  • ELD components include inorganic-electric luminescence elements and organic-electric luminescence elements (hereinafter also referred to as organic EL elements! /).
  • Inorganic electoric luminescence elements require high alternating current voltage to drive the force light-emitting elements that have been used as planar light sources.
  • An organic EL device has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and electrons and holes are injected into the light emitting layer and recombined to generate excitons.
  • a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative is doped with a trace amount of a phosphor to improve emission luminance and extend the lifetime of the element.
  • an element having an organic light emitting layer in which an 8-hydroxyquinoline aluminum complex is used as a host compound and a small amount of phosphor is doped to the host compound for example, JP-A 63-264692
  • an 8-hydroxyquinoline aluminum complex is used as a host.
  • an element having an organic light emitting layer doped with a quinacridone dye for example, Japanese Patent Publication No. 3-255190
  • the upper limit of the internal quantum efficiency is 100%, so that in principle the luminous efficiency is four times that of the excited singlet, and almost the same performance as a cold cathode tube is obtained. It is also attracting attention as a lighting application.
  • Japanese Patent Application Laid-Open No. 2001-247859 and the like also attempt to atomize using various iridium complexes.
  • the light emission brightness and the light emission efficiency in the case of the light emitting element are greatly improved as compared to the conventional element because the emitted light is derived from phosphorescence.
  • the light emission lifetime was lower than that of the conventional device.
  • phosphorescent high-efficiency light-emitting materials can sufficiently achieve performance that can withstand practical use where it is difficult to shorten the emission wavelength and improve the light emission lifetime of the device! Currently.
  • a metal complex in which a partial structure of rubazole is introduced into the mother nucleus of phenylrubiridine is known (see, for example, Patent Documents 1 and 2).
  • a metal complex in which a partial structure of rubazole is introduced into the mother nucleus of vinyl bilazole is known as a ligand (see, for example, Patent Document 3).
  • Patent Document 3 a metal complex in which a partial structure of rubazole is introduced into the mother nucleus of vinyl bilazole.
  • the light emitting region in the light emitting layer that is, the concentration of the content of the metal complex is controlled to control the light emitting position at the light emitting layer interface. Controlling and extending the life is performed (for example, see Patent Documents 6 and 7). [0020]
  • these technologies do not show a significant improvement in the light emission lifetime, and there remains room for improvement.
  • Patent Document 1 Japanese Patent Laid-Open No. 2004-67658
  • Patent Document 2 Japanese Patent Laid-Open No. 2005-23070
  • Patent Document 3 International Publication No. 04/085450 Pamphlet
  • Patent Document 4 Pamphlet of International Publication No. 05/007767
  • Patent Document 5 Japanese Patent Laid-Open No. 2005_68110
  • Patent Document 6 Japanese Unexamined Patent Publication No. 2003-229272
  • Patent Document 7 Japanese Patent Laid-Open No. 2005-108730
  • An object of the present invention is to provide an organic electoluminescence device having an excellent emission lifetime.
  • the dopant material is represented by the following general formula (1):
  • An organic electoluminescence device characterized in that the concentration of the dopant material decreases from the anode side to the cathode side in the thickness direction of the light emitting layer
  • R represents a substituent.
  • Z represents a group of nonmetallic atoms necessary to form a 5- to 7-membered ring.
  • nl represents an integer of 0 to 5.
  • B to B are carbon atom, nitrogen atom, oxygen atom or sulfur
  • M Represents a yellow atom and at least one represents a nitrogen atom.
  • M is 8 to 10 in the periodic table of elements; 10
  • X and X represent a carbon atom, a nitrogen atom or an oxygen atom, and L represents X
  • 1 2 1 1 represents an atomic group that forms a bidentate ligand together with X.
  • ml represents an integer of 1, 2 or 3
  • m2 represents a force S representing an integer of 0, 1 or 2
  • ml + m2 represents 2 or 3.
  • the ionization potential Iph of the host material and the ionization potential Ipd of the dopant material satisfy the following formula (1): Organic electoluminescence element.
  • a / B ⁇ l.5 is satisfied when the concentration of the dopant material contained on the anode side of the light emitting layer is 8% by mass and the concentration of the dopant material contained on the cathode side is 8% by mass.
