WO2012133644A1 - Élément électroluminescent organique, dispositif émetteur de lumière, dispositif d'affichage et dispositif d'éclairage utilisant un élément électroluminescent organique, et composé pour élément électroluminescent organique - Google Patents

Élément électroluminescent organique, dispositif émetteur de lumière, dispositif d'affichage et dispositif d'éclairage utilisant un élément électroluminescent organique, et composé pour élément électroluminescent organique Download PDF

Info

Publication number
WO2012133644A1
WO2012133644A1 PCT/JP2012/058350 JP2012058350W WO2012133644A1 WO 2012133644 A1 WO2012133644 A1 WO 2012133644A1 JP 2012058350 W JP2012058350 W JP 2012058350W WO 2012133644 A1 WO2012133644 A1 WO 2012133644A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
general formula
layer
organic electroluminescent
atom
Prior art date
Application number
PCT/JP2012/058350
Other languages
English (en)
Japanese (ja)
Inventor
陽介 山本
渡辺　康介
外山　弥
伊勢　俊大
Original Assignee
富士フイルム株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 富士フイルム株式会社 filed Critical 富士フイルム株式会社
Priority to KR1020207024699A priority Critical patent/KR102310693B1/ko
Priority to KR1020217031578A priority patent/KR102424152B1/ko
Priority to KR1020187030755A priority patent/KR102034869B1/ko
Priority to KR1020137025153A priority patent/KR101913271B1/ko
Priority to KR1020197030349A priority patent/KR102151116B1/ko
Publication of WO2012133644A1 publication Critical patent/WO2012133644A1/fr

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • 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
    • H10K85/611—Charge transfer complexes
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • C09K2211/1003—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
    • 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
    • C09K2211/1011—Condensed systems
    • 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
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom

