US20210395215A1 - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Organic electroluminescent compound and organic electroluminescent device comprising the same Download PDF

Info

Publication number
US20210395215A1
US20210395215A1 US17/287,951 US201917287951A US2021395215A1 US 20210395215 A1 US20210395215 A1 US 20210395215A1 US 201917287951 A US201917287951 A US 201917287951A US 2021395215 A1 US2021395215 A1 US 2021395215A1
Authority
US
United States
Prior art keywords
organic electroluminescent
substituted
unsubstituted
aryl
layer
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.)
Abandoned
Application number
US17/287,951
Other languages
English (en)
Inventor
Chi-Sik Kim
Soo-yong Lee
Seung-Hoon Yoo
Dong-Hyung Lee
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.)
Rohm and Haas Electronic Materials Korea Ltd
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
Priority claimed from PCT/KR2019/014150 external-priority patent/WO2020085845A1/en
Publication of US20210395215A1 publication Critical patent/US20210395215A1/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic 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
    • C07D405/02—Heterocyclic 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 two hetero rings
    • C07D405/10—Heterocyclic 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 two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • H01L51/0058—
    • H01L51/0072—
    • H01L51/0073—
    • H01L51/0074—
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • H01L51/5012—

Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • An electroluminescent (EL) 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.
  • An organic EL device was first developed by Eastman Kodak in 1987, 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 electroluminescent device changes electric energy into light by applying electricity to an organic light-emitting material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
  • the organic layer of the OLED may comprise a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (containing host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • the materials used in the organic layer can be classified into a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc., depending on functions.
  • a voltage 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.
  • organic luminescent compounds reach an excited state, and light emission occurs by emitting light from energy due to the excited state of the organic luminescent compounds returning to a ground state.
  • blue light-emitting materials materials such as ADN and DPVBi are used as a host material, and materials such as aromatic amine-based compounds, copper phthalocyanine compounds, carbazole-based derivatives, perylene-based derivatives, coumarin-based derivatives, and pyrene-based derivatives are used as a dopant material.
  • these materials are difficult to obtain a deep blue color with high color purity, and are problematic due to having shorter light-emitting lifespan as the wavelength gets shorter.
  • U.S. Pat. No. 8,759,818 and U.S. Patent Application Publication No. 2014/0001459 disclose an organic electroluminescent compound comprising an anthracene moiety in which some hydrogen atoms are substituted with deuterium.
  • these references do not specifically disclose an organic electroluminescent compound comprising an anthracene moiety in which some hydrogen atoms are substituted with deuterium, and wherein a dibenzofuran is substituted in a certain position.
  • the objective of the present disclosure is firstly. to provide an organic electroluminescent compound effective for producing an organic electroluminescent device having excellent lifespan characteristic, and secondly, to provide an organic electroluminescent device comprising the organic electroluminescent compound.
  • an improvement of a blue light-emitting material or blue light-emitting device is important.
  • a compound having a main moiety of anthracene as a blue host material.
  • lifespan characteristics of a blue light-emitting material or blue light-emitting device there was a limit in improving lifespan characteristics of a blue light-emitting material or blue light-emitting device.
  • the stability of an anthracene compound comprised in the blue host material can be increased.
  • One of the methods is deuteration. When deuterating an anthracene compound, the zero point vibration energy of the compound can be lowered, thereby increasing the bond dissociation energy (BDE) of the compound.
  • FIG. 1 is a graph showing the increase of the bond dissociation energy due to deuteration.
  • the present inventors found that when deuterating the organic electroluminescent compound having a specific structure of the following formula 1, a more noticeable improvement in lifespan results compared to anthracene compounds having other structures.
  • the mobilities of holes and/or electrons can be improved, thereby decreasing the driving voltage.
  • R 1 to R 8 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 0-membered)heteroaryl, with a proviso that one of R 2 to R 4 is bonded to
  • R 9 to R 18 each independently represent hydrogen or deuterium
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • D N means that N hydrogen atoms are substituted with deuterium
  • N represents an integer of 8 to 50.
  • organic electroluminescent compound according to the present disclosure it is possible to produce an organic electroluminescent device having improved blue light-emitting lifespan.
