[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

WO2012060374A1 - Matériau de transport des électrons et élément électroluminescent organique l'employant - Google Patents

Matériau de transport des électrons et élément électroluminescent organique l'employant Download PDF

Info

Publication number
WO2012060374A1
WO2012060374A1 PCT/JP2011/075179 JP2011075179W WO2012060374A1 WO 2012060374 A1 WO2012060374 A1 WO 2012060374A1 JP 2011075179 W JP2011075179 W JP 2011075179W WO 2012060374 A1 WO2012060374 A1 WO 2012060374A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
represented
formula
formulas
carbons
Prior art date
Application number
PCT/JP2011/075179
Other languages
English (en)
Japanese (ja)
Inventor
洋平 小野
馬場　大輔
Original Assignee
Jnc株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jnc株式会社 filed Critical Jnc株式会社
Priority to KR1020137011642A priority Critical patent/KR101835020B1/ko
Priority to JP2012541874A priority patent/JP5737294B2/ja
Priority to CN201180052069.3A priority patent/CN103189355B/zh
Publication of WO2012060374A1 publication Critical patent/WO2012060374A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO

Definitions

  • the present invention relates to a novel electron transport material having a pyridyl group, an organic electroluminescence device using the electron transport material (hereinafter, sometimes abbreviated as an organic EL device or simply a device), and the like.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2003-123983 discloses that an organic EL device can be driven at a low voltage by using a 2,2′-bipyridyl compound, which is a phenanthroline derivative or an analog thereof, as an electron transport material. It is stated that it can be done.
  • Non-patent document 1 Non-patent document 1 (Proceedings of the 10 th International Workshop on Inorganic and Organic Electroluminescence), Patent Document 2 (JP 2002-158093 JP ) And Patent Document 3 (International Publication No. 2007/86552 pamphlet).
  • the compound described in Non-Patent Document 1 has a low Tg and is not practical.
  • the compounds described in Patent Documents 2 and 3 can drive an organic EL device at a relatively low voltage, longer life is desired for practical use.
  • the present invention has been made in view of the problems of such conventional techniques. It is an object of the present invention to provide an electron transport material that contributes to extending the lifetime of an organic EL element. Furthermore, this invention makes it a subject to provide the organic EL element using this electron transport material.
  • naphthyl or phenyl of 9- (2-naphthyl) -10-phenylanthracene has pyridyl, bipyridyl, or pyridylphenyl, and a benzene ring or naphthalene ring.
  • a compound in which at least one of hydrogen of the pyridine ring is substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms for an electron transport layer of an organic EL device and can be driven with a long lifetime It was found that an element was obtained, and the present invention was completed based on this finding. Said subject is solved by each item shown below.
  • At least one of the electron transport layer and the electron injection layer further includes an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, or an alkaline earth. Containing at least one selected from the group consisting of metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes The organic electroluminescent element according to the above [16] or [17].
  • the compound of the present invention is stable even when a voltage is applied in a thin film state and has a feature of high charge transport capability.
  • the compound of the present invention is suitable as a charge transport material in an organic EL device.
  • an organic EL device having a long lifetime can be obtained.
  • a high-performance display device such as full-color display can be created.
  • the first invention of the present application is a compound having pyridyl, bipyridyl or pyridylphenyl represented by the following formula (1).
  • a feature of the present compound is that at least one of hydrogen in the benzene ring, naphthalene ring and pyridine ring in the formula (1) is replaced with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms. It is.
  • the pyridyl represented by the formula (2) is specifically 2-pyridyl, 3-pyridyl or 4-pyridyl.
  • Bipyridyl represented by the formula (3) is specifically 2,2′-bipyridin-5-yl, 2,2′-bipyridin-6-yl, 2,2′-bipyridin-4-yl, 2, 3'-bipyridin-5-yl, 2,3'-bipyridin-6-yl, 2,3'-bipyridin-4-yl, 2,4'-bipyridin-5-yl, 2,4'-bipyridine-6 -Yl, 2,4'-bipyridin-4-yl, 3,2'-bipyridin-6-yl, 3,2'-bipyridin-5-yl, 3,3'-bipyridin-6-yl, 3,3 '-Bipyridin-5-yl, 3,4'-bipyridin-6-yl, 3,4'-bipyridin-5-yl, 4,2'-bipyridin-3-yl, 4,3'-bipyridine-3- Or 4,4′-b
  • pyridylphenyl represented by the formula (4) include 4- (2-pyridyl) phenyl, 4- (3-pyridyl) phenyl, 4- (4-pyridyl) phenyl, and 3- (2-pyridyl). It is phenyl, 3- (3-pyridyl) phenyl, 3- (4-pyridyl) phenyl, 2- (2-pyridyl) phenyl, 2- (3-pyridyl) phenyl, or 2- (4-pyridyl) phenyl.
  • Py may be linked at any position in phenyl or 2-naphthyl, but 4-position and 3-position are preferable in phenyl, and 6-position and 7-position in 2-naphthyl are preferable.
  • the 3-position of phenyl is preferable in that the conjugated system cannot be expanded and the LUMO level is not lowered.
  • the 6-position of 2-naphthyl is particularly preferable in view of easy availability of raw materials.
  • alkyl having 1 to 6 carbon atoms substituted on the benzene ring, naphthalene ring and pyridine ring in the formula (1) are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n- Pentyl, isopentyl, 2,2-dimethylpropyl, n-hexyl, and isohexyl.
  • preferred alkyls are methyl, ethyl, isopropyl, and t-butyl, with methyl and t-butyl being more preferred.
  • cycloalkyl having 3 to 6 carbon atoms examples include cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Of these, cycloalkyl is preferably cyclohexyl in view of availability of raw materials and ease of synthesis.
  • the compound represented by the formula (1) is specifically a compound represented by the following formula (1-1) or (1-2).
  • the definition of Py in the formulas (1-1) and (1-2) is the same as described above.