Definitions

  • the present invention relates to an organic electroluminescent element, a light emitting device using the element, a display device, a lighting device, and a compound for the element.
  • Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they can emit light with high luminance when driven at a low voltage.
  • An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do.
  • Patent Document 1 describes the use of a dibenzothiophene-based charge transport material for further improving the light emission efficiency and device durability of the device.
  • Patent Document 2 discloses an organic electroluminescent device using a compound in which dibenzothiophene and triphenylene are linked by a phenyl group.
  • Patent Documents 3 and 4 describe organic electroluminescent devices using a compound in which dibenzothiophene is linked by a phenyl group.
  • compound 9S described in Patent Document 2 was found to be inferior in durability, although the chromaticity shift at the time of high-temperature storage was improved as compared with compound 2S having a molecular weight and a glass transition temperature lower than this compound. That is, it was found that it is difficult to improve both durability and chromaticity shift during high-temperature storage by changing the compound used in the organic layer.
  • the problem to be solved by the present invention is to provide an organic electroluminescence device having excellent durability and small chromaticity shift during high-temperature storage.
  • a substrate a pair of electrodes disposed on the substrate and including an anode and a cathode, and an organic layer disposed between the electrodes, wherein the organic layer includes a phosphorescent material and the following general formula ( An organic electroluminescent device comprising the compound represented by 1).
  • X 101 represents an oxygen atom or a sulfur atom
  • R 101 to R 110 represent a hydrogen atom or a substituent (excluding an alkyl group and a cyano group)
  • a plurality of R 108 to R 110 110 may be the same as or different from each other
  • L 101 represents a single bond or an arylene group.
  • At least one R 110 in the general formula (1) is a condensed ring aryl group having 10 to 30 ring members, a condensed ring hetero ring group having 8 to 30 ring members, and a carbon having these as a substituent
  • General formula (2) (In General Formula (2), X 201 represents an oxygen atom or a sulfur atom.
  • R 201 to R 212 each independently represents a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R 208 and R 209 are the same as each other.
  • L 201 represents a single bond or an arylene group and is not a p-terphenylene group
  • one of A 201 and A 202 is a condensed ring aryl group having 10 to 30 ring members, a condensed ring A heteroaryl group having 8 to 30 ring members, an aryl group having 6 to 25 carbon atoms, a heteroaryl group having 5 to 25 ring members, or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent.
  • General formula (3) (In General Formula (3), X 301 represents an oxygen atom or a sulfur atom.
  • R 301 to R 315 each independently represents a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R 308 to R 312 are the same as each other.
  • L 301 represents a single bond or an arylene group, and one of A 301 and A 302 is a condensed ring aryl group having 10 to 30 ring members, or a hetero ring having 8 to 30 ring members that is a condensed ring.
  • An aryl group, an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring members, or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, having 5 to 5 ring members 25 represents a monocyclic heteroaryl group, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.
  • the compound represented by the general formula (1) is a compound represented by any one of the following general formulas (4) to (7) [1] to [6] Organic electroluminescent element.
  • X 401 and X 402 each independently represents an oxygen atom or a sulfur atom.
  • R 401 to R 417 each independently represents a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R 408 R 410 may be the same as or different from each other, and n 401 represents 0 or 1.
  • X 501 represents an oxygen atom or a sulfur atom.
  • R 501 to R 513 independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R 508 to R 413 are the same as each other.
  • n 501 represents 0 or 1.
  • X 601 and X 602 each independently represent an oxygen atom or a sulfur atom.
  • R 601 to R 621 each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R 608 R 613 may be the same as or different from each other.
  • X 701 represents an oxygen atom or a sulfur atom.
  • R 701 to R 716 each independently represents a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R 708 to R 716 are identical to each other. But it may be different.
  • the phosphorescent material is an iridium (Ir) complex represented by the following general formula (E-1): Light emitting element.
  • Z 1 and Z 2 each independently represents a carbon atom or a nitrogen atom.
  • a 1 represents an atomic group that forms a 5- or 6-membered heterocycle together with Z 1 and the nitrogen atom.
  • B 1 represents an atomic group that forms a 5- or 6-membered ring with Z 2 and a carbon atom
  • (XY) represents a monoanionic bidentate ligand
  • n E1 represents an integer of 1 to 3.
  • (In the formula (E-2) are each A E1 ⁇ A E8 independently, nitrogen atom, or, .R E representing a carbon atom substituted with R E represents a hydrogen atom or a substituent.
  • the organic layer includes a light-emitting layer containing the phosphorescent material and another organic layer, and the light-emitting layer contains a compound represented by the general formula (1) [1] ]
  • the organic electroluminescent element according to any one of [9] to [9].
  • the organic layer includes a light-emitting layer containing the phosphorescent material and another organic layer, and the other organic layer is disposed between the light-emitting layer and the cathode and adjacent to the light-emitting layer.
  • the organic electroluminescent element according to any one of [1] to [10], which further comprises a compound represented by the general formula (1).
  • An electron transport layer adjacent to the cathode is provided between the pair of electrodes, and a hole blocking layer adjacent to the opposite side of the electron transport layer to the cathode is optionally provided, and the electron transport layer Or the said hole block layer contains the compound represented by the said General formula (1),
  • the organic layer disposed between the pair of electrodes includes at least one layer formed by vapor deposition of a composition containing a compound represented by the general formula (1) [1] ] The organic electroluminescent element according to any one of [12] to [12]. [14] The organic electroluminescent element as described in any one of [1] to [13], wherein the emission peak wavelength is 490 to 580 nm. [15] A light-emitting device, illumination device, or display device comprising the organic electroluminescent element according to any one of [1] to [14].
  • ADVANTAGE OF THE INVENTION According to this invention, it is excellent in durability and can provide the organic electroluminescent element with a small chromaticity shift
  • a compound useful for an organic electroluminescence device as a charge transport material, a host material of a light emitting layer, and the like.
  • a lighting device can be provided.
  • FIG. 3 is a 1 H-NMR spectrum of the compound 1B-2 of the present invention.
  • FIG. 2 is a 1 H-NMR spectrum of the compound 1B-3 of the present invention.
  • FIG. 2 is a 1 H-NMR spectrum of the compound 1B-4 of the present invention.
  • FIG. 3 is a 1 H-NMR spectrum of the compound 1B-17 of the present invention.
  • FIG. 3 is a 1 H-NMR spectrum of the compound 1D-1 of the present invention.
  • FIG. 2 is a 1 H-NMR spectrum of the compound 1D-3 of the present invention.
  • the organic electroluminescent element of the present invention has a substrate, a pair of electrodes including an anode and a cathode disposed on the substrate, and an organic layer disposed between the electrodes, and the organic layer emits phosphorescence.
  • a material and a compound represented by the following general formula (1) are included.
  • General formula (1) (In the general formula (1), X 101 represents an oxygen atom or a sulfur atom, R 101 to R 110 represent a hydrogen atom or a substituent (excluding an alkyl group and a cyano group), and a plurality of R 108 to R 110 may be the same as or different from each other, and L 101 represents a single bond or an arylene group.
  • an organic electroluminescent device electrons are injected from the cathode and holes are injected from the anode, and these move on the organic molecules and are regenerated in the organic layer (which may be called a light emitting layer functionally). Join.
  • the spin density distribution in the radical state is more broadly delocalized than other phenyl groups and biphenyl groups.
  • the radical species are thermodynamically stabilized as the spin density distribution increases.
  • a dibenzothiophene or dibenzofuran derivative having a p-terphenyl structure can ensure high stability in a radical state.
  • the durability of the organic electroluminescent element could be remarkably improved.
  • the compound having a p-terphenyl structure introduced is less mobile than the m-terphenyl structure, for example, and can prevent changes in the film quality of the organic layer at high temperatures. It is considered that the chromaticity shift of the image could be reduced.
  • the structure of the organic electroluminescent element of the present invention is not particularly limited.
  • FIG. 1 an example of a structure of the organic electroluminescent element of this invention is shown. 1 has an organic layer on a substrate 2 between a pair of electrodes (anode 3 and cathode 9).
  • the element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.
  • the preferable aspect of the organic electroluminescent element of this invention is demonstrated in detail in order of a board
  • the organic electroluminescent element of the present invention has a substrate.
  • the substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer.
  • the organic electroluminescent element of the present invention is disposed on the substrate and has a pair of electrodes including an anode and a cathode.
  • a pair of electrodes including an anode and a cathode.
  • at least one of the pair of electrodes, the anode and the cathode is preferably transparent or translucent.
  • the anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials.
  • the anode is usually provided as a transparent anode.
  • the cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element.
  • the electrode material can be selected as appropriate.
  • the organic electroluminescent element of the present invention has an organic layer disposed between the electrodes, and the organic layer includes a phosphorescent material and a compound represented by the general formula (1).
  • the organic layer includes a phosphorescent material and a compound represented by the general formula (1).
  • the organic layer is formed on the entire surface or one surface of the transparent electrode or the semitransparent electrode.
  • the organic layer is formed on the entire surface or one surface of the transparent electrode or the semitransparent electrode.
  • the configuration of the organic layer, the method for forming the organic layer, preferred embodiments of the layers constituting the organic layer, and materials used for the layers will be described in order.
  • the organic layer preferably includes a charge transport layer.
  • the charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element. Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer. If the charge transport layer is a hole injection layer, a hole transport layer, an electron block layer, or a light emitting layer, it is possible to manufacture an organic electroluminescent element with low cost and high efficiency.
  • the organic electroluminescent element of the present invention preferably has a light emitting layer containing the phosphorescent material and another organic layer, and the light emitting layer contains the compound represented by the general formula (1). Furthermore, in the organic electroluminescent element of the present invention, it is more preferable that the organic layer has a light emitting layer containing the phosphorescent material and another organic layer. However, in the organic electroluminescent element of the present invention, even when the organic layer has a light emitting layer and other organic layers, the layers do not necessarily have to be clearly distinguished.
  • the organic layer contains a phosphorescent material and a compound represented by the general formula (1).
  • the said organic layer has the light emitting layer containing the said phosphorescence-emitting material, and another organic layer, and the said light emitting layer contains the compound represented by the said General formula (1).
  • the compound represented by the general formula (1) is used as a host compound of the light emitting layer.
  • an electron transport layer adjacent to the cathode is provided between the pair of electrodes, and a hole blocking layer adjacent to the side opposite to the cathode of the electron transport layer is optionally included, and the electron transport layer or It is also preferable that the hole blocking layer contains a compound represented by the general formula (1).
  • a plurality of these organic layers may be provided, and when a plurality of layers are provided, they may be formed of the same material, or may be formed of different materials for each layer.
  • each organic layer is formed by a dry film forming method such as a vapor deposition method or a sputtering method, a wet film forming method such as a transfer method, a printing method, a spin coating method, or a bar coating method (solution coating method). Any of these can be suitably formed.
  • the organic layer disposed between the pair of electrodes includes at least one layer formed by vapor deposition of a composition containing the compound represented by the general formula (1). Is preferred.
  • the light emitting layer receives holes from an anode, a hole injection layer, or a hole transport layer when an electric field is applied, receives electrons from a cathode, an electron injection layer, or an electron transport layer, and serves to recombine holes and electrons. It is a layer having a function of providing and emitting light.
  • the light emitting layer in the present invention is not necessarily limited to light emission by such a mechanism.
  • the light emitting layer in the organic electroluminescent element of the present invention preferably contains at least one kind of the phosphorescent material.
  • the light emitting layer in the organic electroluminescent element of the present invention may be composed of only the phosphorescent material, or may be a mixed layer of a host material and the phosphorescent material.
  • the phosphorescent material may be one kind or two or more kinds.
  • the host material is preferably a charge transport material.
  • the host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed.
  • the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
  • the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.
  • the thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm from the viewpoint of external quantum efficiency. More preferably.
  • the light emitting layer contains a compound represented by the general formula (1), and the host material of the light emitting layer is represented by the general formula (1). It is a more preferable embodiment to use a compound.
  • the host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and is a compound that itself does not substantially emit light.
  • substantially does not emit light means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
  • the host material other than the compound represented by the general formula (1), the phosphorescent light emitting material, and the compound represented by the general formula (1) will be described in order.
  • the compound represented by the said General formula (1) may be used other than the said light emitting layer in the organic electroluminescent element of this invention.
  • X 101 represents an oxygen atom or a sulfur atom
  • R 101 to R 110 represent a hydrogen atom or a substituent (excluding an alkyl group and a cyano group)
  • a plurality of R 108 to R 110 may be the same as or different from each other
  • L 101 represents a single bond or an arylene group.
  • the hydrogen atom in the description of the general formula (1) includes an isotope (deuterium atom and the like), and the atoms constituting the substituent further include the isotope.
  • substituted when referred to as “substituent”, the substituent may be substituted.
  • alkyl group in the present invention includes an alkyl group substituted with a fluorine atom (for example, trifluoromethyl group) and an alkyl group substituted with an aryl group (for example, triphenylmethyl group).
  • a fluorine atom for example, trifluoromethyl group
  • an aryl group for example, triphenylmethyl group.
  • X 101 represents an oxygen atom or a sulfur atom.
  • a sulfur atom having a large van der Faals radius is preferred from the viewpoint of improving electron mobility.
  • the substituents represented by R 101 to R 110 are substituents excluding an alkyl group and a cyano group, and can include the following substituent group A independently, Furthermore, you may have a substituent. Examples of the further substituent include a group selected from the substituent group A.
  • Substituent group A An alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), Alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl, 3-pentynyl, etc.), aryl group (preferably carbon 6 to 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, anthryl, etc.), amino group (preferably having carbon number 0-30, more preferably 0-20 carbon atoms, particularly preferably 0-10 carbon atoms, such as amino, methylamino, dimethylamino Diethylamino, dibenzylamino, diphenyla
  • aryloxy group preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms.
  • a heterocyclic oxy group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
  • An acyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as acetyl, benzoyl, formyl, pivaloyl, etc.), alkoxy A carbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, etc.), an aryloxycarbonyl group (preferably Has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl, etc.), an acyloxy group (preferably 2 to 30 carbon atoms, more Preferably it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms.
  • An acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as acetylamino and benzoylamino), alkoxycarbonylamino group (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino), aryloxycarbonylamino group (preferably having carbon number) 7-30, more preferably 7-20 carbon atoms, particularly preferably 7-12 carbon atoms, such as phenyloxycarbonylamino, and the like, and sulfonylamino groups (preferably having 1-30 carbon atoms, more preferably Has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms.
  • a sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms.
  • a carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
  • carbamoyl Methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc.
  • an alkylthio group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio, Ethylthio etc.
  • arylthio group preferably Has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, and the like
  • a heterocyclic thio group preferably 1 to 30 carbon atoms, more
  • it has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like.
  • a group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms such as mesyl, tosyl, etc.
  • a sulfinyl group preferably having 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl and the like. It is.
  • a ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid
  • An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (heteroaryl group)
  • heteroatoms include Nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl , Quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silylyl group, etc.), silyl group ( Preferably, it has 3 to 40 carbon atoms, more preferably 3 to 30 carbon atom,
  • Si group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, triphenylsilyloxy, etc.), phosphoryl group (for example, A diphenylphosphoryl group, a dimethylphosphoryl group, etc.).
  • substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
  • R 101 to R 110 are each independently preferably a hydrogen atom, an aryl group or a heteroaryl group.
  • the aryl group represented by R 101 to R 110 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 18 carbon atoms.
  • a phenyl group, a xylyl group, a biphenyl group, A phenyl group, a naphthyl group, an anthryl group, a triphenylenyl group, etc. are mentioned.
