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WO2015118650A1 - Élément électroluminescent organique, dispositif de source lumineuse, liquide de revêtement, et procédé de production d'un élément électroluminescent organique - Google Patents

Élément électroluminescent organique, dispositif de source lumineuse, liquide de revêtement, et procédé de production d'un élément électroluminescent organique Download PDF

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Publication number
WO2015118650A1
WO2015118650A1 PCT/JP2014/052830 JP2014052830W WO2015118650A1 WO 2015118650 A1 WO2015118650 A1 WO 2015118650A1 JP 2014052830 W JP2014052830 W JP 2014052830W WO 2015118650 A1 WO2015118650 A1 WO 2015118650A1
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light emitting
dopant
organic light
emitting device
organic
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Japanese (ja)
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正樹 松森
荒谷　介和
広貴 佐久間
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Hitachi Ltd
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    • 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
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Definitions

  • the present invention relates to an organic light emitting device, a light source device, a coating liquid, and a method of manufacturing an organic light emitting device.
  • Patent Document 1 proposes the following technology.
  • Patent Document 1 discloses an organic electroluminescent device in which a light emitting layer of an organic electroluminescent device is formed by a dry process in vacuum, and organic compound molecules constituting the light emitting layer are aligned parallel to a plane direction of the light emitting layer. It is an element.
  • Patent Document 2 discloses a technique of uniaxially orienting a light emitting layer by light orientation and extracting polarized light.
  • Patent Document 3 discloses a technique for orienting dopant molecules using surface energy.
  • the conventional orientation control method of the dopant molecule utilizes the anisotropy of the molecular shape, the ordering property of the orientation is not sufficient, and it is difficult to orient the dopant molecule other than flat plate or rod shape. There is a problem that
  • An object of the present invention is to provide an organic light emitting device, a light source device, and a method of manufacturing the organic light emitting device, in which highly efficient light emission can be obtained, in which the alignment order of the dopant molecules is enhanced.
  • the organic light emitting device is an organic light emitting device having an upper electrode, a lower electrode, and a light emitting layer disposed between the upper electrode and the lower electrode, and the first light emitting layer is a first light emitting layer.
  • the first dopant is a metal complex having a photoisomerization site, and the horizontal component of the average value of the light emission transition moment with respect to the substrate surface is larger than the vertical component for the first dopant.
  • an organic light emitting device it is possible to obtain an organic light emitting device, a light source device, and a method of manufacturing an organic light emitting device, in which highly efficient light emission can be obtained by enhancing the alignment order of the dopant molecules.
  • Organic light-emitting devices are promising technologies as displays, light sources, and lighting devices, and for their practical use, improvement of luminous efficiency for reduction of power consumption, extension of life for reliability assurance, cost reduction It is hoped that the development of yield improvement and simplified process technology towards
  • the luminous efficiency is represented by the external quantum efficiency ( ⁇ ext ).
  • the external quantum efficiency is the percentage (%) of photons generated with respect to the number of electrons injected from the outside into the device, and is expressed by the following equation (1).
  • ⁇ ext ⁇ PL out out (1)
  • ⁇ carrier balance factor of holes and electrons
  • ⁇ generation probability of the excited state contributing to light emission
  • ⁇ PL emission quantum efficiency from the excited state
  • out light extraction efficiency out of the device .
  • the organic light emitting device In the organic light emitting device, light emitted from the dopant whose orientation is not controlled is in a three-dimensional random direction, and light having a total reflection angle or more is generated at a certain ratio, which lowers the luminous efficiency.
  • the present invention by controlling the orientation of the dopant, it is possible to distribute the light emission direction from the dopant to the substrate surface side, and it is effective to improve the luminous efficiency of the organic light emitting device.
  • the light emitting molecules to be dopants have light emission transition moments determined by their molecular shapes and electron configurations of the excited state and the ground state. Since the direction of light emission is a direction perpendicular to the direction of the light emission transition moment, by orienting the dopant so that the direction of the light emission transition moment is parallel to the surface of the thin plate, total reflection at the interface is achieved. The light confinement effect can be avoided, and the light emission efficiency can be improved.
