WO2011126225A1 - Nouveaux composés pour un matériau électronique organique et dispositif électroluminescent organique utilisant le même - Google Patents

Nouveaux composés pour un matériau électronique organique et dispositif électroluminescent organique utilisant le même Download PDF

Info

Publication number
WO2011126225A1
WO2011126225A1 PCT/KR2011/001920 KR2011001920W WO2011126225A1 WO 2011126225 A1 WO2011126225 A1 WO 2011126225A1 KR 2011001920 W KR2011001920 W KR 2011001920W WO 2011126225 A1 WO2011126225 A1 WO 2011126225A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
organic
compound
heteroaryl
aryl
Prior art date
Application number
PCT/KR2011/001920
Other languages
English (en)
Inventor
Soo Yong Lee
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Original Assignee
Rohm And Haas Electronic Materials Korea Ltd.
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 Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Publication of WO2011126225A1 publication Critical patent/WO2011126225A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms

Definitions

  • the present invention relates to novel compounds for organic electronic materials and an organic electroluminescent device using the same. More particularly, the compounds for organic electronic materials are used as transport materials.
  • electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
  • Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [ Appl. Phys. Lett. 51, 913, 1987].
  • An organic EL device is a device wherein, when charge is applied to an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole form a pair and then become extinct with emitting light.
  • a device can be formed on a transparent flexible substrate such as plastics. The device can be operated at a lower voltage (not more than 10 V) with relatively lower power consumption but excellent color purity, as compared to a plasma display panel or an inorganic EL display.
  • the electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
  • Organic electroluminescent materials are generally classified into high-molecular materials and low-molecular materials.
  • the low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, from the aspect of molecular structure.
  • Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained.
  • electroluminescent materials for red, green and blue
  • OLED organic light-emitting diode
  • the important issue is to develop red, green and blue electroluminescent materials with high efficiency and long life, in order to enhance the overall feature of the organic electroluminescent (EL) devices.
  • the EL materials are classified into host materials and dopant materials. It is generally known that a device structure having the most excellent EL properties can be fabricated with an EL layer prepared by doping a dopant to a host.
  • aluminum complexes such as tris(8-hydroxyquinoline)aluminum(III) (Alq) used before multi-layer thin film OLED, which was announced by Kodak in 1987, and beryllium complexes [T. Sato et.al. J. Mater. Chem. 10 (2000) 1151] such as bis(10-hydroxybenzo-[h]quinolinato)beryllium (Bebq) announced in Japan in the middle of 1990.
  • Alq tris(8-hydroxyquinoline)aluminum(III)
  • Bebq bis(10-hydroxybenzo-[h]quinolinato)beryllium
  • the noteworthy things of the conventional electron transport materials are that there are problems such as the slight improvement of only driving voltage differently from announcement, the significant deterioration of the device operation life, or the appearance of the side effect properties including deviation of the device operation life in each color and deterioration of thermal stability. It is the reality that the above-mentioned side effect properties have become a large obstacle in achieving the object such as increase of consumption power and brightness, which are hindrances in production of the large-sized OLED panel.
  • an object of the present invention is to provide novel compounds for organic electronic materials that weak points of the conventional electron transport materials are compensated, and that efficiency in electron transport, consumption power and device operation life are improved.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel the compounds for organic electronic materials.
  • the compound for organic electronic materials according to the present invention as electron transport materials exhibits excellent electron transport efficiency, it may prevent crystallization during the production of devices. Further, since it provides good layer formation, it may improve electrical current properties of devices. Therefore, it may be used to manufacture OLED devices having reduced driving voltage and improved power efficiency:
  • X represents -C(R 1 )(R 2 )-, -Si(R 3 )(R 4 )-, -S- or -O-;
  • R 1 through R 4 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl, or R 1 and R 2 or R 3 and R 4 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to from a spiro ring or a fused ring;
  • Ar 1 through Ar 4 independently represent hydrogen, (C1-C30)alkyl, halogen, di(C1-C30)alkylboranyl, di(C6-C30)arylboranyl, cyano, (C3-C30)cycloalkyl, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, carbazolyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(