  • the heteroaryl group represented by R 101 to R 110 preferably has 5 to 30 ring members, more preferably 5 to 20 ring members, and particularly preferably 5 to 15 ring members.
  • a pyridyl group for example, a pyridyl group, pyrimidinyl group, triazinyl group, Examples include pyrazinyl group, pyridazinyl group, carbazolyl group, dibenzothiophenyl group, dibenzofuranyl group and the like.
  • R 101 to R 107 are more preferably each independently a hydrogen atom or an aryl group having 6 to 18 carbon atoms, particularly preferably a hydrogen atom or a phenyl group, and more preferably a hydrogen atom.
  • R 101 to R 107 is a phenyl group is preferable, and an embodiment in which 1 or 2 is a phenyl group is also more preferable.
  • R 108 and R 109 are preferably a hydrogen atom, an aryl group having 6 to 18 carbon atoms or a heteroaryl group.
  • both R 108 and R 109 in the general formula (1) are hydrogen. More preferably it is an atom.
  • the substituent is preferably a substituted or unsubstituted aryl group or heteroaryl group, and more preferably a phenyl group.
  • R 110 examples include an aryl group having 10 to 30 ring members in which at least one R 110 is a condensed ring, a heteroaryl group having 8 to 30 ring members that is a condensed ring, and 6 to 25 carbon atoms having these as substituents.
  • At least one R 110 is an aryl group having 12 to 18 ring members that is a condensed ring, a heteroaryl group having 9 to 13 ring members that is a condensed ring, or 6 to 18 carbon atoms having these as a substituent.
  • the monocyclic heteroaryl group having 6 to 13 ring members having a monocyclic aryl group having 6 to 18 carbon atoms as a substituent is a ring having a monocyclic aryl group having 6 to 10 carbon atoms as a substituent. It is preferably a monocyclic heteroaryl group having 6 to 10 members, and the preferred number of monocyclic aryl groups having 6 to 10 carbon atoms is 1 or 2.
  • the position of the substituent may be any of the ortho, meta, and para positions relative to the substituent that forms the p-terphenylene skeleton of the benzene ring substituted by R 110 , and among these, the meta position Or it is preferable that it is para position from a viewpoint of suppressing the photocyclization reaction between this R110 and another substituent, or a viewpoint of a device drive voltage reduction. Further, when the emission color from the organic electroluminescence element is green (emission peak wavelength is 490 to 580 nm), the meta position is more preferable from the viewpoint of emission efficiency.
  • L 101 represents a single bond or an arylene group.
  • the arylene group may be a condensed ring (for example, naphthyl group, anthryl group, etc.), but when the emission color from the organic electroluminescence device is green (emission peak wavelength is 490 to 580 nm), it is condensed from the viewpoint of luminous efficiency.
  • An arylene group having no ring is preferable, and a phenylene group which may have a substituent or a structure in which a plurality of the phenylene groups are connected by a single bond is more preferable.
  • Preferred examples of the arylene group represented by L 101 include a phenylene group, a biphenylene group, and a terphenylene group.
  • L 101 is preferably a single bond, a phenylene group, a biphenylene group or a terphenylene group, preferably a single bond or a terphenylene group (preferably a p-terphenylene group or an m-terphenylene group, more preferably a p-terphenylene group.
  • An unsubstituted p-terphenylene group is particularly preferred) and a single bond is more preferred.
  • p-terphenylene and m-terphenylene each represent the following structure (* represents a bond).
  • L 201 is preferably unsubstituted, but may optionally have a substituent.
  • substituents in the case where L 201 has a further substituent include the substituent group A, and a substituted or unsubstituted aryl group (phenyl group or biphenyl group) is preferable, and a phenyl group is preferable.
  • the compound represented by the general formula (1) is preferably a compound represented by the following general formula (2) or (3).
  • X201 represents an oxygen atom or a sulfur atom.
  • R 201 to R 212 each independently represents a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R 208 and R 209 may be the same or different from each other.
  • L 201 represents a single bond or an arylene group and is not a p-terphenylene group.
  • a 201 and A 202 is a condensed ring aryl group having 10 to 30 ring members, a condensed ring hetero ring group having 8 to 30 ring members, an aryl group having 6 to 25 carbon atoms having these as a substituent, or Represents a heteroaryl group having 5 to 25 ring members or a monocyclic heteroaryl group having 5 to 25 ring members having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, the other being a hydrogen atom, aryl Represents a group or a heteroaryl group.
  • a preferred range of X 201 in formula (2) is the same as the preferred range of X 101 in formula (1).
  • R 201 to R 209 in the general formula (2) is the same as the preferred range of R 101 to R 109 in the general formula (1).
  • R 210 to R 212 in the general formula (2) are preferably a hydrogen atom or an aryl group having 6 to 20 carbon atoms, and more preferably a hydrogen atom.
  • the aryl group having 10 to 30 ring members that is a condensed ring represented by one of A 201 and A 202 in the general formula (2), the heteroaryl group having 8 to 30 ring members that is a condensed ring, and a carbon having these as a substituent Preferred are an aryl group having 6 to 25 rings, a heteroaryl group having 5 to 25 ring members, or a monocyclic heteroaryl group having 5 to 25 ring members having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent.
  • the range is a dibenzothiophenyl group, a dibenzofuranyl group, a triphenylenyl group, a carbazolyl group, an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring members, or a carbon number of 6 to It is a monocyclic heteroaryl group having 5 to 25 ring members and having 13 monocyclic aryl groups as substituents.
  • a dibenzothiophenyl group, a dibenzofuranyl group, a triphenylenyl group or a phenylene group having these substituents is more preferable, and a dibenzothiophenyl group, a dibenzofuranyl group or a triphenylenyl group is particularly preferable.
  • a dibenzothiophenyl group or a triphenylenyl group is more particularly preferable, and a triphenylenyl group is more preferable.
  • these condensed rings may have the above skeleton as a basic skeleton and further may be condensed with each other.
  • a 201 and A 202 in the general formula (2) is preferably a hydrogen atom, an aryl group having 6 to 25 carbon atoms, or a heteroaryl group having 5 to 25 ring members, and preferably a hydrogen atom. More preferred.
  • L 201 in the general formula (2) represents a single bond or an arylene group and is not a p-terphenylene group.
  • the arylene group represented by L 201 may be a condensed ring (for example, naphthyl group, anthryl group, etc.). From the viewpoint, it is preferably an arylene group having no condensed ring, more preferably a phenylene group, a biphenylene group, or an m-terphenylene group, and a 1,3-phenylene group or a 3,5′-biphenylene group. It is particularly preferred.
  • L 201 in the general formula (2) is preferably a single bond.
  • X 301 represents an oxygen atom or a sulfur atom.
  • R 301 to R 315 each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and the plurality of R 308 to R 312 may be the same or different from each other.
  • L 301 represents a single bond or an arylene group.
  • a 301 and A 302 is a condensed ring aryl group having 10 to 30 ring members, a condensed ring hetero ring group having 8 to 30 ring members, an aryl group having 6 to 25 carbon atoms having these as a substituent, or Represents a heteroaryl group having 5 to 25 ring members or a monocyclic heteroaryl group having 5 to 20 ring members having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, the other being a hydrogen atom, aryl Represents a group or a heteroaryl group.
  • the preferable range of X 301 in the general formula (3) is the same as the preferable range of X 101 in the general formula (1).
  • the preferred range of R 301 to R 312 in the general formula (3) is the same as the preferred range of R 101 to R 109 in the general formula (1).
  • the preferred range of R 313 to R 315 in the general formula (3) is the same as the preferred range of R 210 to R 212 in the general formula (2).
  • the preferred ranges of A 301 and A 302 in the general formula (3) are the same as the preferred ranges of A 201 and A 202 in the general formula (2).
  • the arylene group represented by L 301 in the general formula (3) may be a condensed ring (eg, naphthyl group, anthryl group, etc.), but the emission color from the organic electroluminescence element is green (emission peak wavelength is 490 to 580 nm).
  • an arylene group having no condensed ring is preferable from the viewpoint of luminous efficiency, more preferably a phenylene group, a biphenylene group, or an m-terphenylene group, and a 1,3-phenylene group or 3, A 5′-biphenylene group is particularly preferred.
  • L 301 in the general formula (3) is preferably a single bond.
  • the compound represented by the general formula (1) is a compound represented by any one of the following general formulas (4) to (7) and a general formula (11) described below. It is particularly preferable that the compound represented by the general formula (1) is more particularly preferably a compound represented by any one of the following general formulas (4) to (7).
  • X 401 and X 402 each independently represent an oxygen atom or a sulfur atom.
  • R 401 to R 417 each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and the plurality of R 408 to R 410 may be the same as or different from each other.
  • n 401 represents 0 or 1;
  • the preferable range of X 401 and X 402 in the general formula (4) is the same as the preferable range of X 101 in the general formula (1).
  • R 401 to R 407 and R 411 to R 417 in the general formula (4) are the same as the preferred ranges of R 101 to R 107 in the general formula (1).
  • the preferable range of R 408 to R 410 in the general formula (4) is the same as the preferable range of R 108 and R 109 in the general formula (1).
  • n 401 is preferably 0.
  • X501 represents an oxygen atom or a sulfur atom.
  • R 501 to R 513 each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and the plurality of R 508 to R 413 may be the same as or different from each other.
  • n 501 represents 0 or 1;
  • the preferable range of X 501 in the general formula (5) is the same as the preferable range of X 101 in the general formula (1).
  • R 501 to R 507 in the general formula (5) is the same as the preferred range of R 101 to R 107 in the general formula (1).
  • the preferred range of R 508 to R 510 in the general formula (5) is the same as the preferred range of R 108 and R 109 in the general formula (1).
  • R 511 to R 513 in the general formula (5) are preferably a hydrogen atom, an aryl group having 6 to 25 carbon atoms, or a heteroaryl group having 5 to 25 ring members, and more preferably a hydrogen atom.
  • n 501 is preferably 0.
  • X601 and X602 each independently represent an oxygen atom or a sulfur atom.
  • R 601 to R 621 each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and the plurality of R 608 to R 613 may be the same as or different from each other.
  • the preferable range of X 601 and X 602 in the general formula (6) is the same as the preferable range of X 101 in the general formula (1).
  • R 601 to R 607 and R 614 to R 620 in the general formula (6) are the same as the preferred ranges of R 101 to R 107 in the general formula (1).
  • the preferred range of R 608 to R 613 in the general formula (6) is the same as the preferred range of R 108 and R 109 in the general formula (1).
  • X701 represents an oxygen atom or a sulfur atom.
  • R 701 to R 716 each independently represents a hydrogen atom, an aryl group or a heteroaryl group, and the plurality of R 708 to R 716 may be the same as or different from each other.
  • the preferable range of X 701 in the general formula (7) is the same as the preferable range of X 101 in the general formula (1).
  • the preferred range of R 701 to R 707 in the general formula (7) is the same as the preferred range of R 101 to R 107 in the general formula (1).
  • the preferable range of R 708 to R 713 in the general formula (7) is the same as the preferable range of R 108 and R 109 in the general formula (1).
  • the preferred range of R 714 to R 716 in the general formula (7) is the same as the preferred range of R 511 to R 513 in the general formula (5).
  • a compound represented by any one of the following general formulas (8) to (11) is particularly preferable.
  • the compound of the present invention represented by any one of the following general formulas (8) to (11) is an organic material such as an electrophotography, an organic transistor, an organic photoelectric conversion element (for energy conversion, a sensor, etc.), and an organic electroluminescence element. It can be preferably used for an electronic device, and is particularly preferably used for an organic electroluminescent device.
  • X 801 to X 806 each independently represents an oxygen atom or a sulfur atom
  • R 801 to R 806 each independently represents a hydrogen atom or an aryl group having 6 to 13 carbon atoms.
  • a 11 to A 13 each independently represents CH or a nitrogen atom, and at least one is a nitrogen atom.
  • the preferable range of X 801 to X 806 is the same as the preferable range of X 101 in the general formula (1).
  • R 801 to R 806 are each independently preferably a hydrogen atom or a phenyl group, and more preferably a hydrogen atom.
  • a 11 to A 13 each independently represent CH or a nitrogen atom, and at least one is a nitrogen atom. When A 11 to A 13 contain one nitrogen atom, A 11 or A 12 is preferably a nitrogen atom. When there are two nitrogen atoms contained in A 11 to A 13 , it is preferable that A 12 and A 13 are nitrogen atoms.
  • the compound represented by the general formula (11) has one nitrogen atom contained in A 11 to A 13 and A 11 or A 12 is a nitrogen atom, or a nitrogen atom contained in A 11 to A 13 More preferably, A 12 and A 13 are two nitrogen atoms, or A 11 to A 13 are all nitrogen atoms. Further among them, A 11 ⁇ A compound nitrogen atom is one A 12 is a nitrogen atom contained in the 13, A 11 nitrogen atoms contained in the ⁇ A 13 2 Tsude A 12 and A 13 is a nitrogen atom Is particularly preferred.
  • the compound represented by the general formula (11) has a “nitrogen-containing heterocycle” capable of deepening LUMO, which is preferable from the viewpoint of reducing device voltage. Moreover, it is preferable also from a viewpoint with small chromaticity deviation at the time of high temperature storage.
  • the molecular weight of the compound represented by the general formula (1) is usually 400 or more and 1500 or less, preferably 450 or more and 1200 or less, more preferably 500 or more and 1100 or less, and more preferably 550 or more and 1000 or less. Is more preferable.
  • the molecular weight is 450 or more, it is advantageous for forming a high-quality amorphous thin film, and when the molecular weight is 1200 or less, the solubility and sublimation property are improved, which is advantageous for improving the purity of the compound.
  • the molecular weight of the compound represented by the general formula (1) is preferably 550 or more from the viewpoint of reducing the chromaticity shift during high temperature storage.
  • the molecular weight of the compound represented by the general formula (1) is preferably 1200 or less.
  • the compound represented by the general formula (1) When the compound represented by the general formula (1) is used as a host material of a light emitting layer of an organic electroluminescence device or a charge transport material of a layer adjacent to the light emitting layer, an energy gap in a thin film state from the light emitting material (present invention)
  • the light emitting material is a phosphorescent light emitting material such as the organic electroluminescent element
  • T 1 lowest excited triplet
  • the energy gap and T 1 energy are not too large.
  • the T 1 energy in the film state of the compound represented by the general formula (1) is preferably 1.77 eV (40 kcal / mol) or more and 3.51 eV (81 kcal / mol) or less and preferably 2.39 eV (55 kcal). / Mol) or more and 3.25 eV (75 kcal / mol) or less.
  • the T 1 energy is 2.39 eV (55 kcal / mol) or more and 2.82 eV (65 kcal / mol) from the viewpoint of emission efficiency. mol) or less.
  • the T 1 energy can be determined from the short wavelength end of a phosphorescence emission spectrum of a thin film of material. For example, a material is deposited on a cleaned quartz glass substrate to a thickness of about 50 nm by vacuum deposition, and the phosphorescence emission spectrum of the thin film is measured at F-7000 Hitachi Spectrofluorimeter (Hitachi High Technologies) under liquid nitrogen temperature. Use to measure. T 1 energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.
  • the organic electroluminescent element of the present invention has the general formula (
  • the compound represented by 1) is preferably a compound having a glass transition temperature of 100 ° C. or higher.
  • the glass transition temperature (Tg) of the compound represented by the general formula (1) is more preferably from 100 ° C to 400 ° C, particularly preferably from 120 ° C to 400 ° C, and from 140 ° C to 400 ° C. More preferably, it is as follows.
  • the purity of the compound represented by the general formula (1) When the purity of the compound represented by the general formula (1) is low, impurities work as traps for charge transport or promote deterioration of the device. Therefore, the purity of the compound represented by the general formula (1) The higher the better.
  • the purity can be measured by, for example, high performance liquid chromatography (HPLC), and the area ratio of the compound represented by the general formula (1) when detected with a light absorption intensity of 254 nm is preferably 95.0% or more, and more It is preferably 97.0% or more, particularly preferably 99.0% or more, and most preferably 99.9% or more.
  • Examples of a method for increasing the purity of the compound represented by the general formula (1) include sublimation purification.
  • the compound exemplified as the compound represented by the general formula (1) is a metal catalyst (for example, between a corresponding boronic acid or boronic ester or boronic ester salt and a corresponding halogen compound or triflate compound). It can be synthesized by a coupling reaction (for example, Suzuki-Miyaura coupling) using a ligand (such as triphenylphosphine or Buchwald ligand) with Pd or Ni. For example, it can be synthesized by the method described in Patent Document 1 described above.
  • the compound represented by the general formula (1) is not limited in its use and may be contained in any layer in the organic layer.
  • Examples of the introduction layer of the compound represented by the general formula (1) include the light emitting layer, a layer between the light emitting layer and the cathode (particularly, a layer adjacent to the light emitting layer), and between the light emitting layer and the anode. It is preferably contained in any one of the above layers, more preferably contained in any one or more of the light emitting layer, the electron transport layer, the electron injection layer, the exciton block layer, the hole block layer, and the electron block layer.
  • the compound represented by the said General formula (1) is more preferably contained in any one of the light emitting layer, the electron transporting layer, and the hole blocking layer, and particularly preferably contained in the light emitting layer or the electron transporting layer.
  • the compound represented by the general formula (1) is contained in the light emitting layer, the compound represented by the general formula (1) is included in an amount of 0.1 to 99% by mass with respect to the total mass of the light emitting layer.
  • the content is preferably 1 to 97% by mass, more preferably 10 to 96% by mass.
  • the compound represented by the general formula (1) is further contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass with respect to the total mass of the layer other than the light emitting layer. More preferably, it is contained by mass%.
  • the light emitting layer has at least one phosphorescent material.
  • a fluorescent light emitting material or a phosphorescent light emitting material different from the phosphorescent light emitting material contained in the light emitting layer can be used as the light emitting material. Details of these fluorescent materials and phosphorescent materials are described in, for example, paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph numbers [0088] to [0090] of JP-A-2007-266458. The matters described in these publications can be applied to the present invention.
