WO2007119420A1 - Élément électroluminescent organique, procédé de stabilisation de la chromaticité d'émission de l'élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage électronique - Google Patents

Élément électroluminescent organique, procédé de stabilisation de la chromaticité d'émission de l'élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage électronique Download PDF

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WO2007119420A1
WO2007119420A1 PCT/JP2007/055507 JP2007055507W WO2007119420A1 WO 2007119420 A1 WO2007119420 A1 WO 2007119420A1 JP 2007055507 W JP2007055507 W JP 2007055507W WO 2007119420 A1 WO2007119420 A1 WO 2007119420A1
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organic
light
layer
emission
light emitting
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PCT/JP2007/055507
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Japanese (ja)
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Hiroshi Kita
Tatsuo Tanaka
Hideo Taka
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Konica Minolta Holdings, Inc.
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Priority to JP2008510813A priority Critical patent/JP5051125B2/ja
Publication of WO2007119420A1 publication Critical patent/WO2007119420A1/fr

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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Definitions

  • ORGANIC ELECTRIC LIGHT EMITTING ELEMENT METHOD FOR STABILIZING EMISSION COLOR OF ORGANIC ELECTRIC LIGHT EMITTING ELEMENT
  • the present invention relates to an organic electoluminescence device, a method for stabilizing luminescence chromaticity of an organic electroluminescence device, an illumination device, and an electronic display device.
  • ELD electoric luminescence display
  • inorganic electoluminescence devices and organic electroluminescence devices (hereinafter also referred to as organic EL devices).
  • organic EL devices Inorganic eletroluminescence elements have been used as planar light sources, but in order to drive the light emitting elements, an alternating high voltage is required.
  • an organic EL element has a configuration in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode.
  • excitons Is an element that emits light by utilizing the emission of light (fluorescence / phosphorescence) when the exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts. Since it is a self-emitting type, it has a wide viewing angle, and since it is a thin-film type completely solid element with high visibility, it is attracting attention from the viewpoints of space saving and portability.
  • Patent No. 309379 6 discloses a technique for doping a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative with a trace amount of a phosphor to improve emission luminance and extend the lifetime of the device.
  • — 264692 discloses a device having an organic light-emitting layer in which 8-hydroxyquinoline aluminum complex is a host compound and doped with a small amount of phosphor.
  • JP-A-3-255190 discloses An element having an organic light-emitting layer in which an 8-hydroxyquinoline aluminum complex is used as a host compound and doped with a quinacridone dye is known. [0005] In the technique disclosed in the above patent document, when light emission from excited singlet is used, the generation ratio of singlet excitons and triplet excitons is 1: 3, so the generation probability of luminescent excited species Is 25% and the light extraction efficiency is about 20%, so the limit of external extraction quantum efficiency ( ⁇ ext) is 5%.
  • the organic EL element is an all-solid element composed of an organic material film having a thickness of only about 0.1 ⁇ m between the electrodes, and its emission is relatively 2V to 20V. Because it can be achieved at a low voltage, it is a promising technology for next-generation flat displays and lighting.
  • organic EL elements are based on a light-emitting phenomenon utilizing the deactivation of organic materials from the excited state to the ground state, blue, blue-green, etc.
  • a high voltage is required to excite the large gap.
  • the excited state itself is located at a high level, the lifetime tends to be shorter than that of green or red light emission, which is greatly damaged when returning to the ground state, and in particular, light emission from the triplet excited state. This tendency becomes remarkable in phosphorescence emission using the.
  • Patent Document 2 Like the material having a bur group at the end of the phosphorescent dopant, the radical generator AIBN (azoisopetiti-tolyl) is added to the mixture of comonomers having a vinyl group during film formation.
  • AIBN azoisopetiti-tolyl
  • a production method for causing a polymerization reaction to proceed for example, see Patent Document 3
  • a production method for causing a Diels-Alder reaction between two molecules in the same layer for example, see Patent Document 4
  • the above-described technique is a method of completing the polymerization reaction at the time of film formation or immediately after film formation (before attaching the cathode), but also has a practical viewpoint power of improving the durability of the organic EL element. However, this is insufficient, and there is a need for further technology for improving the durability of elements.
  • Patent Document 1 Japanese Patent Laid-Open No. 5-271166
  • Patent Document 2 Japanese Patent Laid-Open No. 2001-297882
  • Patent Document 3 Japanese Patent Laid-Open No. 2003-73666
  • Patent Document 4 Japanese Unexamined Patent Publication No. 2003-86371
  • the present invention has been made in view of the above problems, and an object of the present invention is to provide an organic electoluminescence device that has less variation in emission chromaticity and has improved robustness by use of the device, To provide a display device and a lighting device using the element.
  • an organic electoluminescence device having an organic compound layer having at least an anode and a cathode on a support substrate, and an organic compound layer including at least one light emitting layer between the anode and the cathode,
  • One layer contains the luminescent material A whose emission spectrum shifts to the short wavelength side when energized, and is an organic electoluminescence device.
  • the light-emitting material A and the light-emitting material A containing at least one light-emitting material B exhibiting a light emission vector having a shorter wavelength than an initial light emission wavelength of the light-emitting material A The organic-elect mouth luminescence element described.
  • An illuminating device comprising the organic electoluminescence element according to any one of 1 to 7 above.
  • An electronic display device comprising the organic-electric-luminescence element according to any one of 1 to 7 above.
  • an organic electoluminescence device having little variation in emission chromaticity and improved fastness by use of the device, a method for stabilizing the emission chromaticity of an organic electoluminescence device, and the device It was possible to provide a display device and a lighting device to be used.
  • FIG. 1 is a schematic diagram showing an example of an organic EL device of the present invention.
