US20190006598A1 - Novel compound, material for organic electroluminescence device, and organic electroluminescence device - Google Patents

Novel compound, material for organic electroluminescence device, and organic electroluminescence device Download PDF

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US20190006598A1
US20190006598A1 US16/064,411 US201616064411A US2019006598A1 US 20190006598 A1 US20190006598 A1 US 20190006598A1 US 201616064411 A US201616064411 A US 201616064411A US 2019006598 A1 US2019006598 A1 US 2019006598A1
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Takushi Shiomi
Masahiro Kawamura
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Idemitsu Kosan Co Ltd
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Definitions

  • the invention relates to a novel compound, as well as to an organic electroluminescence device and an electronic apparatus using the same.
  • an organic electroluminescence (EL) device is regarded as a promising solid-emitting inexpensive large-area full color display device, and a large number of developments have been conducted so far.
  • an organic EL device comprises an emitting layer and a pair of opposing electrodes that sandwich the emitting layer. When an electrical field is applied between the both electrodes, electrons are injected from the cathode and holes are injected from the anode. Further, these electrons are re-combined with the holes in the emitting layer, create an excited state, and energy is emitted as light when the excited state is returned to the ground state.
  • Patent Document 1 states that a nitrogen-containing heterocyclic derivative that is obtained by bonding of a benzochrysene ring with a nitrogen-containing heterocyclic group through a linker or not through a linker can be used as a material for an organic EL device.
  • Patent Document 2 states that a nitrogen-containing heterocyclic derivative that is obtained by bonding of a benzophenanthrene ring with a nitrogen-containing heterocyclic group through a liner or not through a linker can be used as a material for an organic EL device.
  • An object of the invention is to provide a novel compound that is effective as a material for an organic EL device.
  • Another object of the invention is to provide an organic EL device that can be driven at a lower driving voltage.
  • the following compound, material for an organic EL device, electron-transporting material, organic EL device and electric apparatus can be provided.
  • R 1 to R 14 is a single bond and is bonded with L 1 and the remainder of R 1 to R 14 are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group including 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group including 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group including 8 to 30 carbon atoms that form a ring (hereinafter referred to as “ring carbon atoms”), a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 20 ring carbon atoms, a substituted or unsubstit
  • L 1 is a single bond, a substituted or unsubstituted arylene group including 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroarylene group including 5 to 20 ring atoms;
  • a material for an organic electroluminescence device that comprises the compound according to 1.
  • An electron-transporting material that comprises the compound according to 1.
  • An electronic apparatus provided with the organic electroluminescence device according to 4.
  • a novel compound that is effective as a material for an organic EL device can be provided.
  • FIG. 1 is a schematic view showing the layer structure of organic EL devices fabricated in the Examples and the Comparative Examples.
  • R 1 to R 14 is a single bond and is bonded with L 1 and the remainder of R 1 to R 14 are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group including 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group including 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group including 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 20 ring carbon atoms, a substituted or unsubstituted heteroaryl group including 5 to 20 ring atoms,
  • Ar 1 and Ar 2 are independently a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroaryl group including 5 to 20 ring atoms.
  • Patent Document 1 does not state specific compounds in which a benzochrysene ring is bonded with a triazine ring through or not through a linker.
  • the compound according to one aspect of the invention can lower the driving voltage when used in an organic EL device.
  • R 3 , R 4 , R 7 , R 8 , R 11 , R 12 , R 13 or R 14 be a single bond that is bonded with R 14 is particularly preferable.
  • the compound represented by the formula (1) be a compound represented by the following formula (2):
  • R 1 to R 13 , Ar 1 and Ar 2 are as defined in the formula (1).
  • L 1 is preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted benzophenanthrylene group, a substituted or unsubstituted benzochrysenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted dibenzofuranylene group or a substituted or unsubstituted dibenzothiophenylene
  • the compound represented by the formula (1) be a compound represented by the following formula (3):
  • R 1 to R 13 , Ar 1 and Ar 2 are as defined in the formula (1);
  • L 1 is a single bond or a group selected from the following groups.
