WO2015034093A1 - Composé de 2-aminocarbazole et son utilisation - Google Patents

Composé de 2-aminocarbazole et son utilisation Download PDF

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WO2015034093A1
WO2015034093A1 PCT/JP2014/073718 JP2014073718W WO2015034093A1 WO 2015034093 A1 WO2015034093 A1 WO 2015034093A1 JP 2014073718 W JP2014073718 W JP 2014073718W WO 2015034093 A1 WO2015034093 A1 WO 2015034093A1
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group
mmol
methyl
compound according
methoxy
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PCT/JP2014/073718
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English (en)
Japanese (ja)
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松本　直樹
宏和 新屋
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東ソー株式会社
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Priority claimed from JP2013216683A external-priority patent/JP6311266B2/ja
Priority claimed from JP2014028366A external-priority patent/JP2015071582A/ja
Application filed by 東ソー株式会社 filed Critical 東ソー株式会社
Priority to KR1020217016773A priority Critical patent/KR102424458B1/ko
Priority to CN201480049605.8A priority patent/CN105531262B/zh
Priority to KR1020167003993A priority patent/KR102280834B1/ko
Publication of WO2015034093A1 publication Critical patent/WO2015034093A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—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

Definitions

  • the present invention relates to a 2-aminocarbazole compound and an organic EL device using the same.
  • An organic EL element is a surface-emitting element in which an organic thin film is sandwiched between a pair of electrodes, and has features such as thin and light weight, high viewing angle, and high-speed response, and is expected to be applied to various display elements. Yes. Recently, some practical applications such as mobile phone displays have begun.
  • the organic EL element uses light emitted when holes injected from the anode and electrons injected from the cathode are recombined in the light emitting layer, and the structure thereof is a hole transport layer, a light emitting layer.
  • the mainstream is a multilayer stack type in which an electron transport layer and the like are stacked.
  • the charge transport layer such as the hole transport layer and the electron transport layer does not emit light by itself, but facilitates the charge injection into the light emitting layer, and further, the charge injected into the light emitting layer and the light emitting layer It plays the role of confining the energy of the generated excitons. That is, the charge transport layer plays an extremely important role in reducing the driving voltage and improving the light emission efficiency of the organic EL element.
  • an amine compound having an appropriate ionization potential and hole transporting ability is used as the hole transporting material.
  • an amine compound having an appropriate ionization potential and hole transporting ability is used.
  • 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter, referred to as “4”) is used.
  • NPD is well known.
  • the driving voltage, light emission efficiency and durability of an element using NPD for the hole transport layer are not sufficient, and development of new materials is required.
  • organic EL elements using a phosphorescent material for a light emitting layer have been developed, and a hole transport material having a high triplet level is required for an element using phosphorescent light emission.
  • NPD is not sufficient from the point of triplet level, and for example, it has been reported that the organic EL element in which a phosphorescent material having green light emission and NPD are combined reduces the luminous efficiency (for example, non-patent Reference 1).
  • amine compounds having a carbazole ring introduced in the molecule have been reported. Specific examples include 2-aminocarbazole compounds (see, for example, Patent Documents 1 to 4).
  • Patent Documents 1 and 2 2-aminocarbazole compounds containing a pyrene ring and an anthracene ring are disclosed for use as light emitting materials, respectively. Since these compounds containing a pyrene ring or an anthracene ring have a low triplet level of the pyrene ring and the anthracene ring itself, a device using a green phosphorescent material cannot obtain high emission efficiency. On the other hand, the 2-aminocarbazole compounds disclosed in Patent Documents 3 and 4 have higher triplet levels than NPD. For this reason, it is known that elements using a green phosphorescent material generally tend to exhibit higher luminous efficiency than NPD.
  • An object of the present invention is to provide a 2-aminocarbazole compound having a specific chemical structure that remarkably improves the lifetime of an organic EL device as compared with a conventionally known 2-aminocarbazole compound or 3-aminocarbazole compound.
  • Another object of the present invention is to provide an organic EL device having an excellent long life using the 2-aminocarbazole compound having the specific chemical structure.
  • the present inventors have found a 2-aminocarbazole compound, which is a novel compound represented by the following formula (1), and completed the present invention. That is, the present invention relates to a 2-aminocarbazole compound represented by the following formula (1) and its use.
  • R each independently represents a hydrogen atom or a methyl group.
  • R 1 to R 3 is a 4-dibenzothienyl group, a 4-dibenzofuranyl group, a 9-phenanthryl group, or a group represented by the following formula:
  • the substituent represented by (2), the remainder being a hydrogen atom or a methyl group, Ar 1 and Ar 2 are each independently an aromatic hydrocarbon group having 6 to 18 carbon atoms, , May have a methyl group or a methoxy group.) (R represents a hydrogen atom or a methyl group.)
  • the organic EL device using the 2-aminocarbazole compound of the present invention is remarkably superior in device lifetime as compared with a conventionally known organic EL device using 2-aminocarbazole compound or 3-aminocarbazole. Therefore, the 2-aminocarbazole compound of the present invention can be used as an organic EL material having excellent durability.
  • the organic EL element can have a longer life, a lower driving voltage, and a higher luminous efficiency than NPD which is a conventionally known hole transport material. That is, according to the present invention, an organic EL element with low power consumption and excellent element lifetime can be provided.
  • each R independently represents a hydrogen atom or a methyl group.
  • R is a hydrogen atom from the point of a hole transport characteristic and the ease of raw material acquisition.