  • the molecular shape of the dopant is rod-like or flat, and the molecule is oriented by utilizing the intermolecular interaction and the excluded volume effect.
  • the conventional molecular orientation has a problem that it is difficult to increase the order of orientation.
  • the dopant having a photoisomerization site according to the present invention can be oriented by light, it is possible to enhance the order of orientation and there is also no concentration dependency of the dopant, so that it can be adjusted according to the concentration at which the luminous efficiency is high. It is also possible to make an organic light emitting device at a low concentration by adding a host material to the above, and it works effectively to improve the light emission efficiency.
  • Phosphorescent dopants capable of greatly improving ⁇ are usually metal complexes in which about four ligands are coordinated to a transition metal, or steric materials having a twist structure, and the molecular shape is nearly spherical. , It can not be oriented by the conventional method.
  • the dopant having a photoisomerization site according to the present invention is oriented by light, it is possible to orient a highly efficient luminescent dopant such as a phosphorescent dopant which is not flat or rod-like in molecular shape, and is effective for improving the luminous efficiency Act on.
  • Azobenzene and stilbene cause a trans-cis photoisomerization reaction by irradiating light.
  • azobenzene and stilbene have an absorption axis in the long axis direction of the molecule. If the azobenzene and stilbene are continuously irradiated with collimated light, cis-trans photoisomerization is repeated, and eventually the long axis direction of the molecule becomes parallel to the traveling direction of the collimated light.
  • the photoisomerization site can not absorb any more light, and the orientation is fixed in that direction.
  • the direction of the light emission transition moment of the dopant can be oriented parallel to the substrate surface, and from the dopant Since the light emission direction can be aligned with the substrate surface side, the light emission efficiency can be improved.
  • the horizontal component with respect to the substrate surface may be larger than the vertical component when the average value of the emission transition moment of the dopant is taken.
  • the light irradiation for photoalignment according to the present invention works effectively during or after the formation of the light emitting layer.
  • the dopant tends to move more easily before drying in which the dopant and the solvent coexist, and it effectively functions to improve the degree of orientational order.
  • Patent Document 2 discloses a technique for uniaxially orienting the light emitting layer by light orientation and extracting polarized light, but the organic light emitting element according to the present invention does not emit polarized light.
  • FIG. 1 is a cross-sectional view of an embodiment of a light source device according to the present invention.
  • FIG. 1 shows a top emission type light source device for extracting light from the upper electrode 102 side.
  • the lower electrode 101, the first bank 104, the second bank 105, the organic layer 103, the upper electrode 102, the resin layer 106, the sealing substrate 107, and the light extraction layer 108 are in this order on the substrate 100. It is arranged.
  • the organic light emitting element has an upper electrode 102, a lower electrode 101 and an organic layer 103.
  • the lower electrode 101 is an anode.
  • the lower electrode 101 may be used as a cathode.
  • the lower electrode 101 is formed by patterning, for example, by photolithography.
  • the upper electrode 102 When the lower electrode 101 is an anode, the upper electrode 102 is a cathode. When the lower electrode 101 is a cathode, the upper electrode 102 is an anode.
  • the upper electrode 102 when the upper electrode 102 is ITO or IZO, when forming ITO or IZO by a sputtering method, a buffer layer may be provided between the organic layer 103 and the upper electrode 102 in order to reduce damage due to sputtering.
  • a metal oxide such as molybdenum oxide or vanadium oxide is used.
  • the upper electrode 102 is connected to the lower electrode 101 of the adjacent light emitting unit. Thereby, the light emitting units can be connected in series.
  • the first bank 104 formed on the side of the organic light emitting element is forward tapered, covers the end of the patterned lower electrode 101, and prevents partial short circuit failure of the light emitting portion.
  • development exposure is performed using a predetermined photomask to form a first bank 104.
  • the surface of the first bank 104 on the side where the organic layer 103 is present may be subjected to water repellent treatment.
  • the surface of the first bank 104 is plasma-treated with a fluorine-based gas, and the surface of the first bank 104 is fluorinated to perform water repellency treatment.
  • a water repellent layer is formed on the surface of the first bank 104.