  • the alkyl, aryl or heteroaryl of R 1 through R 4 and the alkyl, cycloalkyl, heterocycloalkyl, bicycloalkyl, alkylboranyl, arylboranyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, aralkyl, arylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of Ar 1 through Ar 4 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)
  • alkyl includes linear or branched saturated monovalent hydrocarbon radical containing only carbon atoms and hydrogen atoms, or a combination thereof.
  • alkoxy and alkylthio are respectively an -O-alkyl group and an -S-alkyl group, wherein alkyl is the same as defined above.
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryl groups having single bond(s) therebetween.
  • Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • the naphthyl includes 1-naphthyl and 2-naphthyl.
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • the heteroaryl also includes heteroaryl groups having single bond(s) therebetween.
  • the alkyl moiety of "(C1-C30)alkyl, di(C1-C30)alkylboranyl, mono- or di(C1-C30)alkylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkoxy" or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
  • the aryl moiety of "(C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio” or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
  • the heteroaryl of "(C3-C30)heteroaryl” may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
  • the cycloalkyl of "(C3-C30)cycloalkyl” may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
  • the alkenyl or alkynyl of "(C2-C30)alkenyl or alkynyl” may have 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
  • X represents -C(R 1 )(R 2 )-, -Si(R 3 )(R 4 )-, -S- or -O-;
  • R 1 through R 4 independently represent (C1-C30)alkyl or (C6-C30)aryl, or R 1 and R 2 or R 3 and R 4 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form a spiro ring or a fused ring;
  • R 1 and R 2 may be linked via alkylene or alkenylene with or without a fused ring to form a spiro ring or a fused ring but are not limited thereto.
  • R 3 and R 4 may be linked via alkylene or alkenylene with or without a fused ring to form a spiro ring or a fused ring but are not limited thereto.
  • Ar 1 through Ar 4 are independently selected from the group consisting of (C3-C30)cycloalkyl, morpholino, thiomorpholino, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C6-C30)aryloxy, (C3-C30)heteroaryl, carbazolyl, (C6-C30)arylthio, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl or tri(C6-C30)arylsilyl.
  • alkyl or aryl of R 1 through R 4 and the cycloalkyl, bicycloalkyl, alkenyl, alkynyl, aryl, aryloxy, heteroaryl, arylthio, trialkylsilyl, dialkylarylsilyl or triarylsilyl of Ar 1 through Ar 4 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl
  • the compounds for organic electronic materials according to the present invention may be exemplified by the compounds having following structures but are not limited thereto.
  • the compounds for organic electronic materials according to the present invention may be prepared as shown in following Scheme 1.
  • X and Ar 1 through Ar 4 are the same as defined in the Chemical Formula 1.
  • an organic electroluminescent device which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more compounds for organic electronic material(s) represented by Chemical Formula 1.
  • the compounds for organic electronic materials are used as a material of the electron transport layer.
  • the OLED consumption power is remarkably reduced due to the decrease of driving voltage and superior luminous efficiency is acquired.
  • the organic layer comprises one or more layer(s) including the compound for organic electric material represented by Chemical Formula 1 and one or more electroluminescent layer(s) including a fluorescent host and a fluorescent dopant or a phosphorescent host and a phosphorescent dopant.
  • the fluorescent host, fluorescent dopant, phosphorescent host or the phosphorescent dopant applied to the organic electroluminescent device of the present invention is not specifically limited.
  • the organic layer may further include, in addition to the compound for organic electric material represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
  • the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • the organic layer may further include, in addition to the compounds for organic electronic materials represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
  • the organic layer may include an electroluminescent layer and a charge generating layer.
  • the organic layer may include, in addition to the compound for organic electric material of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
  • the compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • a layer (hereinafter referred to as "surface layer" selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
  • the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
  • the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • the organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
  • the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
