WO2020162703A1 - Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant Download PDF

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WO2020162703A1
WO2020162703A1 PCT/KR2020/001744 KR2020001744W WO2020162703A1 WO 2020162703 A1 WO2020162703 A1 WO 2020162703A1 KR 2020001744 W KR2020001744 W KR 2020001744W WO 2020162703 A1 WO2020162703 A1 WO 2020162703A1
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group
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substituted
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허동욱
홍성길
허정오
한미연
이재탁
양정훈
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주식회사 엘지화학
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Priority to CN202080007239.5A priority Critical patent/CN113227076A/zh
Publication of WO2020162703A1 publication Critical patent/WO2020162703A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D409/02—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
    • C07D409/10—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 linked by a carbon chain containing aromatic rings
    • 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

Definitions

  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • An 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 made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.
  • Patent Document 0001 Korean Patent Publication No. 10-2013-073537
  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula 1:
  • A is a naphthalene ring
  • Y is S, or O
  • R 1 and R 2 are each independently hydrogen, deuterium, or substituted or unsubstituted C 1-10 alkyl,
  • X 1 , X 2 and X 3 are each independently N or CR', provided that at least two of them are N,
  • R' is each independently hydrogen, deuterium, substituted or unsubstituted C 1-10 alkyl, substituted or unsubstituted C 6-30 aryl, or at least one hetero atom selected from the group consisting of N, O and S It is a substituted or unsubstituted C 5-60 heteroaryl containing,
  • L is a single bond, or a substituted or unsubstituted C 6-30 arylene
  • Ar 1 and Ar 2 are each independently hydrogen, deuterium, substituted or unsubstituted C 1-10 alkyl, substituted or unsubstituted C 6-30 aryl, or at least one selected from the group consisting of N, O and S A substituted or unsubstituted C 5-60 heteroaryl containing a hetero atom,
  • n are each independently an integer of 0 to 4.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the polymer of the present invention.
  • the compound represented by Chemical Formula 1 may be used as a material of an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device.
  • the compound represented by Chemical 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 comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting device comprising 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 I did it.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two
  • a substituent to which two or more substituents are connected 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 connected.
  • 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 ester group may be substituted with an oxygen of the ester group with a C 1 to C 25 linear, branched or cyclic chain alkyl group or a C 6 to C 25 aryl group.
  • 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 it 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 specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be a linear or branched chain, and the number of carbon atoms 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 linear or branched chain, and the number of carbon atoms 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 is preferably 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 an exemplary embodiment, the number of carbon atoms in the aryl group is 6 to 30. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Etc When the fluorenyl group is substituted, Etc.
  • Etc it is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms.
  • heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl 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 , Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthro
  • the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group.
  • the above description of the heterocyclic group may be applied.
  • the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene is a divalent group.
  • the description of the aforementioned heterocyclic group 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 the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents.
  • the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that the heterocycle is formed by bonding of two substituents.
  • the compound represented by Formula 1 is a compound represented by Formulas 2 to 9:
  • Y, R 1 , R 2 , L, X 1 , X 2 , X 3 , Ar 1 , Ar 2 , m and n are as previously defined.
  • R 1 and R 2 are each independently hydrogen, deuterium, or substituted or unsubstituted C 1-10 alkyl.
  • R' is hydrogen
  • L is a single bond, phenylene or biphenylylene.
  • Ar 1 and Ar 2 are each independently phenyl, methylphenyl, biphenylyl, naphthyl, naphthylphenyl, benzonitrile, benzonitrilephenyl
  • Ar 1 and Ar 2 are each independently phenyl, methylphenyl, biphenylyl, Naphthyl, naphthylphenyl, benzonitrile, benzonitrilephenyl, dibenzofuranyl, dibenzothiophenyl, pyridinyl, phenylpyridinyl, pyridinylphenyl, carbazol-9-yl, 9-phenyl-9H-carbazolyl Or 9H-carbazol-9-yl-N-phenyl.
  • the compound represented by Formula 1 may be any one selected from the group consisting of:
  • fluorene and xanthene form a spiro bond, and the electrons of the unshared electron pair of the central atom (oxygen or sulfur) of xanthene (or thioxanthene)
  • the effect of increasing device efficiency can be realized.
  • a naphthalene guro in which an additional benzene ring is condensed in the benzene ring of xanthene (or thioxanthene)
  • a triazine-based substituent in another benzene ring in which a naphthalene structure is not formed, electron attracting property is enhanced, and an effect of increasing the efficiency in an organic light emitting device can be realized.
  • the compound represented by Formula 1 can be prepared by a method according to Scheme A below.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • Reaction Scheme A the other variables excluding X are as defined in Formula 1, and X is halogen, preferably Cl or Br.
  • X is halogen, preferably Cl or Br.
  • the reactor, catalyst, solvent, etc. to be used can be changed to suit the desired product.
  • the present invention provides an organic light-emitting device including the compound represented by Formula 1 above.
  • the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 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 multilayer 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, 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 may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport may be represented by Formula 1 It includes the compound displayed.
  • the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • 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 the layer that simultaneously injects and transports electrons includes the compound represented by Formula 1 above.
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability, a deep HOMO level of 6.0 eV or more, a high triplet energy (ET), and hole stability.
  • an n-type dopant used in the art may be mixed and used.
  • 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.
  • the organic light emitting device according to the present invention may be an inverted type organic light emitting device 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 an 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 comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the emission layer.
  • FIG. 2 shows an example of an organic light emitting device comprising 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 done.
  • the compound represented by 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.
