WO2012029936A1 - Élément électroluminescent organique et son procédé de production - Google Patents

Élément électroluminescent organique et son procédé de production Download PDF

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WO2012029936A1
WO2012029936A1 PCT/JP2011/069984 JP2011069984W WO2012029936A1 WO 2012029936 A1 WO2012029936 A1 WO 2012029936A1 JP 2011069984 W JP2011069984 W JP 2011069984W WO 2012029936 A1 WO2012029936 A1 WO 2012029936A1
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layer
organic
thin film
light emitting
electrode
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PCT/JP2011/069984
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Japanese (ja)
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秀信 柿本
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住友化学株式会社
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour

Definitions

  • the present invention relates to an organic electroluminescence element and a manufacturing method thereof.
  • organic EL displays using organic electroluminescence (hereinafter sometimes referred to as “organic EL”) elements have attracted attention.
  • An organic EL element used for an organic EL display includes an anode, a cathode, and an organic layer such as a light emitting layer disposed between the anode and the cathode, and is injected from the anode and the cathode, respectively. Holes and electrons emit light by being combined in the light emitting layer.
  • the organic EL element Since an organic layer such as a light emitting layer can be formed by a coating method, the organic EL element has an advantage that the manufacturing process is simple and the area can be easily increased.
  • the organic layer can be formed by applying an organic solution containing an organic compound to form a film, and then drying the formed applied film.
  • a method for drying the coating film it is known to perform a heat treatment in an inert gas atmosphere (Patent Document 1) or to dry the coating film in a vacuum (Patent Document 2).
  • An object of the present invention is to provide a method for producing an organic EL element whose luminance half-life is extended as compared with an organic EL element produced by a conventional method, an organic EL element produced by the production method, and a surface provided with the organic EL element A light source, an illumination device, and a display device.
  • the present inventor has intensively studied. As a result, the luminance half-life of the organic EL element is improved by baking an organic compound-containing thin film in an atmosphere containing a reducing gas to form an organic layer. As a result, the present invention has been completed.
  • the present invention is a method for manufacturing an organic electroluminescent element having a first electrode, a second electrode, and an organic layer provided between the first electrode and the second electrode.
  • the organic layer is formed by forming a thin film containing an organic compound and firing the thin film in an atmosphere containing a reducing gas at a volume fraction of 0.1% or more.
  • a manufacturing method is provided.
  • the atmosphere containing the reducing gas is an atmosphere having an oxygen concentration of 10 ppm or less by volume fraction and / or a water concentration of 10 ppm or less by volume fraction.
  • the firing is performed in a temperature range of 50 ° C to 250 ° C.
  • the first electrode is an anode.
  • the thin film containing the organic compound is formed by a solution coating method.
  • the said organic layer is a light emitting layer.
  • the said organic electroluminescent element further has the functional layer provided between the 1st electrode and the light emitting layer, or between the 2nd electrode and the light emitting layer.
  • the said organic electroluminescent element further has a functional layer provided between the said 1st electrode and the light emitting layer.
  • the organic compound is a polymer compound.
  • the present invention provides an organic electroluminescence device manufactured by any one of the above-described organic electroluminescence device manufacturing methods.
  • the present invention provides a planar light source comprising the organic electroluminescence element.
  • This invention provides a display apparatus provided with the said organic electroluminescent element.
  • the present invention provides an illuminating device including the organic electroluminescence element.
  • an organic EL element having a luminance half life extended as compared with an organic EL element produced by a conventional method is produced.
  • the organic EL element of the present invention with an extended luminance half-life is used for planar or curved surface light sources used for illumination, display devices such as segment display devices and dot matrix display devices, backlights for liquid crystal display devices, etc. Preferably used.
  • FIG. 1 is a cross-sectional view schematically showing one embodiment of the structure of an organic EL element manufactured by the method of the present invention.
  • the organic EL element 1 has a first electrode 3, a second electrode 7, and a light emitting layer 6 provided between the first electrode and the second electrode on a substrate 2. is doing.
  • the first electrode 3 in the organic EL element 1 is an anode
  • the second electrode 7 is a cathode
  • the light emitting layer is formed, for example, by forming a thin film containing an organic compound having a light emitting function on the anode and firing the thin film.
  • a thin film containing an organic compound can be formed by a film forming method such as a vapor deposition method or a solution coating method. From the viewpoint of ease of manufacturing the organic EL element, the thin film is preferably formed by a solution coating method.
  • the “solution coating method” is a method in which a solution or dispersion of an organic compound is applied onto an article, and then the solution or dispersion is solidified so that the organic compound becomes a film that does not exhibit fluidity. Means the way
  • Solvents used for film formation from the solution coating method include chlorine-based solvents such as chloroform, methylene chloride and dichloroethane, ether-based solvents such as tetrahydrofuran, toluene, xylene, anisole, 1,2,3,4-tetrahydronaphthalene (tetralin (Registered trademark)), aromatic hydrocarbon solvents such as phenylcyclohexane, ketone solvents such as acetone and methyl ethyl ketone, and ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate. A mixture may be used.
  • chlorine-based solvents such as chloroform, methylene chloride and dichloroethane
  • ether-based solvents such as tetrahydrofuran, toluene, xylene, anisole, 1,2,3,4-tetrahydronaphthalene (tetralin (
  • Solution coating methods include spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, slit coating, capillary coating, and spray coating.
  • a coating method such as a method and a nozzle coating method
  • a printing method such as 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.
  • a printing method such as a gravure printing method, a screen printing method, a flexographic printing method, an offset printing method, a reverse printing method, and an ink jet printing method is preferable in that pattern formation and multicolor coating are easy.
  • the thin film may be formed in an atmosphere containing an inert gas or in an air atmosphere.
  • the thin film is formed under an atmosphere in which the concentration of the inert gas in the atmosphere is equal to or higher than the concentration of the inert gas contained in the atmosphere.
