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WO2010004877A1 - 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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WO2010004877A1
WO2010004877A1 PCT/JP2009/061592 JP2009061592W WO2010004877A1 WO 2010004877 A1 WO2010004877 A1 WO 2010004877A1 JP 2009061592 W JP2009061592 W JP 2009061592W WO 2010004877 A1 WO2010004877 A1 WO 2010004877A1
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group
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organic
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順子 田丸
秀雄 ▲高▼
利恵 片倉
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コニカミノルタホールディングス株式会社
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • 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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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Definitions

  • the present invention relates to an organic electroluminescence element, a display device, and a lighting device. More specifically, the present invention relates to an organic electroluminescence element that suppresses unevenness in light emission and achieves a long life and high efficiency, and a display device and a lighting device including the element.
  • ELD electroluminescence display
  • inorganic electroluminescent elements and organic electroluminescent elements (hereinafter also referred to as organic EL elements).
  • organic electroluminescent elements have been used as planar light sources, but an alternating high voltage is required to drive the light emitting elements.
  • an organic EL element has a configuration in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and injects electrons and holes into the light emitting layer to recombine excitons. It is an element that emits light by utilizing light emission (fluorescence / phosphorescence) when the exciton is deactivated.
  • the thickness between the electrodes is only about 0.1 ⁇ m, and the light can be emitted at a relatively low voltage of several volts to several tens of volts. Since it is rich in corners, has high visibility, and is a thin-film type completely solid element, it has attracted attention as a next-generation flat display and illumination from the viewpoint of space saving and portability.
  • an organic EL element is composed of a plurality of organic layers having functions other than light emission, in addition to a light emitting layer, in order to realize low voltage, high luminous efficiency, and high luminance. Yes.
  • an organic EL element can emit light more efficiently by adding a small amount of a dopant compound to the host compound in the light emitting layer.
  • dopant molecules fluorescent dopants represented by quinacridone derivatives (for example, JP-A-3-255190) and phosphorescent dopants represented by iridium (III) tris (2-phenylpyridine) are known, Research has been actively conducted on phosphorescent dopants having higher luminous efficiency and host molecules for efficiently emitting phosphorescent dopants (see, for example, Patent Documents 1 to 3).
  • vapor deposition and coating methods are known as methods for producing organic EL elements, which can be easily applied to increase the area of organic EL elements and will be manufactured at low cost in the future. Since it is estimated that it can be done, research on organic EL device fabrication by a coating method has been extensively conducted in recent years. (For example, JP 2008-13700 A) However, when organic EL elements are applied to lighting applications or large-area electronic displays, especially when large-area elements are created using a coating method, leakage current and dark spots are more prominent than small-area elements. There is a problem of becoming.
  • Organic EL elements are known to have a significant decrease in light emitting lifetime due to very few dark spots, and this is a major obstacle to increasing the area of organic EL elements. Further, as a problem specific to the increase in area of the light emitting element, there is light emission unevenness in the light emitting element.
  • the light emission unevenness in the element is difficult to solve by controlling the current and voltage, and this also becomes a factor that hinders the increase in area of the organic EL element.
  • Patent Document 4 As a means for solving the light emission unevenness, a method using a metal mesh plate subjected to etching (for example, see Patent Document 4) is known.
  • Patent Document 1 is for suppressing uneven light emission between a plurality of light emitting elements, and does not suppress uneven light emission within a single element, which is a problem in the present invention.
  • the method for example, refer patent document 5
  • the present invention has been made in view of the above problems, and an object of the present invention is to provide an organic EL element, a lighting device, and a display device with little dark spot, leakage current, and light emission unevenness in the light emitting element.
  • each of the organic electroluminescence devices having a plurality of organic layers including a light emitting layer sandwiched between an anode and a cathode,
  • each of the organic layers contains a compound represented by the following general formula (1) and a compound represented by the following general formula (2) independently of each other .
  • the compound represented by the general formula (1) and the compound represented by the general formula (2) may be contained in the same layer or in different layers).
  • R 11 to R 18 and R 21 to R 28 each represent a hydrogen atom or a substituent. However, at least one of R 11 to R 18 and at least one of R 21 to R 28 are used for connection with X.
  • X represents an arylene group or a heteroarylene group.
  • n represents an integer of 0 or more, and when n is 2 or more, Xs may be the same or different.
  • R 1 to R 5 each represents a substituent.
  • B 1 ⁇ B 3 represents a carbon atom or a nitrogen atom
  • L A is to form a bidentate ligand with B 2 and B 3.
  • Z A , Z B and Z C each independently represents an atomic group necessary for forming a hydrocarbon ring group or a heterocyclic group.
