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  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
  • C07D471/04—Ortho-condensed systems
• • H—ELECTRICITY
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  • H05B33/00—Electroluminescent light sources
  • H05B33/12—Light sources with substantially two-dimensional [2D] radiating surfaces
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K50/00—Organic light-emitting devices
  • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
  • H10K50/14—Carrier transporting layers
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  • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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  • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
  • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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  • 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
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  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/649—Aromatic compounds comprising a hetero atom
  • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
  • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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  • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

• the present invention relates to a phenanthroline derivative having a specific structure, and an organic EL device, display device and lighting device using the same.
• organic EL elements have been steadily put into practical use, such as being used in TV and smartphone displays.
• existing organic EL devices still have many technical problems. Among them, there are problems in obtaining highly efficient light emission, obtaining a long-life light-emitting element, and obtaining an element excellent in heat resistance.
• phenanthroline derivatives substituted with a specific phosphine oxide group see, for example, Patent Document 1
• phenanthroline derivatives having an amino group see, for example, Patent Document 2
• specific Phenanthroline derivatives having an aryl group see, for example, Patent Document 3
• phenanthroline derivatives having a specific arylene group and a heteroaryl group see, for example, Patent Document 4
• compounds having multiple phenanthrolines see, for example, Patent Document 5
• Patent Documents 1 to 5 phenanthroline derivatives having specific aryl groups or heteroaryl groups make it possible to obtain organic EL devices with excellent light-emitting properties.
• the characteristics required of organic EL devices have been increasing more and more, and there is a demand for techniques for improving luminous efficiency, durability, and heat resistance of materials.
• the object of the present invention is to provide a compound capable of obtaining an organic EL device having excellent heat resistance, luminous efficiency and durable life.
• R 1 to R 6 each independently represent a hydrogen atom or an alkyl group. However, at least two of R 1 to R 6 are alkyl groups.
• X is a hydrogen atom, a substituted or unsubstituted aryl group or heteroaryl group. However, when these groups are substituted, the substituent is an alkyl group.
• Y is a biphenyl group, terphenyl group, quaterphenyl group, or LZ. However, L is a divalent linking group selected from the following, and is bonded at the position of *.
• Z is a substituted or unsubstituted naphthyl group, phenanthryl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, dimethylfluorenyl group, diphenylfluorenyl group, spirobifluorenyl group, pyridyl group, pyrimidyl group, triazinyl group, bipyridyl group, terpyridyl group, quinolinyl group, quinazolyl group, carbazolyl group, carbolinyl group, dibenzofuranyl group, dibenzothiophenyl group or phenanthrolinyl group.
• X is a substituted or unsubstituted aryl group or heteroaryl group
• Y is LZ
• Z is a substituted or unsubstituted phenanthrolinyl group or terpyridyl group
• X is a substituted or unsubstituted aryl group or heteroaryl group
• Y is LZ
• Z is a substituted or unsubstituted phenanthrolinyl group or terpyridyl group
• Y is LZ
• L is a phenylene group.
• [7] The compound according to any one of [1] to [6], wherein at least four of R 1 to R 6 in general formula (1) are alkyl groups.
• X is a phenyl group
• Y is LZ
• Z is a phenanthrolinyl group substituted with a phenyl group or an unsubstituted terpyridyl group, [1 ] to the compound according to any one of [7].
• a light-emitting device having at least an electron-transporting layer and a light-emitting layer between an anode and a cathode and emitting light by electric energy, wherein the electron-transporting layer is the light-emitting device according to any one of [1] to [8].
• An organic EL device containing a compound of [17] A display device comprising the EL device according to any one of [9] to [16].
• the compound of the present invention has excellent durability.
• the compound of the present invention can provide an organic EL device excellent in luminous efficiency and durability.
• a compound that is one embodiment of the present invention has a structure represented by general formula (1).
• R 1 to R 6 each independently represent a hydrogen atom or an alkyl group. However, at least two of R 1 to R 6 are alkyl groups.
• X is a hydrogen atom, a substituted or unsubstituted aryl group or heteroaryl group. However, when these groups are substituted, the substituent is an alkyl group.
• Y is a biphenyl group, terphenyl group, quaterphenyl group, or LZ. However, L is a divalent linking group selected from the following, and is bonded at the position of *.
• Z is a substituted or unsubstituted naphthyl group, phenanthryl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, dimethylfluorenyl group, diphenylfluorenyl group, spirobifluorenyl group, pyridyl group, pyrimidyl group, triazinyl group, bipyridyl group, terpyridyl group, quinolinyl group, quinazolyl group, carbazolyl group, carbolinyl group, dibenzofuranyl group, dibenzothiophenyl group or phenanthrolinyl group.
• the alkyl group is, for example, a saturated aliphatic hydrocarbon group such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, which is a substituent may or may not have
• the hydrogen atom in the alkyl group may be a deuterium atom.
• the number of carbon atoms in the alkyl group is not particularly limited, it is usually in the range of 1 to 20, more preferably 1 to 8 in terms of availability and cost.
• An aryl group is, for example, an aromatic hydrocarbon group such as a phenyl group, a biphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, and a terphenyl group.
• an aromatic hydrocarbon group such as a phenyl group, a biphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, and a terphenyl group.