  • photosensitive polyimide is preferable.
  • an acrylic resin, a novolak resin, a phenol resin, a non-photosensitive material, or the like can be used as the first bank 104.
  • the second bank 105 is formed on the first bank 104.
  • the second bank 105 is reversely tapered and is used to prevent the upper electrodes 102 of the adjacent light emitting portions from conducting.
  • the second bank 105 is formed by performing development exposure using a predetermined photomask.
  • the surface of the second bank 105 on the side where the organic layer 103 is present may be subjected to water repellency treatment.
  • the surface of the second bank 105 is plasma-treated with a fluorine-based gas, and the surface of the second bank 105 is fluorinated to perform water repellency treatment.
  • a water repellent layer is formed on the surface of the second bank 105.
  • an acrylic resin, a novolak resin, a phenol resin, a non-photosensitive material, or the like can be used.
  • the resin layer 106 is formed on the upper electrode 102 and the second bank 105.
  • the resin layer 106 is used to seal the light emitting portion and to prevent the entry of gas or moisture which causes deterioration of the organic light emitting element.
  • various polymers such as epoxy resin can be used.
  • an inorganic passivation film on the upper electrode 102 can also be used as the resin layer 106.
  • the sealing substrate 107 is formed on the resin layer 106.
  • the sealing substrate 107 is a glass substrate. However, other than the glass substrate, a plastic substrate having an appropriate gas barrier film can also be used.
  • the light extraction layer 108 is formed on the sealing substrate 107.
  • the light extraction layer 108 is used to efficiently extract the light emitted from the organic layer 103.
  • a structure such as a microlens, or a film having scattering property and diffuse reflection property is used.
  • the organic light emitting element used here may be a single element or an element divided into a plurality.
  • a method of connecting a plurality of elements a method in which each element is connected in series, in parallel or in combination is mentioned.
  • the organic light emitting element is divided into a plurality of parts, the following modes can be considered.
  • the first dopant, the second dopant and the third dopant will be described later.
  • (1) There exist a plurality of single organic light emitting elements including the first dopant, the second dopant and the third dopant.
  • FIG. 2 is a cross-sectional view of one embodiment of the organic light emitting device in the present invention.
  • the organic layer 103 may have a single layer structure of only the light emitting layer 303 or a multilayer structure including any one or more of the electron injection layer 305, the electron transport layer 304, the hole transport layer 302 and the hole injection layer 301.
  • the electron injection layer 305 and the electron transport layer 304, the electron transport layer 304 and the light emitting layer 303, the light emitting layer 303 and the hole transport layer 302, the hole transport layer 302 and the hole injection layer 301 may be in contact with each other.
  • the other layers described above may be interposed between
  • the light emitting layer 303 includes a host molecule (hereinafter referred to as a host) and a dopant molecule (hereinafter referred to as a dopant).
  • the organic light emitting element in FIG. 1 is provided with a drive circuit, a housing, and the like to form a light source device.
  • FIG. 3 is a perspective view of an embodiment of a light source device according to the present invention.
  • the first organic light emitting element 202 and the second organic light emitting element 203 are divided by a second bank 105.
  • a diffusion plate 201 is disposed in the direction in which light is extracted from the first organic light emitting element 202 and the second organic light emitting element 203.
  • the first organic light emitting element 202 is an organic light emitting element containing a red dopant and a green dopant
  • the second organic light emitting element 203 contains a blue dopant.
  • the first organic light emitting element 202 and the second organic light emitting element 203 include an organic light emitting element containing a red dopant, an organic light emitting element containing a green dopant, and a blue dopant. It becomes any of the organic light emitting element containing.
  • the arrangement of the organic light emitting elements may be a zigzag as well as a stripe as shown in FIG.
  • the organic light emitting device When the organic light emitting device is manufactured by coating, it can be easily manufactured by arranging the organic light emitting device in a stripe as shown in FIG.
  • a diffuser plate 201 may be attached to the top of the light extraction surface of the organic light emitting element as shown in FIG. 3 in order to obtain good white light.
  • the diffusion plate 201 one in which a scatterer is dispersed in resin or glass, one in which a concavo-convex structure is formed on the surface, and the like can be considered.