  • the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
  • Preferable oxidative dopants include various Lewis acids and acceptor compounds.
  • Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
  • the compound for organic electronic materials according to the present invention as electron transport materials exhibits excellent electron transport efficiency, it may prevent crystallization during the production of devices. Further, since it provides good layer formation, it may improve electrical current properties of devices. Therefore, it may be used to manufacture OLED devices having reduced driving voltage, improved power efficiency and the same or higher luminous efficiency.
  • the present invention is further described with respect to the compounds for organic electronic materials according to the present invention, processes for preparing the same, and luminescence properties of devices employing the same.
  • the following examples are provided for illustrative purposes only and they are not intended to limit the scope of the present invention.
  • Compound A-1 (16g, 0.082mol) was dissolved in acetic acid (400mL). Fuming nitric acid (172mL, 4.1mol) and sulfuric acid (43mL) were added using dropping funnel at 0°C and stirred for 24 hours. After filtering a produced solid under reduced pressure, the mixture was washed with acetic acid and distilled water. After distilling an obtained organic layer under reduced pressure and removing a solvent, Compound B-1 (16g, 81.5%) was obtained via purification by column chromatography.
  • Organic electroluminescent Compounds 1 to 66 were prepared according to Preparation Examples 1 to 3. Table 1 shows 1 H NMR and MS/FAB of the prepared organic electroluminescent compounds.
  • An OLED device was manufactured using the compound for organic electronic materials according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
  • N , N '-bis( ⁇ -naphthyl)- N , N '-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • an electroluminescent layer was formed thereon as follows. After respectively adding tris(8-hydroxyquinoline)-aluminum(III) (Alq3), which is an electroluminescent host as a luminous material in a cell of a vacuum vapor deposition apparatus and coumarin 545T as an electroluminescent dopant in another cell. The two cells were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer.
  • the doping concentration may be 2 to 5 mol% on the basis of Alq3.
  • the compound for organic electronic materials e.g. Compound 2
  • the compound for organic electronic materials e.g. Compound 2
  • Liq lithium quinolate
  • Al cathode having a thickness of 150 nm was formed using another vacuum vapor deposition apparatus to manufacture an OLED.
  • Each compound used in the OLED device as an electroluminescent material was purified by vacuum sublimation at 10 -6 torr.
  • the driving voltage and the luminous efficiencies of the OLED comprising the compound for organic electronic materials according to the present invention or the conventional electron transport materials in the Examples 1-5 and Comparative Example 1 were measured at 1,000 cd/m 2 , respectively, and the results are shown in Table 2.
  • An OLED device was manufactured using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
  • N , N '-bis( ⁇ -naphthyl)- N , N '-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • a compound according to the present invention (e.g.: Compound 7) purified by vacuum sublimation at 10 -6 torr was placed in a cell of a vacuum vapor deposition apparatus as a host, and an electroluminescent dopant (e.g.: Compound (piq) 2 Ir(acac)) was placed in another cell.
  • the two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer through doping at 4 to 10 wt%.
  • An OLED device was manufactured in the same manner as Example 8 except the hole blocking layer.
  • An OLED device was manufactured in the same manner as Example 6 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) instead of the compounds of the present invention as a host material at one cell of the vacuum vapor deposition apparatus.
  • CBP 4,4'-bis(carbazol-9-yl)biphenyl
  • the organic electroluminescent compounds according to the present invention have excellent luminous properties compared with the conventional material.
  • the organic electroluminescent compounds according to the present invention have excellent luminous properties compared with the conventional material. They have superior current properties compared with the device of Comparative Example 2 as the conventional material. They showed reduction of 0.2 V or more in a driving voltage and show high power efficiency of 1.1 times or more compared with the device of Comparative Example 2.
  • the compound for organic electronic materials according to the present invention as electron transport materials exhibits excellent electron transport efficiency, it may prevent crystallization during the production of devices. Further, since it provides good layer formation, it may improve electrical current properties of devices. Therefore, it may be used to manufacture OLED devices having reduced driving voltage, improved power efficiency and the same or higher luminous efficiency.