• the number of carbon atoms in the aryl group is not particularly limited, it is usually in the range of 6 or more and 40 or less.
• the heteroaryl group includes, for example, pyridyl group, furanyl group, thiophenyl group, quinolinyl group, isoquinolinyl group, pyrazinyl group, pyrimidyl group, pyridazinyl group, triazinyl group, napthyridinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, benzocarbazolyl group, carbolinyl group, indolocarbazolyl group, benzoflocarbazolyl group, benzothienocarba Non-carbon groups such as zolyl, dihydroindenocarbazolyl, benzoquinolinyl, acridinyl, dibenzoacridin
• the heteroaryl group Indicates a cyclic aromatic group having one or more atoms in the ring.
• the number of carbon atoms in the heteroaryl group is not particularly limited, it is preferably in the range of 2 to 40, more preferably in the range of 2 to 30.
• Patent Documents 1 to 5 disclose compounds V, W, X, Y, and Z represented by the following formulas.
• having an amino group makes the energy level of the LUMO, which is the electronic conduction level, shallower, lowering the electron transporting ability, increasing the drive voltage of the device, and causing problems in luminous efficiency and durability.
• Compounds having an anthrylene group such as compounds X and Y, tend to generate impurities during vapor deposition, and there has been a demand for improved heat resistance.
• the crystallinity is too high due to the high planarity of the phenanthrolinyl group and the linking group, the drive voltage of the device is increased, and there are problems in luminous efficiency and durability.
• a phenanthrolinyl derivative such as compound Z is likely to react at high temperatures, and further improvement in heat resistance has been desired.
• R 1 to R 6 are each independently a hydrogen atom or an alkyl group, and at least two of R 1 to R 6 are alkyl groups.
• R 1 to R 6 are hydrogen atoms, any one of R 1 to R 6 is likely to react when exposed to high temperature conditions, and impurities tend to be generated.
• the reaction sites are protected and the reactivity is lowered by the steric repulsion of the alkyl groups, thereby suppressing the generation of impurities due to heat and improving the heat resistance.
• at least four of R 1 to R 6 are preferably alkyl groups.
• X is a hydrogen atom, a substituted or unsubstituted aryl group or heteroaryl group.
• X is a substituted or unsubstituted aryl group or heteroaryl group
• the 2- and 9-positions which are one of the reaction sites of phenanthroline, can be substituted, so that the durability life of the organic EL device can be further improved.
• X is a phenyl group
• the high coordinating property of the nitrogen atom on the phenanthrolinyl group results in the formation of a more stable layer with higher metal coordinating property when used in a metal-doped layer. can be done. Therefore, the drive voltage can be further reduced, and the durable life can be further improved.
• the substituent is an alkyl group. These substituents can further improve the heat resistance of the compound and the durability life of the organic EL device without lowering the charge transport property of the compound.
• Y is a biphenyl group, terphenyl group, quaterphenyl group or LZ.
• L is a divalent linking group selected from the following, and is bonded at the position of *.
• Z is a substituted or unsubstituted naphthyl group, phenanthryl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, dimethylfluorenyl group, diphenylfluorenyl group, spirobifluorenyl group, pyridyl group, pyrimidyl group, triazinyl group, bipyridyl group, terpyridyl group, quinolinyl group, quinazolyl group, carbazolyl group, carbolinyl group, dibenzofuranyl group, dibenzothiophenyl group or phenanthrolinyl group.
• Z Metal doping when Z is pyridyl, pyrimidyl, triazinyl, bipyridyl, terpyridyl, quinolinyl, quinazolyl, carbazolyl, carbolinyl, dibenzofuranyl, dibenzothiophenyl, phenanthrolinyl
• Z is a phenyl group-substituted phenanthrolinyl group or terpyridyl group, this effect is further enhanced. is more preferable because The case where L is a phenylene group is also preferable from the viewpoint of increasing the metal coordinating ability.
• substituents for Z include alkyl groups, aryl groups, and heteroaryl groups. Among these, a methyl group and a phenyl group are preferable.
• Y is LZ, and Z is more preferably a substituted or unsubstituted pyridyl group, pyrimidyl group, triazinyl group, bipyridyl group, terpyridyl group or phenanthrolinyl group.
• Y is LZ and Z is an unsubstituted terpyridyl group.
• X is a substituted or unsubstituted aryl group or heteroaryl group
• Y is LZ
• Z is a substituted or unsubstituted phenanthrolinyl group or terpyridyl group. more preferred.
• Y is LZ and L is a phenylene group.
• X is a phenyl group
• Y is LZ
• Z is a phenyl group-substituted phenanthrolinyl group or an unsubstituted terpyridyl group.
• the molecular weight of the compound having the structure represented by general formula (1) is preferably 400 or more from the viewpoint of suppressing crystallization and improving the stability of film quality.
• the molecular weight of the compound having the structure represented by the general formula (1) is preferably 700 or less from the viewpoint of improving workability during sublimation purification and vapor deposition.
• Examples of the compound having the structure represented by the general formula (1) include the compounds shown below. The following are examples, and compounds other than those specified here are preferably used as long as they have a structure represented by the general formula (1).
• a compound having a structure represented by general formula (1) can be synthesized by a known synthesis method.