  • the compound represented by the formula (1) is a compound represented by any one of the following formulas (1-3) to (1-6).
  • the definition of Py in the formulas (1-3) to (1-6) is the same as described above.
  • the compound represented by the formula (1) is a compound represented by any one of the following formulas (1-7) to (1-10).
  • Py and R are as defined above.
  • p is an integer of 1 to 5, preferably an integer of 1 to 2, and more preferably 1.
  • the position of phenyl substituted by R is not limited, but the 3-position or 4-position is preferred.
  • Q in the formulas (1-9) and (1-10) is an integer of 1 to 5, preferably an integer of 1 to 2, and more preferably 1.
  • limiting in the position of the naphthyl which R substitutes It is preferable that it is 6th-position or 7th-position.
  • the compound represented by the formula (1) is more specifically a compound represented by any of the following formulas (1-11) to (1-14).
  • the definition of Py 1 is the same as described above.
  • the definition of R in the above formula (2 ′), (3 ′) or (4 ′) is the same as described above.
  • s is an integer of 1 to 4, preferably 1 or 2, and more preferably 1.
  • the position of pyridyl substituted by R is not particularly limited.
  • the compound represented by the formula (1) is more specifically a compound represented by the following formula (1-15) or (1-16).
  • the definitions of Py and R in the formulas (1-15) and (1-16) are the same as described above.
  • t is an integer of 1 to 4, preferably 1 or 2, and more preferably 1.
  • phenylene substituted by R there is no restriction on the position of phenylene substituted by R, but considering the ease of synthesis, in the case of 1,4-phenylene, the 3-position is preferred based on the carbon linked to anthracene. In the case of 1,3-phenylene, the 4-position is preferred based on the carbon linked to the anthracene.
  • the compounds represented by the formula (1) are roughly classified into compounds represented by the formulas (1-7) to (1-16).
  • preferred structures are formulas (1-7), formulas (1-9) to (1-11), and formulas (1-13) to (1-16), and more preferred structures are formulas (1- 7).
  • Specific examples of the compound represented by the formula (1-7) are represented by the following formulas (1-7-1) to (1-7-144). Of these, preferred compounds are those represented by formulas (1-7-1) to (1-7-6), formulas (1-7-10) to (1-7-12), formulas (1-7-16) to (1-7-30), formulas (1-7-34) to (1-7-36), formulas (1-7-40) to (1-7-48), formula (1-7-73) To (1-7-78), formulas (1-7-82) to (1-7-84), formulas (1-7-88) to (1-7-102), formulas (1-7-106) ) To (1-7-108) and formulas (1-7-112) to (1-7-120).
  • Specific examples of the compound represented by the formula (1-15) are represented by the following formulas (1-15-1) to (1-15-48). Of these, preferred compounds are those represented by formulas (1-15-10) to (1-15-12), (1-15-16) to (1-15-18), and formulas (1-15-34) to ( 1-15-36) and (1-15-40) to (1-15-42).
  • the coupling of the benzene ring and the anthracene ring is not limited to the above method, and for example, the Negishi coupling reaction using a zinc complex, the Suzuki coupling reaction using a boronic acid or a boronic acid ester, and the like are also possible. These conventional methods can be appropriately used depending on the case.
  • N-bromosuccinimide is used to bromine the 10-position of 9-phenylanthracene in which phenyl is substituted with an alkyl group (cycloalkyl group).
  • a commonly used brominating agent other than N-bromosuccinimide can be used.
  • reaction 3 the anthracene ring and the naphthalene ring are coupled.
  • 2-bromo-6-methoxynaphthalene is converted into a Grignard reagent according to a conventional method, and this is reacted with the 9-bromoanthracene derivative synthesized in Reaction 2 in the presence of a catalyst to give 9- (6-methoxynaphthalen-2-yl)-
  • a 10-phenylanthracene derivative is synthesized.
  • coupling of the benzene ring and the anthracene ring is not limited to the above method.
  • Negishi coupling reaction using a zinc complex Suzuki coupling reaction using a boronic acid or a boronic acid ester, and the like.
  • Reaction 6 a pyridine ring is bonded to the naphthalene ring by Negishi coupling reaction.
  • 4-bromopyridine is used as a Grignard reagent.
  • isopropylmagnesium chloride is used in an amount of 2 moles.
  • a raw material which does not need to use hydrochloride may be used in an equimolar amount.
  • a zinc chloride tetramethylethylenediamine complex is added to a Grignard reagent to synthesize a zinc chloride complex of pyridine, and this is reacted with the triflate obtained in the reaction 5 in the presence of a palladium catalyst to synthesize a target product.
  • Reaction 6 in addition to the Negishi coupling reaction, a commonly used coupling reaction such as a Suzuki coupling reaction can be appropriately used.
  • a commonly used coupling reaction such as a Suzuki coupling reaction
  • an optimal boronic acid or boronic acid ester may be prepared according to the target product.
  • the target product can be obtained using a boronic acid ester as shown in the following reaction 7. .
  • the palladium catalyst used in the coupling reaction include Pd (PPh 3 ) 4 , PdCl 2 (PPh 3 ) 2 , Pd (OAc) 2 , tris (dibenzylideneacetone) dipalladium (0), tris (di) Benzylideneacetone) dipalladium (0) chloroform complex, bis (dibenzylideneacetone) palladium (0), bis (tri-t-butylphosphino) palladium (0), or (1,1′-bis (diphenylphosphino) ferrocene ) Dichloropalladium (II).
  • a phosphine compound may be added to these palladium compounds in some cases.
  • the phosphine compound include tri (t-butyl) phosphine, tricyclohexylphosphine, 1- (N, N-dimethylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (N, N-dibutylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (methoxymethyl) -2- (di-t-butylphosphino) ferrocene, 1,1′-bis (di-t-butylphos Fino) ferrocene, 2,2′-bis (di-t-butylphosphino) -1,1′-binaphthyl, 2-methoxy-2 ′-(di-t-butylphosphino) -1,1′-binaphthy
  • the base used in the reaction include sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium t-butoxide, sodium acetate, phosphoric acid
  • Examples include tripotassium or potassium fluoride.