  • FIG. 2 is a schematic view showing an example of the organic EL device of the present invention.
  • FIG. 3 is a schematic view showing an example of the organic EL device of the present invention.
  • FIG. 4 is a schematic view showing an example of the organic EL device of the present invention.
  • FIG. 5 is a schematic view showing an example of the organic EL device of the present invention.
  • FIG. 6 is a schematic view showing an example of the organic EL device of the present invention.
  • FIG. 7 is a schematic view of a lighting device.
  • FIG. 8 is a cross-sectional view of the lighting device.
  • the organic electoluminescence device also referred to as an organic EL device
  • the organic electoluminescence device has the configuration described in any one of claims 1 to 7.
  • an organic electroluminescence element organic EL element in which the variation in emission chromaticity is small and the robustness is improved by using the element was obtained.
  • the organic EL device emit light under a specific luminance condition
  • a light emission chromaticity stabilization method that can suppress a change in chromaticity over time of light emission at a practically sufficient level has been successfully established.
  • a high-luminance display device and lighting device have been successfully obtained.
  • An organic EL element utilizes a light emission phenomenon when a light emitting material excited by an electric field returns to a ground state, and in principle, a high voltage is required to emit short-wave light. .
  • the light emitting material on the shorter wavelength side newly generated by energization may be a chain polymer with high thermal stability or a higher order Since it is possible to change to a network polymer, the conventional organic EL element has a major problem of chromaticity change of light emission over time by continuing energization from the initial use state.
  • the organic EL device of the present invention by continuing the light emission by energization, the robustness will be further enhanced, and it will be possible to realize an innovative organic EL device based on a completely new concept that has never been seen before. Successful.
  • the luminescent material A that is contained in at least one of the constituent layers (organic compound layers) of the organic EL device of the present invention and whose emission spectrum is shifted (moved) to the short wavelength side when the device is energized will be described.
  • the partial structure of the compound used for the light-emitting material A according to the present invention (this partial structure may include a functional site that emits light when the element is energized) is described later.
  • Various types of compounds, etc. are described that are described in the component layer of the device, including a hole transport layer, a hole injection layer, an electron injection layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron blocking layer. Partial structures contained in the compounds described in known patent documents and references can be used.
  • the light emitting material A according to the present invention is preferably contained in the light emitting layer of the organic EL device of the present invention.
  • a host compound which will be described later, Dopant (also known as luminescent dopant) or luminescent material that does not require doping, but dopant (luminescent dopant, where luminescent dopant includes phosphorescent dopant, fluorescent dopant) One punt is given. And particularly preferably a phosphorescent dopant.
  • the phosphorescent dopant and the fluorescent dopant will be described in detail in the constituent layers of the organic EL element described later.
  • the organic EL element of the present invention is allowed to emit light. It is important to utilize active species (such as active radicals), light (photons generated by light emission), or Joule heat generated inside the device, and the action of the active species, light
  • active species such as active radicals
  • light photons generated by light emission
  • the emission wavelength of the luminescent material A due to the action or chemical change due to Joule heat is in a state in which no change in the molecular structure occurs due to the above active species, light, Joule heat, etc. Is preferably shifted to the short wavelength side.
  • a substituent for shortening the emission wavelength of the light emitting material is added to the molecule of the light emitting material due to a reaction or action occurring in the device.
  • the conjugated system is expanded to lower the LUMO (lowest airway) energy level, to increase the HOMO (highest occupied orbital) energy level, or It is common to use either power or both to reduce the LUMO (lowest orbital) energy level by electronic effects, or to increase the HOMO (highest occupied orbit) energy level.
  • the luminescent material has a substituent shown below.
  • the light-emitting layer of the organic EL may be one in which all of the materials constituting the layer are light-emitting materials, and the light-emitting dopant and the light-emitting host may coexist. Further, a multicolor light emitting device in which a plurality of light emitting dopants may be present and a light emitting layer may be laminated may be used.
  • the chemical change of the light-emitting material may utilize a reaction with the light-emitting host.
  • a chemical reaction such as a combination may occur.
  • luminescent dopant when a chemical reaction with the luminescent host is used, it is preferable to introduce into the luminescent host a substituent capable of reacting with the reactive group substituted on the luminescent material (ie, luminescent dopant).
  • a hydroxyl group one OH
  • selecting a material having an isocyanate group (—NCO) or an isothiocyanate group (—NCS) as the luminescent host is advantageous.
  • phosphorescent device that utilizes phosphorescent light emission
  • mixing a phosphorescent dopant with a light emitting host in a mass ratio of about 1% to 20% is effective in terms of luminous efficiency.
  • a luminescent host in combination.
  • the luminescent host material is a reactive phosphorescent luminescent material (phosphorescent dopant). It is preferable to have a substituent capable of chemically reacting with.
  • the most preferable form is that at least one material in which a beryl group is substituted for both the light-emitting dopant and the light-emitting host are allowed to coexist in the same layer and pass through the light-emitting element.
  • an anion radical or a cation radical generated in the light emitting layer is used as a polymerization initiator to form a chain or network polymer.
  • the light-emitting element is more robust than the initial state, and it is possible to realize an ideal light-emitting element that gradually increases in durability before use.
  • P-1 to P-48 are compounds used as phosphorescent dopants
  • F-1, F-2 are compounds used as fluorescent dopants.
  • the luminescent material B according to the present invention will be described.
  • the light-emitting material B according to the present invention has a shorter wavelength than the light emission wavelength of the light-emitting material A at the initial light emission.
  • it is a material (a compound) showing a long emission spectrum, specifically, a material obtained by removing the reactive substituent from the light-emitting material A contained in the organic EL element is given as a preferred example. It is.