  • the present invention relates to an organic electoluminescence device (hereinafter also referred to as an organic EL device) having at least a light emitting layer containing a host material and a dopant material between an opposing cathode and anode. It is represented by the general formula (1), and the concentration of the dopant material is reduced from the anode side to the cathode side in the thickness direction of the light emitting layer.
  • the stepwise decrease from the anode side to the cathode side means that the dopant content is constant in the range of 2 nm or more.
  • the deposition rate is controlled by the deposition temperature. To achieve a continuous decrease.
  • the light emitting region in the light emitting layer that is, the concentration of the dopant material content is controlled to control the light emitting position at the light emitting layer interface. Controlling and extending the service life are performed (for example, JP-A Nos. 2003-229272 and 2005-108730).
  • the generation ratio of singlet excitons and triplet excitons is 1: 3 compared to a fluorescent light emitting device using light emission from an excited singlet.
  • the upper limit of the internal quantum efficiency is 100%, and in principle the light emission efficiency is four times that of the excited singlet case, and highly efficient light emission can be obtained.
  • phosphorescent light-emitting elements are known to have a poor lifetime compared to fluorescent light-emitting elements, and in particular, blue phosphorescent light-emitting elements are still insufficient for practical use.
  • the dopant material represented by the general formula (1) As a result of intensive studies, we have found that the dopant material represented by the general formula (1) Thus, it was found that a long-lived phosphorescent light-emitting device can be obtained. As a result of further intensive studies, in the phosphorescent light emitting device using the dopant material represented by the general formula (1), a change in the dopant concentration in the light emitting layer, specifically, a concentration gradient (from the anode side to the cathode side) It has been found that the light emission life is further extended by attaching a high concentration on the anode side and a low concentration on the negative side, and the present invention has been completed.
  • Such a concentration gradient is confirmed by cutting the light emitting layer obliquely and measuring with TOF-SIMS.
  • an oblique cross section is prepared with Cycus NN04 (manufactured by Daipura Wintes).
  • the light emitting layer contains a plurality of dopants, they can be distinguished by the difference in molecular weight.
  • TOF— SIMS measurement can be performed using TRIFT2, a time-of-flight secondary ion mass spectrometer manufactured by Physical Electronics, with primary ions and In ions with an acceleration voltage of 25kV (beam current is 2nA).
  • the ionization potential is defined as the energy required to release an electron at the HOMO (highest occupied molecular orbital) level of a compound to the vacuum level.
  • the ionization potential is a film state (layer state). This is the energy required to extract electrons from the compound, and these are the photoelectron content. It can be measured directly by the optical method. For example, it can be measured with an ESCA 5600 UPS ultraviolet photoemission spectroscopy manufactured by ULVAC-FAI.
  • the concentration of the dopant material contained on the anode side of the light emitting layer is 8% by mass and the concentration of the dopant material contained on the cathode side is 8% by mass
  • the upper limit of satisfying 5 is 20, the upper limit is preferably 10, and the upper limit is more preferably 5.
  • the anode side concentration (8% by mass) refers to the dopant concentration contained within the light emitting layer thickness lnm from the interface between the light emitting layer and the layer adjacent to the anode side of the light emitting layer
  • the cathode side concentration (8% by mass) refers to the dopant concentration contained within the thickness of the light emitting layer within lnm from the interface between the light emitting layer and the layer adjacent to the cathode side of the light emitting layer.
  • an alkyl group for example, a methyl group, an ethyl group, a propyl group, an isopropylene group, a t-butyl group, a pentyl group, a hexyl group, an octyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, etc.
  • a cycloalkyl group for example, cyclopentyl group, cyclohexyl group, etc.
  • an alkenyl group for example, bur group, allyl group, etc.
  • an alkynyl group for example, a methyl group, an ethyl group, a propyl group, an isopropylene group, a t-butyl group, a pentyl group, a hexyl group, an octyl group, a dodecyl group,
  • aromatic hydrocarbon ring group aromatic hydrocarbon ring group
  • aromatic carbocyclic group aromatic carbocyclic group
  • aromatic heterocyclic group e.g., pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, imidazolyl group, benzoimidazolyl group, pyrazolyl group, pyrajuryl group, triazolyl group (for example, 1, 2, 4 ⁇ lyso 'monore 1 inole group, 1, 2, 3 ⁇ lyso' mono o
  • Z represents a group of non-metallic atoms necessary for forming a 5- to 7-membered ring. Formed by Z 5 ⁇
  • Examples of the 7-membered ring include a benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, pyrrole ring, thiophene ring, pyrazole ring, imidazole ring, oxazole ring and thiazole ring. Of these, a benzene ring is preferred.
