WO2010058946A2 - Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés - Google Patents

Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés Download PDF

Info

Publication number
WO2010058946A2
WO2010058946A2 PCT/KR2009/006779 KR2009006779W WO2010058946A2 WO 2010058946 A2 WO2010058946 A2 WO 2010058946A2 KR 2009006779 W KR2009006779 W KR 2009006779W WO 2010058946 A2 WO2010058946 A2 WO 2010058946A2
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
aryl
hetero atom
Prior art date
Application number
PCT/KR2009/006779
Other languages
English (en)
Korean (ko)
Other versions
WO2010058946A3 (fr
Inventor
배재순
김정곤
김지은
장혜영
장준기
전상영
Original Assignee
주식회사 엘지화학
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 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP09827711.4A priority Critical patent/EP2351723B1/fr
Priority to JP2011537356A priority patent/JP5650654B2/ja
Priority to US13/129,768 priority patent/US9200196B2/en
Publication of WO2010058946A2 publication Critical patent/WO2010058946A2/fr
Publication of WO2010058946A3 publication Critical patent/WO2010058946A3/fr

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20Polycyclic condensed hydrocarbons
    • C07C15/38Polycyclic condensed hydrocarbons containing four rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/04Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24Anthracenes; Hydrogenated anthracenes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/04Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26Phenanthrenes; Hydrogenated phenanthrenes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/40Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/48Chrysenes; Hydrogenated chrysenes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/40Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/50Pyrenes; Hydrogenated pyrenes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1011Condensed systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1044Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1092Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14Carrier transporting layers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17Carrier injection layers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30Coordination compounds
    • H10K85/321Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/631Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00Energy generation through renewable energy sources
    • Y02E10/50Photovoltaic [PV] energy
    • Y02E10/549Organic PV cells
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50Manufacturing or production processes characterised by the final manufactured product