  • the light emitting material A according to the present invention may be simply a compound (both materials! And u) having an emission wavelength shorter than the initial emission wavelength of the light emitting material A! /, .
  • the light emission wavelength region of the light emitting material B is close to the light emission wavelength region that is newly developed when the light emitting material A is chemically structurally modified by energization.
  • the layer in which B is present may be the same layer as A or a different layer.
  • a luminescent material may be present, and the luminescent material may be substituted with a reactive substituent such as A.
  • the chemical structural modification means that the luminescent material A itself undergoes a chemical reaction when the element is energized (for example, the luminescent material A having the above-described substituents is activated radicals when energized.
  • the luminescent material A having the above-described substituents is activated radicals when energized.
  • seeds are generated and a self-polymerization or copolymerization reaction is initiated, a polymer is formed, and a compound having a substituent capable of condensing with a reactive group of compound A and a compound A are condensed by Joule heat generated by force.
  • An example of this is a case where a film physical property starting from an isomer to a structural isomer is changed).
  • conventionally known phosphorescent dopants, fluorescent dopants and the like used for the light emitting layer in the constituent layers of the organic EL element described later are also used as the light emitting material B according to the present invention. Is possible.
  • the luminescent material A and the material C capable of reacting in the organic compound layer will be described.
  • the material capable of reacting in the organic compound layer according to the present invention preferably has the above-described substituent as described in claim 5 of the present application.
  • it is a material that can be copolymerized or polycondensed with the active species of the light-emitting material A that is generated by energization of the element.
  • a specific example of the material C is a compound having a function as a light-emitting host compound. It is a thing.
  • C is preferably present in the same layer as the light-emitting material A, but may be present in any layer other than the light-emitting layer, for example, an electron transport layer, a hole transport layer, or an intermediate layer.
  • the organic EL device of the present invention contains a light emitting material whose emission wavelength is gradually shortened during use (light emission at a necessary luminance), and the emission spectrum based on the light emitting material is shortened. As a result, we have completed a technology that effectively compensates for the emission color that decays over time.
  • Energization for changing the light emission of the organic EL device of the present invention to a shorter wave emission spectrum also referred to as light emission having a shorter emission wavelength or a shorter emission peak
  • a shorter wave emission spectrum also referred to as light emission having a shorter emission wavelength or a shorter emission peak
  • the current density at that time which is a so-called DC drive in which a current is continuously passed, a so-called pulse drive in which a current is intermittently passed, or even an AC drive.
  • the viewpoint that the emission spectrum gradually changes during use at least one emission spectrum shape of the light emitting material in the light emitting element changes) and substantially compensates the emission color.
  • the current density is set to 0. OlmA / cm 'to 1000 mAZcm 2 It is preferable to energize within the range.
  • the constituent layers of the organic EL device of the present invention will be described.
  • preferred specific examples of the layer structure of the organic EL element are shown below, but the present invention is not limited thereto.
  • the maximum emission wavelength of the blue light emitting layer is 430 ⁇ !
  • the green light emitting layer that is preferred at ⁇ 480 nm has a maximum emission wavelength of 510 nm to 550 nm, and the red emission layer has a maximum emission wavelength of 600 ⁇ !
  • a monochromatic light emitting layer in the range of ⁇ 640 nm is preferred, and a display device using these is preferred.
  • a white light emitting layer may be formed by laminating at least three of these light emitting layers.
  • a non-light emitting intermediate layer may be provided between the light emitting layers. It is preferable that the organic EL element of the present invention is a lighting device using these, which is preferably a white light emitting layer.
  • the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from an electrode, an electron transport layer, or a hole transport layer, and the light emitting portion is within the layer of the light emitting layer. It 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 it can prevent the film from being homogenous, applying an unnecessary high voltage during light emission, and improving the stability of the emitted color with respect to the drive current. From the viewpoint, it is preferable to adjust to the range of 2 ⁇ to 5 / ⁇ ⁇ , more preferably to the range of 2 nm to 200 nm, and particularly preferably in the range of 10 nm to 100 nm.
  • a light emitting dopant or a host compound described later is formed by a known thin film method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or an ink jet method. Can be formed.
  • the light-emitting layer of the organic EL device of the present invention may contain a light-emitting host compound and at least one light-emitting dopant (such as a phosphorescent dopant (also referred to as a phosphorescent dopant) or a fluorescent dopant). preferable.
  • a light-emitting dopant such as a phosphorescent dopant (also referred to as a phosphorescent dopant) or a fluorescent dopant.
  • the host compound used in the present invention will be described.
  • the host compound in the present invention is a compound having a mass ratio of 20% or more in the light-emitting layer and phosphorescence at room temperature (25 ° C).
  • Luminescence phosphorescence is defined as a compound with a quantum yield of less than 0.1.
  • the phosphorescence quantum yield is less than 0.01.
  • the mass ratio in the layer is 20% or more. It is preferable that it is above.
  • host compound known host compounds may be used singly or in combination. By using a plurality of types of host compounds, it is possible to adjust the movement of electric charges, and the organic EL device can be made highly efficient. In addition, by using a plurality of kinds of light emitting dopants described later, it becomes possible to mix different light emission, thereby obtaining any light emission color.
  • the light emitting host used in the present invention is a low molecular weight compound having a polymerizable group such as a bur group or an epoxy group, which may be a conventionally known low molecular compound or a high molecular compound having a repeating unit.
  • a compound (evaporation polymerizable light-emitting host) or a compound such as the material C may be used alone or in combination.
  • Known host compounds that may be used in combination have a hole transporting ability and an electron transporting ability, prevent the emission of longer wavelengths, and have a high Tg (glass transition temperature). Compounds are preferred.