• Examples of the synthesis method include, but are not limited to, a coupling reaction between an aryl halide derivative and an arylboronic acid derivative using palladium.
• a compound having a structure represented by general formula (1) represents a material used in any layer of an organic EL device, and includes a hole injection layer, a hole transport layer, a light emitting layer, an electron Materials used for transport layers and protective films (cap layers) of electrodes are included.
• the compound having the structure represented by the general formula (1) in the present invention has excellent heat resistance, and by using such a compound in any layer of the organic EL device, the organic EL device has excellent luminous efficiency and durable life. element can be provided.
• An organic EL element has an anode, a cathode, and an organic layer interposed between the anode and the cathode, and the organic layer emits light by electric energy.
• the layer structure between the anode and the cathode in such an organic EL element includes, in addition to the structure consisting only of the light-emitting layer, 1) light-emitting layer/electron transport layer, 2) hole transport layer/light-emitting layer, 3) hole transport layer/light emitting layer/electron transport layer, 4) hole injection layer/hole transport layer/light emitting layer/electron transport layer, 5) hole transport layer/light emitting layer/electron transport layer/electron injection layer, 6) positive 7) Layered structure of hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer, hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer is mentioned.
• the intermediate layer is also generally referred to as an intermediate electrode, intermediate conductive layer, charge generation layer, electron withdrawal layer, connection layer, and intermediate insulating layer, and known material configurations can be used.
• tandem type include, for example, 8) hole transport layer/light emitting layer/electron transport layer/charge generation layer/hole transport layer/light emitting layer/electron transport layer, 9) hole injection layer/hole transport layer/ A charge-generating layer as an intermediate layer between the anode and the cathode, such as light-emitting layer/electron-transporting layer/electron-injecting layer/charge-generating layer/hole-injecting layer/hole-transporting layer/light-emitting layer/electron-transporting layer/electron-injecting layer.
• a laminate configuration including:
• each of the above layers may be either a single layer or multiple layers, and may be doped.
• the electron injection layer and the charge generation layer are preferably metal-doped layers, so that the electron transport ability and the electron injection ability to other adjacent layers can be improved.
• a protective layer may be further provided, and the light emission efficiency can be further improved by the optical interference effect.
• the compound having the structure represented by general formula (1) may be used in any of the above layers in the organic EL device, but is particularly preferably used in the electron transport layer, charge generation layer or electron injection layer.
• the organic EL device of the present invention preferably has at least an electron-transporting layer and a light-emitting layer between an anode and a cathode, and the electron-transporting layer contains a compound having a structure represented by general formula (1).
• the organic EL device of the present invention has at least a charge-generating layer and a light-emitting layer between an anode and a cathode, and the charge-generating layer contains a compound having a structure represented by general formula (1). is preferred.
• the organic EL device of the present invention has at least an electron injection layer and a light emitting layer between the anode and the cathode, and the electron injection layer contains a compound having a structure represented by general formula (1). is preferred.
• a compound having a structure represented by general formula (1) may be contained in two or more layers.
• the anode and cathode have the role of supplying sufficient current for light emission of the device, and at least one of them is preferably transparent or translucent in order to extract light.
• the anode formed on the substrate is used as a transparent electrode.
• the organic EL element In order to maintain the mechanical strength of the organic EL element, it is preferable to form the organic EL element on a substrate.
• the substrate include glass substrates such as soda glass and alkali-free glass, and plastic substrates.
• the thickness of the glass substrate should be sufficient to maintain the mechanical strength, and a thickness of 0.5 mm or more is sufficient.
• the material of the glass it is preferable that the amount of eluted ions from the glass is small, and alkali-free glass is preferable.
• soda-lime glass with a barrier coating such as SiO 2 is commercially available, and this can also be used.
• the material used for the anode is preferably capable of efficiently injecting holes into the organic layer. Moreover, it is preferably transparent or translucent in order to take out light.
• materials used for the anode include conductive metal oxides such as zinc oxide, tin oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); metals such as gold, silver, and chromium; Inorganic conductive substances such as copper chloride and copper sulfide, and conductive polymers such as polythiophene, polypyrrole and polyaniline are included. Among these, ITO glass and Nesa glass are preferable. These electrode materials may be used alone, or may be used by laminating or mixing a plurality of materials.
• the resistance of the transparent electrode should be sufficient to supply a current sufficient for light emission of the device, but from the viewpoint of power consumption of the device, a low resistance is preferable.
• an ITO substrate with a resistance of 300 ⁇ /square or less functions as an element electrode, but it is now possible to supply a substrate with a resistance of about 10 ⁇ /square, so substrates with a low resistance of 20 ⁇ /square or less are used. is preferred.
• the thickness of ITO can be arbitrarily selected according to the resistance value, and is usually used in the range of 45 to 300 nm.
• the material used for the cathode is not particularly limited as long as it can efficiently inject electrons into the light-emitting layer.
• materials used for the cathode include metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or combinations of these metals with low work function metals such as lithium, sodium, potassium, calcium, and magnesium.
• examples include alloys and multilayer lamination.
• aluminum, silver, and magnesium are preferable as the main component from the viewpoint of electrical resistance, ease of film formation, film stability, luminous efficiency, etc., and electron injection into the electron transport layer and the electron injection layer is easy. Therefore, it is more preferable to be composed of magnesium and silver.