  • any one of R 1 to R 3 is a 4-dibenzothienyl group, a 4-dibenzofuranyl group, a 9-phenanthryl group, or the following formula ( 2) and the remainder is a hydrogen atom or a methyl group.
  • R represents a hydrogen atom or a methyl group.
  • any one of R 1 to R 3 is a 4-dibenzothienyl group, a 4-dibenzofuranyl group, a 9-phenanthryl group, or the above formula ( The substituent represented by 2) is preferred, and the remainder is a hydrogen atom.
  • Ar 1 and Ar 2 each independently represents an aromatic hydrocarbon group having 6 to 18 carbon atoms, which includes a methyl group, a methoxy group You may have.
  • the aromatic hydrocarbon group having 6 to 18 carbon atoms in Ar 1 and Ar 2 (which may have a methyl group or a methoxy group) is not particularly limited. , Biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, phenanthryl group, benzofluorenyl group (these may have a methyl group or a methoxy group) and the like.
  • Ar 1 and Ar 2 include phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3, 4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl Group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 2-methyl-4-methoxyphenyl group, 2-methyl-5-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl Group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 2,
  • Ar 1 and Ar 2 in the 2-amino carbazole compound represented by the formula (1) of the present invention are each independently, may have a methyl group or a methoxy group
  • a terphenyl group which may have a methoxy group, or a fluorenyl group which may have a methyl group or a methoxy group is preferable.
  • Ar 1 and Ar 2 are each independently a phenyl group, 4-methylphenyl group, 1-naphthyl group, 9-phenanthryl group, 4-biphenylyl group, p-terphenyl-4-yl group, m It is more preferably a terphenyl-4-yl group or a 9,9-dimethyl-9H-fluoren-2-yl group.
  • the 2-aminocarbazole compound represented by the formula (1) is a light emitting host material in a light emitting layer of an organic EL device, a hole transport material in a hole transport layer, or a hole transport material in a hole injection layer (particularly limited). However, these materials can be collectively used as an organic EL element material).
  • the 2-aminocarbazole compound represented by the formula (1) is preferably highly pure in terms of hole transport characteristics and device lifetime.
  • the 2-aminocarbazole compound represented by the formula (1) is used as a hole injection layer and / or a hole transport layer of an organic EL device
  • a conventionally known fluorescent material is used.
  • a phosphorescent material can be used.
  • the light emitting layer may be formed of only one kind of light emitting material, or one or more kinds of light emitting materials may be doped in the host material.
  • two or more kinds of materials may be contained or laminated as necessary.
  • oxides such as molybdenum oxide, 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane
  • a known electron-accepting material such as hexacyanohexaazatriphenylene may be contained or laminated.
  • the 2-aminocarbazole compound represented by the formula (1) of the present invention can also be used as a light emitting layer of an organic EL device.
  • an arylamine compound is used alone, a known light emitting host material is used, or It can be used by doping with a known light emitting dopant.
  • Examples of a method for forming a hole injection layer, a hole transport layer, or a light emitting layer containing the 2-aminocarbazole compound represented by the formula (1) include a vacuum deposition method, a spin coating method, and a casting method. A known method can be applied.
  • the method for producing a thin film for an organic electroluminescent device comprising the 2-aminocarbazole compound represented by the above formula (1) of the present invention is not particularly limited, but can be formed by a vacuum deposition method. It is. Film formation by the vacuum evaporation method can be performed by using a general-purpose vacuum evaporation apparatus.
  • the vacuum degree of the vacuum chamber when forming a film by the vacuum deposition method is determined by taking into account the manufacturing tact time and manufacturing cost of manufacturing the organic electroluminescence device, and commonly used diffusion pumps, turbo molecular pumps, cryopumps, etc. Can be reached.
  • the degree of vacuum is preferably about 1 ⁇ 10 ⁇ 2 to 1 ⁇ 10 ⁇ 6 Pa, and more preferably 1 ⁇ 10 ⁇ 4 to 1 ⁇ 10 ⁇ 6 Pa.
  • the deposition rate is preferably 0.005 to 1.0 nm / second, and more preferably 0.01 to 0.3 nm / second, depending on the thickness of the film to be formed.
  • the 2-aminocarbazole compound represented by the formula (1) of the present invention since the 2-aminocarbazole compound represented by the formula (1) of the present invention has high heat resistance, it does not easily undergo thermal decomposition even during high-speed film formation and has little influence on device performance.
  • the basic structure of the organic EL device that can obtain the effects of the present invention includes a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode.
  • the anode and cathode of the organic EL element are connected to a power source through an electrical conductor.
  • the organic EL element operates by applying a potential between the anode and the cathode. Holes are injected into the organic EL element from the anode, and electrons are injected into the organic EL element at the cathode.
  • the organic EL element is typically placed on a substrate, and the anode or cathode can be in contact with the substrate.
  • the electrode in contact with the substrate is called the lower electrode for convenience.
  • the lower electrode is an anode, but the organic EL element of the present invention is not limited to such a form.
  • the substrate may be light transmissive or opaque depending on the intended emission direction.
  • the light transmission characteristics can be confirmed by electroluminescence emission through the substrate.
  • transparent glass or plastic is used as the substrate in such a case.
  • the substrate may be a composite structure including multiple material layers. When the electroluminescent emission is confirmed through the anode, the anode is formed by passing or substantially passing through the emission.
  • the general transparent anode (anode) material used in the present invention is not particularly limited, and examples thereof include indium-tin oxide (ITO), indium-zinc oxide (IZO), and tin oxide.