  • the blue dopant has a maximum intensity of PL spectrum at room temperature (25 ° C.) between 400 nm and 500 nm.
  • the green dopant has a maximum intensity of PL spectrum at room temperature between 500 nm and 590 nm.
  • the red dopant has a maximum intensity of PL spectrum at room temperature between 590 nm and 780 nm.
  • the luminescent dopant according to the present invention is characterized by having a photoisomerization site.
  • the photoisomerization site is an azobenzene group or a stilbene group, and the azobenzene group is more preferable because the azobenzene group is efficiently oriented at a low irradiation amount.
  • the structure is preferably a metal complex represented by the following general formula (1).
  • M is a metal element
  • X1-L1-X2 and X1-L2-X2 each independently represent a bidentate ligand
  • X1 and X2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom
  • L1 represents an atomic group forming a bidentate ligand with X1 and X2
  • L2 represents an atomic group containing a photoisomerization site and forming a bidentate ligand with X1 and X2.
  • n represents an integer of 1 or more.
  • the central metal M is preferably a transition metal, more preferably an element of groups 8, 9 and 10 of the periodic table, and still more preferably Ni, Pd, Pt, Au, Ag, Rh, Ir .
  • L1 in the general formula (1) is a fused polycyclic aromatic derivative such as benzoquinoline, phenanthroline, acetylacetonate derivative, picolinate derivative, tetrakis pyrazolyl borate derivative or the like, or a compound represented by the general formula (2).
  • Examples of the aromatic heterocycle represented by Y 1 include quinoline ring, isoquinoline ring, pyridine ring, quinoxaline ring, thiazole ring, pyrazole ring, pyrimidine ring, benzothiazole ring, oxazole ring, benzoxazole ring, indole ring, isoindole ring, etc. Can be mentioned.
  • Examples of the aromatic hydrocarbon ring or aromatic heterocycle represented by Y 2 include, in addition to the aromatic heterocycle in Y 1, a benzene ring, a naphthalene ring, an anthracene ring, an thiophene ring, a benzothiophene ring, a furan ring and a benzofuran ring, Examples thereof include a fluorene ring and a benzopyran ring. Substituents other than functional groups may be added to the aromatic heterocycle or the aromatic hydrocarbon ring.
  • the substituent is, for example, an alkyl group (methyl group, ethyl group), a substituted alkyl group (trifluoromethyl group), an alkoxy group (methoxy group), a halogen atom (fluorine, chlorine), an amino group, a phenyl group or the like.
  • L2 in the general formula (1) is one in which a photoisomerization site is introduced into the structure shown in L1.
  • a dopant represented by the following general formula (101) can be used as the light emitting dopant according to the present invention.
  • R 1 to R 6 each independently represent a hydrogen atom, a cyano group, a derivative of a carbazoyl group represented by the following general formula (102), or a hydrocarbon group containing a photoisomerization site, and at least one cyano group As described above, it contains at least two or more carbazoyl group derivatives represented by the general formula (102), and at least one or more hydrocarbon group containing a photoisomerization site.
  • R 11 and R 12 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group.
  • the dopant molecule represented by the general formula (101) has a twisted structure with respect to the central benzene ring due to steric hindrance because the density of the carbazoyl group is high, and the carbazoyl of the central benzene ring and the carbazoyl group derivative is The base planes are not coplanar. That is, the three-dimensional structure of the dopant molecule represented by the general formula (101) is not flat, and the orientation method by the molecular shape can not be used. In the present invention, the molecules can be oriented by light irradiation, which effectively functions to improve the light extraction efficiency.
  • the wavelength of the collimated light to be irradiated is preferably light of a wavelength longer than 280 nm, more preferably light of 300 nm or more, and still more preferably light of 340 nm or more.
  • the solid concentration of the blue dopant is desirably 10 wt% or more and 30 wt% or less, the solid concentration of the green dopant is desirably less than 10 wt%, and the solid concentration of the red dopant is desirably less than 10 wt%.
  • the weight average molecular weight of the light emitting dopant is preferably 500 or more and 3,000 or less.
