[go: up one dir, main page]

WO2015178732A1 - Matériau hôte multi-composant et dispositif électroluminescent organique le contenant - Google Patents

Matériau hôte multi-composant et dispositif électroluminescent organique le contenant Download PDF

Info

Publication number
WO2015178732A1
WO2015178732A1 PCT/KR2015/005194 KR2015005194W WO2015178732A1 WO 2015178732 A1 WO2015178732 A1 WO 2015178732A1 KR 2015005194 W KR2015005194 W KR 2015005194W WO 2015178732 A1 WO2015178732 A1 WO 2015178732A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
unsubstituted
host
organic electroluminescent
aryl
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2015/005194
Other languages
English (en)
Inventor
Chi-Sik Kim
Seon-Woo Lee
Su-Hyun Lee
Young-Kwang Kim
Hee-Choon Ahn
Jae-Hoon Shim
Kyoung-Jin Park
Nam-Kyun Kim
Kyung-Hoon Choi
Young-Jun Cho
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DuPont Specialty Materials Korea Ltd
DuPont Electronic Materials International LLC
Original Assignee
Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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
Priority claimed from KR1020150070761A external-priority patent/KR20150135123A/ko
Application filed by Rohm and Haas Electronic Materials Korea Ltd, Rohm and Haas Electronic Materials LLC filed Critical Rohm and Haas Electronic Materials Korea Ltd
Priority to US15/311,537 priority Critical patent/US20170098784A1/en
Priority to CN202210131332.8A priority patent/CN114497425A/zh
Priority to CN201580026086.8A priority patent/CN106414662A/zh
Publication of WO2015178732A1 publication Critical patent/WO2015178732A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic 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
    • C07D491/02Heterocyclic 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 two hetero rings
    • C07D491/04Ortho-condensed systems
    • C07D491/044Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic 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 two hetero rings
    • C07D495/04Ortho-condensed 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
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/654Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • C09K2211/1007Non-condensed 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
    • C09K2211/1003Carbocyclic 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
    • 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
    • C09K2211/1059Heterocyclic compounds characterised by ligands containing three 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
    • C09K2211/1059Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C09K2211/1062Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with oxygen
    • 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
    • C09K2211/1059Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C09K2211/1066Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms 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
    • C09K2211/1088Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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
    • H10K2101/00Properties of the organic materials covered by group H10K85/00
    • H10K2101/10Triplet emission
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00Properties of the organic materials covered by group H10K85/00
    • H10K2101/90Multiple hosts in the emissive layer
    • 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
    • H10K85/341Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to a multi-component host material and an organic electroluminescence device comprising the same.
  • An electroluminescence device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • An organic EL device is a device changing electronic energy to light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode.
  • the organic layer of an organic EL device may be comprised of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (which comprises host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used for the organic layer are categorized by their functions in hole injection material, hole transport material, electron blocking material, light-emitting material, electron buffer material, hole blocking material, electron transport material, electron injection material, etc.
  • the organic EL device due to an application of a voltage, holes are injected from the anode to the light-emitting layer, electrons are injected from the cathode to the light-emitting layer, and excitons of high energies are formed by a recombination of the holes and the electrons.
  • excitons of high energies are formed by a recombination of the holes and the electrons.
  • luminescent organic compounds reach an excited state, and light emission occurs by emitting light from energy due to the excited state of the luminescent organic compounds returning to a ground state.
  • a light-emitting material must have high quantum efficiency, high electron and hole mobility, and the formed light-emitting material layer must be uniform and stable.
  • Light-emitting materials are categorized into blue, green, and red light-emitting materials dependent on the color of the light emission, additionally yellow or orange light-emitting materials.
  • light-emitting materials can also be categorized into host and dopant materials according to their functions.
  • the host material which acts as a solvent in a solid state and transfers energy needs to have high purity and a molecular weight appropriate for vacuum deposition. Furthermore, the host material needs to have high glass transition temperature and high thermal degradation temperature to achieve thermal stability, high electro-chemical stability to achieve long lifespan, ease of forming amorphous thin film, good adhesion to materials of adjacent layers, and non-migration to other layers.
  • a light-emitting material can be used as a combination of a host and a dopant to improve color purity, luminous efficiency, and stability.
  • an EL device having excellent characteristics has a structure comprising a light-emitting layer formed by doping a dopant to a host. Since host materials greatly influence the efficiency and lifespan of the EL device when using a dopant/host material system as a light emitting material, their selection is important.
  • Korean Patent Appln. Laying-Open No.10-2008-0080306 discloses an organic electroluminescent device using a compound wherein two carbazoles are linked via an arylene as a host material
  • International Publication No. WO 2013/112557 A1 discloses an organic electroluminescent device using a compound wherein a biscarbazole is linked to a carbazole via an arylene as a host material.