• the material constituting the protective layer is not particularly limited, but examples include metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, alloys using these metals, silica, titania and Inorganic substances such as silicon nitride, and organic polymer compounds such as polyvinyl alcohol, polyvinyl chloride, and hydrocarbon-based polymer compounds are included.
• the organic EL element material represented by the general formula (1) can also be used as a capping material. However, when the organic EL element has an element structure (top emission structure) in which light is extracted from the cathode side, the capping material preferably has light transmittance in the visible light region.
• a hole-injecting layer is a layer interposed between the anode and the hole-transporting layer.
• the hole injection layer may be either a single layer or a laminate of a plurality of layers.
• the presence of a hole injection layer between the hole transport layer and the anode is preferable because it not only enables the device to be driven at a lower voltage and extends the durability life, but also improves the carrier balance of the device and the luminous efficiency.
• the material used for the hole injection layer is not particularly limited. -(1-naphthyl)-N-phenylamino)biphenyl (NPD), 4,4'-bis(N,N-bis(4-biphenylyl)amino)biphenyl (TBDB), bis(N,N'-diphenyl- 4-aminophenyl)-N,N-diphenyl-4,4′-diamino-1,1′-biphenyl (TPD232), 4,4′,4′′-tris(3-methylphenyl(phenyl) amino)triphenylamine (m-MTDATA), 4,4′,4′′-tris(1-naphthyl(phenyl)amino)triphenylamine (1-TNATA), a group of materials called starburst arylamines, triaryl Amine derivatives, bis(N-arylcarbazole), bis(N-alkylcarbazole) and other bis
• a hole injection layer may be formed by laminating a plurality of materials. Furthermore, it is more preferable that the hole injection layer is composed of an acceptor compound alone, or that the hole injection material as described above is doped with an acceptor compound, since the above effects can be obtained more remarkably.
• the acceptor compound is a material that forms a charge-transfer complex with a material that forms a hole-transport layer in contact with it when used as a single-layer film, and a material that forms a hole-injection layer when it is doped and used. The use of such a material improves the conductivity of the hole injection layer, contributes to lowering the drive voltage of the device, and can further improve the luminous efficiency and durable life.
• acceptor compounds include metal chlorides such as iron (III) chloride, aluminum chloride, gallium chloride, indium chloride, and antimony chloride; metal oxides such as molybdenum oxide, vanadium oxide, tungsten oxide, and ruthenium oxide; Charge transfer complexes such as 4-bromophenyl)aminium hexachloroantimonate (TBPAH), organic compounds having a nitro group, cyano group, halogen or trifluoromethyl group in the molecule, quinone compounds, acid anhydride compounds, fullerenes etc.
• TPAH 4-bromophenyl)aminium hexachloroantimonate
• organic compounds having a nitro group, cyano group, halogen or trifluoromethyl group in the molecule quinone compounds, acid anhydride compounds, fullerenes etc.
• metal oxides and cyano group-containing compounds are preferable because they are easy to handle and easy to vapor-deposit, so that the above effects
• the hole-transporting layer is a layer that transports holes injected from the anode to the light-emitting layer.
• the hole transport layer may be either a single layer or a laminate of a plurality of layers.
• Materials used for the hole transport layer include those exemplified as materials used for the hole injection layer.
• a triarylamine derivative and a benzidine derivative are more preferable from the viewpoint of injecting and transporting holes smoothly into the light-emitting layer.
• the light-emitting layer may be either a single layer or multiple layers, each formed of a light-emitting material (host material, dopant material), which may be a mixture of the host material and the dopant material, or the host material alone. , or a mixture of two host materials and one dopant material. That is, in the organic EL element of the present invention, only the host material or the dopant material may emit light, or both the host material and the dopant material may emit light in each light emitting layer. From the viewpoint of efficient use of electrical energy and obtaining light emission with high color purity, the light-emitting layer is preferably made of a mixture of a host material and a dopant material.
• the host material and the dopant material may be of one kind or a combination of a plurality of them.
• the dopant material may be contained entirely or partially in the host material.
• the dopant material can be either layered or dispersed.
• Dopant materials can control the emission color. From the viewpoint of suppressing the concentration quenching phenomenon, the amount of the dopant material is preferably 30% by weight or less, more preferably 20% by weight or less, relative to the host material.
• the doping method can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then vapor-deposited at the same time.
• Examples of light-emitting materials include condensed ring derivatives such as anthracene and pyrene, which are known as light emitters, metal chelated oxinoid compounds such as tris(8-quinolinolato)aluminum, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives, Tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, thiadiazolopyridine derivatives, dibenzofuran derivatives, carbazole derivatives, indolocarbazole derivatives, Examples include polymers such as polyphenylene vinylene derivatives, polyparaphenylene derivatives, polythiophene derivatives, and the like.
• the host material contained in the light-emitting material need not be limited to one type of compound, and a mixture of multiple compounds may be used. Moreover, you may laminate
• Host materials include, but are not limited to, naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluoranthene, fluorene, compounds having condensed aryl rings such as indene, derivatives thereof, N,N'-dinaphthyl- aromatic amine derivatives such as N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, metal chelated oxinoid compounds such as tris(8-quinolinato)aluminum (III), distyrylbenzene derivatives, etc.