  • the molecules of the phosphorescent dopant there are molecules of various shapes which are not tabular or rod-like, such as regular tetrahedron, regular octahedron, and sphere.
  • the molecules can be oriented in any direction. By orienting the molecules, the orientation of the transition dipole moment is controlled to be parallel to the substrate plane.
  • dopant molecules of each color are used in combination with dopant molecules oriented by utilizing surface energy as described in Patent Document 3 in addition to the dopants oriented by the above-described photoalignment.
  • Each can be oriented on different principles.
  • the orientation state of the organic molecule can be investigated by measuring an IR spectrum or a Raman spectrum while changing the incident angle.
  • the direction of the transition dipole moment can also be evaluated by known methods. For example (APPLIED PHYSICS LETTERS 96, 073302 (2010).), The radiation angle dependence of the P-polarization component of photoluminescence is measured using the hemispherical lens / cylindrical lens that is in optical contact with the organic light emitting device, By excluding it and measuring it experimentally and comparing with computer simulation, the ratio of each of the horizontal component and the vertical component in the transition dipole moment can be determined. This is because the angular dependence of the P polarization intensity is determined by the ratio of the horizontal component to the vertical component (S polarization consists of only the horizontal component).
  • the orientation of the organic molecules constituting the ordinary light emitting layer is random (isotropic), so that the proportion of components of the transition dipole moment is 50% for both horizontal and vertical components.
  • ⁇ Host> It is preferable to use a carbazole derivative, a fluorene derivative or an arylsilane derivative as a host. In order to obtain efficient light emission, it is preferable that the excitation energy of the host be sufficiently larger than the excitation energy of the blue dopant. The excitation energy is measured using an emission spectrum.
  • Hole injection layer> The hole injection layer 301 is used for the purpose of improving the luminous efficiency and the lifetime. Further, although not particularly essential, it is used for the purpose of alleviating the irregularities of the anode.
  • the hole injection layer 301 may be provided as a single layer or a plurality of layers.
  • the hole injection layer 301 is preferably a conductive polymer such as PEDOT (poly (3,4-ethylenedioxythiophene)): PSS (polystyrene sulfonate).
  • PEDOT poly (3,4-ethylenedioxythiophene)
  • PSS polystyrene sulfonate
  • polypyrrole-based and triphenylamine-based polymer materials can be used.
  • phthalocyanine compounds and starburst amine compounds which are often used in combination with a low molecular weight (weight average molecular weight of 10000 or less) material system are also applicable.
  • the hole transport layer 302 is made of a material having a function of transporting holes, and the hole injection layer 301 and the electron blocking layer are also included in the hole transport layer 302 in a broad sense.
  • the hole transport layer 302 may be provided as a single layer or a plurality of layers.
  • the electron transport layer 304 is a layer that supplies electrons to the light emitting layer 303.
  • the electron injection layer 305 and the hole blocking layer are also included in the electron transport layer 304 in a broad sense.
  • the electron transporting layer 304 may be provided as a single layer or a plurality of layers. Examples of the material of the electron transport layer 304 include bis (2-methyl-8-quinolinolato) -4- (phenylphenolato) aluminum (hereinafter, BAlq), and tris (8-quinolinolato) aluminum (hereinafter, Alq3).
  • the electron injection layer 305 improves the electron injection efficiency from the cathode to the electron transport layer 304. Specifically, lithium fluoride, magnesium fluoride, calcium fluoride, strontium fluoride, barium fluoride, magnesium oxide and aluminum oxide are desirable.
  • the substrate 100 include a glass substrate, a metal substrate, and a plastic substrate on which an inorganic material such as SiO 2, SiN x, or Al 2 O 3 is formed.
  • metal substrate materials include alloys such as stainless steel and 42 alloy.
  • plastic substrate materials include polyethylene terephthalate, polyethylene naphthalate, polymethyl methacrylate, polysulfone, polycarbonate, polyimide and the like.
  • anode material any material having transparency and a high work function can be used.
  • the cathode material is a reflective electrode for reflecting the light from the light emitting layer 303.
  • a laminate of LiF and Al, an Mg: Ag alloy, or the like is preferably used.
