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WO2023121096A1 - Nouveau composé et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé et dispositif électroluminescent organique l'utilisant Download PDF

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WO2023121096A1
WO2023121096A1 PCT/KR2022/020140 KR2022020140W WO2023121096A1 WO 2023121096 A1 WO2023121096 A1 WO 2023121096A1 KR 2022020140 W KR2022020140 W KR 2022020140W WO 2023121096 A1 WO2023121096 A1 WO 2023121096A1
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light emitting
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Korean (ko)
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조혜민
이동훈
한미연
정민우
박슬찬
김훈준
이호중
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LG Chem Ltd
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    • 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
    • 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
    • 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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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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
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Definitions

  • the present invention relates to a novel compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using an 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 are being conducted.
  • An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode.
  • the organic material layer is often composed of a multi-layered structure composed of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device including the same.
  • the present invention provides a compound represented by Formula 1 below:
  • n is an integer from 1 to 6;
  • X is O or S
  • L 1 and L 2 are each independently a single bond; Substituted or unsubstituted C 6-60 arylene; Or a C 2-60 heteroarylene containing at least one selected from the group consisting of substituted or unsubstituted O, S, Si, P and B,
  • Ar 1 is cyano; Substituted or unsubstituted C 6-60 aryl; Or a C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted O, S, Si, P and B,
  • Ar 2 and Ar 3 are each independently a substituted or unsubstituted C 6-60 aryl; Or a C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted O, S, Si, P, and B.
  • 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 compound represented by Chemical Formula 1. do.
  • the compound represented by Chemical Formula 1 may be used as a material for an organic layer of an organic light emitting diode, and may improve efficiency, low driving voltage, and/or lifespan characteristics of an organic light emitting diode.
  • the compound represented by Chemical Formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, electron suppression, light emission, electron transport, or electron injection.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
  • FIG. 2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), a hole blocking layer (9), an electron transport layer (10) ,
  • An example of an organic light emitting device composed of an electron injection layer 11 and a cathode 4 is shown.
  • FIG. 3 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), a hole blocking layer (9), an electron injection and transport layer ( 12) and an example of an organic light emitting device composed of a cathode 4 is shown.
  • the present invention provides a compound represented by Formula 1 above.
  • substituted or unsubstituted means 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; an alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; Aralkenyl group; Alkyl aryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing at least one of N, O, and S atoms, or substituted or
  • a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in 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 aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester 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 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 a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. but not limited to
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, 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 straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one 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, etc., but is 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 number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms 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 be bonded to each other to form a spiro structure.
  • the fluorenyl group is substituted, etc.
  • it is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing at least one of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms.
  • the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, and an acridyl group.
  • pyridazine group pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group , carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadia A zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.
  • an aralkyl group, an aralkenyl group, an alkylaryl group, and an aryl group among arylamine groups are the same as the examples 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 examples of the above-mentioned alkyl group.
  • the description of the heterocyclic group described above may be applied to the heteroaryl of the heteroarylamine.
  • the alkenyl group among the aralkenyl groups is the same as the examples 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 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 the hydrocarbon ring is formed by combining two substituents.
  • the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.
  • the compound represented by Formula 1 includes dibenzofuran or dibenzothiophene containing at least one deuterium, and an aryl or heteroaryl-substituted triazine group bonded thereto; and an aryl or heteroaryl group, and does not include a nitrogen-containing heterocycle other than the triazine group.
  • a compound satisfying the structure of Chemical Formula 1 exhibits low voltage when applied to an organic light emitting device and has excellent efficiency and lifetime characteristics.
  • Formula 1 may be specifically represented by Formula 1-1 or 1-2:
  • n, L 1 , L 2 , and Ar 1 to Ar 3 are as defined in Formula 1.
  • n is an integer from 4 to 6.
  • one or more hydrogens of L 1 , L 2 , Ar 1 to Ar 3 may be substituted with deuterium.
  • L 1 and L 2 are each independently a single bond; A substituted or unsubstituted C 6-20 arylene; Or a C 2-20 heteroarylene containing at least one selected from the group consisting of substituted or unsubstituted O, S, Si, P, and B.
  • the heteroatom of the heteroaryl may be O and/or S.
  • L 1 and L 2 are each independently a single bond; phenylene; or biphenylylene, wherein L 1 and L 2 may each independently be substituted with one or more deuterium atoms or may be unsubstituted.
  • L 1 and L 2 are each independently a single bond; phenylene; or biphenylylene.
  • Ar 1 is cyano; Substituted or unsubstituted C 6-20 aryl; Or a C 2-20 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted O, S, Si, P, and B.
  • the heteroatom of the heteroaryl may be O and/or S.
  • Ar 1 is aryl or heteroaryl, one or more hydrogens may be replaced with deuterium.
