WO2016084648A1 - Élément électroluminescent organique, et dispositif d'éclairage et dispositif d'affichage le comprenant chacun - Google Patents

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

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WO2016084648A1
WO2016084648A1 PCT/JP2015/082187 JP2015082187W WO2016084648A1 WO 2016084648 A1 WO2016084648 A1 WO 2016084648A1 JP 2015082187 W JP2015082187 W JP 2015082187W WO 2016084648 A1 WO2016084648 A1 WO 2016084648A1
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organic
layer
metal
light emitting
light
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邦夫 谷
井上　暁
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コニカミノルタ株式会社
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
    • Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps

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  • the present invention relates to an organic electroluminescence element, and an illumination device and a display device provided with the organic electroluminescence device. More specifically, the present invention relates to a long-life organic electroluminescence element, and an illumination device and a display device including the organic electroluminescence element.
  • An organic electroluminescence element (hereinafter also referred to as an organic EL element) has a configuration in which a light emitting layer containing a light emitting compound is sandwiched between a cathode and an anode, and is injected from the anode by applying an electric field.
  • a light emitting device that utilizes excitons (excitons) by recombining electrons injected from holes and cathodes in the light emitting layer, and light emission (fluorescence / phosphorescence) when the excitons are deactivated It is.
  • An organic EL element is an all-solid-state element composed of an organic material film with a thickness of only a submicron between electrodes, and can emit light at a voltage of several volts to several tens of volts. It is expected to be used for next-generation flat display and lighting.
  • Non-Patent Document 1 As for development of an organic EL element for practical use, Princeton University has reported an organic EL element using phosphorescence emission from an excited triplet utilizing an internal heavy atom effect (see, for example, Non-Patent Document 1). Since then, research on materials that exhibit phosphorescence at room temperature has become active (see, for example, Patent Document 1 and Non-Patent Document 2).
  • organic EL elements that utilize phosphorescence emission can in principle achieve a light emission efficiency that is approximately four times that of organic EL elements that utilize previous fluorescence emission.
  • Research and development of device layer configurations and electrodes are performed all over the world. For example, many compounds have been studied focusing on heavy metal complexes such as iridium complexes (see, for example, Non-Patent Document 3).
  • the phosphorescence emission method is a method having a very high potential.
  • an organic EL device using phosphorescence emission is more likely to cause T-Tanihilation than an organic EL device using fluorescence emission.
  • efficiency and life are reduced by brightness.
  • One of the reasons is that the excited triplet state unique to the phosphorescent material is long (the phosphorescence lifetime is long). This is because in the light emission process, there is a high possibility that light emission is quenched by the peripheral material due to the long excited state. That is, in order to improve the device life, it is important to shorten the phosphorescence life, and improvement is desired, but such a report has hardly been made.
  • the present invention has been made in view of the above problems and situations, and a problem to be solved is to achieve a shortened phosphorescence lifetime and provide a long-life organic electroluminescence element. Moreover, it is providing the illuminating device and display apparatus with which the said organic electroluminescent element was comprised.
  • the present inventor contains at least two kinds of metal compounds as dopants in the light-emitting layer, and at least one of them contains a phosphorescent metal complex (D1). And at least one is a non-luminescent metal compound (D2), and the atomic number of the metal constituting the non-luminescent metal compound (D2) is the atom of the central metal of the phosphorescent metal complex.
  • An organic electroluminescence device having a light emitting layer between an anode and a cathode and containing at least two kinds of metal compounds as dopants in the light emitting layer, wherein at least one of the metal compounds is a phosphorescent metal complex (D1), at least one of which is a nonluminous metal compound (D2), and the atomic number of the metal constituting the nonluminous metal compound is greater than the atomic number of the central metal of the phosphorescent metal complex.
  • D1 phosphorescent metal complex
  • D2 nonluminous metal compound
  • An organic electroluminescence element characterized by being large.
  • organic electroluminescence element according to any one of items 1 to 3, wherein the organic electroluminescence element is an organic electroluminescence element that emits white light.
  • a display device comprising the organic electroluminescence element according to any one of items 1 to 4.
  • the above-described means of the present invention can achieve a shortened phosphorescence lifetime and provide a long-life organic electroluminescence element.
  • a lighting device and a display device each including the organic electroluminescence element can be provided.
  • the effect of the present invention is considered to be based on the external heavy atom effect by the non-luminescent metal compound (D2).
  • the heavy atom effect is the introduction of heavy atoms outside the molecule, such as in the molecule or in the solvent, to increase the spin-orbit interaction, and forbidden transitions such as intersystem crossing (S * ⁇ T * ) and phosphorescence.
  • S * ⁇ T * intersystem crossing
  • T * ⁇ S 0 A phenomenon in which light emission (T * ⁇ S 0 ) is promoted.
  • a heavy atom means an atomic number, that is, an atom having a large number of positive charges in the nucleus.
  • the external heavy atom effect is expressed by using a non-luminous metal compound (D2) having a heavy atom around the phosphorescent metal complex (D1) having the internal heavy atom effect (outside the molecule). It is thought that. This is presumed to be because phosphorescence emission was promoted (radiation rate constant: Kr increased) by further increasing the spin-orbit interaction.
  • An example of a display device composed of organic EL elements Schematic diagram of display part A Pixel circuit diagram Schematic diagram of a passive matrix display device Schematic of lighting device Cross section of the lighting device
  • the organic electroluminescence device of the present invention is an organic electroluminescence device having a light emitting layer between an anode and a cathode, and containing at least two kinds of metal compounds as dopants in the light emitting layer, and at least of the metal compounds
  • One is a phosphorescent metal complex (D1)
  • at least one is a nonluminous metal compound (D2)
  • the atomic number of the metal constituting the nonluminous metal compound is the phosphorescent property. It is characterized by being larger than the atomic number of the central metal of the metal complex.
  • the central metal of the phosphorescent metal complex (D1) is iridium (Ir) from the viewpoint of manifesting the effects of the present invention.
  • the atomic number of the metal which comprises a nonluminous metal compound (D2) is more than the atomic number of Au, since a bigger heavy atom effect is acquired.
  • an organic electroluminescence element that emits white light is preferable.
  • the organic EL element of the present invention can be suitably included in a lighting device and a display device.
  • ⁇ is used to mean that the numerical values described before and after it are included as a lower limit value and an upper limit value.
  • the organic electroluminescence device of the present invention contains at least two kinds of metal compounds in the light emitting layer, and at least one of the metal compounds is a phosphorescent metal complex (D1), and at least one kind is non-light emitting. It is a metal compound (D2) and the atomic number of the metal which comprises the said nonluminous metal compound (D2) is larger than the atomic number of the central metal of the said phosphorescence-emitting metal complex.
  • the light emission or non-light emission of the two kinds of metal compounds according to the present invention is a relationship when an organic EL device is used, and the non-light emission substantially includes light emission caused by the non-light emission metal compound. It means not.
  • the color of light emitted from the phosphorescent metal complex (D1) does not substantially change even when the non-luminescent metal compound (D2) is added.