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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne de nouveaux composés pour un matériau électronique organique et un dispositif électroluminescent organique utilisant le même. Etant donné que le composé pour le matériau électrique organique montre une excellente efficacité de transport électronique, il peut prévenir la cristallisation durant la production des dispositifs. De plus, étant donné qu'il fournit une bonne formation de couches, il peut améliorer la propriété de courant électrique des dispositifs. Par conséquent, il peut être utilisé pour fabriquer des dispositifs OLED ayant une tension de polarisation dynamique réduite et un rendement énergétique amélioré.
PCT/KR2011/001920 2010-04-09 2011-03-21 Nouveaux composés pour un matériau électronique organique et dispositif électroluminescent organique utilisant le même WO2011126225A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020100032608A KR20110113297A (ko) 2010-04-09 2010-04-09 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2010-0032608 2010-04-09

Publications (1)

Publication Number Publication Date
WO2011126225A1 true WO2011126225A1 (fr) 2011-10-13

Family

ID=44763117

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2011/001920 WO2011126225A1 (fr) 2010-04-09 2011-03-21 Nouveaux composés pour un matériau électronique organique et dispositif électroluminescent organique utilisant le même

Country Status (3)

Country Link
KR (1) KR20110113297A (fr)
TW (1) TW201204729A (fr)
WO (1) WO2011126225A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102516284A (zh) * 2011-11-30 2012-06-27 杭州师范大学 含联三吡啶的取代噻咯类化合物及其制备和应用
JP2013234183A (ja) * 2012-05-03 2013-11-21 Samsung Display Co Ltd 縮合環化合物及びそれを含んだ有機発光素子
WO2014082705A1 (fr) 2012-11-30 2014-06-05 Merck Patent Gmbh Dispositif électronique
US20140319473A1 (en) * 2013-04-25 2014-10-30 Samsung Display Co., Ltd. Heterocyclic compound and organic light emitting device comprising the same
JP2015523377A (ja) * 2012-07-09 2015-08-13 ドゥーサン コーポレイション 新規な化合物及びこれを含む有機電界発光素子
WO2015147129A1 (fr) * 2014-03-26 2015-10-01 富士フイルム株式会社 Transistor organique, composé, matériau semi-conducteur organique pour dispositif à semi-conducteur organique non électroluminescent, matériau pour transistor organique, liquide de revêtement pour dispositif à semi-conducteur organique non électroluminescent, procédé de fabrication de transistor organique, procédé de fabrication de film semi-conducteur organique, film semi-conducteur organique pour dispositif à semi-conducteur organique non électroluminescent, et procédé de synthèse de matériau semi-conducteur organique
US9362507B2 (en) 2013-03-05 2016-06-07 Samsung Display Co., Ltd. Compound and organic light-emitting diode including the same
US9666809B2 (en) 2013-12-03 2017-05-30 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
US10115911B2 (en) 2014-03-26 2018-10-30 Fujifilm Corporation Coating solution for non-light-emitting organic semiconductor device, organic transistor, compound, organic semiconductor material for non-light-emitting organic semiconductor device, material for organic transistor, method for manufacturing organic transistor, and method for manufacturing organic semiconductor film
US10249829B2 (en) 2015-11-24 2019-04-02 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
US10367152B2 (en) 2015-11-26 2019-07-30 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US10790464B2 (en) 2017-05-17 2020-09-29 Samsung Display Co., Ltd. Organic light-emitting device
WO2020261938A1 (fr) * 2019-06-27 2020-12-30 富士フイルム株式会社 Élément de conversion photoélectrique, élément d'imagerie, capteur optique et matériau pour élément de conversion photoélectrique
US10985327B2 (en) * 2016-09-29 2021-04-20 Fujifilm Corporation Microcrystalline organic semiconductor film, organic semiconductor transistor, and method of manufacturing organic semiconductor transistor
CN114560875A (zh) * 2022-02-14 2022-05-31 西安凯翔光电科技有限公司 一种有机覆盖层材料和有机电致发光器件
US11834551B2 (en) 2016-04-15 2023-12-05 Beckman Coulter, Inc. Photoactive macromolecules and uses thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101671932B1 (ko) * 2013-06-20 2016-11-03 제일모직 주식회사 유기 광전자 소자용 화합물, 이를 포함하는 유기 광전자 소자 및 상기 유기 광전자 소자를 포함하는 표시장치
KR102623053B1 (ko) 2018-12-05 2024-01-10 삼성디스플레이 주식회사 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011010844A1 (fr) * 2009-07-23 2011-01-27 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant ceux-ci

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011010844A1 (fr) * 2009-07-23 2011-01-27 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant ceux-ci

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
GUO, J.-G. ET AL.: "New fluorene derivatives based on 3,9-dihydrofluoreno[3,2- d]imidazole (FI): Characterization and influence of substituents on photoluminescence", JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A: CHEMISTRY., vol. 219, 2011, pages 42 - 49 *
LI, X. ET AL.: "2,3,6,7-tetraamino-9,9-bis(2-ethylhexyl)fluorene: New multifunctional monomer for soluble ladder-conjugated molecules and polymers", ORGANIC LETTERS., vol. 10, 2008, pages 2885 - 2888 *