• bisstyryl derivatives tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, pyrrolopyrrole derivatives, thiadiazolopyridine derivatives, dibenzofuran derivatives, carbazole derivatives, indolocarbazole Examples include derivatives, triazine derivatives, and polymers such as polyphenylenevinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and polythiophene derivatives.
• the host used when the emitting layer performs triplet emission includes metal chelated oxinoid compounds, dibenzofuran derivatives, dibenzothiophene derivatives, carbazole derivatives, indolocarbazole derivatives, triazine derivatives, triphenylene derivatives, and the like. is preferably used.
• Dopant materials contained in the light-emitting material include, for example, compounds having an aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, fluoranthene, triphenylene, perylene, fluorene, and indene, and derivatives thereof (eg, 2-(benzothiazole-2- yl)-9,10-diphenylanthracene and 5,6,11,12-tetraphenylnaphthacene), furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene , benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, compounds having a heteroaryl ring
• the light-emitting layer preferably contains a triplet light-emitting material.
• a metal complex compound containing at least one metal selected from the group consisting of ) is preferred.
• the ligand preferably has a nitrogen-containing aromatic heterocycle such as a phenylpyridine skeleton, phenylquinoline skeleton, or carbene skeleton. However, it is not limited to these, and an appropriate complex is selected from the required emission color, device performance, and relationship with the host compound.
• tris(2-phenylpyridyl)iridium complex tris ⁇ 2-(2-thiophenyl)pyridyl ⁇ iridium complex, tris ⁇ 2-(2-benzothiophenyl)pyridyl ⁇ iridium complex, tris(2-phenyl benzothiazole)iridium complex, tris(2-phenylbenzoxazole)iridium complex, trisbenzoquinolineiridium complex, bis(2-phenylpyridyl)(acetylacetonate)iridium complex, bis ⁇ 2-(2-thiophenyl)pyridyl ⁇ iridium complex, bis ⁇ 2-(2-benzothiophenyl)pyridyl ⁇ (acetylacetonato)iridium complex, bis(2-phenylbenzothiazole)(acetylacetonato)iridium complex, bis(2-phenylbenzoxazole)(acetylacetonato) nate) iridium
• triplet light-emitting materials used as dopant materials may be contained in the light-emitting layer alone, or may be used in combination of two or more.
• the total weight of the dopant materials is preferably 30% by weight or less, more preferably 20% by weight or less, relative to the host material.
• Preferable hosts and dopants in the triplet emission system are not particularly limited, but specific examples include the following.
• the light emitting layer contains a thermally activated delayed fluorescence material.
• the heat-activated delayed fluorescence is explained on pages 87 to 103 of "State-of-the-Art Organic EL" (edited by Chihaya Adachi and Hiroshi Fujimoto, published by CMC Publishing). In the literature, by bringing the energy levels of the excited singlet state and the excited triplet state close to each other, the reverse energy transfer from the excited triplet state, which normally has a low transition probability, to the excited singlet state is high. It is explained that it occurs efficiently and thermally activated delayed fluorescence (TADF) is expressed. Furthermore, FIG. 5 in the document explains the generation mechanism of delayed fluorescence. Emission of delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.
• Thermally activated delayed fluorescence materials are also generally called TADF materials.
• the thermally activated delayed fluorescence material may be a single material that exhibits thermally activated delayed fluorescence, or a plurality of materials that exhibit thermally activated delayed fluorescence. When a plurality of materials are used, they may be used as a mixture, or may be used by stacking layers of each material.
• a known material can be used as the thermally activated delayed fluorescence material. Examples include, but are not limited to, benzonitrile derivatives, triazine derivatives, disulfoxide derivatives, carbazole derivatives, indolocarbazole derivatives, dihydrophenazine derivatives, thiazole derivatives, oxadiazole derivatives and the like.
• the light-emitting layer further contains a fluorescent dopant. This is because triplet excitons are converted into singlet excitons by the TADF material, and the singlet excitons are received by the fluorescent dopant, thereby achieving higher luminous efficiency and longer durability.
• the electron transport layer is a layer into which electrons are injected from the cathode and which transports the electrons.
• the electron transport layer is desired to have high electron injection efficiency and efficiently transport the injected electrons. Therefore, the material constituting the electron transport layer is preferably a substance that has high electron affinity, high electron mobility, excellent stability, and does not easily generate trapping impurities during production and use.
• a compound having a molecular weight of 400 or more is preferable in order to maintain a stable film quality, because a low-molecular-weight compound tends to crystallize and deteriorate the film quality.
• the electron-transporting layer in the present invention includes a hole-blocking layer that can efficiently block the movement of holes. may be configured.
• electron transport materials used in the electron transport layer include condensed polycyclic aromatic derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4′-bis(diphenylethenyl)biphenyl, anthraquinone and diphenoquinone. quinone derivatives, phosphorus oxide derivatives, quinolinol complexes such as tris(8-quinolinolato)aluminum (III), benzoquinolinol complexes, hydroxyazole complexes, azomethine complexes, tropolone metal complexes and flavonol metal complexes.