  • Examples of phosphorescent light-emitting materials that can be used in the present invention include US Pat. / 19373A2, JP-A No. 2001-247859, JP-A No. 2002-302671, JP-A No. 2002-117978, JP-A No. 2003-133074, JP-A No. 2002-1235076, JP-A No. 2003-123684, JP-A No. 2002-170684, EP No. 121157, JP-A No.
  • Examples of the light emitting material include iridium (Ir) complex, platinum (Pt) complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu.
  • Examples include phosphorescent metal complex compounds such as complexes, Tb complexes, Gd complexes, Dy complexes, and Ce complexes.
  • an iridium (Ir) complex particularly preferred is an iridium (Ir) complex, a platinum (Pt) complex, or a Re complex.
  • at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, or a metal-sulfur bond is used.
  • An iridium (Ir) complex, a platinum (Pt) complex, or a Re complex is preferable.
  • iridium (Ir) complex and platinum (Pt) complex are particularly preferable, and iridium (Ir) complex is most preferable from the viewpoint of luminous efficiency, driving durability, chromaticity and the like.
  • These phosphorescent metal complex compounds are preferably contained in the light emitting layer together with the compound represented by the general formula (1).
  • iridium (Ir) complex represented by the following general formula (E-1) As the phosphorescent material contained in the light emitting layer, it is preferable to use an iridium (Ir) complex represented by the following general formula (E-1). Hereinafter, the iridium (Ir) complex represented by the general formula (E-1) will be described.
  • Z 1 and Z 2 each independently represents a carbon atom or a nitrogen atom.
  • a 1 represents an atomic group that forms a 5- or 6-membered heterocycle with Z 1 and a nitrogen atom.
  • B 1 represents an atomic group that forms a 5- or 6-membered ring with Z 2 and a carbon atom.
  • (XY) represents a monoanionic bidentate ligand.
  • n E1 represents an integer of 1 to 3.
  • n E1 represents an integer of 1 to 3, preferably 2 or 3.
  • n E1 is 2 or 3
  • a plurality of ligands may be the same as or different from each other.
  • Z 1 and Z 2 each independently represents a carbon atom or a nitrogen atom.
  • Z 1 and Z 2 are preferably carbon atoms.
  • a 1 represents an atomic group that forms a 5- or 6-membered heterocycle with Z 1 and a nitrogen atom.
  • Examples of the 5- or 6-membered heterocycle containing A 1 , Z 1 and a nitrogen atom include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole Ring, thiadiazole ring and the like.
  • the 5- or 6-membered hetero ring formed by A 1 , Z 1 and a nitrogen atom is preferably a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole.
  • the 5- or 6-membered heterocycle formed by A 1 , Z 1 and a nitrogen atom may have a substituent, and the substituent group A can be applied as the substituent.
  • the substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable.
  • an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, a heteroaryl group and the like are selected.
  • an electron withdrawing group is preferable, and for example, a cyano group or a perfluoroalkyl group is preferably selected.
  • an alkyl group, a cycloalkyl group, an aryl group or the like is preferably selected.
  • the substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.
  • the substituent on the nitrogen is preferably an alkyl group, an aryl group, or a heteroaryl group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
  • the substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.
  • B 1 represents a 5- or 6-membered ring containing Z 2 and a carbon atom.
  • Examples of the 5- or 6-membered ring formed by B 1 , Z 2 and a carbon atom include a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, Examples include a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, and a furan ring.
  • the 5- or 6-membered ring formed by B 1 , Z 2 and carbon atom is preferably a benzene ring, pyridine ring, pyrazine ring, imidazole ring, pyrazole A ring and a thiophene ring, more preferably a benzene ring, a pyridine ring and a pyrazole ring, and still more preferably a benzene ring and a pyridine ring.
  • the 5- or 6-membered ring formed of B 1 , Z 2 and a carbon atom may have a substituent, and the substituent group A is a substituent on a nitrogen atom as a substituent on the carbon atom.
  • the following substituent group B can be applied.
  • the substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.
  • Substituent group B An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl , 3-pentynyl, etc.), aryl groups (preferably having 6 to 30 carbon
  • the substituent on the carbon is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group. , Aryl groups, heteroaryl groups and the like are selected.
  • an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group, and the like are selected.
  • an alkyl group, a cycloalkyl group, an aryl group or the like is preferably selected.
  • the substituent on the nitrogen is preferably an alkyl group, an aryl group, or a heteroaryl group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
  • the substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like.
  • These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.
  • a 5- or 6-membered heterocyclic substituent formed by A 1 , Z 1 and a nitrogen atom and a 5- or 6-membered substituent formed by B 1 , Z 2 and a carbon atom are linked. Then, the same condensed ring as described above may be formed.
  • (XY) represents a bidentate monoanionic ligand. Examples of bidentate monoanionic ligands are described on pages 89-90 of Lamansky et al., WO 02/15645.
  • the bidentate monoanionic ligand represented by (XY) is preferably a bidentate monoanionic ligand represented by the following general formula (L-1).
  • R L1 and R L2 each independently represent an alkyl group, an aryl group, or a heteroaryl group.
  • R L3 represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.
  • the alkyl group represented by R L1 to R L3 may have a substituent and may be saturated or unsaturated.
  • substituent Z ′ examples include the following substituent Z ′, and preferred substituent Z ′ includes a phenyl group, a heteroaryl group, a fluorine atom, a silyl group, an amino group, a cyano group, or a combination thereof. And a phenyl group, a fluorine atom, and a cyano group are more preferable.
  • the alkyl group represented by R L1 to R L3 is preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms.
  • Aryl group having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, such as phenyl group, naphthyl group, anthracenyl group, tetracenyl group, pyrenyl group, perylenyl group, triphenylenyl group
  • the aryl group represented by R L1 to R L3 may be condensed or may have a substituent.
  • substituents include the above-described substituent Z ′, and the substituent Z ′ is preferably an alkyl group or an aryl group, and more preferably an alkyl group.
  • the aryl group represented by R L1 ⁇ R L3 is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms.
  • the heteroaryl group represented by R L1 to R L3 may be condensed or may have a substituent.
  • substituent Z ′ examples include the above-described substituent Z ′, and the substituent Z ′ is preferably an alkyl group or an aryl group, and more preferably an alkyl group.
  • the heteroaryl group represented by R L1 to R L3 is preferably a heteroaryl group having 4 to 12 carbon atoms, and more preferably a heteroaryl group having 4 to 10 carbon atoms.
  • R L1 and R L2 are preferably an alkyl group or an aryl group, more preferably an alkyl group or a phenyl group, and particularly preferably an alkyl group.
  • the alkyl group represented by R L1 and R L2 is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 5 carbon atoms in total, such as a methyl group or an ethyl group N-propyl group, iso-propyl group, iso-butyl group, t-butyl group, n-butyl group, cyclohexyl group and the like, and methyl group, ethyl group, iso-butyl group, or t-butyl group is A methyl group is preferable, and a methyl group is particularly preferable.
  • R L3 is preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.
  • a preferred embodiment of the iridium (Ir) complex represented by the general formula (E-1) is an iridium (Ir) complex material represented by the following general formula (E-2). Next, general formula (E-2) will be described.
  • a E1 to A E8 each independently represents a nitrogen atom or C—R E.
  • R E represents a hydrogen atom or a substituent.
  • (XY) represents a monoanionic bidentate ligand.
  • n E2 represents an integer of 1 to 3.
  • a E1 to A E8 each independently represent a nitrogen atom or C—R E.
  • R E represents a hydrogen atom or a substituent, and R E may be connected to each other to form a ring.
  • Examples of the ring formed include the same ring as the condensed ring described in the general formula (E-1).
  • Examples of the substituent represented by R E we are the same as those mentioned above substituent group A.
  • a E1 ⁇ A E4 is C-R E, if A E1 ⁇ A E4 is C-R E, preferably a hydrogen atom R E of A E3, alkyl group, aryl group, amino group, An alkoxy group, an aryloxy group, a fluorine atom, or a cyano group, more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, and particularly preferably a hydrogen atom or a fluorine atom.
  • R E of A E1 , A E2 and A E4 is preferably a hydrogen atom, alkyl group, aryl group, amino group, alkoxy group, aryloxy group, fluorine atom or cyano group, more preferably a hydrogen atom, An alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, particularly preferably a hydrogen atom.
  • a E5 to A E8 are preferably C—R E , and when A E5 to A E8 are C—R E , R E is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, heteroaryl Group, dialkylamino group, diarylamino group, alkyloxy group, cyano group, or fluorine atom, more preferably a hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, dialkylamino group, cyano group, or fluorine atom. And more preferably a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom.
  • a E6 is preferably a nitrogen atom.
  • (X-Y) and n E2 of the general formula in (E1) (X-Y) , and has the same meaning as n E1 preferable ranges are also the same.
  • a more preferred form of the compound represented by the general formula (E-2) is a compound represented by the following general formula (E-3).
  • R T1 , R T2 , R T3 , R T4 , R T5 , R T6 and R T7 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl group, —CO 2 R, —C (O) R, —NR 2 , —NO 2 , —OR, halogen atom, aryl group or heteroaryl group, and further substituents Z may be included.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • A represents CR ′ or a nitrogen atom
  • R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO 2 R, —C (O ) R, —NR 2 , —NO 2 , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent Z.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • R T1 to R T7 and R ′ may be bonded together to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl
  • the condensed 4- to 7-membered ring may further have a substituent Z.
  • R T1 and R T7 , or R T5 and R T6 are condensed to form a benzene ring is preferred, and the case where R T5 and R T6 are condensed to form a benzene ring is particularly preferred.
  • Z is independently a halogen atom, -R “, -OR", -N (R ") 2 , -SR", -C (O) R “, -C (O) OR", -C (O) N (R ") 2, -CN , -NO 2, -SO 2, -SOR", - SO 2 R “, or -SO 3 R” represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
  • (XY) represents a monoanionic bidentate ligand.
  • n E3 represents an integer of 1 to 3.
  • the alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z.
  • the alkyl group represented by R T1 to R T7 and R ′ is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as methyl Group, ethyl group, i-propyl group, cyclohexyl group, t-butyl group and the like.
  • the cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z.
  • the cycloalkyl group represented by R T1 to R T7 and R ′ is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total. A cyclopentyl group, a cyclohexyl group, etc. are mentioned.
  • the alkenyl group represented by R T1 to R T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • vinyl, allyl Examples include 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
  • the alkynyl group represented by R T1 to R T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • R T1 to R T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • Examples of the perfluoroalkyl group represented by R T1 to R T7 and R ′ include those in which all the hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.
  • the aryl group represented by R T1 to R T7 and R ′ is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, a naphthyl group, and the like.
  • the heteroaryl group represented by R T1 to R T7 and R ′ is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted heteroaryl group.
  • Groups such as pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, furyl, benzofuryl , Thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group, benzis
  • R T1 to R T7 and R ′ are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group, or a heteroaryl group, more preferably A hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, and an aryl group are preferable, and a hydrogen atom, an alkyl group, and an aryl group are more preferable.
  • substituent Z an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom is more preferable.
  • R T1 to R T7 and R ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl;
  • the condensed 4- to 7-membered ring may further have a substituent Z.
  • the definition and preferred range of cycloalkyl, aryl and heteroaryl formed are the same as the cycloalkyl group, aryl group and heteroaryl group defined by R T1 to R T7 and R ′.
  • A represents CR ′, and among R T1 to R T7 and R ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms, and R T1 to R T7 , And R ′ are particularly preferably a case where 0 to 2 are alkyl groups and the rest are all hydrogen atoms.
  • n E3 is preferably 2 or 3.
  • the plurality of ligands may be the same or different.
  • the type of ligand in the complex is preferably composed of 1 to 2 types.
  • (XY) has the same meaning as (XY) in formula (E-1), and the preferred range is also the same.
  • One preferred form of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-4).
  • R T1 to R T4 , A, (XY) and n E4 in the general formula (E-4) are R T1 to R T4 , A, (XY) and n E3 in the general formula (E-3).
  • the preferred range is also the same.
  • R 1 ′ to R 5 ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl group, —CO 2 R, —C (O) R.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • R 1 ′ to R 5 ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl;
  • the condensed 4- to 7-membered ring may further have a substituent Z.
  • Z is independently a halogen atom, -R “, -OR", -N (R ") 2 , -SR", -C (O) R “, -C (O) OR", -C (O) N (R ") 2, -CN , -NO 2, -SO 2, -SOR", - SO 2 R “, or -SO 3 R” represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
  • R 1 ′ to R 5 ′ are the same as R T1 to R T7 and R ′ in formula (E-3). Further, it is particularly preferable that A represents CR ′, and 0 to 2 of R T1 to R T4 , R ′, and R 1 ′ to R 5 ′ are alkyl groups or phenyl groups, and the rest are all hydrogen atoms. More preferably, 0 to 2 of R T1 to R T4 , R ′, and R 1 ′ to R 5 ′ are alkyl groups and the rest are all hydrogen atoms.
  • the compounds exemplified as the compound represented by the general formula (E-1) can be synthesized by the method described in JP-A-2009-99783, various methods described in US Pat. No. 7,279,232 and the like. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.
  • the phosphorescent light emitting material is preferably contained in the light emitting layer, but its application is not limited and may be further contained in any layer in the organic layer.
  • the phosphorescent light-emitting material in the light-emitting layer is preferably contained in the light-emitting layer in an amount of 0.1% by mass to 50% by mass with respect to the total amount of compounds generally forming the light-emitting layer. From the viewpoint of external quantum efficiency, the content is more preferably 1% by mass to 50% by mass, and particularly preferably 2% by mass to 40% by mass.
  • a compound represented by any one of the general formulas (1) to (7) and a compound represented by any one of the general formulas (E-1) to (E-4) are used in combination in the light emitting layer. Is particularly preferred in the present invention.
  • Examples of other host materials that can be used for the light emitting layer other than the compound represented by the general formula (1) include compounds having the following structure as a partial structure. it can. Aromatic hydrocarbon, pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styryl Conductivity such as anthracene, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, porphyrin compound, polysilane compound, poly (N-vinylcarbazole), aniline copolymer, thiophene oligomer, polythiophene Polymer oligomer, organic silane
  • the organic electroluminescent element of the present invention may have other layers other than the light emitting layer.
  • Other organic layers other than the light emitting layer that the organic layer may have include a hole injection layer, a hole transport layer, a block layer (hole block layer, exciton block layer, etc.), an electron transport layer, and the like. Is mentioned. Examples of the specific layer configuration include the following, but the present invention is not limited to these configurations.
  • the organic electroluminescent element of the present invention preferably includes (A) at least one organic layer preferably disposed between the anode and the light emitting layer.
  • Examples of the organic layer (A) preferably disposed between the anode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron block layer from the anode side.
  • the organic electroluminescent element of the present invention preferably includes (B) at least one organic layer preferably disposed between the cathode and the light emitting layer.
  • Examples of the organic layer (B) preferably disposed between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer from the cathode side.
  • an example of a preferred embodiment of the organic electroluminescent element of the present invention is the embodiment described in FIG. 1, and as the organic layer, a hole injection layer 4, a hole transport layer 5, In this embodiment, the light emitting layer 6, the hole blocking layer 7, and the electron transport layer 8 are laminated in this order.
  • the organic layer a hole injection layer 4, a hole transport layer 5, In this embodiment, the light emitting layer 6, the hole blocking layer 7, and the electron transport layer 8 are laminated in this order.
  • other layers other than the light emitting layer which may be included in the organic electroluminescent element of the present invention will be described.
  • the hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
  • the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention.
  • the hole injection layer preferably contains an electron accepting dopant.
  • an electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the doped material and generate radical cations.
  • TCNQ tetracyanoquinodimethane
  • F 4 -TCNQ tetrafluorotetracyanoquinodimethane
  • molybdenum oxide and the like.
  • the electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and preferably 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the hole injection layer. %, More preferably 0.2% by mass to 30% by mass.
  • the electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side.
  • an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
  • the T 1 energy in the film state of the organic compound composing the electron blocking layer must be higher than the T 1 energy of the light emitting material in order to prevent energy transfer of excitons generated in the light emitting layer and not to reduce the light emission efficiency. Is preferred.
  • the organic compound constituting the electron blocking layer for example, those mentioned as the hole transport material described above can be applied.
  • the thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • (A-3) Material particularly preferably used in the organic layer preferably disposed between the anode and the light emitting layer [compound represented by formula (M-1)]
  • the organic electroluminescent device of the present invention is represented by at least one of the following general formula (M-1) as a material particularly preferably used for the organic layer preferably disposed between the anode (A) and the light emitting layer. Can be mentioned.
  • the compound represented by the general formula (M-1) is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the anode, but its use is not limited, and the organic layer It may be further contained in any of the layers.