  • B to B represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and at least one of them
  • the aromatic nitrogen-containing heterocycle formed by these five atoms is preferably a monocycle.
  • Examples thereof include a pyrrole ring, a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazol ring, an oxadiazole ring, and a thiadiazole ring.
  • a pyrazole ring and an imidazole ring are preferable, and an imidazole ring is more preferable.
  • These rings may be further substituted with the above substituents.
  • Preferable examples of the substituent are an alkyl group and an aryl group, and more preferable is an aryl group.
  • L represents an atomic group forming a bidentate ligand together with X and X.
  • X — L — 2 represented by X
  • 1 1 2 1 1 2dentate ligand examples include, for example, substituted or unsubstituted phenylpyrrolidine, phenylpyrazonole, phenylimidazonole, phenyltriazolene, phenyltetrazole, virazol ball, Examples include picolinic acid and acetylacetone.
  • ml represents an integer of 1, 2 or 3
  • m2 represents a force of 0, 1 or 2 ml + m2 is
  • m2 is preferably 0.
  • Examples of the metal represented by M include transition metal elements of groups 8 to 10 of the periodic table (simply transition gold).
  • iridium and platinum are preferable, and iridium is more preferable.
  • the dopant material represented by the general formula (1) of the present invention has a polymerizable group or a reactive group!
  • the nitrogen-containing heterocycle formed from 1 to B is 5
  • a dopant material represented by the following general formula (2) which is a midazole ring is preferred. [0059] [Chemical 2]
  • R, R, and R represent a substituent
  • R in the general formula (1) represents
  • R represents a substituent having a steric parameter value (Es value) of -0.5 or less.
  • the Es value is a steric parameter derived from chemical reactivity. The smaller this value is, the smaller the sterically bulky! /, The more sterically bulky! /, The substituent! it can.
  • the Es value will be described as! /.
  • the Es value is a quantification of the steric hindrance of substituents.
  • Es log (kX / kH)
  • the reaction rate decreases due to the steric hindrance of the substituent X, resulting in kX and kH, so the Es value is usually negative.
  • the above two reaction rate constants kX and kH are obtained and calculated by the above formula.
  • the Es value as defined in the present specification is a value obtained by setting a hydrogen atom to 0 instead of defining it as 0 for a methyl group. Es value from 1
  • the Es value is 1 or less 0.5. Preferably it is 17.0 or more and 10.6 or less. Most preferably, it is 17.0 or more and 11.0 or less.
  • the phosphorescence wavelength of a compound is the 0-0 band of the phosphorescence spectrum.
  • the 0-0 band of the phosphorescence spectrum can be obtained by the following measurement method.
  • the compound to be measured is dissolved in well-deoxygenated methylene chloride, put into a phosphorescence measurement cell, irradiated with excitation light at room temperature (25 ° C), and the emission spectrum is measured.
  • any solvent that cannot dissolve in the above-mentioned solvent system and / or that can dissolve the compound may be used.
  • force S which is a method for obtaining the 0-0 band
  • the emission maximum wavelength that appears on the shortest wavelength side in the phosphor spectrum chart obtained by the above measurement method is 0-0. It is defined as a band. If the phosphorescence spectrum is weak, noise and peaks can be separated and peak wavelengths can be read by smoothing. As smoothing processing, the Savitzky & Glay smoothing method can be applied.
  • the phosphorescence wavelength peak is preferably 480 nm or less.
  • the light emitting layer according to the present invention will be described.
  • the light emitting layer according to the present invention is injected from an electrode, an electron transport layer, a hole transport layer, or the like.
  • the light-emitting portion may be in the light-emitting layer or at the interface between the light-emitting layer and the adjacent layer.
  • the light emitting layer of the organic EL device of the present invention contains a dopant material and a host material.
  • a dopant material it is preferable to use the compound according to the present invention described above as a dopant material.
  • a plurality of known dopant materials may be used in combination.
  • a plurality of dopant materials it is possible to mix different light emission, and thus any light emission color can be obtained.
  • White light emission is possible by adjusting the kind of dopant material and the amount of doping, and it can also be applied to lighting and knock lights.