Definitions

  • the present invention relates to a novel chrysene derivative and an organic electric device using the same.
  • An organic electric device means a device requiring charge exchange between an electrode and an organic material using holes and / or electrons.
  • the organic electric element can be divided into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). Form of electrical elements.
  • the second type is an electrical device in which holes and / or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • organic electric element examples include an organic light emitting element, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and the like, all of which are used to inject or transport holes, inject or transport electrons, or light emitting materials to drive the device. need.
  • OPC organic photoconductor
  • a hole injection or transport material, an electron injection or transport material, or a light emitting material functions on a similar principle.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • organic light emitting devices When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes meet the electrons. When it falls back to the ground, it glows.
  • Such organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.
  • Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
  • a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material which constitutes the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.
  • a stable and efficient material is supported by a stable and efficient material.
  • the present invention is to solve the problems of the prior art as described above, an object of the present invention is to provide a stable and efficient novel chrysene derivative and an organic electric device using the same.
  • One aspect of the present invention for solving the above object provides a compound represented by the following formula (1).
  • R 1 is a substituted or unsubstituted C 1 ⁇ C 40 alkyl group; A substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group; A substituted or unsubstituted C 2 to C 40 heterocycloalkyl group; Substituted or unsubstituted C 2 Through C 40 Alkenyl group; Substituted or unsubstituted C 1 ⁇ C 40 Alkoxy group; Substituted or unsubstituted amino group; Substituted or unsubstituted C 6 Through C 40 An aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; And a substituted or unsubstituted and selected from the group consisting of C 3 ⁇ C 40 heteroarylamine group containing O, N or S as a hetero atom,
  • R2 is a substituted or unsubstituted C 1 ⁇ C 40 Alkyl group; A substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group; A substituted or unsubstituted C 3 ⁇ C 40 heterocycloalkyl group; Substituted or unsubstituted C 2 Through C 40 Alkenyl group; Substituted or unsubstituted C 1 ⁇ C 40 Alkoxy group; Substituted or unsubstituted amino group; Substituted or unsubstituted C 6 Through C 40 An aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; Substituted or unsubstituted C 5 Through C 40 An arylamine group; And a substituted or unsubstituted and selected from the group consisting of C 3 ⁇ C 40 heteroarylamine group containing O, N or S
  • R3 to R7 are each independently hydrogen; Substituted or unsubstituted C One Through C 40 Alkyl group; A substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group; A substituted or unsubstituted C 2 to C 40 heterocycloalkyl group containing O, N or S as a hetero atom; Substituted or unsubstituted C 2 Through C 40 Alkenyl group; Substituted or unsubstituted C 1 ⁇ C 40 Alkoxy group; Substituted or unsubstituted amino group; Substituted or unsubstituted C 6 Through C 40 An aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; Substituted or unsubstituted C 5 Through C 40 An arylamine group; And a substituted or unsubstituted and selected from the group consisting
  • X is hydrogen; Substituted or unsubstituted C One Through C 40 Alkyl group; A substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group; A substituted or unsubstituted C 2 to C 40 heterocycloalkyl group containing O, N or S as a hetero atom; Substituted or unsubstituted C 2 Through C 40 Alkenyl group; Substituted or unsubstituted C 1 ⁇ C 40 Alkoxy group; Substituted or unsubstituted amino group; Substituted or unsubstituted C 6 Through C 40 An aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; And a substituted or unsubstituted and selected from the group consisting of C 3 ⁇ C 40 heteroarylamine group containing O, N or S as a hetero atom, to form
  • R3 to R7 and X are hydrogen.
  • a second aspect of the present invention for achieving the above object is an organic electrical device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, one of the organic material layer Layer or more provides an organic electric device comprising the compound represented by the formula (1).
  • the compound according to the present invention may serve as hole injection, hole transport, electron injection and transport, or a light emitting material in an organic electric device including an organic light emitting device, and the organic electric device according to the present invention has efficiency, driving voltage, and stability. Excellent properties in terms of appearance.
  • FIG. 1 is a schematic diagram illustrating a structure of an organic light emitting device according to an exemplary embodiment of the present invention.
  • FIG. 2 is a graph showing excitation wavelengths and emission wavelengths in the film 200A of Compound 1-18.
  • One aspect of the present invention relates to a compound represented by Chemical Formula 1.
  • alkyl group, cycloalkyl group, heterocycloalkyl group, alkenyl group, alkoxy group, amino group, aryl group, heteroaryl group, arylamine group and heteroarylamine group in R2 to R7 are substituted with other functional groups, halogen, deuterium, amino group, Nitrile group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 1 to C 40 alkoxy group, C 3 to C 40 cycloalkyl group, hetero atoms include O, N or S To C 2 ⁇ C 40 Heterocycloalkyl group, C 6 ⁇ C 40 An aryl group and hetero atoms are substituted with one or more groups selected from the group consisting of C 3 ⁇ C 40 heteroaryl group containing O, N or S,