  • references fail to disclose an organic electroluminescent device using a compound wherein a biscarbazole comprising an aryl is linked to a dibenzothiophene or dibenzofuran directly or via an arylene, and a compound wherein a carbazole is linked to a heteroaryl directly or via an arylene as a multi-component host.
  • the objective of the present invention is to provide an organic electroluminescent device having improved lifespan characteristics.
  • an organic electroluminescent device comprising at least one light-emitting layer between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, the host consists of multi-component host compounds, at least a first host compound of the multi-component host compounds is represented by the following formula 1, and a second host compound is represented by the following formula 2:
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl
  • L 1 and L 2 each independently represent a single bond, or a substituted or unsubstituted (C6-C30)arylene;
  • X represents O or S
  • R 1 to R 32 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubsti
  • Ar 2 represents a substituted or unsubstituted 3- to 30-membered heteroaryl
  • the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.
  • an organic electroluminescent device having high efficiency and long lifespan is provided, and it is possible to manufacture a display device or a lighting device using the organic electroluminescent device.
  • organic electroluminescent device comprising the organic electroluminescent compounds of formulae 1 and 2 will be described in detail.
  • the compound represented by formula 1 can be represented by formula 3, 4, 5, or 6:
  • Ar 1 , L 1 , X, and R 1 to R 24 are as defined in formula 1.
  • L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene, preferably represents a single bond, or a substituted or unsubstituted (C6-C15)arylene, and more preferably represents a single bond, or an unsubstituted (C6-C15)arylene.
  • X represents O or S.
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, preferably represents a substituted or unsubstituted (C6-C20)aryl, and more preferably represents a (C6-C20)aryl unsubstituted or substituted with a (C6-C20)aryl.
  • R 1 to R 24 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubsti
  • L 2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene, preferably represents a single bond, or a substituted or unsubstituted (C6-C15)arylene, and more preferably represents a single bond, or a (C6-C15)arylene unsubstituted or substituted with a tri(C6-C15)arylsilyl.
  • Ar 2 represents a substituted or unsubstituted 3- to 30-membered heteroaryl, preferably represents a substituted or unsubstituted 5- to 11-membered nitrogen-containing heteroaryl, and more preferably represents a 6- to 10-membered nitrogen-containing heteroaryl unsubstituted or substituted with an unsubstituted (C6-C18)aryl, a (C6-C12)aryl substituted with a cyano, a (C6-C12)aryl substituted with a (C1-C6)alkyl, a (C6-C12)aryl substituted with a tri(C6-C12)arylsilyl, or a 6- to 15-membered heteroaryl.
  • Ar 2 may represent a monocyclic heteroaryl selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, or a fused heteroaryl selected from the group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, quinoxalinyl, carbazolyl, and phenanthrydinyl, and preferably may represent triazinyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, naphthyridinyl, or quiridine
  • R 25 to R 32 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubsti
  • L 1 and L 2 each independently can be represented by one of the following formulae 7 to 19:
  • Xi to Xp each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or un
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.;
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e. a substituent.
  • the triarylsilyl is preferably a triphenylsilyl.
  • the first host compound represented by formula 1 includes the following compounds, but is not limited thereto:
  • the second host compound represented by formula 2 includes the following compounds, but is not limited thereto:
  • the organic electroluminescent device comprises an anode; a cathode; and at least one organic layer between the anode and the cathode.
  • the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host and a phosphorescent dopant.
  • the host consists of multi-component host compounds, at least a first host compound of the multi-component host compounds is represented by formula 1, and a second host compound is represented by formula 2.
  • the light-emitting layer is a layer from which light is emitted, and can be a single layer or a multi layer of which two or more layers are stacked. In the light-emitting layer, it is preferable that the doping concentration of the dopant compound based on the host compound is less than 20 wt%.
  • the organic layer comprises a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the weight ratio of the first host material to the second host material is in the range of 1:99 to 99:1.
  • the dopant is preferably at least one phosphorescent dopant.
  • the dopant materials applied to the organic electroluminescent device according to the present invention are not limited, but may be preferably selected from metallated complex compounds of iridium, osmium, copper, and platinum, more preferably selected from ortho-metallated complex compounds of iridium, osmium, copper and platinum, and even more preferably ortho-metallated iridium complex compounds.
  • the phosphorescent dopant is preferably selected from compounds represented by the following formulae 101 to 103.
  • L is selected from the following structures:
  • R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
  • R 101 to R 109 , and R 111 to R 123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy; adjacent substituents of R 106 to R 109 may be linked to each other to form a substituted or unsubstituted, mono- or polycyclic, 3- to 30-membered alicyclic or (hetero)aromatic ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubsti
  • R 124 to R 127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R 124 to R 127 may be linked to each other to form a substituted or unsubstituted, mono- or polycyclic, 3- to 30-membered alicyclic or (hetero)aromatic ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl;
  • R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R 208 to R 211 may be linked to each other to form a substituted or unsubstituted, mono- or polycyclic, 3- to 30-membered alicyclic or (hetero)aromatic ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl;
  • f and g each independently represent an integer of 1 to 3; where f or g is an integer of 2 or more, each of R 100 may be the same or different; and
