WO2017052221A1 - Nouveau composé et élément électroluminescent organique comprenant celui-ci - Google Patents

Nouveau composé et élément électroluminescent organique comprenant celui-ci Download PDF

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WO2017052221A1
WO2017052221A1 PCT/KR2016/010574 KR2016010574W WO2017052221A1 WO 2017052221 A1 WO2017052221 A1 WO 2017052221A1 KR 2016010574 W KR2016010574 W KR 2016010574W WO 2017052221 A1 WO2017052221 A1 WO 2017052221A1
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이우철
홍완표
김연환
김형석
김동헌
김형철
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주식회사 엘지화학
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Priority to CN201680014648.1A priority Critical patent/CN107406350B/zh
Publication of WO2017052221A1 publication Critical patent/WO2017052221A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/08—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
    • C07C13/465—Indenes; Completely or partially hydrogenated indenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four 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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present specification relates to a novel compound 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 is often formed 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.
  • the present invention seeks to provide a compound having a low driving voltage and a long service life.
  • the present invention is to provide an organic light emitting device comprising the compound.
  • An exemplary embodiment of the present specification may provide a compound represented by the following Formula 1.
  • R 1 to R 4 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 substituted or unsubstituted (n + 2) is an aliphatic hydrocarbon group;
  • a substituted or unsubstituted (n + 2) is an aromatic hydrocarbon group;
  • substituted or unsubstituted (n + 2) is any one selected from the group consisting of heterocyclic groups,
  • R 5 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; And it is any one selected from the group consisting of a substituted or unsubstituted heterocyclic group,
  • Y is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heterocyclic group,
  • n is an integer from 1 to 4,
  • n 2 or more
  • the structures in parentheses are the same or different from each other.
  • an exemplary embodiment of the present specification 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. have.
  • the compound according to the exemplary embodiment of the present specification is used as a material of the organic material layer of the organic light emitting device, and may bring about an effect of improving efficiency of the organic light emitting device, low driving voltage and lifespan characteristics.
  • the compound according to one embodiment of the present specification may be used as a hole generation, hole transporting, hole buffer, hole generation and hole transporting or light emitting material.
  • FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, a first electrode 2, a hole transport layer 6, a light emitting layer 3, and a second electrode 4.
  • FIG. 2 shows an organic light emitting device comprising a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 8, and a second electrode 4. An example is shown.
  • An example of an organic light emitting device including two units including light emitting layers 3a and 3b and electron transport layers 8a and 8b, and a charge generating layer 9 provided between the units.
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • the term "substituted or unsubstituted” is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylamine group; Aralkyl amine groups; Arylamine group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl phosphine group, or substituted or unsubstituted two or more substituents of the substituents exemplified above.
  • 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.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the corresponding substituent is substituted, a substituent positioned closest to the corresponding substituent, or another substituent substituted on the atom substituted by the corresponding substituent.
  • 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.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is 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 specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl,
  • the alkenyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but 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.
  • examples of the arylamine group include substituted or unsubstituted monocyclic diarylamine groups, substituted or unsubstituted polycyclic diarylamine groups or substituted or unsubstituted monocyclic and polycyclic diaryls. It means an amine group.
  • 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 naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heterocyclic group is a heterocyclic group containing one or more of N, O, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carb
  • heterocycle is a divalent group.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • the aryloxy group, the arylthioxy group, the aryl sulfoxy group, the aryl phosphine group, the aralkyl group, the aralkylamine group, the aryl group in the aralkenyl group, the arylamine group, the description of the above-described aryl group can be applied.
  • an alkyl thioxy group, an alkyl sulfoxy group, an aralkyl group, an aralkyl amine group, and an alkyl group among the alkyl amine groups may be described with respect to the aforementioned alkyl group.
  • heteroaryl group the heteroaryl group of the heteroarylamine group, the description of the aforementioned heterocyclic group may be applied.
  • alkenyl group of the alkenyl group may be applied to the description of the alkenyl group described above.
  • heteroarylene is a divalent group.
  • the meaning of combining with adjacent groups to form a ring means combining with adjacent groups with each other for a substituted or unsubstituted aliphatic hydrocarbon ring; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Or to form a substituted or unsubstituted aromatic heterocycle.
