WO2017142304A1 - Composé hétérocyclique et dispositif électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique le comprenant Download PDF

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WO2017142304A1
WO2017142304A1 PCT/KR2017/001649 KR2017001649W WO2017142304A1 WO 2017142304 A1 WO2017142304 A1 WO 2017142304A1 KR 2017001649 W KR2017001649 W KR 2017001649W WO 2017142304 A1 WO2017142304 A1 WO 2017142304A1
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substituted
unsubstituted
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heterocyclic
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김민준
박태윤
최민우
이정하
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LG Chem Ltd
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    • 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
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • 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
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    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
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    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
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    • 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
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    • 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
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    • 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
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
    • 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

Definitions

  • the present specification relates to a heterocyclic compound and an organic electroluminescent device including the same.
  • the electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • the material of the organic thin film may have a light emitting function as necessary.
  • a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used.
  • a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
  • the present specification provides a heterocyclic compound and an organic electroluminescent device including the same.
  • the present application provides a heterocyclic compound represented by the following formula (1).
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a and c are integers of 0 to 3
  • b is an integer of 0 to 4
  • the substituents in parentheses are the same or different.
  • the present application is a 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 aforementioned heterocyclic compound. do.
  • the heterocyclic compound according to the exemplary embodiment of the present application may be used in an organic electroluminescent device to lower the driving voltage of the organic electroluminescent device, improve light efficiency, and improve the lifetime characteristics of the device by thermal stability of the compound. .
  • FIG. 1 illustrates an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
  • FIG. 2 illustrates an organic electroluminescent 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. An example is shown.
  • the present specification provides a heterocyclic compound represented by Chemical Formula 1.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • the term "substituted or unsubstituted” is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Phosphine oxide groups; Silyl groups; An alkyl group; Cycloalkyl group; Alkenyl groups; An alkoxy group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents.
  • "a 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.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50.
  • Specific 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-o
  • the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Do not.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like. It is not limited.
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40.
  • 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 aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but preferably 6 to 25 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, Si, and S, and the like. have.
  • carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60.
  • heterocyclic group examples include thiophenyl group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl Groups, acridil groups, hydroacridyl groups (e.g., ), Pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, and isoquinolinyl , Indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group
  • the condensation structure may be a structure in which an aromatic carbon hydrogen ring is condensed to a corresponding substituent.
  • a condensed ring of benzimidazole Etc. but is not limited thereto.
  • the arylene group refers to a divalent group having two bonding positions in the aryl group.
  • the description of the aforementioned aryl group can be applied except that they are each divalent.
  • adjacent group may mean a substituent substituted on an atom directly connected to an atom in which the corresponding substituent is substituted or another substituent substituted on an atom in which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dimethyl fluorene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; Terphenyl group unsubstituted or substituted with an aryl group; Triphenylene group unsubstituted or substituted with an aryl group; Dimethyl fluorene group unsubstituted or substituted with an aryl group; Dibenzofuran group unsubstituted or substituted with an aryl group; Dibenzothiophene group unsubstituted or substituted with an aryl group; Or a carbazole group unsubstituted or substituted with an aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; Terphenyl group unsubstituted or substituted with a phenyl group; Triphenylene group unsubstituted or substituted with a phenyl group; Dimethyl fluorene group unsubstituted or substituted with a phenyl group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Terphenyl group; Triphenylene group; Dimethyl fluorene group unsubstituted or substituted with a phenyl group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.
  • L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.
  • L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
  • L1 is a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted divalent dibenzofuranyl group; A substituted or unsubstituted divalent dibenzothiophenyl group; Or a substituted or unsubstituted divalent fluorenyl group.
  • L1 is a direct bond; A phenylene group unsubstituted or substituted with an alkyl group; Divalent dibenzofuranyl group unsubstituted or substituted with an alkyl group; Divalent dibenzothiophenyl group unsubstituted or substituted with an alkyl group; Or a divalent fluorenyl group unsubstituted or substituted with an alkyl group.
  • L1 is a direct bond; Phenylene group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; Divalent fluorenyl group; It is a bivalent dimethyl fluorenyl group.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond or a substituted or unsubstituted arylene group.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond or a phenylene group.
  • R1 to R3 are the same as or different from each other, and each independently hydrogen; Or deuterium.
  • R1 to R3 are hydrogen.
  • the heterocyclic compound represented by Formula 1 is any one selected from the following structural formulas.
  • the present specification provides an organic electroluminescent device comprising 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 heterocyclic compound.
  • the organic material layer of the organic electroluminescent 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 EL 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 electroluminescent device is not limited thereto and may include a smaller number of organic layers.
  • the thickness of the organic material layer is 1 kPa to 1000 kPa.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic 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 heterocyclic 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 heterocyclic compound.
