WO2009061145A1 - Nouveau composé et dispositif électroluminescent organique contenant ce composé - Google Patents

Nouveau composé et dispositif électroluminescent organique contenant ce composé Download PDF

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WO2009061145A1
WO2009061145A1 PCT/KR2008/006564 KR2008006564W WO2009061145A1 WO 2009061145 A1 WO2009061145 A1 WO 2009061145A1 KR 2008006564 W KR2008006564 W KR 2008006564W WO 2009061145 A1 WO2009061145 A1 WO 2009061145A1
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group
substituted
unsubstituted
compound
halogen
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PCT/KR2008/006564
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English (en)
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Jae-Chol Lee
Kong-Kyeom Kim
Sung-Kil Hong
Tae-Yoon Park
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Lg Chem, Ltd.
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Priority claimed from KR1020080073238A external-priority patent/KR20090048299A/ko
Application filed by Lg Chem, Ltd. filed Critical Lg Chem, Ltd.
Priority to US12/742,069 priority Critical patent/US8395143B2/en
Priority to EP08847615.5A priority patent/EP2215183B1/fr
Priority to CN200880119858.2A priority patent/CN101896574B/zh
Priority to JP2010533010A priority patent/JP5562862B2/ja
Publication of WO2009061145A1 publication Critical patent/WO2009061145A1/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
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
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    • 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
    • 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
    • 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
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/731—Liquid crystalline materials

Definitions

  • the present invention relates to an organic light emitting device in which a novel compound that is capable of largely improving a life span, efficiency, electrochemical stability and thermal stability of the organic light emitting device is included in an organic compound layer.
  • An organic light emission phenomenon is an example of a conversion of current into visible rays through an internal process of a specific organic molecule.
  • the organic light emission phenomenon is based on the fol lowing mechanism.
  • An organic light emitting device which is based on the above mechanism typiccollectivelyy comprises a cathode, an anode, and organic material layer(s), for example, organic material layers including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, interposed therebetween.
  • the materials used in the organic light emitting device are mostly pure organic materials or complexes of organic material and metal.
  • the material used in the organic light emitting device may be classified as a hole injection material, a hole transport material, a light emitting material, an electron transport material, or an electron injection material, according to its use.
  • an organic material having a p-type property which is easily oxidized and is electrochemiccollectivelyy stable when it is oxidized, is mostly used as the hole injection material or the hole transport material.
  • an organic material having an n-type property which is easily reduced and is electrochemiccollectivelyy stable when it is reduced, is used as the electron injection material or the electron transport material.
  • the light emitting layer material an organic material having both p-type and n-type properties is preferable, which is stable when it is oxidized and when it is reduced. Also a material having high light emission efficiency for conversion of the exciton into light when the exciton is formed is preferable. In addition, it is preferable that the material used in the organic light emitting device further have the following properties.
  • the material used in the organic light emitting device have excellent thermal stability.
  • the reason is that joule heat is generated by movement of electric charges in the organic light emitting device.
  • NPB which has recently been used as the hole transport layer material, has a glass transition temperature of 100 ° C or lower, thus it is difficult to apply to an organic light emitting device requiring a high current.
  • a LUMO energy level of PEDOT:PSS which is currently used as a hole transport material of an organic light emitting device produced using a solution coating method, is lower than that of an organic material used as a light emitting layer material, thus it is difficult to produce an organic light emitting device having high efficiency and a long lifespan.
  • the material used in the organic light emitting device must have excellent chemical stability, electric charge mobility, and interfacial characteristic with an electrode or an adjacent layer. That is to say, the material used in the organic light emitting device must be little deformed by moisture or oxygen. Furthermore, proper hole or electron mobility must be assured so as to balance densities of the holes and of the electrons in the light emitting layer of the organic light emitting device to maximize the formation of excitons. Additionally, it has to be able to have a good interface with an electrode including metal or metal oxides so as to assure stability of the device.
  • the present inventors aim to provide an organic light emitting device that includes aheterocompound derivative which is capable of satisfying conditions required of a material which may be used for an organic light emitting device, for example, a proper energy level, electrochemical stability, and thermal stability, and which has a chemical structure capable of playing various roles required for the organic light emitting device, depending on a substituent group.
  • aheterocompound derivative which is capable of satisfying conditions required of a material which may be used for an organic light emitting device, for example, a proper energy level, electrochemical stability, and thermal stability, and which has a chemical structure capable of playing various roles required for the organic light emitting device, depending on a substituent group.