  • a Cs compound, a Ba compound, a Ca compound etc. can be used instead of LiF.
  • the coating solution is obtained by dissolving the material forming the light emitting layer 303 in a suitable solvent. In the following description, a case where a host, a red dopant, a green dopant, and a blue dopant are included as materials for forming the light emitting layer 303 will be described.
  • the solvent to be used here may be, for example, an aromatic hydrocarbon solvent such as toluene, an ether solvent such as tetrahydrofuran, an alcohol, a solvent such as a fluorine solvent and the like, and the like.
  • a mixed solvent in which a plurality of the above-mentioned solvents are mixed may be used to adjust the solubility of each material and the drying rate.
  • two kinds of solvents having different boiling points (a first solvent and a second solvent) are prepared, and a second solvent having a high boiling point is a good solvent for a green or blue dopant, and a green dopant or a blue dopant is obtained. Transfer to the surface of the membrane.
  • the solubility of the solvent is measured by liquid chromatography.
  • the light emitting layer 303 can be formed by a dry method such as a vacuum deposition method as a film forming method, a spin coating method, a casting method, a dip coating method, a spray coating method, a screen printing method, an inkjet printing method, a wet method (coating method).
  • a dry method such as a vacuum deposition method as a film forming method, a spin coating method, a casting method, a dip coating method, a spray coating method, a screen printing method, an inkjet printing method, a wet method (coating method).
  • a die coat method, a gravure coat method, a bar coat method etc. can be mentioned.
  • the light emitting layer 303 is formed using one of these methods.
  • the coating method has advantages such as easy film formation with a large area and high utilization efficiency of materials as compared with the dry method.
  • a white light emitting device having a structure shown in FIG. 3 was produced as a first embodiment of the present invention.
  • An ITO electrode was formed on the lower electrode 101, and PEDOT was formed on the hole injection layer by spin coating.
  • a polymer-based material was used for the hole transport layer.
  • the organic light emitting layer is mCP (1, 3-bis (carbazol-9-yl) benzene) as a host, (Chem. 3) for blue dopant, (Chem. 5) for red dopant, and (Chem. 8) for green dopant Using.
  • the weight ratio of each material was 100: 10: 0.5: 0.5.
  • These hosts, blue, red and green dopants were dissolved in toluene to prepare a coating solution. After spin coating using this coating solution, heating is performed while irradiating collimated light extracted from a 2 kW high-pressure mercury lamp so that the luminescence transition moment of each color dopant becomes parallel to the substrate surface, forming an organic luminescence reaction. did.
  • the irradiation light amount was 1.5 J / cm 2 .
  • Example 1 When voltage was applied to the produced organic light emitting device, light emission from three dopants was confirmed from the EL spectrum, and white light emission was confirmed. Moreover, when forming an organic light emitting layer as Comparative Example 1, an element was manufactured without irradiating collimated light. Example 1 exhibited a luminous efficiency 1.9 times higher than that of Comparative Example 1. In the photoluminescence measurement of the light emitting layer of Example 1, the angle dependency of P polarized light intensity was measured, and the ratio of the component of transition dipole moment of each color dopant was examined. The horizontal component was 85% or more for each color. Met. On the other hand, in Comparative Example 1, the horizontal component was about 50% for each color.
  • a light source device in which a plurality of organic light emitting elements were connected was manufactured.
  • the fabricated device has the same layer configuration as in Example 1, and as a light emitting layer, Ir (piq) 3 (tris (1-phenylisoquinoline) iridium (III)) as a host and a red dopant, and (Formula 7) as a green dopant
  • Ir (piq) 3 tris (1-phenylisoquinoline) iridium (III)
  • Ir (piq) 3 tris (1-phenylisoquinoline) iridium (III)
  • (Formula 7) as a green dopant
  • An element (RG element) including the element (RG element) and the light emitting layer (B element) including the host and the blue dopant as chemical compound 3 was separately formed in the plane, and the elements were connected in series and in parallel.
