WO2019190230A1 - Composé et diode électroluminescente organique le comprenant - Google Patents

Composé et diode électroluminescente organique le comprenant Download PDF

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WO2019190230A1
WO2019190230A1 PCT/KR2019/003652 KR2019003652W WO2019190230A1 WO 2019190230 A1 WO2019190230 A1 WO 2019190230A1 KR 2019003652 W KR2019003652 W KR 2019003652W WO 2019190230 A1 WO2019190230 A1 WO 2019190230A1
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group
substituted
formula
layer
light emitting
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PCT/KR2019/003652
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English (en)
Korean (ko)
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장분재
이동훈
정민우
이정하
한수진
박슬찬
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주식회사 엘지화학
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Priority to CN201980004778.0A priority Critical patent/CN111164080B/zh
Publication of WO2019190230A1 publication Critical patent/WO2019190230A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a compound represented by Formula 1 and an organic light emitting device including the same.
  • 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 has a multi-layered structure composed of different materials in order to increase efficiency and stability of the organic light emitting device.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification is to provide an organic light emitting device having a low driving voltage, high luminous efficiency, or good life characteristics by including a compound represented by the formula (1).
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • X is S or O
  • X1 to X3 are each independently N or CH, at least two of X1 to X3 is N,
  • Ar1 and Ar2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group,
  • R is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Y is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkenyl group,
  • n is an integer from 0 to 7, when n is 2 or more, R is the same as or different from each other,
  • n is an integer of 0-7 and Y is same or different when m is 2 or more.
  • an exemplary embodiment of the present specification is an organic light emitting device including a first electrode, a second electrode and one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer is represented by the formula (1) It provides an organic light emitting device comprising the compound represented.
  • the compound described herein may be used as a material of the organic material layer of the organic light emitting device.
  • the compounds described herein can be used as hole injection, hole transport, luminescence, electron transport or electron injection materials.
  • the organic light emitting device including the compound of the present invention may be improved in efficiency.
  • the organic light emitting device including the compound of the present invention may have a low driving voltage.
  • the organic light emitting device including the compound of the present invention may have improved lifetime characteristics.
  • 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 device 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, an electron blocking layer 9, a light emitting layer 7, an electron transport layer 8, an electron injection layer 10 and a cathode 4.
  • An example of the organic light emitting element made is shown.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent.
  • the position at which the substituent is substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position at which the substituent is substituted.
  • substituents are two or more, two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Hydroxyl group; An alkyl group; Aralkyl group; An alkoxy group; Alkenyl groups; Aryloxy group; Aryl group; And it is substituted or unsubstituted with one or more groups selected from the group consisting of a heteroaryl group, or two or more groups selected from the group selected from the group is substituted or unsubstituted.
  • an aryl alkenyl group may be an alkenyl group and may be interpreted as an alkenyl group in which an aryl group is substituted.
  • Examples of the group to which three substituents are connected include an aryl group substituted with a heteroaryl group substituted with an aryl group, an aryl group substituted with an aryl group substituted with a heteroaryl group, a heteroaryl group substituted with an aryl group substituted with a heteroaryl group, and the like.
  • substituted or unsubstituted in the present specification is deuterium; An alkyl group; Aralkyl group; Alkenyl groups; Aryl group; And it is substituted or unsubstituted with one or more groups selected from the group consisting of a heteroaryl group, or two or more groups selected from the group selected from the group is substituted or unsubstituted.
  • substituted or unsubstituted is deuterium; Aryl group; And it is substituted or unsubstituted with one or more groups selected from the group consisting of a heteroaryl group, or two or more groups selected from the group selected from the group is substituted or unsubstituted.
  • examples of the halogen group include a fluoro group, a chloro group, a bromo group or an iodo group.
  • the alkoxy group means a group in which an alkyl group is bonded to an oxygen atom, and the carbon number is not particularly limited, but is preferably 1 to 20. According to an exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 6 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, and the like.
  • the aryloxy group means a group in which an aryl group is bonded to an oxygen atom, and the carbon number is not particularly limited, but is preferably 6 to 30. According to an exemplary embodiment, the aryloxy group has 6 to 25 carbon atoms.