  • the organic light-emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic material layers 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 may 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 manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Chemical Formula 1 may be formed into 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 coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode 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 cathode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the cathode 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); Combinations of metals and oxides such as ZnO:Al or SNO 2 :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as 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; There are multilayered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that injects holes from the electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated from the light emitting layer.
  • a compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable.
  • the HOMO (highest occupied molecular orbital) 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 materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer by receiving holes from the hole injection layer, and is a material capable of transporting holes from the anode or the hole injection layer as a hole transport material and transferring them to the light emitting layer. This is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the light-emitting material is a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • the emission layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials 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, and periflanthene having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.
  • an electron transport material a material capable of injecting electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes containing 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 conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer
  • a compound that prevents migration to the layer and has excellent thin film formation ability is preferable.
  • Complex compounds and nitrogen-containing 5-membered ring derivatives but are not limited thereto.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, 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-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • Example 1 instead of the compound la (19.7 mmol), 2a (19.7 mmol) of Scheme 2 was used, and instead of the compound lb (19.7 mmol), 2b (19.7 mmol) of Scheme 2 was used,
  • the compound represented by Formula E2 was prepared in the same manner as in Example 1 of E1.
  • Example 1 instead of compound la (19.7 mmol), 3a (19.7 mmol) of Scheme 3 was used, and instead of compound lb (19.7 mmol), 3b (19.7 mmol) of Scheme 3 was used, A compound represented by Formula E3 was prepared in the same manner as in Example 1 of E1.
  • Example 1 instead of compound la (19.7 mmol), 4a (19.7 mmol) of Scheme 4 was used, and instead of compound lb (19.7 mmol), 4b (19.7 mmol) of Scheme 4 was used, A compound represented by Formula E4 was prepared in the same manner as in Example 1 of E1.
  • Example 1 instead of the compound la (19.7 mmol), 5a (19.7 mmol) of Scheme 5 was used, and instead of the compound lb (19.7 mmol), 5b (19.7 mmol) of Scheme 5 was used, A compound represented by Formula E5 was prepared in the same manner as in Example 1 of E1.
  • Example 1 instead of compound la (19.7 mmol), 6a (19.7 mmol) of Scheme 6 was used, and instead of compound lb (19.7 mmol), 6b (19.7 mmol) of Scheme 6 was used, A compound represented by Formula E6 was prepared in the same manner as in Example 1 of E1.
  • Example 1 instead of the compound la (19.7 mmol), 7a (19.7 mmol) of Scheme 7 was used, and instead of the compound lb (19.7 mmol), 7b (19.7 mmol) of Scheme 7 was used, A compound represented by Formula E7 was prepared in the same manner as in Example 1 of E1.
  • Example 1 instead of the compound la (19.7 mmol), 8a (19.7 mmol) of Scheme 8 was used, and instead of the compound lb (19.7 mmol), 8b (19.7 mmol) of Scheme 8 was used, A compound represented by Formula E8 was prepared in the same manner as in Example 1 of E1.
  • Example 1 instead of the compound la (19.7 mmol), 9a (19.7 mmol) of Scheme 9 was used, and instead of the compound lb (19.7 mmol), 9b (19.7 mmol) of Scheme 9 was used,
  • the compound represented by Formula E9 was prepared in the same manner as in Example 1 of E1.
  • Example 1 in place of the compound la (19.7 mmol), 10a (19.7 mmol) of Scheme 10 was used, and instead of the compound lb (19.7 mmol), 10b (19.7 mmol) of Scheme 10 was used, A compound represented by Formula E10 was prepared in the same manner as in Example 1 of E1.
  • Example 1 instead of the compound la (19.7 mmol), 11a (19.7 mmol) of Scheme 11 was used, and instead of the compound lb (19.7 mmol), 11b (19.7 mmol) of Scheme 11 was used,
  • the compound represented by Formula E11 was prepared in the same manner as in Example 1 of E1.
  • Example 1 instead of the compound la (19.7 mmol), 12a (19.7 mmol) of Scheme 12 was used, and instead of the compound lb (19.7 mmol), 12b (19.7 mmol) of Scheme 12 was used, A compound represented by Formula E12 was prepared in the same manner as in Example 1 of E1.
  • Example 1 instead of the compound lb (19.7 mmol), except for using 13b (19.7 mmol) of Scheme 13, a compound represented by Formula E13 was prepared in the same manner as in the manufacturing method of E1 of Example 1 I did.
  • a glass substrate coated with a thin film of 1000 ⁇ of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product made by Fischer Co. was used as a detergent
  • distilled water secondarily filtered by a filter made by Millipore Co. was used as distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ to form a hole injection layer.
  • the following HAT compound 50 ⁇ and the following HT-A compound 60 ⁇ were sequentially vacuum-deposited on the hole injection layer to form a hole transport layer.
  • the following BH compound and BD compound with a thickness of 20 nm were vacuum-deposited on the hole transport layer at a weight ratio of 25:1 to form a light emitting layer.
  • the compound (E1) of Example 1 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350 ⁇ .
  • Lithium fluoride (LiF) at a thickness of 10 ⁇ and aluminum at a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • the deposition rate of organic materials was maintained at 0.4 to 0.9 ⁇ /sec
  • lithium fluoride at the cathode was maintained at a deposition rate of 0.3 ⁇ /sec
  • the vacuum degree during deposition was 1 ⁇ 10 ⁇ Maintaining 7 to 5 ⁇ 10 -5 torr, an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds of Examples 2 to 12 (E2 to E12) were used instead of the compound (E1) of Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the following compounds (ET-1-A to ET-1-L) were used instead of the compound (E1) of Example 1.
  • the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm 2 for the organic light emitting device manufactured in the above Experimental Examples and Comparative Examples, and the time at which the initial luminance becomes 90% at a current density of 20 mA/cm 2 (T90) was measured.
  • the results are shown in Table 1 below.
  • the compound represented by Formula 1 according to the present invention may be used in an organic material layer capable of simultaneously injecting electrons and transporting electrons in an organic light-emitting device.
  • the compound in which triazine or pyrimidine is substituted with xanthene or thioxanthene as in Chemical Formula 1 according to the present invention is triazine or pyrimidine in xanthene or thioxanthene. It can be seen that compared to the compound unsubstituted with azine or pyrimidine, the organic light-emitting device exhibits remarkably superior characteristics in terms of efficiency and lifespan.
  • substrate 2 anode