• a heteroaryl ring structure composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus and containing an electron-accepting nitrogen can be used to further reduce the driving voltage and obtain more efficient light emission. It is preferable to use a compound having
• the electron-accepting nitrogen here means a nitrogen atom that forms a multiple bond with an adjacent atom. Due to the high electronegativity of the nitrogen atom, the multiple bond has electron-accepting properties. Therefore, heteroaromatic rings containing electron-accepting nitrogen have high electron affinities.
• An electron-transporting material having electron-accepting nitrogen makes it easier to accept electrons from a cathode having a high electron affinity, and can be driven at a lower voltage. In addition, more electrons are supplied to the light-emitting layer and the probability of recombination is increased, so that the light emission efficiency is further improved.
• Heteroaryl rings containing electron-accepting nitrogen include, for example, triazine ring, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, quinoxaline ring, quinazoline ring, naphthyridine ring, pyrimidopyrimidine ring, benzoquinoline ring, phenanthroline ring, imidazole ring, oxazole ring, oxadiazole ring, triazole ring, thiazole ring, thiadiazole ring, benzoxazole ring, benzothiazole ring, benzimidazole ring, phenanthroimidazole ring and the like.
• Examples of compounds having these heteroaryl ring structures include pyridine derivatives, triazine derivatives, quinazoline derivatives, pyrimidine derivatives, benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazine. derivatives, phenanthroline derivatives, quinoxaline derivatives, quinoline derivatives, benzoquinoline derivatives, oligopyridine derivatives such as bipyridine and terpyridine, quinoxaline derivatives and naphthyridine derivatives.
• imidazole derivatives such as tris(N-phenylbenzimidazol-2-yl)benzene, oxadiazole derivatives such as 1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene, triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole, phenanthroline derivatives such as bathocuproine and 1,3-bis(1,10-phenanthrolin-9-yl)benzene, 2,2' - benzoquinoline derivatives such as bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, 2,5-bis(6'-(2',2''-bipyridyl))-1, bipyridine derivatives such as 1-dimethyl-3,4-diphenylsilole, terpyridine derivatives such as 1,3-bis(4′-
• the condensed polycyclic aromatic skeleton is preferably a fluoranthene skeleton, anthracene skeleton, a pyrene skeleton, or a phenanthroline skeleton. more preferred.
• Preferable electron-transporting materials are not particularly limited, but specific examples include the following.
• a compound having a structure represented by general formula (1) is also preferable because it has a high electron-transporting property and exhibits excellent properties as an electron-transporting layer.
• the electron-transporting material may be used alone, or two or more of the electron-transporting materials may be mixed and used, or one or more other electron-transporting materials may be mixed with the electron-transporting material. I do not care. Moreover, you may contain a donor compound.
• the donor compound is a compound that facilitates the injection of electrons from the cathode or the electron injection layer into the electron transport layer by improving the electron injection barrier and further improves the electrical conductivity of the electron transport layer.
• the donor compound include an alkali metal, an inorganic salt containing an alkali metal, a complex of an alkali metal and an organic substance, an alkaline earth metal, an inorganic salt containing an alkaline earth metal, or a mixture of an alkaline earth metal and an organic substance. complexes, rare earth metals, and the like.
• alkali metals, alkaline earth metals, and rare earth metals include alkali metals such as lithium, sodium, potassium, rubidium, and cesium, which have a low work function and are highly effective in improving electron transport ability, and magnesium, calcium, cerium, and barium. and alkaline earth metals such as samarium, europium, and ytterbium. A plurality of these metals may be used, or an alloy of these metals may be used.
• inorganic salts include oxides and nitrides such as LiO and Li 2 O, fluorides such as LiF, NaF and KF, Li 2 CO 3 , Na 2 CO 3 , K 2 CO 3 , Rb 2 CO 3 , Carbonates such as Cs 2 CO 3 and the like are included.
• alkali metals or alkaline earth metals include lithium and cesium from the viewpoint that the driving voltage can be further reduced.
• the organic matter in the complex with the organic matter include quinolinol, benzoquinolinol, pyridylphenol, flavonol, hydroxyimidazopyridine, hydroxybenzazole, and hydroxytriazole.
• a complex of an alkali metal and an organic substance is preferable from the viewpoint that the driving voltage of the organic EL device can be further reduced. That is, it is preferred that the electron transport layer further contains an alkali metal complex compound.
• the alkali metal complex compound a complex of lithium and an organic substance is more preferable from the viewpoint of ease of synthesis and thermal stability, and lithium quinolinol (Liq), which is available at a relatively low cost, is particularly preferable.
• the ionization potential of the electron transport layer is not particularly limited, it is preferably 5.6 eV or more and 8.0 eV or less, more preferably 5.6 eV or more and 7.0 eV or less.
• each layer constituting the organic EL element is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, and coating method. is preferred.
• an electron injection layer may be provided between the cathode and the electron transport layer.
• the electron injection layer is inserted for the purpose of assisting the injection of electrons from the cathode into the electron transport layer.
• a layer containing the above-described donor material may be used.
• inorganic materials such as insulators and semiconductors can also be used for the electron injection layer.
• the short circuit of the organic EL element can be suppressed and the electron injection properties can be improved.
• Such an insulator is preferably at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides.
• preferred alkali metal chalcogenides include, for example, Li2O , Na2S and Na2Se .
• Preferred alkaline earth metal chalcogenides also include, for example, CaO, BaO, SrO, BeO, BaS and CaSe.