  • the present invention provides a compound of the following Formula 1.
  • the present invention provides an organic light emitting device which comprises a first electrode, organic material layer(s) having one or more layers and comprising a light emitting layer, and a second electrode, wherein the first electrode, the organic material layer(s), and the second electrode form a layered structure and at least one layer of the organic material layer(s) includes a compound of the following Formula 1 or a compound of Formula 1 into which a thermosetting or photo-crosslinkable functional group is introduced:
  • X is selected from the group consisting of hydrogen; an alkyl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitri Ie group and an acetylene group; an alkoxy group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted
  • an aryl group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group; an hetero ring group including 0, N or S as a heteroatom, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstit
  • a f luorenyl group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted f luorenyl group, a nitrile group and an acetylene group; -N(R 1 XR"); a nitri Ie group! anitro group; a halogen group; -CO-N(R 1 ) (R"); and -COO-R 1 ,
  • R' and R" are each independently selelcted from the group consisting of hydrogen, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group,
  • L is an arylene group having 6 to 40 carbon atoms, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of nitro, nitrile, halogen, an alkyl group, an alkoxy group and an amino group; a divalent hetero ring group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of nitro, nitrile, halogen, an alkyl group, an alkoxy group and an amino group; or a fluorenylene group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of nitro, nitrile, halogen, an alkyl group, an alkoxy group and an amino group,
  • Ri and R 2 are each independently selected from the group consisting of hydrogen; deuterium; an alkyl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubst ituted arylalkyl group, a subst ituted or unsubst ituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group; an alkoxy group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl
  • an hetero ring group including 0, N or S as a heteroatom which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group!
  • substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted
  • a carbazolyl group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group!
  • substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group,
  • a f luorenyl group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl alkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted f luorenyl group, a nitrile group and an acetylene group; an aryloxy group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsub
  • R 1 and R 2 may form an aliphatic or hetero condensation ring in conjunction with adjacent groups, and at least one of R 3 to Rg is selected from the group consisting of deuterium; an alkenyl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted
  • an hetero ring group including 0, N or S as a heteroatom which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group!
  • substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted
  • a carbazolyl group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group!
  • substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group,
  • a fluorenyl group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubsti tuted aryl group, a substituted or unsubst ituted aryl alkyl group, a substituted or unsubst ituted arylalkenyl group, a substituted or unsubst ituted hetero ring group, a substituted or unsubst ituted carbazolyl group, a substituted or unsubst ituted fluorenyl group, a nitri Ie group and an acetylene group!
  • substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubsti tuted aryl group, a substituted or unsubst ituted
  • R3 to Rg may form an aliphatic or hetero condensation ring in conjunction with adjacent groups, and the remains of R3 to Rg are selected from hydrogen or deuterium.
  • a compound according to the present invention is configured so that stability in respects to a hole and an electron is increased while properties of carbazole are not largely changed by introducing deuterium to carbazole.
  • These compounds may be used as an organic material layer material, particularly, a hole injection material and/or a hole transport material in an organic light emitting device, and in the case of when it is used in the organic light emitting device, a driving voltage of the device may be reduced, light efficiency may be improved, and a life span property of the device may be improved.
  • FIG. 1 illustrates an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4
  • FIG. 2 illustrates an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4.
  • X of Formula 1 is selected from the group consisting of hydrogen; an alkyl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl alkyl group, a substituted or unsubstituted aryl alkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group!
  • an alkoxy group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubst ituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubst ituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted f luorenyl group, a nitrile group and an acetylene group; an alkenyl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted with
  • an hetero ring group including 0, N or S as a heteroatom which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl alkyl group, a substituted or unsubstituted aryl alkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group; a carbazolyl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alken
  • X of Formula 1 when it is an aryl group, it may be selected from a monocyclic aromatic ring, such as a phenyl group, a biphenyl group, a terphenyl group, and a stilbene, and a multicyclic aromatic ring, such as a naphthyl group, an anthracenyl group, a phenanthrene group, a pyrenyl group, and a perylenyl group, and in the case of when X is a hetero ring group, it may be selected from the group consisting of a thiophenyl group, a furan group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, atriazolyl group, apyridyl group, a pyradazine group, aquinolinyl group, an isoquinoline group,
  • L of Formula 1 is an arylene group having 6 to 40 carbon atoms, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of nitro, nitrile, halogen, an alkyl group, an alkoxy group and an amino group!