  • alkyl group, cycloalkyl group, heterocycloalkyl group, alkenyl group, alkoxy group, amino group, aryl group, heteroaryl group and heteroarylamine group in R1 and X are substituted with other functional groups, halogen, deuterium, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 2 ⁇ C 40 containing O, N or S as a hetero atom It is substituted with at least one group selected from the group consisting of a heterocycloalkyl group, C 6 ⁇ C 40 aryl group and C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom.
  • the alkyl group and the alkoxy group preferably have 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms. Moreover, it is preferable that carbon number is 2-40, and, as for an alkenyl group, it is more preferable that it is 2-20.
  • the aryl group preferably has 6 to 40 carbon atoms, and more preferably 6 to 20 carbon atoms.
  • the heterocyclic group preferably has 4 to 40 carbon atoms, and more preferably 4 to 20 carbon atoms.
  • the aryl amine group preferably has 6 to 60 carbon atoms, and more preferably 6 to 24 carbon atoms.
  • the heteroarylamine group preferably has 4 to 60 carbon atoms, and more preferably 4 to 20 carbon atoms.
  • substituted or unsubstituted is halogen, alkyl, alkenyl, alkoxy, aryl, arylalkyl, arylalkenyl, heterocyclic, carbazolyl, flu It is preferable to be substituted or unsubstituted with one or more substituents selected from the group consisting of an orenyl group, a nitrile group and an acetylene group, but is not limited thereto.
  • R 1 is a substituted or unsubstituted C 6 ⁇ C 40 aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; And a substituted or unsubstituted and selected from the group consisting of C 3 ⁇ C 40 heteroarylamine group containing O, N or S as a hetero atom,
  • R2 is a substituted or unsubstituted C 6 ⁇ C 40 aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; Substituted or unsubstituted C 5 Through C 40 An arylamine group; And it may be selected from the group consisting of a substituted or unsubstituted heteroarylamine group of C 3 ⁇ C 40 including O, N or S as a hetero atom.
  • R1 is a C 6 ⁇ C 20 aryl group; An aryl group of C 6 ⁇ C 40 aryl group or a heteroatom as O, N, or the containing S C 3 ⁇ C 40 heteroaryl group substituted by a C 6 ⁇ C 20; And it is selected from the group consisting of C 3 ⁇ C 20 heteroaryl substituted with an aryl group of C 6 ⁇ C 20 and containing O, N or S as a hetero atom,
  • R2 is C 6 ⁇ C 20 An aryl group; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it may be selected from the group consisting of C 6 ⁇ C 20 arylamine group.
  • R1 is preferably selected from the group consisting of substituents represented by the following structural formulas, but are not limited thereto.
  • R2 are preferably selected from the group consisting of substituents represented by the following structural formulas, but are not limited thereto.
  • R3 to R7 may be hydrogen, or four of R3 to R7 and X may be hydrogen.
  • X is a substituted or unsubstituted C 6 ⁇ C 40 aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; And it is preferably selected from the group consisting of a substituted or unsubstituted heteroarylamine group of C 3 ⁇ C 40 containing O, N or S as a hetero atom.
  • X is a C 6 ⁇ C 20 aryl group; An aryl group of C 6 ⁇ C 40 aryl group or a heteroatom as O, N, or the containing S C 3 ⁇ C 40 heteroaryl group substituted by a C 6 ⁇ C 20; And it is more preferably selected from the group consisting of C 3 ⁇ C 20 heteroaryl group substituted with a C 6 ⁇ C 20 aryl group and containing O, N or S as a hetero atom.
  • X are preferably selected from the group consisting of substituents represented by the following structural formulas, but are not limited thereto.
  • R3 to R7 and X are hydrogen
  • the substituent except for hydrogen in R3 to R7 is a substituted or unsubstituted C 6 ⁇ C 40 aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; Substituted or unsubstituted C 5 Through C 40 An arylamine group; And it is preferably selected from the group consisting of a substituted or unsubstituted heteroarylamine group of C 3 ⁇ C 40 containing O, N or S as a hetero atom.
  • R3 to R7 and X when four of R3 to R7 and X is hydrogen, the substituent except for hydrogen in R3 to R7 is a C 6 ⁇ C 20 aryl group; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it is more preferably selected from the group consisting of C 6 ⁇ C 20 arylamine groups.
  • R3 to R7 and X are hydrogen
  • the substituent except for hydrogen in R3 to R7 is preferably selected from the group consisting of substituents represented by the following structural formulas, but is not limited thereto.
  • R1 is a C 6 ⁇ C 20 aryl group; An aryl group of C 6 ⁇ C 40 aryl group or a heteroatom as O, N, or the containing S C 3 ⁇ C 40 heteroaryl group substituted by a C 6 ⁇ C 20; And C 6 ⁇ C 20 aryl group which is substituted heteroatom as O, N, or is selected from the group consisting of C 3 ⁇ C 20 heteroaryl group containing S; R2 is C 6 ⁇ C 20 An aryl group; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it is selected from the group consisting of C 6 ⁇ C 20 aryl group; An aryl group of
  • X and R7 are hydrogen, and at least one of R3 to R6 is an aryl group of C 6 to C 20 ; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it is preferably selected from the group consisting of C 6 ⁇ C 20 arylamine group.
  • R1 is a C 6 ⁇ C 20 aryl group; An aryl group of 6 C ⁇ C 40 aryl group or a heteroatom as O, N or S containing the C ⁇ 3 C 40 heteroaryl group substituted by a C 6 ⁇ 20 C; And C 6 ⁇ C 20 aryl group which is substituted heteroatom as O, N, or is selected from the group consisting of C 3 ⁇ C 20 heteroaryl group containing S; R2 is C 6 ⁇ C 20 An aryl group; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it is selected from the group consisting of C 6 ⁇ C 20 arylamine group;