  • the inert gas include helium gas, argon gas, nitrogen gas, and a mixed gas thereof. Among these, nitrogen gas is preferable from the viewpoint of ease of device fabrication.
  • the thin film is preferably formed in an atmosphere in which oxygen is 1000 ppm or less in volume fraction and / or moisture is 1000 ppm or less in volume fraction, and oxygen is 10 ppm or less in volume fraction and More preferably, the moisture is formed in an atmosphere having a volume fraction of 10 ppm or less.
  • the formation of the thin film may be performed under a reduced pressure atmosphere. This is because gas hardly remains in the formed thin film, and the possibility that oxygen is contained in the thin film is reduced.
  • the pressure in the thin film forming step is about 10 Pa or less, and preferably about 10 ⁇ 7 to 10 ⁇ 3 Pa.
  • the thin film firing step is usually performed following the thin film formation step.
  • One embodiment of the present invention includes a step of forming the thin film over the first electrode and baking the thin film in an atmosphere containing a reducing gas.
  • the term “reducing gas” refers to a gas that itself has reducibility to oxygen or ozone, or a gas that decomposes itself to generate a gas that has reducibility to oxygen or ozone. means.
  • the reducing gas include ammonia gas, carbon monoxide gas, and hydrogen gas.
  • the solvent contained in the thin film can be removed, and the oxide or oxygen present in or on the thin film can be reduced to reduce the oxide or The amount of oxygen can be reduced.
  • an oxide or oxygen is present in the organic layer included in the organic EL element, characteristic deterioration due to charge traps caused by a small amount of oxide, or characteristic deterioration due to oxidation of the metal used for the cathode may occur. .
  • By performing a simple process of firing in an atmosphere containing a reducing gas it is possible to suppress deterioration in characteristics of the organic EL element due to the presence of oxides and oxygen.
  • Charge trapping and cathode oxidation reduce the amount of holes and electrons, inactivate the bonding reaction between holes and electrons, and directly affect the light emitting function of the light emitting layer.
  • the atmosphere in which the thin film is fired preferably contains a reducing gas in a volume fraction of 0.1% or more.
  • the reducing gas contains 1% or more by volume fraction, more preferably the reducing gas contains 10% or more by volume fraction, It is more preferable that the gas has a volume fraction of 50% or more, and it is particularly preferable that the reducing gas contain a volume fraction of 90% or more.
  • the atmosphere in which the firing step in the present invention is performed is preferably, from the viewpoint of the light emission characteristics and lifetime characteristics of the device, the oxygen concentration is 1000 ppm or less by volume fraction and / or the moisture concentration is 1000 ppm or less by volume fraction, More preferably, the oxygen concentration is 100 ppm or less by volume fraction and / or the water concentration is 100 ppm or less by volume fraction, and the oxygen concentration is 10 ppm or less by volume fraction and / or the water concentration is 10 ppm or less by volume fraction. More preferably it is.
  • the atmosphere in which the firing step is performed may contain an inert gas.
  • the inert gas include helium gas, argon gas, nitrogen gas, and a mixed gas thereof.
  • the inert gas is preferably nitrogen gas from the viewpoint of ease of device fabrication.
  • the thin film may be fired under a reduced pressure atmosphere. This is because even if oxygen remains in the thin film, it is easily removed.
  • the pressure of the atmosphere in the thin film baking step is about 10 Pa or less, and is preferably adjusted to about 10 ⁇ 7 to 10 ⁇ 3 Pa.
  • the firing step in the present invention is preferably performed at a temperature within the range of 50 ° C. to 250 ° C., preferably at a temperature within the range of 50 ° C. to 200 ° C., from the viewpoint of the light emission characteristics and lifetime characteristics of the device. It is more preferable.
  • the firing time is appropriately selected depending on the organic compound contained in the thin film, and is usually about 5 minutes to 2 hours.
  • an organic EL element is manufactured by forming a cathode on the light emitting layer.
  • FIG. 2 is a cross-sectional view schematically showing another embodiment of the structure of the organic EL element of the present invention.
  • the organic EL element 1 ′ includes a first electrode 3, a second electrode 7, and a light emitting layer 6 provided between the first electrode and the second electrode on a substrate 2. Have. And it further has the 1st functional layer 4 and the 2nd functional layer 5 which were provided between the 1st electrode 3 and the light emitting layer 6.
  • the formation process of the light emitting layer 6, the 1st functional layer 4, and the 2nd functional layer 5 is demonstrated taking the organic EL element shown in FIG. 2 as an example, and the detail of the other component of an organic EL element is mentioned later. To do.
  • the light emitting layer 6 is an organic layer containing an organic compound, and has the same function and formation method as the light emitting layer 6 in the organic EL element 1 described above.
  • the first functional layer 4 and the second functional layer 5 may be an organic layer containing an organic compound or an inorganic layer made of an inorganic compound. When these are organic layers, the first functional layer 4 or the second functional layer 5 is formed in the same manner as the light emitting layer 6 in the organic EL element 1 described above.
  • These organic layers are formed on the surface of the first electrode and on the surface of the layer farthest from the first electrode among one or more layers provided on the first electrode.
  • the latter case includes, for example, a case where an organic layer is formed on the surface of the hole injection layer or hole transport layer provided on the first electrode.
  • the functional layer means a layer having a function of improving device characteristics such as charge injection or transport.
  • a hole injection layer, a hole transport layer, a hole block layer, an electron injection layer, an electron transport layer, an electron block layer, and the like correspond to the functional layer.
  • the first electrode 3 is an anode
  • the second electrode 7 is a cathode
  • the first functional layer 4 is a hole injection layer
  • the second functional layer 5 is It is a hole transport layer.
  • an electron injection layer, an electron transport layer, or the like may be formed as a functional layer between the light emitting layer 6 and the cathode (that is, the second electrode 7).
  • the hole transport layer is formed on the hole injection layer by forming a thin film containing an organic compound having a hole transport function, and firing the thin film.