  • FIG. 1 is a graph illustrating an increase of the bond dissociation energy due to deuteration.
  • organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
  • the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • the organic electroluminescent material of the present disclosure may comprise at least one compound represented by formula 1.
  • the compound represented by formula 1 may be comprised in a light-emitting layer or a hole transport layer, but is not limited thereto.
  • the compound represented by formula 1 when comprised in a light-emitting layer, may be comprised as a host such as a host for blue light-emission.
  • the compound of formula 1 may be a fluorescent host, for example, a fluorescent host for blue light-emission.
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10.
  • the above alkyl may include methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, etc.
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10.
  • (C3-C30)cycloalkyl is meant to be a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7.
  • the above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (3- to 7-membered)heterocycloalkyl is meant to be a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O. S, and N.
  • the above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl is meant to be a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18.
  • the above aryl may be partially saturated, and may comprise a spiro structure.
  • the above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenyinaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, azulenyl, etc.
  • the aryl may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluoren
  • (3- to 30-membered)heteroaryl is an aryl group having 3 to 30 ring backbone atoms, and including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P.
  • the above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and may comprise a spiro structure.
  • the above heteroaryl may include a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzimidazolyl, benzothiazolyl, naphtho
  • the heteroaryl may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 5-imidazopyr
  • ortho indicates that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2, it is called an ortho position.
  • Meta indicates that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, it is called a meta position.
  • Para indicates that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, it is called a para position.
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e., a substituent.
  • the substituents of the substituted alkyl, the substituted aryl, and the substituted heteroaryl in R, to Re, and Ar 1 each independently are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalken
  • the substituents each independently are at least one selected from the group consisting of a (C1-C6)alkyl, a (C6-C15)aryl, and a (5- to 15-membered)heteroaryl.
  • the substituents each independently may be at least one selected from the group consisting of a methyl, a phenyl, a naphthyl, a biphenyl, and a carbazolyl.
  • the compound represented by formula 1 may be represented by any one of the following formulas 1-1 to 1-3:
  • R 1 to R 8 , R 9 to R 16 , Ar 1 , and D N are as defined in formula 1, and
  • N represents an integer of 8 to 30.
  • R 1 to Re each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, with a proviso that one of R 2 to R 4 is bonded to
  • one of R 2 to R 4 is bonded to
  • R 2 to R 4 , R 1 , and R 5 to R 8 each independently represent hydrogen or deuterium.
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl. In one embodiment of the present disclosure. Ar 1 represents a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl.
  • Ar 1 represents a (C6-C25)aryl unsubstituted or substituted with at least one of a (C1-C6)alkyl(s), a (C6-C15)aryl(s), and a (5- to 15-membered)heteroaryl(s); or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl(s).
  • Ar 1 may represent a phenyl, a naphthyl, a biphenyl, a terphenyl, a phenanthrenyl, a naphthylphenyl, a phenyinaphthyl, a binaphthyl, a biphenylnaphthyl, a dimethylfluorenyl, a dimethylbenzofluorenyl, a carbazolylphenyl, a carbazolyinaphthyl, a phenylbenzothiazolyl, a phenylbenzooxazolyl, a dibenzothiophenyl, a phenylcarbazolyl, a phenylnaphthothiazolyl, a benzonaphthofuranyl, a phenylbenzocarbazolyl, a 19-membered nitrogen-containing heteroaryl, etc.
  • D N means that N hydrogen atoms in formula 1 are substituted with deuterium.
  • N represents an integer of 8 to 50, preferably an integer of 8 to 40, more preferably an integer of 8 to 30, and even more preferably an integer of 13 to 30.
  • the upper limit is determined according to the number of hydrogen atoms which can be substituted in each compound.
  • Ar 1 represents a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl.
  • Ar 1 represents a (C6-C25)aryl unsubstituted or substituted with at least one of a (C1-C6)alkyl(s), a (C6-C15)aryl(s), and a (5- to 15-membered)heteroaryl(s); or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl(s).
  • the ring may be a substituted or unsubstituted mono- or polycyclic (3- to 30-membered) alicyclic or aromatic ring, or the combination thereof, in which the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and R preferably N, O, and S.
  • the number of the ring backbone atoms may be 5 to 20. According to another embodiment of the present disclosure, the number of the ring backbone atoms may be 5 to 15.
