WO2020101439A1 - Nouveau composé et diode électroluminescente organique le comprenant - Google Patents

Nouveau composé et diode électroluminescente organique le comprenant Download PDF

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WO2020101439A1
WO2020101439A1 PCT/KR2019/015682 KR2019015682W WO2020101439A1 WO 2020101439 A1 WO2020101439 A1 WO 2020101439A1 KR 2019015682 W KR2019015682 W KR 2019015682W WO 2020101439 A1 WO2020101439 A1 WO 2020101439A1
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group
layer
compound
light emitting
organic
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황성현
이동훈
장분재
정민우
이정하
한수진
박슬찬
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LG Chem Ltd
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Priority claimed from KR1020190146190A external-priority patent/KR102336599B1/ko
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Priority to CN201980019040.1A priority patent/CN111868053B/zh
Publication of WO2020101439A1 publication Critical patent/WO2020101439A1/fr
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • 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 invention relates to a novel compound and an organic light emitting device comprising the same.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
  • the organic material layer is often formed of a multi-layered structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel organic light emitting material and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by Formula 1:
  • n and n are each independently 0 or 1, provided that at least one of m and n is 1,
  • X is O or S
  • L is a single bond; Substituted or unsubstituted C 6-60 arylene; Or C 2-60 heteroarylene containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • A is any one selected from the group consisting of,
  • Y 1 to Y 3 are each independently N or CH, and at least two of Y 1 to Y 3 are N,
  • Ar 1 to Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and provides an organic light emitting device. .
  • the compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and / or life characteristics in the organic light emitting device.
  • the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 is composed of 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), an electron injection layer (8) and a cathode (4) An example of an organic light emitting device is shown.
  • FIG. 3 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (9), light emitting layer (3), hole blocking layer (10), electron transport layer (7) ,
  • An example of an organic light emitting device including an electron injection layer 8 and a cathode 4 is shown.
  • the present invention provides a compound represented by Formula 1 above.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more
  • the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the oxygen of the ester group may be substituted with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
  • the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be straight chain or branched chain, and 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 a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. 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, styrenyl 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 an exemplary 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 is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto.
  • 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 two substituents may combine with each other to form a spiro structure.
  • the fluorenyl group When the fluorenyl group is substituted, It can be back. However, it is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine 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 , Carbazo
  • an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the exemplified aryl group described above.
  • the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described example of the alkyl group.
  • heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the alkenyl group is the same as the exemplified alkenyl group.
  • the description of the aryl group described above may be applied, except that the arylene is a divalent group.
  • the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding.
  • the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.
  • the compound may be represented by the following Formula 1-1 or Formula 1-2:
  • L is a single bond; Substituted or unsubstituted C 6-20 arylene; Or C 6-20 heteroarylene containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • L may be a single bond or phenylene.
  • Ar 1 to Ar 4 are each independently, substituted or unsubstituted C 6-20 aryl; Or C 6-20 heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • Ar 1 to Ar 4 may each independently be phenyl, biphenylyl, dibenzofuranyl, dibenzothiophenyl, phenyl carbazolyl, or carbazolyl phenyl.
  • At least one of Ar 1 and Ar 2 may be substituted or unsubstituted C 6-60 aryl,
  • At least one of Ar 1 and Ar 2 may be substituted or unsubstituted C 6-20 aryl,
  • At least one of Ar 1 and Ar 2 may be phenyl.
  • X, L, A, m and n are as defined in Formula 1 above, Y 1 and Y 2 are halogen, preferably Y 1 and Y 2 are chloro or bromo.
  • Reaction Schemes 1 and 2 are Suzuki coupling reactions, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • the present invention provides an organic light emitting device comprising the compound represented by the formula (1).
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and an organic light emitting device is provided. do.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention 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 as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto, and may include fewer organic layers.
  • the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the compound according to the present invention can be used as a host for a light emitting layer.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by Chemical Formula 1.
  • the electron transport layer, the electron injection layer, or a layer that simultaneously performs electron transport and electron injection includes a compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer and an electron transport layer
  • the electron transport layer may include a compound represented by Chemical Formula 1.
  • the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of the organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Chemical Formula 1 may be included in the light emitting layer.
  • the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
  • FIG. 3 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (9), light emitting layer (3), hole blocking layer (10), electron transport layer (7) ,
  • An example of an organic light emitting device including an electron injection layer 8 and a cathode 4 is shown.
  • the compound represented by Formula 1 may be included in one or more of the hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer and electron transport layer.
  • the organic light-emitting device according to the present invention can be made of materials and methods known in the art, except that at least one layer of the organic material layer contains the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon.
  • an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 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
  • the second electrode is an anode
  • the positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth.
  • the positive electrode material 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), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material is preferably 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;
  • There is a multilayer structure material such as LiF / Al or LiO 2 / Al, but is not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, 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 the light emitting layer.
  • a compound that prevents migration of the excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferred.
  • the high 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 layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based , Organic 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 from the hole injection layer to the light emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from being recombined in the light emitting layer and passing into the hole transport layer, and is also called an electron suppression layer.
  • the electron blocking layer is preferably a material having a smaller electron affinity than the electron transport layer.
  • a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively is preferably a material having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • the light emitting layer may include a host material and a dopant material.
  • the host material may be a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the compound represented by Chemical Formula 1 may be included as a host material.
  • the dopant material examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound.
  • a compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted.
  • a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like but are not limited thereto.
  • examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.
  • the hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent the holes injected from the anode from being recombined in the light emitting layer and passing into the electron transport layer, and is also referred to as a hole suppressing layer.
  • the hole blocking layer is preferably a material having a large ionization energy.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include the Al complex 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 according to the prior art.
  • suitable cathode materials are those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
  • the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • ITO Indium Tin Oxide
  • distilled water filtered secondarily as a filter of Millipore Co.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner.
  • the substrate was transferred to a vacuum evaporator.
  • the following compound HT-A and the following compound PD were thermally vacuum-deposited to a thickness of 100 ⁇ at a weight ratio of 95: 5, and then only the following compound HT-A was deposited to a thickness of 1150 ⁇ to form a hole transport layer. Formed.
  • the following compound HT-B was thermally vacuum-deposited to a thickness of 450 MPa to form an electron blocking layer.
  • Compound 1 and the following compound GD prepared above were vacuum deposited at a weight ratio of 85:15 to a thickness of 400 Pa to form a light emitting layer.
  • the following compound ET-A was vacuum-deposited to a thickness of 50 ⁇ to form a hole blocking layer.
  • the following compound ET-B and the following compound Liq were thermally vacuum-deposited to a thickness of 250 ⁇ at a weight ratio of 2: 1, and then vacuum-deposited to a thickness of 30 ⁇ at LiF and magnesium at a weight ratio of 1: 1.
  • an electron transporting and injection layer was formed.
  • magnesium and silver were deposited to a thickness of 160 4 in a weight ratio of 1: 4 to form a cathode, thereby manufacturing an organic light emitting device.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 ⁇ / sec
  • the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 ⁇ / sec
  • silver and magnesium at 2 ⁇ / sec
  • the vacuum degree was 2 during deposition.
  • An organic light emitting device was manufactured by maintaining 10 ⁇ 7 ⁇ 5 ⁇ 10 ⁇ 6 torr.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound shown in Table 1 below instead of the compound 1.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound shown in Table 1 below instead of the compound 1.
  • Table 1 the compounds GH-A, GH-B, GH-C and GH-D are as follows.
  • T95 voltage, efficiency, and lifetime
  • the organic light emitting device including the compound corresponding to one embodiment exhibited characteristics of low voltage, high efficiency, and long life compared to the organic light emitting device including the comparative example compound having a similar structure.
  • Example 5 containing Compound 5 and Comparative Examples 1 and 2 containing Compound GH-A and GH-B whether or not to resolve the steric hindrance according to the substitution position of the N-containing substituent of dibenzofuran is a molecule. It is presumed to have made a great contribution to stability.
  • the Examples and Comparative Examples 3 and 4 including the compounds GH-C and GH-D it is expected that the electron stability of the compound of the Example is increased through additional bonding between orbitals in the molecule.
  • substrate 2 anode