  • a solution containing the organic compound is applied to form a thin film containing an organic compound.
  • the organic compound is preferably a polymer compound.
  • the solvent and the coating method for forming the thin film by the solution coating method are the same as those of the light emitting layer 6 in the organic EL element 1 described above.
  • the thin film containing an organic compound is preferably formed under atmospheric pressure and an atmosphere containing an inert gas from the viewpoint that an organic EL element can be easily produced.
  • the inert gas include helium gas, argon gas, nitrogen gas, and a mixed gas thereof. Among these, nitrogen gas is preferable from the viewpoint of ease of device fabrication.
  • the atmosphere in which the thin film is formed may be an air atmosphere, or the inert gas concentration may be 99% or more by volume ratio. From the viewpoint of extending the device life, the thin film is preferably formed in an atmosphere having an inert gas concentration of 99.5% or more.
  • the atmosphere in which the thin film is formed is preferably an oxygen concentration of 1000 ppm or less in terms of volume fraction and / or a moisture concentration of 1000 ppm or less in terms of volume fraction, from the viewpoint of device fabrication. More preferably, the volume fraction is 10 ppm or less and / or the water concentration is 10 ppm or less by volume fraction.
  • the thin film is fired in a state where the oxygen concentration and moisture concentration in the atmosphere are each kept at 1000 ppm or less by volume fraction. By this firing, the solvent contained in the thin film is removed.
  • Calcination is preferably performed at a temperature in the range of 50 ° C. to 250 ° C., more preferably in a range of 50 ° C. to 200 ° C., from the viewpoint of the light emission characteristics and lifetime characteristics of the device.
  • the firing time is appropriately selected depending on the organic compound contained in the thin film, and is usually about 5 minutes to 2 hours.
  • the thin film is fired in an atmosphere containing an inert gas and / or an atmosphere containing a reducing gas, or in an atmosphere having a pressure of 10 Pa or less.
  • the inert gas include helium gas, argon gas, nitrogen gas, and a mixed gas thereof.
  • nitrogen gas is preferable from the viewpoint of ease of device fabrication.
  • the reducing gas include ammonia gas, carbon monoxide gas, and hydrogen gas.
  • the formation of the thin film and the firing of the thin film are preferably performed in a state in which the oxygen concentration and the moisture concentration in the atmosphere are each kept at 600 ppm or less in terms of volume fraction from the viewpoint of the light emission characteristics and lifetime characteristics of the device. More preferably, the oxygen concentration and the water concentration are each 300 ppm or less in volume fraction, more preferably the oxygen concentration and the water concentration are each 100 ppm or less in volume fraction, and particularly preferably the oxygen concentration and the water concentration. Are 10 ppm or less in volume fractions, respectively.
  • an organic EL device is manufactured by forming a light emitting layer on the hole transport layer and further forming a cathode thereon.
  • the organic EL element of the present invention has a first electrode, a second electrode, and an organic layer (for example, a light emitting layer) disposed between the first electrode and the second electrode as essential constituent requirements. is doing.
  • an organic layer for example, a light emitting layer
  • a functional layer is further provided between the first electrode (for example, anode) and the second electrode (for example, cathode), for example, in order to improve device characteristics. Good.
  • Examples of the functional layer provided between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer.
  • the layer in contact with the cathode is called the electron injection layer
  • the layers other than the electron injection layer are called the electron transport layer.
  • the electron injection layer is a layer having a function of improving the electron injection efficiency from the cathode.
  • the electron transport layer is a layer having a function of improving electron injection from the cathode, the electron injection layer, or the electron transport layer closer to the cathode to the adjacent layer.
  • the hole blocking layer is a layer having a function of blocking hole transport. In the case where the electron injection layer and / or the electron transport layer have a function of blocking hole transport, these layers may also serve as the hole blocking layer.
  • the hole blocking layer has a function of blocking hole transport
  • an element that allows only a hole current to flow For example, an element that does not include a hole blocking layer and allows only a hole current to flow (referred to as a “blank element”) and an element having a structure in which a hole blocking layer is inserted into the blank element are manufactured. It can be confirmed that the hole blocking layer exhibits a function of blocking hole transport by reducing the current value of the element including the hole blocking layer with respect to the current value.
  • Examples of the functional layer provided between the anode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron block layer.
  • the layer in contact with the anode is called a hole injection layer, and the layers other than the hole injection layer are positive.
  • a hole transport layer sometimes referred to as a hole transport layer.
  • the hole injection layer is a layer having a function of improving hole injection efficiency from the anode.
  • the hole transport layer is a layer having a function of improving hole injection from the anode, the hole injection layer, or the hole transport layer closer to the anode.
  • the electron blocking layer is a layer having a function of blocking electron transport. In the case where the hole injection layer and / or the hole transport layer has a function of blocking electron transport, these layers may also serve as an electron blocking layer.
  • the electron block layer has a function of blocking electron transport
  • an element that allows only electron current to flow for example, an element that does not include an electronic block layer and that allows only an electronic current to flow (also referred to as a “blank element”) and an element that has an electronic block layer inserted into the blank element are manufactured, and the current value of the blank element It can be confirmed that the electron blocking layer has a function of blocking electron transport by reducing the current value of the element including the electron blocking layer.
  • An example of an element configuration that can be taken by the organic EL element of the present embodiment is shown below.
  • the symbol “/” indicates that the layers sandwiching the symbol “/” are stacked adjacent to each other.
  • a) Anode / hole injection layer / light emitting layer / cathode b) Anode / hole injection layer / light emitting layer / electron injection layer / cathode c) Anode / hole injection layer / light emitting layer / electron transport layer / cathode e) Anode / Hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode f) anode / hole transport layer / light emitting layer / cathode d) anode / hole transport layer / light emitting layer / electron injection layer / cathode e) Anode / hole transport layer / light emitting layer / electron transport layer / cathode e) Anode / hole transport
  • the organic EL element may have two or more light emitting layers.