  • R5 is C 6 ⁇ C 20 aryl group; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it is selected from the group consisting of C 6 ⁇ C 20 arylamine group,
  • R3, R4, R6, R7 and X are hydrogen, but are not limited thereto.
  • the compound represented by Chemical Formula 1 according to the present invention includes a functional group specific to at least one of R3 to R7, and X as well as R1 and R2, thereby having a compound having at least three functional groups centered on the chrysene core as a whole. Can be.
  • the organic electronic device containing such a compound in the case of including a specific functional group in the R1, R2 and R5 of the formula (1), can exhibit characteristics such as improved efficiency, drive voltage, stability have.
  • X and R3 to R7 may all be hydrogen.
  • the compound represented by Chemical Formula 1 may be prepared according to the method described below. First, Compound A is prepared according to the method of Journal of Organic Chemistry 2005,70, 3511-3517 as follows.
  • Compound A synthesized as described above connects two R1 and R2 functional groups through Suzuki coulpling to obtain Compound B or Compound C as a final target.
  • a second aspect of the present invention is an organic electrical device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers is the chemical formula It relates to an organic electric element comprising the compound of (1).
  • the organic material layer may include a hole injection layer and a hole transport layer, and the hole injection layer and the hole transport layer may include the compound of Formula 1.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the compound of Formula 1.
  • the organic material layer may include an electron transport layer
  • the electron transport layer may include the compound of Formula 1.
  • the organic electric element is preferably selected from the group consisting of an organic light emitting element, an organic solar cell, an organic photoconductor (OPC) and an organic transistor.
  • OPC organic photoconductor
  • the compound of Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of an organic electrical device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
  • the organic electric device of the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present invention, that is, the compound of Formula 1.
  • the organic material layer of the organic electric device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic electric device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic electric device is not limited thereto and may include a smaller number of organic material layers.
  • the organic electric element of the present invention may be manufactured by, for example, sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation may be used, but is not limited thereto.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer.
  • a material having high mobility to electrons is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compounds according to the present invention can also operate on principles similar to those applied to organic light emitting devices in organic electrical devices, including organic solar cells, organic photoconductors, organic transistors, and the like.
  • the compound represented by the formula (1) according to the present invention can generally be prepared by a multistage chemical reaction. That is, some intermediate compounds are prepared first, and compounds of formula 1 are prepared from the intermediate compounds. Exemplary intermediate compounds are the compounds described below. In these compounds, "Br" may be substituted with any other reactive atom or functional group.
  • Compound 1-7 (4.8 g, 73%) was prepared by the same method as Preparation Example 5, except that Compound S-7 (4.4 g, 8.7 mmol) was used instead of Compound S-4 in Preparation Example 5. It was.
  • the glass substrate coated with ITO indium tin oxide
  • ITO indium tin oxide
  • distilled water filtered secondly was used as a filter of the Millipore Co. company.
  • ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma and then transferred to a vacuum evaporator.
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • NPB 400 kPa
  • the compound 1-18 which was a host
  • the D1 compound which was a dopant
  • the following E1 compound was vacuum deposited to a thickness of 200 kPa on the light emitting layer to form an electron injection and transport layer.
  • a cathode was formed by sequentially depositing 12 ⁇ thick lithium fluoride (LiF) and 2,000 ⁇ thick aluminum on the electron injection and transport layer.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the lithium fluoride was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 to 7 ⁇ / sec.
  • Table 7 The results of evaluating the characteristics of the manufactured organic light emitting device are shown in Table 7 below.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 1-61, 1-6, 1-7, or 1-14 described in Table 7 was deposited instead of Compound 1-18.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the lithium fluoride was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 to 7 ⁇ / sec.
  • Table 7 The results of evaluating the characteristics of the manufactured organic light emitting device are shown in Table 7 below.
  • the organic electric device including the compound according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.
  • Example 1-1 except that using Compound 1-6, 1-7 or 1-14 shown in Table 8 as a host material in place of Compound 1-18 and using the following formula D2 as a dopant Example 1
  • An organic light emitting device was manufactured in the same manner as in ⁇ 1.
  • Example 1-1 an organic light emitting device was manufactured in the same manner as in Example 1-1, except for using Compound H2 as a host material as a dopant instead of Compound 1-18.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Photovoltaic Devices (AREA)

