WO2019088262A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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Publication number
WO2019088262A1
WO2019088262A1 PCT/JP2018/040884 JP2018040884W WO2019088262A1 WO 2019088262 A1 WO2019088262 A1 WO 2019088262A1 JP 2018040884 W JP2018040884 W JP 2018040884W WO 2019088262 A1 WO2019088262 A1 WO 2019088262A1
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layer
organic
cathode
light emitting
derivatives
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PCT/JP2018/040884
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English (en)
Japanese (ja)
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千博 源
隆章 岡本
正剛 岩▲崎▼
関口　泰広
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住友化学株式会社
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Priority to CN201880070505.1A priority Critical patent/CN111279507A/zh
Priority to KR1020207015142A priority patent/KR20200083516A/ko
Publication of WO2019088262A1 publication Critical patent/WO2019088262A1/fr

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    • 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
    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/166—Electron transporting layers comprising a multilayered structure
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an organic electroluminescent device.
  • the organic electroluminescent element (hereinafter sometimes referred to as "organic EL element") is configured to include an anode, a cathode, and a light emitting layer disposed between the anode and the cathode.
  • the organic EL element emits light by recombination of holes and electrons respectively injected from the anode and the cathode in the light emitting layer.
  • a layer of an organic metal complex compound may be provided between the cathode and the light emitting layer in order to lower the electron injection barrier from the cathode to the light emitting layer and realize low voltage driving (Patent Document 1) ).
  • This invention is made in view of such a situation, and it aims at providing the organic EL element which can be driven by lower voltage.
  • the organic EL device of the present invention is an organic electroluminescent device comprising an anode and a cathode, and a light emitting layer provided between the anode and the cathode, and a first layer provided between the cathode and the light emitting layer And a second layer provided between the first layer and the cathode, wherein the first layer is at least one selected from the group consisting of alkali metal elements, alkaline earth metal elements and rare earth metal elements.
  • the second layer contains an electron-transporting organic compound and at least one of an alkali metal and an alkaline earth metal. According to such an organic EL element, it is possible to drive at a lower voltage.
  • the first layer may be in contact with the light emitting layer.
  • the second layer may be in contact with the first layer.
  • the cathode may be in contact with the second layer.
  • the above organometallic complex compounds are sodium 8-quinolinolate, lithium 8-quinolinolate, lithium 2- (2 ′, 2 ′ ′-bipyridin-6′-yl) phenolate, and sodium 2- (2 ′, 2 ′ ′ It is preferable to include at least one selected from -bipyridin-6'-yl) phenolate.
  • the first layer preferably contains the organic metal complex compound in a proportion of 50 to 100% by volume.
  • the electron transporting organic compound preferably includes a compound having a fluorene skeleton.
  • the second layer preferably contains at least one of Ca and Ba.
  • FIG. 1 is drawing which shows typically the structure of the organic EL element which concerns on one Embodiment.
  • the organic electroluminescent device (organic EL device) 1 As schematically shown in FIG. 1, in the organic electroluminescent device (organic EL device) 1 according to this embodiment, the anode E1, the hole injection layer 11, the hole transport layer 12, and the light emitting layer 13 are formed on the substrate P. , The second layer 14a and the cathode E2 are provided in order.
  • the first layer 14 b and the second layer 14 a may be collectively referred to as a multilayer electron transport layer 14.
  • the organic EL element 1 can be suitably used for a curved or flat illumination device, for example, a planar light source used as a light source of a scanner, and a display device.
  • the organic EL element 1 may be a bottom emission type in which light emitted from the light emitting layer 13 is emitted through the substrate P, and the light emitted from the light emitting layer 13 is on the opposite side to the substrate P (ie, the cathode E2 It may be a top emission type emitted from the side).
  • a substrate which does not change chemically in the manufacturing process of the organic EL element 1 is suitably used.
  • a substrate which does not change chemically in the manufacturing process of the organic EL element 1 is suitably used.
  • the organic EL element can be flexible as a whole.
  • an electrode for driving the organic EL element 1 or a drive circuit may be formed in advance.
  • the substrate P may be made of a plastic material that substantially transmits visible light (for example, light with a wavelength of 360 nm to 830 nm) emitted from the light emitting layer 13 .
  • At least one of the anode E1 and the cathode E2 is transparent.
  • the anode E1 a thin film with low electric resistance is preferably used.
  • the organic EL element 1 is a bottom emission type
  • the anode E1 disposed on the substrate P side is preferably transparent and has high transmittance to light in the visible light range.
  • a material of the anode E1 a conductive metal oxide film, a metal thin film or the like is used.
  • the anode E1 a thin film made of ITO, IZO and tin oxide is preferably used in view of high transmittance and ease of patterning.
  • the anode E1 is preferably formed of a material that reflects the light from the light emitting layer 13 to the side of the cathode E2.
  • metals, metal oxides or metal sulfides having a work function of 3.0 eV or more are preferable.
  • a metal thin film having a film thickness sufficient to reflect light is used.
  • the organic EL element 1 When the organic EL element 1 is a top emission type, the light from the light emitting layer 13 is reflected by the anode E1 and the light is extracted from the cathode E2 side. Therefore, a material having high visible light reflectance is preferable as the material of the anode E1. Specific materials of such an anode E1 include, for example, aluminum and silver.
  • the organic EL element 1 When the organic EL element 1 is a bottom emission type, the light from the light emitting layer 13 is reflected by the cathode E2 and the light is extracted from the anode E1 side. Therefore, a material having a high visible light transmittance is preferable as the material of the anode E1.
