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WO2017171420A1 - Composé et élément électroluminescent organique utilisant ce composé - Google Patents

Composé et élément électroluminescent organique utilisant ce composé Download PDF

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WO2017171420A1
WO2017171420A1 PCT/KR2017/003462 KR2017003462W WO2017171420A1 WO 2017171420 A1 WO2017171420 A1 WO 2017171420A1 KR 2017003462 W KR2017003462 W KR 2017003462W WO 2017171420 A1 WO2017171420 A1 WO 2017171420A1
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compound
group
substituted
layer
unsubstituted
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Korean (ko)
Inventor
한미연
이동훈
허정오
장분재
강민영
허동욱
정민우
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LG Chem Ltd
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LG Chem Ltd
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Priority to CN201780021702.XA priority patent/CN108884059B/zh
Publication of WO2017171420A1 publication Critical patent/WO2017171420A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Definitions

  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • At least one of X1 to X3 is N, the rest is CR,
  • R is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,
  • Ar1, Ar2 and -L- (Y) n are different from each other,
  • Ar1 and Ar2 are different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,
  • L is a direct bond; A substituted or unsubstituted monocyclic or polycyclic divalent to hexavalent aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic divalent to hexavalent heteroaryl group having 3 to 20 carbon atoms,
  • Y is a naphthyl group; Phenanthrene group; Dimethyl fluorene group; Anthracene group; Triphenylene group; Pyrene group; Tetracene group; Chrysene group; Perylene group; Or a fluoranthene group,
  • n is an integer of 2-5, and some Y is the same or different.
  • an exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
  • the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
  • the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and transport, luminescence, electron transport, or electron injection materials, preferably as a material of a light emitting layer, an electron transport layer or an electron injection layer. .
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • FIG. 3 is a mass spectrum of Compound 1 according to Preparation Example 1.
  • FIG. 4 is a mass spectrum of Compound 2 according to Preparation Example 2.
  • FIG. 5 is a mass spectrum of Compound 3 according to Preparation Example 3.
  • FIG. 6 is a Mass spectrum of Compound 4 according to Preparation Example 4.
  • FIG. 7 is a Mass spectrum of Compound 5 according to Preparation Example 5.
  • FIG. 8 is a Mass spectrum of Compound 6 according to Preparation Example 6.
  • FIG. 11 is a Mass spectrum of Compound 11 according to Preparation Example 11.
  • FIG. 13 is a Mass spectrum of Compound 13 according to Preparation Example 13.
  • FIG. 14 is a Mass spectrum of Compound 16 according to Preparation 16.
  • FIG. 15 is a Mass spectrum of Compound 17 according to Preparation Example 17.
  • FIG. 15 is a Mass spectrum of Compound 17 according to Preparation Example 17.
  • FIG. 16 is a Mass spectrum of Compound 20 according to Preparation Example 20.
  • FIG. 17 is a Mass spectrum of Compound 22 according to Preparation Example 22.
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • the term "substituted or unsubstituted” is deuterium; Halogen group; Nitrile group; Nitro group; Amino group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted two or more substituents of the substituents exemplified above.
  • the substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the heterocyclic group is a heterocyclic group including one or more of O, N, S, Si, and Se as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group are thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Car
  • the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group.
  • the condensation structure may be a structure in which an aromatic hydrocarbon ring is condensed to a corresponding substituent.
  • a condensed ring of benzimidazole Etc. but is not limited thereto.
  • heteroarylene is a divalent group.
  • X1 is N
  • X2 and X3 are CR.
  • X2 is N
  • X1 and X3 are CR.
  • X1 and X2 are N, and X3 is CR.
  • X2 and X3 are N, and X1 is CR.
  • X1 to X3 are N.
  • R is hydrogen or deuterium
  • R is hydrogen
  • Ar1 and Ar2 are different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms.
  • Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • Ar1 and Ar2 are different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted dimethyl fluorene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthyl group or substituted or unsubstituted pyrene group.