  • n an integer of 1 to 3.
  • the phosphorescent dopant materials include the following:
  • the organic electroluminescent device according to the present invention may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • a surface layer is preferably placed on an inner surface(s) of one or both electrode(s); selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
  • a chalcogenide (including oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • said chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a layer selected from a hole injection layer, a hole transport layer, or an electron blocking layer, or formed by a combination thereof can be used.
  • Multi layers can be used for the hole injection layer in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer. Two compounds can be simultaneously used in each layer.
  • the hole transport layer and the electron blocking layer can also be formed of multi layers.
  • a layer selected from an electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer, or formed by a combination thereof can be used.
  • Multi layers can be used for the electron buffer layer in order to control the injection of the electrons and enhance the interfacial characteristics between the light-emitting layer and the electron injection layer.
  • Two compounds can be simultaneously used in each layer.
  • the hole blocking layer and the electron transport layer can also be formed of multi layers, and each layer can comprise two or more compounds.
  • 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 is preferably placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
  • each layer of the organic electroluminescent device of the present invention dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
  • the first and second host compounds of the present invention may be co-evaporated or mixture-evaporated.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • the first and second host compounds of the present invention can be used to form a film by a co-evaporation of mixture-evaporation process.
  • a display system or a lighting system can be produced.
  • An OLED device was produced using the organic electroluminescent compound according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Geomatec) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 4 ,N 4' -diphenyl-N 4 ,N 4’ -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine (compound HI-1) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate.
  • 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (compound HI-2) was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine (compound HT-1) was then introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 70 nm on the second hole injection layer.
  • a first host compound and a second host compound were introduced into two cells of the vacuum vapor depositing apparatus, respectively.
  • a dopant compound D-96 was introduced into another cell.
  • the two host materials were evaporated at 1:1 rate, while the dopant was evaporated at a different rate from the host materials, so that the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
  • An OLED device was produced in the same manner as in Device Example 1-1, except for evaporating the first hole transport layer (compound HT-1) of 10 nm thickness, introducing N,N-di([1,1'-biphenyl]-4-yl)-4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine (compound HT-2) into another cell of said vacuum vapor depositing apparatus, evaporating by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer, and using the first and second host compounds listed in Table 1 as a host.
  • Comparative Example 1-1 Preparation of an OLED device using only the
  • An OLED device was produced in the same manner as in Device Example 1-1, except for using only the first host compound listed in Table 1 as a host of the light-emitting layer.
  • OLED device was produced in the same manner as in Device Examples 2-1 to 2-3, except for using only the second host compound listed in Table 1 as a host of the light-emitting layer.
  • the driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and the time taken for the luminance at 5,000 nit to be reduced from 100% to 90% at a constant current of the OLEDs produced as above were measured.
  • Table 1 below shows the luminous characteristics of the organic electroluminescent devices produced as in Device Example 1-1, Comparative Example 1-1, Device Examples 2-1 to 2-3, and Comparative Examples 2-1 to 2-3.
  • An OLED device was produced in the same manner as in Device Example 1-1, except for evaporating the second hole injection layer of 3 nm thickness, evaporating the first hole transport layer of 40 nm thickness, not evaporating the second hole transport layer, using compound D-1 or D-25 for the dopant of the light-emitting layer, evaporating the electron transport layer of 35 nm thickness at a rate of 4:6, and using the first and second host compounds combination listed in Table 2 as a host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 3-1 to 3-13, except for evaporating the first hole transport layer of 10 nm thickness, evaporating the second hole transport layer of 30 nm thickness by using compound HT-3, using compound D-136 for the dopant of the light-emitting layer, and using the first and second host compounds combination listed in Table 2 as a host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 3-1 to 3-13, except for using only the first host compound listed in Table 2 as a host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 3-1 to 3-13, except for using only the second host compound listed in Table 2 as a host of the light-emitting layer.
  • Comparative Example 5-1 Preparation of an OLED device using only the
  • An OLED device was produced in the same manner as in Device Example 4-1, except for using only the second host compound listed in Table 2 as a host of the light-emitting layer.
  • the driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and the time taken for the luminance at 15,000 nit to be reduced from 100% to 90% at a constant current of the OLEDs produced as above were measured.
  • Table 2 below shows the luminous characteristics of the organic electroluminescent devices produced as in Device Examples 3-1 to 3-13, Device Example 4-1, Comparative Example 3-1, Comparative Examples 4-1 to 4-12, and Comparative Example 5-1.
  • the organic electroluminescent device of the present invention comprises a light-emitting layer comprising a host and a phosphorus dopant, and the host consists of a specific combination of multi-component host compounds.
  • the device of the present invention provides superior lifespan characteristics to conventional devices.