  • n 1 represents an integer of 0 to 5
  • n 2 represents an integer of 0 to 3
  • n 3 represents an integer of 0 to 4.
  • M represents a transition metal element of Group 8 to Group 10 of the periodic table.
  • m 1 represents an integer of 1 to 3
  • m 2 represents an integer of 0 to 2
  • m 1 + m 2 is 2 or 3.
  • 2. The organic electroluminescence device according to 1 above, wherein in the general formula (1), X is bonded to R 16 and R 23 .
  • n is 1 or more, and at least one kind of X is represented by the following general formula (3).
  • R 30 to R 38 are each connected to a hydrogen atom, a substituent, or at least one of R 11 to R 18 and at least one of R 21 to R 28 . ] 4).
  • R 33 and R 36 are each connected to at least one of R 11 to R 18 and at least one of R 21 to R 28. Electroluminescence element.
  • Y represents —N (R 30 ) — (wherein R 30 represents a hydrogen atom or a substituent, provided that R 11 to R 18 and R 21 to R 28 are connected to each other).
  • R 30 represents a hydrogen atom or a substituent, provided that R 11 to R 18 and R 21 to R 28 are connected to each other).
  • R 11 ⁇ R 18 and R 21 ⁇ R 28 are each the formula in (1) have the same meanings as R 11 ⁇ R 18 and R 21 ⁇ R 28. ]
  • R 11 ⁇ R 18 and R 21 ⁇ R 28 are each the formula in (1) have the same meanings as R 11 ⁇ R 18 and R 21 ⁇ R 28. ] 7). 7.
  • n 6 represents an integer of 0 to 4
  • n 7 represents an integer of 0 to 2
  • n 8 represents an integer of 0 to 3.
  • M represents a transition metal element of Group 8 to Group 10 of the periodic table.
  • the organic layer containing the compound represented by the general formula (1) and the compound represented by the general formula (2) and any one layer adjacent to the organic layer are formed by a coating method. 12.
  • An organic layer containing the compound represented by the general formula (1) and the compound represented by the general formula (2) and two layers adjacent to the organic layer are formed by a coating method. 13.
  • a display device comprising the organic electroluminescence element as described in any one of 1 to 14 above.
  • An illumination device comprising the organic electroluminescence element according to any one of 1 to 14.
  • the organic EL element of the present invention can provide a highly durable organic EL element, and a lighting device and a display device using the element.
  • organic EL device of the present invention a highly durable (long-life) organic EL device could be obtained by having the structure according to any one of claims 1 to 14.
  • the present inventors have clarified that the cause of light emission unevenness is closely related to the likelihood of aggregation of the compounds constituting the organic layer.
  • the compound to be applied is easy to agglomerate, the compound in the organic thin film that constitutes the organic layer becomes partially dense and the organic thin film becomes uniform. It could not be formed, causing not only unevenness of light emission but also a leakage current, and it was found that it caused a decrease in durability of the element.
  • the above problem can be solved by incorporating the compound represented by the general formula (1) and the compound represented by the general formula (2) into at least one layer constituting the organic EL.
  • the route was found and the present invention was reached.
  • the organic EL element produced using the compound represented by the general formula (1) and the compound represented by the general formula (2) was able to obtain a highly durable element.
  • the compounds represented by the general formula (1) and the general formula (2) are considered to be able to form a film having a uniform and smooth density in the organic layer when mixed with other compounds.
  • an organic EL device is manufactured using the compound represented by the general formula (1) as a host compound (also simply referred to as a host) and the compound represented by the general formula (2) as a light-emitting dopant (also simply referred to as a dopant).
  • a host compound also simply referred to as a host
  • the compound represented by the general formula (2) as a light-emitting dopant
  • a highly durable (long life) organic EL element could be produced.
  • the host compound, the light-emitting dopant, etc. will be described later in detail at the constituent layers of the organic EL element.
  • examples of the substituent represented by R 11 to R 18 , R 21 to R 28 and R 30 to R 38 include an alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group).
  • cycloalkyl group eg cyclopentyl group, cyclohexyl group etc.
  • alkenyl group eg vinyl Group, allyl group, etc.
  • alkynyl group for example, ethynyl group, propargyl group, etc.
  • aromatic hydrocarbon ring group aromatic carbocyclic group, aryl group, etc.
  • phenyl group, p-chlorophenyl group mesityl Group, tolyl group, xylyl group, naphthyl group, anthryl group, azulenyl group, acenaphthenyl group, fluorenyl Group, phenanthryl group, indenyl
  • Acyl groups for example, acetyl group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group, cyclohexylcarbonyl group, octylcarbonyl group, 2-ethylhexylcarbonyl group, dodecylcarbonyl group, phenylcarbonyl group, naphthylcarbonyl group, pyridylcarbonyl) Group), acyloxy group (for example, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.), amide group (for example, methylcarbonylamino group, Ethylcarbonylamino group, dimethylcarbonylamino group, propylcarbonylamino group, pentylcarbonylamino group, cyclo
  • substituents may be further substituted with the above substituents.