  • Example 2 In order to obtain homogeneous white light, a diffusion plate was attached to the light emitting surface of the fabricated device. Good white light was obtained with the manufactured light source device. Moreover, when forming an organic light emitting layer as Comparative Example 2, an element was manufactured without irradiating collimated light. Example 2 exhibited a luminous efficiency 1.8 times higher than that of Comparative Example 2. In the photoluminescence measurement of the light emitting layer of Example 2, the angle dependency of P polarized light intensity was measured, and the ratio of the component of the transition dipole moment of each color dopant was examined. It was 85% or more and about 50% for red. On the other hand, in Comparative Example 2, the horizontal component was about 50% for each color.
  • a light source device in which a plurality of organic light emitting elements were connected was manufactured.
  • the fabricated device has the same layer configuration as in Example 1 and includes a device (R element 106) as a host and a red dopant in the light emitting layer (R element), and a light emitting layer as a host material and a green dopant (Chem. 105)
  • An element (G element) containing a host and a blue dopant (B element) was separately formed in a plane in the element (G element) containing and the light emitting layer, and the elements were connected in series and in parallel.
  • the coating film was formed by coating using an inkjet method, and light was irradiated in the same manner as in Example 1 to orient the dopant.
  • the light emission position was made to be around 75 nm from the upper electrode for each color dopant.
  • Example 3 In order to obtain homogeneous white light, a diffusion plate was attached to the light emitting surface of the fabricated device. Good white light was obtained with the manufactured light source device. Moreover, when forming an organic light emitting layer as Comparative Example 3, an element was manufactured without irradiating collimated light. Example 3 exhibited a luminous efficiency 2.1 times higher than that of Comparative Example 3. In the photoluminescence measurement of the light emitting layer of Example 3, the angle dependency of P polarized light intensity was measured, and the ratio of the component of transition dipole moment of each color dopant was examined. The horizontal component was 85% or more for each color. Met. On the other hand, in Comparative Example 2, the horizontal component was about 50% for each color.
  • the light source device shown in FIG. 4 was manufactured as an example of the present invention.
  • the organic light emitting element which is a component of the light source device comprises the same substrate 100, lower electrode 101, organic layer 103 and upper electrode 102 as in the first embodiment.
  • the organic light emitting element is sealed with a sealing tube glass 501 with a desiccant so that the organic layer 103 is shielded from the open air.
  • the lower electrode 101 and the upper electrode 102 are each connected to the drive circuit 503 through a wire 502.
  • the organic light emitting element with the sealing tube glass 501 and the drive circuit 503 are covered by the casing 505 to be a light source device 506 as a whole.
  • the drive circuit 503 lights up by being connected to an external power supply through the plug 504.
  • the light source device A using the organic light emitting element of Example 1 and the light source device B using the organic light emitting element of Comparative Example 1 were manufactured, the light source device A consumes 41% less power than the light source device B. done.
  • An organic light-emitting device was produced in the same manner as in Example 1, except that in Example 1, the blue dopant was (Chemical Formula 16), the red dopant was (Chemical Formula 17), and the green dopant was (Chemical Formula 7).
  • Example 5 When voltage was applied to the produced organic light emitting device, light emission from three dopants was confirmed from the EL spectrum, and white light emission was confirmed. Moreover, when forming an organic light emitting layer as Comparative Example 5, an element was manufactured without irradiating collimated light. Example 5 showed a 1.3 times higher luminous efficiency than Comparative Example 5. In the photoluminescence measurement of the light emitting layer of Example 1, the angle dependency of P polarized light intensity was measured, and the ratio of the component of transition dipole moment of each color dopant was examined. The horizontal component was 85% or more for each color. Met. On the other hand, the blue dopant and the red dopant in Comparative Example 5 had a horizontal component of 85% or more, but about 50% in the green dopant.
  • Example 1 when taking collimated light from a 2 kW high pressure mercury lamp, an organic light emitting element A prepared by cutting light having a wavelength shorter than 280 nm using a sharp cut filter, light having a wavelength shorter than 300 nm
  • the organic light-emitting element B was prepared by cutting and irradiating light
  • the organic light-emitting element C was prepared by cutting and irradiating light having a wavelength shorter than 340 nm.