  • the fact that it does not change substantially means that even if a non-luminescent metal compound is added to the light-emitting layer containing the phosphorescent metal complex (D1), the CIE (International Commission on Illumination Commission Internationale de L'Eclairage) 1931 color system
  • the change of the (x, y) color coordinate of the luminescent color from the luminescent dopant based on the chromaticity diagram in is said to be less than 0.015 unit. In some embodiments, the change in CIE (x, y) color coordinates is less than 0.010 units.
  • the phosphorescent metal complex according to the present invention is a compound in which light emission from an excited triplet is observed, specifically, a compound that emits phosphorescence at room temperature (25 ° C.), and a phosphorescence quantum yield. Is defined as a compound of 0.01 or more at 25 ° C., but a preferable phosphorescence quantum yield is 0.1 or more.
  • the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescent metal complex according to the present invention has the above phosphorescence quantum yield (0.01 or more) in any solvent. It only has to be achieved.
  • phosphorescent metal complexes There are two types of light emission of phosphorescent metal complexes in principle. One is the recombination of carriers on the host compound to which carriers are transported to generate an excited state of the host compound, and this energy is phosphorescent. It is an energy transfer type in which light emission from a phosphorescent metal complex is obtained by transferring to a light emitting metal complex. The other is a carrier trap type in which a phosphorescent metal complex serves as a carrier trap, and recombination of carriers occurs on the phosphorescent metal complex to emit light from the phosphorescent metal complex. In any case, it is a condition that the excited state energy of the phosphorescent metal complex is lower than the excited state energy of the host compound.
  • the phosphorescent metal complex that can be used in the present invention can be appropriately selected from known ones used for the light emitting layer of the organic EL device.
  • JP 2010-47764 A JP 2010-47764 A.
  • a preferable phosphorescent metal complex includes an organometallic complex having Ir as a central metal. More preferably, a complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond is preferable.
  • the nonluminous metal compound (D2) is a compound containing at least one metal element selected from Group 3 to Group 11 transition metal elements or Group 13 to Group 15 base metal elements of the periodic table. It is preferable that
  • the central metal of the phosphorescent metal complex is preferably Ir from the viewpoint of luminous efficiency.
  • the non-light emitting metal compound used with Ir is a metal compound containing a metal having an atomic number larger than Ir.
  • Pt, Au, and Bi are preferable, and among them, the atomic number of Au or more is preferable.
  • Au and Bi are particularly preferable.
  • the nonluminous metal compound preferably has at least one carbon atom, oxygen atom, and nitrogen atom, and has at least one coordination mode of a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond.
  • a complex containing or a compound having a metal-carbon bond is preferred.
  • the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode or the electron transport layer and the hole transport layer, and the light emitting portion is in the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.
  • the total thickness of the light emitting layer is not particularly limited, but from the viewpoint of improving the stability of the emission color against the drive current and the uniformity of the film, preventing unnecessary application of high voltage during light emission. It is preferably adjusted within the range of 2 nm to 5 ⁇ m, more preferably adjusted within the range of 2 to 200 nm, and particularly preferably within the range of 5 to 100 nm.
  • the light emitting layer according to the present invention contains at least two kinds of dopants described above.
  • the ratio of the non-light emitting metal compound to the phosphorescent metal complex in the light emitting layer is within the range of 0.5 to 50 times (mass ratio) with respect to the phosphorescent metal complex. It is preferable from the viewpoint of expression. Further, the total of the two kinds of metal compounds of the phosphorescent metal complex and the nonluminous metal compound is preferably 1 to 90% by mass with respect to the total amount of the light emitting layer.
  • the light emitting layer preferably contains a host compound.
  • the host compound according to the present invention is a compound mainly responsible for charge injection and transport in the light-emitting layer, and light emission itself is not substantially observed in the organic EL element.
  • it is a compound having a phosphorescence quantum yield of phosphorescence emission of less than 0.1 at room temperature (25 ° C.), more preferably a compound having a phosphorescence quantum yield of less than 0.01. Moreover, it is preferable that the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.
  • the excited state energy of the host compound is preferably higher than the excited state energy of the phosphorescent metal complex contained in the same layer.
  • the host compounds may be used alone or in combination of two or more. By using a plurality of types of host compounds, it is possible to adjust the movement of charges, and the organic EL element can be made highly efficient.
  • the host compound that can be used in the present invention is not particularly limited, and compounds conventionally used in organic EL devices can be used. It may be a low molecular compound or a high molecular compound having a repeating unit, or a compound having a reactive group such as a vinyl group or an epoxy group.
  • Tg glass transition temperature
  • the glass transition point (Tg) is a value determined by a method based on JIS-K-7121 using DSC (Differential Scanning Colorimetry).
  • the electron transport layer is made of a material having a function of transporting electrons, and may have a function of transmitting electrons injected from the cathode to the light emitting layer.
  • the total thickness of the electron transport layer is not particularly limited, but is usually in the range of 2 nm to 5 ⁇ m, more preferably 2 to 500 nm, and further preferably 5 to 200 nm.
  • the organic EL element when the light generated in the light emitting layer is extracted from the electrode, the light extracted directly from the light emitting layer interferes with the light extracted after being reflected by the electrode from which the light is extracted and the electrode located at the counter electrode. It is known to wake up. When light is reflected by the cathode, this interference effect can be efficiently utilized by appropriately adjusting the total thickness of the electron transport layer between 5 nm and 200 ⁇ m.
  • the electron mobility of the electron transport layer is preferably 10 ⁇ 5 cm 2 / Vs or more.
  • the material used for the electron transport layer may be any of electron injecting or transporting properties and hole blocking properties, and can be selected from conventionally known compounds. Can be selected and used.
  • a nitrogen-containing aromatic heterocyclic derivative (carbazole derivative, azacarbazole derivative (one or more of carbon atoms constituting the carbazole ring is substituted with a nitrogen atom), pyridine derivative, pyrimidine derivative, pyrazine derivative, pyridazine derivative, Triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, azatriphenylene derivatives, oxazole derivatives, thiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, etc.), dibenzofuran derivatives, And dibenzothiophene derivatives, silole derivatives, aromatic hydrocarbon ring derivatives (naphthalene derivatives, anthracene derivatives, triphenylene, etc.)
  • a metal complex having a quinolinol skeleton or a dibenzoquinolinol skeleton as a ligand such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7- Dibromo-8-quinolinol) aluminum, tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc.
  • a metal complex in which the central metal is replaced with In, Mg, Cu, Ca, Sn, Ga, or Pb can also be used as the electron transport material.
  • metal-free or metal phthalocyanine or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material.
  • the distyrylpyrazine derivative exemplified as the material for the light emitting layer can also be used as an electron transport material, and an inorganic semiconductor such as n-type-Si, n-type-SiC, etc. as in the case of the hole injection layer and the hole transport layer. Can also be used as an electron transporting material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials as a polymer main chain can be used.
  • the electron transport layer may be doped with a doping material as a guest material to form an electron transport layer having a high n property (electron rich).
  • the doping material include n-type dopants such as metal complexes and metal compounds such as metal halides.