  • a divalent hetero ring group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of nitro, nitrile, halogen, an alkyl group, an alkoxy group and an amino group; or a fluorenylene group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of nitro, nitrile, halogen, an alkyl group, an alkoxy group and an amino group.
  • L is a phenylene group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of nitro, nitrile, halogen, an alkyl group, an alkoxy group and an amino group; a divalent hetero ring group including 0, N or S, and having 5 or 6 carbon atoms, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of nitro, nitrile, halogen, an alkyl group, an alkoxy group and an amino group; or a fluorenylene group, which is substituted or unsubst ituted with one or more substituent groups selected from the group consisting of nitro, nitrile, halogen, an alkyl group, an alkoxy group and an amino group, and it is most preferable that it is a phenylene group or a fluorenylene group.
  • Ri and R2 of Formula 1 are each independent Iy selected from the group consisting of hydrogen; deuterium; an alkyl group, which is substituted or unsubst ituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubst ituted aryl group, a substituted or unsubst ituted aryl alkyl group, a substituted or unsubst ituted arylalkenyl group, a substituted or unsubst ituted hetero ring group, a substituted or unsubst ituted carbazolyl group, a substituted or unsubst ituted fluorenyl group, a nitrile group and an acetylene group; an alkoxy group, which is substituted or unsubst ituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl
  • an alkenyl group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl alkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group; an aryl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a
  • an hetero ring group including 0, N or S as a heteroatom which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl alky1 group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group; a carbazolyl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an al
  • an arylthio group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group; an alkoxycarbonyl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl
  • Ri and R2 may form an aliphatic or hetero condensation ring in conjunction with adjacent groups, and it is preferable that at least one of R3 to R9 is selected from the group consisting of deuterium; an alkenyl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl alkyl group, a substituted or unsubstituted aryl alkenyl group,
  • an hetero ring group including 0, N or S as a heteroatom which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group!
  • substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstitute
  • a carbazolyl group which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group; a fluorenyl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl
  • Ri and R 2 are each independently an aryl group, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl alkyl group, a substituted or unsubstituted aryl alkenyl group, a substituted or unsubstituted hetero ring group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a nitrile group and an acetylene group; or an hetero ring group including 0, N or S as aheteroatom, which is substituted or unsubstituted with one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alken
  • Ri and R2 are each independently any one of the following groups, but is not limited thereto.
  • the number of carbon atoms of the alkyl group, the alkoxy group, and the alkenyl group is not particularly 1 imited, but it is preferable that it is in the range of 1 to 20.
  • the length of the alkyl group that is included in the compound does not affect the conjugation length of the compound, but may auxiliarily affect an application method of the compound to the organic light emitting device, for example, the application of a vacuum deposition method or a solution coating method.
  • Illustrative, but non-limiting, examples of the aryl group of Ri to Rg of Formula 1 include monocyclic aromatic rings, such as a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group, and mult icyclic aromatic rings, such as a naphthyl group, an anthracenyl group, a phenanthrene group, a pyrenyl group, and a perylenyl group.
  • hetero ring group of Ri to Rg of Formula 1 examples include a thiophenyl group, a furan group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, atriazolyl group, apyridyl group, a pyradazine group, a quinolinyl group, an isoquinoline group, and an acridyl group.
  • the compound of Formula 1 may be a compound that is represented by the following Formulas.
  • the compound of Formula 1 may have a property that is required when it is used as an organic material layer used in an organic light emitting device by using a structure in which carbazole is substituted with arylene and the like as a core structure and introducing various subst ituents, particularly, deuterium.
  • the conjugation length of the compound has a close relationship with an energy band gap.
  • the energy band gap is reduced as the conjugation length of the compound increases.
  • the core structure since a conjugation structure is limited in the core structure of the compound of Formula 1, the core structure has a large energy band gap.
  • various subst ituent groups are introduced to Ri to Rg and X positions of the core structure having the large energy band gap so as to produce compounds having various energy band gaps.
  • substituent groups which are frequently applied to hole injection layer material, hole transport layer material, light emitting layer material, and electron transport layer materials during the production of the organic light emitting device, are introduced into the core structure so as to produce substances capable of sat isfying the requirements of each organic material layer.
  • the core structure of the compound of Formula 1 includes the amine structure, it has an energy level suitable for the hole injection and/or hole transport materials in the organic light emitting device.
  • the compound having the proper energy level is selected depending on the substituent group among the compounds represented by Formula 1 to be used in the organic light emitting device, thereby it is possible to realize a device having a low driving voltage and a high light efficiency.