  • ITO indium-tin oxide
  • IZO indium-zinc oxide
  • tin oxide Other metal oxides such as aluminum or indium doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide can also be used.
  • metal nitrides such as gallium nitride, metal selenides such as zinc selenide, or metal sulfides such as zinc sulfide can be used as the anode. .
  • the anode can be modified with plasma-deposited fluorocarbon. If electroluminescence emission is confirmed only through the cathode, the transmission properties of the anode are not critical and any conductive material that is transparent, opaque or reflective can be used. Examples of conductors for this application include gold, iridium, molybdenum, palladium, platinum and the like.
  • a plurality of hole transporting layers such as a hole injection layer and a hole transport layer can be provided between the anode and the light emitting layer.
  • the hole injection layer and the hole transport layer have a function of transmitting holes injected from the anode to the light emitting layer.
  • the hole injection layer and the hole transport layer are often used in a lower electric field. Holes can be injected into the light emitting layer.
  • the hole transport layer and / or the hole injection layer contains a 2-aminocarbazole compound represented by the formula (1).
  • a 2-aminocarbazole compound represented by the formula (1) any one of known hole transport materials and / or hole injection materials can be used together with the 2-aminocarbazole compound represented by the formula (1). They can be selected and used in combination.
  • hole injection materials and hole transport materials include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, Examples include oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, and thiophene oligomers.
  • hole injecting material and the hole transporting material those described above can be used, but porphyrin compounds, aromatic tertiary amine compounds, styrylamine compounds and the like can also be used, and in particular, aromatic tertiary amine compounds. Is preferably used.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl, N, N′-diphenyl-N, N ′.
  • Inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
  • the hole injection layer and / or hole transport layer may have a single layer structure composed of one or more of the above materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.
  • the light emitting layer of the organic EL element contains a phosphorescent material or a fluorescent material, and emits light as a result of recombination of electron / hole pairs in this region.
  • the light-emitting layer may be formed from a single material that includes both small molecules and polymers, but more commonly is formed from a host material doped with a guest compound, where light emission originates primarily from dopants, Can have any color.
  • a 2-aminocarbazole compound represented by the above formula (1) can be used as the host material of the light emitting layer.
  • Examples of other compounds include a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, Examples include compounds having a pyrenyl group or an anthranyl group.
  • DPVBi 4,4′-bis (2,2-diphenylvinyl) -1,1′-biphenyl
  • BCzVBi 4,4′-bis (9-ethyl-3-carbazovinylene) 1,1 '-Biphenyl
  • TBADN (2-tert-butyl-9,10-di (2-naphthyl) anthracene
  • ADN (9,10-di (2-naphthyl) anthracene)
  • CBP 4,4'-bis ( Carbazol-9-yl) biphenyl
  • CDBP 4,4′-bis (carbazol-9-yl) -2,2′-dimethylbiphenyl
  • 9,10-bis (biphenyl) anthracene and the like.
  • the host material in the light emitting layer may be an electron transport material as defined below, a hole transport material as defined above, another material that supports hole / electron recombination (support), or a combination of
  • fluorescent dopants examples include anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compound, thiopyran compound, polymethine compound, pyrylium or thiapyrylium compound, fluorene derivative, perifuranthene derivative, indenoperylene derivative, Examples thereof include bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, and carbostyryl compounds.
  • an organometallic complex of a transition metal such as aluminum, iridium, platinum, palladium, or osmium can be given.
  • dopants include Alq 3 (tris (8-hydroxyquinoline) aluminum)), DPAVBi (4,4′-bis [4- (di-para-tolylamino) styryl] biphenyl), perylene, Ir (PPy) 3 ( And tris (2-phenylpyridine) iridium (III), FlrPic (bis (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III)), and the like.
  • Examples of the electron transporting material include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes.
  • Examples of the alkali metal complex, alkaline earth metal complex, or earth metal complex include 8-hydroxyquinolinate lithium (Liq), bis (8-hydroxyquinolinato) zinc, and bis (8-hydroxyquinolinate).
  • a hole blocking layer may be provided between the light emitting layer and the electron transport layer for the purpose of improving carrier balance.
  • Preferred compounds for the hole blocking layer are BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2 -Methyl-8-quinolinolato) -4- (phenylphenolato) aluminum), or bis (10-hydroxybenzo [h] quinolinato) beryllium).
  • an electron injection layer may be provided for the purpose of improving electron injection properties and improving device characteristics (for example, light emission efficiency, constant voltage driving, or high durability).
  • Preferred compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone, etc. Is mentioned.
  • the cathode used in the present invention can be formed from any conductive material.
  • Desirable cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixture, indium , Lithium / aluminum mixtures, rare earth metals and the like.
  • 2-aminocarbazole compound represented by the above formula (1) examples include a 2-aminocarbazole compound represented by the following formula (1A) and a 2-aminocarbazole compound represented by the following formula (1B). Carbazole compounds can be indicated.
  • R 1A to R 7A each independently represents a hydrogen atom or a methyl group.
  • Ar 1 and Ar 2 are each independently an aromatic hydrocarbon group having 6 to 18 carbon atoms, (It may have a methyl group or a methoxy group.
  • One of R 8A and R 9A is a group represented by the following formula (2A), and the other is a hydrogen atom.
  • R 10A represents a hydrogen atom or a methyl group.
  • the 2-aminocarbazole compound represented by the formula (1A) is a compound in which one of R 1 and R 2 in the formula (1) is the group of the formula (2) and the other is a hydrogen atom, R 3 is a hydrogen atom or a methyl group.