  • Ar 1 is cyano; phenyl; biphenylyl; terphenylyl; triphenylenyl; benzofuranyl; benzothiophenyl; dibenzofuranyl; or dibenzothiophenyl, and the substituents may be unsubstituted or substituted with one or more deuterium atoms.
  • Ar 1 is cyano; phenyl unsubstituted or substituted with one or more deuterium; Biphenylyl unsubstituted or substituted with one or more deuterium; terphenylyl unsubstituted or substituted with one or more deuterium; triphenylenyl unsubstituted or substituted with one or more deuterium; Benzofuranyl unsubstituted or substituted with one or more deuterium; Benzothiophenyl unsubstituted or substituted with one or more deuterium; dibenzofuranyl unsubstituted or substituted with one or more deuterium; or dibenzothiophenyl unsubstituted or substituted with one or more deuterium atoms.
  • Ar 2 and Ar 3 are substituted or unsubstituted C 6-20 aryl; Or a C 2-20 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted O, S, Si, P, and B.
  • the heteroatom of the heteroaryl may be O and/or S.
  • Ar 2 and Ar 3 may each be substituted with one or more deuterium atoms.
  • Ar 2 and Ar 3 are each independently phenyl; phenyl substituted with one or more substituents selected from the group consisting of halogen, cyano, trimethylsilyl, C 1-4 alkyl, and C 1-4 alkenyl; biphenylyl; terphenylyl; naphthyl; 9,9-dimethylfluorenyl; 9,9-diphenylfluorenyl; triphenylenyl; chrysenyl; benzofuranyl; benzothiophenyl; dibenzofuranyl; phenyldibenzofuranyl; dibenzothiophenyl; or phenyldibenzothiophenyl, and the substituents may be unsubstituted or substituted with one or more deuterium atoms.
  • substituents may be unsubstituted or substituted with one or more deuterium atoms.
  • the 'phenyl substituted with one or more substituents selected from the group consisting of halogen, cyano, trimethylsilyl, C 1-4 alkyl, and C 1-4 alkenyl' is, for example, fluorophenyl, cyanophenyl , trimethylsilanophenyl, dimethylphenyl, t-butylphenyl, or ethenylphenyl.
  • the 'trimethylsilyl, C 1-4 alkyl, and C 1-4 alkenyl' may each be substituted with one or more deuterium atoms.
  • Ar 2 and Ar 3 are each independently phenyl unsubstituted or substituted with one or more deuterium atoms; Fluorophenyl unsubstituted or substituted with one or more deuterium; Cyanophenyl unsubstituted or substituted with one or more deuterium; Trimethylsilanophenyl unsubstituted or substituted with one or more deuterium; dimethylphenyl unsubstituted or substituted with one or more deuterium; t-butylphenyl unsubstituted or substituted with one or more deuterium; ethenylphenyl unsubstituted or substituted with one or more deuterium; Biphenylyl unsubstituted or substituted with one or more deuterium; terphenylyl unsubstituted or substituted with one or more deuterium; naphthyl unsubstituted or substituted with one or more deuterium; 9,9-dimethyl
  • the present invention provides a method for preparing the compound represented by Formula 1 above.
  • the compound represented by Chemical Formula 1 can be prepared by the preparation method of Reaction Scheme 1 below:
  • Scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and a reactor for the Suzuki coupling reaction may be modified as known in the art.
  • the manufacturing method may be more specific in Preparation Examples to be described later.
  • 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 includes the compound represented by Chemical Formula 1. do.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or 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, and the like as organic layers.
  • the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.
  • the organic layer may include a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1.
  • the compound according to the present invention can be used as a host of the light emitting layer.
  • the organic material layer may include a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, hole transport layer, or electron blocking layer includes the compound represented by Formula 1 above.
  • the organic light emitting device according to the present invention may be a normal type organic light emitting device 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 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.
  • FIGS. 1 to 3 the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 to 3 .
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
  • the compound represented by Chemical Formula 1 may be included in the organic material layer.
  • FIG. 2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), a hole blocking layer (9), an electron transport layer (10) ,
  • An example of an organic light emitting device composed of an electron injection layer 11 and a cathode 4 is shown.
  • the compound represented by Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer. It may be included in the light emitting layer.
  • the compound represented by Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, and the electron injection and transport layer. For example, it may be included in the light emitting layer.
  • the organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Chemical Formula 1. Also, when the organic light emitting device includes a plurality of organic material layers, 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. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode After forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and depositing a material that can be used as a cathode thereon, it can be prepared. In addition to this method, 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.
  • PVD physical vapor deposition
  • 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 coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
  • the cathode material a material having a high work function is generally preferred so that holes can be smoothly injected into the organic 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; 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 so as to easily inject electrons into the organic material layer.
  • Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and generated in the light emitting layer
  • a compound that prevents migration of excitons to the electron injecting layer or electron injecting material and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • HOMO highest occupied molecular orbital
  • the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic matter, 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 the holes to the light emitting layer.
  • a hole transport material a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is a material having high hole mobility. This is suitable Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.
  • the electron suppression layer serves to improve the efficiency of the organic light emitting device by suppressing the transfer of electrons injected from the cathode to the anode without recombination in the light emitting layer.
  • the light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material includes a condensed aromatic ring derivative or a compound containing a hetero ring.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.
  • the compound represented by Chemical Formula 1 may be used as a host material of the light emitting layer, and in this case, low voltage, high efficiency and/or long life characteristics of the organic light emitting device may be obtained.
  • Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanthene, etc.
  • styrylamine compounds include substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted.
  • metal complexes include, but are not limited to, iridium complexes and platinum complexes.
  • 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 Al complexes 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 having a low work function followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by a layer of aluminum or silver.
  • the electron injection layer is a layer for injecting electrons from an electrode, has the ability to transport electrons, has an excellent electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes of excitons generated in the light emitting layer.
  • a compound that prevents migration to a layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preonylidene methane, anthrone, etc. and their derivatives, metals complex compounds and nitrogen-containing 5-membered ring derivatives, 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, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.
  • the electron injection and transport layer may be formed as a single layer by simultaneously depositing the electron transport material and the electron injection material.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side 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 an organic light emitting device.
  • Compound 2 was obtained in the same manner as in the preparation method of Compound 1 of Preparation Example 1, except that Intermediate B was used instead of Intermediate A.
  • Compound 8 was obtained in the same manner as in the preparation method of Compound 1 in Preparation Example 1, except that Intermediate 8-2 and Intermediate H were used instead of Intermediate 1-2 and Intermediate A.
  • Compound 10 was obtained in the same manner as in the preparation method of Compound 1 in Preparation Example 1, except that Intermediate I was used instead of Intermediate 10-2 and Intermediate A instead of Intermediate 1-2.
  • a glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 1,400 ⁇ was put in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • a product of Fischer Co. was used as a detergent
  • distilled water filtered through a second filter of a product of Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner.
  • solvents such as isopropyl alcohol, acetone, and methanol
  • the following HT-A compound and the following PD compound were thermally vacuum deposited at a weight ratio of 95:5 to a thickness of 100 ⁇ , and then only the following HT-A compound was deposited to a thickness of 1150 ⁇ to form a hole transport layer. formed.
  • the following HT-B compound was thermally vacuum deposited to a thickness of 450 ⁇ to form an electron blocking layer.
  • a light emitting layer was formed by vacuum depositing Compound 1 prepared above and the following GD compound at a weight ratio of 85:15 to a thickness of 400 ⁇ .
  • the following ET-A compound was vacuum deposited to a thickness of 50 ⁇ to form a hole blocking layer.
  • the following ET-B compound and the following Liq compound were thermally vacuum deposited to a thickness of 250 ⁇ in a weight ratio of 2:1, followed by vacuum deposition of LiF and magnesium to a thickness of 30 ⁇ in a weight ratio of 1:1 Thus, an electron injection and transport layer was formed.
  • magnesium and silver were deposited to a thickness of 160 ⁇ at 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 deposition rate of lithium fluoride on the anode was 0.3 ⁇ /sec, and the deposition rate of silver and magnesium was 2 ⁇ /sec. While maintaining ⁇ 10 -7 to 5 ⁇ 10 -6 torr, an organic light emitting device was fabricated.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Example 1.
  • Examples 12 to 13 and Comparative Examples 4 to 6 instead of Compound 1, the compounds shown in Table 1 were used in a weight ratio of 1:1 to manufacture organic light emitting devices. Taking Example 12 as an example, Compound 1 and Compound H-2 were used in a weight ratio of 1:1 instead of Compound 1 in Example 1. In Table 1 below, compounds H-2 and C1 to C3 are respectively as follows.
  • T95 Voltage, efficiency, and lifetime
  • Examples 1 to 11 and Comparative Examples 1 to 3 are device examples using a single host in the light emitting layer.
  • the compound of Formula 1 is a structure in which deuterium is substituted for dibenzofuran or dibenzothiophene, and is particularly effective in improving life characteristics.
  • Examples 12 and 13 are device examples using two types of hosts in the light emitting layer. Comparing the devices of Examples 12 and 13 with the devices of Comparative Examples 4 to 6, even when two types of hosts are used in the light emitting layer, when the compound of the present invention is used, the efficiency is higher, and the lifetime characteristic is greatly improved. can confirm that
  • substrate 2 anode
  • organic material layer 4 cathode

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique l'utilisant.
PCT/KR2022/020140 2021-12-22 2022-12-12 Nouveau composé et dispositif électroluminescent organique l'utilisant Ceased WO2023121096A1 (fr)

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