WO2019190231A1 - Composé polycyclique et diode électroluminescente organique le comprenant - Google Patents

Composé polycyclique et diode électroluminescente organique le comprenant Download PDF

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WO2019190231A1
WO2019190231A1 PCT/KR2019/003653 KR2019003653W WO2019190231A1 WO 2019190231 A1 WO2019190231 A1 WO 2019190231A1 KR 2019003653 W KR2019003653 W KR 2019003653W WO 2019190231 A1 WO2019190231 A1 WO 2019190231A1
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차용범
전상영
홍성길
서상덕
이민우
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주식회사 엘지화학
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Priority to CN201980003809.0A priority Critical patent/CN111051315B/zh
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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
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • 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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • 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]
    • H10K50/18—Carrier blocking layers

Definitions

  • the present specification relates to a polycyclic compound and an organic light emitting device including the same.
  • an organic light emitting device is a light emitting device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and the organic semiconductor material.
  • the organic light emitting device can be classified into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting element of the form.
  • the second is a light emitting device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • organic light emitting devices When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
  • organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
  • the luminescent material includes blue, green, and red luminescent materials and yellow and orange luminescent materials necessary to realize better natural colors depending on the emission color.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light.
  • the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • X is O or S
  • L1 and L2 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substitute
  • a is an integer of 0 to 4,
  • the first electrode A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
  • the compound according to at least one embodiment may improve the lifespan and / or in the organic light emitting device.
  • the compounds described herein can be used as the material of the hole injection layer, hole transport layer, electron suppression layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • FIG. 3 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 9, a light emitting layer 7, a hole blocking layer 10, an electron injection and transport layer ( 11) and an example of the organic light-emitting device consisting of the cathode 4 are shown.
  • the present specification provides a compound represented by the following Formula 1.
  • the compound represented by the following formula (1) is used in the organic material layer of the organic light emitting device, the efficiency of the organic light emitting device is always.
  • X is O or S
  • L1 and L2 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substitute
  • a is an integer of 0 to 4,
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is replaced, that is, a position where the substituent can be substituted, if two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group; An alkyl group; Cycloalkyl group; Arylamine group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • carbon number of an ester group is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another 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.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-jade Although there exist a tilt group etc., it is not limited to these.
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30.
  • 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 silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but is not limited thereto.
  • the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
  • Diphenylamine group N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine Groups, N-phenanthrenylfluorenylamine groups, N-biphenylfluorenylamine groups, and the like, but are not limited thereto.
  • the N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.
  • the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N in the amine group.
  • the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted for N in the amine group.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • arylamine group examples include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine Groups, 9-methyl-anthracenylamine groups, diphenyl amine groups, phenyl naphthyl amine groups, biphenyl phenyl amine groups, and the like, but are not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl group, triphenyl 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.
  • Spirofluorenyl groups such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenyl fluorenyl group).
  • the present invention is not limited thereto.
  • the aryl group in the alkylaryl group, the aryloxy group, the arylthioxy group, the aryl sulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group, and the arylamine group has a description regarding the aforementioned aryl group. Can be applied.
  • the alkyl group of the alkylaryl group, the alkylthioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkylamine group, the alkylamine group, and the N-alkylheteroarylamine group may be applied to the description of the aforementioned alkyl group.
  • Alkyl thioxy groups include methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thioxy group and the like, and alkyl sulfoxy groups include mesyl, ethyl sulfoxy, propyl sulfoxy and butyl sulfoxy groups.
  • the present invention is not limited thereto.
  • the heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms.
  • the heterocyclic group include pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, and the like. It is not limited only to.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • heteroaryl group the heteroaryl group of the heteroarylamine group, the description of the aforementioned heterocyclic group may be applied.
  • adjacent The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in an atom in which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
  • ring in a substituted or unsubstituted ring in which adjacent groups are bonded to each other, a “ring” means a hydrocarbon ring; Or heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.