  • a layer (when only one layer is present) or a group of layers (when two or more layers are present) provided between the anode and the cathode is referred to as “repeating unit A”, respectively.
  • the element configuration shown in the following n) can be exemplified.
  • (repeat unit A) / charge generation layer” is “repeat unit B”
  • an organic EL device having three or more light-emitting layers is specifically exemplified by the device configuration shown in o) below. be able to.
  • the charge generation layer is a layer in which holes and electrons are generated by applying an electric field.
  • Examples of the charge generation layer include a thin film made of vanadium oxide, indium tin oxide (IndiumInTin Oxide: abbreviation ITO), molybdenum oxide, or the like.
  • the organic EL element may be further covered with a sealing member such as a sealing film or a sealing plate for sealing.
  • a sealing member such as a sealing film or a sealing plate for sealing.
  • all the layers arranged on the side from which the light is extracted are usually transparent with respect to the light emitting layer.
  • the degree of transparency is preferably such that the visible light transmittance between the outermost surface of the organic EL element from which light is extracted and the light emitting layer is 40% or more.
  • an organic EL element that is required to emit light in the ultraviolet region or infrared region one that exhibits a light transmittance of 40% or more in the region is preferable.
  • an insulating layer having a thickness of 2 nm or less may be provided adjacent to the electrode in order to further improve the adhesion with the electrode or improve the charge injection property from the electrode.
  • a thin buffer layer may be inserted between the above-described layers in order to improve adhesion at the interface or prevent mixing.
  • the order of the layers to be laminated, the number of layers, and the thickness of each layer can be appropriately set in consideration of the light emission efficiency and the element lifetime.
  • a substrate that is not chemically changed in the process of manufacturing the organic EL element is suitably used.
  • a glass, a plastic, a polymer film, a silicon substrate, and a laminate of these are used.
  • a commercially available substrate can be used as the substrate, and it can be produced by a known method.
  • Examples of a method for producing the anode include a vacuum deposition method, a sputtering method, an ion plating method, and a plating method. Further, an organic transparent conductive film such as polyaniline or a derivative thereof, polythiophene or a derivative thereof may be used as the anode.
  • a material that reflects light may be used for the anode, and the material is preferably a metal, metal oxide, or metal sulfide having a work function of 3.0 eV or more.
  • the thickness of the anode can be appropriately selected in consideration of light transmittance and electric conductivity, and is, for example, 10 nm to 10 ⁇ m, preferably 20 nm to 1 ⁇ m, and more preferably 40 nm to 500 nm. .
  • ⁇ Hole injection layer> As the hole injection material constituting the hole injection layer, inorganic oxides such as vanadium oxide, molybdenum oxide, ruthenium oxide, and aluminum oxide, phenylamine and derivatives thereof, starburst type amine derivatives, phthalocyanine and derivatives thereof, Mention may be made of organic compounds such as amorphous carbon, polyaniline, and polythiophene and its derivatives.
  • Examples of the method for forming the hole injection layer include a method in which a thin film containing a hole injection material is formed and then fired or dried.
  • Examples of the method for forming a thin film containing a hole injection material include film formation from a solution containing a hole injection material. From the viewpoint of extending the lifetime, the atmosphere is the same as that of the organic layer formation step described above. It is preferable to form a film below.
  • the solvent used for film formation from a solution is not particularly limited as long as it dissolves the hole injection material.
  • Chlorine solvents such as chloroform, methylene chloride, dichloroethane, ether solvents such as tetrahydrofuran, toluene, xylene , Aromatic hydrocarbon solvents such as anisole, tetralin and phenylcyclohexane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, alcohol solvents such as isopropyl alcohol, and Water can be mentioned, and a mixture of these may be used.
  • Aromatic hydrocarbon solvents such as anisole, tetralin and phenylcyclohexane
  • ketone solvents such as acetone and methyl ethyl ketone
  • ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate
  • Application methods such as a screen printing method, a flexographic printing method, an offset printing method, an ink jet printing method, and a gravure printing method can be given.
  • the film thickness of the hole injection layer varies depending on the material used, and is set as appropriate so that the drive voltage and light emission efficiency are appropriate. If it is thick, the driving voltage of the element increases, which is not preferable. Therefore, the thickness of the hole injection layer 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 material constituting the hole transport layer examples include polyvinyl carbazole or a derivative thereof, polysilane or a derivative thereof, a polysiloxane derivative having an aromatic amine residue in a side chain or a main chain, a pyrazoline derivative, an arylamine derivative, a stilbene. Derivative, triphenyldiamine derivative, polyaniline or derivative thereof, polythiophene or derivative thereof, polyarylamine or derivative thereof, polypyrrole or derivative thereof, poly (p-phenylene vinylene) or derivative thereof, or poly (2,5-thienylene vinylene) ) Or a derivative thereof.
  • hole transport materials include polyvinyl carbazole or derivatives thereof, polysilane or derivatives thereof, polysiloxane derivatives having aromatic amine residues in the side chain or main chain, polyaniline or derivatives thereof, polythiophene or derivatives thereof, poly Polymeric hole transport materials such as arylamine or derivatives thereof, poly (p-phenylene vinylene) or derivatives thereof, or poly (2,5-thienylene vinylene) or derivatives thereof are preferred, and polyvinylcarbazole or derivatives thereof are more preferred. , Polysilane or a derivative thereof, and a polysiloxane derivative having an aromatic amine residue in the side chain or main chain. In the case of a low-molecular hole transport material, it is preferably used by being dispersed in a polymer binder.
  • the hole transport layer may be formed by the same method as the hole transport layer 5 included in the organic EL element 1 ′.
  • the method for forming a thin film containing a hole transport material is not particularly limited, but for a low molecular hole transport material, film formation from a mixed liquid containing a polymer binder and a hole transport material may be mentioned. In the case of a polymer hole transport material, film formation from a solution containing the hole transport material can be given.