  • the fused ring may be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.
  • the heteroaryl each independently, may contain at least one heteroatom selected from B, N, O, S, Si, and P.
  • the heteroatom may be bonded to at least one selected from the group consisting of hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted di
  • the compound represented by formula 1 includes the following compounds, but is not limited thereto.
  • the compound of formula 1 according to the present disclosure may be prepared by a synthetic method known to one skilled in the art, and for example, as shown in the following reaction schemes but is not limited thereto.
  • the non-deuterated derivative of the compound represented by formula 1 may be prepared by a known coupling or substitution reaction.
  • the deuterated derivative may be prepared by a similar method using a deuterated precursor material, or more generally, treating a non-deuterated compound with a deuterated solvent, D6-benzene, etc., in the presence of a Lewis acid such as aluminum trichloride or ethyl aluminum chloride, a H/D exchange catalyst such as trifluoromethanesulfonic acid or trifluoromethanesulfonic acid-D, etc.
  • a Lewis acid such as aluminum trichloride or ethyl aluminum chloride
  • a H/D exchange catalyst such as trifluoromethanesulfonic acid or trifluoromethanesulfonic acid-D, etc.
  • the degree of deuteration may be controlled by varying reaction conditions such as reaction temperature. For example, by controlling reaction temperature and time, acid equivalent, etc., the number of N in formula 1 may be controlled
  • the present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound represented by formula 1, and an organic electroluminescent device comprising the organic electroluminescent material.
  • the material may consist of the organic electroluminescent compound according to the present disclosure alone, or may further comprise conventional materials included in the organic electroluminescent material.
  • the organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between the first and second electrodes, in which the organic layer may comprise at least one organic electroluminescent compound represented by formula 1.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the second electrode may be a a transflective electrode or a reflective electrode
  • the organic electroluminescent device may be a top emission type, a bottom emission type, or both-sides emission type according to the kinds of the material formed.
  • the first electrode and the second electrode may each be formed with a transmissive conductive material, a transflective conductive material, or a reflective conductive material.
  • the organic electroluminescent device may be a top emission type, a bottom emission type, or both-sides emission type according to the kinds of the material forming the first electrode and the second electrode.
  • the hole injection layer may be further doped with a p-dopant, and the electron injection layer may be further doped with an n-dopant.
  • the organic electroluminescent compound represented by formula 1 of the present disclosure may be comprised in at least one of a light-emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer, preferably, may be comprised in a light-emitting layer.
  • the organic electroluminescent compound represented by formula 1 of the present disclosure may be comprised as a host material.
  • the light-emitting layer may further comprise at least one dopant.
  • the organic electroluminescent compound of the present disclosure may be used as a co-host material. That is, the light-emitting layer may further include a compound other than the organic electroluminescent compound represented by formula 1 of the present disclosure (first host material) as a second host material.
  • first host material a compound other than the organic electroluminescent compound represented by formula 1 of the present disclosure
  • second host material The weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1.
  • the dopant comprised in the organic electroluminescent device of the present disclosure is at least one phosphorescent or fluorescent dopant, preferably at least one fluorescent dopant.
  • the fluorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particulary limited.
  • the organic layer may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • 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.
  • the organic electroluminescent device of the present disclosure may emit white light by further including at least one light-emitting layer containing a blue, red, or green light-emitting compound, which is known in the art, besides the organic electroluminescent compound of the present disclosure. In addition, it may further include a yellow or orange light-emitting layer, if necessary.
  • a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be preferably placed on an inner surface(s) of one or both electrodes.
  • 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.
  • the surface layer may provide operation stability for the organic electroluminescent device.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.
  • the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
  • the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof may be used between the anode and the light-emitting layer.