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)

Abstract

La présente invention concerne un matériau hôte multi-composant et un dispositif électroluminescent organique le contenant. Grâce à une combinaison spécifique des composés hôtes multi-composant, le dispositif électroluminescent organique selon la présente invention peut offrir un haut rendement lumineux et d'excellentes caractéristiques de durée de vie.
PCT/KR2015/005194 2014-05-23 2015-05-22 Matériau hôte multi-composant et dispositif électroluminescent organique le contenant Ceased WO2015178732A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US15/311,537 US20170098784A1 (en) 2014-05-23 2015-05-22 Multi-component host material and an organic electroluminescence device comprising the same
CN202210131332.8A CN114497425A (zh) 2014-05-23 2015-05-22 多组分主体材料和包含其的有机电致发光器件
CN201580026086.8A CN106414662A (zh) 2014-05-23 2015-05-22 多组分主体材料和包含其的有机电致发光器件

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20140062376 2014-05-23
KR10-2014-0062376 2014-05-23
KR1020150070761A KR20150135123A (ko) 2014-05-23 2015-05-21 복수종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
KR10-2015-0070761 2015-05-21

Publications (1)

Publication Number Publication Date
WO2015178732A1 true WO2015178732A1 (fr) 2015-11-26

Family

ID=54554318

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2015/005194 Ceased WO2015178732A1 (fr) 2014-05-23 2015-05-22 Matériau hôte multi-composant et dispositif électroluminescent organique le contenant

Country Status (3)