  • JP 2002-100476 JP 2002-173674, JP 2002-359082, JP 2002-175884, JP 2002-363552, JP 2002-184582 Publication, JP 2003-7469, JP 2002-525 808, JP 2003-7471, JP 2002-525833, JP 2003
  • the light emitting layer As a material used for the light emitting layer, there is a host material in addition to the above dopant material.
  • the host material refers to a room temperature (2
  • At 5 ° C) is defined as a compound having a phosphorescence quantum yield of phosphorescence of less than 0.01.
  • the host material used in the present invention is not particularly limited in terms of structure, but representative examples thereof include force rubazole derivatives and triarylamine derivatives.
  • the host material is preferably a compound that prevents the emission of light from becoming longer in wavelength and has a high Tg (glass transition temperature).
  • high Tg means 100 ° C or more.
  • the hole transport layer includes a 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.
  • a single hole or multiple hole transport layers should be provided.
  • hole transport material there are no particular restrictions on the hole transport material. Conventionally, in photoconductive materials, it is commonly used as a hole charge injection and transport material, and used in the hole injection layer and hole transport layer of EL devices. Any known one can be selected and used.
  • 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 for example, 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, hydrazones Derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N-tetraphenenole 4, A'-diaminophenol, N, N-diphenylenole N, N'-bis (3-methylphenyl) 1 [1, 1'-biphenyl] 1, 4, 4'-diamin (TPD); 2, 2-bis (4-di-triarylaminophenyl) propane; 1, 1 —Bis (4-di-tritriaminophenenyl) cyclohexane; N, N, N ′, N ′ —Tetra-p-trinore 4, A′-diaminobiphenyl; 1, 1-bis (4-di 1 p triarylaminophenyl) 4-phenylsilk Bis (4-dimethylamino-2-methylphenenyl) phenylmethane; bis (4-di-p-tolylaminophenyl)
  • a polymer material in which these materials are introduced into a polymer chain or these materials 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 a hole injection material and a hole transport material.
  • the hole transport material preferably has a high Tg.
  • This hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • An impurity-doped hole transporting layer having a high p property can also be used. Examples thereof include those described in JP-A-4-297076, JP-A-2000-196140, 2001-102175, J. Appl. Phys., 95, 5773 (2004), etc. It is done.
  • 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 has a single layer or multiple layers.
  • an electron transport material also serving as a hole blocking material
  • the electron transport layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer, and any material can be selected from conventionally known compounds. .
  • electron transport materials examples include heterocyclic tetrafluoride derivatives, difluoroquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, and other heterocyclic tetra Examples thereof include carboxylic anhydrides, carpositimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, and oxadiazole derivatives.
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron-withdrawing group can be used as an electron transport material.
  • 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.
  • metal complexes of 8 quinolinol derivatives such as tris (8 quinolinol) aluminum (Alq), tris (5,7-dichloro-1-8-quinolinol) aluminum, tris (5,7-dib mouth mode)
  • the central metal of these metal complexes is 8 quinolinol) anoreminium, tris (2 methinolay 8 -quinolinol) aluminum, tris (5-methyl 8-quinolinol) aluminum, bis (8-quinolinol) zinc (Zn q), etc.
  • Metal complexes replacing Mg, Cu, Ca, Sn, Ga or Pb can also be used as electron transport materials.
  • metal free or metal phthalocyanine, or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material.
  • the distyrylvirazine derivative exemplified as the material for the light-emitting layer can be used as an electron transport material, and, like the hole injection layer and the hole transport layer, such as n-type Si and n-type SiC.
  • Inorganic semiconductors can also be used as electron transport materials.
  • This electron transport layer is formed by using the above electron transport material, for example, a vacuum deposition method, a spin coating method, a key. It is possible to form a thin film by a known method such as a dust method, an ink jet method, or an LB method. Although there is no restriction
  • This electron transport layer may have a single layer structure composed of one or more of the above materials.
  • an impurity-doped electron transport layer having a high n property can be used.
  • impurity-doped electron transport layer having a high n property examples thereof include those described in JP-A-4-297076, JP-A-2000-196140, 2001-102175, J. Appl. Phys., 95, 5773 (2004), etc. It is done.
  • 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.
  • electrode materials include metals such as Au, and conductive transparent materials such as Cul, indium tin oxide (ITO), SnO, and ZnO.