  • the introduction layer of the compound represented by the general formula (M-1) any of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge blocking layer, or a plurality of layers can be used. Can be contained.
  • the organic layer adjacent to the light emitting layer between the light emitting layer and the anode and containing the compound represented by the general formula (M-1) is more preferably an electron blocking layer or a hole transporting layer.
  • Ar 1 and Ar 2 are each independently one or more selected from alkyl, aryl, heteroaryl, arylamino, alkylamino, morpholino, thiomorpholino, N, O, and S Represents a 5- or 6-membered heterocycloalkyl or cycloalkyl containing a heteroatom, and may further have a substituent Z.
  • Ar 1 and Ar 2 may be bonded to each other by a single bond, alkylene, or alkenylene (with or without a condensed ring) to form a condensed 5- to 9-membered ring.
  • Ar 3 represents P-valent alkyl, aryl, heteroaryl, or arylamino, and may further have a substituent Z.
  • Z is independently a halogen atom, -R “, -OR", -N (R ") 2 , -SR", -C (O) R “, -C (O) OR", -C (O) N (R ") 2, -CN , -NO 2, -SO 2, -SOR", - SO 2 R “, or -SO 3 R” represents, R “are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
  • p is an integer of 1 to 4, and when p is 2 or more, Ar 1 and Ar 2 may be the same or different.
  • Another preferable embodiment of the compound represented by the general formula (M-1) is a case represented by the following general formula (M-2).
  • R M1 represents an alkyl group, an aryl group, or a heteroaryl group.
  • R M2 to R M23 each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, a cyano group, a nitro group, or a fluorine atom.
  • R M1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). Which may have the aforementioned substituent Z.
  • R M1 is preferably an aryl group or a heteroaryl group, and more preferably an aryl group.
  • Preferable substituents when the aryl group of R M1 has a substituent include an alkyl group, a halogen atom, a cyano group, an aryl group, and an alkoxy group, and an alkyl group, a halogen atom, a cyano group, and an aryl group are more preferable.
  • the aryl group of R M1 is preferably a phenyl group that may have a substituent Z, and more preferably a phenyl group that may have an alkyl group or a cyano group.
  • R M2 to R M23 are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), a heteroaryl group (preferably having 4 to 12 carbon atoms), Alkoxy group (preferably having 1 to 8 carbon atoms), aryloxy group (preferably having 6 to 30 carbon atoms), amino group (preferably having 0 to 24 carbon atoms), silyl group (preferably having 0 to 18 carbon atoms), cyano Represents a group, a nitro group, or a fluorine atom, and these may have the aforementioned substituent Z.
  • R M2 , R M7 , R M8 , R M15 , R M16 and R M23 are preferably a hydrogen atom or an alkyl group or an aryl group which may have a substituent Z, more preferably a hydrogen atom.
  • R M4 , R M5 , R M11 , R M12 , R M19 and R M20 are preferably a hydrogen atom, an alkyl or aryl group which may have a substituent Z, or a fluorine atom, more preferably a hydrogen atom. Is an atom.
  • R M3 , R M6 , R M9 , R M14 , R M17 and R M22 are preferably a hydrogen atom, an alkyl or aryl group optionally having substituent Z, a fluorine atom, or a cyano group, and more A hydrogen atom or an alkyl group which may have a substituent Z is preferable, and a hydrogen atom is more preferable.
  • R M10 , R M13 , R M18 and R M21 are preferably a hydrogen atom, an alkyl group optionally having a substituent Z, an aryl group, a heteroaryl group or an amino group, a nitro group, a fluorine atom, or a cyano group.
  • a hydrogen atom an alkyl or aryl group optionally having a substituent Z, a nitro group, a fluorine atom, or a cyano group, still more preferably a hydrogen atom or a substituent Z.
  • It is an alkyl group that may be present.
  • the substituent is preferably a fluorine atom
  • the alkyl group which may have the substituent Z preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms. is there.
  • Another preferred embodiment of the compound represented by the general formula (M-1) is a case represented by the following general formula (M-3).
  • R S1 to R S5 are each independently an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO 2 R, — C (O) R, —NR 2 , —NO 2 , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent Z.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • R S1 to R S5 When a plurality of R S1 to R S5 are present, they may be bonded to each other to form a ring, and may further have a substituent Z.
  • a represents an integer of 0 to 4, and when a plurality of R S1 are present, they may be the same or different and may be bonded to each other to form a ring.
  • b to e each independently represent an integer of 0 to 5, and when there are a plurality of R S2 to R S5 , respectively, they may be the same or different, and any two may be bonded to form a ring.
  • q is an integer of 1 to 5, and when q is 2 or more, a plurality of R S1 may be the same or different, and may be bonded to each other to form a ring.
  • the alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z.
  • the alkyl group represented by R S1 to R S5 is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as a methyl group or an ethyl group. , I-propyl group, cyclohexyl group, t-butyl group and the like.
  • the cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z.
  • the cycloalkyl group represented by R S1 to R S5 is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total, such as a cyclopentyl group or cyclohexyl group. Groups and the like.
  • the alkenyl group represented by R S1 to R S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • vinyl, allyl, 1-propenyl Examples include 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
  • the alkynyl group represented by R S1 to R S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • Examples of the perfluoroalkyl group represented by R S1 to R S5 include those in which all the hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.
  • the aryl group represented by R S1 to R S5 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, a biphenyl group, and a terphenyl group.
  • the heteroaryl group represented by R S1 to R S5 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted heteroaryl group,
  • R S1 to R S5 are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group, or a heteroaryl group, and more preferably a hydrogen atom, an alkyl group Group, cyano group, trifluoromethyl group, fluoro group and aryl group, more preferably a hydrogen atom, an alkyl group and an aryl group.
  • substituent Z an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom and an alkyl group are more preferable.
  • R S1 to R S5 may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl;
  • the 7-membered ring may further have a substituent Z.
  • the definition and preferred range of cycloalkyl, aryl, and heteroaryl formed are the same as the cycloalkyl group, aryl group, and heteroaryl group defined by R S1 to R S5 .
  • the compound represented by the general formula (M-1) is preferably contained in an amount of 50 to 100% by mass.
  • the content is preferably 80 to 100% by mass, and particularly preferably 95 to 100% by mass.
  • each layer contains the above-mentioned range.
  • the compound represented by the general formula (M-1) may contain only one kind in any organic layer, and a plurality of compounds represented by the general formula (M-1) You may contain combining in a ratio.
  • the thickness of the hole transport layer containing the compound represented by the general formula (M-1) is preferably 1 nm to 500 nm, more preferably 3 nm to 200 nm, and 5 nm to 100 nm. Is more preferable.
  • the hole transport layer is preferably provided in contact with the light emitting layer.
  • the lowest excited triplet (T 1 ) energy in the film state of the compound represented by the general formula (M-1) is 1.77 eV (40 kcal / mol) or more and 3.51 eV (81 kcal / mol) or less. Is preferably 2.39 eV (55 kcal / mol) or more and 3.25 eV (75 kcal / mol) or less.
  • T 1 energy of the compound represented by the general formula (M-1) is higher than the T 1 energy of the phosphorescent material. .
  • the T 1 energy is 2.39 eV (55 kcal / mol) or more and 2.82 eV (65 kcal / mol) from the viewpoint of emission efficiency. mol) or less.
  • the hydrogen atom constituting the general formula (M-1) includes a hydrogen isotope (such as deuterium atom).
  • a hydrogen isotope such as deuterium atom.
  • all hydrogen atoms in the compound may be replaced with hydrogen isotopes, or a mixture in which a part is a compound containing hydrogen isotopes may be used.
  • the compound represented by the general formula (M-1) can be synthesized by combining various known synthesis methods.
  • carbazole compounds are synthesized by dehydroaromatization after the Athercorp rearrangement reaction of a condensate of an aryl hydrazine and a cyclohexane derivative (LF Tieze, by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo).
  • LF Tieze by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo).
  • LF Tieze by Th. Eicher
  • Takano, Ogasawara, Precision organic synthesis page 339 (published by Nankodo).
  • Tetrahedron Letters 39: 617 (1998), 39: 2367 (1998) and 40: 6393 (1999) and the like Tetrahedron Letters 39: 617 (1998), 39: 2367 (1998) and 40
  • the compound represented by the general formula (M-1) is preferably formed into a thin layer by a vacuum deposition process, but a wet process such as solution coating can also be suitably used.
  • the molecular weight of the compound is preferably 2000 or less, more preferably 1200 or less, and particularly preferably 800 or less from the viewpoints of deposition suitability and solubility. Also, from the viewpoint of vapor deposition suitability, if the molecular weight is too small, the vapor pressure becomes small, the change from the gas phase to the solid phase does not occur, and it is difficult to form an organic layer. Particularly preferred.
  • the electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.
  • the electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
  • the electron transport material the compound represented by the general formula (1) can be used.
  • electron transport materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane.
  • anthrone derivatives diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic ring tetracarboxylic anhydrides such as naphthalene and perylene, phthalocyanine derivatives, 8-quinolinol derivatives Represented by metal complexes, metal phthalocyanines, various metal complexes represented by metal complexes with benzoxazole and benzothiazole ligands, and siloles Organosilane derivatives, a layer containing such is preferable.
  • the thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
  • the thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the thickness of the electron injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm, and even more preferably from 0.5 nm to 50 nm.
  • the electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the electron injection layer preferably contains an electron donating dopant.
  • an electron donating dopant may be any organic material or inorganic material as long as it can give electrons to the doped material and generate radical anions.
  • TTF tetrathiafulvalene
  • TTT Dithiaimidazole compounds
  • TTT tetrathianaphthacene
  • bis- [1,3 diethyl-2-methyl-1,2-dihydrobenzimidazolyl] lithium, cesium and the like.
  • the electron donating dopant in the electron injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the electron injection layer. More preferably, the content is 0.5 to 30% by mass.
  • the hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side.
  • a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
  • the T 1 energy in the film state of the organic compound constituting the hole blocking layer is higher than the T 1 energy of the light emitting material in order to prevent energy transfer of excitons generated in the light emitting layer and not to reduce the light emission efficiency. It is preferable.
  • the organic compound constituting the hole blocking layer the compound represented by the general formula (1) can be used.
  • Examples of other organic compounds constituting the hole blocking layer other than the compound represented by the general formula (1) include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate ( Aluminum complexes such as aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as Balq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( Phenanthroline derivatives such as 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)) and the like.
  • BCP 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline
  • the hole blocking layer is not limited to the function of actually blocking holes, and the exciton of the light emitting layer may not diffuse into the electron transport layer, or may have a function of blocking energy transfer quenching. .
  • the compound of the present invention can also be preferably applied as a hole blocking layer.
  • the thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.
  • the organic electroluminescent element of the present invention is preferably disposed between the (B) cathode and the light emitting layer.
  • a material particularly preferably used for the material of the organic layer a compound represented by the general formula (1), an aromatic hydrocarbon compound (particularly, the following general formula (Tp-1)) and a general formula (O— The compound represented by 1) can be mentioned.
  • Tp-1 an aromatic hydrocarbon compound
  • O— The compound represented by 1 can be mentioned.
  • the aromatic hydrocarbon compound and the compound represented by the general formula (O-1) will be described.
  • the aromatic hydrocarbon compound is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the cathode, but its use is not limited, and any layer in the organic layer may be included. Further, it may be contained.
  • the introduction layer of the aromatic hydrocarbon compound is contained in one or more of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block layer. be able to.
  • the organic layer adjacent to the light emitting layer between the light emitting layer and the cathode and containing the aromatic hydrocarbon compound is preferably a charge blocking layer or an electron transport layer, and more preferably an electron transport layer.
  • the aromatic hydrocarbon compound preferably comprises only carbon atoms and hydrogen atoms from the viewpoint of ease of synthesis.
  • the aromatic hydrocarbon compound is contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, more preferably 85 to 100% by mass.
  • the aromatic hydrocarbon compound is contained in the light emitting layer, it is preferably contained in an amount of 0.1 to 99% by weight, more preferably 1 to 95% by weight, based on the total weight of the light emitting layer. It is more preferable to include the mass%.
  • the aromatic hydrocarbon compound it is preferable to use a hydrocarbon compound having only a carbon atom and a hydrogen atom, a molecular weight in the range of 400 to 1200, and a condensed polycyclic skeleton having a total carbon number of 13 to 22.
  • the condensed polycyclic skeleton having 13 to 22 carbon atoms is preferably any one of fluorene, anthracene, phenanthrene, tetracene, chrysene, pentacene, pyrene, perylene, and triphenylene. From the viewpoint of T 1 , fluorene, triphenylene, phenanthrene. Is more preferable, and triphenylene is more preferable from the viewpoint of stability of the compound and charge injection / transport properties, and a compound represented by the following general formula (Tp-1) is particularly preferable.
  • the hydrocarbon compound represented by the general formula (Tp-1) preferably has a molecular weight in the range of 400 to 1200, more preferably 400 to 1000, and still more preferably 400 to 800. If the molecular weight is 400 or more, a high-quality amorphous thin film can be formed, and if the molecular weight is 1200 or less, it is preferable in terms of solubility in a solvent, sublimation, and appropriate deposition.
  • hydrocarbon compound represented by the general formula (Tp-1) is not limited, and the hydrocarbon compound may be further contained not only in the organic layer adjacent to the light emitting layer but also in any layer in the organic layer. .
  • R 12 to R 23 are each independently a hydrogen atom, an alkyl group or an alkyl group, a phenyl group optionally substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, A fluorenyl group, a naphthyl group, or a triphenylenyl group is represented.
  • R 12 to R 23 are not all hydrogen atoms.
  • Examples of the alkyl group represented by R 12 to R 23 are substituted or unsubstituted, for example, methyl group, ethyl group, isopropyl group, n-butyl group, tert-butyl group, n-octyl group, n-decyl group, and an n-hexadecyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, and the like, preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, and a cyclohexyl group, more preferably a methyl group, an ethyl group, or A tert-butyl group.
  • R 12 to R 23 are preferably an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (these are further an alkyl group, a phenyl group, a fluorenyl group). More preferably a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, which may be substituted with a group, a naphthyl group, or a triphenylenyl group.
  • a benzene ring that may be substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (which may be further substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group); It is particularly preferred.
  • the total number of aryl rings is preferably 2 to 8, and preferably 3 to 5. By setting it as this range, a high-quality amorphous thin film can be formed, and solubility in a solvent, sublimation, and deposition suitability are improved.
  • R 12 to R 23 each independently preferably has a total carbon number of 20 to 50, and more preferably a total carbon number of 20 to 36. By setting it as this range, a high-quality amorphous thin film can be formed, and solubility in a solvent, sublimation, and deposition suitability are improved.
  • the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-2).
  • a plurality of Ar 1 are the same, and a phenyl group, a fluorenyl group, a naphthyl group, or a group that may be substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, or Represents a triphenylenyl group.
  • An alkyl group and an alkyl group represented by Ar 1 , a phenyl group, a fluorenyl group, a naphthyl group, or a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group that may be substituted with a triphenylenyl group include R 12 to R 23 It is synonymous with what was mentioned, and a preferable thing is also the same.
  • the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-3).
  • L is a phenyl group, a fluorenyl group, a naphthyl group, a triphenylenyl group, or a combination thereof, which may be substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group.
  • An n-valent linking group is represented. n represents an integer of 1 to 6.
  • the alkyl group, phenyl group, fluorenyl group, naphthyl group, or triphenylenyl group forming the n-valent linking group represented by L has the same meaning as that described for R 12 to R 23 .
  • L is preferably an alkyl group or an n-valent linking group formed by combining a benzene ring, a fluorene ring, or a combination thereof, which may be substituted with a benzene ring.
  • L is bonded to the triphenylene ring by *.
  • N is preferably 1 to 5, and more preferably 1 to 4.
  • the hydrocarbon compound represented by the general formula (Tp-1) When the hydrocarbon compound represented by the general formula (Tp-1)) is used as a host material of a light emitting layer of an organic electroluminescence device or a charge transport material of a layer adjacent to the light emitting layer, the hydrocarbon compound in a thinner state than the light emitting material.
  • the energy gap low emission triplet (T 1 ) energy in a thin film state when the light emitting material is a phosphorescent light emitting material
  • the energy gap and T 1 energy are not too large.
  • the T 1 energy in the film state of the hydrocarbon compound represented by the general formula (Tp-1) is preferably 1.77 eV (40 kcal / mol) or more and 3.51 eV (81 kcal / mol) or less. It is more preferable that it is 39 eV (55 kcal / mol) or more and 3.25 eV (75 kcal / mol) or less.
  • the organic electroluminescent element of the present invention it is preferable from the viewpoint of luminous efficiency that the T 1 energy of the compound represented by the general formula (Tp-1) is higher than the T 1 energy of the phosphorescent material. .
  • the T 1 energy is 2.39 eV (55 kcal / mol) or more and 2.82 eV (65 kcal / mol) from the viewpoint of emission efficiency. mol) or less.
  • T 1 energy of the hydrocarbon compound represented by the general formula (Tp-1) can be obtained by a method similar to the method in the description of the general formula (1).