  • a plurality of these substituents may be bonded to each other to form a ring.
  • a hydrogen atom, an aromatic hydrocarbon ring group or an aromatic heterocyclic group is preferable.
  • examples of the arylene group represented by X include an o-phenylene group, m-phenylene group, p-phenylene group, naphthalenediyl group, anthracenediyl group, naphthacenediyl group, pyrenediyl group, and naphthylnaphthalene.
  • Diyl group Diyl group, biphenyldiyl group (eg, [1,1′-biphenyl] -4,4′-diyl group, 3,3′-biphenyldiyl group, 3,6-biphenyldiyl group, etc.), terphenyldiyl group, Quaterphenyldiyl group, kinkphenyldiyl group, sexiphenyldiyl group, septiphenyldiyl group, octiphenyldiyl group, nobiphenyldiyl group, deciphenyldiyl group, etc.).
  • biphenyldiyl group eg, [1,1′-biphenyl] -4,4′-diyl group, 3,3′-biphenyldiyl group, 3,6-biphenyldiyl group, etc.
  • examples of the heteroarylene group represented by X include a carbazole ring, a carboline ring, a diazacarbazole ring (also referred to as a monoazacarboline ring, and one of carbon atoms constituting the carboline ring).
  • a carbazole ring also referred to as a monoazacarboline ring, and one of carbon atoms constituting the carboline ring.
  • n is preferably 1 or more, more preferably at least one is a heteroarylene group, and more preferably a carbazole ring, a carboline ring, or a diazacarbazole ring.
  • Also referred to as a monoazacarboline ring, which is a divalent group derived from a ring structure in which one of the carbon atoms constituting the carboline ring is replaced with a nitrogen atom is particularly preferred is the general formula (3 ).
  • X when n is 2 or more, X may be different, but at least one X is preferably the above heteroarylene group, more preferably Is a group represented by the general formula (3).
  • R 30 to R 38 are each represented by R 11 to R 18 , R 21 to R 28 and R 30 to R 38 in the general formula (1). It is synonymous with a substituent.
  • Y is preferably a —N (R 30 ) — group.
  • R 30 is preferably a substituent.
  • substituents are the same as those of R 11 to R 18 and R 21 to R 28, and among them, an aromatic hydrocarbon ring group or an aromatic heterocyclic group is preferable, and among them, a phenyl group is preferable.
  • substituent of R 30 may be used for linking with any of R 11 to R 18 or 21 to R 28 in the general formula (1).
  • the compound represented by the general formula (1) the compound represented by the general formula (4) or the compound represented by the general formula (5) is preferable.
  • R 11 to R 18 and R 21 to R 28 are respectively R 11 to R 18 in the general formula (1). And R 21 to R 28 .
  • the molecular weight is not specified, but the molecular weight is preferably in the range of 700 to 5,000, Furthermore, it is in the range of 800 to 3000.
  • n is not particularly limited, but is preferably 50 or less, more preferably 20 or less, and particularly preferably 10 or less.
  • the structure of the obtained intermediate 2 was confirmed by a nuclear magnetic resonance spectrum and a mass spectrum.
  • the structure of the obtained intermediate 4 was confirmed by a nuclear magnetic resonance spectrum and a mass spectrum.
  • At least one of the organic layers constituting the device contains a compound represented by the general formula (2) (also referred to as a metal complex), preferably the general formula (6) The compound represented by these is used.
  • the compound represented by General formula (2) or General formula (6) which concerns on this invention is used as a light emission dopant in the light emitting layer of the organic EL element of this invention.
  • the constituent layers and constituent materials of the elements such as the light emitting layer and the light emitting dopant will be described in detail in the constituent layers of the organic EL element described later.
  • the substituents represented by R 1 to R 10 are R 11 to R 18 , R 21 to R 28 and R 30 to R 38 in the general formula (1). It is synonymous with the kind of substituent in.
  • the substituent represented by R 1 to R 10 is preferably a hydrogen atom, an aromatic hydrocarbon ring group or an aromatic heterocyclic group.
  • Z A , Z B , and Z C each independently represent a hydrocarbon ring group or a heterocyclic group, for example, an aromatic hydrocarbon ring group (both aromatic carbocyclic group and aryl group)
  • an aromatic hydrocarbon ring group (both aromatic carbocyclic group and aryl group)
  • An aromatic heterocyclic group for example, pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, imidazolyl group, benzoimidazolyl group, pyrazolyl group, pyrazinyl group, triazolyl
  • the Z A for example, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrrolyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, preferably a oxazolyl group and thiazolyl group, more preferably, They are a phenyl group, a naphthyl group, and a pyridyl group, and most preferably a phenyl group.