  • conductive transparent materials such as Cul, indium tin oxide (ITO), SnO, and ZnO.
  • ITO indium tin oxide
  • ZnO ZnO
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
  • the anode may be formed by forming a thin film by depositing these electrode materials by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or pattern accuracy is not required so much! / In some cases (about 100 ⁇ m or more), the pattern may be formed through a mask of the desired shape during the deposition or sputtering of the electrode material. In the case where light is extracted from the anode, it is desirable that the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / mouth or less. Furthermore, the film thickness depends on the material, usually 10 to 1000 bells, preferably. It is selected in the range of ⁇ 200.
  • the 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 is used.
  • an electron injecting metal a material having a low work function (4 eV or less) metal
  • an alloy a material having a low work function (4 eV or less) metal
  • an alloy a material having a low work function (4 eV or less) metal
  • an alloy referred to as an electron injecting metal
  • an alloy an electrically conductive compound
  • a mixture thereof a mixture thereof.
  • Specific examples of such electrode materials include sodium, sodium isotropic lithium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al O) 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 value than this, for example, magnesium / Silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3) mixtures, lithium / aluminum mixtures, aluminum and the like are suitable.
  • 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 ⁇ / mouth or less, and the preferred film thickness is usually 10 to 1000 nm, preferably 50 to 200 nm.
  • the light emission luminance is improved, which is convenient.
  • Substrate also referred to as substrate, substrate, support, etc.
  • the substrate of the organic EL device of the present invention is not particularly limited as long as it is transparent or transparent, and there are no particular restrictions on the type of glass, plastic, etc.
  • Examples of substrates that are preferably used include glass, Examples thereof include quartz and a light-transmitting resin film.
  • a particularly preferred substrate is a resin film that can give flexibility to the organic EL element.
  • Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC ), A film made of cellulose triacetate (TAC), cellulose acetate propionate (CAP) or the like.
  • the surface of the resin film is a high barrier film having a water vapor transmission rate of 0.01 g / m 2 'day or less, which may have an inorganic or organic coating or a hybrid coating of both. I prefer to be there.
  • the external extraction efficiency at room temperature of light emission of the organic electoluminescence device of the present invention is preferably 1% or more, more preferably 5% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted outside the organic EL element / the number of electrons flowing through the organic EL element ⁇ 100.
  • a roughened film such as anti-glare phenol may be used in combination in order to reduce unevenness in light emission.
  • the sealing means used for sealing the organic EL element of the present invention includes, for example, a method in which a sealing member, an electrode, and a support base are bonded with an adhesive.
  • the sealing member may have a concave plate shape or a flat plate shape as long as it is arranged so as to cover the display area of the organic EL element. Further, transparency and electrical insulation are not particularly limited.
  • a glass plate, a polymer plate 'film, a metal plate' film and the like can be mentioned.
  • the glass plate include soda lime glass, norlium strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, norium borosilicate glass, and quartz.
  • Examples of the polymer plate include 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.
  • Examples of the adhesive include photocuring and thermosetting adhesives having a reactive bur group of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanacrylic acid esters. it can.
  • hot melt polyamides, polyesters, and polyolefins can be cited.
  • an organic EL element may be deteriorated by heat treatment, an element that can be adhesively cured from room temperature to 80 ° C. is preferable.
  • a desiccant is dispersed in the adhesive. Let's go! / Use a commercially available dispenser to apply the adhesive to the sealing area, or print it like screen printing.
  • the electrode and the organic layer may be coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer may be 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 the intrusion of elements such as moisture and oxygen that cause deterioration of the element, such as silicon oxide, silicon dioxide, silicon nitride, and the like. Can be used.
  • a protective film or a protective plate may be provided on the outer side of the sealing film or the sealing film on the side facing the support substrate with the organic layer interposed therebetween.
  • the sealing is the sealing film
  • the mechanical strength is not necessarily high, so it is preferable to provide such a protective film and protective plate.
  • the material that can be used for this is the same glass plate, polymer plate 'film, metal plate' film, etc. that can be used for the sealing. Therefore, it is preferable to use a polymer film.
  • a method for producing an organic EL device comprising an anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode will be described.
  • a desired electrode material for example, a thin film made of an anode material is formed on a suitable support substrate by a method such as vapor deposition or sputtering so as to have a thickness of 1 ⁇ m or less, preferably 10 to 200 nm.