  • solvent used in the reaction examples include benzene, toluene, xylene, 1,2,4-trimethylbenzene, N, N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butyl methyl ether, 1,4- Examples include dioxane, methanol, ethanol, cyclopentyl methyl ether, and isopropyl alcohol. These solvents can be appropriately selected and may be used alone or as a mixed solvent.
  • a pyridine derivative substituted with an alkyl group or a cycloalkyl group can be synthesized as shown in Reactions 8 to 9 below.
  • a method for synthesizing a pyridine moiety in the compounds represented by formula (1-11-1), formula (1-12-111), formula (1-13-111) and formula (1-14-11) is illustrated.
  • pyridine derivatives substituted with various alkyl groups or cycloalkyl groups can be synthesized by appropriately changing the raw materials.
  • the compound of the present invention When the compound of the present invention is used for an electron injection layer or an electron transport layer in an organic EL device, it is stable when an electric field is applied. These represent that the compound of the present invention is excellent as an electron injecting material or an electron transporting material for an electroluminescent device.
  • the electron injection layer mentioned here is a layer for receiving electrons from the cathode to the organic layer
  • the electron transport layer is a layer for transporting the injected electrons to the light emitting layer.
  • the electron transport layer can also serve as the electron injection layer.
  • the material used for each layer is referred to as an electron injection material and an electron transport material.
  • 2nd invention of this application is an organic EL element containing the compound represented by Formula (1) of this invention in an electron injection layer or an electron carrying layer.
  • the organic EL element of the present invention has a low driving voltage and high durability during driving.
  • the structure of the organic EL device of the present invention has various modes, it is basically a multilayer structure in which at least a hole transport layer, a light emitting layer, and an electron transport layer are sandwiched between an anode and a cathode.
  • Examples of the specific configuration of the device are (1) anode / hole transport layer / light emitting layer / electron transport layer / cathode, (2) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer. / Cathode, (3) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode, etc.
  • the compound of the present invention Since the compound of the present invention has high electron injecting property and electron transporting property, it can be used for an electron injecting layer or an electron transporting layer alone or in combination with other materials.
  • the organic EL device of the present invention emits blue, green, red and white light by combining a hole injection layer, a hole transport layer, a light emitting layer, etc. using other materials with the electron transport material of the present invention. It can also be obtained.
  • the light-emitting material or light-emitting dopant that can be used in the organic EL device of the present invention is daylight fluorescence as described in the Polymer Society of Japan, Polymer Functional Materials Series “Optical Functional Materials”, Joint Publication (1991), P236. Materials, fluorescent brighteners, laser dyes, organic scintillators, various fluorescent analysis reagents and other luminescent materials, supervised by Koji Koji, “Organic EL materials and displays” published by CMMC (2001) P155-156 And a light emitting material of a triplet material as described in P170 to 172.
  • the compounds that can be used as the light emitting material or the light emitting dopant are polycyclic aromatic compounds, heteroaromatic compounds, organometallic complexes, dyes, polymer light emitting materials, styryl derivatives, aromatic amine derivatives, coumarin derivatives, borane derivatives, oxazines. Derivatives, compounds having a spiro ring, oxadiazole derivatives, fluorene derivatives and the like.
  • Examples of the polycyclic aromatic compound are anthracene derivatives, phenanthrene derivatives, naphthacene derivatives, pyrene derivatives, chrysene derivatives, perylene derivatives, coronene derivatives, rubrene derivatives, and the like.
  • heteroaromatic compounds are oxadiazole derivatives having a dialkylamino group or diarylamino group, pyrazoloquinoline derivatives, pyridine derivatives, pyran derivatives, phenanthroline derivatives, silole derivatives, thiophene derivatives having a triphenylamino group, quinacridone derivatives Etc.
  • organometallic complexes examples include zinc, aluminum, beryllium, europium, terbium, dysprosium, iridium, platinum, osmium, gold, etc., quinolinol derivatives, benzoxazole derivatives, benzothiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, A complex with a benzimidazole derivative, a pyrrole derivative, a pyridine derivative, a phenanthroline derivative, or the like.
  • dyes are xanthene derivatives, polymethine derivatives, porphyrin derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, oxobenzanthracene derivatives, carbostyril derivatives, perylene derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazoles And pigments such as derivatives.
  • the polymer light-emitting material are polyparaphenyl vinylene derivatives, polythiophene derivatives, polyvinyl carbazole derivatives, polysilane derivatives, polyfluorene derivatives, polyparaphenylene derivatives, and the like.
  • styryl derivatives are amine-containing styryl derivatives, styrylarylene derivatives, and the like.
  • electron transport materials used in the organic EL device of the present invention are arbitrarily selected from compounds that can be used as electron transport compounds in photoconductive materials and compounds that can be used in the electron transport layer and electron injection layer of organic EL devices. Can be used.
  • electron transport materials include quinolinol metal complexes, 2,2′-bipyridyl derivatives, phenanthroline derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, oxine derivatives.
  • a compound conventionally used as a charge transport material for holes or a hole injection of an organic EL device is used in a photoconductive material.