  • the hole injection layer may be multilayers 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, wherein each of the multilayers may use two compounds simultaneously.
  • the hole transport layer or the electron blocking layer may also be multilayers.
  • An electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode.
  • the electron buffer layer may be multilayers in order to control the injection of the electron and improve the interfacial properties between the light-emitting layer and the electron injection layer, wherein each of the multilayers may use two compounds simultaneously.
  • the hole blocking layer or the electron transport layer may also be multilayers, wherein each of the multilayers may use a plurality of compounds.
  • the light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer.
  • the light-emitting auxiliary layer When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or the hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or the electron transport, or for preventing the overflow of holes.
  • the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or the hole injection rate), thereby enabling the charge balance to be controlled.
  • the electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may block overflowing electrons from the light-emitting layer and confine the excitons in the light-emitting layer to prevent light leakage.
  • the hole transport layer which is further included, may be used as a hole auxiliary layer or an electron blocking layer.
  • the hole auxiliary layer and the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • 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 organic electroluminescent device having two or more light-emitting layers, which emits white light.
  • An organic electroluminescent material according to one embodiment of the present disclosure may be used as light-emitting materials for a white organic light-emitting device.
  • the white organic light-emitting device has been suggested in various structures such as a parallel side-by-side arrangement method, a stacking arrangement method, or CCM (color conversion material) method, etc., according to the arrangement of R (Red), G (Green), B (blue), or YG (yellowish green) light-emitting units.
  • the organic electroluminescent material according to one embodiment of the present disclosure may also be applied to the organic electroluminescent device comprising a QD (quantum dot).
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film-forming methods such as ink jet printing, spin coating, dip coating, flow coating, etc., can be used.
  • a thin film can be formed by dissolving or diffusing the materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent is not specifically limited as long as the material forming each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a film.
  • a display system e.g., a display system for smartphones, tablets, notebooks, PCs, TVs, or cars
  • a lighting system e.g., an outdoor or indoor lighting system
  • An OLED comprising an organic electroluminescent compound according to the present disclosure was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10 ⁇ 6 torr.
  • compound HI-2 was introduced into another cell of the vacuum vapor deposition 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.
  • Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 20 nm on the second hole injection layer.
  • Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 5 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: Compound C-1 was introduced into one cell of the vacuum vapor depositing apparatus as a host of the light-emitting layer, and compound BD was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and the dopant was deposited in a doping amount of 2 wt % based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 20 nm on the second hole transport layer.
  • compound ET-1 and compound EI-1 were evaporated at a rate of 1:1 in two other cells to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
  • an OLED was produced.
  • the minimum time taken to be reduced from 100% to 95% of the luminance at 2,000 nit was 76 hours.
  • An OLED was produced in the same manner as in Device Example 1, except that compound H-1 was used as the host material of the light-emitting layer.
  • the minimum time taken to be reduced from 100% to 95% of the luminance at 2,000 nit was 11 hours.
  • An OLED was produced in the same manner as in Device Example 1, except that compound H-2 was used as the host material of the light-emitting layer.
  • the minimum time taken to be reduced from 100% to 95% of the luminance at 2,000 nit was 25 hours.
  • An OLED was produced in the same manner as in Device Example 1, except that compound H-3 was used as the host material of the light-emitting layer.
  • the minimum time taken to be reduced from 100% to 95% of the luminance at 2,000 nit was 13 hours.
  • an organic electroluminescent device by substituting hydrogens of the host compound of the light-emitting layer with deuterium, it can be seen that the lifespan characteristic is far superior to the organic electroluminescent device using conventional compounds as a host. It is understood that such improvement in lifespan characteristic of an OLED is due to an improvement of stability of the material due to decrease of the zero point vibration energy of the deuterated compound, compared to a compound which is non-deuterated or deuterated with less deuterium.