  • aryloxy group examples include phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethylphenoxy group, 2,4,6-trimethylphenoxy group, 3-biphenyloxy group, 1- Naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 2-anthracenyloxy group, 9-anthracenyloxy group, 1-phenanthrenyloxy group, 3-phenanthrenyloxy group, 9-phenanthrenyl jade There is a period.
  • the alkyl group means a straight or branched hydrocarbon group, and the carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl and neopentyl , tert-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, octyl, n-octyl, tert- Octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, is
  • the alkenyl group represents a straight-chain or pulverized unsaturated hydrocarbon group including a carbon-carbon double bond, and the carbon number is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to an exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. Specific examples include, but are not limited to, ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl, n-hexenyl.
  • the heteroaryl group is a ring group containing one or more of N, O and S as heteroatoms, and carbon number is not particularly limited, but is preferably 2 to 40 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heteroaryl group has 2 to 20 carbon atoms.
  • heteroaryl group examples include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, Triazinyl group, triazolyl group, acridinyl group, carbolinyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group , Pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, is
  • an aryl group means a substituted or unsubstituted monocyclic or polycyclic which is wholly or partially unsaturated.
  • carbon number is not specifically limited, It is preferable that it is C6-C60.
  • the aryl group has 6 to 40 carbon atoms.
  • the aryl group has 6 to 30 carbon atoms.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
  • the polycyclic aryl group is naphthyl group, anthracenyl group, phenanthrenyl group, peryllenyl group, fluoranthenyl group, triphenylenyl group, penalenyl group, pyrenyl group, tetrasenyl group, chrysenyl group, pentaxenyl group, Fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spiro 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.
  • substituted fluorenyl group , , , , , , And Etc., but is not limited thereto.
  • the aryl group described above may be applied to the aryl group in the aralkyl group and the aryloxy group.
  • An exemplary embodiment of the present invention provides a compound represented by Chemical Formula 1.
  • X1 and X2 are each N, and X3 is CH.
  • X1 and X3 are each N, and X2 is CH.
  • X2 and X3 are each N, and X1 is CH.
  • X1 to X3 are each N.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group unsubstituted or substituted with an aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; Or a terphenyl group unsubstituted or substituted with an aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Or a terphenyl group.
  • R is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms.
  • R is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 18 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.
  • R is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 13 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.
  • R is hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
  • R is hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.
  • Y is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms.
  • Y is hydrogen or deuterium.
  • n 0.
  • n 1
  • n is 2.
  • n 3.
  • m 0.
  • Chemical Formula 1 is represented by the following Chemical Formula 2.
  • Chemical Formula 1 is represented by the following Chemical Formula 3.
  • Chemical Formula 2 is represented by the following Chemical Formula 2-A.
  • X, X1 to X3, Ar1, Ar2, Y and m are as defined in formula (2),
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R1 and R2 are hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R1 and R2 are hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms.
  • R1 and R2 are hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 18 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.
  • R1 and R2 are hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 13 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.
  • R1 and R2 are hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
  • R1 and R2 are hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.
  • Chemical Formula 3 is represented by the following Chemical Formula 3-A.
  • X, X1 to X3, Ar1, Ar2, Y and m are as defined in formula (3),
  • R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms.
  • R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 18 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.
  • R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 13 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.
  • R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
  • R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.
  • the compound represented by Formula 2 is any one selected from the following structures.
  • the compound represented by Formula 3 is any one selected from the following structures.
  • Formula 1 is an example of a method of forming the compound of Formula 1, the synthesis method of Formula 1 is not limited to the general formula 1, it may be by a method known in the art.
  • the present specification provides an organic light emitting device including the compound represented by Chemical Formula 1.
  • An exemplary embodiment of the present specification provides an organic light emitting device including a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer is a compound represented by Chemical Formula 1 It provides an organic light emitting device comprising a.
  • the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention is a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport at the same time as an organic material layer It may have a structure including a layer to.
  • the organic material layer includes an electron injection layer; Electron transport layer; Or a layer for simultaneously injecting and transporting electrons, wherein the electron injection layer; Electron transport layer; Alternatively, the layer simultaneously performing electron injection and transport may include the compound represented by Chemical 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 content of the compound represented by Formula 1 is 30 to 100 parts by weight; 50 parts by weight to 100 parts by weight; Or 70 parts by weight to 100 parts by weight.