  • Ar1 and Ar2 are different from each other, and each independently a phenyl group; Biphenyl group; Phenanthrene group; Dimethyl fluorene group; Dibenzofuran group; Dibenzothiophene group; Naphthyl group or pyrene group.
  • Ar1 is a phenyl group
  • Ar2 is a biphenyl group
  • Phenanthrene group Dimethyl fluorene group
  • Dibenzofuran group Dibenzothiophene group
  • Naphthyl group or pyrene group is a group that has a phenyl group
  • Ar1 is a phenyl group
  • Ar2 is a biphenyl group
  • Phenanthrene group Dimethyl fluorene group
  • Dibenzofuran group Dibenzothiophene group
  • Naphthyl group or pyrene group Naphthyl group or pyrene group
  • L is a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent heteroaryl group having 3 to 20 carbon atoms.
  • L is a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent aryl group having 6 to 20 carbon atoms.
  • L is a substituted or unsubstituted monocyclic or polycyclic trivalent aryl group having 6 to 20 carbon atoms.
  • L is a divalent to tetravalent phenyl group; Divalent to tetravalent biphenyl groups; Divalent to tetravalent naphthyl groups; Divalent to tetravalent phenanthrene groups; Divalent to tetravalent carbazole groups; Divalent to tetravalent pyridine groups; Divalent to tetravalent pyrimidine groups; Divalent to tetravalent triazine groups; Divalent to tetravalent quinoline groups; Divalent to tetravalent dibenzofuran groups; Or a divalent to tetravalent dibenzothiophene group.
  • L is a substituted or unsubstituted trivalent phenyl group; Substituted or unsubstituted trivalent biphenyl group; Substituted or unsubstituted trivalent phenanthrene group; Substituted or unsubstituted trivalent dimethyl fluorene group; Substituted or unsubstituted trivalent dibenfuran group; Substituted or unsubstituted trivalent dibenzothiophene group; Substituted or unsubstituted trivalent naphthyl group or substituted or unsubstituted trivalent pyrene group.
  • L is a divalent to tetravalent phenyl group; Divalent to tetravalent biphenyl groups; Divalent to tetravalent phenanthrene groups; Divalent to tetravalent dimethylfluorene groups; Divalent to tetravalent dibenfuran groups; Divalent to tetravalent dibenzothiophene groups; Or a divalent to tetravalent naphthyl group or a divalent to tetravalent pyrene group.
  • L is a trivalent phenylene group; Trivalent biphenylylene group; Trivalent phenanthrene group; Trivalent dimethyl fluorene group; Trivalent dibenfuran group; Trivalent dibenzothiophene group; It is a trivalent naphthyl group or a trivalent pyrene group.
  • L is a divalent to tetravalent phenyl group or a divalent to tetravalent biphenyl group.
  • L is a trivalent phenyl group or a trivalent biphenyl group.
  • Y is selected from the following structural formulas.
  • Y is a naphthyl group or a phenanthrene group.
  • the plurality of Y is different.
  • the plurality of Y is the same.
  • the compound of Formula 1 is any one selected from the following structural formulas.
  • the compound according to an exemplary embodiment of the present application may be prepared by the manufacturing method described below.
  • the compound of Formula 1 may have a core structure as shown in Scheme 1 below.
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • a compound of formula A may be obtained by performing a coupling reaction using a triazine compound and a linker of boronic acid or boronate as a catalyst with Pd.
  • the core structure of Formula 1 may be obtained through a coupling reaction between the compound of Formula B and compound Y.
  • the present specification provides an organic light emitting device including the compound described above.
  • the first electrode A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the organic material layer of the organic light emitting device of the present application may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
  • the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
  • the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
  • the organic material layer includes an electron transporting layer, an electron injection layer, or a layer for simultaneously injecting or transporting an electron
  • the electron injection layer, an electron transporting layer, or a layer for simultaneously injecting and transporting an electron is Compound.
  • the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May comprise additional compounds.
  • the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May further comprise an N-type dopant.
  • the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons It may further comprise a silver metal complex.
  • the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons
  • the silver alkali metal complex may further include.