Country Link
KR (1) KR20230028739A (fr)
CN (1) CN114497425A (fr)
WO (1) WO2015178732A1 (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106800552A (zh) * 2016-12-07 2017-06-06 烟台九目化学制品有限公司 一种3,3’联咔唑类衍生物有机电致发光材料及其应用
CN106986835A (zh) * 2016-01-21 2017-07-28 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置
WO2017200210A1 (fr) * 2016-05-17 2017-11-23 Rohm And Haas Electronic Materials Korea Ltd. Composé organique électroluminescent, matériau organique électroluminescent et dispositif organique électroluminescent les comprenant
JP2018024634A (ja) * 2016-07-28 2018-02-15 東ソー株式会社 新規なカルバゾール化合物及びその用途
CN107857772A (zh) * 2016-09-21 2018-03-30 三星Sdi株式会社 用于有机光电装置的化合物、用于有机光电装置的组合物及有机光电装置及显示装置
CN107880045A (zh) * 2016-09-29 2018-04-06 三星Sdi株式会社 用于有机光电装置的化合物、用于有机光电装置的组合物及有机光电装置及显示装置
CN108779120A (zh) * 2016-03-24 2018-11-09 德山新勒克斯有限公司 有机电子元件用化合物、利用该化合物的有机电子元件及其电子装置
CN109071553A (zh) * 2016-05-17 2018-12-21 罗门哈斯电子材料韩国有限公司 有机电致发光化合物、有机电致发光材料和包含其的有机电致发光装置
WO2019039428A1 (fr) * 2017-08-21 2019-02-28 出光興産株式会社 Élément électroluminescent organique, dispositif électronique, composition, matériau pour élément électroluminescent organique, et film de composition
JP2019514203A (ja) * 2016-04-18 2019-05-30 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 複数のホスト材料及びそれを含む有機電界発光デバイス
EP3525253A1 (fr) * 2018-02-13 2019-08-14 Samsung Display Co., Ltd Dispositif électroluminescent organique et afficheur incluant un dispositif électroluminescent organique
CN110662744A (zh) * 2017-05-23 2020-01-07 株式会社斗山 有机化合物及包含其的有机电致发光元件
EP3643761A1 (fr) * 2018-10-25 2020-04-29 Idemitsu Kosan Co., Ltd. Composition, matériau pour dispositif électroluminescent organique, film de composition, dispositif d'électroluminescence organique et dispositif électronique
JP2020516064A (ja) * 2017-04-03 2020-05-28 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機エレクトロルミネセントデバイス
US10840458B2 (en) 2016-05-25 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
CN113410407A (zh) * 2016-03-24 2021-09-17 德山新勒克斯有限公司 有机电子元件用化合物、利用该化合物的有机电子元件及其电子装置
US20220069229A1 (en) * 2018-12-21 2022-03-03 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
JP2023099504A (ja) * 2021-12-31 2023-07-13 エルジー ディスプレイ カンパニー リミテッド 発光素子及びこれを用いた発光表示装置
CN116813599A (zh) * 2022-03-18 2023-09-29 北京夏禾科技有限公司 有机电致发光材料及其器件

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023177217A1 (fr) 2022-03-18 2023-09-21 에스에프씨 주식회사 Nouveau composé hétérocyclique et diode électroluminescente organique le comprenant
WO2023182775A1 (fr) 2022-03-23 2023-09-28 에스에프씨 주식회사 Nouveau composé hétérocyclique et diode électroluminescente organique le comprenant
WO2024136206A1 (fr) 2022-12-20 2024-06-27 주식회사 엘지에너지솔루션 Dispositif de traitement de surface d'électrode et système de revêtement d'électrode le comprenant
KR20250074833A (ko) 2023-11-20 2025-05-28 에스에프씨 주식회사 신규한 헤테로고리 화합물 및 이를 포함하는 유기발광소자

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013062075A1 (fr) * 2011-10-26 2013-05-02 出光興産株式会社 Élément électroluminescent organique et matériau pour un élément électroluminescent organique
US20130234119A1 (en) * 2011-12-05 2013-09-12 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device
WO2013172835A1 (fr) * 2012-05-17 2013-11-21 Universal Display Corporation Matériaux hôtes dérivés du biscarbazole pour région électroluminescente d'oled
US20140001446A1 (en) * 2011-12-05 2014-01-02 Yumiko Mizuki Material for organic electroluminescence device and organic electroluminescence device
WO2014129869A1 (fr) * 2013-02-25 2014-08-28 주식회사 두산 Dispositif photo-émetteur à effet de champ organique

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007069569A1 (fr) 2005-12-15 2007-06-21 Idemitsu Kosan Co., Ltd. Materiau pour element a electroluminescence organique et element electroluminescent organique correspondant
WO2013112557A1 (fr) 2012-01-26 2013-08-01 Universal Display Corporation Dispositifs électroluminescents organiques phosphorescents ayant un co-matériau hôte transportant des trous dans la région émissive