  • the solvent used for film formation from a solution is not particularly limited as long as it can dissolve a hole transport material.
  • Chlorine solvents such as chloroform, methylene chloride, dichloroethane, ether solvents such as tetrahydrofuran, toluene, xylene , Aromatic hydrocarbon solvents such as anisole, tetralin and phenylcyclohexane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, etc. You may use what you did.
  • Examples of the film formation method from a solution include the same application method as the above-described film formation method of the hole injection layer. From the viewpoint of extending the life, an atmosphere suitable for performing the organic layer formation step described above. It is preferable to form a film in the same atmosphere as in FIG.
  • polystyrene examples include vinyl chloride and polysiloxane.
  • the light emitting layer is usually formed of an organic substance that mainly emits fluorescence and / or phosphorescence, or an organic substance and a dopant that assists the organic substance.
  • the dopant is added, for example, in order to improve the luminous efficiency and change the emission wavelength.
  • the organic substance may be a low molecular compound or a high molecular compound, and the light emitting layer preferably contains a high molecular compound having a polystyrene-equivalent number average molecular weight of 10 3 to 10 8 .
  • Examples of the light emitting material constituting the light emitting layer include a polymer material.
  • Polymeric materials include polyparaphenylene vinylene and derivatives thereof, polythiophene and derivatives thereof, polyparaphenylene and derivatives thereof, polysilane and derivatives thereof, polyacetylene and derivatives thereof, polyfluorene and derivatives thereof, polyvinylcarbazole and derivatives thereof, Examples include those obtained by polymerizing metal atom-free dopant materials and metal complex dopant materials, as exemplified in (1).
  • examples of materials that emit blue light include distyrylarylene derivatives, oxadiazole derivatives, and polymers thereof, polyvinylcarbazole derivatives, polyparaphenylene derivatives, and polyfluorene derivatives. Of these, polymer materials such as polyvinyl carbazole derivatives, polyparaphenylene derivatives, and polyfluorene derivatives are preferred.
  • examples of materials that emit red light include coumarin derivatives, thiophene derivatives, and polymers thereof, polyparaphenylene vinylene derivatives, polythiophene derivatives, and polyfluorene derivatives.
  • polymer materials such as polyparaphenylene vinylene derivatives, polythiophene derivatives, and polyfluorene derivatives are preferable.
  • dye-based dopant materials include cyclopentamine derivatives, tetraphenylbutadiene derivatives, triphenylamine derivatives, oxadiazole derivatives, pyrazoloquinoline derivatives, distyrylbenzene derivatives, distyrylarylene derivatives, pyrrole derivatives, thiophene derivatives.
  • metal complex dopant material examples include, for example, Al, Zn, Be or the like as a central metal, or a rare earth metal such as Tb, Eu, or Dy, and an oxadiazole structure, thiadiazole structure, or phenylpyridine as a ligand.
  • Metal complexes having a structure, a phenylbenzimidazole structure, a quinoline structure, and the like.
  • a metal complex exhibiting light emission from a triplet excited state such as an iridium complex, a platinum complex, an aluminum quinolinol complex, a benzoquinolinol beryllium complex, a benzo An oxazolyl zinc complex, a benzothiazole zinc complex, an azomethyl zinc complex, a porphyrin zinc complex, a europium complex, etc. can be mentioned.
  • the thickness of such a light emitting layer is usually about 2 nm to 200 nm.
  • the method for forming the light emitting layer may be the same as the method for forming the light emitting layer 6 included in the organic EL element 1.
  • a method for forming the light emitting layer includes a method of forming a thin film containing a light emitting material and then baking or drying.
  • the thin film is formed from a solution containing a luminescent material.
  • the solvent used for film formation from a solution include the same solvents as those used for forming a hole transport layer from the above solution.
  • the coating method include a coating method such as a coating method, a spray coating method, and a nozzle coating method, and a printing method such as 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.
  • a printing method such as a gravure printing method, a screen printing method, a flexographic printing method, an offset printing method, a reverse printing method, and an ink jet printing method is preferable in that pattern formation and multicolor coating are easy.
  • an electron transport material constituting the electron transport layer an oxadiazole derivative, anthraquinodimethane or a derivative thereof, benzoquinone or a derivative thereof, naphthoquinone or a derivative thereof, anthraquinone or a derivative thereof, tetracyanoanthraquinodimethane or a derivative thereof, Fluorenone derivatives, diphenyldicyanoethylene or derivatives thereof, diphenoquinone derivatives, or metal complexes of 8-hydroxyquinoline or derivatives thereof, polyquinoline or derivatives thereof, polyquinoxaline or derivatives thereof, polyfluorene or derivatives thereof, and the like can be given.
  • oxadiazole derivatives benzoquinone or derivatives thereof, anthraquinones or derivatives thereof, or metal complexes of 8-hydroxyquinoline or derivatives thereof, polyquinoline or derivatives thereof, polyquinoxaline or derivatives thereof, polyfluorene or derivatives thereof are preferred, 2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole, benzoquinone, anthraquinone, tris (8-quinolinol) aluminum, and polyquinoline are more preferable.
  • the electron transport layer can be formed by the same method as the hole transport layer 5 included in the organic EL element 1 '.
  • a vacuum deposition method from a powder or a film formation from a solution or a molten state can be exemplified.
  • the electron transport material include film formation from a solution or a molten state.
  • a polymer binder may be used in combination.
  • the method for forming the electron transport layer from the solution include the same film formation method as the method for forming the hole transport layer from the above-described solution, and an atmosphere suitable for performing the above-described organic layer forming step. It is preferable to form a film in the same atmosphere as in FIG.
  • the film thickness of the electron transport layer varies depending on the material used, and is set appropriately so that the drive voltage and the light emission efficiency are appropriate, and at least a thickness that does not cause pinholes is required, and is too thick. In such a case, the driving voltage of the element increases, which is not preferable. Accordingly, the thickness of the electron transport layer is, for example, 1 nm to 1 ⁇ m, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.