Abstract

L'invention concerne de nouveaux dérivés de chrysène et un dispositif électrique organique utilisant ces dérivés. Les dérivés de chrysène selon l'invention servent de substances pour injection et transport de trous, injection et transport d'électrons, ou émission de lumière dans un dispositif électrique organique comprenant un dispositif électroluminescent organique, et servent d'hôte électroluminescent ou de dopant, lorsqu'elles sont utilisées seules.
PCT/KR2009/006779 2008-11-18 2009-11-18 Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés WO2010058946A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP09827711.4A EP2351723B1 (fr) 2008-11-18 2009-11-18 Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés
JP2011537356A JP5650654B2 (ja) 2008-11-18 2009-11-18 新規なクリセン誘導体およびこれを用いた有機電子素子
US13/129,768 US9200196B2 (en) 2008-11-18 2009-11-18 Chrysene derivatives and organic electrical device using the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20080114661 2008-11-18
KR10-2008-0114661 2008-11-18

Publications (2)

Publication Number Publication Date
WO2010058946A2 true WO2010058946A2 (fr) 2010-05-27
WO2010058946A3 WO2010058946A3 (fr) 2010-08-19

Family

ID=42198650

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2009/006779 WO2010058946A2 (fr) 2008-11-18 2009-11-18 Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés

Country Status (5)

Country Link
US (1) US9200196B2 (fr)
EP (1) EP2351723B1 (fr)
JP (1) JP5650654B2 (fr)
KR (1) KR101137197B1 (fr)
WO (1) WO2010058946A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020039708A1 (fr) 2018-08-23 2020-02-27 国立大学法人九州大学 Élément électroluminescent organique

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104203941B (zh) * 2012-07-13 2017-03-01 株式会社Lg化学 杂环化合物及包含其的有机电子装置
KR102191991B1 (ko) 2013-09-06 2020-12-17 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
US9985579B2 (en) 2016-04-12 2018-05-29 Preformed Line Products Co. Mounting assembly for mounting a solar panel
KR102536248B1 (ko) 2017-06-21 2023-05-25 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자
KR102415376B1 (ko) 2017-08-04 2022-07-01 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR102536246B1 (ko) 2018-03-23 2023-05-25 삼성디스플레이 주식회사 헤테로고리 화합물 및 이를 포함한 유기 발광 소자
US20240107884A1 (en) * 2021-02-19 2024-03-28 Lg Chem, Ltd. Organic light emitting device
KR102697569B1 (ko) * 2023-09-22 2024-08-22 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080114661A (ko) 2008-11-25 2008-12-31 실리콘밸리(주) 실리콘 방열시트

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4117093B2 (ja) * 1998-12-28 2008-07-09 出光興産株式会社 有機エレクトロルミネッセンス素子用材料およびそれを使用した有機エレクトロルミネッセンス素子
WO2004018588A1 (fr) * 2002-07-19 2004-03-04 Idemitsu Kosan Co., Ltd. Dispositifs electroluminescents organiques et support luminescent organique
JP2004075567A (ja) * 2002-08-12 2004-03-11 Idemitsu Kosan Co Ltd オリゴアリーレン誘導体及びそれを利用した有機エレクトロルミネッセンス素子
JP2006052323A (ja) * 2004-08-12 2006-02-23 Sony Corp 有機材料、有機電界発光素子、および表示装置
JP2006052324A (ja) 2004-08-12 2006-02-23 Sony Corp 有機材料、有機電界発光素子、および表示装置
JP4263700B2 (ja) 2005-03-15 2009-05-13 出光興産株式会社 芳香族アミン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
EP1996540B1 (fr) * 2006-03-23 2015-07-08 LG Chem, Ltd. Dérivés de diamine, procédé d'élaboration et dispositif électronique organique y faisant appel
JP5414190B2 (ja) * 2007-04-02 2014-02-12 キヤノン株式会社 有機発光素子
US20080278072A1 (en) * 2007-04-30 2008-11-13 Lg Chem, Ltd. Organic light emitting device and method of producing the same
JP5473600B2 (ja) * 2007-07-07 2014-04-16 出光興産株式会社 クリセン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
JP2010241688A (ja) * 2007-07-07 2010-10-28 Idemitsu Kosan Co Ltd 非対称クリセン誘導体、有機el素子用材料、有機el素子用発光材料、及び、有機el素子
EP2213639B1 (fr) * 2007-11-19 2016-04-13 Idemitsu Kosan Co., Ltd. Dérivé de monobenzochrysène, matière de dispositif électroluminescent organique contenant celui-ci et dispositif électroluminescent organique utilisant la matière de dispositif électroluminescent organique
JP2010206078A (ja) * 2009-03-05 2010-09-16 Mitsui Chemicals Inc 有機トランジスタ