  • Specific examples of the electron transport layer having such a structure include, for example, JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J. Pat. Appl. Phys. , 95, 5773 (2004) and the like.
  • More preferable electron transport materials in the present invention include pyridine derivatives, pyrimidine derivatives, pyrazine derivatives, triazine derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, carbazole derivatives, azacarbazole derivatives, and benzimidazole derivatives.
  • the electron transport material may be used alone or in combination of two or more.
  • the hole blocking layer is a layer having a function of an electron transport layer in a broad sense, and is preferably made of a material having a function of transporting electrons while having a small ability to transport holes, and transporting electrons while transporting holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the structure of the electron transport layer described above can be used as a hole blocking layer according to the present invention, if necessary.
  • the hole blocking layer provided in the organic EL element is preferably provided adjacent to the cathode side of the light emitting layer.
  • the layer thickness of the hole blocking layer according to the present invention is preferably in the range of 3 to 100 nm, more preferably in the range of 5 to 30 nm.
  • the material used for the hole blocking layer As the material used for the hole blocking layer, the material used for the above-described electron transport layer is preferably used, and the material used as the above-described host compound is also preferably used for the hole blocking layer.
  • the electron injection layer (also referred to as “cathode buffer layer”) according to the present invention is a layer provided between the cathode and the light emitting layer in order to lower the driving voltage and improve the light emission luminance. It is described in detail in Chapter 2 “Electrode Materials” (pages 123 to 166) of the second edition of “The Forefront of Industrialization (issued by NTT Corporation on November 30, 1998)”.
  • the electron injection layer may be provided as necessary, and may be present between the cathode and the light emitting layer or between the cathode and the electron transport layer as described above.
  • the electron injection layer is preferably a very thin film, and the layer thickness is preferably in the range of 0.1 nm to 5 nm, depending on the material. Moreover, the nonuniform film
  • JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like Specific examples of materials preferably used for the electron injection layer are as follows. , Metals typified by strontium and aluminum, alkali metal compounds typified by lithium fluoride, sodium fluoride, potassium fluoride, etc., alkaline earth metal compounds typified by magnesium fluoride, calcium fluoride, etc., oxidation Examples thereof include metal oxides typified by aluminum, metal complexes typified by lithium 8-hydroxyquinolate (Liq), and the like. Further, the above-described electron transport material can also be used.
  • the materials used for the electron injection layer may be used alone or in combination of two or more.
  • the hole transport layer is made of a material having a function of transporting holes and may have a function of transmitting holes injected from the anode to the light emitting layer.
  • the total thickness of the hole transport layer is not particularly limited, but is usually in the range of 2 nm to 5 ⁇ m, more preferably in the range of 2 to 500 nm, and still more preferably in the range of 5 to 200 nm.
  • a material used for the hole transport layer (hereinafter referred to as a hole transport material), any material that has either a hole injection property or a transport property or an electron barrier property may be used. Any one can be selected and used.
  • porphyrin derivatives for example, porphyrin derivatives, phthalocyanine derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, imidazole derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, hydrazone derivatives, stilbene derivatives, polyarylalkane derivatives, triarylamine derivatives, carbazole derivatives , Indolocarbazole derivatives, isoindole derivatives, acene derivatives such as anthracene and naphthalene, fluorene derivatives, fluorenone derivatives, and polyvinyl carbazole, polymer materials or oligomers with aromatic amines introduced into the main chain or side chain, polysilane, conductive And polymer (for example, PEDOT: PSS, aniline copolymer, polyaniline, polythiophene, etc.).
  • PEDOT PSS, aniline copolymer, polyaniline
  • triarylamine derivative examples include a benzidine type typified by ⁇ NPD, a starburst type typified by MTDATA, and a compound having fluorene or anthracene in the triarylamine linking core part.
  • hexaazatriphenylene derivatives such as those described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as a hole transport material.
  • a hole transport layer having a high p property doped with impurities can also be used.
  • examples thereof include JP-A-4-297076, JP-A-2000-196140, JP-A-2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
  • JP-A-11-251067, J. Org. Huang et. al. It is also possible to use so-called p-type hole transport materials and inorganic compounds such as p-type-Si and p-type-SiC, as described in the literature (Applied Physics Letters 80 (2002), p. 139). Further, ortho-metalated organometallic complexes having Ir or Pt as the central metal as typified by Ir (ppy) 3 are also preferably used.
  • the above-mentioned materials can be used as the hole transport material, a triarylamine derivative, a carbazole derivative, an indolocarbazole derivative, an azatriphenylene derivative, an organometallic complex, or an aromatic amine is introduced into the main chain or side chain.
  • the polymer materials or oligomers used are preferably used.
  • preferable hole transport materials used for organic EL elements include the compounds described in the following documents in addition to the documents listed above, but the present invention is not limited thereto.
  • the hole transport material may be used alone or in combination of two or more.
  • the electron blocking layer is a layer having a function of a hole transport layer in a broad sense, and is preferably made of a material having a function of transporting holes and a small ability to transport electrons, and transporting electrons while transporting holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the above-described configuration of the hole transport layer can be used as an electron blocking layer according to the present invention, if necessary.
  • the electron blocking layer provided in the organic EL element is preferably provided adjacent to the anode side of the light emitting layer.
  • the layer thickness of the electron blocking layer according to the present invention is preferably in the range of 3 to 100 nm, more preferably in the range of 5 to 30 nm.
  • the material used for the electron blocking layer is preferably used, and the material used for the host compound is also preferably used for the electron blocking layer.
  • the hole injection layer (also referred to as “anode buffer layer”) according to the present invention is a layer provided between the anode and the light emitting layer for the purpose of lowering the driving voltage and improving the light emission luminance. It is described in detail in Volume 2, Chapter 2, “Electrode Materials” (pages 123 to 166) of “The Forefront of Industrialization (issued by NTT Corporation on November 30, 1998)”.
  • the hole injection layer may be provided as necessary, and may be present between the anode and the light emitting layer or between the anode and the hole transport layer as described above.
  • the details of the hole injection layer are described in JP-A-9-45479, JP-A-9-260062, JP-A-8-288069, etc.
  • Examples of materials used for the hole injection layer include: Examples thereof include materials used for the above-described hole transport layer.
  • phthalocyanine derivatives typified by copper phthalocyanine, hexaazatriphenylene derivatives, metal oxides typified by vanadium oxide, amorphous carbon as described in JP-T-2003-519432, JP-A-2006-135145, etc.
  • the materials used for the hole injection layer described above may be used alone or in combination of two or more.
  • the organic layer in the present invention described above may further contain other inclusions.
  • halogen elements and halogenated compounds such as bromine, iodine and chlorine, alkali metals and alkaline earth metals such as Pd, Ca and Na, transition metal compounds, complexes and salts.
  • the content of other contents can be arbitrarily determined, but is preferably 1000 ppm or less, more preferably 500 ppm or less, and still more preferably 50 ppm or less with respect to the total mass% of the contained layer. It is.