  • an optimum material is appropriately selected according to the type of the light emitting layer, and an alloy containing at least one of alkali metal, alkaline earth metal, alkali metal and alkaline earth metal, alkali A metal or alkaline earth metal oxide, halide, carbonate, a mixture of these substances, or the like can be given.
  • alkali metals, alkali metal oxides, halides, and carbonates include lithium, sodium, potassium, rubidium, cesium, lithium oxide, lithium fluoride, sodium oxide, sodium fluoride, potassium oxide, potassium fluoride , Rubidium oxide, rubidium fluoride, cesium oxide, cesium fluoride, lithium carbonate, and the like.
  • alkaline earth metals, alkaline earth metal oxides, halides and carbonates include magnesium, calcium, barium, strontium, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, barium oxide, Examples thereof include barium fluoride, strontium oxide, strontium fluoride, and magnesium carbonate.
  • the electron injection layer may be composed of a laminate in which two or more layers are laminated, and examples thereof include a LiF layer / Ca layer laminate.
  • the electron injection layer is formed by vapor deposition, sputtering, printing, or the like.
  • the thickness of the electron injection layer is preferably about 1 nm to 1 ⁇ m.
  • a material for the cathode is preferably a material having a low work function, easy electron injection into the light emitting layer, and high electrical conductivity. Further, in the organic EL element that extracts light from the anode side, the light from the light emitting layer is reflected to the anode side by the cathode, and therefore, a material having a high visible light reflectance is preferable as the material of the cathode.
  • a material having a high visible light reflectance is preferable as the material of the cathode.
  • an alkali metal, an alkaline earth metal, a transition metal, a group III-B metal, or the like can be used.
  • cathode material examples include lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and the like.
  • An alloy or graphite or a graphite intercalation compound is used.
  • alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, calcium-aluminum alloys, and the like.
  • a transparent conductive electrode made of a conductive metal oxide or a conductive organic material can be used.
  • the conductive metal oxide include indium oxide, zinc oxide, tin oxide, ITO, and IZO
  • examples of the conductive organic substance include polyaniline or a derivative thereof, polythiophene or a derivative thereof, and the like.
  • the cathode may be composed of a laminate in which two or more layers are laminated.
  • the film thickness of the cathode is appropriately set in consideration of electric conductivity and durability, and is, for example, 10 nm to 10 ⁇ m, preferably 20 nm to 1 ⁇ m, and more preferably 50 nm to 500 nm.
  • Examples of the method for producing the cathode include a vacuum deposition method, a sputtering method, and a laminating method in which a metal thin film is thermocompression bonded.
  • examples of the material for the insulating layer provided adjacent to the electrode include metal fluorides, metal oxides, and organic insulating materials.
  • an organic EL element having an insulating layer having a thickness of 2 nm or less an element having an insulating layer having a thickness of 2 nm or less adjacent to the cathode and an element having an insulating layer having a thickness of 2 nm or less adjacent to the anode are used. Can be mentioned.
  • the organic EL element described above 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.
  • Examples of display devices including organic EL elements include active matrix display devices, passive matrix display devices, segment display devices, dot matrix display devices, and liquid crystal display devices.
  • the organic EL element is used as a light emitting element constituting each pixel in an active matrix display device and a passive matrix display device, and is used as a light emitting element constituting each segment in a segment display device. In a liquid crystal display device, it is used as a backlight.
  • Synthesis example 1 (Synthesis of polymer compound 1) Under an inert gas atmosphere, 9,9-bis (3,5-bis (n-hexyl) phenyl) -2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane- 2-yl) -fluorene (3.9339 g), N, N′-bis (4-bromophenyl) -N, N′-bis (2,6-dimethyl-4-n-butylphenyl) -1,4- Phenylenediamine (1.9223 g), 9,9-dioctyl-2,7-dibromofluorene (0.5947 g), 9,9-bis (benzocyclobuten-4-yl) -2,7-dibromofluorene (0.
  • phenylboric acid 0.053 g
  • palladium acetate 1.0 mg
  • tris (2-methoxyphenyl) phosphine 6.1 mg
  • 20 wt% tetraethylammonium hydroxide aqueous solution (15.3 g) were added and heated overnight. Refluxed.
  • the organic layer was washed twice with ion-exchanged water (56 mL), twice with a 3 wt% aqueous acetic acid solution (56 mL), and twice with ion-exchanged water (56 mL).
  • the organic layer was added dropwise to methanol and the resulting precipitate was collected by filtration and dried to give a solid.
  • This solid was dissolved in toluene, and a toluene solution was passed through a silica gel / alumina column through which toluene was passed in advance.
  • the eluate after passing through was dropped into methanol, and the resulting precipitate was collected by filtration and dried to obtain 3.71 g of polymer compound 1.
  • Polymer compound 1 has the following constitutional units and molar ratios from the monomer charge ratio, and is presumed to be a polymer compound in which constitutional units of (PA) and constitutional units selected from (PB) are alternately polymerized Is done.
  • Me represents a methyl group
  • n-Bu represents an n-butyl group
  • Synthesis example 2 (Preparation of red light emitting polymer material 1) 92.5% by weight of a polymer material of polyfluorene derivative,
  • the red light-emitting polymer material 1 was obtained by mixing 7.5% by weight of the metal complex 1 represented by the following formula.
  • the metal complex 1 was synthesized by the method described in paragraphs [0201] and [0202] of JP2010-43243A.