  • substituent groups in particular , hydrogen or deuterium, are introduced into the core structure so as to precisely control the energy band gap, and to improve interfacial characteristics with organic materials, thereby apply the compound to various fields.
  • the compound of Formula 1 since the compound of Formula 1 has a high glass transition temperature (Tg), it has excellent thermal stability. Such increase in thermal stability is an important factor providing driving stability to the device.
  • the compound of Formula 1 may be used to form the organic material layer using a vacuum deposition process or a solution coating process during the production of the organic light emitting device.
  • a solution coating process include a spin coating process, a dip coating process, an inkjet printing process, a screen printing process, a spray process, and a roll coating process.
  • the organic light emitting device of the present invention may be produced using known materials through a known process, modified only in that at least one layer of organic material layer(s) include the compound of the present invention, that is, the compound of Formula 1.
  • the organic material layer(s) of the organic light emitting device according to the present invention may have a single layer structure, or alternatively, a mult i layered structure in which at least two organic material layers are layered.
  • the organic light emitting device of the present invention may comprise a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer as the organic material layer(s) .
  • the structure of the organic light emitting device is not limited to this, but may comprise a smaller number of organic material layers.
  • the organic light emitting device of the present invention may be produced, for example, by sequentially layering a first electrode, organic material layer(s), and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as a sputtering method or an e-beam evaporation method, may be used, but the method is not limited to these.
  • N-bromosuccinimide (39.5 g, 222 mmol) was added thereto, and they
  • Example l-4> Manufacturing of the compound 2
  • the compound C (4 g, 11.3 mmol) that was manufactured in Example 1-3 and bis(4-biphenylyl)amine (4.18 g, 13 mmol) were dissolved in xylene (100 ml), sodium-tertiary-butoxide (1.4 g, 14.7 mmol) and bisCtri tertsammlungy-butyl phosphine)pal ladium (0.11 g, 0.23 mmol ) were added thereto, and they were refluxed for 5 hours under a nitrogen atmosphere. After the reaction was finished, it was cooled to normal temperature, an acidic white clay was put, and then agitated.
  • the compound A (15 g, 93.6 mmol) that was manufactured in Example 3-1 was dissolved in anhydrous tetrahydrofuran (300 ml), n-butyl lithium (2.5M hexane solution, 41.2 ml, 103 mmol) was added dropwise at -78 0 C, and after 1 hour, trimethyl borate (11. 4 g, 110 mmol) was put thereinto. After 1 hour, IN hydrogen chloride aqueous solution was put thereinto, and it was heated to normal temperature. After the organic layer was separated, it was dried by using anhydrous magnesium sulfate, and distilled under the reduced pressure. It was recrystallized by using ethyl ether and hexane to obtain a compound B (13 g, yield 68%) .
  • Example 3-6 Manufacturing of the compound F
  • the compound E (11 g, 19.7 mmol) that was manufactured in Example 3-5 was dissolved in anhydrous tetrahydrofuran (200 ml), n-butyl lithium (2.5Mhexane solution, 7.9 ml, 19.7 mmol) was added dropwise at -78 0 C, and after 1 hour, heavy water (0.6 g, 30 mmol) was put thereinto. After it was heated to normal temperature, water (50 ml) was put thereinto, it was agitated, and the organic layer was separated. The organic layer was dried by using anhydrous magnesium sulfate, filtered, and distilled under the reduced pressure.
  • Example 3-8 Manufacturing of the Formula 4
  • the compound G(3.5 g, 6.8 mmol) that was manufactured in Example 3-7 and N-phenyl-1-naphthyl amine (1.6 g, 7.3 mmol) were dissolved in xylene (80 ml), sodium-tertiary-butoxide (0.85 g, 8.8 mmol) and bis(tri tertiary-butyl phosphine)palladium (0.04 g, 0.08 mmol) were added thereto, and they were refluxed for 5 hours under a nitrogen atmosphere. After the reaction was finished, it was cooled to normal temperature, and an acidic white clay was put thereinto, and they were agitated.
  • Example 5-4 Manufacturing of the compound D
  • the compound C (6 g, 12.6 mmol) that was manufactured in Example 5-3 was dissolved in anhydrous tetrahydrofuran (100 ml), n-butyl lithium (2.5M hexane solution, 12.1 ml, 30.2 mmol) was added dropwise at -78°C, and after 1 hour, heavy water (1.1 g, 55 mmol) was put thereinto. After it was heated to normal temperature, water (30 ml) was put thereinto, it was agitated, and the organic layer was separated. The organic layer was dried by using anhydrous magnesium sulfate, filtered, and disti 1 led under the reduced pressure.