  • Any known material used for the layer and the hole transport layer can be selected and used. Specific examples thereof are carbazole derivatives, triarylamine derivatives, phthalocyanine derivatives and the like.
  • Each layer constituting the organic EL element of the present invention can be formed by forming a material to constitute each layer into a thin film by a method such as a vapor deposition method, a spin coat method, or a cast method.
  • the film thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm.
  • a vapor deposition method as a method of thinning the light emitting material from the viewpoint that a homogeneous film can be easily obtained and pinholes are hardly generated.
  • the vapor deposition conditions differ depending on the type of the light emitting material of the present invention.
  • Deposition conditions generally include boat heating temperature 50 to 400 ° C., vacuum degree 10 ⁇ 6 to 10 ⁇ 3 Pa, deposition rate 0.01 to 50 nm / second, substrate temperature ⁇ 150 to + 300 ° C., film thickness 5 nm to 5 ⁇ m. It is preferable to set appropriately within the range.
  • the organic EL device of the present invention is preferably supported by a substrate in any of the structures described above.
  • the substrate only needs to have mechanical strength, thermal stability, and transparency, and glass, a transparent plastic film, and the like can be used.
  • the anode material metals, alloys, electrically conductive compounds and mixtures thereof having a work function larger than 4 eV can be used. Specific examples thereof include metals such as Au, CuI, indium tin oxide (hereinafter abbreviated as ITO), SnO 2 , ZnO, and the like.
  • Cathode materials can use metals, alloys, electrically conductive compounds, and mixtures thereof with work functions of less than 4 eV. Specific examples thereof are aluminum, calcium, magnesium, lithium, magnesium alloy, aluminum alloy and the like. Specific examples of the alloy include aluminum / lithium fluoride, aluminum / lithium, magnesium / silver, and magnesium / indium. In order to efficiently extract light emitted from the organic EL element, it is desirable that at least one of the electrodes has a light transmittance of 10% or more.
  • the sheet resistance as the electrode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the properties of the electrode material, it is usually set in the range of 10 nm to 1 ⁇ m, preferably 10 to 400 nm.
  • Such an electrode can be produced by forming a thin film by a method such as vapor deposition or sputtering using the electrode material described above.
  • an organic material comprising the above-mentioned anode / hole injection layer / hole transport layer / light emitting layer / electron transport material of the present invention / cathode is used.
  • a method for creating an EL element will be described.
  • a thin film of an anode material is formed on a suitable substrate by vapor deposition to produce an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode.
  • a light emitting layer thin film is formed thereon.
  • the electron transport material of this invention is vacuum-deposited, a thin film is formed, and it is set as an electron carrying layer.
  • the target organic EL element is obtained by forming the thin film which consists of a substance for cathodes by a vapor deposition method, and making it a cathode.
  • the production order can be reversed, and the cathode, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode can be produced in this order.
  • the anode When a DC voltage is applied to the organic EL device thus obtained, the anode may be applied with a positive polarity and the cathode with a negative polarity. When a voltage of about 2 to 40 V is applied, a transparent or translucent electrode is applied. Luminescence can be observed from the side (anode or cathode and both). The organic EL element also emits light when an alternating voltage is applied.
  • the alternating current waveform to be applied may be arbitrary.
  • reaction solution was cooled to room temperature, washed with water to dissolve the salt, and a solid was collected by suction filtration.
  • reaction solution was cooled to room temperature, washed with water to dissolve the salt, and a solid was collected by suction filtration.
  • the structure of the compound was confirmed by NMR measurement.
  • reaction solution was cooled to room temperature, and water and toluene were added for liquid separation.
  • the obtained eluate was passed through an activated carbon short column to remove colored components. Crystals deposited while the filtrate was distilled off under reduced pressure were collected, and the compound 2-methyl-4- (6- (10-phenylanthracen-9-yl) represented by (1-11-1) was collected. ) Naphthalen-2-yl) pyridine (0.7 g) was obtained. The structure of the compound was confirmed by NMR measurement.
  • reaction solution was cooled to room temperature, and water and toluene were added for liquid separation.
  • the obtained eluate was passed through an activated carbon short column to remove colored components. Crystals precipitated while the filtrate was distilled off under reduced pressure were collected, recrystallized from toluene, and compound 3-methyl-4- (6- (10 -Phenylanthracen-9-yl) naphthalen-2-yl) pyridine (0.5 g) was obtained.
  • the structure of the compound was confirmed by NMR measurement.
  • reaction solution was cooled to room temperature, and water and toluene were added for liquid separation.
  • the solid obtained by evaporating the solvent under reduced pressure was recrystallized from toluene, and the compound 2-methyl-5- (6- (10-phenylanthracen-9-yl) naphthalene represented by (1-11-3) -2-yl) pyridine (1.2 g) was obtained.
  • the structure of the compound was confirmed by NMR measurement.
  • reaction solution was cooled to room temperature, and water and toluene were added for liquid separation.
  • reaction solution was cooled to room temperature, and water and toluene were added for liquid separation.
  • the obtained eluate was passed through an activated carbon short column to remove colored components.