  • R is a substituent, and may be bonded to any position of the ring substituted by R;
  • L 1 is more preferably a group selected from the following groups:
  • Ar 1 and Ar 2 be independently selected from the following groups:
  • R is a substituent, and may be bonded to any position of the ring substituted by R;
  • k is an integer of 0 to 5
  • m is an integer of 0 to 4
  • n is an integer of 0 to 3;
  • R a and R b are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group including 1 to 8 carbon atoms, a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroaryl group including 5 to 20 ring atoms; and
  • R c is a substituted or unsubstituted alkyl group including 1 to 8 carbon atoms or a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms.
  • Ar 1 and Ar 2 are preferably a substituted or unsubstituted phenyl group.
  • R 1 to R 13 are preferably a hydrogen atom.
  • the above-mentioned compound can be produced by the method mentioned in the Synthesis Examples. Further, following this reaction, the compound of the invention can be synthesized by using a known alternate reaction or materials suited to an intended product.
  • a hydrogen atom includes isomers differing in number of neutrons, i.e. protium, deuterium and tritium.
  • the number of ring carbon atoms means the number of carbon atoms among atoms constituting a ring of a compound in which atoms are bonded in the form of a ring (for example, a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound or a heterocyclic compound).
  • a substituent When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The same is applied to the “ring carbon atoms” mentioned below, unless otherwise indicated.
  • a benzene ring includes 6 ring carbon atoms
  • a naphthalene ring includes 10 ring carbon atoms
  • a pyridinyl group includes 5 ring carbon atoms
  • a furanyl group includes 4 ring carbon atoms.
  • a benzene ring or a naphthalene ring is substituted by an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms.
  • the number of carbon atoms of the fluorene ring as the substituent is not included in the number of ring carbon atoms.
  • the number of ring atoms means the number of atoms constituting a ring of a compound having a structure in which atoms are bonded in the form of a ring (for example, monocycle, fused ring, ring assembly) (for example, a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound or a heterocyclic compound). It does not include atoms which do not form a ring or atoms contained in a substituent when the ring is substituted by the substituent. The same is applied to the “ring atoms” mentioned below, unless otherwise indicated.
  • a pyridine ring includes 6 ring atoms
  • a quinazoline ring includes 10 ring atoms
  • a furan ring includes 5 ring atoms.
  • Hydrogen atoms respectively bonded with a carbon atom of a pyridine ring or a quinazoline ring or atoms constituting a substituent are not included in the number of ring atoms.
  • a fluorene ring is bonded with a fluorene ring as a substituent (including a spirofluorene ring), for example, the number of atoms of the fluorene ring as a substituent is not included in the number of ring atoms.
  • the “XX to YY carbon atoms” in the “substituted or unsubstituted ZZ group including XX to YY carbon atoms” means the number of carbon atoms when the ZZ group is unsubstituted. The number of carbon atoms of a substituent when the group is substituted is not included.
  • the “XX to YY atoms” in the “substituted or unsubstituted ZZ group including XX to YY atoms” means the number of atoms when the ZZ group is unsubstituted. The number of atoms of a substituent when the group is substituted is not included.
  • the “unsubstituted” in the “substituted or unsubstituted” means bonding of a hydrogen atom, not substitution by the substituent mentioned above.
  • a spirofluorenyl group can be given.
  • the aryl group have 6 to 20 ring carbon atoms, more preferably 6 to 12 ring carbon atoms.
  • a phenyl group, a naphthyl group and a phenanthryl group can be given.
  • arylene group a divalent group that corresponds to the examples of the aryl group can be given.
  • a pyrrolyl group a triazinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridinyl group, an indolyl group, an isoindolyl group, an imidazolyl group, a furyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, an oxazolyl group, an oxadiazolyl group, a furazanyl
  • the ring atoms of the heteroaryl group is preferably 5 to 20, with 5 to 14 being further preferable.
  • a triazinyl group, pyrimidinyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group and a carbazolyl group can be given.
  • heteroarylene group a divalent group corresponding to the examples of the above-mentioned heteroaryl group can be given.
  • halogen atom fluorine, chlorine, bromine, iodine or the like can be given, with a fluorine atom being preferable.
  • alkyl group a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group or the like can be given.