  • the Z B a pyridyl group, a pyrimidyl group, a pyrrolyl group, an imidazolyl group, a benzimidazolyl group, a pyrazolyl group, pyrazinyl group, triazolyl group, oxazolyl group and thiazolyl group, more preferably a pyridyl group , A pyrimidyl group, an imidazolyl group, a benzimidazolyl group and a triazolyl group, and most preferably a pyridyl group and an imidazolyl group.
  • the Z C a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrrolyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a carbazolyl group and a diaza-carbazolyl Group is preferred, more preferably a phenyl group, a naphthyl group, a pyridyl group and a carbazolyl group, and most preferably a phenyl group and a carbazolyl group.
  • L A represents an atomic group that forms a bidentate ligand together with B 2 and B 3 .
  • Specific examples of the bidentate ligand represented by B 2 -L A -B 3 include, for example, substituted or unsubstituted phenylpyridine, phenylpyrazole, phenylimidazole, phenyltriazole, phenyltetrazole, pyrazabol and the like. It is done.
  • These groups may be further substituted with the same substituents as R 11 to R 18 , R 21 to R 28 and R 30 to R 38 .
  • m 1 represents an integer of 1 to 3
  • m 2 represents an integer of 0 to 2
  • m 1 + m 2 is 2 or 3. Above all, when m 2 is 0 are preferred.
  • a transition metal element of Group 8 to Group 10 of the periodic table of elements (also simply referred to as transition metal) is used, among which iridium and platinum are preferable, Iridium is preferred.
  • the compound represented by the general formula (2) may or may not have a polymerizable group or a reactive group.
  • Step 1 Synthesis of Complex A
  • iridium chloride trihydrate 8. 1 g (0.02297 mol) and 100 ml of water were added and refluxed for 5 hours under a nitrogen atmosphere.
  • the reaction solution was cooled, 500 ml of methanol was added, and the precipitated crystals were collected by filtration. The obtained crystals were further washed with methanol and dried to obtain 15.2 g (yield: 88.4%) of Complex A.
  • Step 2 Synthesis of Exemplified Compound D-21
  • 6.0 g (0.003998 mol) of complex A and 1.85 g (0.008396 mol) of silver trifluoroacetate obtained in step 1 were refluxed in 500 ml of methylene chloride for 1 hour while carrying out nitrogen bubbling.
  • the above synthesis method is an example, and the present invention is not limited thereto.
  • various compounds can be synthesized by changing the solvent to be used to a polar solvent having a high boiling point such as phenyl acetate, changing the amount of the reaction substrate, or changing the reaction temperature.
  • the dopant used in the present invention is not limited to the one according to the present invention, and by combining with other dopants, the emission intensity can be increased and the emission peak can be shifted.
  • an organic EL element that emits white light can be achieved by mixing a plurality of dopants.
  • dopants that may be used in the present invention are shown below, but usable dopants are not limited to these.
  • the organic EL device of the present invention preferably has a plurality of organic compound layers as a constituent layer.
  • the organic compound layer include a hole transport layer, a light emitting layer, and a hole blocking layer in the above layer constitution.
  • an organic compound layer according to the present invention is defined as long as it contains an organic compound contained in a constituent layer of an organic EL element, such as a hole injection layer or an electron injection layer. Is done.
  • an organic compound is used for the anode buffer layer, the cathode buffer layer, etc.
  • the anode buffer layer, the cathode buffer layer, etc. each form an organic compound layer.
  • the organic compound layer includes a layer containing “organic EL element material that can be used for a constituent layer of an organic EL element” or the like.
  • the blue light emitting layer preferably has an emission maximum wavelength of 430 nm to 480 nm
  • the green light emitting layer has an emission maximum wavelength of 510 nm to 550 nm
  • the red light emitting layer has an emission maximum wavelength of 600 nm to 640 nm.
  • a monochromatic light emitting layer in the range is preferable, and a display device using these is preferable.
  • a white light emitting layer may be formed by laminating at least three of these light emitting layers. Further, a non-light emitting intermediate layer may be provided between the light emitting layers.
  • the organic EL element of the present invention is preferably a white light emitting layer, and is preferably a lighting device using these.
  • 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 thickness of the light emitting layer is not particularly limited, but from the viewpoint of preventing the application of a high voltage unnecessary for the film uniformity and light emission, and improving the stability of the emitted color with respect to the driving current.