  • the light emitting layer according to the present invention is composed of a single layer or a plurality of layers, and when there are a plurality of light emitting layers, a non-light emitting intermediate layer may be provided between the light emitting layers.
  • a hole blocking layer also referred to as a hole blocking layer
  • an electron injection layer also referred to as a cathode buffer layer
  • An electron blocking layer also referred to as an electron barrier layer
  • a hole injection layer also referred to as an anode buffer layer
  • the electron transport layer according to the present invention is a layer having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer. Moreover, you may be comprised by multiple layers.
  • the hole transport layer according to the present invention is a layer having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer. Moreover, you may be comprised by multiple layers.
  • the layer excluding the anode and the cathode is also referred to as “organic layer”.
  • the organic EL element according to the present invention may be an element having a so-called tandem structure in which a plurality of light emitting units including at least one light emitting layer are stacked.
  • first light emitting unit / second light emitting unit / third light emitting unit / cathode Anode / first light emitting unit / intermediate layer / second light emitting unit / intermediate layer / third light emitting unit / cathode
  • first light emitting unit The second light emitting unit and the third light emitting unit may all be the same or different. Two light emitting units may be the same, and the remaining one may be different.
  • the third light emitting unit may not be provided, and on the other hand, a light emitting unit or an intermediate layer may be further provided between the third light emitting unit and the electrode.
  • a plurality of light emitting units may be laminated directly or via an intermediate layer, and the intermediate layer is generally an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, an intermediate layer.
  • Known materials and structures can be used as long as they are also called insulating layers and have a function of supplying electrons to the anode-side adjacent layer and holes to the cathode-side adjacent layer.
  • Examples of materials used for the intermediate layer include ITO (indium tin oxide), IZO (indium zinc oxide), ZnO 2 , TiN, ZrN, HfN, TiO x , VO x , CuI, InN, GaN, Conductive inorganic compound layers such as CuAlO 2 , CuGaO 2 , SrCu 2 O 2 , LaB 6 , RuO 2 and Al, two- layer films such as Au / Bi 2 O 3 , SnO 2 / Ag / SnO 2 , ZnO / Ag / ZnO, Bi 2 O 3 / Au / Bi 2 O 3 , TiO 2 / TiN / TiO 2 , TiO 2 / ZrN / TiO 2 and other multilayer films, C 60 and other fullerenes, conductive organic layers such as oligothiophene Conductive metal compound layers such as metal phthalocyanines, metal-free phthalocyanines, metal porphyrins, metal-free
  • Preferred examples of the structure within the light emitting unit include those obtained by removing the anode and the cathode from the structures (1) to (7) mentioned in the above representative element structures, but the present invention is not limited to these. Not.
  • tandem organic EL element for example, US Pat. No. 6,337,492, US Pat. No. 7,420,203, US Pat. No. 7,473,923, US Pat. No. 6,872,472, US Pat. No. 6,107,734, US Pat. No. 6,337,492, International Publication No. 2005/009087, Japanese Patent Application Laid-Open No. 2006-228712 JP, JP-A-2006-24791, JP-A-2006-49393, JP-A-2006-49394, JP-A-2006-49396, JP-A-2011-96679, JP-A-2005-340187, Japanese Patent No. 4711424, Japanese Patent No. 3496681, Japanese Patent No.
  • An organic layer (a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, or the like) will be described.
  • the method for forming the organic layer is not particularly limited, and a conventionally known method such as a vacuum deposition method or a wet method (also referred to as a wet process) can be used.
  • Examples of the wet method include spin coating method, casting method, ink jet method, printing method, die coating method, blade coating method, roll coating method, spray coating method, curtain coating method, and LB method (Langmuir-Blodgett method). From the viewpoint of obtaining a homogeneous thin film easily and high productivity, a method with high roll-to-roll method suitability such as a die coating method, a roll coating method, an ink jet method, and a spray coating method is preferable.
  • liquid medium for dissolving or dispersing the material constituting the organic EL device examples include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, toluene, and the like.
  • Aromatic hydrocarbons such as xylene, mesitylene and cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin and dodecane, and organic solvents such as DMF and DMSO can be used.
  • a dispersion method it can be dispersed by a dispersion method such as ultrasonic wave, high shearing force dispersion or media dispersion.
  • vapor deposition conditions vary depending on the type of compound used, but generally a boat heating temperature of 50 to 450 ° C., a degree of vacuum of 10 ⁇ 6 to 10 ⁇ 2 Pa, and a vapor deposition rate of 0.01 to It is desirable to select appropriately within a range of 50 nm / second, a substrate temperature of ⁇ 50 to 300 ° C., and a layer thickness of 0.1 nm to 5 ⁇ m, preferably 5 to 200 nm.
  • the formation of the organic layer is preferably made consistently from the hole injection layer to the cathode by a single evacuation, but it may be taken out halfway and subjected to different film forming methods. In that case, it is preferable to perform the work in a dry inert gas atmosphere.
  • anode As the anode in the organic EL element, those having a work function (4 eV or more, preferably 4.5 V or more) of a metal, an alloy, an electrically conductive compound and a mixture thereof as an electrode material are preferably used.
  • an electrode substance include metals such as Au, and conductive transparent materials such as CuI, ITO, SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
  • these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern of a desired shape may be formed by a photolithography method, or when pattern accuracy is not so required (about 100 ⁇ m or more)
  • a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
  • a wet film forming method such as a printing method or a coating method can be used.
  • the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 to 200 nm.
  • cathode As the cathode, a material having a work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound and a mixture thereof as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, aluminum, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
  • the emission luminance is improved, which is convenient.
  • a transparent or semi-transparent cathode can be produced by producing a conductive transparent material mentioned in the description of the anode on the cathode after producing the above metal with a thickness of 1 to 20 nm.
  • the support substrate (hereinafter also referred to as a substrate) that can be used in the organic EL element of the present invention is not particularly limited in the type of glass, plastic, etc., and may be transparent or opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.
  • polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate (TAC), cellulose acetate butyrate, cellulose acetate propionate ( CAP), cellulose esters such as cellulose acetate phthalate, cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfones Cycloolefin resins such as polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylate, Arton (trade name, manufactured by JSR) or Appel (trade name, manufactured by J
  • the surface of the resin film may be formed with an inorganic film, an organic film, or a hybrid film of both, and the water vapor permeability (25 ⁇ 0.5 ° C.) measured by a method according to JIS K 7129-1992.
  • Relative humidity (90 ⁇ 2)% RH) is preferably 1 ⁇ 10 ⁇ 2 g / (m 2 ⁇ 24 h) or less, and further measured by a method according to JIS K 7126-1987.
  • the material for forming the barrier film may be any material that has a function of suppressing entry of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
  • the method for forming the barrier film is not particularly limited.
  • vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam, ion plating, plasma polymerization, atmospheric pressure plasma polymerization A plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.
  • the opaque support substrate examples include metal plates such as aluminum and stainless steel, films, opaque resin substrates, ceramic substrates, and the like.
  • the external extraction quantum efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, and more preferably 5% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element ⁇ 100.
  • a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination.