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102516284B (zh) * 2011-11-30 2015-01-28 杭州师范大学 含联三吡啶的取代噻咯类化合物及其制备和应用
CN102516284A (zh) * 2011-11-30 2012-06-27 杭州师范大学 含联三吡啶的取代噻咯类化合物及其制备和应用
JP2013234183A (ja) * 2012-05-03 2013-11-21 Samsung Display Co Ltd 縮合環化合物及びそれを含んだ有機発光素子
EP2666768A2 (fr) * 2012-05-03 2013-11-27 Samsung Display Co., Ltd. Composé cyclique condensé et diode électroluminescente organique le comprenant
EP2666768A3 (fr) * 2012-05-03 2014-04-09 Samsung Display Co., Ltd. Composé cyclique condensé et diode électroluminescente organique le comprenant
US10249824B2 (en) 2012-05-03 2019-04-02 Samsung Display Co., Ltd. Condensed-cyclic compound and organic light-emitting diode comprising the same
JP2015523377A (ja) * 2012-07-09 2015-08-13 ドゥーサン コーポレイション 新規な化合物及びこれを含む有機電界発光素子
US10236451B2 (en) 2012-07-09 2019-03-19 Doosan Corporation Compound and organic electroluminescent device comprising the same
CN104813496B (zh) * 2012-11-30 2017-08-08 默克专利有限公司 电子器件
CN104813496A (zh) * 2012-11-30 2015-07-29 默克专利有限公司 电子器件
WO2014082705A1 (fr) 2012-11-30 2014-06-05 Merck Patent Gmbh Dispositif électronique
JP2016501447A (ja) * 2012-11-30 2016-01-18 メルク パテント ゲーエムベーハー 電子素子
US10065959B2 (en) 2012-11-30 2018-09-04 Merck Patent Gmbh Electronic device
US9362507B2 (en) 2013-03-05 2016-06-07 Samsung Display Co., Ltd. Compound and organic light-emitting diode including the same
US20140319473A1 (en) * 2013-04-25 2014-10-30 Samsung Display Co., Ltd. Heterocyclic compound and organic light emitting device comprising the same
US9502663B2 (en) * 2013-04-25 2016-11-22 Samsung Display Co., Ltd. Heterocyclic compound and organic light emitting device comprising the same
US9666809B2 (en) 2013-12-03 2017-05-30 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
WO2015147129A1 (fr) * 2014-03-26 2015-10-01 富士フイルム株式会社 Transistor organique, composé, matériau semi-conducteur organique pour dispositif à semi-conducteur organique non électroluminescent, matériau pour transistor organique, liquide de revêtement pour dispositif à semi-conducteur organique non électroluminescent, procédé de fabrication de transistor organique, procédé de fabrication de film semi-conducteur organique, film semi-conducteur organique pour dispositif à semi-conducteur organique non électroluminescent, et procédé de synthèse de matériau semi-conducteur organique
US10115911B2 (en) 2014-03-26 2018-10-30 Fujifilm Corporation Coating solution for non-light-emitting organic semiconductor device, organic transistor, compound, organic semiconductor material for non-light-emitting organic semiconductor device, material for organic transistor, method for manufacturing organic transistor, and method for manufacturing organic semiconductor film
KR20160126040A (ko) 2014-03-26 2016-11-01 후지필름 가부시키가이샤 유기 트랜지스터, 화합물, 비발광성 유기 반도체 디바이스용 유기 반도체 재료, 유기 트랜지스터용 재료, 비발광성 유기 반도체 디바이스용 도포액, 유기 트랜지스터의 제조 방법, 유기 반도체막의 제조 방법, 비발광성 유기 반도체 디바이스용 유기 반도체막, 유기 반도체 재료의 합성 방법
JP2015195362A (ja) * 2014-03-26 2015-11-05 富士フイルム株式会社 有機トランジスタ、化合物、非発光性有機半導体デバイス用有機半導体材料、有機トランジスタ用材料、非発光性有機半導体デバイス用塗布液、有機トランジスタの製造方法、有機半導体膜の製造方法、非発光性有機半導体デバイス用有機半導体膜、有機半導体材料の合成方法
US10270043B2 (en) 2014-03-26 2019-04-23 Fujifilm Corporation Organic transistor, compound, organic semiconductor material for non-light-emitting organic semiconductor device, material for organic transistor, coating solution for non-light-emitting organic semiconductor device, method for manufacturing organic transistor, method for manufacturing organic semiconductor film, organic semiconductor film for non-light-emitting organic semiconductor device, and method for synthesizing organic semiconductor material
US10270044B2 (en) 2014-03-26 2019-04-23 Fujifilm Corporation Coating solution for non-light-emitting organic semiconductor device, organic transistor, compound, organic semiconductor material for non-light-emitting organic semiconductor device, material for organic transistor, method for manufacturing organic transistor, and method for manufacturing organic semiconductor film
US10276806B2 (en) 2014-03-26 2019-04-30 Fujifilm Corporation Coating solution for non-light-emitting organic semiconductor device, organic transistor, compound, organic semiconductor material for non-light-emitting organic semiconductor device, material for organic transistor, method for manufacturing organic transistor, and method for manufacturing organic semiconductor film
US10249829B2 (en) 2015-11-24 2019-04-02 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
US10367152B2 (en) 2015-11-26 2019-07-30 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US11834551B2 (en) 2016-04-15 2023-12-05 Beckman Coulter, Inc. Photoactive macromolecules and uses thereof
US10985327B2 (en) * 2016-09-29 2021-04-20 Fujifilm Corporation Microcrystalline organic semiconductor film, organic semiconductor transistor, and method of manufacturing organic semiconductor transistor
US10790464B2 (en) 2017-05-17 2020-09-29 Samsung Display Co., Ltd. Organic light-emitting device
WO2020261938A1 (fr) * 2019-06-27 2020-12-30 富士フイルム株式会社 Élément de conversion photoélectrique, élément d'imagerie, capteur optique et matériau pour élément de conversion photoélectrique
JPWO2020261938A1 (fr) * 2019-06-27 2020-12-30
JP7386244B2 (ja) 2019-06-27 2023-11-24 富士フイルム株式会社 光電変換素子、撮像素子、光センサ、光電変換素子用材料
CN114560875A (zh) * 2022-02-14 2022-05-31 西安凯翔光电科技有限公司 一种有机覆盖层材料和有机电致发光器件