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)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)
US17/287,951 2018-10-26 2019-10-25 Organic electroluminescent compound and organic electroluminescent device comprising the same Abandoned US20210395215A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
KR10-2018-0129371 2018-10-26
KR20180129371 2018-10-26
KR10-2019-0132727 2019-10-24
KR1020190132727A KR102305649B1 (ko) 2018-10-26 2019-10-24 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
PCT/KR2019/014150 WO2020085845A1 (en) 2018-10-26 2019-10-25 Organic electroluminescent compound and organic electroluminescent device comprising the same

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2019/014150 A-371-Of-International WO2020085845A1 (en) 2018-10-26 2019-10-25 Organic electroluminescent compound and organic electroluminescent device comprising the same

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US18/493,118 Continuation US20240067618A1 (en) 2018-10-26 2023-10-24 Organic electroluminescent compound and organic electroluminescent device comprising the same

Publications (1)

Publication Number Publication Date
US20210395215A1 true US20210395215A1 (en) 2021-12-23

Family

ID=70733210

Family Applications (2)

Application Number Title Priority Date Filing Date
US17/287,951 Abandoned US20210395215A1 (en) 2018-10-26 2019-10-25 Organic electroluminescent compound and organic electroluminescent device comprising the same
US18/493,118 Pending US20240067618A1 (en) 2018-10-26 2023-10-24 Organic electroluminescent compound and organic electroluminescent device comprising the same

Family Applications After (1)

Application Number Title Priority Date Filing Date
US18/493,118 Pending US20240067618A1 (en) 2018-10-26 2023-10-24 Organic electroluminescent compound and organic electroluminescent device comprising the same

Country Status (5)

Country Link
US (2) US20210395215A1 (ko)
JP (2) JP2022504349A (ko)
KR (4) KR102305649B1 (ko)
CN (1) CN112955523A (ko)
DE (1) DE112019004839T5 (ko)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210351358A1 (en) * 2020-04-24 2021-11-11 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent device
US11864461B2 (en) 2018-10-16 2024-01-02 Lg Chem, Ltd. Organic compound and organic light-emitting device comprising same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114287069A (zh) * 2020-06-01 2022-04-05 株式会社Lg化学 组合物、沉积源、包含所述组合物的有机电致发光器件及其制造方法
WO2022144019A1 (zh) * 2021-01-04 2022-07-07 浙江光昊光电科技有限公司 有机混合物及其在有机电子器件的应用
WO2023162701A1 (ja) * 2022-02-25 2023-08-31 日鉄ケミカル＆マテリアル株式会社 有機電界発光素子用材料、及び有機電界発光素子

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018066830A1 (ko) * 2016-10-05 2018-04-12 에스에프씨 주식회사 장수명, 저전압 및 고효율 특성을 갖는 유기 발광 소자