  • the thickness is preferably adjusted to 5 ⁇ m, more preferably 2 nm to 200 nm, and particularly preferably 10 nm to 20 nm.
  • a light-emitting dopant or a host compound is formed by a known thinning method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or an ink-jet method. I can do it.
  • the light emitting layer of the organic EL device of the present invention preferably contains a host compound and at least one kind of light emitting dopant (phosphorescent dopant, fluorescent dopant, etc.).
  • the host compound in the present invention is a phosphorescent quantum yield of phosphorescence emission at a room temperature (25 ° C.) having a mass ratio of 20% or more in the compound contained in the light emitting layer. Is defined as a compound of less than 0.1.
  • 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.
  • a compound having a structure represented by general formula (1), general formula (4), or general formula (5) is particularly preferably used as the host compound.
  • a well-known host compound may be used together, and may be used in combination of multiple types.
  • a host compound By using a plurality of types of host compounds, it is possible to adjust the movement of charges, and the organic EL element can be made highly efficient. Moreover, it becomes possible to mix different light emission by using multiple types of light emission dopants mentioned later, and, thereby, arbitrary light emission colors can be obtained.
  • a conventionally known host compound that may be used in combination is preferably a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of light from becoming longer, and has a high Tg (glass transition temperature).
  • the light emitting dopant according to the present invention a fluorescent dopant or a phosphorescent light emitting dopant can be used. From the viewpoint of obtaining an organic EL element with higher luminous efficiency, the light emitting layer or light emitting unit of the organic EL element of the present invention.
  • the luminescent dopant used in the above it is preferable to contain the above-mentioned host compound and at the same time a phosphorescent dopant.
  • a compound (metal complex) having a structure represented by the general formula (2) is preferred as a phosphorescent dopant, and particularly preferably a compound (metal complex) represented by the general formula (6). Is mentioned.
  • the phosphorescent dopant is a compound in which light emission from an excited triplet is observed.
  • the phosphorescent dopant is a compound that emits phosphorescence at room temperature (25 ° C.), and the phosphorescence quantum yield is 25 ° C.
  • the preferred phosphorescence quantum yield is 0.1 or more.
  • the above phosphorescence quantum yield can be measured by the method described in Spectra 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 emitting dopant according to the present invention achieves the above phosphorescence quantum yield (0.01 or more) in any solvent. It only has to be done.
  • the energy transfer type is to obtain light emission from the phosphorescent dopant by transferring to the phosphorescent dopant, and the other is that the phosphorescent dopant becomes a carrier trap, and carrier recombination occurs on the phosphorescent dopant to cause phosphorescence.
  • the phosphorescent dopant is appropriately selected from known compounds used for the light emitting layer of the organic EL device and the compound represented by the general formula (2) or the general formula (6) of the present invention. It is possible to use a compound represented by general formula (2) or general formula (6).
  • the phosphorescent dopant is preferably a complex compound containing a group 8-10 metal in the periodic table, more preferably an iridium compound (Ir complex), an osmium compound, or a platinum compound (platinum complex compound). ), Rare earth complexes, and most preferred among these are iridium compounds (Ir complexes).
  • Fluorescent dopants include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes, stilbene dyes , Polythiophene dyes, or rare earth complex phosphors.
  • Injection layer electron injection 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.
  • examples thereof include a phthalocyanine buffer layer represented by an oxide, an oxide buffer layer represented by vanadium oxide, an amorphous carbon buffer layer, and a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.
  • 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 lithium, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer layer typified by aluminum oxide, etc.
  • 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. By blocking this, the recombination probability of electrons and holes can be improved.
  • the structure of the electron transport layer described later 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 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 molecular orbital) level of the compound to the vacuum level, and can be obtained by the following method, for example.
  • Gaussian 98 Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.
  • the ionization potential can be obtained as a value obtained by rounding off the second decimal place of a value (eV unit converted value) calculated by performing structural optimization using B3LYP / 6-31G *.
  • eV unit converted value a value obtained by performing structural optimization using B3LYP / 6-31G *.
  • the ionization potential can also be obtained by a method of direct measurement by photoelectron spectroscopy.
  • 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 probability of recombination 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 in the range of 3 nm to 100 nm, more preferably in the range of 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 either hole injection or transport or 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.
  • the compounds represented by the general formula (1), general formula (4) and general formula (5) of the present invention can also be used as the hole transport material.
  • 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
  • polymer materials in which these materials are introduced into polymer chains or these materials are used as polymer main chains 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. I can do it.
  • 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 examples thereof include JP-A-4-297076, JP-A-2000-196140, and JP-A-2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
  • a hole transport layer having such a high p property because a device with lower power consumption can be produced.
  • 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 as a single layer or a plurality of layers.