  • a fluorescent dopant also referred to as a fluorescent compound
  • a phosphorescent dopant also referred to as a phosphorescent emitter, a phosphorescent compound, a phosphorescent compound, or the like
  • the viewpoint of obtaining an organic EL element with higher luminous efficiency is the light emitting dopant used in the light emitting layer or light emitting unit of the organic EL element of the present invention (sometimes simply referred to as a light emitting material).
  • the phosphorescent dopant according to the present invention will be described.
  • the phosphorescent dopant according to the present invention is a compound in which emission of excited triplet force is observed, specifically, a compound that emits phosphorescence at room temperature (25 ° C).
  • a preferable phosphorescence quantum yield is 0.1 or more.
  • the phosphorescence 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. Phosphorescence quantum yield in solution can be measured using various solvents
  • the phosphorescence dopant according to the present invention achieves the above phosphorescence quantum yield (0.01 or more) in any solvent.
  • the phosphorescent dopant emits light in two types in principle. One is the recombination of carriers on the host compound in which carriers are transported, resulting in the generation of an excited state of the host compound.
  • the energy transfer type is to obtain light emission from the phosphorescent dopant by transferring the energy of the phosphorescent dopant to the phosphorescent dopant, and the other is that the phosphorescent dopant becomes a carrier trap, and recombination of carriers occurs on the phosphorescent dopant and causes phosphorescence. It is a carrier trap type in which light emission from the optical dopant can be obtained. In either case, the excited state energy of the phosphorescent dopant is required to be lower than the excited state energy of the host compound.
  • the phosphorescent dopant can be appropriately selected and used as a known medium used for the light emitting layer of the organic EL device.
  • the phosphorescent dopant according to the present invention is preferably a complex compound containing a metal of group 8 to LO in the periodic table of elements, more preferably an iridium compound, an osmium compound, or a platinum compound ( Platinum complex compounds), rare earth complexes, most preferred ⁇ is an iridium compound.
  • Fluorescent dopants include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes Examples thereof include dyes, perylene dyes, stilbene dyes, polythiophene dyes, and rare earth complex phosphors.
  • the injection layer is provided as necessary, and includes an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or hole transport layer and between the cathode and the light emitting layer or electron transport layer. Hey.
  • the injection layer is a layer provided between the electrode and the organic layer in order to reduce the driving voltage and improve the luminance of the light emission.
  • the organic EL element and the forefront of its industrialization June 30, 1998) (Published by ES Co., Ltd.) ”, Chapter 2“ Chapter 2 Electrode Materials ”(pages 123-166) in detail, the hole injection layer (anode buffer layer) and electron injection layer (cathode buffer layer) There is.
  • anode buffer layer (hole injection layer) The details of the anode buffer layer (hole injection layer) are also described in JP-A-9-45479, JP-A-9260062, JP-A-8-288069 and the like.
  • a phthalocyanine buffer layer typified by phthalocyanine, an oxide buffer layer typified by vanadium oxide, an amorphous carbon buffer layer, a polymer buffer layer using a conductive polymer such as polyarene (emeraldine) or polythiophene Etc.
  • cathode buffer layer (electron injection layer) The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like.
  • Metal buffer layer typified by aluminum or titanium
  • alkali metal compound buffer layer typified by lithium fluoride
  • alkaline earth metal compound buffer layer typified by magnesium fluoride
  • acid typified by acid aluminum
  • the buffer layer (injection layer) is preferably a very thin film, although the film thickness is preferably in the range of 0.1 nm to 5 m, although it depends on the desired material.
  • the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A-11 204258, 11-204359, and “Organic EL device and the forefront of its industrialization” (published by NTS Corporation on November 30, 1998). There is a hole blocking layer.
  • the hole blocking layer has the function of an electron transport layer and the function of transporting electrons.
  • the ability to transport holes is extremely small, and the hole recombination probability can be improved by blocking holes while transporting electrons.
  • the structure of the electron transport layer described later can be used as a hole blocking layer according to the present invention, if necessary.
  • the hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
  • the hole blocking layer preferably contains the azacarbazole derivative mentioned as the above-mentioned host compound.
  • the light emitting layer having the longest emission maximum wavelength is closest to the anode among all the light emitting layers.
  • 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more with respect to the host compound of the shortest wave emitting layer. Better!/,.
  • the ionic potential is defined by the energy required to release an electron at the HOMO (highest occupied molecular orbital) level of a compound to the vacuum level, and can be obtained by the following method, for example.
  • Gaussian98 (Gaussian98, Revision A. IV 1.4, MJ Frisch, et al, Lraussian, Inc., Pittsburg h PA, 2002.)
  • the ionization potential can be calculated by rounding off the second decimal place of the value (eV unit converted value) calculated by structural optimization using B3LYPZ6-31G * as a keyword. The reason why this calculated value is effective is that there is a high correlation between the calculated value obtained by this method and the experimental value.
  • the ion potential can also be obtained by a method of direct measurement by photoelectron spectroscopy.
  • a method known as ultraviolet photoelectron spectroscopy using a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd. can be suitably used.
  • the electron blocking layer has a function of a hole transport layer in a broad sense and is a mechanism for transporting holes.
  • the ability to transport electrons while having the capability is a material force that is extremely small, and the probability of recombination of electrons and holes can be improved by blocking electrons while transporting holes.
  • the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed.
  • the film thickness of the hole blocking layer and the electron transport layer according to the present invention is preferably 3 ⁇ ! ⁇ LOOnm, more preferably 5 ⁇ ! ⁇ 30nm.
  • the hole transport layer is a hole transport material having a function of transporting holes.
  • a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has any of hole injection or transport and electron barrier properties, and may be either organic or inorganic.