  • R 1A to R 7A each independently represents a hydrogen atom or a methyl group.
  • R 1A , R 2A , R 4A , R 5A , R 6A , and R 7A are preferably hydrogen atoms, and R 1A to R 7A are More preferably, all are hydrogen atoms.
  • Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group having 6 to 18 carbon atoms, which includes a methyl group, a methoxy group You may have.
  • the aromatic hydrocarbon group having 6 to 18 carbon atoms in Ar 1 and Ar 2 is not particularly limited, and examples thereof include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a benzofuryl group.
  • Olenyl groups (these groups may have a methyl group or a methoxy group, and the number of substituents is not particularly limited).
  • Ar 1 and Ar 2 include phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3, 4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl Group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 2-methyl-4-methoxyphenyl group, 2-methyl-5-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl Group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 2,
  • Ar 1 and Ar 2 in the 2-aminocarbazole compound represented by the formula (1A) of the present invention may each independently have a methyl group or a methoxy group.
  • the compound (A25), the compound (A26), the compound (A27), the compound (A28), the compound (A29), the compound (A47), or Compound (A53) is more preferred.
  • the 2-aminocarbazole compound represented by the formula (1A) is, for example, a known method (Tetrahedron Letters, 1998, Vol. 39, page 2367, using a 9H-carbazole compound halogenated at the 2-position as a raw material. ) Can be synthesized. Specifically, it can be synthesized by the following route.
  • a 2-halogenated-9-substituted carbazole compound represented by the formula (5A) is obtained.
  • the obtained 2-halogenated-9-substituted carbazole compound represented by the formula (5A) and the secondary amine compound represented by the formula (6A) are combined with a copper catalyst or a palladium catalyst in the presence of a base. To react.
  • Ar 1 , Ar 2 , and R 1A to R 9A represent the same definition as in the formula (1), and A and B each independently represent a halogen atom (iodine, bromine, chlorine, or fluorine)). .
  • the compound represented by the formula (3A) can be synthesized based on a generally known method (for example, Japanese Patent Application Laid-Open No. 2011-1349).
  • the compound represented by the formula (4A) can be synthesized based on a generally known method (for example, WO2008-013399).
  • a commercially available compound can be used, or it can be synthesized based on a generally known method.
  • the 2-aminocarbazole compound represented by the formula (1A) of the present invention can be used as a material for a light emitting layer, a hole transport layer or a hole injection layer of an organic EL device.
  • the 2-aminocarbazole compound represented by the formula (1A) is preferably highly pure in terms of hole transport characteristics and device lifetime.
  • the 2-aminocarbazole compound represented by the formula (1A) is used as a hole injection layer and / or a hole transport layer of an organic EL device
  • a known fluorescence that has been conventionally used is used.
  • a phosphorescent material can be used.
  • the light emitting layer may be formed of only one kind of light emitting material, or one or more kinds of light emitting materials may be doped in the host material.
  • two or more kinds of materials may be contained or laminated as necessary.
  • oxides such as molybdenum oxide, 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane,
  • a known electron-accepting material such as hexacyanohexaazatriphenylene may be contained or laminated.
  • the 2-aminocarbazole compound represented by the formula (1A) is used as a light-emitting layer of an organic EL device, it is used by doping a known light-emitting host material that uses the 2-aminocarbazole compound alone. Or doped with a known luminescent dopant.
  • Examples of a method for forming a hole injection layer, a hole transport layer, or a light emitting layer containing the 2-aminocarbazole compound represented by the formula (1A) include a vacuum deposition method, a spin coating method, and a casting method. A known method can be applied.
  • R 1B to R 3B is a 4-dibenzothienyl group, a 4-dibenzofuranyl group or a 9-phenanthryl group, and the rest are hydrogen atoms.
  • Ar 1 and Ar 2 are each independently And an aromatic hydrocarbon group having 6 to 18 carbon atoms, which may have a methyl group or a methoxy group.
  • a part of R in the formula (1) is a hydrogen atom, and any one of R 1 to R 3 is a 4-dibenzothienyl group, 4 A compound which is a -dibenzofuranyl group or a 9-phenanthryl group, and the remainder is a hydrogen atom.
  • Ar 1 and Ar 2 are each independently an aromatic hydrocarbon group having 6 to 18 carbon atoms, and these are a methyl group or a methoxy group You may have.
  • the aromatic hydrocarbon group having 6 to 18 carbon atoms in Ar 1 and Ar 2 is not particularly limited, and examples thereof include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a benzofuryl group.
  • Examples include oleenyl group, triphenylenyl group, fluoranthenyl group (these substituents may have a methyl group or a methoxy group, and the number of the methyl group or methoxy group is not particularly limited).
  • Ar 1 and Ar 2 include phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3, 4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl Group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 2-methyl-4-methoxyphenyl group, 2-methyl-5-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl Group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 2,
  • Ar 1 and Ar 2 are each independently a phenyl group optionally having a methyl group or a methoxy group, a naphthyl group optionally having a methyl group or a methoxy group in terms of hole transport properties, A phenanthryl group which may have a methyl group or a methoxy group, a biphenylyl group which may have a methyl group or a methoxy group, a terphenyl group which may have a methyl group or a methoxy group, or a methyl group or A fluorenyl group which may have a methoxy group, preferably a phenyl group, a 4-methylphenyl group, a 1-naphthyl group, a 9-phenanthryl group, a 4-biphenylyl group, p-terphenyl-4-yl And more preferably a m-terphenyl-4-yl group or a 9,9-dimethyl-9H-fluoren-2-
  • the compound (B2), the compound (B5), the compound (B25), the compound (B26), the compound (B27), the compound (B28), and the compound in terms of the triplet level and the hole transport property is more preferable.