  • Synthesis example 3 (Synthesis of green light emitting polymer material 1) Under an inert gas atmosphere, 2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9,9-di (4-hexylphenyl) fluorene (18 152g), 2,7-dibromo-9,9-di (4-hexylphenyl) fluorene (9.601 g), 2,7-dibromo-9,9-di (octyl) fluorene (2.505 g), N , N′-bis (4-bromophenyl) -N, N′-bis (2,6-dimethyl-4-tert-butylphenyl) -1,4-phenylenediamine (1.687 g), N, N′- Bis (4-bromophenyl) -N, N′-bis (4-tert-butylphenyl) -9,10-anthracenediamine
  • Dichlorobistriphenylphosphine palladium (II) (16 mg) was added and heated to 100 ° C., a 20 wt% tetraethylammonium hydroxide aqueous solution (81 g) was added dropwise, and the mixture was heated to reflux for 5 hours. Next, phenylboric acid (0.28 g) and toluene (12 g) were added, and the mixture was heated to reflux overnight. Thereafter, toluene (1800 g), sodium N, N-diethyldithiocarbamate trihydrate (13 g) and ion-exchanged water (120 g) were added, and the mixture was stirred at 40 ° C. for 3 hours.
  • ion exchange water 120 g was added to the organic layer, and the mixture was stirred at 40 ° C. for 0.5 hour to separate the organic layer and the aqueous layer.
  • the organic layer was azeotropically dehydrated under reduced pressure (40 kPa) using a flask equipped with a Gene Stark tube. When water distillation could not be confirmed, the pressure was restored and cooled, and then the precipitated solid was removed by filtration.
  • the organic layer was washed twice with 10% hydrochloric acid (120 g), twice with 3% aqueous ammonia (120 g), and twice with ion-exchanged water (120 g).
  • the organic layer was passed through a silica gel / alumina column through which toluene was passed in advance.
  • the eluate after passing through was dropped into methanol, and the resulting precipitate was collected by filtration and dried to obtain 20 g of green light-emitting polymer material 1.
  • the green light-emitting polymer material 1 has the following constituent units and molar ratios from the monomer charge ratio, and is a polymer compound in which constituent units of (PA) and constituent units selected from (PB) are alternately polymerized It is estimated to be.
  • Example 1 An organic EL element having the following configuration was produced. “Glass substrate / ITO (150 nm) / hole injection layer (65 nm) / polymer compound 1 layer (20 nm) / red light emitting polymer material 1 layer (80 nm) / Ba layer (5 nm) / Al layer (80 nm)”
  • the suspension was applied by spin coating to form a thin film having a thickness of 65 nm, and the thin film was baked by heating at 200 ° C. for 10 minutes on a hot plate to obtain a hole injection layer.
  • the thin film forming step and the firing step were performed in an air atmosphere.
  • the polymer compound 1 which is a hole transport material was dissolved in xylene to prepare a xylene solution 1.
  • the concentration of the polymer compound 1 in the xylene solution 1 was 0.8% by weight.
  • the xylene solution 1 is applied onto the hole injection layer by spin coating to form a thin film for a hole transport layer having a film thickness of 20 nm, and the oxygen concentration and water concentration are in volume fractions.
  • the thin film was baked by heating at 180 ° C. for 1 hour in a nitrogen atmosphere controlled to 10 ppm or less to obtain a hole transport layer.
  • the red light-emitting polymer material 1 was dissolved in xylene to prepare a xylene solution 2.
  • the concentration of the red light-emitting polymer material 1 in the xylene solution 2 was 1.3% by weight.
  • the xylene solution 2 was applied onto the hole transport layer by spin coating in an air atmosphere to form a thin film for a light emitting layer having a thickness of 80 nm.
  • hydrogen is supplied from a hydrogen cylinder having a volume fraction of hydrogen of 100%, and heated at 130 ° C. for 60 minutes in a hydrogen atmosphere in which the oxygen concentration and the water concentration are controlled to 10 ppm or less by volume fraction.
  • the thin film was baked to obtain a light emitting layer.
  • the pressure in the thin film formation step and the firing step was atmospheric pressure.
  • the organic EL element was produced by sealing using a glass substrate.
  • the produced organic EL element emitted red light (CIE 1931 chromaticity coordinates: (0.62, 0.38)), and the maximum current efficiency was 21.8 cd / A.
  • the time until the luminance became 50% of the initial luminance was 160 hours.
  • the suspension was applied by spin coating to form a thin film having a thickness of 65 nm, and the thin film was baked by heating at 200 ° C. for 10 minutes on a hot plate to obtain a hole injection layer.
  • the thin film forming step and the firing step were performed in an air atmosphere.
  • the polymer compound 1 which is a hole transport material was dissolved in xylene to prepare a xylene solution 1.
  • the concentration of the polymer compound 1 in the xylene solution 1 was 0.8% by weight.
  • the xylene solution 1 is applied onto the hole injection layer by spin coating to form a thin film for a hole transport layer having a film thickness of 20 nm, and the oxygen concentration and water concentration are in volume fractions.
  • the thin film was baked by heating at 180 ° C. for 1 hour in a nitrogen atmosphere controlled to 10 ppm or less to obtain a hole transport layer.
  • the red light-emitting polymer material 1 was dissolved in xylene to prepare a xylene solution 2.
  • the concentration of the red light-emitting polymer material 1 in the xylene solution 2 was 1.3% by weight.
  • the xylene solution 2 was applied onto the hole transport layer by a spin coating method to form a thin film for a light emitting layer having a thickness of 80 nm.
  • the thin film was baked by heating at 130 ° C. for 60 minutes in a nitrogen atmosphere in which the oxygen concentration and the water concentration were controlled to be 10 ppm or less by volume fraction, whereby a light emitting layer was obtained.
  • the pressure in the thin film formation step and the firing step was atmospheric pressure.
  • the organic EL element was produced by sealing using a glass substrate.
  • the produced organic EL element emitted red light (CIE 1931 chromaticity coordinates: (0.62, 0.38)), and the maximum current efficiency was 21.3 cd / A.
  • the time until the luminance became 50% of the initial luminance was 135 hours.