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013062075A1 (fr) * 2011-10-26 2013-05-02 出光興産株式会社 Élément électroluminescent organique et matériau pour un élément électroluminescent organique
US20130234119A1 (en) * 2011-12-05 2013-09-12 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device
US20140001446A1 (en) * 2011-12-05 2014-01-02 Yumiko Mizuki Material for organic electroluminescence device and organic electroluminescence device
WO2013172835A1 (fr) * 2012-05-17 2013-11-21 Universal Display Corporation Matériaux hôtes dérivés du biscarbazole pour région électroluminescente d'oled
WO2014129869A1 (fr) * 2013-02-25 2014-08-28 주식회사 두산 Dispositif photo-émetteur à effet de champ organique

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106986835A (zh) * 2016-01-21 2017-07-28 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置
CN106986835B (zh) * 2016-01-21 2021-02-02 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置
US11339132B2 (en) 2016-01-21 2022-05-24 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same, and electronic device thereof
CN113410407B (zh) * 2016-03-24 2025-01-24 德山新勒克斯有限公司 有机电子元件用化合物、利用该化合物的有机电子元件及其电子装置
CN113410407A (zh) * 2016-03-24 2021-09-17 德山新勒克斯有限公司 有机电子元件用化合物、利用该化合物的有机电子元件及其电子装置
US10995069B2 (en) 2016-03-24 2021-05-04 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using same, and electronic device comprising same
CN108779120A (zh) * 2016-03-24 2018-11-09 德山新勒克斯有限公司 有机电子元件用化合物、利用该化合物的有机电子元件及其电子装置
JP2019514203A (ja) * 2016-04-18 2019-05-30 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 複数のホスト材料及びそれを含む有機電界発光デバイス
CN109071553A (zh) * 2016-05-17 2018-12-21 罗门哈斯电子材料韩国有限公司 有机电致发光化合物、有机电致发光材料和包含其的有机电致发光装置
JP2019519096A (ja) * 2016-05-17 2019-07-04 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機電界発光化合物、有機電界発光材料、及びそれを含む有機電界発光デバイス
CN109071553B (zh) * 2016-05-17 2022-05-27 罗门哈斯电子材料韩国有限公司 有机电致发光化合物、有机电致发光材料和包含其的有机电致发光装置
WO2017200210A1 (fr) * 2016-05-17 2017-11-23 Rohm And Haas Electronic Materials Korea Ltd. Composé organique électroluminescent, matériau organique électroluminescent et dispositif organique électroluminescent les comprenant
US10840458B2 (en) 2016-05-25 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
JP2018024634A (ja) * 2016-07-28 2018-02-15 東ソー株式会社 新規なカルバゾール化合物及びその用途
CN107857772A (zh) * 2016-09-21 2018-03-30 三星Sdi株式会社 用于有机光电装置的化合物、用于有机光电装置的组合物及有机光电装置及显示装置
CN107880045A (zh) * 2016-09-29 2018-04-06 三星Sdi株式会社 用于有机光电装置的化合物、用于有机光电装置的组合物及有机光电装置及显示装置
CN107880045B (zh) * 2016-09-29 2021-10-29 三星Sdi株式会社 用于有机光电装置的化合物、用于有机光电装置的组合物及有机光电装置及显示装置
CN106800552A (zh) * 2016-12-07 2017-06-06 烟台九目化学制品有限公司 一种3,3’联咔唑类衍生物有机电致发光材料及其应用
CN106800552B (zh) * 2016-12-07 2019-10-18 烟台九目化学制品有限公司 一种3,3’联咔唑类衍生物有机电致发光材料及其应用
JP2020516064A (ja) * 2017-04-03 2020-05-28 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機エレクトロルミネセントデバイス
JP7071404B2 (ja) 2017-05-23 2022-05-18 ソリュース先端素材株式会社 有機化合物およびこれを含む有機電界発光素子
JP2020520973A (ja) * 2017-05-23 2020-07-16 トゥサン ソーラス カンパニー リミテッドDoosan Solus Co., Ltd. 有機化合物およびこれを含む有機電界発光素子
US12225813B2 (en) 2017-05-23 2025-02-11 Doosan Solus Co., Ltd. Organic compound and organic electroluminescent device comprising the same
CN110662744A (zh) * 2017-05-23 2020-01-07 株式会社斗山 有机化合物及包含其的有机电致发光元件
CN110662744B (zh) * 2017-05-23 2023-12-01 斗山索如始株式会社 有机化合物及包含其的有机电致发光元件
WO2019039428A1 (fr) * 2017-08-21 2019-02-28 出光興産株式会社 Élément électroluminescent organique, dispositif électronique, composition, matériau pour élément électroluminescent organique, et film de composition
US11631817B2 (en) 2017-08-21 2023-04-18 Idemitsu Kosan Co., Ltd. Organic electroluminescence element, electronic device, composition, material for organic electroluminescence element, and composition film
US11355712B2 (en) 2018-02-13 2022-06-07 Samsung Display Co., Ltd. Organic light-emitting device and display apparatus including organic light-emitting device
EP3525253A1 (fr) * 2018-02-13 2019-08-14 Samsung Display Co., Ltd Dispositif électroluminescent organique et afficheur incluant un dispositif électroluminescent organique
CN110165087A (zh) * 2018-02-13 2019-08-23 三星显示有限公司 有机发光器件和包括有机发光器件的显示设备
EP3643761A1 (fr) * 2018-10-25 2020-04-29 Idemitsu Kosan Co., Ltd. Composition, matériau pour dispositif électroluminescent organique, film de composition, dispositif d'électroluminescence organique et dispositif électronique
US20220069229A1 (en) * 2018-12-21 2022-03-03 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
JP2023099504A (ja) * 2021-12-31 2023-07-13 エルジー ディスプレイ カンパニー リミテッド 発光素子及びこれを用いた発光表示装置
JP7662607B2 (ja) 2021-12-31 2025-04-15 エルジー ディスプレイ カンパニー リミテッド 発光素子及びこれを用いた発光表示装置
CN116813599A (zh) * 2022-03-18 2023-09-29 北京夏禾科技有限公司 有机电致发光材料及其器件