  • the 2-aminocarbazole compound represented by the formula (1B) is, for example, a known method (Tetrahedron Letters, 1998, 39, 2367 using a 9H-carbazole compound halogenated at the 2-position as a raw material. ) Can be synthesized. Specifically, it can be synthesized by the following route.
  • R 1B to R 3B , Ar 1 and Ar 2 represent the same definition as in the formula (1B).
  • a and B each independently represent a halogen atom (iodine, bromine, chlorine, or fluorine).
  • a 9H-carbazole compound halogenated at the 2-position represented by the formula (2B) and a compound having a halogen atom represented by the formula (3B) are treated with copper in the presence of a base.
  • the reaction is carried out using a catalyst or a palladium catalyst to obtain a 2-halogenated-9-substituted carbazole compound represented by the formula (4B).
  • the obtained 2-halogenated-9-substituted carbazole compound represented by the formula (4B) and the secondary amine compound represented by the formula (5B) are combined with a copper catalyst or a palladium catalyst in the presence of a base. To react.
  • the compound represented by the formula (2B) can be synthesized based on a generally known method (for example, Japanese Patent Application Laid-Open No. 2011-1349).
  • the compound represented by the formula (3B) can be synthesized based on a generally known method (for example, WO 2009-133007 and Chemistry Letters, 2011, 40, 1050).
  • a commercially available compound can be used, or it can be synthesized based on a generally known method.
  • the 2-aminocarbazole compound represented by the formula (1B) of the present invention can be used as a light emitting layer, a hole transport layer or a hole injection layer of an organic EL device. That is, the compound represented by the formula (1B) can be effectively used as a light emitting material, a light emitting host material, a hole transport material, or a hole injection material.
  • the said compound is high purity at the point of a hole transport characteristic and an organic EL element lifetime. It can be purified by a generally known method such as distillation, sublimation purification, recrystallization, silica gel chromatography, and the like, and can be highly purified.
  • the 2-aminocarbazole compound represented by the formula (1B) is used as a hole injection layer and / or a hole transport layer of an organic EL device
  • a known fluorescence that has been conventionally used is used.
  • a phosphorescent material can be used.
  • the light emitting layer may be formed of only one kind of light emitting material, or one or more kinds of light emitting materials may be doped in the host material.
  • two or more kinds of materials may be contained or laminated as necessary. Also good.
  • oxides such as molybdenum oxide, 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, hexacyanohexa
  • a known electron-accepting material such as azatriphenylene may be contained or laminated.
  • the 2-aminocarbazole compound represented by the formula (1B) is used as a light emitting layer of an organic EL device, it is used by doping the known light emitting host material, which uses the 2-aminocarbazole compound alone. Or doped with a known light-emitting dopant.
  • Examples of a method for forming a hole injection layer, a hole transport layer, or a light emitting layer containing the 2-aminocarbazole compound represented by the formula (1B) include a vacuum deposition method, a spin coating method, and a casting method. A known method can be applied.
  • Example 1A (Synthesis of Compound (A25)) In a 100 mL three-necked flask under a nitrogen stream, 8.0 g (19.8 mmol) of 2-chloro-9- (4- (1-naphthyl) phenyl) carbazole obtained in Synthesis Example 1A, N, N-bis (4- Biphenyl) amine 6.3 g (19.8 mmol), sodium tert-butoxide 2.6 g (27.7 mmol), o-xylene 45 mL, palladium acetate 44 mg (0.19 mmol), and tri (tert-butyl) phosphine 139 mg ( 0.69 mmol) was added and the mixture was stirred at 140 ° C.
  • Example 2A (Synthesis of Compound (A26)) In a 50 mL three-necked flask under a nitrogen stream, 3.5 g (8.3 mmol) of 2-chloro-9- (4- (2-methylnaphthalen-1-yl) phenyl) carbazole obtained in Synthesis Example 2A, N, N -Bis (4-biphenyl) amine 2.7 g (8.3 mmol), sodium-tert-butoxide 1.1 g (11.7 mmol), o-xylene 20 mL, palladium acetate 18 mg (0.08 mmol), and tri (tert- Butyl) phosphine 59 mg (0.29 mmol) was added, and the mixture was stirred at 140 ° C.
  • Example 3A (Synthesis of Compound (A27)) In a 100 mL three-necked flask under a nitrogen stream, 5.0 g (12.4 mmol) of 2-chloro-9- (3- (1-naphthyl) phenyl) carbazole obtained in Synthesis Example 3A, N, N-bis (4- 3.9 g (12.4 mmol) of biphenyl) amine, 1.6 g (17.3 mmol) of sodium-tert-butoxide, 30 mL of o-xylene, 27 mg (0.12 mmol) of palladium acetate, and 87 mg of tri (tert-butyl) phosphine 0.43 mmol) was added and the mixture was stirred at 140 ° C.
  • Example 4A (Synthesis of Compound (A28)) In a 100 mL three-necked flask under a nitrogen stream, 10.0 g (23.9 mmol) of 2-chloro-9- (3- (2-methylnaphthalen-1-yl) phenyl) carbazole obtained in Synthesis Example 4A, N, N Bis (4-biphenyl) amine 7.6 g (23.9 mmol), sodium-tert-butoxide 3.2 g (33.5 mmol), o-xylene 50 mL, palladium acetate 75 mg (0.12 mmol), and tri (tert- Butyl) phosphine (236 mg, 1.1 mmol) was added, and the mixture was stirred at 140 ° C.