  • Specific materials of such an anode E1 include, for example, indium oxide, zinc oxide, tin oxide, indium tin oxide (abbreviated as ITO), indium zinc oxide (indium zinc oxide: abbreviated IZO), etc. Or gold, platinum, silver, copper, aluminum or an alloy containing at least one of these metals.
  • Examples of the method of forming the anode E1 include a vacuum evaporation method, a sputtering method, an ion plating method, a plating method and the like.
  • a transparent conductive film of an organic substance such as polyaniline or a derivative thereof or polythiophene or a derivative thereof may be used.
  • the thickness of the anode E1 can be appropriately determined in consideration of light transmittance, electric conductivity, and the like.
  • the thickness of the anode E1 is, for example, 10 nm to 10 ⁇ m, preferably 20 nm to 1 ⁇ m, and more preferably 50 nm to 500 nm.
  • the hole injection layer 11 is a functional layer having a function of improving the hole injection efficiency from the anode E1.
  • the hole injection material constituting the hole injection layer 11 include oxides such as vanadium oxide, molybdenum oxide, ruthenium oxide and aluminum oxide, phenylamine compounds, star burst type amine compounds, phthalocyanine compounds, amorphous carbon , Polyaniline, and polythiophene derivatives such as polyethylenedioxythiophene (PEDOT).
  • the hole injection layer 11 may be formed, for example, by a coating method using a coating solution containing the above-described hole injection material.
  • the solvent for the coating solution may be any solvent that dissolves the hole injection material, and for example, chloroform, water, chlorinated solvents such as methylene chloride and dichloroethane, ether solvents such as tetrahydrofuran, aromatic carbons such as toluene and xylene Examples thereof include hydrogen solvents, ketone solvents such as acetone and methyl ethyl ketone, and ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate.
  • Coating methods include spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing,
  • the offset printing method, the inkjet printing method, etc. can be mentioned.
  • the hole injection layer 11 can be formed by applying the coating solution described above on the substrate P on which the anode E1 is formed, using one of these coating methods.
  • hole injection layer 11 it is also possible to form the hole injection layer 11 by vacuum evaporation or the like. Furthermore, when the hole injection layer 11 is made of a metal oxide, it is also possible to form the hole injection layer 11 using a sputtering method, an ion plating method, or the like.
  • the optimum value of the thickness of the hole injection layer 11 varies depending on the material used.
  • the thickness of the hole injection layer 11 is appropriately determined in consideration of the required characteristics, the ease of film formation, and the like.
  • the thickness of the hole injection layer 11 is, for example, 1 nm to 1 ⁇ m, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.
  • the hole transport layer 12 is a layer in contact with the interface on the anode E1 side of the hole transport layer 12 (the hole injection layer 11 in FIG. 1) or from the hole transport layer 12 closer to the anode E1 to the light emitting layer 13 It is a functional layer having a function of improving hole injection.
  • the hole transport material constituting the hole transport layer 12 includes polyvinyl carbazole or a derivative thereof, polysilane or a derivative thereof, a polysiloxane derivative having an aromatic amine in the side chain or main chain, a pyrazoline derivative, an arylamine derivative, a stilbene derivative , Triphenyldiamine derivatives, polyaniline or derivatives thereof, polythiophene or derivatives thereof, polyarylamine or derivatives thereof, polypyrrole or derivatives thereof, poly (p-phenylenevinylene) or derivatives thereof, or poly (2,5-thienylenevinylene) Or derivatives thereof.
  • hole transporting layer materials disclosed in JP 2012-144722 A can also be mentioned.
  • the hole transport layer 12 may be formed, for example, by a coating method using a coating solution containing the above-mentioned hole transport material.
  • the solvent used when forming a film from a solution may be any solvent that dissolves a hole transport material, and is a chlorinated solvent such as chloroform, methylene chloride or dichloroethane, an ether solvent such as tetrahydrofuran, an aroma such as toluene or xylene Group hydrocarbon solvents, ketone solvents such as acetone and methyl ethyl ketone, and ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate.
  • chlorinated solvent such as chloroform, methylene chloride or dichloroethane
  • an ether solvent such as tetrahydrofuran
  • an aroma such as toluene or xylene Group hydrocarbon solvents
  • ketone solvents such as
  • the optimum value of the film thickness of the hole transport layer 12 varies depending on the material used.
  • the film thickness of the hole transport layer 12 is appropriately set so that the drive voltage and the light emission efficiency become appropriate values.
  • the hole transport layer 12 needs to have a thickness such that at least no pinholes occur. If the hole transport layer 12 is too thick, the drive voltage of the device is undesirably increased. Accordingly, the film thickness of the hole transport layer 12 is, for example, 1 nm to 1 ⁇ m, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.
  • the light emitting layer 13 usually contains an organic substance that mainly emits fluorescence and / or phosphorescence, or the organic substance and a dopant material that assists the organic substance.
  • the dopant material is added to the light emitting layer 13 to, for example, improve the light emission efficiency or change the light emission wavelength.
  • the organic substance is preferably a polymer compound from the viewpoint of solubility.
  • the light emitting layer 13 preferably contains a polymer compound having a polystyrene-equivalent number average molecular weight of 1.0 ⁇ 10 3 to 10 8 .
  • Examples of organic substances mainly emitting fluorescence and / or phosphorescence include, for example, the following dye-based materials, metal complex-based materials, and polymer-based materials.
  • dye-based materials include cyclopentamine derivatives, tetraphenylbutadiene derivatives, triphenylamine derivatives, oxadiazole derivatives, pyrazoloquinoline derivatives, distyrylbenzene derivatives, distyrylarylene derivatives, pyrrole derivatives, thiophene ring compounds, Pyridine ring compounds, perinone derivatives, perylene derivatives, oligothiophene derivatives, oxadiazole dimers, pyrazoline dimers, quinacridone derivatives, coumarin derivatives and the like can be mentioned.