  • sealing means used for sealing the organic EL element include a method of bonding a sealing member, an electrode, and a support substrate with an adhesive.
  • a sealing member it should just be arrange
  • transparency and electrical insulation are not particularly limited.
  • Specific examples include a glass plate, a polymer plate / film, and a metal plate / film.
  • the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
  • the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
  • a polymer film and a metal film can be preferably used because the organic EL element can be thinned.
  • the polymer film oxygen permeability measured by the method based on JIS K 7126-1987 is 1 ⁇ 10 -3 ml / m 2 / 24h or less, as measured by the method based on JIS K 7129-1992
  • water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)%) is preferably that of 1 ⁇ 10 -3 g / (m 2 / 24h) or less.
  • sealing member For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.
  • the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to.
  • hot-melt type polyamide, polyester, and polyolefin can be mentioned.
  • a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
  • an organic EL element may deteriorate by heat processing, what can be adhesively cured from room temperature to 80 ° C. is preferable.
  • a desiccant may be dispersed in the adhesive.
  • coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.
  • the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film.
  • a material for forming the film any material may be used as long as it has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
  • a laminated structure of these inorganic layers and layers made of organic materials it is preferable to have a laminated structure of these inorganic layers and layers made of organic materials.
  • the method of forming these films There are no particular limitations on the method of forming these films. For example, vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam, ion plating, plasma polymerization, atmospheric pressure plasma A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase.
  • a vacuum can also be used.
  • a hygroscopic compound can also be enclosed inside.
  • hygroscopic compound examples include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
  • metal oxides for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
  • sulfates for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate.
  • metal halides eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.
  • perchloric acids eg perchloric acid Barium, magnesium perchlorate, and the like
  • anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.
  • a protective film or a protective plate may be provided outside the sealing film or the sealing film on the side facing the support substrate with the organic layer interposed therebetween.
  • the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, etc. used for the sealing can be used, but the polymer film is light and thin. Is preferably used.
  • An organic electroluminescent element emits light inside a layer having a refractive index higher than that of air (with a refractive index of about 1.6 to 2.1), and about 15% to 20% of light generated in the light emitting layer. It is generally said that only light can be extracted. This is because light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because light is totally reflected between the light and the light is guided through the transparent electrode or the light emitting layer, and as a result, the light escapes in the direction of the side surface of the device.
  • a technique for improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate to prevent total reflection at the transparent substrate and the air interface (for example, US Pat. No. 4,774,435), A method for improving efficiency by providing light condensing property (for example, Japanese Patent Laid-Open No. 63-134795), a method for forming a reflective surface on the side surface of an element (for example, Japanese Patent Laid-Open No. 1-220394), a substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the substrate and the light emitter (for example, Japanese Patent Laid-Open No.
  • these methods can be used in combination with the organic electroluminescence device of the present invention, but a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, A method of forming a diffraction grating between any layers of the transparent electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
  • the light extracted from the transparent electrode has a higher extraction efficiency to the outside as the refractive index of the medium is lower.
  • the low refractive index layer examples include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally in the range of about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Furthermore, it is preferable that it is 1.35 or less.
  • the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave exuded by evanescent enters the substrate.
  • the method of introducing a diffraction grating into an interface that causes total reflection or in any medium has a feature that the effect of improving the light extraction efficiency is high.
  • This method was generated from the light-emitting layer by utilizing the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction, such as first-order diffraction or second-order diffraction.
  • Bragg diffraction such as first-order diffraction or second-order diffraction.
  • light that cannot be emitted due to total reflection between layers, etc. is diffracted by introducing a diffraction grating into any layer or medium (in the transparent substrate or transparent electrode). Is going to be taken out.
  • the diffraction grating to be introduced has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. The light extraction efficiency does not increase so much.
  • the refractive index distribution a two-dimensional distribution
  • the light traveling in all directions is diffracted, and the light extraction efficiency is increased.
  • the position where the diffraction grating is introduced may be in any interlayer or medium (in the transparent substrate or transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.
  • the period of the diffraction grating is preferably in the range of about 1/2 to 3 times the wavelength of light in the medium.
  • the arrangement of the diffraction gratings is preferably two-dimensionally repeated, such as a square lattice, a triangular lattice, or a honeycomb lattice.
  • the organic EL element of the present invention can be processed to provide a structure on a microlens array, for example, on the light extraction side of a support substrate (substrate), or combined with a so-called condensing sheet, for example, in a specific direction, for example, the element Condensing light in the front direction with respect to the light emitting surface can increase the luminance in a specific direction.
  • a quadrangular pyramid having a side of 30 ⁇ m and an apex angle of 90 degrees is arranged two-dimensionally on the light extraction side of the substrate.
  • One side is preferably within a range of 10 to 100 ⁇ m. If it becomes smaller than this, the effect of diffraction will generate
  • the condensing sheet it is possible to use, for example, an LED backlight of a liquid crystal display device that has been put into practical use.
  • a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
  • the shape of the prism sheet for example, the substrate may be formed with a triangle stripe having a vertex angle of 90 degrees and a pitch of 50 ⁇ m, or the vertex angle is rounded, and the pitch is randomly changed. It may be a shape or other shapes.
  • a light diffusion plate / film may be used in combination with the light collecting sheet.
  • a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.
  • the organic EL element of the present invention can be used as a display device, a display, and various light emission sources.
  • lighting devices home lighting, interior lighting
  • clock and liquid crystal backlights billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light
  • the light source of a sensor etc. are mentioned, It is not limited to this, Especially, it can use effectively for the use as a backlight of a liquid crystal display device, and a light source for illumination.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like during film formation, if necessary.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned.
  • a conventionally known method is used. Can do.
  • the display device of the present invention comprises the organic EL element of the present invention.
  • the display device of the present invention may be single color or multicolor, but here, the multicolor display device will be described.
  • a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by a vapor deposition method, a cast method, a spin coat method, an ink jet method, a printing method, or the like.
  • the method is not limited, but is preferably a vapor deposition method, an inkjet method, a spin coating method, or a printing method.
  • the configuration of the organic EL element included in the display device is selected from the above-described configuration examples of the organic EL element as necessary.
  • the manufacturing method of an organic EL element is as having shown in the one aspect
  • a DC voltage When a DC voltage is applied to the obtained multicolor display device, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode. Further, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the-state.
  • the alternating current waveform to be applied may be arbitrary.
  • the multicolor display device can be used as a display device, a display, and various light sources.
  • a display device or display full-color display is possible by using three types of organic EL elements of blue, red, and green light emission.
  • Display devices and displays include televisions, personal computers, mobile devices, AV devices, teletext displays, information displays in automobiles, and the like. In particular, it may be used as a display device for reproducing still images and moving images, and the driving method when used as a display device for reproducing moving images may be either a simple matrix (passive matrix) method or an active matrix method.
  • Light sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, light sources for optical sensors, etc.
  • the present invention is not limited to these examples.
  • FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements. It is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.
  • the display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
  • the control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside, and the pixels for each scanning line respond to the image data signal by the scanning signal.