  • an electron transport material also serving as a hole blocking material used for an electron transport layer adjacent to the light emitting layer on the cathode side is injected from the cathode.
  • Any material may be used as long as it has a function of transferring electrons to the light-emitting layer, and any of known materials can be selected for use.
  • Examples include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like.
  • 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 also 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-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, A metal complex replaced with Cu, Ca, Sn, Ga, or Pb can also be used as an electron transport material.
  • 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 distyrylpyrazine derivative exemplified as the material of the light emitting layer can also be used as an electron transport material, and similarly to the hole injection layer and the hole transport layer, an inorganic semiconductor such as n-type-Si or n-type-SiC. Can also be used as an electron transporting material.
  • the electron transport layer can be formed by thinning the above electron 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.
  • the film thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • the electron transport layer may have a single layer structure composed of one or more of the above materials.
  • an electron transport layer having a high n property doped with impurities examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J.A. 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.
  • Electrode materials 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 required (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 coating film forming method such as a printing method or a coating method can also be used.
  • the transmittance is 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.
  • 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 a 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.
  • the light emission luminance is improved, which is convenient.
  • a transparent or semi-transparent cathode can be produced by producing a conductive transparent material mentioned in the description of the anode on the cathode after producing the metal with a film thickness of 1 nm to 20 nm. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
  • 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.
  • the transparent support substrate that can be 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 , Polyether imide, polyether ketone imide, polyamide, fluororesin, nylon, polymethyl methacrylate, acrylic or polyarylates, cycloolefin resin such as Arton (manufactured by JSR)
  • JSR
  • 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 ⁇ MPa) 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.
  • vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam, ion plating, plasma polymerization, atmospheric pressure plasma polymerization A plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or 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 quantum efficiency at room temperature of light emission of the organic EL 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 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.
  • sealing means used in the present invention include a method of bonding a sealing member, an electrode, and a support substrate with an adhesive.
  • 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 polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
  • 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 ⁇ MPa) or less, and a method according to JIS K 7129-1992.
  • the water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH) measured in (1) is preferably 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. I can do it.
  • heat- and chemical-curing type such as epoxy type can be mentioned.
  • 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 degrees 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.
  • an inorganic or organic layer as a sealing film by covering the electrode and the organic layer on the outer side of the electrode facing the support substrate with the organic layer interposed therebetween, and in contact with the support substrate.
  • 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. I can do it.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil in the gas phase and the liquid phase.
  • a vacuum can also be used.
  • a hygroscopic compound can also be enclosed inside.
  • Examples of the hygroscopic compound 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.
  • Etc. 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, etc.), and anhydrous salts are preferably used in sulfates, metal halides and perch
  • 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 sealing is performed by the sealing film, the mechanical strength is not necessarily high. Therefore, it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, etc. as used for the sealing can be used. It is preferable to use a film.
  • the organic EL element emits light inside a layer having a higher refractive index than air (refractive index is about 1.7 to 2.1), and only about 15% to 20% of the light generated in the light emitting layer can be extracted. It is generally said that there is no.
  • 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), and light emission from the 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.
  • Bragg diffraction such as first-order diffraction and second-order diffraction.
  • light that cannot be emitted due to total reflection between layers, etc. is diffracted by introducing a diffraction grating into any layer or medium (inside 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 to 100 ⁇ m. If it becomes smaller than this, the effect of diffraction will generate
  • the condensing sheet it is possible to use, for example, a sheet that has been put to practical use in an LED backlight of a liquid crystal display device.
  • 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 by forming a ⁇ -shaped 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.
  • a desired electrode material for example, a thin film made of an anode material is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably 10 nm to 200 nm.
  • an organic compound thin film of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer is formed thereon.
  • a method for forming each of these layers there are a vapor deposition method and a coating method (spin coating method, casting method, ink jet method, printing method) as described above, but it is easy to obtain a homogeneous film and it is difficult to generate pinholes.
  • film formation by a coating method such as a spin coating method, an ink jet method, or a printing method is preferable in the present invention.
  • the layer containing the compound having the structure represented by the general formula (1) is preferably formed by the above coating method, and the layer is preferably a light emitting layer.
  • the total number of layers (the constituent layers of the organic EL element) existing between the anode and the cathode 50% or more of the total number of layers is preferably formed by a coating method.
  • the hole injection layer In the case where the total number of layers / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer is 6, it is preferable that at least three layers are formed by a coating method.
  • examples of the liquid medium for dissolving or dispersing various organic EL materials used for coating include ketones such as methyl ethyl ketone and cyclohexanone, and fatty acid esters such as ethyl acetate.
  • ketones such as methyl ethyl ketone and cyclohexanone
  • fatty acid esters such as ethyl acetate.