  • metal complex materials include rare earth metals such as Tb, Eu and Dy, or Al, Zn, Be, Pt and Ir as central metals, and oxadiazole, thiadiazole, phenylpyridine, phenylbenzimidazole, and the like. Mention may be made of metal complexes having a quinoline structure or the like as a ligand.
  • metal complexes exhibiting luminescence from a triplet excited state such as iridium complex and platinum complex, aluminum quinolinol complex, benzoquinolinol beryllium complex, benzoxazolyl zinc complex, benzothiazole zinc complex, azomethyl zinc complex, A porphyrin zinc complex, a phenanthroline europium complex, etc. can be mentioned.
  • polystyrene resin for example, polyparaphenylene vinylene derivative, polythiophene derivative, polyparaphenylene derivative, polysilane derivative, polyacetylene derivative, polyfluorene derivative, polyvinylcarbazole derivative, the material of the above dye system or the metal complex material is polymerized Materials can be mentioned.
  • materials emitting blue light as materials emitting blue light, distyrylarylene derivatives, oxadiazole derivatives, polymers thereof, polyvinylcarbazole derivatives, polyparaphenylene derivatives, polyfluorene derivatives and the like can be mentioned. Among them, polyvinylcarbazole derivatives, polyparaphenylene derivatives and polyfluorene derivatives of polymer materials are preferable.
  • Materials emitting blue light also include materials disclosed in JP-A-2012-144722.
  • quinacridone derivatives, coumarin derivatives, polymers thereof, polyparaphenylene vinylene derivatives, polyfluorene derivatives and the like can be mentioned.
  • polyparaphenylene vinylene derivatives of polymer materials, polyfluorene derivatives and the like are preferable.
  • Examples of the material that emits green light also include the materials disclosed in JP-A-2012-036388.
  • Examples of materials that emit red light include coumarin derivatives, thiophene ring compounds, polymers thereof, polyparaphenylene vinylene derivatives, polythiophene derivatives, polyfluorene derivatives and the like. Among these, polyparaphenylene vinylene derivatives, polythiophene derivatives, polyfluorene derivatives and the like of polymer materials are preferable. Examples of the material that emits red light also include materials disclosed in JP-A-2011-105701.
  • Examples of the dopant material include perylene derivatives, coumarin derivatives, rubrene derivatives, quinacridone derivatives, squalium derivatives, porphyrin derivatives, styryl dyes, tetracene derivatives, pyrazolone derivatives, decacyclene, phenoxazone and the like.
  • the light emitting layer 13 may be formed by spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, slit coating, capillary coating, Coating methods such as a spray coating method, a nozzle coating method, a gravure printing method, a screen printing method, a flexographic printing method, an offset printing method, a reverse printing method, and an inkjet printing method can be used.
  • the gravure printing method, the screen printing method, the flexographic printing method, the offset printing method, the reverse printing method, and the inkjet printing method are preferable in that pattern formation and multicolor separation are easy.
  • a vacuum evaporation method can be used.
  • the light emitting layer 13 can be formed only at a desired place by a method such as laser transfer or friction transfer, thermal transfer, or the like. Among them, it is preferable to form the light emitting layer 13 by a coating method using a solution containing a light emitting material because of the easiness of the manufacturing process.
  • a solvent of the solution containing the light emitting material for example, the solvents mentioned as the solvent of the coating liquid for forming the hole injection layer 11 described above can be used.
  • the thickness of the light emitting layer 13 is preferably about 2 nm to 200 nm.
  • a first layer 14 b is provided between the light emitting layer 13 and a cathode E 2 described later.
  • the first layer 14 b may be in direct contact with the light emitting layer 13.
  • the first layer 14 b contains an organometallic complex compound.
  • the organometallic complex compound contains at least one selected from the group consisting of an alkali metal element, an alkaline earth metal element and a rare earth metal element.
  • the organometallic complex compound may contain an alkali metal element or an alkaline earth metal element in the form of ions.
  • the alkali metal ion include Li + , Na + , K + , Rb + , and Cs +. Among these, Li + , Na + or Cs + is preferable, and Li + or Na + is more preferable.
  • alkaline earth metal ions include Be 2+ , Mg 2+ , Ca 2+ , Sr 2+ and Ba 2+. Among these, Mg 2+ , Ca 2+ or Ba 2+ are preferable, and Ca 2+ or Ba 2+ is more preferable.
  • the organometallic complex compound may contain a rare earth metal element in the form of ions.
  • rare earth metal ions include Y 3+ , La 3+ , Ce 4+ , Eu 3+ , Gd 3+ , Tb 3+ , and Yb 3+ .
  • Eu 3+ or Yb 3+ is preferable, and Yb 3+ is more preferable.
  • the ligand contained in the organometallic complex compound includes quinolinolate, benzoquinolinolate, acridinolate, phenanthridinolate, hydroxyphenyl oxazole, hydroxyphenyl thial, hydroxy diaryl oxadiazole, hydroxy diaryl thiadiazole, hydroxy phenyl Benzoimidazole, hydroxybenzotriazole, hydroxyfluborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ligands having a 2- (2-pyridyl) phenolate skeleton, ⁇ -diketones, azomethines, and derivatives thereof are listed.
  • Be Specific examples of the ligand contained in the organometallic complex compound include ligands represented by the following formulas (1) to (18).