  • the thickness of the light emitting layer including the compound represented by Chemical Formula 1 is 20 nm to 60 nm, preferably 30 nm to 50 nm.
  • the light emitting layer including the compound of Formula 1 further includes a host.
  • the weight of the light emitting layer is 100 parts by weight
  • the sum of the weight part of the compound of Formula 1 and the weight part of the host is 50 parts by weight to 100 parts by weight; Or 70 parts by weight to 100 parts by weight.
  • the driving voltage, the light emitting efficiency and / or the lifespan characteristics of the device may be further improved, and in particular, the lifespan characteristics may be greatly improved.
  • a condensed aromatic ring derivative, a heterocyclic containing compound, etc. can be used as said host.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives and ladders. Type furan compounds, pyrimidine derivatives, and the like, but is not limited thereto.
  • the host may be a carbazole derivative.
  • the host may be represented by the following Formula (B).
  • Ar11 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar12 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or heteroaryl group,
  • L11 is a direct bond; A substituted or unsubstituted divalent aryl group; Or a substituted or unsubstituted divalent heteroaryl group,
  • n1 is an integer of 0 to 8
  • Ar12 is the same or different from each other.
  • Chemical Formula B is represented by the following Chemical Formula B-1.
  • Ar13 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar14 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • L12 is a direct bond; A substituted or unsubstituted divalent aryl group; Or a substituted or unsubstituted divalent heteroaryl group,
  • k and p are each independently an integer of 0 to 7,
  • Ar12 is the same as or different from each other,
  • Ar 14 is the same as or different from each other.
  • Ar11 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar11 is an aryl group unsubstituted or substituted with an aryl group or heteroaryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group or a heteroaryl group.
  • Ar11 is a phenyl group; Or a biphenyl group.
  • Ar13 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar13 is an aryl group which is unsubstituted or substituted with an aryl group or heteroaryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group or a heteroaryl group.
  • Ar13 is a phenyl group; Or a biphenyl group.
  • Ar12 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar12 is hydrogen; heavy hydrogen; An alkyl group; An aryl group unsubstituted or substituted with an aryl group or heteroaryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group or a heteroaryl group.
  • Ar12 is hydrogen; Methyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted carbazolyl group.
  • Ar12 is hydrogen; Methyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted carbazolyl group.
  • Ar12 is hydrogen; Or a carbazolyl group substituted with a phenyl group or a biphenyl group.
  • Ar14 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar14 is hydrogen; heavy hydrogen; An alkyl group; An aryl group unsubstituted or substituted with an aryl group or heteroaryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group or a heteroaryl group.
  • Ar14 is hydrogen; Methyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted carbazolyl group.
  • Ar14 is hydrogen
  • L11 is a direct bond; A substituted or unsubstituted divalent aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted divalent heteroaryl group having 2 to 20 carbon atoms.
  • L11 is a direct bond; Divalent aryl group unsubstituted or substituted with an aryl group; Or a divalent heteroaryl group unsubstituted or substituted with an aryl group.
  • L11 is a direct bond; Or a substituted or unsubstituted phenylene group.
  • L12 is a direct bond; A substituted or unsubstituted divalent aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted divalent heteroaryl group having 2 to 20 carbon atoms.
  • L12 is a direct bond; Divalent aryl group unsubstituted or substituted with an aryl group; Or a divalent heteroaryl group unsubstituted or substituted with an aryl group.
  • L12 is a direct bond; Or a substituted or unsubstituted phenylene group.
  • m1 is 1.
  • k 0.
  • p 0.
  • Chemical Formula B is any one selected from the following structures.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes a compound represented by Chemical Formula 1
  • the light emitting layer further includes a dopant.
  • the content of the dopant is 1 part by weight to 30 parts by weight.
  • the emission wavelength of the dopant may be green, red, blue, etc., but is not limited thereto.
  • the dopant may be a phosphorescent dopant or a fluorescent dopant.
  • the dopant may be an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, or the like, but is not limited thereto.