• Preferred alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl and NaCl.
• Preferred examples of halides of alkaline earth metals include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
• a complex of an organic substance and a metal is also preferably used.
• a complex of an organic substance and a metal is used for the electron injection layer, the film thickness can be easily adjusted.
• organic substances in organometallic complexes include quinolinol, benzoquinolinol, pyridylphenol, flavonol, hydroxyimidazopyridine, hydroxybenzazole, and hydroxytriazole.
• a layer containing a compound having a structure represented by general formula (1) is also preferable because it has high electron injection properties and exhibits excellent properties as an electron injection layer.
• the compound represented by the general formula (1) is preferably doped with the above alkali metal or rare earth metal, so that the driving voltage can be further reduced and the durability life can be further improved.
• the charge generation layer in the present invention generally consists of a double layer, and specifically can be used as a pn junction type charge generation layer consisting of an n-type charge generation layer and a p-type charge generation layer.
• the pn junction charge generation layer generates charges or separates the charges into holes and electrons when a voltage is applied in the organic EL element, and converts these holes and electrons into holes and electrons. It is injected into the light-emitting layer via the transport layer. Specifically, it functions as an intermediate charge generation layer in an organic EL device having a stack of light-emitting layers.
• the n-type charge-generating layer supplies electrons to the first light-emitting layer on the anode side
• the p-type charge-generating layer supplies holes to the second light-emitting layer on the cathode side. Therefore, it is possible to further improve the luminous efficiency of the organic EL element in which a plurality of light-emitting layers are laminated, reduce the driving voltage, and further improve the durable life of the element.
• the n-type charge generation layer consists of an n-type dopant and a host, and conventional materials can be used for these.
• alkali metals, alkaline earth metals, or rare earth metals can be used as n-type dopants.
• the charge generation layer further contains an alkali metal and/or a rare earth metal.
• the alkali metal is Li.
• the rare earth metal is Yb.
• compounds having a nitrogen-containing aromatic heterocycle such as phenanthroline derivatives and oligopyridine derivatives can be used.
• the compound having the structure represented by the general formula (1) and the phenanthroline dimer exhibit excellent properties as a host for the n-type charge generation layer, and they may be used in combination.
• the charge generation layer further contains a phenanthroline dimer.
• phenanthroline dimers are not particularly limited, but specific examples are given below.
• the p-type charge generation layer consists of a p-type dopant and a host, which can be conventional materials.
• p-type dopants include tetrafluor-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), tetracyanoquinodimethane derivatives, radialene derivatives, iodine, FeCl 3 , FeF 3 , SbCl 5 etc. can be used.
• Preferred p-type dopants are radialene derivatives.
• Preferred hosts are arylamine derivatives.
• the thickness of the organic layer depends on the resistance value of the light-emitting substance and cannot be limited, but is preferably 1 to 1000 nm.
• Each of the light-emitting layer, the electron transport layer, and the hole transport layer preferably has a film thickness of 1 nm or more and 200 nm or less, more preferably 5 nm or more and 100 nm or less.
• the organic EL element of the present invention has the function of converting electrical energy into light.
• direct current is mainly used as electric energy, but pulse current and alternating current can also be used.
• the current value and voltage value it should be selected so that the maximum luminance can be obtained with the lowest possible energy.
• the organic EL element of the present invention is suitable for use as a display device such as a matrix and/or segment display. That is, the display device of the present invention includes the organic EL element of the present invention.
• the organic EL element of the present invention is also preferably used as a backlight for various devices.
• Backlights are mainly used for the purpose of improving the visibility of display devices such as non-self-luminous displays, and are used in liquid crystal displays, clocks, audio devices, automobile panels, display boards, signs, and the like.
• the organic EL device of the present invention is preferably used for liquid crystal displays, especially for backlights for personal computers, for which thinning is being considered, and it is possible to provide thinner and lighter backlights than conventional ones.
• the organic EL device of the present invention is also preferably used as various lighting devices.
• the organic EL device of the present invention can achieve both high luminous efficiency and high color purity, and can be made thinner and lighter.
• a combined lighting device can be realized. That is, the lighting device of the present invention includes the organic EL element of the present invention.
• the ampoule was sealed in a vacuum-exchanged ampule and held in an oven at 385° C. for 150 hours. After that, the temperature was returned to room temperature, and the HPLC purity of the sample was determined in the same manner. The smaller the change in purity before and after the heat resistance test, the better the heat resistance can be evaluated.
• the organic EL devices obtained in Examples 33 to 64 and Comparative Examples 11 to 20 were each driven at a current density of 10 mA/cm 2 and the initial driving voltage was measured.
• Luminance The organic EL devices obtained in Examples 33 to 64 and Comparative Examples 11 to 20 were lit at 10 mA/cm 2 , luminance was measured, and luminous efficiency was evaluated. It can be evaluated that the higher the luminance, the better the luminous efficiency.
• the organic EL devices obtained in Examples 17 to 64 and Comparative Examples 6 to 20 were continuously driven at a constant current of 10 mA/cm 2 , and the time required for the luminance to decrease by 20% from the initial luminance was measured. It can be evaluated that the longer the time to decrease, the better the durability life.