Also Published As

Publication number Publication date
KR20230028739A (ko) 2023-03-02
CN114497425A (zh) 2022-05-13

Similar Documents

Publication Publication Date Title
WO2015178732A1 (fr) Matériau hôte multi-composant et dispositif électroluminescent organique le contenant
EP3131879A1 (fr) Matériau hôte à plusieurs constituants et dispositif électroluminescent organique comprenant ledit matériau
WO2016080791A1 (fr) Matériaux hôtes multiples et dispositif électroluminescent organique les comprenant
WO2016013867A1 (fr) Dispositif électroluminescent organique
WO2016010402A1 (fr) Dispositif électroluminescent organique
EP3172780A1 (fr) Dispositif électroluminescent organique
WO2015167259A1 (fr) Matière hôte à constituants multiples et dispositif électroluminescent organique la comprenant
WO2016013875A1 (fr) Dispositif électroluminescent organique
EP3183234A1 (fr) Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux
WO2018105888A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2016036171A1 (fr) Pluralité de matériaux hôtes et dispositifs électroluminescents organiques les comprenant
EP3446345A1 (fr) Pluralité de matériaux hôtes et dispositif électroluminescent organique les comprenant
EP3140367A1 (fr) Matériau hôte à constituants multiples et dispositif électroluminescent organique comprenant ledit matériau
EP3129446A1 (fr) Matériau hôte à plusieurs composants et dispositif électroluminescent organique le comprenant
WO2015156587A1 (fr) Matériau hôte à plusieurs composants et dispositif électroluminescent organique le comprenant
EP3207045A1 (fr) Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux
WO2016076629A1 (fr) Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux
EP3268449A1 (fr) Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux
WO2016148390A1 (fr) Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux
WO2017183859A1 (fr) Pluralité de matériaux hôtes et dispositif électroluminescent organique les comprenant
EP3313958A1 (fr) Matériau hôte multicomposant et dispositif électroluminescent organique comprenant ce matériau
EP3494117A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2018021841A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2015174738A1 (fr) Matériau hôte à constituants multiples et dispositif électroluminescent organique le comprenant
WO2016208873A1 (fr) Matériau hôte multicomposant et dispositif électroluminescent organique comprenant ce matériau

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: 15795645

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 15311537

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 15795645

Country of ref document: EP

Kind code of ref document: A1