  • aromatic amine derivative pyrene, anthracene, chrysene, periplanthene and the like having an arylamine group may be used as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group.
  • the styrylamine compound a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used.
  • styrylamine compound examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • the metal complex may be an iridium complex, a platinum complex, or the like, but is not limited thereto.
  • the dopant is an iridium complex.
  • the organic material layer is a hole injection layer; Hole transport layer; Or a layer for simultaneously injecting and transporting holes, wherein the hole injecting layer; Hole transport layer; Alternatively, the layer for simultaneously injecting and transporting holes may include the compound represented by Chemical Formula 1.
  • the organic light emitting device may be an organic light emitting device having a normal structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • 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.
  • FIGS. 1 to 3 The structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3.
  • 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.
  • the compound of Formula 1 is included in the light emitting layer (3).
  • 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.
  • the compound of Formula 1 is included in the light emitting layer (7).
  • FIG. 3 shows a substrate 1, an anode 2, a hole injection layer 5, an electron blocking layer 9, a light emitting layer 7, an electron transport layer 8, an electron injection layer 10 and a cathode 4.
  • An example of the organic light emitting element made is shown.
  • the compound of Formula 1 is included in the light emitting layer (7).
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of Formula 1.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition PVD, physical vapor deposition
  • sputtering e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof on the substrate
  • It can be prepared by forming an anode, 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 then depositing a material that can be used as a cathode 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 of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material.
  • the manufacturing method is not limited thereto.
  • the compound of Formula 1 when the compound of Formula 1 is included in the organic material layer of one or more layers, other materials except for the compound of Formula 1 may be the same as or different from each other.
  • the organic light emitting device includes a plurality of organic material layers, the plurality of organic material layers may be formed of the same material or different materials.
  • the anode material it is usually preferable to use a material having a large work function 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); 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, and the like, but are not limited thereto.
  • the negative electrode material a material having a small work function is preferably used 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 layer is a layer for injecting holes received from the electrode into the adjacent layer.
  • the hole injection material has the ability to transport holes, has an effect of hole injection at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and transfers excitons generated from the light emitting layer to the electron injection layer or the electron injection material. It is preferable to use the compound which prevents and is excellent in thin film formation ability.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene Organic, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer for transporting holes injected from the hole injection layer to the light emitting layer.
  • 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.
  • Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a nonconjugated portion together.
  • the electron blocking layer is a layer for preventing excess electrons passing through the light emitting layer from moving toward the hole transport layer.
  • the electron blocking material is preferably a material having a lower Unoccupied Molecular Orbital (LUMO) level than the hole transport layer, and may be selected as an appropriate material in consideration of the energy level of the surrounding layer.
  • LUMO Unoccupied Molecular Orbital
  • an arylamine-based organic material may be used as the electron blocking layer, but is not limited thereto.
  • the light emitting layer is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and may include a light emitting material having good quantum efficiency with respect to fluorescence or phosphorescence.
  • Specific examples of the light emitting material include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the organic material layer may include two or more light emitting layers, and materials included in the two or more light emitting layers are the same as or different from each other.
  • the hole blocking layer serves to prevent holes from flowing into the cathode through the light emitting layer in the driving process of the organic light emitting device.
  • the hole blocking material it is preferable to use a material having a very high Occupied Molecular Orbital (HOMO) level.
  • the hole blocking material may be specifically TPBi, BCP, CBP, PBD, PTCBI, BPhen 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 the electrons to the light emitting layer.
  • 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. Examples of the electron transporting material include naphthalene derivatives; Triazine derivatives; Al complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired negative electrode material as used in the prior art.
  • the electron injection layer is a layer for injecting electrons received from the electrode into the light emitting layer.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, Moreover, it is preferable to use the compound excellent in the thin film formation ability.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzimidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like Derivatives thereof, metal complex compounds and nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • the electron injection layer further includes an n-type dopant.
  • the n-type dopant may be organic or inorganic.
  • the inorganic material may be an alkali metal such as Li, Na, K, Rb or Cs; Alkaline earth metals such as Be, Mg, Ca, Sr and Ba; Rare earth metals such as La, Ce, Pr, Nd, Sm, Eu, Tb, Th, Gd or Mn.