  • the glass transition temperature (Tg) of the hydrocarbon compound according to the present invention is 80 ° C. or more and 400 ° C. or less from the viewpoint of stably operating the organic electroluminescence device against heat generated during high temperature driving or during device driving. Preferably, it is 100 degreeC or more and 400 degrees C or less, More preferably, it is 120 degreeC or more and 400 degrees C or less.
  • the compounds exemplified as the hydrocarbon compound represented by the general formula (Tp-1) include WO05 / 013388 pamphlet, WO06 / 130598 pamphlet, WO09 / 021107 pamphlet, US2009 / 0009065, WO09 / 008311 pamphlet and WO04 / 018587 pamphlet.
  • R O1 represents an alkyl group, an aryl group, or a heteroaryl group.
  • a O1 to A O4 each independently represent C—R A or a nitrogen atom.
  • R A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R A may be the same or different.
  • L O1 represents a divalent to hexavalent linking group composed of an aryl ring or a heteroaryl ring.
  • n O1 represents an integer of 2 to 6.
  • R O1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). You may have the group A.
  • R O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group.
  • a preferable substituent when the aryl group of R O1 has a substituent includes an alkyl group, an aryl group or a cyano group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group.
  • the aryl group of R O1 When the aryl group of R O1 has a plurality of substituents, the plurality of substituents may be bonded to each other to form a 5- or 6-membered ring.
  • the aryl group of R O1 is preferably a phenyl group which may have a substituent A, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, and even more preferably an unsubstituted group.
  • a O1 to A O4 each independently represent C—R A or a nitrogen atom.
  • 0 to 2 are preferably nitrogen atoms, more preferably 0 or 1 is a nitrogen atom.
  • all of A O1 ⁇ A O4 is C-R A, or A O1 be a nitrogen atom, is preferably A O2 ⁇ A O4 is C-R A, A O1 be a nitrogen atom, A O2 ⁇ More preferably, A O4 is C—R A , A O1 is a nitrogen atom, A O2 to A O4 are C—R A , and R A is all hydrogen atoms.
  • R A represents a hydrogen atom, an alkyl group (preferably having a carbon number of 1 to 8), an aryl group (preferably having a carbon number of 6 to 30), or a heteroaryl group (preferably having a carbon number of 4 to 12). It may have a substituent Z ′.
  • the plurality of R A may be the same or different.
  • R A is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.
  • L O1 represents a divalent to hexavalent linking group consisting of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms).
  • L O1 is preferably an arylene group, heteroarylene group, aryltriyl group, or heteroaryltriyl group, more preferably a phenylene group, a biphenylene group, or a benzenetriyl group, still more preferably a biphenylene group, Or it is a benzenetriyl group.
  • L O1 may have the above-described substituent Z ′, and when it has a substituent, the substituent is preferably an alkyl group, an aryl group, or a cyano group. Specific examples of L O1 include the following.
  • n O1 represents an integer of 2 to 6, preferably an integer of 2 to 4, more preferably 2 or 3. n O1 is most preferably 3 from the viewpoint of the efficiency of the organic electroluminescent element, and most preferably 2 from the viewpoint of the durability of the organic electroluminescent element.
  • the compound represented by the general formula (O-1) is more preferably a compound represented by the following general formula (O-2).
  • R O1 each independently represents an alkyl group, an aryl group, or a heteroaryl group.
  • R O2 to R O4 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.
  • a O1 to A O4 each independently represent C—R A or a nitrogen atom.
  • R A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R A may be the same or different.
  • R O1 and A O1 ⁇ A O4 the general formula (O1) in the same meaning as R O1 and A O1 ⁇ A O4 of, also the same preferable ranges thereof.
  • R 02 to R 04 are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). These may have the substituent group A described above.
  • R 02 to R 04 are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an aryl group, and most preferably a hydrogen atom.
  • the compound represented by the general formula (O-1) has a glass transition temperature (Tg) of 100 ° C. from the viewpoint of stable operation at high temperature storage, stable operation against high temperature driving, and heat generation during driving. It is preferably from ⁇ 400 ° C., more preferably from 120 ° C. to 400 ° C., still more preferably from 140 ° C. to 400 ° C.
  • the compound represented by the general formula (O-1) can be synthesized by the method described in JP-A No. 2001-335776. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.
  • the compound represented by the general formula (O-1) is preferably contained in the organic layer between the light emitting layer and the cathode, but the cathode side layer adjacent to the light emitting layer is used. It is more preferable that it is contained.
  • the entire organic electroluminescent element may be protected by a protective layer.
  • the protective layer the matters described in JP-A-2008-270736, paragraphs [0169] to [0170] can be applied to the present invention.
  • the material for the protective layer may be inorganic or organic.
  • the organic electroluminescent element of the present invention may be sealed entirely using a sealing container.
  • the sealing container the matters described in paragraph [0171] of JP-A-2008-270736 can be applied to the present invention.
  • the organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode.
  • a direct current which may include an alternating current component as necessary
  • the driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-290080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-2441047.
  • the driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.
  • the external quantum efficiency of the organic electroluminescent device of the present invention is preferably 7% or more, and more preferably 10% or more.
  • the value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency in the vicinity of 300 to 400 cd / m 2 when the device is driven at 20 ° C. Can do.
  • the internal quantum efficiency of the organic electroluminescence device of the present invention is preferably 30% or more, more preferably 50% or more, and further preferably 70% or more.
  • the internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a normal organic EL element, the light extraction efficiency is about 20%.
  • the organic electroluminescent element of this invention has an emission peak wavelength of 490 to 580 nm, taking into consideration the lowest excited triplet (T 1 ) energy of the compound represented by the general formula (1).
  • the organic electroluminescence device of the present invention when the compound represented by the general formula (1) is used as a host material for the light emitting layer, an electron transport layer or an electron transport material for the hole blocking layer, light emission
  • the peak wavelength is preferably 490 to 580 nm, more preferably 490 to 550 nm, and particularly preferably 500 to 535 nm.
  • the organic electroluminescent element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication.
  • a device that is driven in a region where light emission luminance is high such as a light emitting device, a lighting device, and a display device.
  • the light emitting device of the present invention includes the organic electroluminescent element of the present invention.
  • the light emitting device of the present invention will be described with reference to FIG.
  • FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
  • the light emitting device 20 in FIG. 2 includes a transparent substrate (support substrate) 2, an organic electroluminescent element 10, a sealing container 16, and the like.
  • the organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2.
  • a protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween.
  • a part of each electrode 3 and 9, a partition, an insulating layer, etc. are abbreviate
  • the adhesive layer 14 a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.
  • the use of the light-emitting device of the present invention is not particularly limited, and for example, it can be a display device such as a television, a personal computer, a mobile phone, and electronic paper in addition to a lighting device.
  • FIG. 3 is a cross-sectional view schematically showing an example of the illumination device of the present invention.
  • the illumination device 40 of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
  • the light scattering member 30 is not particularly limited as long as it can scatter light.
  • the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31.
  • a glass substrate can be preferably cited.
  • the fine particles 32 transparent resin fine particles can be preferably exemplified.
  • the glass substrate and the transparent resin fine particles known ones can be used. In such an illuminating device 40, when light emitted from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30, the incident light is scattered by the light scattering member 30, and the scattered light is emitted from the light emitting surface 30B. It is emitted as illumination light.
  • the display device of the present invention includes the organic electroluminescent element of the present invention.
  • Examples of the display device of the present invention include a display device such as a television, a personal computer, a mobile phone, and electronic paper.
  • Compound 1B-2 was synthesized by repeating Suzuki-Miyaura coupling.
  • the compound represented by the general formula (1) used in the preparation of the organic electroluminescence device described later and the comparative compounds 1 to 4 having a part of the structure similar to them are the same as the compound 1B-2. And synthesized.
  • First layer LG101: film thickness 10 nm
  • Second layer NPD: film thickness 30 nm
  • Third layer Comparative compound 1 (host material) and green phosphorescent material GD-1 (guest material) (mass ratio 90:10): film thickness 30 nm
  • Fourth layer TpH-17: film thickness 10 nm
  • Comparative Example 1 except that the compound represented by the general formula (1) shown in Table 1 below or Comparative Compounds 2 to 4 shown in Table 1 below was used in place of Comparative Compound 1 as the material for the third layer of the organic layer in Comparative Example 1.
  • organic electroluminescent elements of Examples A1 to A9 and Comparative Examples 2 to 4 were obtained.
  • Comparative compound 1 is compound compound 2S described in International Publication WO2009 / 073245
  • Comparative Compound 3 is compound compound 2S described in International Publication WO2009 / 021126
  • Comparative Compound 4 is International Publication WO2009 / Compound compound 9S described in No. 021126.
  • the organic electroluminescent device of each Example using the compound represented by the general formula (1) of Examples A1 to A9 as the host compound of the light emitting layer is durable and has a color after storage at high temperature. It was found that the degree deviation was good.
  • the compounds represented by the general formula (1) of Examples A1 to A9 had a high glass transition temperature and were good.
  • the organic electroluminescent elements of Comparative Examples 1, 2, and 4 were those using Comparative Compounds 1, 2, and 4 as the host compound of the light emitting layer, and were found to have poor durability.
  • the organic electroluminescent element of Comparative Example 3 was obtained by using Comparative Compound 3 as the host compound of the light emitting layer, and it was found that the chromaticity shift after high temperature storage was poor. Further, Comparative Compounds 1 to 3 used in Comparative Examples 1 to 3 had a low glass transition temperature. Note that the emission peak wavelengths of the organic electroluminescent elements prepared in Examples A1 to A9 were 515 to 535 nm.
  • First layer LG101: film thickness 10 nm
  • Second layer HTL-1: film thickness 30 nm
  • Third layer Comparative compound 1 (host material) and green phosphorescent material GD-2 (guest material) (mass ratio 90:10): film thickness 30 nm
  • Fourth layer TpH-17: film thickness 10 nm
  • Examples B1 to B4, Comparative Example 6 In Comparative Example 5, the same procedure as in Comparative Example 5 was performed except that the compound represented by the general formula (1) and the comparative compound 3 were used in place of the comparative compound 1 as the material of the third layer of the organic layer. Organic electroluminescent elements of Examples B1 to B4 and Comparative Example 6 were obtained. The organic electroluminescent elements of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. The durability when the organic electroluminescence device of Comparative Example 5 was used as a durability evaluation standard was set to 100, and the relative values of the durability of the organic electroluminescence devices of other Examples and Comparative Examples were less than 100. The product was evaluated as x, 100 or more and less than 150 as ⁇ , and 150 or more as ⁇ . The results are shown in Table 2 below.
  • the organic electroluminescent devices of the respective examples using the compounds represented by the general formula (1) of Examples B1 to B6 as the host compounds of the light emitting layer are all durable and the color after high temperature storage. It was found that the degree deviation was good.
  • the organic electroluminescent element of Comparative Example 5 was obtained by using Comparative Compound 1 as the host compound of the light emitting layer, and was found to have poor durability.
  • the organic electroluminescent element of Comparative Example 6 uses Comparative Compound 3 as the host compound of the light emitting layer, and it was found that the chromaticity shift after storage at high temperature was poor. Note that the emission wavelength of the organic electroluminescent devices prepared in Examples B1 to B6 was 510 to 525 nm.
  • First layer GD-1: Film thickness 10 nm
  • Second layer NPD: film thickness 30 nm
  • Third layer Comparative compound 1 (host material) and red phosphorescent material RD-1 (guest material) (mass ratio 90:10): film thickness 30 nm
  • Fourth layer Alq: film thickness 10 nm
  • Fifth layer Alq: film thickness 40 nm
  • Examples C1 to C3, Comparative Example 8 In the same manner as in Comparative Example 7, except that the compound represented by the general formula (1) and the comparative compound 3 were used in place of the comparative compound 1 as the material for the third layer of the organic layer in the comparative example 7.
  • Organic electroluminescent elements of Examples C1 to C6 and Comparative Example 8 were obtained.
  • the organic electroluminescent elements of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1.
  • the durability when the organic electroluminescent element of Comparative Example 7 was used as a durability evaluation standard was set to 100, and the relative values of the durability of the organic electroluminescent elements of other Examples and Comparative Examples were less than 100.
  • the product was evaluated as x, 100 or more and less than 150 as ⁇ , and 150 or more as ⁇ . The results are shown in Table 3 below.
  • the organic electroluminescent devices of the respective examples using the compounds represented by the general formula (1) of Examples C1 to C3 as the host compounds of the light emitting layer are all durable and the color after high temperature storage. It was found that the degree deviation was good.
  • the organic electroluminescent element of Comparative Example 7 was obtained by using Comparative Compound 1 as the host compound of the light emitting layer, and was found to have poor durability.
  • the organic electroluminescent element of Comparative Example 8 was obtained by using Comparative Compound 3 as the host compound of the light emitting layer, and it was found that the chromaticity shift after high temperature storage was poor. Note that the emission wavelengths of the organic electroluminescent elements prepared in Examples C1 to C3 were 615 to 630 nm.
  • First layer LG101: film thickness 10 nm
  • Second layer HTL-1: film thickness 30 nm
  • Third layer Comparative compound 1 (host material) and green phosphorescent material GD-2 (guest material) (mass ratio 90:10): film thickness 30 nm
  • Fourth layer OM-8: film thickness 10 nm 5th layer: OM-8: film thickness 40 nm
  • Examples D1 to D5, Comparative Example 10 In the same manner as in Comparative Example 9, except that the compound represented by the general formula (1) and the comparative compound 3 were used in place of the comparative compound 1 as the material of the third layer of the organic layer in the comparative example 9.
  • Organic electroluminescent elements of Examples D1 to D5 and Comparative Example 10 were obtained. These elements were evaluated in the same manner as in Comparative Example 1.
  • the organic electroluminescent elements in these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1.
  • the durability when the organic electroluminescent element of Comparative Example 9 was used as an evaluation criterion for durability was set to 100, and the relative values of the durability of the organic electroluminescent elements of other Examples and Comparative Examples were less than 100.
  • the product was evaluated as x, 100 or more and less than 150 as ⁇ , and 150 or more as ⁇ . The results are shown in Table 4 below.
  • the organic electroluminescent elements of each Example using the compounds represented by the general formula (1) of Examples D1 to D5 as the host compound of the light emitting layer are all durable and the color after high temperature storage. It was found that the degree deviation was good.
  • the organic electroluminescent element of Comparative Example 9 was obtained by using Comparative Compound 1 as the host compound of the light emitting layer, and was found to have poor durability.
  • the organic electroluminescent element of Comparative Example 10 uses Comparative Compound 3 as the host compound of the light emitting layer, and it was found that the chromaticity shift after high temperature storage was poor. Note that the emission wavelengths of the organic electroluminescent elements prepared in Examples D1 to D5 were 510 to 525 nm.
  • Second layer HTL-1: film thickness 30 nm
  • Third layer Comparative compound 1 (host material) and green phosphorescent material GD-2 (guest material) (mass ratio 90:10): film thickness 30 nm
  • Fourth layer Comparative compound 1: film thickness 10 nm 5th layer: OM-8: film thickness 40 nm
  • Examples E1 to E3, Comparative Example 12 In Comparative Example 11, the compound represented by the general formula (1) or the comparative compound 3 is used instead of the comparative compound 1 as the material of the third layer of the organic layer, and the comparative compound 1 is used as the material of the fourth layer of the organic layer.
  • Organic electroluminescent elements of Examples E1 to E3 and Comparative Example 12 were obtained in the same manner as Comparative Example 11 except that the compound represented by the general formula (1) or the comparative compound 3 was used instead of The organic electroluminescent elements of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1.
  • the durability when the organic electroluminescent element of Comparative Example 11 was used as a durability evaluation standard was set to 100, and the relative values of the durability of the organic electroluminescent elements of other Examples and Comparative Examples were less than 100.
  • the product was evaluated as x, 100 or more and less than 150 as ⁇ , and 150 or more as ⁇ . The results are shown in Table 5 below.
  • the organic electroluminescent devices of the respective examples using the compounds represented by the general formula (1) of Examples E1 to E3 as the host compound of the light emitting layer and the fourth layer of the organic layer are all durable. It was also found that the chromaticity deviation after storage at high temperature was good.
  • the organic electroluminescent element of Comparative Example 11 was obtained by using Comparative Compound 1 as the host compound of the light emitting layer and the fourth organic layer, and was found to have poor durability.
  • the organic electroluminescent element of Comparative Example 12 uses Comparative Compound 3 as the host compound of the light emitting layer and the fourth layer of the organic layer, and it was found that the chromaticity shift after high temperature storage was poor. Note that the emission wavelengths of the organic electroluminescent elements prepared in Examples E1 to E3 were 510 to 525 nm.