  • the image information is sequentially emitted to scan the image and display the image information on the display unit A.
  • FIG. 2 is a schematic diagram of the display unit A.
  • the display unit A has a wiring unit including a plurality of scanning lines 5 and data lines 6 and a plurality of pixels 3 on the substrate.
  • the main members of the display unit A will be described below.
  • the light L emitted from the pixel 3 is extracted in the direction of the white arrow (downward).
  • the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions (details are illustrated Not)
  • the pixel 3 When the scanning signal is applied from the scanning line 5, the pixel 3 receives the image data signal from the data line 6 and emits light according to the received image data.
  • a full color display can be achieved by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.
  • FIG. 3 is a circuit diagram of the pixel.
  • the pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like.
  • a full color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 in a plurality of pixels, and juxtaposing them on the same substrate.
  • an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6.
  • a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5
  • the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is supplied to the capacitor 13 and the driving transistor 12. Is transmitted to the gate.
  • the capacitor 13 is charged according to the potential of the image data signal, and the drive transistor 12 is turned on.
  • the drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10, and the power supply line 7 connects to the organic EL element 10 according to the potential of the image data signal applied to the gate. Current is supplied.
  • the capacitor 13 maintains the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied. Until then, the light emission of the organic EL element 10 continues.
  • the driving transistor 12 When the scanning signal is next applied by sequential scanning, the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
  • the light emission of the organic EL element 10 is performed by providing the switching transistor 11 and the drive transistor 12 which are active elements with respect to the organic EL element 10 of each of the plurality of pixels, and the light emission of the organic EL element 10 of each of the plurality of pixels 3. It is carried out.
  • Such a light emitting method is called an active matrix method.
  • the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or by turning on / off a predetermined light emission amount by a binary image data signal. Good.
  • the potential of the capacitor 13 may be maintained until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
  • the present invention not only the active matrix method described above, but also a passive matrix light emission drive in which an organic EL element emits light according to a data signal only when a scanning signal is scanned.
  • FIG. 4 is a schematic view of a passive matrix display device.
  • a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
  • the pixel 3 connected to the applied scanning line 5 emits light according to the image data signal.
  • the lighting device of the present invention will be described.
  • the illuminating device of this invention has the said organic EL element.
  • the organic EL element of the present invention may be used as an organic EL element having a resonator structure.
  • the purpose of use of the organic EL element having such a resonator structure is as follows.
  • the light source of a machine, the light source of an optical communication processing machine, the light source of a photosensor, etc. are mentioned, However It is not limited to these. Moreover, you may use for the said use by making a laser oscillation.
  • the organic EL element of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a device (display).
  • the drive method when used as a display device for moving image reproduction may be either a simple matrix (passive matrix) method or an active matrix method.
  • the organic EL device of the present invention can be an organic EL device that emits white light.
  • An organic EL element that emits white light can be applied to the lighting device.
  • a plurality of light emitting colors can be simultaneously emitted by a plurality of light emitting materials to obtain white light emission by color mixing.
  • the combination of a plurality of emission colors may include three emission maximum wavelengths of the three primary colors of blue, green, and blue, or two using the relationship of complementary colors such as blue and yellow, blue green and orange, etc.
  • the thing containing the light emission maximum wavelength may be used.
  • the combination of luminescent materials for obtaining a plurality of luminescent colors is a combination of a plurality of phosphorescent or fluorescent materials or a combination of fluorescent or phosphorescent materials. Any combination of a light emitting material that emits light and a dye material that emits light from the light emitting material as excitation light may be used. However, in the organic EL device that emits white light according to the present invention, a plurality of light emitting dopants are combined. It can also be mixed.
  • an electrode film can be formed by a vapor deposition method, a cast method, a spin coating method, an ink jet method, a printing method, or the like, and productivity is also improved.
  • the element itself emits white light.
  • luminescent material used for a light emitting layer For example, if it is a backlight in a liquid crystal display element, the metal complex which concerns on this invention so that it may suit the wavelength range corresponding to CF (color filter) characteristic, Any one of known luminescent materials may be selected and combined to whiten.
  • CF color filter
  • the non-light emitting surface of the organic EL device of the present invention is covered with a glass case, a glass substrate having a thickness of 300 ⁇ m is used as a sealing substrate, and an epoxy photocurable adhesive (LUX TRACK manufactured by Toagosei Co., Ltd.) is used as a sealing material around LC0629B) is applied, and this is overlaid on the cathode and brought into close contact with the transparent support substrate, irradiated with UV light from the glass substrate side, cured and sealed, and an illumination device as shown in FIGS. Can be formed.
  • an epoxy photocurable adhesive (LUX TRACK manufactured by Toagosei Co., Ltd.) is used as a sealing material around LC0629B) is applied, and this is overlaid on the cathode and brought into close contact with the transparent support substrate, irradiated with UV light from the glass substrate side, cured and sealed, and an illumination device as shown in FIGS. Can be formed.
  • FIG. 5 shows a schematic diagram of a lighting device, and the organic EL element 101 of the present invention is covered with a glass cover 102 (in addition, the sealing operation with the glass cover is to bring the organic EL element 101 into contact with the atmosphere. And preferably in a glove box under a nitrogen atmosphere (in an atmosphere of high-purity nitrogen gas having a purity of 99.999% or more).
  • FIG. 6 shows a cross-sectional view of the lighting device.
  • 105 denotes a cathode
  • 106 denotes an organic EL layer
  • 107 denotes a glass substrate with a transparent electrode.
  • This ITO transparent electrode is provided after patterning on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) as an anode on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum vapor deposition apparatus.
  • 200 mg of HT-1 as a hole injection material is put into a molybdenum resistance heating boat
  • HT- as a hole transport material is put into a molybdenum resistance heating boat.
  • 100 mg of D-63 was added and attached to a vacuum deposition apparatus.
  • the vacuum chamber was then depressurized to 4 ⁇ 10 ⁇ 4 Pa, heated by energizing the heating boat containing HT-1, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / sec.
  • the second hole transport layer was provided.
  • the heating boat containing HT-2 was energized and heated, and was deposited on the transparent support substrate at a deposition rate of 0.1 nm / second to provide a second hole transport layer having a layer thickness of 20 nm.
  • the heating boat containing HS-1 as a host compound and D-63 as a phosphorescent metal complex was energized and heated, and the above-mentioned first deposition was performed at a deposition rate of 0.1 nm / second and 0.009 nm / second, respectively.
  • a light-emitting layer having a thickness of 40 nm was provided by co-evaporation on the two-hole transport layer.
  • the heating boat containing ET-1 was energized and heated, and was deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a layer thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride was vapor-deposited to form a cathode buffer layer having a layer thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a layer thickness of 110 nm.
  • an organic EL element 1-1 was produced.
  • a 100 mm ⁇ 100 mm ⁇ 1.1 mm quartz substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a thin film provided only with a light emitting layer was also produced.
  • organic EL elements 1-2 to 1-8 and thin films only of the light emitting layers of the respective organic electroluminescence elements were produced in the same manner.