  • Example 6-l Manufacturing of the compound A
  • Example 6-2 Manufacturing of the Formula 17 The compound A (1.5 g, 3 mmol) that was manufactured in Example
  • Example 7-1 The compound A (6 g, 15 mmol) that was manufactured in Example 7-1 was dissolved in anhydrous tetrahydrofuran (100 ml), n-butyl lithium (2.5M hexane solution, 13.2 ml, 33 mmol) was added dropwise at -78°C, and after
  • Example 7-3 Manufacturing of the compound C
  • the compound B (2.5 g, 10.2 mmol) that was manufactured in Example 7-2 was dissolved in chloroform (60 mL) , N-bromosuccinimide (3.9 g, 22 mmol) was added thereto, and they were agitated for 5 hours at normal temperature. Distilled water was put into the reaction solution and the organic layer was extracted. It was disti 1 led under the reduced pressure, and recrystallized by using tetrahydrofuran and ethanol to obtain a compound C (3.7 g, yield 90%).
  • MS: [M+H] + 404
  • Example 7-4 and 4-chlorophenyl boronic acid (0.69 g, 4.4 mmol) were dissolved in tetrahydrofuran (70 ml), tetrakis(triphenylphosphine)palladium (0.09 g, 0.07 mmol) and 2N potassium carbonate aqueous solution were put thereinto and ref luxed for
  • Example 8-2 Manufacturing of the compound B
  • the compound A (6.5 g, 13.6 mmol) that was manufactured in Example 8-1 was dissolved in anhydrous tetrahydrofuran (100 ml), n-butyl lithium (2.5M hexane solution, 5.4 ml , 13.6 mmol) was added dropwise at -78°C, and after 1 hour, heavy water (0.5 g, 25 mmol) was put thereinto. After it was heated to normal temperature, water (20 ml) was put thereinto, it was agitated, and the organic layer was separated. The organic layer was dried by using anhydrous magnesium sulfate, filtered, and distilled under the reduced pressure.
  • Example 9-2 Manufacturing of the compound B
  • Example 9-4 Manufacturing of the compound D
  • the compound C (6 g, 14.7 mmol) that was manufactured in Example 9-3 was dissolved in anhydrous tetrahydrofuran (120 ml), n-butyl lithium (2.5M hexane solution, 12.9 ml, 32.3 mmol) was added dropwise at -78°C, and after 1 hour, heavy water (1.2 g, 60 mmol) was put thereinto. After it was heated to normal temperature, water (30 ml) was put thereinto, it was agitated, and the organic layer was separated. The organic layer was dried by using anhydrous magnesium sulfate, filtered, and distilled under the reduced pressure.
  • Example 9-5 Manufacturing of the compound E
  • the compound D (2 g, 8 mmol) that was manufactured in Example 9-4 was dissolved in chloroform (60 mL), N-bromosuccinimide (1.4 g, 8 mmol) was added thereto, and they were agitated for 5 hours at normal temperature. Distilled water was put into the reaction solution and the organic layer was extracted. It was distilled under the reduced pressure, and the next reaction was performed without the purification process.
  • a product manufactured by Fischer Inc. was used as the detergent , and dist i 1 led water was produced by fi lter ing twice using a filter manufactured by Mil lipore Inc.
  • ultrasonic washing was conducted twice using distilled water for 10 min.
  • ultrasonic washing was conducted using isopropyl alcohol, acetone, and methanol solvents, and drying was then conducted. Next, it was transported to a plasma washing machine.
  • the substrate was washed using oxygen plasma for 5 min, and then transported to a vacuum evaporator.
  • Hexanitrile hexaazatriphenylene (hereinafter, referred to as "HAT") of the following Formula was vacuum deposited to a thickness of 500 A by heating on a transparent ITO electrode, which was prepared through the above procedure, so as to form a hole injection layer. [HAT]
  • the compound of Formula 2 which was prepared in Example 1, was vacuum deposited to a thickness of 400 A by heating on the hole injection layer so as to form a hole transport layer.
  • GH and GD as described below were vacuum deposited to a film thickness of 300 A at a film thickness ratio of 20:1 so as to form a light emitting layer.