  • At least one hydrogen atom bonded to a carbon atom contained in a five-membered ring or a six-membered ring is an alkyl group having 1 to 12 carbon atoms It may be substituted.
  • the alkyl group having 1 to 12 carbon atoms is preferably a methyl group, an ethyl group, a propyl group or a tert-butyl group.
  • the organometallic complex compound is represented by the formula (1) (8-quinolinolato), the formula (2) (5-quinoxalinolate), the formula (4) (8-quinazolinolate), Formula (6) (benzo-8-quinolinolato), formula (7) (benzo-5-quinoxalinolate), formula (9) (benzo-8-quinazolinolate), and formula (18) (2- (2'2 ') , 2 ′ ′-bipyridine-6′-yl) phenolate) is preferred, and it is preferred to include a ligand represented by formula (1), formula (2) or formula (4) Is more preferred.
  • organometallic complex compounds include lithium 8-quinolinolato (Liq), sodium 8-quinolinolato (Naq), potassium 8-quinolinolato, 8-quinolinolato rubidium, cesium 8-quinolinolato , Benzo-8-quinolinolate lithium, benzo-8-quinolinolate sodium, benzo-8-quinolinolate potassium, benzo-8-quinolinolate rubidium, benzo-8-quinolinolate cesium, 2-methyl-8 -Quinolinolate lithium, 2-methyl-8-quinolinolate sodium, 2-methyl-8-quinolinolate potassium, 2-methyl-8-quinolinolate rubidium, 2-methyl-8-quinolinolate cesium, lithium 2- ( 2 ′, 2 ′ ′-bipyridin-6′-yl) phenolate (LiBPP) And sodium 2 (2 ', 2 "- bipyridine-6'-yl), and phenolate (NaBPP) is.
  • lithium 8-quinolinolate sodium 8-quinolinolate, lithium 2- (2 ′, 2 ′ ′-bipyridin-6′-yl) phenolate (LiBPP), and sodium 2-2- It is preferred to include at least one selected from the group consisting of (2 ′, 2 ′ ′-bipyridin-6′-yl) phenolate (NaBPP), and more preferred is sodium 8-quinolinolato.
  • the first layer 14 b may contain an electron transporting organic compound.
  • the electron transporting organic compound known organic compounds generally used in the electron transporting layer having a function of transporting electrons can be used.
  • a compound having a fused aryl ring such as naphthalene or anthracene or a derivative thereof, a compound having a fluorene skeleton, a styryl aromatic ring derivative typified by 4,4-bis (diphenylethenyl) biphenyl, a perylene derivative, a perinone derivative, Coumarin derivatives, naphthalimide derivatives, anthraquinones, naphthoquinones, diphenoquinones, quinone derivatives such as anthraquinodimethanes, tetracyanoanthraquinodimethanes, phosphor oxides derivatives, carbazole derivatives, and indole derivatives, tris (8-quinolinolato) aluminum (III) And hydroxyazole
  • PPT 2,8-bis (diphenylphosphoryl) benzo [b, d] thiophene
  • formula (I) a table by the formula (II) TPBi (1,3,5-tris (1-phenyl-1H-benzoimidazol-2-yl) benzene), TmPyPB (1,3,5-tris (3-pyridyl-3) represented by the formula (III)
  • B3PyPB (1,3-bis (3,5-dipyrid-3-ylphenyl) benzene) represented by formula (IV).
  • the electron accepting nitrogen represents a nitrogen atom which forms a multiple bond with the adjacent atom. Because of the high electronegativity of the nitrogen atom, multiple bonds also have electron accepting properties. Thus, heteroaryl rings having an electron accepting nitrogen have high electron affinity. Examples of compounds having a heteroaryl ring structure having an electron accepting nitrogen include benzimidazole derivatives, benzthiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyridine derivatives, pyrazine derivatives, phenanthroline derivatives, quinoxaline derivatives And quinoline derivatives, benzoquinoline derivatives, oligopyridine derivatives such as bipyridine and terpyridine, quinoxaline derivatives, naphthyridine derivatives, phenanthroline derivatives and the like are mentioned as preferable compounds.
  • a compound having a fluorene skeleton is preferable.
  • the compound having a fluorene skeleton include 1- to 8-mers of 9,9-spirobifluorene.
  • a compound having a fluorene skeleton at least one of hydrogens directly bonded to a fluorene ring is substituted by a carbazole group, phosphine oxide group, trimethylsilyl group, triphenylsilyl group, thiophene group, triazine group, bipyridine group, pyridine group or the like It may be one. More specifically, 2,2 ': 7 ", 2'"-ter-9,9'-spirobi [9H-fluorene] (TSBF) is preferred.
  • the first layer 14b has a ratio of 50 to 100% by volume of the organic metal complex compound to 100% by volume of the total amount of materials contained in the first layer 14b. It is preferable to include in the range of 80 to 100% by volume.
  • the first layer 14b As a method of forming the first layer 14b, for example, a method of vacuum depositing an organometallic complex compound may be mentioned.
  • the electron transporting organic compound and the organic metal complex compound may be co-evaporated by a vacuum evaporation method.
  • the ratio of the organic metal complex compound contained in the first layer 14b is the deposition rate of the electron transporting organic compound and the organic metal The adjustment can be made by changing the deposition rate of the complex compound.
  • the thickness of the first layer is not particularly limited, and may be, for example, 0.1 to 10 nm.
  • the second layer 14a is a layer provided between the first layer 14b and the cathode E2, and is an electron-transporting organic compound (hereinafter also referred to as a first material), an alkali metal and an alkaline earth metal. And at least one of the metals (hereinafter also referred to as a second material). That is, the second layer 14a is a layer made of a mixture of the first material and the second material. The second layer 14a may be in direct contact with the first layer 14b.