  • the number of carbon atoms of the alkyl group is preferably 1 to 10, with 1 to 6 being further preferable.
  • a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group and a n-hexyl group are preferable.
  • cycloalkyl group a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, a norbornyl group or the like can be given.
  • the number of ring carbon atoms is preferably 3 to 10, more preferably 3 to 8, with 3 to 6 being particularly preferable.
  • alkylsilyl group is a silyl group substituted by one to three alkyl group(s).
  • an alkyl group the above-mentioned examples of an alkyl group can be given.
  • alkylsilyl group a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triisopropylsilyl group or the like can be given.
  • the arylsilyl group is a silyl group substituted by one to three aryl group(s).
  • the examples of the aryl group mentioned above can be given.
  • the arylsilyl group may be substituted by the above-mentioned alkyl group.
  • a triphenylsilyl group, a phenyldimethylsilyl group or the like can be given.
  • the alkoxy group is represented by —OY.
  • Y the examples of the alkyl mentioned above can be given.
  • the alkoxy group is a methoxy group or an ethoxy group, for example.
  • the aryloxy group is represented by —OZ.
  • Z the examples of the aryl group mentioned above can be given.
  • the aryloxy group is a phenoxy group, for example.
  • the alkylthio group is represented by —SY.
  • Y the examples of the alkyl group mentioned above can be given.
  • the arylthio group is represented by —SZ.
  • Z the examples of the aryl group mentioned above can be given.
  • the arylamino group is an amino group substituted by one or two aryl groups.
  • the aryl group the example of the aryl group mentioned above can be given.
  • a cyano group, an amino group, a carboxyl group or the like can be given.
  • a phosphoryl group can be given.
  • the substituent when Ar 1 and Ar 2 are a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms is preferably an alkyl group including 1 to 10 carbon atoms, an aryl group including 6 to 20 ring carbon atoms, a heteroaryl group including 5 to 20 ring atoms excluding a nitrogen-containing heterocylic group, a cyano group, etc.
  • a heteroaryl group including 5 to 20 ring atoms excluding a nitrogen-containing heterocyclic group an oxygen-containing heterocyclic group and a sulfur-containing heterocyclic group can be given, for example.
  • the above-mentioned compound can be used as a material for an organic electroluminescence (EL) device, preferably as an electron-transporting material.
  • EL organic electroluminescence
  • one or more organic thin film layers comprising at least an emitting layer are disposed between a cathode and an anode, and at least one layer of the organic thin film layers comprises the compound represented by the formula (1).
  • the above-mentioned organic EL device preferably has an electron-transporting zone between the emitting layer and the cathode.
  • the electron-transporting zone has one or more organic thin film layers, and at least one layer of the organic thin film layers comprises the compound represented by the formula (1).
  • the at least one layer is preferably an electron-transporting layer.
  • Anode/Emitting layer/Cathode (2) Anode/Hole-transporting zone/Emitting layer/Cathode (3) Anode/Emitting layer/Electron-transporting zone/Cathode (4) Anode/Hole-transporting zone/Emitting layer/Electron-transporting zone/Cathode (“/” means that the layers are adjacently stacked)
  • the electron-transporting zone is normally composed of one or more layers selected from an electron-injecting layer and an electron-transporting layer.
  • the hole-transporting zone is normally composed of one or more layers selected from a hole-injecting layer and a hole-transporting layer.
  • a layer containing the compound represented by the formula (1) be provided in the electron-transporting zone in (3) or (4) mentioned above.
  • the electron-transporting zone further comprise 8-quinolinolato lithium (Liq).
  • Liq may be contained in a layer containing the compound represented by the formula (1) or may be contained in layers in other electron-transporting zone.
  • the electron-transporting zone comprise an electron-injecting layer and at least two electron-transporting layers.
  • the electron-transporting layer that is not adjacent to the electron-injecting layer comprise the above-mentioned compound.
  • the electron-transporting layer that is adjacent to the electron-injecting layer comprises the compound represented by the formula (1)
  • a region from the electron-transporting zone to the cathode in the organic EL device according to one aspect of the invention have the following configuration:
  • the configuration (a) mentioned above is particularly preferable.