  • the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May further comprise lithium quinolate.
  • the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May include the compound of the present application and lithium quinolate in a weight ratio of 1: 9 to 9: 1.
  • the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May include the compound of the present application and lithium quinolate in a weight ratio of 4: 6 to 6: 4.
  • the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May include the compound of the present application and lithium quinolate in a weight ratio of 1: 1.
  • the organic layer has a thickness of 1 kPa to 1000 kPa, more preferably 1 kPa to 500 kPa.
  • the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound.
  • the organic light emitting device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers comprises the compound.
  • the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound.
  • the compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazolyl group, or benzocarbazolyl group in addition to the organic material layer including the compound.
  • the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of the organic light emitting device according to the exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked.
  • the structure is illustrated.
  • the compound may be included in at least one of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.
  • the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.
  • the organic light emitting device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the compound.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Chemical Formula 1.
  • the organic light emitting device of the present application may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer.
  • the compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic containing compounds include dibenzofuran derivatives, ladder type furan compounds, and pyrides. Midine derivatives and the like, but is not limited thereto.
  • the electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • Compound 3-A was prepared by the same method as Compound 1-A, except that (3-bromo-5-chlorophenyl) boronic acid was used instead of (3,5-dichlorophenyl) boronic acid.
  • Compound 3 was prepared in the same manner as Compound 1, except that Compound 3-B was used instead of Compound 1-B and (4- (1-naphthalenyl) phenyl) boronic acid was used instead of 1-bromonaphthalene.
  • Compound 4 was prepared in the same manner as Compound 3, except that (4- (2-naphthalenyl) phenyl) boronic acid was used instead of (4- (1-naphthalenyl) phenyl) boronic acid.
  • Compound 5-B was prepared by the same method as Compound 3-B, except that 2-naphthalenylboronic acid was used instead of 1-naphthalenylboronic acid.
  • Compound 6 was prepared in the same manner as Compound 5, except that (4- (1-naphthalenyl) phenyl) boronic acid was used instead of (4- (2-naphthalenyl) phenyl) boronic acid.
  • Compound 7 was prepared in the same manner as Compound 1, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.
  • Compound 8-B was prepared by the same method as Compound 1-B, except that Compound 8-A was used instead of Compound 1-A.
  • Compound 8 was prepared in the same manner as Compound 7, except that Compound 8-B was used instead of Compound 1-B.
  • Compound 9 was prepared in the same manner as Compound 8, except that 1-bromonaphthalene was used instead of 9-bromophenanthrene.
  • Compound 10 was prepared in the same manner as Compound 8, except that 2-bromonaphthalene was used instead of 9-bromophenanthrene.
  • Compound 11-B was prepared by the same method as Compound 3-B, except that 11-A was used instead of Compound 3-A.
  • Compound 11 was prepared in the same manner as Compound 3, except that Compound 11-B was used instead of Compound 3-B.
  • Compound 12 was prepared by the same method as Compound 4, except that Compound 11-B was used instead of Compound 3-B.
  • Compound 13-B was prepared by the same method as Compound 5-B, except that Compound 11-A was used instead of Compound 3-A.
  • Compound 13 was prepared by the same method as Compound 5, except that Compound 13-B was used instead of Compound 5-B.
  • Compound 14 was prepared in the same manner as Compound 13, except that (4- (naphthalen-1-yl) phenyl) boronic acid was used instead of (4- (naphthalen-2-yl) phenyl) boronic acid.
  • Compound 16-B was prepared by the same method as Compound 1-B, except that Compound 16-A was used instead of Compound 1-A.
  • Compound 16 was prepared in the same manner as Compound 1, except that Compound 16-B was used instead of Compound 1-B.
  • Compound 17 was prepared in the same manner as Compound 1, except for using Compound 16-B instead of Compound 1-B and using 2-bromonaphthalene instead of 1-bromonaphthalene.
  • Compound 18-B was prepared by the same method as Compound 3-B, except that Compound 18-A was used instead of Compound 3-A.