  • triazole derivatives for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, violazoline derivatives and pyrazolone derivatives, fluorenedamine derivatives, arylene amine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives
  • Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N'-tetraphenyl-1,4'-daminophenol; N, N' —Diphenyl N, N '— Bis (3-methylphenol) 1 [1, 1' — Biphenyl] 1, 4, 4 '— Diamine (TPD); 2, 2 Bis (4 di-p-tolylaminophenol 1, 1-bis (4 di-l-tri-laminophenol) cyclohexane; N, N, N ', N'—tetra-l-tolyl-1,4,4'-diaminobiphenyl; 1 Bis (4 di-p-triaminophenol) 4 Phenol mouth hexane; Bis (4-dimethylamino 2-methylphenol) phenylmethane; Bis (4-di-p-triaminophenol) phenol methane; N, N ' —Jihuel N, N '
  • a polymer material in which these materials are introduced into a polymer chain or these materials as a polymer main chain can also be used.
  • Inorganic compounds such as P-type-Si and p-type-SiC can also be used as the hole injection material and hole transport material.
  • the hole transport layer is formed by thin-filming the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. Can be formed.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • LB method
  • a hole transport layer having a high p property doped with impurities can be used. Examples thereof are described in JP-A-4-297076, JP-A-2000-196140, 2001-102175, J. Appl. Phys., 95, 5773 (2004), etc. Can be listed.
  • the electron transport layer is a material force 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.
  • An electron transport layer may be provided as a single layer or multiple layers.
  • an electron transport material also serving as a hole blocking material
  • Any material can be selected from conventionally known compounds as long as it has a function of transmitting electrons injected from the electrode to the light-emitting layer.
  • Examples include fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide oxide derivatives, strength rubodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like.
  • thiadiazole derivatives in which the oxygen atom of the oxaziazole ring is substituted with a sulfur atom
  • quinoxaline derivatives having a quinoxaline ring known as an electron-withdrawing group can also be used as the electron transporting material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • Metal complexes of 8 quinolinol derivatives such as tris (8 quinolinol) aluminum (Alq), tris (5,7-dichloro-1-8-quinolinol) aluminum, tris (5,7-dive mouth) 8 quinolinol) aluminum, tris (2methyl 8quinolinol) aluminum, tris (5-methyl 8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc.
  • the central metals of these metal complexes are In, Mg, Metal complexes replacing Cu, Ca, Sn, Ga or Pb can also be used as electron transport materials.
  • metal free or metal phthalocyanine, or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material.
  • the distyrylvirazine derivative exemplified as the material for the light-emitting layer can also be used as an electron transport material, and, like the hole injection layer and the hole transport layer, inorganic semiconductors such as n-type Si and n-type SiC Can also be used as an electron transporting material.
  • the electron transport layer is formed by using the above electron transport material, for example, vacuum deposition, spin coating, casting,
  • the film can be formed by thin film formation by a known method such as a printing method including an ink jet method, an ink jet method, or an LB method.
  • the film thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 ⁇ ! ⁇ 200nm.
  • the electron transport layer may have a single layer structure that can be one or more of the above materials.
  • an electron transport layer having a high n property doped with impurities can be used. Examples thereof are described in JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, Appl. Phys., 95, 5773 (2004), etc. The thing which was done is mentioned.
  • an electron transport layer having such a high ⁇ property because a device with lower power consumption can be produced.
  • an electrode material made of a metal, an alloy, an electrically conductive compound or a mixture thereof having a large work function (4 eV or more) is preferably used.
  • an electrode substance include metals such as Au, and conductive transparent materials such as Cul, indium tinoxide (IT 0), SnO, and ZnO.
  • IDIXO In O—ZnO
  • Electrode materials can be formed into a thin film by vapor deposition or sputtering, and a pattern of the desired shape can be formed by a single photolithography method. A pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered.
  • a wet film formation method such as a printing method or a coating method can also be used.
  • the transmittance it is desirable to make the transmittance larger than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ or less.
  • the film thickness depends on the material, it is usually selected in the range of 10 nm to 1000 nm, preferably 10 nm to 200 nm.
  • the cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium z copper mixture, magnesium Z silver mixture, magnesium Z aluminum mixture, magnesium Z indium mixture, aluminum Z acid aluminum -UM mixture, indium, lithium
  • a mixture of an electron injectable metal and a second metal which is a stable metal having a larger work function value than this, for example, magnesium Z Silver mixture, magnesium Z aluminum mixture, magnesium Z indium mixture, aluminum Z acid-aluminum (Al o) mixture, lithium
  • a 2 3 Z aluminum mixture, aluminum or the like is preferred.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as a cathode is several hundred ⁇ . ⁇ 5 m, preferably 50 nm to 200 nm.
  • the light emission luminance is advantageously improved.
  • a transparent or semi-transparent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the anode. It is possible to produce a device in which both cathodes are transparent.
  • the support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention, there is no particular limitation on the type of glass, plastic, etc., and it is transparent. Or opaque.
  • the supporting substrate is preferably transparent.
  • 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, cellose diacetate, cenorelose triacetate, cenorelose acetate butyrate, cenole mouth.
  • Cellulose esters such as cellulose acetate propionate (CAP), cellulose acetate phthalate (TAC), cellulose nitrate, or their derivatives, polysalt vinylidene, polybulualcohol, polyethylenebulual alcohol, syndiotactic pot Restyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide, polyethersulfone (PES), polyphenylene sulfide, polysulfones, polyetherimide, polyetherketoneimide, polyamide, fluorine resin, nylon, poly Examples thereof include methyl metatalylate, acrylic or polyarylates, Arton (trade name, manufactured by JSR) or Abel (trade name, manufactured by Mitsui Chemicals), and Tatsuma cycloolefin-based resin.