  • the substrate is used as a base of an emitting device.
  • glass, quarts, plastic or the like can be used, for example.
  • a flexible substrate may be used.
  • a flexible substrate is a substrate that can be bent.
  • a plastic substrate made of polycarbonate or polyvinyl chloride or the like can be given.
  • a metal for an anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound having a large work function (specifically, 4.0 eV or more), a mixture thereof or the like.
  • ITO Indium Tin Oxide
  • indium oxide-tin oxide containing silicon or silicon oxide indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene or the like can be given, for example.
  • gold (Au), platinum (Pt) or a nitride of a metal material (e.g. titanium nitride) or the like can be given.
  • a hole-injecting layer is a layer that contains a substance having high hole-injection property.
  • a substance having high hole-injection property molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, an aromatic amine compound, or a polymer compound (oligomer, dendrimer, polymer, etc.) or the like can be used.
  • an acceptor compound can be given.
  • the acceptor compound a heterocyclic derivative on which an electron-attracting group is substituted, a quinone derivative on which an electron-attracting group is substituted, an arylborane derivative, a heteroarylborane derivative or the like can be preferably used.
  • hexacyanohexaazatriphenylene, F 4 TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane) or 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl) methylene]cyclopropane or the like can preferably be used.
  • a layer that comprises an acceptor compound may further comprise a matrix material.
  • a matrix material a wide variety of materials for an organic EL device can be used.
  • As the matrix material used together with the acceptor compound it is preferable to use a donor compound. It is further preferable to use an aromatic amine compound.
  • a hole-transporting layer is a layer that contains a substance having high hole-transporting property.
  • aromatic amine compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • the layer containing the substance having high hole-transporting property may be not only a single layer but also a layer obtained by stacking two or more layers containing the above-mentioned substances.
  • the hole-transporting material is preferably a compound represented by the following general formula (H):
  • Q 1 to Q 3 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms or a group composed of a combination of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group.
  • substituents such as a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a spirobifluorenyl group, an indenofluorenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a triphenylenyl group and the like are preferable.
  • the heterocyclic group a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group or the like are preferable.
  • a dibenzofuran-substituted aryl group a dibenzothiophene-substituted aryl group, a carbazole-substituted aryl group and the like are preferable. These substituents may further have a substituent.
  • At least one of Q 1 to Q 3 in the general formula (H) be a compound that is further substituted by an arylamino group. It is also preferred that at least one of Q 1 to Q 3 be a diamine derivative, a triamine derivative or a tetraamine derivative.
  • the diamine derivative tetraaryl-substituted benzidine derivatives and TPTE (4,4′-bis[N-phenyl-N-[4′-diphenylamino-1,1′-biphenyl-4-yl]amino]-1,1′-biphenyl) or the like are preferably used.
  • An emitting layer is a layer that contains a substance having high emitting property, and various materials can be used for the emitting layer.
  • a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as the substance having high emitting property.
  • a fluorescent compound is a compound that can emit light from the singlet excited state
  • a phosphorescent compound is a compound that can emit light from the triplet excited state.
  • blue fluorescent emitting material that can be used in the emitting layer
  • pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives and the like can be given.
  • green fluorescent emitting material that can be used in the emitting layer an aromatic amine derivative and the like can be used.
  • red fluorescent emitting material that can be used in the emitting layer tetracene derivatives, diamine derivatives and the like can be given.
  • a fused polycyclic aromatic derivative, a styrylamine derivative, a fused-ring amine derivative, a boron-containing compound, a pyrrole derivative, an indole derivative, a carbazole derivative and the like are preferable.
  • a fused-ring amine derivative and a boron-containing compound can be given.
  • a fused ring amine derivative is preferably a compound represented by the following general formula (J):
  • Q 4 to Q 7 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group including 5 to 50 ring atoms.
  • aryl group including 6 to 50 ring carbon atoms an aromatic hydrocarbon group including 6 to 12 ring carbon atoms is further preferable, with a phenyl group being particularly preferable.
  • a heteroaryl group including 5 to 50 ring atoms a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group and the like can be given, with a dibenzofuranyl group being preferable.