• Example 1 To a mixed solution of 4.0 g of bromobenzene and 26 ml of tetrahydrofuran was added dropwise 17.4 ml of n-butyllithium (1.6 M hexane solution) at 0° C. under a nitrogen stream. After stirring at 0°C for 1 hour, it was added dropwise at 0°C to a mixed solution of 5.0 g of 3,4,7,8-tetramethyl-1,10-phenanthroline and 40 ml of tetrahydrofuran. After cooling to room temperature, the reaction solution was extracted with dichloromethane, leaving 100 ml of solvent and evaporated.
• n-butyllithium 1.6 M hexane solution
• the resulting compound 1 was purified by sublimation at about 320° C. under a pressure of 1 ⁇ 10 ⁇ 3 Pa using an oil diffusion pump.
• the HPLC purity (area % at a measurement wavelength of 254 nm) of Compound 1 before and after sublimation purification was both 99.9%.
• Example 2 To a mixed solution of 3.2 g of 1,4-dibromobenzene and 20 ml of tetrahydrofuran was added dropwise 7.8 ml of n-butyl lithium (1.6 M hexane solution) at 0° C. under a nitrogen stream. After stirring at 0°C for 1 hour, it was added dropwise at 0°C to a mixed solution of 2.6 g of 3,4,7,8-tetramethyl-1,10-phenanthroline and 20 ml of tetrahydrofuran. After cooling to room temperature, the reaction solution was extracted with dichloromethane, leaving 100 ml of solvent and evaporated.
• n-butyl lithium 1.6 M hexane solution
• the resulting compound 2 was purified by sublimation at about 360° C. under a pressure of 1 ⁇ 10 ⁇ 3 Pa using an oil diffusion pump.
• the HPLC purity (area % at a measurement wavelength of 254 nm) of compound 2 before and after sublimation purification was both 99.9%.
• Example 20 A glass substrate (manufactured by Geomatec, 11 ⁇ / ⁇ , sputtered product) on which an ITO transparent conductive film of 165 nm was deposited as an anode was cut into 38 mm ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned for 15 minutes using "Semico Clean" 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.) and then cleaned with ultrapure water. This substrate was treated with UV-ozone for 1 hour immediately before manufacturing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus reached 5 ⁇ 10 ⁇ 4 Pa or less.
• "Semico Clean" 56 trade name, manufactured by Furuuchi Chemical Co., Ltd.
• HAT-CN 6 was vapor-deposited to a thickness of 5 nm as a hole injection layer, and then HT-1 was vapor-deposited to a thickness of 50 nm as a hole transport layer by resistance heating.
• a mixed layer of host material H-1 and dopant material D-1 was deposited to a thickness of 20 nm with a doping concentration of 5% by weight.
• aluminum was vapor-deposited to a thickness of 60 nm to form a cathode, and an organic EL element of 5 mm ⁇ 5 mm square was produced.
• Examples 21-38, Comparative Examples 6-10 An organic EL device was produced in the same manner as in Example 20, except that the compounds used were changed as shown in Table 2. Table 2 shows the results of each example and comparative example.
• Example 39 A glass substrate (manufactured by Geomatec, 11 ⁇ / ⁇ , sputtered product) on which an ITO transparent conductive film of 165 nm was deposited as an anode was cut into 38 mm ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned for 15 minutes using "Semico Clean" 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.) and then cleaned with ultrapure water. This substrate was treated with UV-ozone for 1 hour immediately before manufacturing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus reached 5 ⁇ 10 ⁇ 4 Pa or less. First, HAT-CN 6 was vapor-deposited to 5 nm as a hole injection layer by a resistance heating method. Next, a light-emitting unit (first light-emitting unit) was formed on the hole-injection layer, comprising a hole-transporting layer, a light-emitting layer, and an electron-transporting layer.
• first light-emitting unit
• HT-1 was vapor-deposited to a thickness of 50 nm as a hole transport layer, and then a mixed layer of host material H-1 and dopant material D-1 was formed as a light-emitting layer with a doping concentration of 5% by weight. Then, as an electron transport layer, ET-1 and 2E-1 were deposited to a thickness of 35 nm so that the deposition rate ratio of ET-1 and 2E-1 was 1:1. vapor-deposited on.
• HAT-CN 6 was evaporated to 10 nm as a P-type charge generation layer.
• a second light-emitting unit was formed in the same manner as the first light-emitting unit.
• a 5 mm square organic EL device was produced.
• the initial drive voltage was 8.81 V
• the luminance was 1610 cd/m 2
• the endurance life was 2400 hours.
• Examples 40-60, Comparative Examples 11-15 An organic EL device was produced in the same manner as in Example 39, except that the compounds and metal elements used were changed as shown in Table 3. Table 3 shows the results of each example and comparative example.
• Example 61 Same as Example 33 except that Compound 1 was used instead of ET-1 in the formation of the electron transport layer, and ET-2 was used instead of Compound 1 in the formation of the N-type charge generation layer. Then, an organic EL device was produced.
• ET-2 is a compound shown below.
• the initial drive voltage was 8.83 V
• the luminance was 1600 cd/m 2
• the endurance life was 2410 hours.
• Examples 62-79, Comparative Examples 16-20 An organic EL device was produced in the same manner as in Example 61, except that the compounds used were changed as shown in Table 4. Table 4 shows the results of each example and comparative example.

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