  • Example 2 An organic EL element having the following configuration was produced. “Glass substrate / ITO layer (150 nm) / hole injection layer (65 nm) / polymer compound 1 layer (20 nm) / green light emitting polymer material 1 layer (80 nm) / Ba layer (5 nm) / Al layer (80 nm)”
  • the suspension was applied by spin coating to form a thin film having a thickness of 65 nm, and the thin film was baked by heating at 200 ° C. for 10 minutes on a hot plate to obtain a hole injection layer.
  • the thin film forming step and the firing step were performed in an air atmosphere.
  • the polymer compound 1 which is a hole transport material was dissolved in xylene to prepare a xylene solution 1.
  • the concentration of the polymer compound 1 in the xylene solution 1 was 0.8% by weight.
  • the xylene solution 1 is applied onto the hole injection layer by spin coating to form a thin film for a hole transport layer having a film thickness of 20 nm, and the oxygen concentration and water concentration are in volume fractions.
  • the thin film was baked by heating at 180 ° C. for 1 hour in a nitrogen atmosphere controlled to 10 ppm or less to obtain a hole transport layer.
  • the green light-emitting polymer material 1 was dissolved in xylene to prepare a xylene solution 3.
  • the concentration of the green light-emitting polymer material 1 in the xylene solution 3 was 1.4% by weight.
  • the xylene solution 3 was applied onto the hole transport layer by spin coating in an air atmosphere to form a thin film for a light emitting layer having a thickness of 80 nm.
  • hydrogen is supplied from a hydrogen cylinder having a volume fraction of hydrogen of 100%, and heated at 130 ° C. for 60 minutes in a hydrogen atmosphere in which the oxygen concentration and the water concentration are controlled to 10 ppm or less by volume fraction.
  • the thin film was baked to obtain a light emitting layer.
  • the pressure in the thin film formation step and the firing step was atmospheric pressure.
  • the organic EL element was produced by sealing using a glass substrate.
  • the produced organic EL element emitted green light (CIE 1931 chromaticity coordinates: (0.32, 0.61)), and the maximum current efficiency was 11.9 cd / A.
  • the time until the luminance became 50% of the initial luminance was 236 hours.
  • the suspension was applied by spin coating to form a thin film having a thickness of 65 nm, and the thin film was baked by heating at 200 ° C. for 10 minutes on a hot plate to obtain a hole injection layer.
  • the thin film forming step and the firing step were performed in an air atmosphere.
  • the polymer compound 1 which is a hole transport material was dissolved in xylene to prepare a xylene solution 1.
  • the concentration of the polymer compound 1 in the xylene solution 1 was 0.8% by weight.
  • the xylene solution 1 is applied onto the hole injection layer by spin coating to form a thin film for a hole transport layer having a film thickness of 20 nm, and the oxygen concentration and water concentration are in volume fractions.
  • the thin film was baked by heating at 180 ° C. for 1 hour in a nitrogen atmosphere controlled to 10 ppm or less to obtain a hole transport layer.
  • the green light-emitting polymer material 1 was dissolved in xylene to prepare a xylene solution 3.
  • the concentration of the green light-emitting polymer material 1 in the xylene solution 3 was 1.4% by weight.
  • the xylene solution 3 was applied onto the hole transport layer by a spin coating method to form a thin film for a light emitting layer having a thickness of 80 nm.
  • the thin film was baked by heating at 130 ° C. for 60 minutes in a nitrogen atmosphere in which the oxygen concentration and the water concentration were controlled to be 10 ppm or less by volume fraction, whereby a light emitting layer was obtained.
  • the pressure in the thin film formation step and the firing step was atmospheric pressure.
  • the organic EL element was produced by sealing using a glass substrate.
  • the produced organic EL element emitted green light (CIE 1931 chromaticity coordinates: (0.32, 0.61)), and the maximum current efficiency was 11.3 cd / A.
  • the time until the luminance became 50% of the initial luminance was 222 hours.
  • Example 3 and Comparative Example 3 An organic EL element is produced in the same manner as in Example 1 except that the red light-emitting polymer material “RP221” manufactured by Summation Co., Ltd. is used instead of the red light-emitting polymer material 1 (Example 3). Further, an organic EL element is produced in the same manner as in Example 3 except that a light emitting layer is obtained by baking a thin film using a nitrogen atmosphere instead of a hydrogen atmosphere (Comparative Example 3). Both produced organic EL elements emit red light. And when the characteristics of those organic EL elements were measured in the same manner as in Example 1, at least the maximum current efficiency or luminance half-life was compared with the organic EL element of Example 3 compared to the organic EL element of Comparative Example 3. A significant improvement is observed.
  • Example 4 and Comparative Example 4 An organic EL element is produced in the same manner as in Example 2 except that Green Light-Emitting Polymer Material “Green 1300” manufactured by Summation Company is used instead of Green Light-Emitting Polymer Material 1 (Example 4). Further, an organic EL element is produced in the same manner as in Example 4 except that a light emitting layer is obtained by baking a thin film using a nitrogen atmosphere instead of a hydrogen atmosphere (Comparative Example 4). Both produced organic EL elements emit green light. And when the characteristics of those organic EL elements were measured in the same manner as in Example 2, at least the maximum current efficiency or luminance half-life was compared with the organic EL element of Example 4 compared to the organic EL element of Comparative Example 4. A significant improvement is observed.

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Abstract

La présente invention vise à améliorer la durée de vie de demi-atténuation de luminance d'un élément électroluminescent organique. A cet effet, l'invention porte sur un procédé pour produire un élément électroluminescent organique comprenant une première électrode, une seconde électrode et une couche organique disposée entre la première électrode et la seconde électrode, lequel procédé est caractérisé en ce que la couche organique est formée par la formation d'un film mince contenant un composé organique et par la calcination du film mince dans une atmosphère contenant un gaz réducteur.
PCT/JP2011/069984 2010-09-03 2011-09-02 Élément électroluminescent organique et son procédé de production WO2012029936A1 (fr)

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