  • the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized from toluene to give the compound 4-methyl-3- (6- (10-phenylanthracen-9-yl) naphthalene represented by (1-1-11-5) -2-yl) pyridine (0.6 g) was obtained.
  • reaction solution was cooled to room temperature, and water and toluene were added for liquid separation.
  • reaction solution was cooled to room temperature, and the precipitated solid was collected by suction filtration.
  • the obtained solid was purified by silica gel column chromatography (developing solution: toluene). Subsequently, the obtained eluate was passed through an activated carbon short column to remove colored components. The solvent was distilled off under reduced pressure, ethyl acetate was added for reprecipitation, and the compound represented by (1-1-11-8) 5-methyl-2- (6- (10-phenylanthracen-9-yl) naphthalene-2- Yl) pyridine (1.5 g) was obtained. The structure of the compound was confirmed by NMR measurement.
  • Table 1 below shows the material configuration of each layer in the devices according to Examples 1 to 4 and Comparative Examples 1 and 2 that were manufactured.
  • HI is N 4 , N 4 ′ -diphenyl-N 4 , N 4 ′ -bis (9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl] -4, 4′-diamine
  • NPD means N 4 , N 4 ′ -di (naphthalen-1-yl) -N 4 , N 4 ′ -diphenyl- [1,1′-biphenyl] -4,4′-diamine
  • Compound (A) is 9-phenyl-10- (4-phenylnaphthalen-1-yl) anthracene
  • compound (B) is N 5 , N 5 , N 9 , N 9 -7,7-hexaphenyl-7H-benzo [C] Fluorene-5,9-diamine
  • Compound (C) is 9,10-di ([2,2′-bipyridin] -5-yl) anthracene
  • a glass substrate of 26 mm ⁇ 28 mm ⁇ 0.7 mm obtained by polishing ITO deposited to a thickness of 180 nm by sputtering to 150 nm was used as a transparent support substrate.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing HI, a molybdenum vapor deposition boat containing NPD, and a compound (A) Molybdenum vapor deposition boat, molybdenum vapor deposition boat containing compound (B), molybdenum vapor deposition boat containing compound (1-7-74), molybdenum vapor deposition boat containing Liq, magnesium A molybdenum boat and a tungsten evaporation boat containing silver were installed.
  • a commercially available vapor deposition apparatus manufactured by Showa Vacuum Co., Ltd.
  • the following layers were sequentially formed on the ITO film of the transparent support substrate.
  • the vacuum chamber was depressurized to 5 ⁇ 10 ⁇ 4 Pa, first, a vapor deposition boat containing HI was heated and vapor-deposited to a film thickness of 40 nm to form a hole injection layer, and then NPD was contained. The vapor deposition boat was heated and vapor-deposited so that it might become a film thickness of 30 nm, and the positive hole transport layer was formed. Next, the vapor deposition boat containing the compound (A) and the vapor deposition boat containing the compound (B) were heated at the same time to form a light emitting layer by vapor deposition to a film thickness of 35 nm.
  • the deposition rate was adjusted so that the weight ratio of compound (A) to compound (B) was approximately 95 to 5.
  • the evaporation boat containing the compound (1-7-74) was heated and evaporated to a film thickness of 15 nm to form an electron transport layer.
  • the deposition rate of each layer was 0.01 to 1 nm / second.
  • the evaporation boat containing Liq was heated to deposit at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm.
  • a boat containing magnesium and a boat containing silver were heated at the same time and evaporated to a film thickness of 100 nm to form a cathode.
  • the deposition rate was adjusted so that the atomic ratio of magnesium and silver was 10: 1, and the cathode was formed so that the deposition rate was 0.1 to 10 nm / second, to obtain an organic electroluminescent device.
  • An organic EL device was obtained by the method according to Example 2 except that the compound (1-7-74) was replaced with the compound (1-7-26).
  • a constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 .
  • the driving test start voltage was 6.36 V, and the time for maintaining the luminance of 90% or more of the initial value was 151 hours.
  • Example 1 An organic EL device was obtained by the method according to Example 1 except that the compound (1-7-96) was changed to the compound (C). A constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . As a result, the drive test start voltage was 5.06 V, and the time for maintaining the luminance of 90% or more of the initial value was 6 hours.
  • Example 2 An organic EL device was obtained in the same manner as in Example 1 except that the compound (1-7-96) was changed to the compound (D). A constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . As a result, the drive test start voltage was 5.05 V, and the time for maintaining the luminance of 90% or more of the initial value was 10 hours.
  • Table 3 below shows the material structure of each layer in the devices according to Examples 5 to 20 and Comparative Examples 3 to 5.
  • HT represents N-([1,1′-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl)- 9H-fluoren-2-amine
  • compound (E) is 9- (4- (naphthalen-1-yl) phenyl) -10-phenylanthracene
  • compound (F) is 4,4 ′-((7,7-diphenyl) -7H-benzo [c] fluorene-5,9-diyl) bis ((phenyl) amino)) dibenzonitrile
  • compound (G) is 4 ′-(4- (10- (naphthalen-2-yl) anthracene-9 -Yl) phenyl) -2,2 ': 6', 2 "-terpyridine
  • compound (H) is 3- (6- (10-phenylanthracen-9-yl) naphthalen-2-yl)
  • This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), a molybdenum vapor deposition boat containing HI, a molybdenum vapor deposition boat containing HT, and a compound (E) Molybdenum vapor deposition boat, molybdenum vapor deposition boat containing compound (F), molybdenum vapor deposition boat containing compound (1-11-1), molybdenum vapor deposition boat containing Liq, magnesium A molybdenum boat and a tungsten evaporation boat containing silver were installed.
  • a commercially available vapor deposition apparatus manufactured by Showa Vacuum Co., Ltd.
  • the following layers were sequentially formed on the ITO film of the transparent support substrate.
  • the vacuum chamber was depressurized to 5 ⁇ 10 ⁇ 4 Pa, and first, a vapor deposition boat containing HI was heated to deposit to a film thickness of 40 nm to form a hole injection layer, and then HT entered.