  • Compound 18 was prepared in the same manner as Compound 3, except that Compound 18-B was used instead of Compound 3-B.
  • Compound 19 was prepared by the same method as Compound 4, except that Compound 18-B was used instead of Compound 3-B.
  • Compound 20-B was prepared by the same method as Compound 18-B, except that 2-naphthalene boronic acid was used instead of 1-naphthalene boronic acid.
  • Compound 20 was prepared in the same manner as Compound 5, except that Compound 20-B was used instead of Compound 5-B.
  • Compound 21 was prepared by the same method as Compound 20, except that (4- (naphthalen-1-yl) phenyl) boronic acid was used instead of (4- (naphthalen-2-yl) phenyl) boronic acid.
  • Compound 22 was prepared in the same manner as Compound 16, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.
  • Compound 23-A was prepared by the same method as Compound 1-A, except that (2,5-dichlorophenyl) boronic acid was used instead of (3,5-dichlorophenyl) boronic acid.
  • Compound 23-B was prepared by the same method as Compound 1-B, except that Compound 23-A was used instead of Compound 1-A.
  • Compound 23 was prepared by the same method as Compound 1, except that Compound 23-B was used instead of Compound 1-B.
  • Compound 24 was prepared in the same manner as Compound 23, except that 2-bromonaphthalene was used instead of 1-bromonaphthalene.
  • Compound 25 was prepared in the same manner as Compound 23, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.
  • Compound 26-B was prepared by the same method as Compound 3-B, except that Compound 26-A was used instead of Compound 3-A.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the following compound [HI-A] was thermally vacuum deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • Hexanitrile hexaazatriphenylene (HAT) of the following formula on the hole injection layer 50 ⁇ and the following compound [HT-A] (600 ⁇ ) was sequentially vacuum-deposited to form a hole transport layer.
  • the following compounds [BH] and [BD] were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to have a film thickness of 200 Pa to form a light emitting layer.
  • Compound 1 and [LiQ] (Lithiumquinolate) were vacuum-deposited at a weight ratio of 1: 1 on the emission layer to form an electron injection and transport layer at a thickness of 350 kHz.
  • lithium fluoride (LiF) and aluminum were deposited to a thickness of 1,000 ⁇ in order to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.9 ⁇ / sec
  • the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 ⁇ / sec
  • aluminum 2 ⁇ / sec the vacuum degree during deposition was 1 ⁇ 10 -7 to 5 ⁇ 10 - to maintain the 8 torr, it was produced in the organic light emitting device.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 12 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 13 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 14 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 17 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 18 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 19 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 20 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 21 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 22 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 23 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 24 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 25 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 26 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET1 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET2 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET3 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET4 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET5 was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET6 was used instead of Compound 1 in Example 1.
  • the organic light emitting diodes of Examples 1 to 14, 16 to 26 and Comparative Examples 1 to 6 measured driving voltage and luminous efficiency at a current density of 10 mA / cm 2 , and compared to initial luminance at a current density of 20 mA / cm 2 .
  • the time to become% (LT90) was measured. The results are shown in Table 1 below.
  • Example 10 mA / cm 2 compound Voltage (V) Current efficiency (cd / A) Color coordinates (x, y) Life Time (T90 at 20mA / cm 2 )
  • Example 1 One 3.68 5.29 (0.142, 0.096) 127
  • Example 2 3.68 5.41 (0.142, 0.096) 116
  • Example 3 3 3.73 5.15 (0.142, 0.096) 180
  • Example 4 4. 3.72 5.23 (0.142, 0.097) 167
  • Example 5 5 3.72 5.26 (0.142, 0.096) 159
  • Example 6 6 3.81 5.21 (0.142, 0.097) 131
  • Example 7 7. 3.80 5.12 (0.142, 0.096) 142
  • Example 8 8 3.75 5.35 (0.142, 0.096) 108
  • Example 9 9 3.63 5.42 (0.142, 0.096) 103
  • Example 10 10 3.63 5.48 (0.142, 0.096) 101
  • Example 11 11 3.68 5.37 (0.142, 0.095) 150

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Abstract

La présente invention concerne un composé de formule chimique (1), et un élément électroluminescent organique le comprenant.