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

Abstract

La présente invention concerne un nouveau composé hétérocyclique et un dispositif électroluminescent organique l'utilisant.
PCT/KR2020/001744 2019-02-08 2020-02-07 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant WO2020162703A1 (fr)

Priority Applications (1)

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CN202080007239.5A CN113227076A (zh) 2019-02-08 2020-02-07 新型杂环化合物及利用其的有机发光器件

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KR20190015099 2019-02-08
KR10-2019-0015099 2019-02-08
KR10-2020-0014267 2020-02-06
KR1020200014267A KR102360902B1 (ko) 2019-02-08 2020-02-06 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120122897A (ko) * 2011-04-29 2012-11-07 에스에프씨 주식회사 신규한 화합물 및 이를 포함하는 유기전계발광소자
KR20140135117A (ko) * 2013-05-15 2014-11-25 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20180022190A (ko) * 2016-08-23 2018-03-06 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20180046150A (ko) * 2016-10-27 2018-05-08 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20180111558A (ko) * 2017-03-30 2018-10-11 주식회사 엘지화학 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120122897A (ko) * 2011-04-29 2012-11-07 에스에프씨 주식회사 신규한 화합물 및 이를 포함하는 유기전계발광소자
KR20140135117A (ko) * 2013-05-15 2014-11-25 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20180022190A (ko) * 2016-08-23 2018-03-06 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20180046150A (ko) * 2016-10-27 2018-05-08 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20180111558A (ko) * 2017-03-30 2018-10-11 주식회사 엘지화학 유기 발광 소자

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