  • an organic EL thin film of an organic EL element material ie, a hole injection layer, a hole transport layer, an intermediate layer, and a light emitting layer, a hole blocking layer, and an electron transport layer
  • a method for thinning the organic compound thin film there are a vapor deposition method and a wet process (spin coating method, casting method, ink jet method, printing method) as described above. From the point of being difficult to form, a vacuum deposition method, a spin coating method, an ink jet method, and a printing method are particularly preferable. Further, different film forming methods may be applied for each layer.
  • Film in the case of employing an evaporation method different forces generally boat temperature 50 to 450 ° C such as the type of compound the deposition conditions used, the degree of vacuum 10- 6 to 10-2 Pa, the deposition rate 0.01 to 50 belly / second, substrate temperature—50 to 300. C, film thickness 0.1 to 5, preferably 5 to 200 nm.
  • a thin film made of a cathode material is formed thereon by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 50 to 200 nm.
  • a desired organic EL device can be obtained by providing a cathode.
  • the organic EL device may be manufactured from the hole injection layer to the cathode consistently by a single evacuation, or may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere. It is also possible to reverse the order of layers and reverse the layer order.
  • a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the anode as + and the cathode as one polarity.
  • An alternating voltage may be applied.
  • the alternating current waveform to be applied may be arbitrary.
  • the organic electoluminescence element of the present invention can be used as a display device, a display, or various light sources.
  • Illumination devices that use the organic EL elements of the present invention as light-emitting sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources for optical storage media, and electrophotographic copying.
  • the organic EL device of the present invention may be used as one kind of lamp for illumination or exposure light source, a projection device of a type for projecting an image, a still image or a moving image directly. It may be used as a visual display device (display).
  • the driving method for use 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 manufactured by using three or more organic EL elements of the present invention having different emission colors.
  • a single emission color for example, white emission, can be made into a full color by extracting B, G, and R light using a color filter.
  • the emission color of the organic EL element can be converted to another color by using a color conversion filter, so that it can be fully colorized.
  • the max of organic EL emission should be 480 nm or less. Is preferred.
  • This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of CuPc was placed in a resistance heating boat made of molybdenum and 200 mg of a NPD was placed in another resistance heating boat made of molybdenum.
  • the hole-transporting layer was heated at a deposition rate of 0. Inm / second and 0.012 nm / second by energizing and heating the heated boat containing H-1 and the heated boat containing Compound 1 79. Co-deposition was started, and the heating boat containing Compound 1 79 was adjusted so that the concentration of Compound 1-79 contained in the light-emitting layer on the cathode side was 3% by mass. A light emitting layer was provided. At this time, the concentration of compound 1-79 in the light emitting layer is negative from the anode side. It changes continuously to the extreme side.
  • the heating boat containing BAlq was energized, and was 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 during vapor deposition was room temperature.
  • a cathode was formed by vapor deposition of 110 nm to prepare an organic EL device 1-1.
  • the light emission lifetime of each element shown in Table 3 is the driving voltage (V) at which the front luminance of each organic EL element is 1000 cd / m 2
  • the time until the brightness was reduced to half was expressed as a relative directivity with the organic EL element 1-4 as 100.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of CuPc is put into a resistance heating boat made of molybdenum and 200 mg of a NPD is put into another resistance heating boat made of molybdenum.
  • the heating boat containing H 1 and the heating boat containing Compound 199 were energized and heated, and deposited on the hole transport layer at a deposition rate of 0. Inm / second and 0.012 nm / second. Co-evaporation was started, and the heating boat containing Compound 1 99 was adjusted to emit light with a thickness of 40 nm so that the concentration of Compound 1-99 contained in the light emitting layer on the cathode side was 3% by mass. A layer was provided. At this time, the concentration of compound 119 in the light emitting layer continuously changes from the anode side to the negative side.
  • An electron transport layer having a thickness of 30 nm was provided by vapor deposition on the light emitting layer.
  • the substrate temperature during vapor deposition was room temperature.
  • each organic EL element is driven with a driving voltage (V) at which the front luminance is lOOOcdZm 2 and the time until the luminance is halved is measured. It is expressed as a relative straightness where 100 is 100.
  • V driving voltage
  • This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of CuPc was placed in a resistance heating boat made of molybdenum, and 200 mg of a NPD was placed in another resistance heating boat made of molybdenum.