  • 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 heterocyclic compound.
  • the organic material layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound.
  • the organic electroluminescent 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 includes the heterocyclic 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 heterocyclic compound.
  • the heterocyclic 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.
  • heterocyclic compound when included in each of the two or more electron transport layers, other materials except for the heterocyclic compound may be the same or different from each other.
  • the organic layer further includes a hole injection layer or a hole transport layer including a heterocyclic compound including an arylamino group, carbazolyl group or benzocarbazolyl group in addition to the organic layer including the heterocyclic compound.
  • the organic electroluminescent device may be an organic electroluminescent device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic electroluminescent device may be an organic electroluminescent device of 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 For example, the structure of an organic EL device according to one embodiment of the present application is illustrated in FIGS. 1 and 2.
  • the heterocyclic compound may be included in the light emitting layer (3).
  • FIG. 2 illustrates an organic electroluminescent 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 of is illustrated.
  • the heterocyclic compound may be included in one or more layers of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.
  • the heterocyclic compound may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.
  • the organic electroluminescent 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 heterocyclic compound.
  • the organic material layers may be formed of the same material or different materials.
  • the organic electroluminescent 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 heterocyclic compound, that is, the heterocyclic compound represented by Formula 1 above. .
  • the organic EL 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 EL 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 EL 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 electroluminescent device may be fabricated 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.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include compounds, dibenzofuran derivatives and ladder type furan compounds. , Pyrimidine 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 to transport 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 electroluminescent device may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.
  • 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 hexanitrile hexaazatriphenylene (HAT-CN) of the following formula was thermally vacuum deposited to a thickness of 150 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • Compound HT (1150 kV) which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer.
  • the following compound EB was vacuum deposited on the hole transport layer with a film thickness of 150 GPa to form an electron blocking layer.
  • BH and BD as described below were vacuum-deposited at a weight ratio of 25: 1 on the electron blocking layer to form a light emitting layer.
  • Compound ET and the compound LiQ were vacuum-deposited on the emission layer in a weight ratio of 1: 1 to form an electron injection and transport layer with a thickness of 360 Pa.
  • lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order to form a cathode.
  • the lithium fluoride of the cathode was 0.3 ⁇ / sec
  • aluminum is deposited at a rate of 2 ⁇ / sec
  • a vacuum 2 ⁇ 10 - The organic electroluminescent element was produced, maintaining 7-5 * 10 ⁇ -6> torr.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 1 was used instead of Compound EB in the Comparative Example.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 2 was used instead of Compound EB in the Comparative Example.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 3 was used instead of Compound EB in the Comparative Example.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 4 was used instead of Compound EB in the Comparative Example.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 5 was used instead of Compound EB in the Comparative Example.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 6 was used instead of Compound EB in the Comparative Example.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 7 was used instead of Compound EB in the Comparative Example.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that Compound 8 was used instead of Compound EB in the Comparative Example.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that the compound of H-1 was used instead of the compound EB in the comparative example.
  • An organic light emitting diode was manufactured according to the same method as the comparative example except for using the compound of H-2 instead of compound EB in the comparative example.
  • An organic electroluminescent device was manufactured according to the same method as the comparative example except for using the compound of H-3 instead of the compound EB in the comparative example.
  • An organic light emitting device was manufactured according to the same method as the comparative example except for using the compound of H-4 instead of compound EB in the comparative example.
  • An organic light emitting diode was manufactured according to the same method as the comparative example except for using the compound of H-5 instead of the compound EB in the comparative example.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that the compound of H-6 was used instead of the compound EB in the comparative example.
  • T95 means the time taken for the luminance to decrease to 95% from the initial luminance (650 nits).
  • the organic electroluminescent device manufactured by using the compound of the present invention as an electron blocking layer exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic electroluminescent device.
  • the core of the present invention exhibits lower voltage, higher efficiency and longer life than organic electroluminescent devices manufactured using the compounds of Comparative Examples 1 to 6 as the electron blocking layer. Voltage is reduced by 5-10% and efficiency is increased by more than 10%.
  • the amines connected to the 2, 10 and 11 of the existing indolo [3,2,1-jk] carbazole are connected in the steric hindrance direction (No. 4) like the compound of the present invention and the conjugation is broken. It showed that the stability of the core indolo [3,2,1-jk] carbazole itself was increased by showing the efficiency increase, the voltage decrease and the long life when connected in the losing direction. In addition, since the portion where the core and the amine are connected to each other is bent, it has excellent advantages in thermal stability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention porte sur un composé hétérocyclique et sur un dispositif électroluminescent organique comprenant ce dernier.
PCT/KR2017/001649 2016-02-15 2017-02-15 Composé hétérocyclique et dispositif électroluminescent organique le comprenant Ceased WO2017142304A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019070083A1 (fr) * 2017-10-06 2019-04-11 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
WO2020220397A1 (fr) * 2019-04-29 2020-11-05 武汉华星光电半导体显示技术有限公司 Matériau électroluminescent, procédé de fabrication de matériau électroluminescent et dispositif électroluminescent
US11594685B2 (en) 2017-03-30 2023-02-28 Lg Chem, Ltd. Organic light emitting device
US11608327B2 (en) 2016-03-03 2023-03-21 Merck Patent Gmbh Materials for organic electroluminescent devices
EP4647476A1 (fr) * 2024-05-09 2025-11-12 Canon Kabushiki Kaisha Composé organique et élément électroluminescent organique