  • Example 5A (Synthesis of Compound (A29)) In a 50 mL three-necked flask under a nitrogen stream, 4.0 g (9.9 mmol) of 2-chloro-9- (4- (1-naphthyl) phenyl) carbazole obtained in Synthesis Example 1A, N-phenyl-N- (p -Terphenyl-4-yl) amine 3.1 g (9.9 mmol), sodium-tert-butoxide 1.3 g (13.8 mmol), o-xylene 25 mL, palladium acetate 22 mg (0.09 mmol), and tri (tert -Butyl) phosphine 69 mg (0.34 mmol) was added and stirred at 140 ° C.
  • Example 6A (Synthesis of Compound (A47)) In a 50 mL three-necked flask under a nitrogen stream, 1.0 g (2.4 mmol) of 2-chloro-9- (3- (1-naphthyl) phenyl) carbazole obtained in Synthesis Example 3A, N- (4-biphenyl)- N- (m-terphenyl-4-yl) amine 0.98 g (2.4 mmol), sodium-tert-butoxide 0.32 g (3.4 mmol), o-xylene 10 mL, palladium acetate 5 mg (0.02 mmol), Then, 17 mg (0.08 mmol) of tri (tert-butyl) phosphine was added, and the mixture was stirred at 140 ° C.
  • Example 7A (Synthesis of Compound (A53)) In a 50 mL three-necked flask under a nitrogen stream, 2.5 g (6.2 mmol) of 2-chloro-9- (4- (1-naphthyl) phenyl) carbazole obtained in Synthesis Example 1A, N-phenyl-N- (9 , 9-dimethylfluoren-2-yl) amine 1.7 g (6.2 mmol), sodium tert-butoxide 0.8 g (8.6 mmol), o-xylene 15 mL, palladium acetate 13 mg (0.06 mmol), and tri 43 mg (0.21 mmol) of (tert-butyl) phosphine was added, and the mixture was stirred at 140 ° C.
  • Example 1B (Synthesis of Compound (B25)) In a 100 mL three-necked flask under a nitrogen stream, 5.5 g (11.9 mmol) of 2-chloro-9- (4- (4-dibenzothienyl) phenyl) carbazole obtained in Synthesis Example 1B, N, N-bisbiphenylamine 3.8 g (11.9 mmol), sodium-tert-butoxide 1.6 g (16.7 mmol), o-xylene 35 mL, palladium acetate 53 mg (0.23 mmol), and tri (tert-butyl) phosphine 162 mg (0.80 mmol) ) And stirred at 140 ° C. for 6 hours.
  • Example 2B (Synthesis of Compound (B26)) In a 50 mL three-necked flask under a nitrogen stream, 5.0 g (11.2 mmol) of 2-chloro-9- (4- (4-dibenzofuranyl) phenyl) carbazole obtained in Synthesis Example 2B, N, N-bisbiphenyl 3.6 g (11.2 mmol) of amine, 1.5 g (15.7 mmol) of sodium-tert-butoxide, 25 mL of o-xylene, 50 mg (0.22 mmol) of palladium acetate, and 155 mg (0. 0 of tri (tert-butyl) phosphine).
  • Example 3B (Synthesis of Compound (B27)) In a 50 mL three-necked flask under a nitrogen stream, 1.8 g (3.9 mmol) of 2-chloro-9- (3- (4-dibenzothienyl) phenyl) carbazole obtained in Synthesis Example 3B, N, N-bisbiphenylamine 1.2 g (3.9 mmol), sodium-tert-butoxide 0.5 g (5.5 mmol), o-xylene 10 mL, palladium acetate 17 mg (0.07 mmol), and tri (tert-butyl) phosphine 54 mg (0.26 mmol) ) was added and stirred at 140 ° C. for 3 hours.
  • Example 4B (Synthesis of Compound (B28)) In a 50 mL three-necked flask under a nitrogen stream, 3.0 g (6.7 mmol) of 2-chloro-9- (3- (4-dibenzofuranyl) phenyl) carbazole obtained in Synthesis Example 4B, N, N-bisbiphenyl 2.1 g (6.7 mmol) of amine, 0.90 g (9.4 mmol) of sodium-tert-butoxide, 15 mL of o-xylene, 30 mg (0.13 mmol) of palladium acetate, and 93 mg of tri (tert-butyl) phosphine 46 mmol) was added and stirred at 140 ° C.
  • Example 5B (Synthesis of Compound (B29)) In a 50 mL three-necked flask under a nitrogen stream, 1.1 g (2.3 mmol) of 2-chloro-9- (4- (4-dibenzothienyl) phenyl) carbazole obtained in Synthesis Example 1B, N-phenyl-N— ( p-terphenylamine) 0.73 g (2.3 mmol), sodium tert-butoxide 0.32 g (3.3 mmol), o-xylene 10 mL, palladium acetate 10 mg (0.04 mmol), and tri (tert-butyl) 32 mg (0.26 mmol) of phosphine was added and stirred at 140 ° C.
  • Example 6B (Synthesis of Compound (B34)) In a 50 mL three-necked flask under a nitrogen stream, 2.5 g (5.6 mmol) of 2-chloro-9- (4- (4-dibenzofuranyl) phenyl) carbazole obtained in Synthesis Example 2B, N-biphenyl-N— 2.2 g (5.6 mmol) of (p-terphenyl) amine, 0.75 g (7.8 mmol) of sodium-tert-butoxide, 15 mL of o-xylene, 25 mg (0.11 mmol) of palladium acetate, and tri (tert-butyl) ) 77 mg (0.38 mmol) of phosphine was added and stirred at 140 ° C.