  • CAP cellulose acetate propionate
  • TAC cellulose acetate phthalate
  • cellulose nitrate or their derivatives, polysalt vinylidene
  • an inorganic film, an organic film, or a noble film of both may be formed on the surface of the resin film.
  • Water vapor permeability measured by a method in accordance with JIS K 7129-1992 (25 ⁇ 0.5 ° C, relative humidity (90 ⁇ 2)% RH) is preferably a rare film with 0.01 gZ (m 2 '24h) or less, and JIS K 7126-1987 Oxygen permeability measured by a method conforming to JIS No. 10 _3 mlZ (m 2 '24h'MPa) or less, and water vapor permeability is 10 _5 g / (m 2 ' 24h) or less.
  • any material may be used as long as it 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 may be used. it can.
  • the method for forming the barrier film is not particularly limited, for example, vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam, ion plating, plasma polymerization, atmospheric pressure Power capable of using a plasma polymerization method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, etc.
  • a method using an atmospheric pressure plasma polymerization method as described in JP-A No. 2004-68143 is particularly preferable. .
  • Examples of opaque support substrates include metal plates such as aluminum and stainless steel, and films. Examples thereof include a transparent resin substrate and a ceramic substrate.
  • the external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 5% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element.
  • a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts light emitted from an organic EL element into multiple colors using a phosphor may be used in combination.
  • the ⁇ max of light emission of the organic EL element is preferably 480 nm or less.
  • sealing means used in the present invention include a method of bonding a sealing member, an electrode, and a support substrate with an adhesive.
  • the sealing member may be a concave plate shape or a flat plate shape as long as it is disposed so as to cover the display region of the organic EL element. Further, transparency and electrical insulation are not particularly limited.
  • Specific examples include a glass plate, a polymer plate 'film, a metal plate' film, and the like.
  • the glass plate include soda-lime glass, norlium strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, norium borosilicate glass, and quartz.
  • the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
  • the metal plate include stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum power, and one or more metal or alloy power selected. .
  • a polymer film and a metal film can be preferably used because the device can be formed into a thin film.
  • the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 X 10 _3 mlZ (m 2 '24h'MPa) or less, and a method according to JIS K 7129-1992.
  • the measured water vapor transmission rate (25 ⁇ 0.5 ° C, relative humidity (90 ⁇ 2)% RH) is preferably less than l X 10 _3 gZ (m 2 '24h).
  • the sealing member is processed into a concave shape by sandblasting, chemical etching, or the like. Is called.
  • adhesives include photocuring and thermosetting adhesives having a reactive bur group of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. Can be mentioned.
  • heat- and chemical-curing type such as epoxy type can be mentioned.
  • hot-melt type polyamide, polyester, and polyolefin can be mentioned.
  • a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
  • the adhesive can be hardened up to a room temperature force of 80 ° C. Further, a desiccant may be dispersed in the adhesive. A commercially available dispenser may be used to apply the adhesive to the sealing part, or it may be printed like screen printing!
  • the electrode and the organic layer may be coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer may be formed in contact with the support substrate to form a sealing film.
  • the material for forming the film may be any material 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, etc. can be used.
  • the method for forming these films is not particularly limited, for example, vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma polymerization method.
  • Plasma CVD method, laser C VD method, thermal CVD method, coating method, etc. can be used.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil is used in the gas phase or liquid phase. It is preferable to inject. A vacuum is also possible. It is also possible to seal hygroscopic compounds inside.
  • Hygroscopic compounds include, for example, metal oxides (for example, acid sodium, acid potassium, acid calcium, barium oxide, magnesium oxide, acid aluminum, etc.), sulfate (For example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate, etc.), metal Halides (eg, calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, norium iodide, magnesium iodide, etc.), perchloric acids (eg, barium perchlorate, In particular, anhydrous salts are preferably used for sulfates, metal halides and perchloric acids.
  • metal oxides for example, acid sodium, acid potassium, acid calcium, barium oxide, magnesium oxide, acid aluminum, etc.
  • sulfate for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate, etc
  • 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. Therefore, it is preferable to provide such a protective film and a protective plate.
  • a material that can be used for this the same glass plate, polymer plate 'film, metal plate' film, etc. that are used for the sealing can be used. It is preferable to use a polymer film.
  • the organic EL element emits light inside the layer with a refractive index higher than that of air (refractive index is about 1.7 to 2.1), and only about 15% to 20% of the light generated in the light emitting layer can be extracted. It is generally said that there is nothing. This is because light incident on the interface (transparent substrate-air interface) at an angle ⁇ greater than the critical angle causes total reflection and cannot be extracted outside the device. This is because light undergoes total reflection with the substrate, the light is a transparent electrode, and is guided through the light emitting layer. As a result, the light escapes in the direction of the element side surface.
  • a method of introducing a flat layer having a refractive index Japanese Patent Laid-Open No. 2001-202827
  • a method of forming a diffraction grating between any one of the substrate, the transparent electrode layer and the light-emitting layer (including between the substrate and the outside world) (Kaihei 11-283751).
  • these methods can be used in combination with the organic EL device of the present invention.
  • a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter Alternatively, a method of forming a diffraction grating between any one of the substrate, the transparent electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
  • the present invention can obtain an element having further higher luminance or durability.
  • the low refractive index layer examples include air-mouthed gel, porous silica, magnesium fluoride, and fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less.
  • the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave exuded by evanescent enters the substrate.
  • the method of introducing a diffraction grating into an interface or any medium that causes total reflection has a feature that the effect of improving the light extraction efficiency is high.
  • This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction.
  • Light that cannot be emitted due to total internal reflection between layers is diffracted by introducing a diffraction grating into any layer or medium (inside the transparent substrate or transparent electrode). The person who tries to take out the outside.