  • a known organic compound generally used in the electron transport layer can be used. More specifically, those listed as the electron-transporting organic compounds contained in the above-mentioned first layer 14b can be mentioned. Among these, compounds having a fluorene skeleton are preferable.
  • Examples of the alkali metal in the second material contained in the second layer 14a include Li, Na, K, Rb and Cs, and Li, Na, K and Cs are preferable.
  • examples of the alkaline earth metal contained in the second layer 14a include Be, Mg, Ca, Sr, and Ba. Among these, Ca and Ba are preferable.
  • the second material contained in the second layer 14a is preferably an alkaline earth metal.
  • the second layer 14a is a first material with respect to a total of 100% by volume of the materials contained in the second layer 14a from the viewpoint of being able to further reduce the drive voltage of the organic EL element or from the viewpoint of visible light transmittance. 70 to 99% by volume, the second material 1 to 30% by volume, the first material 90 to 99% by volume, the second material 1 to 10% by volume It is more preferable that
  • the driving voltage can be reduced.
  • the second layer does not exist, that is, when the first layer is in direct contact with the cathode such as Al or a reducing metal layer such as Ba, it is included in the organometallic complex compound of the first layer.
  • An alkali metal element or the like can receive an electron from the cathode or the metal layer depending on its oxidation state, and can transfer the electron to the light emitting layer. Thereby, holes and electrons are combined in the light emitting layer, and the light emitting layer emits light.
  • the arrangement of the organometallic complex compound as a by-product is formed at the interface between the first layer and the cathode or metal layer or inside the cathode or metal layer.
  • a complex of the ligand and the metal contained in the cathode or the metal layer is formed. It is considered that such a by-product acts as a resistance component and thus tends to increase the drive voltage of the organic EL element.
  • the organic EL element of the present embodiment since the second layer includes the first material having the electron transporting property together with the second material, the reduction of the organometallic complex compound by the second material is the first Done through the material. Therefore, it is considered that the generation of the by-product is suppressed, and the driving voltage of the organic EL element can be reduced.
  • the first material is also considered to have the function of reducing the electron injection barrier from the cathode to the first layer.
  • the method of co-depositing a 1st material and a 2nd material by a vacuum evaporation method is mentioned, for example.
  • the deposition rate of the first material and the second material is not particularly limited, but the deposition rate of the first material is 0.1 to 1.0 ⁇ / s, and the deposition rate of the second material is 0. .01 to 0.3 ⁇ / s is preferable.
  • the ratio of the first material and the second material contained in the second layer 14a may be the deposition rate of the first material and the second material. It can be adjusted by changing the deposition rate of the material.
  • the second layer preferably has a thickness of 0.1 nm to 200 nm.
  • ⁇ Cathode> As a material of the cathode E2, a material having a small work function, easy electron injection to the second layer 14a, and high electrical conductivity is preferable.
  • the cathode E2 may be in contact with the second layer 14a.
  • the thickness of the cathode E2 is appropriately set in consideration of the electrical conductivity and the durability.
  • the thickness of the cathode E2 is, for example, 10 nm to 10 ⁇ m, preferably 20 nm to 1 ⁇ m, and more preferably 50 nm to 500 nm.
  • the organic EL element 1 When the organic EL element 1 is a top emission type, light from the light emitting layer 13 is extracted from the side of the cathode E2, and therefore, a material having high visible light transmittance is preferable as the material of the cathode E2.
  • a material of such a cathode E2 for example, a thin film made of indium oxide, zinc oxide, tin oxide, indium tin oxide (abbreviated as ITO), indium zinc oxide (indium zinc oxide: abbreviated IZO), etc.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • gold, platinum, silver, copper, aluminum, an alkali metal, an alkaline earth metal, an alloy containing at least one of these metals, or the like is used.
  • the organic EL element 1 When the organic EL element 1 is a bottom emission type, the light from the light emitting layer 13 is reflected by the cathode E2 and the light is extracted from the anode E1 side. Therefore, a material having a high visible light reflectance is preferable as the material of the cathode E2.
  • Specific materials of such a cathode E2 include, for example, indium oxide, zinc oxide, tin oxide, indium tin oxide (abbreviated as ITO), indium zinc oxide (indium zinc oxide: abbreviated IZO), etc. Or thin films of gold, platinum, silver, copper, aluminum, alkali metals, alkaline earth metals, alloys containing at least one of these metals, and the like.
  • Examples of a method of forming the cathode E2 include a vacuum evaporation method, a sputtering method, and a lamination method of thermocompression bonding of a metal thin film.
  • the configuration of the organic EL element is not limited to the configuration illustrated in FIG.
  • the organic EL element should just have the 1st layer 14b and the 2nd layer 14a between the light emitting layer 13 and the cathode E2.
  • the example of the possible layer configuration of an organic EL element is shown.
  • a layer including the first layer and the second layer is also referred to as a multilayer electron transport layer.
  • the “multilayer type electron transport layer” specifically means any of the laminated structures shown in the following (i) to (vi).
  • First laminated structure first layer / second layer
  • second laminated structure first layer / second layer / electron injection layer
  • third laminated structure first layer / Second layer / electron transport layer / electron injection layer
  • fourth laminated structure first layer / second layer / electron transport layer
  • fifth laminated structure first layer / electron injection layer / Second layer / electron transport layer
  • sixth laminated structure first layer / electron transport layer / second layer / electron transport layer
  • the electron injection layer improves the electron injection efficiency from the cathode E2 to the second layer 14a or from the second layer 14a to the first layer 14b. It is a functional layer having a function.