  • the hole-transporting layer was heated at a deposition rate of 0. Inm / second and 0.009 nm / second by energizing and heating the heated boat containing H-1 and the heated boat containing Compound 199.
  • Co-deposition was started on top, 5 nm thick film was deposited, and the heating boat containing H-1 and the heating boat containing compound 1-9 were energized and heated, and the deposition rate was 0. Inm / sec.
  • Co-evaporation was started on the hole transport layer at 0.006 nm / second, and a 35 nm-thick film was deposited to provide a 40 nm thick light-emitting layer.
  • the concentration of Compound 199 in the light emitting layer changes stepwise from the anode side to the cathode side.
  • the heating boat containing BAlq was energized and deposited on the light emitting layer at a deposition rate of 0. Inm / sec to provide an electron transport layer having a thickness of 30 nm.
  • the substrate temperature during vapor deposition was room temperature.
  • organic EL element 2-1 In the production of organic EL element 2-1, except that the concentration of compound 1-99 on the anode side and the concentration of compound 1-99 on the cathode side are as shown in Table 6, organic EL element 3— Organic EL elements 3-2 to 3-4 were fabricated in the same manner as in 1.
  • the light emission lifetime was evaluated in the same manner as in Example 1. Relative values when the organic EL elements 3-4 are set to 100 are shown.
  • this ITO transparent electrode was provided.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • dilute poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate PEDOT / PSS: Bayer, Baytron P Al 4083
  • PEDOT / PSS Bayer, Baytron P Al 4083
  • This substrate was transferred to a nitrogen atmosphere, and a solution of 50 mg ⁇ NPD dissolved in 10 ml of toluene was formed on the first hole transport layer by spin coating at 1000 rpm for 30 seconds. A two-hole transport layer was formed.
  • the compound 1-99 is dissolved from the first light-emitting layer by the toluene solvent and diffuses to the second light-emitting layer, so that the content of the compound 199 continuously changes, and in the anode-side light-emitting layer A light emitting layer was produced in which the content of compound 1-99 was greater than the content of compound 1-99 on the cathode side.
  • the total thickness of the light emitting layer including the first light emitting layer and the second light emitting layer was about 50 nm.
  • the content of compound 1-99 contained in the toluene solution at the time of forming the first light emitting layer was Omg
  • the toluene solution at the time of forming the second light emitting layer was Organic EL device 4-2 was produced in the same manner except that the content of compound 1-99 contained was 10 mg.
  • the concentration of the compound 199 on the anode side of the light emitting layer is smaller than the concentration of the compound 199 on the cathode side.
  • the content of compound 1-99 contained in the toluene solution at the time of forming the first light emitting layer was 5 mg, and the second light emitting layer was not formed.
  • an organic EL element 43 was produced.
  • the light emitting layer is uniform with the concentration of Compound 199 not changing from the anode side to the cathode side.
  • the light emission lifetime was evaluated in the same manner as in Example 1. The values are shown as relative values when the organic EL element 43 is 100.
  • the organic EL device of the present invention has a long lifetime even in the coating type organic EL device.

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  • Crystallography & Structural Chemistry (AREA)
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Abstract

L'invention concerne un dispositif électroluminescent organique présentant une durée de vie de luminescence excellente, qui comporte comme éléments essentiels une cathode et une anode qui se font face l'une à l'autre et une couche émettant de la lumière entre la cathode et l'anode qui contient à la fois un matériau hôte et un matériau dopant, caractérisé par le fait que le matériau dopant est représenté par la formule générale (1) et la concentration du matériau dopant diminue dans la direction de l'épaisseur de la couche émettant de la lumière du côté anode au côté cathode: dans laquelle R1 est un substituant; Z est un groupe atomique non métallique nécessaire pour la formation d'un cycle à 5 à 7 chaînons; n1 est un entier de 0 à 5; B1 à B5 sont chacun le carbone, l'azote, l'oxygène ou le soufre, au moins l'un d'entre eux étant l'azote; M1 est un élément choisi parmi les métaux du groupe 8 à 10 du tableau périodique; X1 et X2 sont chacun le carbone, l'azote ou l'oxygène; et L1 est un groupe atomique capable de former conjointement avec X1 et X2 un ligand bidentate.
PCT/JP2007/067714 2006-09-19 2007-09-12 Dispositifs électroluminescents organiques WO2008035595A1 (fr)

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