  • the thin film having only the light-emitting layer was irradiated with ultraviolet light having an excitation wavelength of 280 nm at room temperature (25 ° C.), the attenuation of the intensity of the light emission maximum wavelength was fitted, and the phosphorescence lifetime ( ⁇ ) was measured.
  • a small fluorescent lifetime measuring device C11367 manufactured by Hamamatsu Photonics was used for phosphorescence lifetime measurement.
  • the phosphorescence lifetime is shown in the table as a relative value set to 100 for a thin film of only the light emitting layer of the organic EL element 1-1 produced together with the organic EL element 1-1.
  • the thin film having only the light emitting layer was irradiated with ultraviolet light having an excitation wavelength of 280 nm in a nitrogen atmosphere at room temperature (25 ° C.), and the absolute quantum yield (PLQE) was measured.
  • An absolute PL quantum yield measuring device C11347 manufactured by Hamamatsu Photonics was used for the absolute quantum yield measurement.
  • the absolute quantum yield is shown in the following table as a relative value in which the thin film of the organic EL element 1-1 having only the light emitting layer is set to 100.
  • the organic EL element was subjected to continuous light emission under a constant luminance condition of 4000 cd / cm 2 at a constant current at room temperature, and the time ( ⁇ 1/2 ) required to obtain half the initial luminance was measured.
  • the light emission lifetime is shown in the following table as a relative value with the organic EL element 1-1 set to 100.
  • CS-2000 manufactured by Konica Minolta Co., Ltd. was used to measure the luminance of the organic EL element.
  • Table 1 shows the evaluation results of the organic EL element and the thin film only of the light emitting layer.
  • the change in the emission color of the organic EL elements 1-2 to 1-8 relative to the organic EL element 1-1 was less than 0.015 in the (x, y) color coordinates in the 1931 color system.
  • the organic EL device further using the non-luminescent metal compound (D2) having an atomic number larger than that of the phosphorescent metal complex (D1) is more problematic than the comparative organic EL device. It is clear that the phosphorescent lifetime of the material is shortened and the lifetime is increased. Further, when Au or Bi having a larger atomic number is used, the above-described effect is remarkable.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum vapor deposition apparatus.
  • 200 mg of HT-1 as a hole injection material is put into a molybdenum resistance heating boat
  • HT- as a hole transport material is put into a molybdenum resistance heating boat.
  • 100 mg of D-17 was placed and attached to a vacuum deposition apparatus.
  • the vacuum chamber was then depressurized to 4 ⁇ 10 ⁇ 4 Pa, heated by energizing the heating boat containing HT-1, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / sec.
  • the second hole transport layer was provided.
  • the heating boat containing HT-2 was energized and heated, and was deposited on the transparent support substrate at a deposition rate of 0.1 nm / second to provide a second hole transport layer having a layer thickness of 20 nm.
  • the heating boat containing HS-1 as a host compound and D-17 as a phosphorescent metal complex was energized and heated, and the second rate was set at a deposition rate of 0.1 nm / second and 0.006 nm / second, respectively.
  • a light-emitting layer having a thickness of 40 nm was provided by co-evaporation on the hole transport layer.
  • the heating boat containing ET-1 was energized and heated, and was deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a layer thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • a quartz substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a thin film provided only with a light emitting layer was also produced.
  • organic EL elements 2-2 to 2-7 and the thin film only of the light emitting layer of each organic electroluminescence element were produced in the same manner.
  • the organic EL device further using the non-luminescent metal compound (D2) having a larger atomic number than the phosphorescent metal complex (D1) is more problematic than the comparative organic EL device. It is clear that the phosphorescent lifetime of the material is shortened and the lifetime is increased. Further, when Au or Bi having a larger atomic number is used, the above-described effect is remarkable.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum vapor deposition apparatus.
  • 200 mg of HT-1 as a hole injection material is put into a molybdenum resistance heating boat
  • HT- as a hole transport material is put into a molybdenum resistance heating boat
  • a phosphorescent metal complex 100 mg of D-1 was added and attached to a vacuum deposition apparatus.
  • the vacuum chamber was then depressurized to 4 ⁇ 10 ⁇ 4 Pa, heated by energizing the heating boat containing HT-1, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / sec.
  • the first hole transport layer was provided.
  • the heating boat containing HT-2 was energized and heated, and was deposited on the transparent support substrate at a deposition rate of 0.1 nm / second to provide a second hole transport layer having a layer thickness of 20 nm.
  • the heating boat containing HS-3 as a host compound and D-1 as a phosphorescent metal complex was energized and heated, and the second rate was set at a deposition rate of 0.1 nm / second and 0.006 nm / second, respectively.
  • a light-emitting layer having a thickness of 40 nm was provided by co-evaporation on the hole transport layer.
  • the heating boat containing ET-1 was energized and heated, and was deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a layer thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride was vapor-deposited to form a cathode buffer layer having a thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a thickness of 110 nm.
  • an organic EL element 3-1 was produced.
  • a 100 mm ⁇ 100 mm ⁇ 1.1 mm quartz substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a thin film provided only with a light emitting layer was also produced.
  • organic EL elements 3-2 to 3-7 and thin films only of the light emitting layer of each organic electroluminescence element were produced in the same manner.
  • the change in the emission color of the organic EL elements 3-2 to 3-7 relative to the organic EL element 3-1 was less than 0.015 in the (x, y) color coordinates in the 1931 color system.
  • the organic EL device using the non-luminescent metal compound (D2) having a larger atomic number than the phosphorescent metal complex (D1) is more problematic than the comparative organic EL device. It is clear that the phosphorescent lifetime of the material is shortened and the lifetime is increased. Further, when Au or Bi having a larger atomic number is used, the above-described effect is remarkable.
  • Example 4 Preparation of organic EL element 4-1 >> Patterning was performed on a substrate (NA-45, manufactured by AvanState Co., Ltd.) on which a 100 nm ITO film was formed as an anode on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate. Thereafter, the transparent support substrate provided with the ITO transparent electrode was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) diluted to 70% with pure water was used to spin. After forming a thin film by the coating method, it was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a layer thickness of 30 nm.
  • a hole transport material Poly N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl)) benzidine (manufactured by American Dye Source, ADS- A thin film was formed by spin coating using the chlorobenzene solution of No. 254). Heat drying at 150 ° C. for 1 hour to provide a second hole transport layer having a layer thickness of 40 nm.
  • a thin film is formed on this second hole transport layer by spin coating using a solution in which 90 mg of HS-2 as a host compound and 10 mg of D-63 as a phosphorescent metal complex are dissolved in butyl acetate. And dried by heating at 120 ° C. for 1 hour to provide a light-emitting layer having a layer thickness of 30 nm.
  • a 1-butanol solution of ET-1 as an electron transport material was used to form a thin film by spin coating, and an electron transport layer having a layer thickness of 20 nm was provided.
  • This substrate was attached to a vacuum deposition apparatus, and the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa.
  • lithium fluoride was vapor-deposited to form an electron injection layer having a thickness of 1.0 nm
  • aluminum was vapor-deposited to form a cathode having a thickness of 110 nm.