  • the optimum value of the thickness of the electron injection layer varies depending on the material used, but the thickness of the electron injection layer is appropriately set in consideration of electrical characteristics, easiness of film formation, and the like.
  • the thickness of the electron injection layer is, for example, 0.1 nm to 1 ⁇ m.
  • a well-known electron injection material can be used for the material of an electron injection layer.
  • a material of the electron injection layer for example, an alloy containing one or more of alkali metals, alkaline earth metals, alkali metals and alkaline earth metals, oxides of alkali metals or alkaline earth metals, halides, carbonates , Fluoride, or a mixture of these substances.
  • a layer obtained by mixing a conventionally known electron-transporting organic material and an organic metal complex of an alkali metal can be used as electron injection.
  • the electron transport layer transports electrons from the cathode E2 to the second layer 14a or the electron injection layer, or from the second layer 14a to the first layer 14b. It is a layer having a function.
  • the electron transporting material constituting the electron transporting layer is not particularly limited as long as it is generally used as an electron transporting material, but, for example, the first layer 14 b and the second layer 14 a described above And electron transporting organic compounds contained in the above.
  • the film thickness of the electron transport layer may be, for example, 0.1 nm to 1 ⁇ m.
  • each electron transport layer may be replaced by a layer structure of an electron injection layer or an electron transport layer / electron injection layer.
  • the layer having the function of blocking transport of such holes is a layer having a hole blocking layer and It may be called.
  • That the hole blocking layer has a function of blocking the transport of holes can produce, for example, an organic EL element in which only a hole current flows, and the blocking effect can be confirmed by the decrease of the current value.
  • the hole injection layer and / or the hole transport layer has a function of blocking the transport of electrons
  • these layers may be referred to as an electron block layer. That the electron blocking layer has a function to block the transport of electrons makes it possible, for example, to fabricate an organic EL element that allows only electron current to flow, and to confirm the effect of blocking the transport of electrons by the decrease of the measured current value.
  • an electron blocking layer may be provided between the anode and the light emitting layer separately from the hole injecting layer and / or the hole transporting layer.
  • the organic EL element may have a single light emitting layer or two or more light emitting layers.
  • structural unit A when a laminate disposed between an anode and a cathode is referred to as “structural unit A”, an organic EL device having two light emitting layers As a structure, the layer structure shown to following d) can be mentioned.
  • the layer configurations of two (structural unit A) may be the same as or different from each other.
  • the charge generation layer is a layer that generates holes and electrons by applying an electric field.
  • the charge generation layer there can be mentioned, for example, a thin film made of vanadium oxide, indium tin oxide (abbreviated as ITO), molybdenum oxide or the like.
  • (Structural unit A) / charge generation layer” is “structural unit B”
  • the layer configuration shown in the following e) can be mentioned as the configuration of the organic EL element having three or more light emitting layers 13.
  • Anode / (Structural unit B) x / (Structural unit A) / Cathode The symbol “x” represents an integer of 2 or more, and “(Structural unit B) x” is an x-stage stack of (Structural unit B) Represents a stacked body.
  • the layer configurations of a plurality of (structural unit B) may be the same or different.
  • a plurality of light emitting layers may be stacked directly to form an organic EL element without providing a charge generation layer.
  • the cathode may be disposed on the substrate side.
  • layers may be stacked on the substrate sequentially from the cathode (right side of each configuration a) to c)).
  • the organic electroluminescent element of this embodiment can be used for an organic electroluminescent display.
  • Example 1 As shown in FIG. 1 as Example 1, manufacture of an organic EL device in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, a first layer, a second layer, and a cathode are sequentially stacked on a substrate did.
  • the organic EL element of Example 1 is referred to as an organic EL element A1.
  • the organic EL element A1 is sealed with glass.
  • the manufacturing method of an organic EL element is demonstrated concretely.
  • a glass substrate was prepared as a substrate of the organic EL element.
  • An ITO thin film was formed in a predetermined pattern as an anode on a glass substrate.
  • the ITO thin film was formed by sputtering.
  • the thickness of the ITO thin film was 45 nm.
  • the glass substrate having the ITO thin film formed on the surface was ultrasonically washed in this order with an organic solvent, an alkaline detergent and ultrapure water, and then boiled in an organic solvent for 10 minutes and dried. Next, ultraviolet ozone treatment was performed for about 15 minutes on the surface on which the ITO thin film is formed using an ultraviolet ozone (UV-O3) apparatus.
  • UV-O3 ultraviolet ozone
  • a hole injection material which is a combination of an organic material having charge transportability and an electron accepting material, was applied on the ITO thin film by spin coating to form a coating film having a thickness of 35 nm.
  • the hole injection material used in Example 1 is referred to as a hole injection material ⁇ 1.
  • the glass substrate provided with the above-mentioned coating film was dried on a hot plate to form a hole injection layer. In the drying using a hot plate, first, it was dried at 80 ° C. for 4 minutes, and further dried at 230 ° C. for 15 minutes.
  • ⁇ Hole transport layer> A hole transport material which is a polymeric material and xylene were mixed to obtain a composition for forming a hole transport layer having a solid (hole transport material) concentration of 0.7% by mass.
  • the hole transport material used in Example 1 is referred to as a hole transport material ⁇ 2.
  • the obtained composition for forming a hole transport layer was applied on the hole injection layer by a spin coating method to obtain a coating film having a thickness of 20 nm.
  • the solvent is evaporated by heating the glass substrate provided with this coating film at a temperature of 200 ° C. for 30 minutes using a hot plate under a nitrogen atmosphere (inert atmosphere), and then naturally cooled to room temperature. I got the transport layer.