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6705586B2 (ja) * 2016-02-15 2020-06-03 エルジー・ケム・リミテッド ヘテロ環化合物およびこれを含む有機電界発光素子
KR20200090091A (ko) * 2019-01-18 2020-07-28 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102260561B1 (ko) * 2021-01-14 2021-06-04 주식회사 이엘엠 유기 전기 발광 소자의 캐핑층용 조성물 및 이를 포함하는 유기 전기 발광 소자

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013147481A (ja) * 2012-01-23 2013-08-01 Udc Ireland Ltd 合成法、その合成法を用いて合成された化合物および有機電界発光素子
KR20150002219A (ko) * 2013-06-28 2015-01-07 주식회사 이엘엠 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
KR20150073073A (ko) * 2013-12-20 2015-06-30 삼성디스플레이 주식회사 유기 일렉트로루미네센스 소자용 재료 및 이를 포함하는 유기 일렉트로루미네센스 소자
KR20150114905A (ko) * 2014-04-02 2015-10-13 유니버셜 디스플레이 코포레이션 유기 전계발광 물질 및 소자
KR20150131564A (ko) * 2014-05-15 2015-11-25 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102010005697A1 (de) * 2010-01-25 2011-07-28 Merck Patent GmbH, 64293 Verbindungen für elektronische Vorrichtungen
KR20130136359A (ko) * 2012-06-04 2013-12-12 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR102108096B1 (ko) * 2013-12-13 2020-05-07 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
JP2015122369A (ja) * 2013-12-20 2015-07-02 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
JP2015122356A (ja) * 2013-12-20 2015-07-02 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
JP2015122371A (ja) * 2013-12-20 2015-07-02 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
JP6705586B2 (ja) * 2016-02-15 2020-06-03 エルジー・ケム・リミテッド ヘテロ環化合物およびこれを含む有機電界発光素子

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013147481A (ja) * 2012-01-23 2013-08-01 Udc Ireland Ltd 合成法、その合成法を用いて合成された化合物および有機電界発光素子
KR20150002219A (ko) * 2013-06-28 2015-01-07 주식회사 이엘엠 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
KR20150073073A (ko) * 2013-12-20 2015-06-30 삼성디스플레이 주식회사 유기 일렉트로루미네센스 소자용 재료 및 이를 포함하는 유기 일렉트로루미네센스 소자
KR20150114905A (ko) * 2014-04-02 2015-10-13 유니버셜 디스플레이 코포레이션 유기 전계발광 물질 및 소자
KR20150131564A (ko) * 2014-05-15 2015-11-25 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11608327B2 (en) 2016-03-03 2023-03-21 Merck Patent Gmbh Materials for organic electroluminescent devices
US12065431B2 (en) 2016-03-03 2024-08-20 Merck Patent Gmbh Materials for organic electroluminescent devices
US12441715B2 (en) 2016-03-03 2025-10-14 Merck Patent Gmbh Materials for organic electroluminescent devices
US12583842B2 (en) 2016-03-03 2026-03-24 Merck Patent Gmbh Materials for organic electroluminescent devices
US11594685B2 (en) 2017-03-30 2023-02-28 Lg Chem, Ltd. Organic light emitting device
WO2019070083A1 (fr) * 2017-10-06 2019-04-11 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
WO2020220397A1 (fr) * 2019-04-29 2020-11-05 武汉华星光电半导体显示技术有限公司 Matériau électroluminescent, procédé de fabrication de matériau électroluminescent et dispositif électroluminescent
US11407939B2 (en) 2019-04-29 2022-08-09 Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. Electroluminesecent material, method for manufacturing same, and luminesecent device
EP4647476A1 (fr) * 2024-05-09 2025-11-12 Canon Kabushiki Kaisha Composé organique et élément électroluminescent organique

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KR20170095754A (ko) 2017-08-23
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CN108699071A (zh) 2018-10-23
JP2019507739A (ja) 2019-03-22

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