  • Example 7B (Synthesis of Compound (B46)) In a 50 mL three-necked flask under a nitrogen stream, 1.0 g (2.2 mmol) of 2-chloro-9- (4- (4-dibenzofuranyl) phenyl) carbazole obtained in Synthesis Example 2B, N-biphenyl-N— (M-Terphenyl) amine 0.88 g (2.2 mmol), sodium-tert-butoxide 0.3 g (3.1 mmol), o-xylene 10 mL, palladium acetate 10 mg (0.04 mmol), and tri (tert-butyl) ) 31 mg (0.15 mmol) of phosphine was added and stirred at 140 ° C.
  • Example 8B (Synthesis of Compound (B53)) In a 50 mL three-necked flask under a nitrogen stream, 1.1 g (2.3 mmol) of 2-chloro-9- (4- (4-dibenzothienyl) phenyl) carbazole obtained in Synthesis Example 1B, N-phenyl-N— ( 9,9-dimethylfluoren-2-yl) amine 0.65 g (2.3 mmol), sodium tert-butoxide 0.32 g (3.3 mmol), o-xylene 10 mL, palladium acetate 10 mg (0.04 mmol), and 32 mg (0.16 mmol) of tri (tert-butyl) phosphine was added, and the mixture was stirred at 140 ° C.
  • Example 9B (Synthesis of Compound (B77)) In a 50 mL three-necked flask under nitrogen flow, 4.0 g (8.7 mmol) of 2-chloro-6- (4-dibenzothienyl) -9-phenylcarbazole obtained in Synthesis Example 7B, N, N-bisbiphenylamine 2 0.8 g (8.7 mmol), sodium-tert-butoxide 1.1 g (12.1 mmol), o-xylene 25 mL, palladium acetate 19 mg (0.08 mmol), and tri (tert-butyl) phosphine 56 mg (0.28 mmol) was added and stirred at 140 ° C. for 16 hours.
  • Example 10B (Synthesis of Compound (B79)) In a 50 mL three-necked flask under a nitrogen stream, 1.2 g (2.6 mmol) of 2-chloro-6- (4-dibenzothienyl) -9-phenylcarbazole obtained in Synthesis Example 7B and N-phenyl-N- (p -Terphenylamine) 0.8 g (2.6 mmol), sodium tert-butoxide 0.33 g (3.6 mmol), o-xylene 10 mL, palladium acetate 5 mg (0.02 mmol), and tri (tert-butyl) phosphine 16 mg (0.08 mmol) was added, and the mixture was stirred at 140 ° C.
  • Example 11B (Synthesis of Compound (B2)) In a 50 mL three-necked flask under a nitrogen stream, 1.0 g (2.2 mmol) of 2-chloro-9- (4- (4-dibenzofuranyl) phenyl) carbazole obtained in Synthesis Example 2B, N-phenyl-N— (1-Naphtyl) amine 0.48 g (2.2 mmol), sodium-tert-butoxide 0.3 g (3.1 mmol), o-xylene 10 mL, palladium acetate 10 mg (0.04 mmol), and tri (tert-butyl) 31 mg (0.15 mmol) of phosphine was added and stirred at 140 ° C.
  • Example 12B (Synthesis of Compound (B5)) In a 50 mL three-necked flask under a nitrogen stream, 4.0 g (8.7 mmol) of 2-chloro-9- (4- (4-dibenzothienyl) phenyl) carbazole obtained in Synthesis Example 1B, N-phenyl-N— ( 9-phenanthryl) amine 2.3 g (8.7 mmol), sodium-tert-butoxide 1.1 g (12.1 mmol), o-xylene 25 mL, palladium acetate 19 mg (0.08 mmol), and tri (tert-butyl) phosphine 56 mg (0.28 mmol) was added, and the mixture was stirred at 140 ° C.
  • Example 13B (Synthesis of Compound (B103)) In a 100 mL three-necked flask under a nitrogen stream, 1.0 g (2.2 mmol) of 2-chloro-9- (4- (9-phenanthryl) phenyl) carbazole obtained in Synthesis Example 8B, N- (4-methylphenyl) -N- (4-biphenyl) amine 0.57 g (2.2 mmol), sodium-tert-butoxide 0.28 g (3.0 mmol), o-xylene 10 mL, palladium acetate 5 mg (0.02 mmol), and tri (tert -Butyl) phosphine 15 mg (0.07 mmol) was added, and the mixture was stirred at 140 ° C.
  • Example 14B (Synthesis of Compound (B106)) In a 100 mL three-necked flask under a nitrogen stream, 7.0 g (15.4 mmol) of 2-chloro-9- (4- (9-phenanthryl) phenyl) carbazole obtained in Synthesis Example 8B, N, N-bis (4- Biphenyl) amine 4.6 g (15.4 mmol), sodium-tert-butoxide 2.0 g (21.6 mmol), o-xylene 35 mL, palladium acetate 34 mg (0.15 mmol), and tri (tert-butyl) phosphine 108 mg ( 0.54 mmol) was added and the mixture was stirred at 140 ° C. for 9 hours.