  • ⁇ Light emitting layer> The light emitting conjugated polymer material and xylene were mixed to obtain a composition for forming a light emitting layer in which the concentration of the light emitting conjugated polymer material was 1.3%.
  • a blue light emitting conjugated polymer material was used as the light emitting conjugated polymer material.
  • the blue light emitting conjugated polymer material used in Example 1 is referred to as a blue light emitting conjugated polymer material ⁇ 3.
  • the obtained composition for forming a light emitting layer was applied onto the hole transport layer by a spin coating method to obtain a coating film having a thickness of 60 nm.
  • the solvent is evaporated by heating the glass substrate provided with this coating film at 180 ° C. for 10 minutes using a hot plate under a nitrogen atmosphere (inert atmosphere), and then naturally cooled to room temperature to obtain a light emitting layer. I got
  • the glass substrate on which the light emitting layer was formed was transferred to a deposition chamber, and a first layer was formed on the light emitting layer.
  • the vacuum chamber in the deposition chamber is evacuated to 1.0 ⁇ 10 ⁇ 5 Pa or less, and 8-quinolinolato sodium (Naq) represented by the following formula is vacuum evaporated onto the light emitting layer.
  • Naq 8-quinolinolato sodium
  • the deposition rate was 0.3 ⁇ / s.
  • TSBF represented by the following formula, which is the first material
  • barium which is the second material
  • the cathode was formed in a metal-deposition chamber dedicated to metal. Specifically, aluminum was vapor-deposited on the second layer by a vacuum vapor deposition method to form a cathode having a thickness of 100 nm. Thus, the organic EL element A1 was completed.
  • the organic EL element A1 is transported from the vapor deposition chamber to the sealing treatment chamber without being exposed to the atmosphere, and a sealing glass in which a UV curing resin is applied to the periphery under a nitrogen atmosphere (inert atmosphere) Then, a UV curable resin was cured by bonding the glass substrate transferred from the deposition chamber and irradiating the UV light, and the organic EL element A1 was sealed with glass.
  • the driving voltage was measured by driving the organic EL element A1 manufactured as described above.
  • the driving voltage is a voltage when driving the organic EL element A1 at a constant current of 10 mA / cm 2 .
  • the driving voltage of the organic EL element A1 was 3.4V.
  • Comparative Example 1 As Comparative Example 1, an organic EL element B1 described in the prior art (Japanese Patent No. 4514841) was produced. The organic EL element B1 was produced by the same method as the organic EL element A1 except that the second layer was not formed. The produced organic EL element B1 was glass-sealed in the same manner as in Example 1.
  • the organic EL element B1 of Comparative Example 1 was driven, and the driving voltage was measured under the same conditions as in Example 1.
  • the driving voltage of the organic EL element B1 was 7.9 V.
  • Comparative Example 2 As Comparative Example 2, an organic EL element C1 was produced.
  • the organic EL element C1 was manufactured by the same method as the organic EL element A1, except that a barium single layer was formed instead of the second layer in the organic EL element A1.
  • barium single layer formed metal barium on the first layer by a vacuum evaporation method (deposition rate: 0.3 ⁇ / s) in a vacuum chamber evacuated to 1.0 ⁇ 10 ⁇ 5 Pa or less. It was formed by film formation. The film thickness of the barium monolayer was 1 nm.
  • the produced organic EL element C1 was glass-sealed in the same manner as in Example 1.
  • the organic EL element C1 of Comparative Example 2 was driven, and the driving voltage was measured under the same conditions as in Example 1.
  • the drive voltage of the organic EL element C1 was 6.6V.
  • the organic EL element D1 is an organic EL element A1 except that a barium single layer, a TSBF single layer and a sodium fluoride layer are formed in this order on the first layer instead of the second layer in the organic EL element A1. It was prepared by the same method as in.
  • the barium monolayer, TSBF monolayer, and sodium fluoride layer are 0.3 ⁇ / s and 1.0 ⁇ / s, respectively, by vacuum evaporation in a vacuum chamber evacuated to 1.0 ⁇ 10 ⁇ 5 Pa or less. It was formed at a deposition rate of s and 0.3 ⁇ / s.
  • the thicknesses of the barium monolayer, TSBF monolayer and sodium fluoride layer were 1 nm, 10 nm and 3 nm, respectively.
  • the produced organic EL element D1 was glass-sealed in the same manner as in Example 1.
  • the organic EL element D1 of Comparative Example 3 was driven, and the driving voltage was measured under the same conditions as in Example 1.
  • the drive voltage of the organic EL element D1 was 7.0V.
  • Example 2 organic EL element A2 was produced.
  • Organic EL element A2 was produced by the same method as organic EL element A1 of Example 1 except that the first layer contained TSBF.
  • the first layer in the organic EL element A2 was formed by co-evaporation of Naq and TSBF on the light emitting layer by vacuum evaporation.
  • the deposition rate of Naq was 0.5 ⁇ / s
  • the deposition rate of TSBF was 0.5 ⁇ / s.
  • the first layer contained 50% by volume of Naq and 50% by volume of TSBF.
  • the thickness of the first layer in the organic EL element A2 was 2 nm.
  • the produced organic EL element A2 was glass-sealed in the same manner as in Example 1.
  • the driving voltage was measured under the same conditions as in Example 1 by driving the organic EL element A2 in Example 2.
  • the driving voltage of the organic EL element A2 was 3.8V.
  • Example 3 organic EL element A3 was produced.