PCT/KR2017/003462 2016-03-30 2017-03-30 Composé et élément électroluminescent organique utilisant ce composé Ceased WO2017171420A1 (fr)

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JP2019167311A (ja) * 2018-03-23 2019-10-03 株式会社Ｋｙｕｌｕｘ 有機発光素子材料合成用原料および化合物
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CN115141216B (zh) * 2022-07-25 2024-03-12 宇瑞(上海)化学有限公司 一种含嗪类化合物及其有机发光器件
WO2025057775A1 (fr) * 2023-09-15 2025-03-20 東ソー株式会社 Matériau destiné à un élément de conversion photoélectrique pour élément d'imagerie, et élément d'imagerie

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20090079134A (ko) * 2008-01-16 2009-07-21 주식회사 엘지화학 새로운 이미다졸 유도체 및 이를 이용한 유기전자소자
KR20130066554A (ko) * 2011-12-12 2013-06-20 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20150030294A (ko) * 2013-09-11 2015-03-20 주식회사 알파켐 신규한 전자 수송 물질 및 이를 이용한 유기 발광 소자
KR20160025776A (ko) * 2014-08-28 2016-03-09 (주)더블유에스 피리딜기가 결합된 트리아진 유도체 및 이를 포함한 유기 전계발광 소자
KR20170023328A (ko) * 2015-08-21 2017-03-03 엘지디스플레이 주식회사 유기전계발광소자

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8187727B2 (en) * 2005-07-22 2012-05-29 Lg Chem, Ltd. Imidazole derivatives, preparation method thereof and organic electronic device using the same
US8053762B2 (en) * 2005-12-13 2011-11-08 Lg Chem, Ltd. Imidazoquinazoline derivative, process for preparing the same, and organic electronic device using the same
US8367219B2 (en) * 2007-10-30 2013-02-05 Samsung Electronics Co., Ltd. Anthracene-based compound and organic light emitting device employing the same
KR101317531B1 (ko) * 2008-01-16 2013-10-15 주식회사 엘지화학 신규한 이미다졸 유도체 및 이를 이용한 유기전자소자
KR101058103B1 (ko) * 2008-04-15 2011-08-24 삼성모바일디스플레이주식회사 바이피리딘계 화합물 및 이를 포함한 유기막을 구비한 유기발광 소자
CN101570536B (zh) * 2008-04-28 2014-08-20 三星显示有限公司 基于蒽的化合物和使用其的有机发光器件
KR101460365B1 (ko) * 2008-04-29 2014-11-10 주식회사 엘지화학 신규한 이미다졸 유도체 및 이를 이용한 유기전자소자
EP2336130B1 (fr) * 2008-09-24 2017-06-28 Hodogaya Chemical Co., Ltd. Composé contenant une structure de cycle anthracène substitué et une structure de cycle pyridoindole et dispositif organique électroluminescent
EP2327679B1 (fr) * 2008-09-24 2017-03-01 LG Chem, Ltd. Nouveaux derives d'anthracene et dispositif electronique organique les utilisant
CN103333167B (zh) * 2008-11-03 2016-08-24 株式会社Lg化学 新的含氮杂环化合物及使用该化合物的有机电子器件
KR101567610B1 (ko) * 2010-11-04 2015-11-09 주식회사 엘지화학 신규한 질소 함유 헤테로환 화합물 및 이를 이용한 유기 전자 소자
TWI504722B (zh) * 2010-12-03 2015-10-21 Jnc Corp 具有含吡啶取代基的苯并［ｃ］咔唑化合物及有機電激發光元件
KR20130118269A (ko) * 2012-04-19 2013-10-29 에스에프씨 주식회사 방향족 화합물 및 이를 포함하는 유기전계발광소자
KR101511954B1 (ko) * 2013-04-29 2015-04-16 주식회사 알파켐 신규한 전자 수송 물질 및 이를 이용한 유기 발광 소자
KR102191996B1 (ko) * 2013-09-27 2020-12-17 삼성디스플레이 주식회사 헤테로고리 화합물 및 이를 포함한 유기 발광 소자
WO2015099508A1 (fr) * 2013-12-27 2015-07-02 희성소재(주) Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé
KR102479149B1 (ko) * 2014-07-21 2022-12-19 메르크 파텐트 게엠베하 전자 소자용 재료
WO2016186321A1 (fr) * 2015-05-19 2016-11-24 Rohm And Haas Electronic Materials Korea Ltd. Matériau hôte phosphoré et dispositif électroluminescent organique le comprenant