  • the diffraction grating to be introduced preferably has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so a general one-dimensional diffraction grating having a periodic refractive index distribution only in one direction diffracts only light traveling in a specific direction. The light extraction efficiency does not increase so much. However, by making the refractive index distribution a two-dimensional distribution, the light traveling in all directions is diffracted and the light is captured. Dispensing efficiency increases.
  • the position where the diffraction grating is introduced may be in any of the layers or in the 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 about 1Z2 to about 3 times the wavelength of light in the medium.
  • the arrangement of the diffraction grating is preferably two-dimensionally repeated, such as a square lattice, a triangular lattice, or a honeycomb lattice.
  • the organic EL device of the present invention can be processed on a light extraction side of a substrate, for example, by providing a microlens array-like structure, or combined with a so-called condensing sheet, in a specific direction, for example, on the device light emitting surface.
  • a specific direction for example, on the device light emitting surface.
  • the brightness in a specific direction can be increased.
  • a quadrangular pyramid with a side of 30 ⁇ m and an apex angle of 90 degrees is arranged in two dimensions on the light extraction side of the substrate.
  • One side is 10 / z m ⁇ : LOO / z m is preferred. If it is smaller than this, the effect of diffraction is generated, and if the color is too large, the thickness becomes thick, which is not preferable.
  • the light condensing sheet for example, a sheet that has been put to practical use in an LED backlight of a liquid crystal display device can be used.
  • a brightness enhancement film (BEF) manufactured by Sumitomo 3EM may be used.
  • the shape of the prism sheet for example, the base material may be formed with stripes having a vertex angle of 90 degrees and a pitch of 50 111, a shape with rounded vertex angles, and a random pitch. It may be a changed shape or other shapes.
  • a light diffusing 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.
  • an anode / hole injection layer / hole transport layer, a Z light emitting layer, a Z electron transport layer, a Z electron injection layer, and a method for producing an organic EL device comprising a Z cathode To do As an example of the method for producing the organic EL device of the present invention, an anode / hole injection layer / hole transport layer, a Z light emitting layer, a Z electron transport layer, a Z electron injection layer, and a method for producing an organic EL device comprising a Z cathode To do.
  • a desired electrode material for example, a thin film having a material force for an anode is 1 ⁇ m or less, preferably ⁇ !
  • An anode is formed by a method such as vapor deposition or sputtering so that a film thickness of ⁇ 200 nm is obtained.
  • a method for forming each of these layers there are a vapor deposition method, a wet process (spin coating method, casting method, ink jet method, printing method) and the like as described above.
  • film formation by a coating method such as a spin coating method, an ink jet method, or a printing method is preferable.
  • the liquid medium for dissolving or dispersing the organic EL material according to the present invention includes, for example, ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, and halogenated carbonization such as dichlorobenzene.
  • Hydrogen, aromatic hydrocarbons such as toluene, xylene, mesitylene and cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin and dodecane, and organic solvents such as DMF and DMSO can be used.
  • a dispersion method it can disperse
  • a thin film that also has a material force for the cathode is formed on it by 1 ⁇ m or less, preferably by a method such as vapor deposition or sputtering so that the film thickness is in the range of 50 nm to 200 nm.
  • the production order can be reversed, and the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode can be produced in this order.
  • a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the anode as + and the cathode as one polarity.
  • An alternating voltage may be applied.
  • the AC waveform to be applied is arbitrary.
  • the organic EL element of the present invention can be used as a display device, a display, and various light sources.
  • lighting devices home lighting, interior lighting
  • watches Examples include, but are not limited to, 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. It can be effectively used as a backlight for liquid crystal display devices and as a light source for illumination.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like as needed during film formation.
  • a metal mask In the case of patterning, only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or in the production of an element that may be patterned on the entire layer, a conventionally known method Method can be used.
  • this ITO transparent electrode was provided.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • This transparent support group The plate is fixed to the substrate holder of a commercially available vacuum evaporation system, while 200 mg of ⁇ -NPD is placed in a molybdenum resistance heating boat, and 300 mg of F-1 is added as a fluorescent dopant in another molybdenum resistance heating boat. Put 200mg of Alq into a resistance heating boat made of molybdenum.
  • the heating boat containing Alq was energized and heated, and the deposition rate was 0. InmZ seconds.
  • An electron transport layer having a thickness of 30 nm was further deposited on the light emitting layer.
  • the substrate temperature during vapor deposition was room temperature.
  • lithium fluoride 0.5 nm and aluminum lOOnm were deposited to form a cathode, and an organic EL device OLED-1 having the constituent layers shown in FIG. 1 was produced.
  • FIG. 7 shows a schematic diagram of a lighting device, in which an organic EL element 101 is covered with a stainless steel sealing can 102 (note that the sealing operation with a stainless steel sealing can is performed by an organic EL element).
  • FIG. 8 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.
  • the stainless steel sealing can 102 is filled with nitrogen gas 108 and provided with a water catching agent 109 (using barium oxide as a dehydrating agent).
  • the light emitting characteristics of the organic EL device OLED-1 thus prepared were evaluated according to a conventional method.
  • DC current was applied to OLED-1, it started to emit light of about 4V, and the emission color was blue-green.
  • the voltage was adjusted to 2000 cdZm 2 and driven at a constant current while maintaining the current density at that time, the emission color changed to blue after about 250 hours.
  • the bull group of the light-emitting material F-1 undergoes radical polymerization when energized, and the network polymer of F-1 This is thought to be due to the disappearance of the vinyl group conjugation and the change in emission color from blue-green to blue.
  • an organic EL element OLED-2 was produced in the same manner as in the production of the element configuration shown in FIG.
  • the organic EL element OLED-3 was prepared in the same manner except that the element structure was vapor-deposited by a conventional method so as to have the element structure shown in FIG. Produced.