  • the vapor deposition boat was heated and vapor-deposited so that it might become a film thickness of 30 nm, and the positive hole transport layer was formed.
  • the vapor deposition boat containing the compound (E) and the vapor deposition boat containing the compound (F) were heated at the same time to form a light emitting layer by vapor deposition to a film thickness of 35 nm.
  • the deposition rate was adjusted so that the weight ratio of compound (E) to compound (F) was approximately 95 to 5.
  • the vapor deposition boat containing the compound (1-11-1) and the vapor deposition boat containing Liq were heated at the same time so as to have a film thickness of 25 nm, thereby forming an electron transport layer.
  • the deposition rate was adjusted so that the weight ratio of the compound (1-11-1) and Liq was about 1: 1.
  • the deposition rate of each layer was 0.01 to 1 nm / second.
  • the evaporation boat containing Liq was heated to deposit at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm.
  • a boat containing magnesium and a boat containing silver were heated at the same time and evaporated to a film thickness of 100 nm to form a cathode.
  • the deposition rate was adjusted so that the atomic ratio of magnesium and silver was 10: 1, and the cathode was formed so that the deposition rate was 0.1 to 10 nm / second, to obtain an organic electroluminescent device.
  • An organic EL device was obtained by the method according to Example 5 except that the compound (1-11-1) was changed to the compound (1-11-2).
  • a constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 .
  • the driving test starting voltage was 4.12 V, and the time for maintaining the luminance of 90% or more of the initial value was 85 hours.
  • An organic EL device was obtained by the method according to Example 5 except that the compound (1-11-1) was changed to the compound (1-11-3).
  • a constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 .
  • the drive test start voltage was 3.78 V, and the time for maintaining the luminance of 90% or more of the initial value was 97 hours.
  • An organic EL device was obtained by the method according to Example 5 except that the compound (1-11-1) was changed to the compound (1-11-4).
  • a constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 .
  • the driving test starting voltage was 3.95 V, and the time for maintaining the luminance of 90% or more of the initial value was 83 hours.
  • An organic EL device was obtained by the method according to Example 5 except that the compound (1-11-1) was changed to the compound (1-14-2).
  • a constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 .
  • the driving test start voltage was 3.61 V, and the time for maintaining the luminance of 90% or more of the initial value was 76 hours.
  • An organic EL device was obtained by the method according to Example 5 except that the compound (1-11-1) was changed to the compound (1-14-3).
  • a constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 .
  • the driving test start voltage was 3.85 V, and the time for maintaining the luminance of 90% or more of the initial value was 141 hours.
  • An organic EL device was obtained by the method according to Example 5 except that the compound (1-11-1) was replaced with the compound (1-1-14-16).
  • a constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 .
  • the driving test start voltage was 4.25 V, and the time for maintaining the luminance of 90% or more of the initial value was 70 hours.
  • Example 3 An organic EL device was obtained in the same manner as in Example 5 except that the compound (1-11-1) was changed to the compound (G). A constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . As a result, the drive test start voltage was 5.36 V, and the time for maintaining the luminance of 90% or more of the initial value was 2 hours.
  • Example 4 An organic EL device was obtained in the same manner as in Example 5 except that the compound (1-11-1) was changed to the compound (H). A constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . As a result, the driving test start voltage was 4.12 V, and the time for maintaining the luminance of 90% or more of the initial value was 26 hours.
  • Example 5 An organic EL device was obtained by the method according to Example 5 except that the compound (1-11-1) was changed to the compound (I).
  • a constant current driving test was carried out using an ITO electrode as an anode and a magnesium / silver electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 .
  • the driving test start voltage was 4.15 V
  • the time for maintaining the luminance of 90% or more of the initial value was 30 hours.
  • an organic electroluminescent element that improves the lifetime of the light emitting element and has an excellent balance with the driving voltage, a display device including the organic electroluminescent element, and a lighting device including the organic electroluminescent element. it can.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Le composé selon l'invention répondant à la formule (1) peut être utilisé comme matériau de transport des électrons pour éléments électroluminescents organiques, l'utilisation dudit matériau de transport des électrons contribuant à augmenter la durée de vie, etc. des éléments électroluminescents organiques. Dans la formule (1), les (Py) sont indépendants et sont des groupements représentés par les formules (2), (3) ou (4);m et n sont égaux à 0 ou à 1 et m + n = 1; et au moins l'un des atomes d'hydrogène du cycle benzénique, du cycle naphténique ou du cycle pyridine de la formule (1) est substitué par un groupement alkyle en C1-6 ou un groupement cycloalkyle en C3-6.
PCT/JP2011/075179 2010-11-04 2011-11-01 Matériau de transport des électrons et élément électroluminescent organique l'employant WO2012060374A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020137011642A KR101835020B1 (ko) 2010-11-04 2011-11-01 전자 수송 재료 및 이것을 사용한 유기 전계 발광 소자
JP2012541874A JP5737294B2 (ja) 2010-11-04 2011-11-01 電子輸送材料およびこれを用いた有機電界発光素子
CN201180052069.3A CN103189355B (zh) 2010-11-04 2011-11-01 电子传输材料及使用其的有机电激发光元件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010-247332 2010-11-04
JP2010247332 2010-11-04