  • the description of the aryl group may be applied except that the aromatic hydrocarbon ring is monovalent.
  • the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of N, O, P, S, Si, Se, and the like. can do.
  • the heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.
  • X is O or S.
  • L1 and L2 are each independently, a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.
  • L1 and L2 are each independently, a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.
  • L1 and L2 are each independently, a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
  • L1 and L2 are each independently a substituted or unsubstituted arylene group, it may be any one selected from the following structures.
  • A1 and A2 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
  • L1 and L2 are each independently a substituted or unsubstituted divalent heterocyclic group, it may be any one selected from the following structures.
  • Y1 to Y5 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted or unsubstituted al
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted diaryl phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted C1-C60 alkylamine group; A substituted or unsubstituted aralkylamine group having 6 to 60 carbon atoms; Substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted diaryl phosphine oxide group having 12 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted C1-C30 alkylamine group; A substituted or unsubstituted aralkylamine group having 6 to 30 carbon atoms; Substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted diaryl phosphine oxide group having 12 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted C1-C20 alkylamine group; A substituted or unsubstituted aralkylamine group having 6 to 20 carbon atoms; Substituted or unsubstituted arylamine group having 6 to 20 carbon atoms; A substituted or unsubstituted diaryl phosphine oxide group having 12 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms containing at least one N.
  • Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrene group, Substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazole group, substituted or unsubstituted A substituted amine group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, or a substituted or unsubstituted phosphine oxide
  • Ar1 and Ar2 are each independently a phenyl group; Naphthylene group; Biphenyl group; Phenanthrene group; Triphenylene group; A fluorenyl group substituted with a substituent selected from the group consisting of a methyl group and a phenyl group; Dibenzofuran group; Dibenzothiophene group; Carbazole groups unsubstituted or substituted with a phenyl group; A substituted or unsubstituted amine group selected from the group consisting of a phenyl group, a biphenyl group, a naphthylene group and a fluorenyl group substituted with a methyl group; A pyridine group unsubstituted or substituted with a phenyl group; A pyrimidine group unsubstituted or substituted with a phenyl group; Triazine group unsubstituted or substituted with a phenyl group;
  • Ar1 and Ar2 may be any one selected from the following structures.
  • Formula 1 is represented by the following formula (2).
  • Chemical Formula 1 is represented by the following Chemical Formula 3 or 4.
  • Chemical Formula 1 may be represented by any one of the following structures.
  • Compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by the production method described below.
  • the compound of Formula 1 may be prepared in the core structure as shown in Schemes A to F.
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • the conjugation length of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
  • a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material and the hole suppression layer material used in the manufacture of the organic light emitting device into the core structure to synthesize a material satisfying the requirements of each organic material layer can do.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
  • the compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
  • 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, a hole suppression 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 material layers.
  • the organic material layer may include an electron transport layer or an electron injection layer, the electron transport layer or an electron injection layer may include a compound represented by the formula (1).
  • the organic material layer may include a hole injection layer or a hole transport layer
  • the hole injection layer or hole transport layer may include a compound represented by the formula (1).
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 as a dopant of the light emitting layer.
  • the organic material layer may include an electron suppression layer, and the electron suppression layer may include a compound represented by Chemical Formula 1.
  • the organic material layer may include a hole blocking layer, and the hole blocking layer may include a compound represented by Chemical Formula 1.
  • the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metal compounds. May be included as the dopant.
  • the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a dopant, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant. have.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 illustrates an organic light emitting device in which 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 are sequentially stacked on a substrate 1.
  • the structure is illustrated.
  • the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, or the electron transport layer 8.
  • the compound is the hole injection layer 5, electron suppression layer 9, light emitting layer 7 or hole blocking It may be included in layer 10.
  • the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, an organic material layer including a hole injection layer, an electron suppression layer, a light emitting layer and a hole suppression layer thereon, and then depositing a material that can be used as a cathode thereon.
  • PVD metal vapor deposition
  • 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 organic material layer may have a multilayer structure including a hole injection layer, an electron suppression layer, a light emitting layer, a hole suppression layer, and the like, but is not limited thereto and may have a single layer structure.
  • the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal and an 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, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the electron suppression layer and the hole suppression layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • Alq 3 8-hydroxyquinoline aluminum complex