  • Q 8 is a substituted or unsubstituted divalent aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent aryl group including 5 to 50 ring atoms.
  • divalent aromatic aryl group including 6 to 50 ring carbon atoms a pyrenyl group, a chrysenyl group, an anthracenyl group, a fluorenyl group or the like can be given, with a pyrenyl group being preferable.
  • a fluorenyl group to which one or more benzofuro skeleton(s) is (are) fused is preferable.
  • the boron-containing compound examples include a pyrromethene derivative and a triphenylborane derivative.
  • the derivative as used herein refers to a compound containing said skeleton as a partial structure thereof, and includes a compound further forming a fused ring and a compound forming a ring by substituents.
  • a fused polycyclic aromatic derivative it is a compound containing a fused polycyclic aromatic skeleton as a partial structure thereof, and a compound that further forms a fused ring in the fused polycyclic aromatic skeleton, and a compound that forms a ring by substituents of the fused polycyclic aromatic skeleton.
  • a metal complex such as an iridium complex, an osmium complex and a platinum complex can be given.
  • an iridium complex and the like can be given.
  • a metal complex such as an iridium complex, a platinum complex, a terbium complex and a europium complex can be given.
  • the phosphorescent emitting material that can be used in the emitting layer, and that is an ortho-metalated complex of a metal element selected from iridium, osmium and platinum, is preferably a complex represented by the following formula (K):
  • Q 9 is at least one metal selected from the group consisting of osmium, iridium and platinum, t is the valence of the metal, and u is 1 or more.
  • the ring Q 10 is a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms or a substituted or unsubstituted heteroaryl group including 5 to 30 ring atoms and the ring Q 11 is a substituted or unsubstituted heteroaryl group including 5 to 30 ring atoms that includes a nitrogen atom as an atomic element constituting the heterocycle.
  • Q 12 to Q 14 are independently a hydrogen atom or a substituent.
  • plural rings Q 10 and plural rings Q 11 may be independently the same as or different from each other.
  • plural Q 12 to Q 14 may independently be the same as or different from each other.
  • the emitting layer may have a structure in which the above-mentioned substance having a high emitting property (guest material) is dispersed in other substances (host material).
  • guest material substance having a high emitting property
  • host material substances having a higher lowest unoccupied molecular orbital (LUMO level) than that of the substance having high emitting property, and having a lower highest occupied molecular orbital (HOMO level) than that of the substance having high emitting property.
  • LUMO level lowest unoccupied molecular orbital
  • HOMO level lowest occupied molecular orbital
  • a metal complex such as an aluminum complex, a beryllium complex, a zinc complex or the like
  • a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, a phenanthroline derivative and the like
  • a fused aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, a chrysene derivative and the like
  • an aromatic amine compound such as a triarylamine derivative, a fused polycyclic aromatic amine derivative and the like
  • a compound having a fused polycyclic aromatic derivative as its main skeleton is preferable, with an anthracene derivative, a pyrene derivative, a chrysene derivative, a naphthacene derivative and the like can be given.
  • a host that is particularly preferable as a blue host material (a host material that can be used with a blue fluorescent emitting material) and a green host material (a host material that can be used with a green fluorescent emitting material) is an anthracene derivative that is represented by the following formula (E):
  • Ar x1 and Ar x2 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic group including 5 to 50 ring atoms.
  • Ar x1 and Ar x2 are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group including 5 to 30 ring atoms.
  • Ar x1 and Ar x2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group or a substituted or unsubstituted carbazolyl group.
  • R x1 to R x8 are independently a hydrogen atom or a substituent.
  • a carbazole derivative, a carbazole derivative substituted with carbazole, a carbazole derivative to which a benzo skeleton is fused to form a ring, a carbazole derivative to which an indeno skeleton is fused to form a ring, a carbazole derivative to which an indolo skeleton is fused to form a ring, a carbazole derivative to which a benzofuro skeleton is fused to form a ring, a triazine derivative, a pyrimidine derivative, a quinazoline derivative, a fluoranthene derivative, a triphenylene derivatives are preferable.
  • An electron-transporting layer is a layer containing a substance having high electron-transporting property.