Publications (1)

Publication Number Publication Date
WO2012060374A1 true WO2012060374A1 (fr) 2012-05-10

Family

ID=46024488

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2011/075179 WO2012060374A1 (fr) 2010-11-04 2011-11-01 Matériau de transport des électrons et élément électroluminescent organique l'employant

Country Status (5)

Country Link
JP (1) JP5737294B2 (fr)
KR (1) KR101835020B1 (fr)
CN (2) CN104744349B (fr)
TW (1) TWI508949B (fr)
WO (1) WO2012060374A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012126717A (ja) * 2010-11-25 2012-07-05 Jnc Corp 電子輸送材料およびこれを用いた有機電界発光素子
WO2013114941A1 (fr) * 2012-02-03 2013-08-08 Jnc株式会社 Dérivé d'anthracène et élément électroluminescent organique l'utilisant
JP2013177375A (ja) * 2012-02-06 2013-09-09 Jnc Corp 電子輸送材料およびこれを用いた有機電界発光素子
KR20140090035A (ko) * 2013-01-08 2014-07-16 에스에프씨 주식회사 헤테로아릴 치환기를 갖는 나프틸기를 포함하는 안트라센 유도체 및 이를 포함하는 유기 발광 소자
KR20140090036A (ko) * 2013-01-08 2014-07-16 에스에프씨 주식회사 헤테로아릴 치환기를 갖는 페닐기를 포함하는 안트라센 유도체 및 이를 포함하는 유기 발광 소자
WO2014204234A1 (fr) * 2013-06-19 2014-12-24 경상대학교산학협력단 Dérivé de phénylanthracène et dispositif électroluminescent organique le contenant
KR101492523B1 (ko) * 2013-01-25 2015-02-12 에스에프씨 주식회사 발광층과 전자수송층에 각각 아릴 치환된 안트라센 유도체를 포함하는 유기 발광 소자
JP2015051966A (ja) * 2013-08-07 2015-03-19 Jnc株式会社 電子輸送材料およびこれを用いた有機電界発光素子
WO2015064560A1 (fr) * 2013-10-29 2015-05-07 Jnc株式会社 Composé d'anthracène ; matériau électroluminescent ; et élément électroluminescent organique, dispositif d'affichage, et dispositif d'éclairage l'utilisant

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180108604A (ko) * 2016-02-10 2018-10-04 가꼬우 호징 관세이 가쿠잉 지연 형광 유기 전계 발광 소자
KR20240095561A (ko) * 2022-12-06 2024-06-26 삼성디스플레이 주식회사 혼합 조성물을 포함한 전자 수송층, 이를 포함한 발광 소자 제조 방법, 발광 소자 및 전자 장치

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004002297A (ja) * 2002-04-11 2004-01-08 Idemitsu Kosan Co Ltd 新規含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子
JP2009256352A (ja) * 2008-04-15 2009-11-05 Samsung Mobile Display Co Ltd ビピリジン系化合物及びそれを含む有機膜を備えた有機発光素子
WO2009139579A2 (fr) * 2008-05-14 2009-11-19 주식회사 두산 Préparation de dérivés d'anthracène asymétriques et dispositif électroluminescent organique utilisant lesdits dérivés
WO2010137678A1 (fr) * 2009-05-29 2010-12-02 チッソ株式会社 Matériau de transport d'électrons et dispositif électroluminescent organique employant ledit matériau

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1751024A (zh) * 2003-01-10 2006-03-22 出光兴产株式会社 含氮杂环衍生物以及使用该衍生物的有机电致发光元件
JP4788202B2 (ja) * 2004-07-09 2011-10-05 Ｊｎｃ株式会社 発光材料およびこれを用いた有機電界発光素子
KR100878115B1 (ko) * 2005-10-21 2009-01-14 주식회사 엘지화학 신규한 바이나프탈렌 유도체, 이의 제조방법 및 이를이용한 유기전자소자
US8367220B2 (en) * 2007-10-30 2013-02-05 Samsung Electronics Co., Ltd. Anthracene-based compound and organic light emitting device employing the same
JP5353233B2 (ja) * 2007-12-27 2013-11-27 Ｊｎｃ株式会社 ピリジルフェニル基を有するアントラセン誘導体化合物及び有機電界発光素子
CN101570536B (zh) * 2008-04-28 2014-08-20 三星显示有限公司 基于蒽的化合物和使用其的有机发光器件
KR101507166B1 (ko) * 2008-12-08 2015-04-30 엘지디스플레이 주식회사 청색 발광 화합물 및 이를 포함하는 유기전계발광소자
WO2010074087A1 (fr) * 2008-12-26 2010-07-01 出光興産株式会社 Matériau pour élément électroluminescent organique, et élément électroluminescent organique
JP5210187B2 (ja) * 2009-01-22 2013-06-12 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子
CN101597259B (zh) * 2009-07-07 2012-11-07 清华大学 有机材料及其在有机电致发光器件中的应用
JP5807637B2 (ja) * 2010-07-05 2015-11-10 Jnc株式会社 電子輸送材料およびこれを用いた有機電界発光素子
JP5799637B2 (ja) * 2010-08-26 2015-10-28 Jnc株式会社 アントラセン誘導体およびこれを用いた有機電界発光素子

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004002297A (ja) * 2002-04-11 2004-01-08 Idemitsu Kosan Co Ltd 新規含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子
JP2009256352A (ja) * 2008-04-15 2009-11-05 Samsung Mobile Display Co Ltd ビピリジン系化合物及びそれを含む有機膜を備えた有機発光素子
WO2009139579A2 (fr) * 2008-05-14 2009-11-19 주식회사 두산 Préparation de dérivés d'anthracène asymétriques et dispositif électroluminescent organique utilisant lesdits dérivés
WO2010137678A1 (fr) * 2009-05-29 2010-12-02 チッソ株式会社 Matériau de transport d'électrons et dispositif électroluminescent organique employant ledit matériau