Abstract

L'invention concerne un élément électroluminescent organique qui comprend un substrat, une paire d'électrodes comportant une électrode positive et une électrode négative qui sont disposées sur le substrat, et une couche organique placée entre les électrodes. Ladite couche organique contient un matériau phosphorescent et un composé représenté par la formule. Ledit élément électroluminescent organique possède une excellente durabilité, et la dérive chromatique après stockage à haute température est supprimée. Dans la formule, X101 représente un atome d'oxygène ou de soufre, chacun des R101-R110 représente un atome d'hydrogène ou un substituant (à l'exclusion d'un groupe alkyle et d'un groupe cyano), les fractions R108-R110 peuvent être identiques ou différentes entre elles, et L101 représente une simple liaison ou un groupe arylène.
PCT/JP2012/058350 2011-03-31 2012-03-29 Élément électroluminescent organique, dispositif émetteur de lumière, dispositif d'affichage et dispositif d'éclairage utilisant un élément électroluminescent organique, et composé pour élément électroluminescent organique WO2012133644A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1020207024699A KR102310693B1 (ko) 2011-03-31 2012-03-29 유기 전계 발광 소자, 그리고 그 소자를 사용한 발광 장치, 표시 장치, 조명 장치 및 그 소자용 화합물
KR1020217031578A KR102424152B1 (ko) 2011-03-31 2012-03-29 유기 전계 발광 소자, 그리고 그 소자를 사용한 발광 장치, 표시 장치, 조명 장치 및 그 소자용 화합물
KR1020187030755A KR102034869B1 (ko) 2011-03-31 2012-03-29 유기 전계 발광 소자, 그리고 그 소자를 사용한 발광 장치, 표시 장치, 조명 장치 및 그 소자용 화합물
KR1020137025153A KR101913271B1 (ko) 2011-03-31 2012-03-29 유기 전계 발광 소자, 그리고 그 소자를 사용한 발광 장치, 표시 장치, 조명 장치 및 그 소자용 화합물
KR1020197030349A KR102151116B1 (ko) 2011-03-31 2012-03-29 유기 전계 발광 소자, 그리고 그 소자를 사용한 발광 장치, 표시 장치, 조명 장치 및 그 소자용 화합물

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2011080213 2011-03-31
JP2011-080213 2011-03-31
JP2012-072476 2012-03-27
JP2012072476A JP5984450B2 (ja) 2011-03-31 2012-03-27 有機電界発光素子、並びに、該素子を用いた発光装置、表示装置、照明装置及び該素子用の化合物

Publications (1)

Publication Number Publication Date
WO2012133644A1 true WO2012133644A1 (fr) 2012-10-04

Family

ID=46931346

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/058350 WO2012133644A1 (fr) 2011-03-31 2012-03-29 Élément électroluminescent organique, dispositif émetteur de lumière, dispositif d'affichage et dispositif d'éclairage utilisant un élément électroluminescent organique, et composé pour élément électroluminescent organique

Country Status (3)

Country Link
JP (1) JP5984450B2 (fr)
KR (5) KR102034869B1 (fr)
WO (1) WO2012133644A1 (fr)

Cited By (75)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9190620B2 (en) 2014-03-01 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
EP3056504A1 (fr) 2015-02-16 2016-08-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3061763A1 (fr) 2015-02-27 2016-08-31 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3098229A1 (fr) 2015-05-15 2016-11-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3101021A1 (fr) 2015-06-01 2016-12-07 Universal Display Corporation Materiaux electroluminescents organiques et dispositfs
EP3124488A1 (fr) 2015-07-29 2017-02-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3159350A1 (fr) 2015-09-03 2017-04-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3205658A1 (fr) 2016-02-09 2017-08-16 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3231809A2 (fr) 2016-04-11 2017-10-18 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3261147A1 (fr) 2016-06-20 2017-12-27 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3261146A2 (fr) 2016-06-20 2017-12-27 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3270435A2 (fr) 2016-06-20 2018-01-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3297051A1 (fr) 2016-09-14 2018-03-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3301088A1 (fr) 2016-10-03 2018-04-04 Universal Display Corporation Pyridines condensées et tant que matériaux et dispositifs électroluminescents organiques
EP3305796A1 (fr) 2016-10-07 2018-04-11 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3321258A1 (fr) 2016-11-09 2018-05-16 Universal Display Corporation Complexes d'iridium avec 4-phénylbenzo[g]quinazoline ou 4-(3,5-dimethylphenylbenzo[g]quinazoline à être utilisés en tant que matériaux émetteurs dans le proche infrarouge or infrarouge de lumière dans des oleds
EP3323822A1 (fr) 2016-09-23 2018-05-23 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US9997716B2 (en) 2014-05-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
EP3345914A1 (fr) 2017-01-09 2018-07-11 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3354654A2 (fr) 2016-11-11 2018-08-01 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3381927A1 (fr) 2017-03-29 2018-10-03 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3401318A1 (fr) 2017-05-11 2018-11-14 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US10158085B2 (en) 2013-12-17 2018-12-18 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
EP3418286A1 (fr) 2017-06-23 2018-12-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3444258A2 (fr) 2017-08-10 2019-02-20 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
JP2019057734A (ja) * 2012-08-03 2019-04-11 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器及び照明装置
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
EP3489243A1 (fr) 2017-11-28 2019-05-29 University of Southern California Composés de carbène et dispositifs électroluminescents organiques
EP3492480A2 (fr) 2017-11-29 2019-06-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3492528A1 (fr) 2017-11-30 2019-06-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
EP3613751A1 (fr) 2018-08-22 2020-02-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3690973A1 (fr) 2019-01-30 2020-08-05 University Of Southern California Matériaux et dispositifs électroluminescents organiques
EP3689889A1 (fr) 2019-02-01 2020-08-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US10749113B2 (en) 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
EP3709376A1 (fr) 2019-03-12 2020-09-16 Universal Display Corporation Dispositif d'affichage delo avec triplet émetteur et durée de vie à l'état excité inférieure à 200 ns
EP3715353A1 (fr) 2019-03-26 2020-09-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3750897A1 (fr) 2019-06-10 2020-12-16 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3771717A1 (fr) 2019-07-30 2021-02-03 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3778614A1 (fr) 2019-08-16 2021-02-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US10985329B2 (en) 2013-12-17 2021-04-20 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
EP3816175A1 (fr) 2019-11-04 2021-05-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3823055A1 (fr) 2019-11-14 2021-05-19 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3845545A1 (fr) 2020-01-06 2021-07-07 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3858945A1 (fr) 2020-01-28 2021-08-04 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3937268A1 (fr) 2020-07-10 2022-01-12 Universal Display Corporation Delo plasmoniques et émetteurs à dipôle vertical
EP4001286A1 (fr) 2020-11-24 2022-05-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4001287A1 (fr) 2020-11-24 2022-05-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4016659A1 (fr) 2020-11-16 2022-06-22 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4019526A1 (fr) 2018-01-26 2022-06-29 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4039692A1 (fr) 2021-02-03 2022-08-10 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4053137A1 (fr) 2021-03-05 2022-09-07 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4056578A1 (fr) 2021-03-12 2022-09-14 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4059941A1 (fr) 2021-03-15 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4059915A2 (fr) 2021-02-26 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4060758A2 (fr) 2021-02-26 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4074723A1 (fr) 2021-04-05 2022-10-19 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4075530A1 (fr) 2021-04-14 2022-10-19 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4075531A1 (fr) 2021-04-13 2022-10-19 Universal Display Corporation Delo plasmoniques et émetteurs à dipôle vertical
EP4079743A1 (fr) 2021-04-23 2022-10-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4086266A1 (fr) 2021-04-23 2022-11-09 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US11522140B2 (en) 2015-08-17 2022-12-06 Universal Display Corporation Organic electroluminescent materials and devices
EP4112701A2 (fr) 2021-06-08 2023-01-04 University of Southern California Alignement moléculaire de phosphores homoleptiques d'iridium
EP4151699A1 (fr) 2021-09-17 2023-03-22 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4174054A1 (fr) * 2018-12-28 2023-05-03 Samsung Electronics Co., Ltd. Composé hétérocyclique, composition le comprenant et dispositif électroluminescent organique comprenant le composé hétérocyclique
EP4185086A1 (fr) 2017-07-26 2023-05-24 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
US11697645B2 (en) 2018-12-28 2023-07-11 Samsung Electronics Co., Ltd. Heterocyclic compound, composition including heterocyclic compound, and organic light-emitting device including heterocyclic compound
EP4212539A1 (fr) 2021-12-16 2023-07-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4242285A1 (fr) 2022-03-09 2023-09-13 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4265626A2 (fr) 2022-04-18 2023-10-25 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4282863A1 (fr) 2022-05-24 2023-11-29 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4293001A1 (fr) 2022-06-08 2023-12-20 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4299693A1 (fr) 2022-06-28 2024-01-03 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4326030A1 (fr) 2022-08-17 2024-02-21 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5984450B2 (ja) * 2011-03-31 2016-09-06 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子、並びに、該素子を用いた発光装置、表示装置、照明装置及び該素子用の化合物

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007069569A1 (fr) * 2005-12-15 2007-06-21 Idemitsu Kosan Co., Ltd. Materiau pour element a electroluminescence organique et element electroluminescent organique correspondant
WO2009021126A2 (fr) * 2007-08-08 2009-02-12 Universal Display Corporation Matériaux hybrides à base de thiophène/triphénylène benzo-fusionnés
WO2009085344A2 (fr) * 2007-12-28 2009-07-09 Universal Display Corporation Matériaux contenant du dibenzothiophène dans les diodes électroluminescentes phosphorescentes
JP2011082238A (ja) * 2009-10-05 2011-04-21 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、照明装置及び表示装置
WO2012005361A1 (fr) * 2010-07-09 2012-01-12 富士フイルム株式会社 Elément électroluminescent organique
WO2012015017A1 (fr) * 2010-07-30 2012-02-02 富士フイルム株式会社 Élément électroluminescent organique et matériau d'élément électroluminescent organique ayant une structure de dibenzothiophène ou de dibenzofuranne
WO2012014752A1 (fr) * 2010-07-30 2012-02-02 富士フイルム株式会社 Elément électroluminescent organique et composé associé
WO2012033062A1 (fr) * 2010-09-08 2012-03-15 富士フイルム株式会社 Élément électroluminescent organique et matière pour des éléments électroluminescents organiques ayant une structure de dibenzothiophène ou une structure de dibenzofurane
WO2012033063A1 (fr) * 2010-09-08 2012-03-15 富士フイルム株式会社 Élément et composé électroluminescent organique