  • the electron transport material as described below was vacuum deposited to a thickness of 200 A so as to form an electron injection layer and a electron transport layer, [electron transport material]
  • LiF Lithium fluoride
  • a forward current density of 4.7 V was appl ied to the 1 ight emitting device manufactured in the above, and as a result, the green light in which the color coordinate was (0.31, 0.64) at a current density of 50 mA/ciif was observed at 30 cd/A, and a life span to the luminance of 90% was 310 hours.
  • a forward current density of 4.5 V was applied to the light emitting device manufactured in the above, and as a result, the green light in which the color coordinate was (0.32, 0.65) at a current density of 50 mA/ciif was observed at 29 cd/A, and a life span to the luminance of 90% was 340 hours.
  • a forward current density of 4.7 V was appl ied to the 1 ight emitt ing device manufactured in the above, and as a result, the green light in which the color coordinate was (0.32, 0.64) at a current density of 50 mA/ ⁇ if was observed at 30 cd/A, and a life span to the luminance of 90% was 350 hours.
  • a forward current density of 4.6 V was applied to the light emitting device manufactured in the above, and as a result , the green light in which the color coordinate was (0.31, 0.65) at a current density of 50 mA/ ⁇ if was observed at 29 cd/A, and a life span to the luminance of was 330 hours.
  • a forward current density of 4.5 V was applied to the light emitting device manufactured in the above, and as a result , the green 1 ight in which the color coordinate was (0.32, 0.65) at a current density of 50 mA/ciif was observed at 29 cd/A, and a life span to the luminance of 90% was 370 hours.
  • a forward current density of 4.5 V was applied to the light emitting device manufactured in the above, and as a result, the green light in which the color coordinate was (0.32, 0.64) at a current density of 50 mA/ciif was observed at 27 cd/A, and a life span to the luminance of 90% was 140 hours.
  • the color coordinate was (0.32, 0.65) at a current density of 50 mA/cuf
  • the compound of the present invention is used in an organic light
  • the organic light emitting device that includes the

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Abstract

L'invention concerne un nouveau composé permettant d'augmenter considérablement la durée d'utilisation, l'efficacité, la stabilité électrochimique et la stabilité thermique d'un dispositif électroluminescent organique. L'invention concerne également un dispositif électroluminescent organique dans lequel le composé est inclus, ce composé étant inclus dans une couche de composés organiques.
PCT/KR2008/006564 2007-11-08 2008-11-07 Nouveau composé et dispositif électroluminescent organique contenant ce composé WO2009061145A1 (fr)

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US12/742,069 US8395143B2 (en) 2007-11-08 2008-11-07 Compound and organic light emitting device using the same
EP08847615.5A EP2215183B1 (fr) 2007-11-08 2008-11-07 Nouveau composé et dispositif électroluminescent organique contenant ce composé
CN200880119858.2A CN101896574B (zh) 2007-11-08 2008-11-07 新型化合物和使用该化合物的有机发光器件
JP2010533010A JP5562862B2 (ja) 2007-11-08 2008-11-07 新しい有機発光素子化合物およびこれを用いた有機発光素子

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KR10-2007-0113852 2007-11-08
KR20070113852 2007-11-08
KR1020080073238A KR20090048299A (ko) 2007-11-08 2008-07-25 새로운 유기 발광 소자 재료 및 이를 이용한 유기 발광소자
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JP2015213077A (ja) * 2015-06-22 2015-11-26 ユニバーサル ディスプレイ コーポレイション 溶液加工可能な、ドープされたトリアリールアミン正孔注入材料
JP2016048787A (ja) * 2010-03-08 2016-04-07 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機発光素子及びその製造方法
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CN104837834A (zh) * 2012-12-07 2015-08-12 出光兴产株式会社 芳香族胺衍生物和有机电致发光元件
WO2014087657A1 (fr) * 2012-12-07 2014-06-12 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique
US9966537B2 (en) 2014-12-29 2018-05-08 Dow Global Technologies Llc Compositions with 2,3-disubstituted indoles as charge transport materials, and display devices fabricated therefrom
WO2016107459A1 (fr) * 2014-12-29 2016-07-07 Dow Global Technologies Llc Compositions comprenant des indoles 2, 3-disubstitués comme matériaux de transport de charge, et dispositifs d'affichage fabriqués à partir de celles-ci
JP2015213077A (ja) * 2015-06-22 2015-11-26 ユニバーサル ディスプレイ コーポレイション 溶液加工可能な、ドープされたトリアリールアミン正孔注入材料
KR20230151999A (ko) 2021-02-26 2023-11-02 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광소자 및 전자 기기

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