  • a metal complex such as an aluminum complex, a beryllium complex or a zinc complex
  • a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative or a phenanthroline derivative
  • 3) a polymer compound can be used.
  • Materials to be used for the electron-transporting layer are preferably imidazole derivatives (benzimidazole derivatives, imidazopyridine derivatives, and benzimidazophenanthridine derivatives, for example), azine derivatives (pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, and phenanthroline derivatives, for example, and the heterocyclic ring thereof may be substituted with phosphine oxide-based substituents), and aromatic hydrocarbon derivatives (for example, anthracene derivatives and fluoranthene derivatives can be given).
  • imidazole derivatives benzimidazole derivatives, imidazopyridine derivatives, and benzimidazophenanthridine derivatives, for example
  • azine derivatives pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, and phenanthroline derivatives, for example, and the heterocyclic ring thereof may be substituted with
  • the electron-transporting zone comprises two or more electron-transporting layers, and one of the electron-transporting layers comprises the compound according to one embodiment of the invention, and the other of the electron-transporting layers comprises the above-mentioned materials for the electron-transporting layer.
  • one electron-transporting layer comprises both the compound according to one embodiment of the present invention and the above-mentioned materials for the electron-transporting layer. Specific examples of the materials used for the electron-transporting layer are shown below, but the materials are not limited thereto.
  • An alkaline earth metal or a compound of those can be used.
  • 8-quinolinolato lithium (Liq) can be used.
  • the electron-transporting zone further comprise one or more selected from an electron-donating dopant and an organic metal complex.
  • At least one selected from an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a rare earth metal and a rare earth metal compound and the like can be given.
  • organic metal complex at least one selected from an organic metal complex containing an alkali metal, an organic metal complex containing an alkaline earth metal and an organic metal complex containing a rare earth metal can be given.
  • lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work function: 2.16 eV), cesium (Cs) (work function: 1.95 eV) or the like can be given.
  • Ca calcium (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV or more and 2.5 eV or less), barium (Ba) (work function: 2.52 eV) and the like can be given.
  • rare earth metal scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like can be given.
  • alkali oxides such as lithium oxide (Li 2 O), cesium oxide (Cs 2 O) and potassium oxide (K 2 O)
  • alkali halides such as lithium fluoride (LiF), sodium fluoride (NaF), cesium fluoride (CsF), potassium fluoride (KF) or the like
  • lithium fluoride (LiF), lithium oxide (Li 2 O) and sodium fluoride (NaF) are preferable.
  • barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and mixtures thereof such as barium strontium acid (Ba x Sr 1-x O) (0 ⁇ x ⁇ 1) and barium calcium acid (Ba x Ca 1-x O) (0 ⁇ x ⁇ 1) can be given.
  • BaO, SrO and CaO are preferable.
  • ytterbium fluoride As the rare-earth metal compound, ytterbium fluoride (YbF 3 ), scandium fluoride (ScF 3 ), scandium oxide (ScO 3 ), yttrium oxide (Y 2 O 3 ), cerium oxide (Ce 2 O 3 ), gadolinium fluoride (GdF 3 ) and terbium fluoride (TbF 3 ) can be given. Among these, YbF 3 , ScF 3 and TbF 3 are preferable.
  • the organic metal complexes are not particularly limited as long as they each contain, as a metal ion, at least one of alkali metal ions, alkaline-earth metal ions, and rare-earth metal ions, as mentioned above.
  • preferred examples of the ligand include, but are not limited to, quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, hydroxyfluborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof.
  • organic metal complex 8-quinolinolato lithium and the like can be given.
  • the content ratio thereof in the electron-transporting layer is preferably 0.1 to 50 mass %, more preferably 0.1 to 20 mass %, further preferably 1 to 10 mass %, and when the electron-transporting layer contains at least one of an organometallic complex containing an alkali metal and an organometallic complex containing an alkaline earth metal, the content ratio thereof in the electron-transporting layer is 1 to 99 mass %, and more preferably 10 to 90 mass %.
  • a metal having a small work function specifically, 3.8 eV or less
  • an alloy an electrically conductive compound, a mixture of those or the like.