  • the organic EL device A3 was manufactured in the same manner as in Example 2, except that the deposition rate of Naq was 0.8 ⁇ / s at the time of formation of the first layer, and the deposition rate of TSBF was 0.2 ⁇ / s. It was made.
  • the produced organic EL element A3 was glass-sealed in the same manner as in Example 1. At this time, the first layer contains 80% by volume of Naq and 20% by volume of TSBF.
  • the driving voltage was measured under the same conditions as in Example 1 by driving the organic EL element A3 in Example 3.
  • the drive voltage of the organic EL element A3 was 3.5V.
  • Table 2 shows the measurement results of the drive voltages of the above-described Examples 1 to 3 and Comparative Example 1.
  • Example 4 organic EL element A4 was produced.
  • the organic EL element A4 was produced by the same method as the organic EL element A1, except that calcium was used instead of barium as the second material in the second layer.
  • the second layer in the organic EL element A4 was formed by co-evaporation of TSBF and calcium metal by vacuum evaporation. The film thickness of the second layer was 10 nm. At this time, the deposition rate of TSBF was 0.9 ⁇ / s, and the deposition rate of calcium was 0.1 ⁇ / s. At this time, the second layer contained 90% by volume of TSBF and 10% by volume of calcium.
  • the produced organic EL element A4 was glass-sealed in the same manner as in Example 1.
  • the driving voltage was measured under the same conditions as in Example 1 by driving the organic EL element A4 in Example 4.
  • the driving voltage of the organic EL element A4 was 3.8V.
  • Example 5 organic EL element A5 was produced.
  • the organic EL element A5 was produced by the same method as the organic EL element A1 except that 8-quinolinolatolithium (Liq) was used in place of Naq as the first layer.
  • the first layer in the organic EL element A5 was formed on the light emitting layer by vapor deposition of Liq by a vacuum vapor deposition method (vapor deposition rate: 0.3 ⁇ / s).
  • the film thickness of the first layer was 1 nm.
  • the produced organic EL element A5 was glass-sealed in the same manner as in Example 1.
  • the organic EL element A5 of Example 5 was driven, and the driving voltage was measured under the same conditions as in Example 1.
  • the driving voltage of the organic EL element A5 was 4.1V.
  • Comparative Example 4 As Comparative Example 4, an organic EL element F1 described in the prior art (Japanese Patent No. 4514841) was produced. The organic EL element F1 was produced by the same method as the organic EL element A5 except that the second layer was not formed. The produced organic EL element F1 was glass-sealed in the same manner as in Example 1.
  • the organic EL element F1 of Comparative Example 4 was driven, and the driving voltage was measured under the same conditions as in Example 1.
  • the drive voltage of the organic EL element F1 was 7.8V.
  • SYMBOLS 1 Organic EL element, 11 ... Hole injection layer, 12 ... Hole transport layer, 13 ... Light emitting layer, 14a ... 2nd layer, 14b ... 1st layer, E1 ... anode, E2 ... cathode.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un élément électroluminescent organique comprenant une électrode positive, une couche émettrice de lumière qui est disposée sur l'électrode positive, une première couche qui est disposée sur la couche émettrice de lumière, une seconde couche qui est disposée sur la première couche, et une électrode négative qui est disposée sur la seconde couche. Le présent élément électroluminescent organique est conçu de sorte que : la première couche contient un complexe métallique organique qui contient au moins un élément choisi dans le groupe constitué par des éléments de métal alcalin, des éléments de métal alcalino-terreux et des éléments de métal des terres rares ; et la seconde couche contient un composé organique de transport d'électrons, et un métal alcalin et/ou un métal alcalino-terreux.
PCT/JP2018/040884 2017-11-02 2018-11-02 Élément électroluminescent organique WO2019088262A1 (fr)

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Citations (4)

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JP2011508421A (ja) * 2007-12-19 2011-03-10 グローバル・オーエルイーディー・テクノロジー・リミテッド・ライアビリティ・カンパニー 低電圧エレクトロルミネッセンスデバイス用の有機素子
JP2013524438A (ja) * 2010-03-31 2013-06-17 ゼネラル・エレクトリック・カンパニイ 発光デバイスおよび物品
WO2015115530A1 (fr) * 2014-01-31 2015-08-06 出光興産株式会社 Composé, matériau pour des éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
JP2016540381A (ja) * 2013-11-17 2016-12-22 ソルヴェイ（ソシエテ アノニム） 隣接層にｓｂｆマトリックス材料を有する多層構造体

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JP4514841B2 (ja) 1998-02-17 2010-07-28 淳二 城戸 有機エレクトロルミネッセント素子
US20050025993A1 (en) * 2003-07-25 2005-02-03 Thompson Mark E. Materials and structures for enhancing the performance of organic light emitting devices
JP5573127B2 (ja) * 2009-11-27 2014-08-20 セイコーエプソン株式会社 発光素子、表示装置および電子機器
JP2017022299A (ja) * 2015-07-14 2017-01-26 住友化学株式会社 有機ｅｌ素子

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JP2011508421A (ja) * 2007-12-19 2011-03-10 グローバル・オーエルイーディー・テクノロジー・リミテッド・ライアビリティ・カンパニー 低電圧エレクトロルミネッセンスデバイス用の有機素子
JP2013524438A (ja) * 2010-03-31 2013-06-17 ゼネラル・エレクトリック・カンパニイ 発光デバイスおよび物品
JP2016540381A (ja) * 2013-11-17 2016-12-22 ソルヴェイ（ソシエテ アノニム） 隣接層にｓｂｆマトリックス材料を有する多層構造体
WO2015115530A1 (fr) * 2014-01-31 2015-08-06 出光興産株式会社 Composé, matériau pour des éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

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