  • Halogenated hydrocarbons such as dichlorobenzene, aromatic hydrocarbons such as toluene, xylene, mesitylene and cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin and dodecane, and organic solvents such as DMF and DMSO I can do it.
  • a dispersion method it can be dispersed by a dispersion method such as ultrasonic wave, high shear force dispersion or media dispersion.
  • 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 nm to 200 nm, and a cathode is provided.
  • a desired organic EL element can be obtained.
  • the cathode, electron injection layer, electron transport layer, hole blocking layer, light emitting layer, hole transport layer, hole injection layer, anode, and the like can be manufactured in the reverse order.
  • 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.
  • An alternating voltage may be applied.
  • the alternating current waveform to be applied may be arbitrary.
  • the organic EL element of the present invention can be used as a display device, a display, and various light 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 Examples include, but are not limited to, a light source of a sensor.
  • the light source can be effectively used as a backlight of a liquid crystal display device or a light source for illumination.
  • 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. I can do it.
  • 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 CS-1000 (manufactured by Konica Minolta Sensing) is applied to the CIE chromaticity coordinates.
  • the organic EL element of the present invention is a white element
  • Example 1 Preparation of model thin film 1 of light emitting layer of organic EL element >> A quartz substrate of 30 mm ⁇ 30 mm ⁇ 1.1 mm was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, subjected to UV ozone cleaning for 5 minutes, then attached to a commercially available spin coater, and H-1 (50 mg) and Ir -3 (5 mg) dissolved in 10 ml of toluene was formed by spin coating at 1500 rpm for 30 seconds, and further vacuum dried at 25 ° C. for 1 hour to obtain a model thin film 1 having a thickness of 25 nm. Produced.
  • model thin films 2 to 9 for light emitting layer of organic EL element were prepared in the same manner except that the host compound H-1 and the phosphorescent dopant (also referred to as phosphorescent compound) were changed as shown in Table 1. Each was produced.
  • Ra measurement, P-to-V measurement >> With respect to the obtained model thin films 1 to 9, the surface roughness was measured at a measurement area of 50 ⁇ m ⁇ 50 ⁇ m, 10 ⁇ m ⁇ 10 ⁇ m using an apparatus name: SPI3800N DFM manufactured by SII and a cantilever: SI-DF20. Thereby, Ra measurement values and P-to-V measurement values were obtained.
  • Ra is a kind of JIS roughness shape parameter (JIS B0601-1994) and represents the centerline average roughness.
  • the roughness curve is folded from the center line, and the value obtained by dividing the area obtained by the roughness curve and the center line by the length L is expressed in micrometers ( ⁇ m).
  • P-to-V is the same as Ry, which is a kind of JIS roughness shape parameter (JIS B0601-1994), and represents the height from the lowest valley bottom to the highest mountain peak for each reference length.
  • the maximum height of the section from which the reference length L is extracted from the cross-sectional curve is obtained and expressed in micrometers ( ⁇ m), which is defined as a P-to-V value or Ry value.
  • the cross-sectional curve represents a contour that appears at the cut end when the surface to be measured is cut along a plane perpendicular to the surface to be measured.
  • Ra and P-to-V were obtained based on the obtained surface roughness data.
  • a thin film containing a compound represented by the general formula (1) and a compound represented by the general formula (2) can be formed into a thin film having a low P-to-V value and high smoothness. I understood.
  • Example 2 Production of Organic EL Element 1-1 >> Patterning was performed on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) on which a 100 nm ⁇ 100 mm ⁇ 1.1 mm glass substrate as a positive electrode on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate was formed, and then 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.
  • the substrate was transferred to a nitrogen atmosphere, and a solution of 50 mg of the hole transport material 1 dissolved in 10 ml of toluene was formed on the hole transport layer by spin coating at 1500 rpm for 30 seconds.
  • ultraviolet light was irradiated for 180 seconds to carry out photopolymerization and crosslinking to form a second hole transport layer having a thickness of about 20 nm.
  • a solution prepared by dissolving 100 mg of Comparative Compound 1 and 10 mg of Compound Ir-3 in 10 ml of toluene was formed into a film by spin coating under conditions of 1000 rpm and 30 seconds. It vacuum-dried at 120 degreeC for 1 hour, and was set as the light emitting layer with a film thickness of about 50 nm.
  • this substrate is fixed to a substrate holder of a vacuum deposition apparatus, the vacuum chamber is decompressed to 4 ⁇ 10 ⁇ 4 Pa, lithium fluoride 1.0 nm is deposited as a cathode buffer layer, and aluminum 110 nm is deposited as a cathode to form a cathode.
  • an organic EL element 1-1 was produced.