  • Carbazole series compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole series compounds include Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Iridium complex used as the dopant of the light emitting layer is as follows, but is not limited thereto.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer.
  • a material having high mobility to electrons is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. was used as a detergent
  • distilled water was filtered secondly as a filter of Millipore Co. as a distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the compound of the following compound HI1 and the following compound HI2 was thermally vacuum deposited to a thickness of 100 kPa so that the ratio of 98: 2 (molar ratio) was formed on the ITO transparent electrode as the anode thus prepared, thereby forming a hole injection layer.
  • Compound (1150.) Represented by the following formula HT1 was vacuum deposited on the hole injection layer to form a hole transport layer.
  • the compound of Preparation Example 1 was vacuum deposited on the hole transport layer with a film thickness of 50 kV to form an electron suppressing layer.
  • the light emitting layer was formed by vacuum depositing the compound represented by the following formula BH and the compound represented by the following formula BD at a weight ratio of 50: 1 on the electron suppressing layer with a film thickness of 200 kPa.
  • a hole blocking layer was formed by vacuum depositing a compound represented by the following formula HB1 with a film thickness of 50 kPa on the light emitting layer.
  • the compound represented by the following formula ET1 and the compound represented by the following formula LiQ were vacuum-deposited at a weight ratio of 1: 1 on the hole blocking layer to form an electron injection and transport layer having a thickness of 30 kPa.
  • Lithium fluoride (LiF) and aluminum were deposited on the electron injection and transport layer sequentially to a thickness of 12 ⁇ and 1,000 ⁇ to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 ⁇ / sec
  • the lithium fluoride of the cathode was maintained at 0.3 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 2 ⁇ / sec.
  • An organic light-emitting device was manufactured by maintaining ⁇ 7 to 5 ⁇ 10 ⁇ 6 torr.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of the compound of Preparation Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of the compound of Preparation Example 1.
  • the compounds of EB2 and EB3 used in Table 1 below are as follows.
  • T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1600 nit).
  • Example 1-1 Preparation Example 1 4.20 6.55 (0.144, 0.045) 240
  • Example 1-2 Preparation Example 2 4.11 6.55 (0.142, 0.045) 275
  • Example 1-3 Preparation Example 5 4.25 6.44 (0.143, 0.046) 265
  • Example 1-4 Preparation Example 7 4.27 6.55 (0.144, 0.045) 250
  • Example 1-5 Preparation Example 8
  • Example 1-6 Preparation Example 9 4.38 6.57 (0.144, 0.047) 250
  • Example 1-7 Preparation Example 13 4.37 6.59 (0.143, 0.046) 265
  • Example 1-8 Preparation Example 14 4.36 6.44 (0.144, 0.045) 240 Comparative Example 1-1 EB2 5.02 5.73 (0.142, 0.047) 180 Comparative Example 1-2
  • the organic light emitting device using the compound of the present invention as an electron suppressing layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
  • Examples 1-1 to 1-8 When phenanthrofurocarbazole and phenanthrothienocarbazole were used as cores and arylamines and p-type substituents such as dibenzofuran, dibenzothiophene, and carbazole were used as the electron suppression layer, they showed low voltage, high efficiency, and long life.
  • phenanthrofurocarbazole and phenanthrothienocarbazole were used as cores and arylamines and p-type substituents such as dibenzofuran, dibenzothiophene, and carbazole were used as the electron suppression layer, they showed low voltage, high efficiency, and long life.
  • phenanthrofurocarbazole and phenanthrothienocarbazole were used as cores and arylamines and p-type substituents such
  • the compound according to the present invention was confirmed that the excellent electron blocking ability can be applied to the organic light emitting device.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the EB1 compound as an electron suppression layer instead of the compound of Preparation Example 1, and using the compound shown in Table 2 below instead of HB1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the EB1 compound was used as an electron suppression layer instead of the compound of Preparation Example 1, and the following HB2 and HB3 compounds were used as hole blocking layers instead of HB1. It was.
  • the compounds of HB2 and HB3 used in Table 2 below are as follows.
  • T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1600 nit).
  • Example 2-1 Preparation Example 3 3.51 6.31 (0.143, 0.047) 265
  • Example 2-2 Preparation Example 4 3.54 6.25 (0.144, 0.046) 270
  • Example 2-3 Preparation Example 6 3.58 6.43 (0.143, 0.045) 280
  • Example 2-4 Preparation Example 10 3.53 6.42 (0.144, 0.046) 285
  • Example 2-5 Preparation Example 11 3.58 6.46 (0.145, 0.045) 270
  • Example 2-6 Preparation Example 12 3.63 6.43 (0.144, 0.046) 265
  • Example 2-7 Preparation Example 15 3.63 6.42 (0.143, 0.045) 285 Comparative Example 2-1 HB2 4.17 5.72 (0.139, 0.041) 130 Comparative Example 2-2 HB3 3.95 6.03 (0.141, 0.042) 205
  • the organic light emitting device using the compound of the present invention as a hole suppression layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
  • Examples 2-1 to 2-7 when phenanthrofurocarbazole and phenanthrothienocarbazole were used as cores and a substance linked with n-type substituents of cyanopyrimidine, triazine, pyrimidine, quinazoline and phosphine oxide was used as the electron suppressing layer, It can be seen that the characteristics of low voltage, high efficiency, and long life is shown.
  • the compound according to the present invention has excellent hole blocking ability and can be applied to an organic light emitting device.

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Abstract

La présente invention concerne un composé de formule chimique 1 et une diode électroluminescente organique le comprenant.
PCT/KR2019/003653 2018-03-28 2019-03-28 Composé polycyclique et diode électroluminescente organique le comprenant WO2019190231A1 (fr)

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