Also Published As

Publication number Publication date
KR20110113297A (ko) 2011-10-17
TW201204729A (en) 2012-02-01

Similar Documents

Publication Publication Date Title
WO2011126225A1 (fr) Nouveaux composés pour un matériau électronique organique et dispositif électroluminescent organique utilisant le même
WO2012050371A1 (fr) Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant
WO2011019156A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2011132866A1 (fr) Nouveaux composés pour matière électronique organique et dispositif électroluminescent organique utilisant ceux-ci
WO2011126224A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les employant
WO2014142467A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant le composé, et dispositif électronique comprenant l'élément électronique organique
WO2011136520A1 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent associé
WO2011136484A1 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent associé
WO2010114264A2 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant
WO2012173371A2 (fr) Composés originaux et dispositif électronique organique utilisant ces composés
WO2010126234A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2012050347A1 (fr) Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant
WO2010114256A2 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2010126270A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2011010842A2 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique associé
WO2011055911A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2013109030A1 (fr) Dispositif électroluminescent organique comprenant les composés électroluminescents organiques
WO2011010839A1 (fr) Nouveau composé organique électroluminescent et dispositif organique électroluminescent utilisant ce dernier
WO2012011756A1 (fr) Nouveaux composés organiques électroluminescents et dispositifs organiques électroluminescents les comprenant
WO2011099718A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2011115378A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2011071255A1 (fr) Nouveaux composés électroluminescents organiques et dispositif à diodes électroluminescentes organiques les utilisant
WO2010114253A2 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant
WO2015012618A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2011010843A1 (fr) Composés électroluminescents organiques innovants et dispositif électroluminescent organique les utilisant

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: 11766076

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11766076

Country of ref document: EP

Kind code of ref document: A1