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101425423B1 (ko) * 2005-05-30 2014-08-01 시바 홀딩 인크 전계발광 장치
JP4979247B2 (ja) * 2006-03-08 2012-07-18 三井化学株式会社 アントラセン化合物および該化合物を含有する有機電界発光素子
WO2007125714A1 (fr) 2006-04-26 2007-11-08 Idemitsu Kosan Co., Ltd. Dérivé d'amine aromatique, élément électroluminescent organique employant ledit dérivé
WO2009073245A1 (fr) 2007-12-06 2009-06-11 Universal Display Corporation Complexes organométalliques électroluminescents
KR100910150B1 (ko) * 2008-04-02 2009-08-03 (주)그라쎌 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자
KR101551526B1 (ko) * 2009-08-19 2015-09-08 이데미쓰 고산 가부시키가이샤 방향족 아민 유도체 및 그것을 이용한 유기 전기발광 소자
KR101950363B1 (ko) * 2010-10-29 2019-02-20 가부시키가이샤 한도오따이 에네루기 켄큐쇼 페난트렌 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
JP5984450B2 (ja) * 2011-03-31 2016-09-06 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子、並びに、該素子を用いた発光装置、表示装置、照明装置及び該素子用の化合物

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007069569A1 (fr) * 2005-12-15 2007-06-21 Idemitsu Kosan Co., Ltd. Materiau pour element a electroluminescence organique et element electroluminescent organique correspondant
WO2009021126A2 (fr) * 2007-08-08 2009-02-12 Universal Display Corporation Matériaux hybrides à base de thiophène/triphénylène benzo-fusionnés
WO2009085344A2 (fr) * 2007-12-28 2009-07-09 Universal Display Corporation Matériaux contenant du dibenzothiophène dans les diodes électroluminescentes phosphorescentes
JP2011082238A (ja) * 2009-10-05 2011-04-21 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、照明装置及び表示装置
WO2012005361A1 (fr) * 2010-07-09 2012-01-12 富士フイルム株式会社 Elément électroluminescent organique
WO2012015017A1 (fr) * 2010-07-30 2012-02-02 富士フイルム株式会社 Élément électroluminescent organique et matériau d'élément électroluminescent organique ayant une structure de dibenzothiophène ou de dibenzofuranne
WO2012014752A1 (fr) * 2010-07-30 2012-02-02 富士フイルム株式会社 Elément électroluminescent organique et composé associé
WO2012033062A1 (fr) * 2010-09-08 2012-03-15 富士フイルム株式会社 Élément électroluminescent organique et matière pour des éléments électroluminescents organiques ayant une structure de dibenzothiophène ou une structure de dibenzofurane
WO2012033063A1 (fr) * 2010-09-08 2012-03-15 富士フイルム株式会社 Élément et composé électroluminescent organique

Cited By (104)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019057734A (ja) * 2012-08-03 2019-04-11 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器及び照明装置
US10985329B2 (en) 2013-12-17 2021-04-20 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US10158085B2 (en) 2013-12-17 2018-12-18 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US9190620B2 (en) 2014-03-01 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9997716B2 (en) 2014-05-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US11456423B2 (en) 2014-07-09 2022-09-27 Universal Display Corporation Organic electroluminescent materials and devices
US11024811B2 (en) 2014-07-09 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US11957047B2 (en) 2014-07-09 2024-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US11641774B2 (en) 2014-09-29 2023-05-02 Universal Display Corporation Organic electroluminescent materials and devices
US10749113B2 (en) 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US11342510B2 (en) 2014-10-06 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
EP3056504A1 (fr) 2015-02-16 2016-08-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3061763A1 (fr) 2015-02-27 2016-08-31 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3098229A1 (fr) 2015-05-15 2016-11-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3101021A1 (fr) 2015-06-01 2016-12-07 Universal Display Corporation Materiaux electroluminescents organiques et dispositfs
EP3124488A1 (fr) 2015-07-29 2017-02-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
US11522140B2 (en) 2015-08-17 2022-12-06 Universal Display Corporation Organic electroluminescent materials and devices
EP3760635A1 (fr) 2015-09-03 2021-01-06 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3159350A1 (fr) 2015-09-03 2017-04-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3858842A1 (fr) 2016-02-09 2021-08-04 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3205658A1 (fr) 2016-02-09 2017-08-16 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4122941A1 (fr) 2016-04-11 2023-01-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3231809A2 (fr) 2016-04-11 2017-10-18 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3920254A1 (fr) 2016-06-20 2021-12-08 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4349935A2 (fr) 2016-06-20 2024-04-10 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3843171A1 (fr) 2016-06-20 2021-06-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3270435A2 (fr) 2016-06-20 2018-01-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3261146A2 (fr) 2016-06-20 2017-12-27 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3261147A1 (fr) 2016-06-20 2017-12-27 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3758084A1 (fr) 2016-06-20 2020-12-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3297051A1 (fr) 2016-09-14 2018-03-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3323822A1 (fr) 2016-09-23 2018-05-23 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3301088A1 (fr) 2016-10-03 2018-04-04 Universal Display Corporation Pyridines condensées et tant que matériaux et dispositifs électroluminescents organiques
EP3858844A1 (fr) 2016-10-07 2021-08-04 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3305796A1 (fr) 2016-10-07 2018-04-11 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3789379A1 (fr) 2016-11-09 2021-03-10 Universal Display Corporation Complexes d'iridium avec 4-phénylbenzo[g]quinazoline ou 4-(3,5-dimethylphenylbenzo[g]quinazoline à être utilisés en tant que matériaux émetteurs dans le proche infrarouge or infrarouge de lumière dans des oleds
EP3321258A1 (fr) 2016-11-09 2018-05-16 Universal Display Corporation Complexes d'iridium avec 4-phénylbenzo[g]quinazoline ou 4-(3,5-dimethylphenylbenzo[g]quinazoline à être utilisés en tant que matériaux émetteurs dans le proche infrarouge or infrarouge de lumière dans des oleds
EP3354654A2 (fr) 2016-11-11 2018-08-01 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4092036A1 (fr) 2016-11-11 2022-11-23 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3689890A1 (fr) 2017-01-09 2020-08-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3345914A1 (fr) 2017-01-09 2018-07-11 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4212540A1 (fr) 2017-01-09 2023-07-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3985012A1 (fr) 2017-03-29 2022-04-20 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3730506A1 (fr) 2017-03-29 2020-10-28 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3381927A1 (fr) 2017-03-29 2018-10-03 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3401318A1 (fr) 2017-05-11 2018-11-14 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4141010A1 (fr) 2017-05-11 2023-03-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3418286A1 (fr) 2017-06-23 2018-12-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4185086A1 (fr) 2017-07-26 2023-05-24 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3444258A2 (fr) 2017-08-10 2019-02-20 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3783006A1 (fr) 2017-08-10 2021-02-24 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3489243A1 (fr) 2017-11-28 2019-05-29 University of Southern California Composés de carbène et dispositifs électroluminescents organiques
EP3878855A1 (fr) 2017-11-28 2021-09-15 University of Southern California Composés de carbène et dispositifs électroluminescents organiques
EP3492480A2 (fr) 2017-11-29 2019-06-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3492528A1 (fr) 2017-11-30 2019-06-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4019526A1 (fr) 2018-01-26 2022-06-29 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3613751A1 (fr) 2018-08-22 2020-02-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4206210A1 (fr) 2018-08-22 2023-07-05 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
US11697645B2 (en) 2018-12-28 2023-07-11 Samsung Electronics Co., Ltd. Heterocyclic compound, composition including heterocyclic compound, and organic light-emitting device including heterocyclic compound
EP4174054A1 (fr) * 2018-12-28 2023-05-03 Samsung Electronics Co., Ltd. Composé hétérocyclique, composition le comprenant et dispositif électroluminescent organique comprenant le composé hétérocyclique
EP3690973A1 (fr) 2019-01-30 2020-08-05 University Of Southern California Matériaux et dispositifs électroluminescents organiques
EP4301117A2 (fr) 2019-02-01 2024-01-03 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3689889A1 (fr) 2019-02-01 2020-08-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3709376A1 (fr) 2019-03-12 2020-09-16 Universal Display Corporation Dispositif d'affichage delo avec triplet émetteur et durée de vie à l'état excité inférieure à 200 ns
EP3715353A1 (fr) 2019-03-26 2020-09-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4134371A2 (fr) 2019-03-26 2023-02-15 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3750897A1 (fr) 2019-06-10 2020-12-16 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3771717A1 (fr) 2019-07-30 2021-02-03 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4219515A1 (fr) 2019-07-30 2023-08-02 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3778614A1 (fr) 2019-08-16 2021-02-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3816175A1 (fr) 2019-11-04 2021-05-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3823055A1 (fr) 2019-11-14 2021-05-19 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3845545A1 (fr) 2020-01-06 2021-07-07 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4151644A1 (fr) 2020-01-06 2023-03-22 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3858945A1 (fr) 2020-01-28 2021-08-04 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4294157A2 (fr) 2020-01-28 2023-12-20 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3937268A1 (fr) 2020-07-10 2022-01-12 Universal Display Corporation Delo plasmoniques et émetteurs à dipôle vertical
EP4016659A1 (fr) 2020-11-16 2022-06-22 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4001286A1 (fr) 2020-11-24 2022-05-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4329463A2 (fr) 2020-11-24 2024-02-28 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4001287A1 (fr) 2020-11-24 2022-05-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4039692A1 (fr) 2021-02-03 2022-08-10 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4059915A2 (fr) 2021-02-26 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4060758A2 (fr) 2021-02-26 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4053137A1 (fr) 2021-03-05 2022-09-07 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4056578A1 (fr) 2021-03-12 2022-09-14 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4059941A1 (fr) 2021-03-15 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4074723A1 (fr) 2021-04-05 2022-10-19 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4075531A1 (fr) 2021-04-13 2022-10-19 Universal Display Corporation Delo plasmoniques et émetteurs à dipôle vertical
EP4075530A1 (fr) 2021-04-14 2022-10-19 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4086266A1 (fr) 2021-04-23 2022-11-09 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4079743A1 (fr) 2021-04-23 2022-10-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4112701A2 (fr) 2021-06-08 2023-01-04 University of Southern California Alignement moléculaire de phosphores homoleptiques d'iridium
EP4151699A1 (fr) 2021-09-17 2023-03-22 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4212539A1 (fr) 2021-12-16 2023-07-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4242285A1 (fr) 2022-03-09 2023-09-13 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4265626A2 (fr) 2022-04-18 2023-10-25 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4282863A1 (fr) 2022-05-24 2023-11-29 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4293001A1 (fr) 2022-06-08 2023-12-20 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4299693A1 (fr) 2022-06-28 2024-01-03 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4326030A1 (fr) 2022-08-17 2024-02-21 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs

Also Published As

Publication number Publication date
KR102151116B1 (ko) 2020-09-03
KR101913271B1 (ko) 2018-10-30
KR102424152B1 (ko) 2022-07-25
KR20210122322A (ko) 2021-10-08
KR20200104430A (ko) 2020-09-03
JP2012216817A (ja) 2012-11-08
JP5984450B2 (ja) 2016-09-06
KR20140020934A (ko) 2014-02-19
KR20190120429A (ko) 2019-10-23
KR102310693B1 (ko) 2021-10-13
KR102034869B1 (ko) 2019-10-21
KR20180118815A (ko) 2018-10-31

Similar Documents

Publication Publication Date Title
JP5984450B2 (ja) 有機電界発光素子、並びに、該素子を用いた発光装置、表示装置、照明装置及び該素子用の化合物
JP6582018B2 (ja) 有機電界発光素子、有機電界発光素子用材料、並びに、該素子を用いた発光装置、表示装置、照明装置及び該素子に用いられる化合物
JP5735241B2 (ja) 有機電界発光素子及び電荷輸送材料
JP5906114B2 (ja) 電荷輸送材料、有機電界発光素子、発光装置、表示装置および照明装置
JP5814031B2 (ja) 有機電界発光素子、及びジベンゾチオフェン構造又はジベンゾフラン構造を有する有機電界発光素子用材料
KR101985026B1 (ko) 유기 전계 발광 소자, 유기 전계 발광 소자용 재료, 그리고 그 소자를 사용한 발광 장치, 표시 장치, 조명 장치 및 그 소자에 사용되는 화합물
JP6132470B2 (ja) 有機電界発光素子、該素子に用いる化合物および有機電界発光素子用材料、並びに該素子を用いた発光装置、表示装置及び照明装置
JP5814141B2 (ja) 合成法、その合成法を用いて合成された化合物および有機電界発光素子
WO2012133652A1 (fr) Matériau de transport de charge, élément électroluminescent organique, et dispositif d'éclairage, dispositif d'affichage, ou dispositif électroluminescent caractérisés par l'utilisation dudit élément
JP5973762B2 (ja) 電荷輸送材料、有機電界発光素子及び該素子を用いたことを特徴とする発光装置、表示装置または照明装置
JP5658478B2 (ja) 有機電界発光素子、並びにｍ−キンクフェニル構造を有する電荷輸送材料及び化合物
JP5563399B2 (ja) 有機電界発光素子及びｐ−ジシアノベンゼン構造を有する化合物
JP5650961B2 (ja) 有機電界発光素子、及びジベンゾチオフェン構造又はジベンゾフラン構造を有する有機電界発光素子用材料
JP5990385B2 (ja) 化合物、有機電界発光素子用材料、電荷輸送材料、有機電界発光素子
JP6109137B2 (ja) 有機電界発光素子、及びジベンゾチオフェン構造又はジベンゾフラン構造を有する有機電界発光素子用材
JP6109231B2 (ja) 有機電界発光素子及び電荷輸送材料
JP6113136B2 (ja) 有機電界発光素子、並びにｍ−キンクフェニル構造を有する電荷輸送材料及び化合物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12763821

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20137025153

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC - FORM 1205A (10.01.2014)

122 Ep: pct application non-entry in european phase

Ref document number: 12763821

Country of ref document: EP

Kind code of ref document: A1