KR20160136211A (ko) * 2015-05-19 2016-11-29 롬엔드하스전자재료코리아유한회사 인광 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
EP3307190B1 (fr) * 2015-06-11 2023-05-17 Intuitive Surgical Operations, Inc. Systèmes et procédés de mise en prise d'instrument
WO2017069428A1 (fr) * 2015-10-22 2017-04-27 Rohm And Haas Electronic Materials Korea Ltd. Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
KR102458043B1 (ko) * 2015-11-25 2022-10-24 엘지디스플레이 주식회사 유기전계발광소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20090079134A (ko) * 2008-01-16 2009-07-21 주식회사 엘지화학 새로운 이미다졸 유도체 및 이를 이용한 유기전자소자
KR20130066554A (ko) * 2011-12-12 2013-06-20 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20150030294A (ko) * 2013-09-11 2015-03-20 주식회사 알파켐 신규한 전자 수송 물질 및 이를 이용한 유기 발광 소자
KR20160025776A (ko) * 2014-08-28 2016-03-09 (주)더블유에스 피리딜기가 결합된 트리아진 유도체 및 이를 포함한 유기 전계발광 소자
KR20170023328A (ko) * 2015-08-21 2017-03-03 엘지디스플레이 주식회사 유기전계발광소자

Cited By (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019527472A (ja) * 2016-06-29 2019-09-26 サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. 有機光電子素子用化合物、有機光電子素子用組成物、有機光電子素子および表示装置
US11706975B2 (en) 2016-06-29 2023-07-18 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus
US11678572B2 (en) 2016-06-29 2023-06-13 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus
US11084806B2 (en) 2016-07-12 2021-08-10 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device
US11264574B2 (en) 2016-07-29 2022-03-01 Samsung Sdi Co., Ltd. Composition for organic optoelectronic element, organic optoelectronic element, and display device
US11158817B2 (en) 2017-01-05 2021-10-26 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
US12225814B2 (en) 2017-12-29 2025-02-11 Samsung Sdi Co., Ltd. Compound for organic optoelectronic diode, composition for organic optoelectronic diode, organic optoelectronic diode and display device
TWI702214B (zh) * 2017-12-29 2020-08-21 南韓商三星Ｓｄｉ股份有限公司 用於有機光電裝置的化合物、用於有機光電裝置的組成物、有機光電裝置以及顯示裝置
CN111032645B (zh) * 2018-01-22 2023-03-10 株式会社Lg化学 多环化合物及包含其的有机发光器件
CN111032645A (zh) * 2018-01-22 2020-04-17 株式会社Lg化学 多环化合物及包含其的有机发光器件
EP3527558A1 (fr) * 2018-02-16 2019-08-21 Novaled GmbH Composés n-hétéroarylène
JP7112715B2 (ja) 2018-03-23 2022-08-04 株式会社Kyulux 有機発光素子材料合成用原料および化合物
JP2019167311A (ja) * 2018-03-23 2019-10-03 株式会社Ｋｙｕｌｕｘ 有機発光素子材料合成用原料および化合物
KR102218664B1 (ko) 2018-05-08 2021-02-22 서울대학교산학협력단 축합환 화합물 및 이를 포함하는 유기 발광 소자
KR20190128554A (ko) * 2018-05-08 2019-11-18 서울대학교산학협력단 축합환 화합물 및 이를 포함하는 유기 발광 소자
US12302751B2 (en) * 2018-06-12 2025-05-13 Samsung Sdi Co., Ltd. Composition for organic optoelectronic device, organic optoelectronic device, and display device
US20210273176A1 (en) * 2018-06-12 2021-09-02 Samsung Sdi Co., Ltd. Composition for organic optoelectronic device, organic optoelectronic device, and display device
EP3617202A1 (fr) * 2018-08-27 2020-03-04 Samsung Electronics Co., Ltd. Composé hétérocyclique et dispositif électroluminescent organique
JP2020033342A (ja) * 2018-08-27 2020-03-05 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． ヘテロ環式化合物及びそれを含む有機発光素子
CN110862378A (zh) * 2018-08-27 2020-03-06 三星电子株式会社 杂环化合物和有机发光器件