  • an organic EL element 4-1 was produced.
  • a quartz substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a thin film provided only with a light emitting layer was also produced.
  • organic EL elements 4-2 to 4-7 and thin films only of the light emitting layer of each organic electroluminescence element were produced in the same manner.
  • the change in emission color of the organic EL elements 4-2 to 4-7 relative to the organic EL element 4-1 was less than 0.015 in the (x, y) color coordinates in the 1931 color system.
  • the organic EL device using the non-luminescent metal compound (D2) having a larger atomic number than the phosphorescent metal complex (D1) is more problematic than the comparative organic EL device. It is clear that the phosphorescent lifetime of the material is shortened and the lifetime is increased. Further, when Au or Bi having a larger atomic number is used, the above-described effect is remarkable.
  • Example 5 ⁇ Preparation of white light-emitting organic EL element 5-1 >> After patterning on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate with a 100 nm ITO film (NA45 manufactured by NH Techno Glass) as an anode, the transparent support substrate provided with this ITO transparent electrode was treated with isopropyl alcohol. Was subjected to ultrasonic cleaning, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.
  • ITO film NA45 manufactured by NH Techno Glass
  • a poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) diluted to 70% with pure water was used to spin. After forming a thin film by the coating method, it was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a layer thickness of 30 nm.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum vapor deposition apparatus.
  • 200 mg of HT-2 as a hole transport material is placed in a molybdenum resistance heating boat, and HS- 200 mg of 1 is added, 200 mg of HS-3 as a host compound is put in another molybdenum resistance heating boat, 200 mg of ET-1 is put in another molybdenum resistance heating boat as an electron transport material, and the other resistance heating boat made of molybdenum 100 mg of D-63 as a phosphorescent metal complex, 100 mg of D-17 as a phosphorescent metal complex are put in another molybdenum resistance heating boat, and a phosphorescent metal complex is put in another molybdenum resistance heating boat.
  • 100 mg of D-1 was added and attached to a vacuum deposition apparatus.
  • each of the heating boats containing HT-2 was energized separately, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second.
  • a first hole transport layer was provided.
  • the heating boat containing HS-3 as the host compound and D-17 and D-1 as the phosphorescent metal complex was energized to adjust the deposition rate to 100: 1: 0.3. Then, a first light emitting layer having a layer thickness of 30 nm was provided. Further, the heating boat containing HS-1 as the host compound and D-63 as the phosphorescent metal complex is energized to adjust the deposition rate of HS-1 and D-63 to 100: 15. A second light emitting layer having a layer thickness of 30 nm was provided.
  • the heating boat containing ET-1 was energized and heated, and deposited on the second light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a layer thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride was vapor-deposited to form a cathode buffer layer having a thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a thickness of 110 nm.
  • an organic EL element 5-1 was produced.
  • a quartz substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a thin film provided only with a light emitting layer was also produced.
  • organic EL elements 5-2 to 5-7 and the thin film only of the light emitting layer of each organic electroluminescence element were produced in the same manner.
  • the organic EL device using the non-luminescent metal compound (D2) having a larger atomic number than the phosphorescent metal complex (D1) is more problematic than the comparative organic EL device. It is clear that the phosphorescent lifetime of the material is shortened and the lifetime is increased. Further, when Au or Bi having a larger atomic number is used, the above-described effect is remarkable.
  • Example 6 ⁇ Production of display device >> (Blue light emitting organic EL device)
  • the organic EL device 1-6 having two metal compounds according to the present invention in Example 1 was used as a blue light emitting device.
  • Green light-emitting organic EL device The organic EL element 2-5 having two metal compounds according to the present invention in Example 2 was used as a green light emitting element.
  • the organic EL device 3-5 having two metal compounds according to the present invention in Example 3 was used as a red light emitting device.
  • the red, green, and blue light emitting organic EL elements produced above were juxtaposed on the same substrate to produce an active matrix type full color display device having a configuration as shown in FIG. In FIG. 2, only the schematic diagram of the display part A of the produced display device is shown.
  • a plurality of pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) juxtaposed with a wiring portion including a plurality of scanning lines 5 and data lines 6 on the same substrate.
  • the scanning lines 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions.
  • the plurality of pixels 3 are driven by an active matrix system provided with an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5.
  • the image data signal is received from the data line 6 and light is emitted according to the received image data. In this way, a full color display device was produced by appropriately juxtaposing red, green, and blue pixels.
  • the electroluminescence element of the present invention has a long lifetime and can be preferably applied to lighting devices and display devices.

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  • Engineering & Computer Science (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

Un objectif de la présente invention est de pourvoir à un élément électroluminescent organique qui possède une longue durée de service par obtention d'un raccourcissement de la durée de vie de phosphorescence. Un autre objectif de la présente invention est de pourvoir à un dispositif d'éclairage et un dispositif d'affichage comprenant chacun cet élément électroluminescent organique. Un élément électroluminescent organique selon la présente invention comprend une couche électroluminescente entre une électrode positive et une électrode négative, et la couche électroluminescente contient, comme dopants, au moins deux composés métalliques. Cet élément électroluminescent organique est caractérisé en ce que : au moins un des composés métalliques est un complexe métallique phosphorescent (D1) ; au moins un des composés métalliques est un composé métallique non luminescent (D2) ; et le numéro atomique du métal qui constitue le composé métallique non luminescent est plus grand que le numéro atomique du métal central du complexe métallique phosphorescent.
PCT/JP2015/082187 2014-11-25 2015-11-17 Élément électroluminescent organique, et dispositif d'éclairage et dispositif d'affichage le comprenant chacun WO2016084648A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003077674A (ja) * 2000-10-04 2003-03-14 Mitsubishi Chemicals Corp 有機電界発光素子
JP2005255891A (ja) * 2004-03-12 2005-09-22 Toyo Ink Mfg Co Ltd 有機燐光発光素子用材料およびそれを用いた有機燐光発光素子
JP2006270053A (ja) * 2005-02-28 2006-10-05 Fuji Photo Film Co Ltd 有機電界発光素子
JP2013191879A (ja) * 2006-04-20 2013-09-26 Universal Display Corp 多重ドーパント発光層有機発光デバイス
JP2013538453A (ja) * 2010-08-24 2013-10-10 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 光活性組成物、およびその組成物を用いて作製した電子デバイス

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003077674A (ja) * 2000-10-04 2003-03-14 Mitsubishi Chemicals Corp 有機電界発光素子
JP2005255891A (ja) * 2004-03-12 2005-09-22 Toyo Ink Mfg Co Ltd 有機燐光発光素子用材料およびそれを用いた有機燐光発光素子
JP2006270053A (ja) * 2005-02-28 2006-10-05 Fuji Photo Film Co Ltd 有機電界発光素子
JP2013191879A (ja) * 2006-04-20 2013-09-26 Universal Display Corp 多重ドーパント発光層有機発光デバイス
JP2013538453A (ja) * 2010-08-24 2013-10-10 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 光活性組成物、およびその組成物を用いて作製した電子デバイス

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