  • an element belonging to Group 1 or Group 2 of the periodic table of the elements i.e., an alkali metal such as lithium (Li) or cesium (Cs), an alkaline earth metal such as magnesium (Mg), alloys containing the alkali metal and the alkaline earth metal (e.g. MgAg, AlLi) and a rare earth metal and an alloy containing the rare earth metal and the like can be given.
  • an alkali metal such as lithium (Li) or cesium (Cs)
  • an alkaline earth metal such as magnesium (Mg)
  • alloys containing the alkali metal and the alkaline earth metal e.g. MgAg, AlLi
  • a rare earth metal and an alloy containing the rare earth metal and the like can be given.
  • the above-mentioned organic EL device can be used in various electronic apparatuses.
  • it can be used in a planar luminous body such as a flat panel display of a wall-hanging TV, a backlight of a copier, a printer and a crystal liquid display, or a light source of instruments, a displaying board, sign lighting or the like.
  • the compound of the invention can be used not only in an organic EL device but also in the field of an electrophotographic photoreceptor, a photoelectric conversion device, a solar cell, an image sensor or the like.
  • a glass substrate with an ITO transparent electrode (anode) having a dimension of 25 mm ⁇ 75 mm ⁇ 1.1 mm in thickness was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then to UV ozone cleaning for 30 minutes.
  • the thickness of the ITO transparent electrode was 130 nm.
  • the cleaned glass substrate with transparent electrode lines was mounted on a substrate holder in a vacuum deposition apparatus.
  • compound HI was deposited on the surface on which the transparent electrode lines had been formed so as to cover the transparent electrode, whereby a 5 nm-thick HI film was formed.
  • the HI film functions as a hole-injecting layer.
  • the following aromatic amine derivative (compound HT-1) was deposited as the first hole-transporting material, whereby a 80 nm-thick first hole-transporting layer was formed.
  • the following aromatic amine derivative (compound HT-2) was deposited as the second hole-transporting material, whereby a 10 nm-thick second hole-transporting layer was formed.
  • the following compound BH as the host material and the following compound BD as the phosphorescent emitting dopant were co-deposited, whereby a 25 nm-thick emitting layer was formed.
  • the concentration of the compound BD in the emitting layer was 4.0 mass %. This co-deposited layer functions as an emitting layer.
  • the following compound A-1 was formed into a 10 nm-thick film.
  • This compound A-1 film functions as a first electron-transporting layer was formed.
  • the following compound ET-1 was deposited, whereby a 15 nm-thick second electron-transporting layer was formed.
  • Metal Al was deposited on this LiF film, whereby a 80 nm-thick metal cathode was formed.
  • the organic EL device of Example 1 has a layer structure shown in FIG. 1 , and each layer has the following configuration.
  • an external quantum efficiency EQE (unit: %) was calculated on the assumption that lambassian radiation was conducted.
  • Organic EL devices were fabricated in the same manner as in Example 1, except that the configurations of the first electron-transporting layer, the second electron-transporting layer and the metal cathode in Example 1 were changed as follows.
  • the driving voltage, the external quantum efficiency (EQE) and the device lifetime (LT95) were measured. The results are shown in Table 2.
  • Compound A-1 Liq(25:50%)/Liq(1 nm)/Al(80)
  • Example 2 A device was fabricated and evaluated in the same manner as in Example 2, except that compound A-1 in Example 2 was changed to compound A-2. The results are shown in Table 2.
  • Compound A-2 Liq (25:50%)/Liq(1 nm)/Al(80)
  • Example 2 A device was fabricated and evaluated in the same manner as in Example 2, except that compound A-1 in Example 2 was changed to comparative compound B-1. The results are shown in Table 2.
  • Compound B-1 Liq(25:50%)/Liq(1 nm)/Al(80)
  • Example 2 Devices were fabricated and evaluated in the same manner as in Example 2, except that compound A-1 in Example 2 was changed to compounds shown in Table 2. The results are shown in Table 2.
  • the compounds used are as follows.
  • the device that comprises the electron-transporting layer containing the compound according to one aspect of the invention and is doped with Liq has a low driving voltage, an improved external quantum efficiency and a significantly prolonged lifetime.

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