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080114661A (ko) 2008-11-25 2008-12-31 실리콘밸리(주) 실리콘 방열시트

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF ORGANIC CHEMISTRY, vol. 70, 2005, pages 3511 - 3517
See also references of EP2351723A4

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020039708A1 (fr) 2018-08-23 2020-02-27 国立大学法人九州大学 Élément électroluminescent organique

Also Published As

Publication number Publication date
EP2351723A2 (fr) 2011-08-03
EP2351723A4 (fr) 2012-08-01
WO2010058946A3 (fr) 2010-08-19
US20110227053A1 (en) 2011-09-22
EP2351723B1 (fr) 2014-02-26
JP5650654B2 (ja) 2015-01-07
KR101137197B1 (ko) 2012-04-20
KR20100056398A (ko) 2010-05-27
JP2012509317A (ja) 2012-04-19
US9200196B2 (en) 2015-12-01

Similar Documents

Publication Publication Date Title
WO2020045924A1 (fr) Nouveau composé et diode électroluminescente organique utilisant ce composé
WO2012173370A2 (fr) Composés originaux et dispositif électronique organique utilisant ces composés
WO2010005266A2 (fr) Nouveau dérivé d'anthracène et dispositif électronique organique utilisant un tel dérivé
WO2011037429A2 (fr) Composés ayant des dérivés hétérocycliques à cycle aryle condensé de 5 chaînons, dispositif électronique organique utilisant les composés, et terminal comprenant le dispositif électronique organique
WO2010131855A2 (fr) Composé contenant un hétérocycle à 5 éléments, diode électroluminescente organique dans laquelle il est employé, et borne destinée à cette dernière
WO2020050623A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2013129835A1 (fr) Diode électroluminescente organique
WO2010114267A2 (fr) Dispositif électronique organique, composés pour celui-ci et terminal
WO2011059271A2 (fr) Nouveau composé comprenant un anneau condensé, et dispositif électronique organique qui utilise celui-ci
WO2012091428A2 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2012099376A2 (fr) Nouveau composé et dispositif électroluminescent organique comprenant ledit composé
WO2010058946A2 (fr) Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés
WO2013129836A1 (fr) Diode électroluminescente organique
WO2010005268A2 (fr) Nouveau dérivé d'anthracène et dispositif organique électronique utilisant ledit dérivé
WO2011139125A2 (fr) Composé de phénanthrocarbazole, et dispositif électroluminescent organique utilisant ce composé
WO2011155742A2 (fr) Composé comprenant du carbazole et des dérivés d'amines aromatiques, élément électronique organique utilisant ce composé, et terminal comportant l'élément électronique organique
WO2011081431A2 (fr) Composé émetteur de lumière organique, et dispositif électroluminescent organique l'utilisant
WO2014123369A1 (fr) Nouveau composé et élément électronique organique l'utilisant
WO2011139129A2 (fr) Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant
WO2011149284A2 (fr) Composé contenant des hétéroatomes dans lequel un carbazole et un fluorène sont condensés, élément électrique organique l'utilisant et borne correspondante
WO2014084612A1 (fr) Nouveau composé et élément électronique organique l'utilisant
WO2019172649A1 (fr) Composé polycyclique et élément électroluminescent organique le comprenant
WO2014175627A1 (fr) Composé hétérocyclique contenant de l'azote et dispositif électronique organique comprenant ce composé
WO2020060288A1 (fr) Nouveau composé et diode électroluminescente organique l'utilisant
WO2019190239A1 (fr) Composé et diode électroluminescente organique le comprenant

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: 09827711

Country of ref document: EP

Kind code of ref document: A2

WWE Wipo information: entry into national phase

Ref document number: 13129768

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2011537356

Country of ref document: JP

Ref document number: 2009827711

Country of ref document: EP