  • Example 15B (Synthesis of Compound (B122)) In a 100 mL three-necked flask under a nitrogen stream, 8.0 g (17.6 mmol) of 2-chloro-9- (3- (9-phenanthryl) phenyl) carbazole obtained in Synthesis Example 9B, N, N-bis (4- Biphenyl) amine 5.3 g (17.6 mmol), sodium-tert-butoxide 2.3 g (17.6 mmol), o-xylene 40 mL, palladium acetate 39 mg (0.0.17 mmol), and tri (tert-butyl) phosphine 124 mg (0.61 mmol) was added and stirred at 140 ° C. for 10 hours.
  • Example 16B (Synthesis of Compound (B138)) In a 100 mL three-necked flask under a nitrogen stream, 5.5 g (12.1 mmol) of 2-chloro-6- (9-phenanthryl) -9-phenylcarbazole obtained in Synthesis Example 12B, N, N-bis (4-biphenyl) ) Amine 3.8 g (12.1 mmol), sodium-tert-butoxide 1.6 g (16.7 mmol), o-xylene 30 mL, palladium acetate 27 mg (0.12 mmol), and tri (tert-butyl) phosphine 85 mg (0 .42 mmol) was added and stirred at 140 ° C. for 11 hours.
  • Example 8A device evaluation of compound (A25)
  • the glass substrate on which the ITO transparent electrode (anode) having a thickness of 200 nm was laminated was subjected to ultrasonic cleaning with acetone and pure water and boiling cleaning with isopropyl alcohol. Further, UV / ozone cleaning was performed, and after installation in a vacuum deposition apparatus, the vacuum pump exhausted until 1 ⁇ 10 ⁇ 4 Pa.
  • copper phthalocyanine is deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / second to form a 10 nm hole injection layer.
  • the compound (A25) is deposited at a deposition rate of 0.3 nm / second to 30 nm to form holes.
  • BAlq bis (2-methyl-8-quinolinolato) (p-phenylphenolate) aluminum
  • Alq 3 Tris (8-quinolinolato) aluminum
  • lithium fluoride was deposited as an electron injection layer by 1 nm at a deposition rate of 0.01 nm / second
  • aluminum was deposited by 100 nm at a deposition rate of 0.25 nm / second to form a cathode.
  • Examples 9A to 14A (element evaluation) An organic EL device was prepared in the same manner as in Example 8A, except that compound (A26), (A27), (A28), (A29), (A47), or (A53) was used instead of compound (A25). Produced. Table 1 summarizes the driving voltage and current efficiency when a current of 20 mA / cm 2 was applied, and the luminance half-time when a current of 6.25 mA / cm 2 was applied.
  • Examples 17B to 41B (Element evaluation) Instead of the compound (A25), the compounds (B25), (B26), (B27), (B28), (B29), (B34), (B46), (B53), (B77), (B79), ( B2), (B5), (B103), (B106), (B122) or an organic EL element was produced in the same manner as in Example 8A, except that it was changed to (B138).
  • Table 1 summarizes the driving voltage and current efficiency when a current of 20 mA / cm 2 was applied, and the luminance half-time when a current of 6.25 mA / cm 2 was applied.
  • Comparative Example 1 An organic EL device was produced in the same manner as in Example 8A, except that the compound (A25) was changed to NPD (4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl).
  • Table 1 shows the driving voltage and current efficiency when a current of 20 mA / cm 2 was applied, and the luminance half time when a current of 6.25 mA / cm 2 was applied.
  • Comparative Example 2 (device evaluation of compound (a)) An organic EL device was produced in the same manner as in Example 8A, except that the compound (A25) was changed to the following compound (a).
  • Table 1 shows the driving voltage and current efficiency when a current of 20 mA / cm 2 was applied, and the luminance half time when a current of 6.25 mA / cm 2 was applied.
  • Reference Example 1 (device evaluation of compound (b)) An organic EL device was produced in the same manner as in Example 8A, except that the compound (A25) was changed to the following compound (b). Table 1 shows the driving voltage and current efficiency when a current of 20 mA / cm 2 was applied, and the luminance half time when a current of 6.25 mA / cm 2 was applied.
  • the organic EL device using the 2-aminocarbazole compound of the present invention can be used as an organic EL material that is remarkably excellent in device lifetime and excellent in durability.
  • an organic EL device using the 2-aminocarbazole compound of the present invention as a hole transport material can have a long lifetime, a low driving voltage, and a high luminous efficiency, and has low power consumption and a long lifetime. It can be used in the display field such as portable devices.

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Abstract

Cette invention concerne : un composé de 2-aminocarbazole pouvant être utilisé à titre de matériau de transport de trous pour un élément EL organique ; et un élément EL organique produit à l'aide dudit composé et ayant une tension de commande, un rendement lumineux et une durée de vie d'élément qui sont excellents. Un composé de 2-aminocarbazole représenté par la formule (1) est en outre décrit. (Dans la Formule (1), R représente un atome d'hydrogène ou un groupe méthyle ; un des R1 à R3 représente un groupe 4-dibenzothiényle, un groupe 4-dibenzofuranyle, un groupe 9-phénanthryle, ou un substituant représenté par la formule (2) (où R représente un atome d'hydrogène ou un groupe méthyle), les autres représentant indépendamment un atome d'hydrogène ou un groupe méthyle ; et Ar1 et Ar2 représentent indépendamment un groupe hydrocarbure aromatique ayant de 6 à 18 atomes de carbone, le groupe hydrocarbure aromatique pouvant contenir un groupe méthyle ou un groupe méthoxy).
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JP2019508410A (ja) * 2016-02-29 2019-03-28 エルジー・ケム・リミテッド 含窒素化合物およびこれを含む有機発光素子

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