  • FIG. 2 is a schematic diagram of the lighting device, and the organic EL element 201 is covered with a glass cover 202. Note that the sealing operation with the glass cover was performed in a glove box in a nitrogen atmosphere without bringing the organic EL element 201 into contact with the atmosphere (in a high purity nitrogen gas atmosphere with a purity of 99.999% or more).
  • FIG. 3 is a cross-sectional view showing one embodiment of the lighting device of the present invention.
  • 205 denotes a cathode
  • 206 denotes an organic EL layer
  • 207 denotes a glass substrate with a transparent electrode.
  • the glass cover 202 is filled with nitrogen gas 208 and a water catching agent 209 is provided.
  • a spectral radiance meter CS-1000 manufactured by Konica Minolta was used.
  • the measurement results of the lifetime in Table 1 are expressed as relative values when the organic EL element 1-1 is 100.
  • FIG. 4 shows a schematic configuration diagram of an organic EL full-color display device. After patterning at a pitch of 100 ⁇ m on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) having a 100 nm thick ITO transparent electrode (102) formed on a glass substrate 101 as an anode, non-between the ITO transparent electrodes on this glass substrate. A photosensitive polyimide partition 103 (width 20 ⁇ m, thickness 2.0 ⁇ m) was formed by photolithography.
  • a hole injection layer composition having the following composition is ejected and injected between polyimide partition walls on the ITO electrode using an inkjet head (manufactured by Epson; MJ800C), irradiated with ultraviolet light for 2 minutes, and dried at 60 ° C. for 10 minutes.
  • a hole injection layer 104 having a thickness of 40 nm was produced by the treatment.
  • the following blue light-emitting layer composition, green light-emitting layer composition, and red light-emitting layer composition were similarly discharged and injected using an inkjet head, and dried at 60 ° C. for 10 minutes.
  • Each light emitting layer (105B, 105G, 105R) was formed.
  • Al (106) was vacuum-deposited as a cathode so as to cover the light emitting layer 105, and an organic EL element was produced.
  • the produced organic EL element showed blue, green and red light emission by applying voltage to each electrode, and could be used as a full color display device.
  • Example 4 Preparation of white organic EL element 3-1 >> A hole transport layer / second hole transport layer was formed by spin coating on the transparent electrode substrate of Example 2 in the same manner as in Example 2, and 100 mg of Compound Example H-3, 10 mg was further formed as a light emitting layer. A solution of D-3 and 0.1 mg of D-38 dissolved in 10 ml of toluene was formed into a film by spin coating at 1000 rpm for 30 seconds. It vacuum-dried at 120 degreeC for 1 hour, and was set as the light emitting layer with a film thickness of about 50 nm.
  • Example 2 Next, in the same manner as in Example 2, an electron transport layer, a lithium fluoride layer, and an aluminum cathode were formed to produce a white light-emitting organic EL element 3-1.
  • the obtained organic EL element 3-1 was sealed in the same manner as in Example 2.

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Abstract

L'invention porte sur un élément électroluminescent organique comprenant une pluralité de couches organiques agencées entre une anode et une cathode et comprenant une couche électroluminescente. L'élément électroluminescent organique est caractérisé par le fait qu'un composé représenté par une formule générale (1) et un composé représenté par une formule générale (2) sont indépendamment contenus dans au moins l'une des couches organiques. (A cet égard, le composé représenté par la formule générale (1) et le composé représenté par la formule générale (2) peuvent être contenus dans une même couche ou dans des couches différentes). (Dans la formule générale (1), R11-R18 et R21-R28 représentent chacun un atome d'hydrogène ou un substituant, à condition qu'au moins un de R11-R18 et au moins un de R21-R28 soit utilisé pour la liaison à X ; et X représente un groupe arylène ou un groupe hétéroarylène ; et n représente un entier non inférieur à 0. Lorsque n n'est pas inférieur à 2, les X peuvent être les mêmes ou peuvent être différents l'un de l'autre). (Dans la formule générale (2), R1-R5 représente chacun un substituant ; B1-B3 représente chacun un atome de carbone ou un atome d'azote ; LA forme un ligand bidentate conjointement avec B2 et B3 ; ZA, ZB et ZC représentent indépendamment un groupe atomique nécessaire pour former un groupe cyclique hydrocarbure ou un groupe hétérocyclique ; n1 représente un entier de 0-5 ; n2 représente un entier de 0-3 ; n3 représente un entier de 0-4 ; M représente un élément métal de transition du groupe 8-10 du tableau périodique des éléments ; et m1 représente un entier de 1-3 et m2 représente un entier de 0-2, m1 + m2 valant 2 ou 3.)
PCT/JP2009/061592 2008-07-10 2009-06-25 Élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage WO2010004877A1 (fr)

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