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8759818B2 (en) 2009-02-27 2014-06-24 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
TW201245408A (en) 2011-04-08 2012-11-16 Du Pont Electronic device
JP6317544B2 (ja) * 2013-02-15 2018-04-25 出光興産株式会社 有機エレクトロルミネッセンス素子および電子機器
KR102420202B1 (ko) * 2014-06-27 2022-07-14 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102419711B1 (ko) * 2014-07-09 2022-07-13 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
CN107531661B (zh) * 2015-04-23 2024-05-28 Sfc株式会社 有机发光元件用化合物以及包括该化合物的有机发光元件
KR20180037717A (ko) * 2016-10-05 2018-04-13 에스에프씨 주식회사 장수명, 저전압 및 고효율 특성을 갖는 유기 발광 소자
KR20180050891A (ko) * 2016-11-07 2018-05-16 에스에프씨 주식회사 장수명 특성을 가지는 유기 발광 소자
KR102122212B1 (ko) * 2016-12-29 2020-06-26 에스에프씨주식회사 고효율을 갖는 유기 발광 소자
KR102136806B1 (ko) * 2018-03-28 2020-07-23 엘지디스플레이 주식회사 신규한 유기화합물 및 상기 유기화합물을 포함하는 유기전계 발광소자
WO2019235902A1 (ko) * 2018-06-08 2019-12-12 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기전자소자
KR102091507B1 (ko) * 2018-07-24 2020-03-20 머티어리얼사이언스 주식회사 유기 전계 발광 소자
KR102261230B1 (ko) * 2018-09-21 2021-06-07 주식회사 엘지화학 유기 발광 소자
KR20210075088A (ko) * 2018-10-09 2021-06-22 이데미쓰 고산 가부시키가이샤 신규한 화합물, 유기 일렉트로루미네센스 소자, 전자 기기
US10763444B2 (en) * 2018-10-09 2020-09-01 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and electronic apparatus provided with the same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018066830A1 (ko) * 2016-10-05 2018-04-12 에스에프씨 주식회사 장수명, 저전압 및 고효율 특성을 갖는 유기 발광 소자
US20210296590A1 (en) * 2016-10-05 2021-09-23 Sfc Co., Ltd. Organic light-emitting diode having long lifespan, low voltage, and high efficiency property

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11864461B2 (en) 2018-10-16 2024-01-02 Lg Chem, Ltd. Organic compound and organic light-emitting device comprising same
US20210351358A1 (en) * 2020-04-24 2021-11-11 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent device

Also Published As

Publication number Publication date
JP2024050586A (ja) 2024-04-10
KR20210095108A (ko) 2021-07-30
KR20230164626A (ko) 2023-12-04
US20240067618A1 (en) 2024-02-29
JP2022504349A (ja) 2022-01-13
KR20200047398A (ko) 2020-05-07
CN112955523A (zh) 2021-06-11
KR102305649B9 (ko) 2023-03-17
DE112019004839T5 (de) 2021-06-10
KR20230065223A (ko) 2023-05-11
KR102305649B1 (ko) 2021-09-29

Similar Documents

Publication Publication Date Title
US20220006019A1 (en) A plurality of light-emitting materials and organic electroluminescent device comprising the same
US11788000B2 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20210119134A1 (en) Plurality of light-emitting material and organic electroluminescent device comprising the same
US20240067618A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US11557728B2 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20220255017A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20220162210A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20220037596A1 (en) Plurality of light-emitting materials, organic electroluminescent compound, and organic electroluminescent device comprising the same
US20210210684A1 (en) Plurality of organic electroluminescent materials and organic electroluminescent device comprising the same
KR20210006283A (ko) 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
US20220109110A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20230225197A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
WO2020085845A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20220251051A1 (en) Organic electroluminescent compound and organic electroluminescent device thereof
US20210269405A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
KR20220031241A (ko) 유기 전계 발광 소자
US20230117383A1 (en) Plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same
US20240107794A1 (en) Organic electroluminescent device
US20240237511A1 (en) Plurality of organic electroluminescent materials and organic electroluminescent device comprising the same
US20240114778A1 (en) Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same
KR20230131652A (ko) 유기 전계 발광 소자 및 유기 전계 발광 화합물
US20230320203A1 (en) Plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same
JP2024031874A (ja) 複数のホスト材料、有機エレクトロルミネセント化合物、及びそれを含む有機エレクトロルミネセントデバイス
KR20230112551A (ko) 유계 전계 발광 화합물, 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
KR20220077067A (ko) 유기 전계 발광 화합물, 이를 포함하는 복수 종의 호스트 재료, 및 유기 전계 발광 소자

Legal Events

Date Code Title Description
STPP Information on status: patent application and granting procedure in general

Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION

STPP Information on status: patent application and granting procedure in general

Free format text: NON FINAL ACTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: FINAL REJECTION MAILED

STCB Information on status: application discontinuation

Free format text: EXPRESSLY ABANDONED -- DURING EXAMINATION