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

Abstract

La présente invention concerne un nouveau composé et une diode électroluminescente organique le comprenant.
PCT/KR2019/015682 2018-11-16 2019-11-15 Nouveau composé et diode électroluminescente organique le comprenant Ceased WO2020101439A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US17/044,789 US11795161B2 (en) 2018-11-16 2019-11-15 Compound and organic light emitting device comprising same
CN201980019040.1A CN111868053B (zh) 2018-11-16 2019-11-15 新的化合物和包含其的有机发光器件

Applications Claiming Priority (4)

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KR20180141846 2018-11-16
KR10-2018-0141846 2018-11-16
KR10-2019-0146190 2019-11-14
KR1020190146190A KR102336599B1 (ko) 2018-11-16 2019-11-14 신규한 화합물 및 이를 포함하는 유기발광 소자

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WO2020101439A1 true WO2020101439A1 (fr) 2020-05-22

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110043342A (ko) * 2009-10-21 2011-04-27 제일모직주식회사 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
KR20130078437A (ko) * 2011-12-30 2013-07-10 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20130094222A (ko) * 2010-06-24 2013-08-23 도레이 카부시키가이샤 발광 소자 재료 및 발광 소자
KR20160052200A (ko) * 2014-11-04 2016-05-12 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 이를 포함하는 유기 광전자 소자 및 표시장치
KR20180073239A (ko) * 2016-12-22 2018-07-02 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110043342A (ko) * 2009-10-21 2011-04-27 제일모직주식회사 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
KR20130094222A (ko) * 2010-06-24 2013-08-23 도레이 카부시키가이샤 발광 소자 재료 및 발광 소자
KR20130078437A (ko) * 2011-12-30 2013-07-10 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20160052200A (ko) * 2014-11-04 2016-05-12 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 이를 포함하는 유기 광전자 소자 및 표시장치
KR20180073239A (ko) * 2016-12-22 2018-07-02 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치

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