  • the n-type dopant is an organic material
  • the organic material may be an aliphatic hydrocarbon ring, a hetero ring or a condensed ring thereof.
  • the weight of the electron injection layer is 100 parts by weight, the content of the n-type dopant may be 0.01 parts by weight to 10 parts by weight.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • a glass substrate coated with a thickness of 130 nm of ITO (indium tin oxide) 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 following compound HAT-CN was thermally vacuum deposited to a thickness of 5 nm on the prepared ITO transparent electrode to form a hole injection layer.
  • the following compound HT-1 was thermally vacuum deposited to a thickness of 25 nm on the hole injection layer to form a hole transport layer.
  • the following compound HT-2 was vacuum deposited to a thickness of 5 nm on the hole transport layer to form an electron blocking layer.
  • Compound 1, the following compound YGH-1 and the following compound YGD-1 was vacuum deposited to a thickness of 40 nm at a weight ratio of 44:44:12 on the electron blocking layer to form a light emitting layer.
  • the following compound ET-1 was vacuum deposited to a thickness of 25 nm on the light emitting layer to form an electron transport layer, and the following compounds ET-2 and Li (lithium) were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to 10 nm.
  • An electron injection layer of thickness was formed.
  • Aluminum was deposited to a thickness of 100 nm on the electron injection layer to form a cathode.
  • the deposition rate of the organic material was maintained at 0.04 nm / sec to 0.07 nm / sec, and the aluminum was maintained at the deposition rate of 0.2 nm / sec, and the vacuum degree during deposition was 1 ⁇ 10 ⁇ 7 torr to 5 ⁇ 10 ⁇ . 6 torr was maintained.
  • Example 2 to 14 and Comparative Examples 1 to 6 was manufactured in the same manner as in Example 1, except that Compound 1 in Example 1 was used instead of Compound 1.
  • T 95 means a time required to reduce the luminance to 95% when the initial luminance at the current density of 20 mA / cm 2 is 100%.
  • Example 1 One 3.01 66.89 (0.459, 0.532) 156
  • Example 2 2 3.10 65.12 (0.460, 0.531) 172
  • Example 3 3 3.15 64.33 (0.461, 0.530) 168
  • Example 4 4 3.05 67.12 (0.458, 0.533) 165
  • Example 5 5 3.12 66.22 (0.459, 0.532) 159
  • Example 6 6 3.01 65.11 (0.459, 0.532) 172
  • Example 7 7 3.20 68.22 (0.458, 0.533)
  • Example 8 8 3.02 64.82 (0.459, 0.532) 145
  • Example 9 9 2.95 67.27 (0.460, 0.531) 153
  • Example 10 10 3.21 67.90 (0.459, 0.532) 157
  • Example 11 11 3.16 63.25 (0.460, 0.531) 192
  • Example 12 3.11 66.77 (0.459, 0.532) 176
  • Example 13 3.20 63.25 (0
  • the devices of Examples 1 to 14 had a lower voltage, higher efficiency, and particularly excellent life characteristics than the devices of Comparative Examples 1 to 6.
  • the compound according to the exemplary embodiment of the present invention is excellent in receiving electrons from the electron transport layer, thereby optimizing exciton formation in the light emitting layer, and as a result, it is possible to realize low voltage, high efficiency and long life characteristics of the device when included in the light emitting layer. have.

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Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et une diode électroluminescente organique le comprenant.
PCT/KR2019/003652 2018-03-28 2019-03-28 Composé et diode électroluminescente organique le comprenant WO2019190230A1 (fr)

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CN114075182B (zh) * 2021-09-23 2023-10-31 陕西莱特迈思光电材料有限公司 一种含氮化合物及使用其的有机电致发光器件和电子装置
KR102564921B1 (ko) * 2022-02-04 2023-08-09 엘티소재주식회사 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자 및 유기물층용 조성물
KR20240028926A (ko) 2022-08-25 2024-03-05 롬엔드하스전자재료코리아유한회사 복수 종의 호스트 재료, 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
US20240130230A1 (en) 2022-08-25 2024-04-18 Rohm And Haas Electronic Materials Korea Ltd. Plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same

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