CN110862378B (zh) * 2018-08-27 2024-11-15 三星电子株式会社 杂环化合物和有机发光器件
US11393983B2 (en) * 2018-10-23 2022-07-19 E-Ray Optoelectronics Technology Co., Ltd. Phenyl biphenylpyrimidine compound and an organic electroluminescent device using the same
CN111087349A (zh) * 2018-10-23 2020-05-01 昱镭光电科技股份有限公司 苯基联苯嘧啶类化合物及其有机电致发光器件
TWI692471B (zh) * 2018-10-23 2020-05-01 昱鐳光電科技股份有限公司 苯基聯苯嘧啶類化合物及其有機電激發光元件
US20220020932A1 (en) * 2018-11-15 2022-01-20 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US12419191B2 (en) * 2018-11-15 2025-09-16 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN113166098A (zh) * 2018-11-30 2021-07-23 东曹株式会社 三嗪化合物、有机电致发光元件用材料和有机电致发光元件
KR102469873B1 (ko) * 2018-12-07 2022-11-23 주식회사 엘지화학 유기 발광 소자
KR20200070141A (ko) * 2018-12-07 2020-06-17 주식회사 엘지화학 유기 발광 소자
WO2020122460A1 (fr) * 2018-12-12 2020-06-18 삼성에스디아이 주식회사 Composition pour diode optoélectronique organique, diode optoélectronique organique et dispositif d'affichage
KR102756612B1 (ko) * 2020-04-29 2025-01-16 주식회사 엘지화학 유기 발광 소자
KR20210133696A (ko) * 2020-04-29 2021-11-08 주식회사 엘지화학 유기 발광 소자
US12245505B2 (en) 2020-10-26 2025-03-04 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US12268090B2 (en) 2020-10-26 2025-04-01 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US11963445B2 (en) 2020-10-26 2024-04-16 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US11985894B2 (en) 2020-10-26 2024-05-14 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US11991929B2 (en) 2020-10-26 2024-05-21 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US12329029B2 (en) 2020-10-26 2025-06-10 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US12317748B2 (en) 2020-10-26 2025-05-27 Duk San Neolux Co., Ltd. Organic electronic element comprising compound for organic electronic element and an electronic device thereof
US12102004B2 (en) 2020-10-26 2024-09-24 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US11785847B2 (en) 2020-10-26 2023-10-10 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US11917914B1 (en) 2020-10-26 2024-02-27 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US11800800B1 (en) 2020-10-26 2023-10-24 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US11678577B2 (en) 2020-10-26 2023-06-13 Duk San Neolux Co., Ltd. Organic electronic element comprising compound for organic electronic element and an electronic device thereof
US12262637B2 (en) 2020-10-26 2025-03-25 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US11925116B2 (en) 2020-10-26 2024-03-05 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US12295263B2 (en) 2020-10-26 2025-05-06 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
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WO2024121043A1 (fr) * 2022-12-06 2024-06-13 Novaled Gmbh Diode électroluminescente organique, dispositif la comprenant et composé destiné à être utilisé dans celle-ci
EP4383987A1 (fr) * 2022-12-06 2024-06-12 Novaled GmbH Diode électroluminescente organique, dispositif comprenant celle-ci et composé à utiliser dans celle-ci

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