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012126717A (ja) * 2010-11-25 2012-07-05 Jnc Corp 電子輸送材料およびこれを用いた有機電界発光素子
US9478750B2 (en) 2012-02-03 2016-10-25 Jnc Corporation Anthracene derivative and organic electroluminescent element using the same
WO2013114941A1 (fr) * 2012-02-03 2013-08-08 Jnc株式会社 Dérivé d'anthracène et élément électroluminescent organique l'utilisant
JP2013177375A (ja) * 2012-02-06 2013-09-09 Jnc Corp 電子輸送材料およびこれを用いた有機電界発光素子
KR20140090035A (ko) * 2013-01-08 2014-07-16 에스에프씨 주식회사 헤테로아릴 치환기를 갖는 나프틸기를 포함하는 안트라센 유도체 및 이를 포함하는 유기 발광 소자
KR20140090036A (ko) * 2013-01-08 2014-07-16 에스에프씨 주식회사 헤테로아릴 치환기를 갖는 페닐기를 포함하는 안트라센 유도체 및 이를 포함하는 유기 발광 소자
KR102030584B1 (ko) * 2013-01-08 2019-10-10 에스에프씨주식회사 헤테로아릴 치환기를 갖는 페닐기를 포함하는 안트라센 유도체 및 이를 포함하는 유기 발광 소자
KR102051952B1 (ko) * 2013-01-08 2019-12-04 에스에프씨주식회사 헤테로아릴 치환기를 갖는 나프틸기를 포함하는 안트라센 유도체 및 이를 포함하는 유기 발광 소자
KR101492523B1 (ko) * 2013-01-25 2015-02-12 에스에프씨 주식회사 발광층과 전자수송층에 각각 아릴 치환된 안트라센 유도체를 포함하는 유기 발광 소자
WO2014204234A1 (fr) * 2013-06-19 2014-12-24 경상대학교산학협력단 Dérivé de phénylanthracène et dispositif électroluminescent organique le contenant
KR101751784B1 (ko) * 2013-06-19 2017-06-29 경상대학교산학협력단 페닐안트라센 유도체 및 이를 포함하는 유기 발광소자
JP2015051966A (ja) * 2013-08-07 2015-03-19 Jnc株式会社 電子輸送材料およびこれを用いた有機電界発光素子
WO2015064560A1 (fr) * 2013-10-29 2015-05-07 Jnc株式会社 Composé d'anthracène ; matériau électroluminescent ; et élément électroluminescent organique, dispositif d'affichage, et dispositif d'éclairage l'utilisant

Also Published As

Publication number Publication date
CN104744349B (zh) 2017-09-22
JP5737294B2 (ja) 2015-06-17
CN103189355A (zh) 2013-07-03
TW201226394A (en) 2012-07-01
KR101835020B1 (ko) 2018-03-06
TWI508949B (zh) 2015-11-21
CN103189355B (zh) 2015-08-26
KR20130140709A (ko) 2013-12-24
CN104744349A (zh) 2015-07-01
JPWO2012060374A1 (ja) 2014-05-12

Similar Documents

Publication Publication Date Title
JP5533863B2 (ja) 電子輸送材料およびこれを用いた有機電界発光素子
JP5737294B2 (ja) 電子輸送材料およびこれを用いた有機電界発光素子
KR101418840B1 (ko) 전자 수송 재료 및 이것을 이용한 유기 전계발광 소자
JP5353233B2 (ja) ピリジルフェニル基を有するアントラセン誘導体化合物及び有機電界発光素子
JP5807637B2 (ja) 電子輸送材料およびこれを用いた有機電界発光素子
JP5262192B2 (ja) 電子輸送材料およびこれを用いた有機電界発光素子
JP5907069B2 (ja) 電子輸送材料およびこれを用いた有機電界発光素子
WO2011105373A1 (fr) Composé pyridyle substitué et élément électroluminescent organique
JP5799772B2 (ja) 電子輸送材料およびこれを用いた有機電界発光素子
JP5176366B2 (ja) 新規ビピリジン誘導体、およびこれを含む有機電界発光素子
JP2015071619A (ja) ベンゾピリドインドール誘導体および有機エレクトロルミネッセンス素子
JP6402904B2 (ja) 電子輸送材料およびこれを用いた有機電界発光素子
TWI607997B (zh) 新穎之萘并三唑衍生物及有機電致發光元件
JP6428762B2 (ja) 電子輸送材料およびこれを用いた有機電界発光素子
JP2013227251A (ja) 電子輸送材料およびこれを用いた有機電界発光素子
JP6136311B2 (ja) 電子輸送材料およびこれを用いた有機電界発光素子
JP6479770B2 (ja) キノリノトリアゾール誘導体および有機エレクトロルミネッセンス素子
JP6070047B2 (ja) 電子輸送材料およびこれを用いた有機電界発光素子
JP5549270B2 (ja) アントラセン誘導体およびこれを用いた有機電界発光素子
JP2016074623A (ja) アルキル置換アゾールを有する化合物、この化合物を含む電子輸送材料およびこれを用いた有機電界発光素子

Legal Events

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

Ref document number: 11838024

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2012541874

Country of ref document: JP

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 20137011642

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11838024

Country of ref document: EP

Kind code of ref document: A1