  • the luminescent color at that time was orange.
  • the organic EL element OLED-4 was prepared in the same manner except that the element structure was vapor-deposited by a conventional method so as to have the element structure shown in FIG. Produced.
  • the second layer is a red / green light emitting layer
  • the third layer is an intermediate layer
  • the fourth layer is an emission color compensation layer for changing the emission color from green to blue by energization
  • the fifth layer is The middle and sixth layers are blue light emitting layers.
  • the organic EL element OLED-4-2 which has a light-emitting color compensation layer (fourth layer) and no intermediate layer (fifth layer), was fabricated as a comparative element. Similarly, when the device was driven at a constant current with an initial luminance of 500 OcdZm 2 , the emission color had already changed to yellowish after about 100 hours.
  • the organic EL element OLED-4 provided with the emission color compensation layer was a good element with very little change in emission color over time.
  • the organic EL device OLED-4-3 was prepared by replacing the reactive light-emitting host H-1 of the organic EL device OLED-4 with m-Cp, and the emission lifetime was increased. It was compared with device O LED—4-2, and organic EL device OLED-4.
  • the organic EL element OLED-4 is 3180CdZm 2
  • the organic EL element OLED-4-2 is 1720cdZm 2
  • OL ED- 4 — 3 was 211 OcdZm 2 .
  • the polymer that emits blue light which is thought to be generated during current flow in the emission color compensation layer of the organic EL device OLED-4, is more robust and has a longer lifetime than the low-molecular dopant that originally existed. It was suggested that
  • the organic EL element OLED-4 3 using m-Cp with the same dopant configuration and no reactive group in the light-emitting host showed a remarkable light emission lifetime improvement effect similar to OLED-4. This indicates that it is effective to form a copolymer by coexisting a luminescent host capable of reacting with a reactive dopant in order to improve the luminescence lifetime.
  • an organic EL element OLED-5 was produced in the same manner as in the production of the element configuration shown in FIG.
  • the second layer is a red light-emitting layer
  • the third layer is an intermediate layer
  • the fourth layer is a light-emitting color compensation layer for changing the color to orange, green, and blue when energized
  • the fifth layer is The intermediate layer and the sixth layer are blue light emitting layers.
  • the light emission lifetime is even better than that of the organic EL element OLED-4 of Example 4, and the light emission luminance after constant driving at an initial luminance of 5000 cd / m 2 for 300 hours is 3450 cd / m 2 . To one.
  • the light emitting host and the light emitting color compensation layer of the organic EL element OLED-6 are changed from H-2 to H-6, and the emission dopant (dopant whose emission color changes) is changed from P-9 to P-7.
  • the same light emission color compensation effect was confirmed for the device (OLED-6-2) that was changed to.

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Un élément électroluminescent organique est doté d'au moins une anode et une cathode sur un substrat de support, et d'une couche de composé organique comprenant au moins une couche d'émission de lumière entre l'anode et la cathode. Au moins une couche de composé organique contient un matériau émetteur de lumière dont le spectre d'émission se décale vers un côté de courte longueur d'onde lorsque de l'électricité est acheminée. Un dispositif d'affichage et un dispositif d'éclairage utilisant un tel élément sont également présentés.
PCT/JP2007/055507 2006-03-22 2007-03-19 Élément électroluminescent organique, procédé de stabilisation de la chromaticité d'émission de l'élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage électronique WO2007119420A1 (fr)

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WO2009157477A1 (fr) * 2008-06-26 2009-12-30 コニカミノルタホールディングス株式会社 Procédé de fabrication d’un élément électroluminescent organique et élément électroluminescent organique émettant de la lumière blanche
JP2011508732A (ja) * 2007-12-20 2011-03-17 ジョージア・テック・リサーチ・コーポレーション カルバゾールをベースとする正孔輸送材料および／または電子ブロッキング材料および／またはホストポリマー材料
JP2013245179A (ja) * 2012-05-25 2013-12-09 Konica Minolta Inc 金属錯体、有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2016048796A (ja) * 2015-11-16 2016-04-07 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、それが具備された表示装置及び照明装置
JP2017120795A (ja) * 2010-01-20 2017-07-06 ユニバーサル ディスプレイ コーポレイション 照明用途のためのエレクトロルミネッセンスデバイス
WO2018095395A1 (fr) * 2016-11-23 2018-05-31 广州华睿光电材料有限公司 Haut polymère, mélange le contenant, composition, composant électronique organique, et monomère pour polymérisation

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JP2011508732A (ja) * 2007-12-20 2011-03-17 ジョージア・テック・リサーチ・コーポレーション カルバゾールをベースとする正孔輸送材料および／または電子ブロッキング材料および／またはホストポリマー材料
WO2009157477A1 (fr) * 2008-06-26 2009-12-30 コニカミノルタホールディングス株式会社 Procédé de fabrication d’un élément électroluminescent organique et élément électroluminescent organique émettant de la lumière blanche
JPWO2009157477A1 (ja) * 2008-06-26 2011-12-15 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子の製造方法及び白色発光有機エレクトロルミネッセンス素子
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JP2013245179A (ja) * 2012-05-25 2013-12-09 Konica Minolta Inc 金属錯体、有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2016048796A (ja) * 2015-11-16 2016-04-07 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、それが具備された表示装置及び照明装置
WO2018095395A1 (fr) * 2016-11-23 2018-05-31 广州华睿光电材料有限公司 Haut polymère, mélange le contenant, composition, composant électronique organique, et monomère pour polymérisation
CN109791992A (zh) * 2016-11-23 2019-05-21 广州华睿光电材料有限公司 高聚物、包含其的混合物、组合物和有机电子器件以及用于聚合的单体
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