  • these three types of organic light emitting elements were compared with the organic light emitting element of Comparative Example 1, they exhibited luminous efficiencies 2.0 times, 2.1 times, and 2.3 times higher, respectively.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'objet de la présente invention est de fournir : un élément électroluminescent organique qui présente un agencement ordonné accru de l'orientation de molécules de dopant et qui obtient une émission de lumière à haut rendement ; un dispositif de source lumineuse ; et un procédé de fabrication d'un élément électroluminescent organique. L'élément électroluminescent organique possède une électrode supérieure, une électrode inférieure et une couche électroluminescente disposée entre l'électrode supérieure et l'électrode inférieure. Un premier dopant est contenu dans la couche électroluminescente ; le premier dopant comprend un complexe métallique ayant un site de photo-isomérisation ; et la composante horizontale de la valeur moyenne du moment de transition radiative du premier dopant par rapport à la surface du substrat est supérieure à la composante verticale.
PCT/JP2014/052830 2014-02-07 2014-02-07 Élément électroluminescent organique, dispositif de source lumineuse, liquide de revêtement, et procédé de production d'un élément électroluminescent organique Ceased WO2015118650A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018210018A1 (fr) * 2017-05-17 2018-11-22 京东方科技集团股份有限公司 Substrat d'écran oled et son procédé de fabrication, dispositif d'affichage et son procédé d'encapsulation
CN112366221A (zh) * 2020-11-10 2021-02-12 京东方科技集团股份有限公司 显示面板及其制备方法、显示装置
WO2022178593A1 (fr) * 2021-02-26 2022-09-01 University Of Tasmania Dérivés de porphyrine et leurs utilisations

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11102783A (ja) * 1997-09-26 1999-04-13 Mitsubishi Electric Corp 有機エレクトロルミネッセンス素子およびその製造方法
JP2003163087A (ja) * 2001-11-28 2003-06-06 Nec Corp 有機エレクトロルミネッセンス素子
JP2012231134A (ja) * 2011-04-12 2012-11-22 Fujifilm Corp 有機電界発光素子、有機電界発光素子用材料、膜、発光層、及び有機電界発光素子の作製方法
JP2013518296A (ja) * 2010-01-22 2013-05-20 エルジー・ケム・リミテッド 光配向膜配向処理用粘着フィルム

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11102783A (ja) * 1997-09-26 1999-04-13 Mitsubishi Electric Corp 有機エレクトロルミネッセンス素子およびその製造方法
JP2003163087A (ja) * 2001-11-28 2003-06-06 Nec Corp 有機エレクトロルミネッセンス素子
JP2013518296A (ja) * 2010-01-22 2013-05-20 エルジー・ケム・リミテッド 光配向膜配向処理用粘着フィルム
JP2012231134A (ja) * 2011-04-12 2012-11-22 Fujifilm Corp 有機電界発光素子、有機電界発光素子用材料、膜、発光層、及び有機電界発光素子の作製方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
THOMAS KOEPPLMAYR ET AL.: "Patterned Immobilization of a Luminescent Ru(II) Complex in Polymer Films Using the Photoreaction of Benzyl thiocyanate: Toward Color Emission Tuning of Electroluminescent Devices", MACROMOLECULAR CHEMISTRY AND PHYSICS, vol. 213, no. Issue 4, pages 367 - 373, XP055219402 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018210018A1 (fr) * 2017-05-17 2018-11-22 京东方科技集团股份有限公司 Substrat d'écran oled et son procédé de fabrication, dispositif d'affichage et son procédé d'encapsulation
US11121337B2 (en) 2017-05-17 2021-09-14 Boe Technology Group Co., Ltd. OLED display substrate and method for manufacturing the same, display device and packaging method thereof
CN112366221A (zh) * 2020-11-10 2021-02-12 京东方科技集团股份有限公司 显示面板及其制备方法、显示装置
CN112366221B (zh) * 2020-11-10 2024-05-24 京东方科技集团股份有限公司 显示面板及其制备方法、显示装置
WO2022178593A1 (fr) * 2021-02-26 2022-09-01 University Of Tasmania Dérivés de porphyrine et leurs utilisations

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