  • the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic.
  • examples of the aromatic hydrocarbon ring include, but are not limited to, phenyl group, naphthyl group, anthracenyl group, and the like.
  • the aliphatic heterocycle means an aliphatic ring containing one or more of the heteroatoms.
  • the aromatic heterocycle means an aromatic ring including at least one of heteroatoms.
  • the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
  • R 1 to R 4 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; 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 aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 1 to R 4 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 1 to R 4 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 1 to R 4 may be each independently a substituted or unsubstituted aryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring.
  • R 1 to R 4 are each independently an aryl group unsubstituted or substituted with a halogen group or a nitrile group, or combine with an adjacent group to form a substituted or unsubstituted ring. Can be.
  • R 1 to R 4 are each independently an aryl group unsubstituted or substituted with a fluorine or nitrile group, or may combine with an adjacent group to form a substituted or unsubstituted ring. have.
  • R 1 to R 4 may be each independently an aryl group substituted with a fluorine or nitrile group, or may be bonded to adjacent groups to form a ring.
  • R 5 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted cycloalkyl group; And it is any one selected from the group consisting of a substituted or unsubstituted aryl group.
  • R 5 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; And it is any one selected from the group consisting of a substituted or unsubstituted aryl group.
  • R 5 is a halogen group; Nitrile group; And an aryl group unsubstituted or substituted with a halogen group or a nitrile group.
  • R 5 is a halogen group; Nitrile group; And an aryl group substituted with a halogen group or a nitrile group.
  • R 5 is a halogen group; Nitrile group; And an aryl group substituted with a fluorine or nitrile group.
  • Y is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heterocyclic group.
  • Y is hydrogen; Halogen group; Nitrile group; Substituted or unsubstituted alkyl group; And a substituted or unsubstituted aryl group.
  • Y is hydrogen; Halogen group; Nitrile group; And an aryl group unsubstituted or substituted with a halogen group or a nitrile group.
  • Y is hydrogen; Halogen group; Nitrile group; And an aryl group substituted with a halogen group or a nitrile group.
  • Y is hydrogen; Halogen group; Nitrile group; And an aryl group substituted with a fluorine or nitrile group.
  • Formula 1 may be a compound represented by Formula 2 or Formula 3.
  • R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
  • R 6 to R 8 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Carbonyl group; Ester group; Imide group; Amino 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 substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or un
  • R 6 to R 8 are each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylaryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 6 to R 8 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 alkylaryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 6 to R 8 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted cycloalkyl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 6 to R 8 are each independently a substituted or unsubstituted cycloalkyl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 6 to R 8 may be each independently a substituted or unsubstituted aryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring.
  • R 6 to R 8 are each independently an aryl group unsubstituted or substituted with a halogen group or a nitrile group, or combine with an adjacent group to form a substituted or unsubstituted ring. Can be.
  • R 6 to R 8 are each independently an aryl group unsubstituted or substituted with a fluorine or nitrile group, or may combine with an adjacent group to form a substituted or unsubstituted ring. have.
  • R 6 to R 8 may be each independently an aryl group substituted with a fluorine or nitrile group, or may be bonded to adjacent groups to form a ring.
  • Formula 1 may be a compound represented by the following formula (4) or (5).
  • R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
  • R 9 to R 12 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Carbonyl group; Ester group; Imide group; Amino 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 substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or un
  • R 9 to R 12 are each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylaryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 9 to R 12 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 alkylaryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 9 to R 12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted cycloalkyl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 9 to R 12 are each independently a substituted or unsubstituted cycloalkyl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 9 to R 12 are each independently a substituted or unsubstituted aryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring.
  • R 9 to R 12 are each independently an aryl group unsubstituted or substituted with a halogen group or a nitrile group, or combine with an adjacent group to form a substituted or unsubstituted ring. Can be.
  • R 9 to R 12 are each independently an aryl group unsubstituted or substituted with a fluorine or nitrile group, or may combine with an adjacent group to form a substituted or unsubstituted ring. have.
  • R 9 to R 12 are each independently an aryl group substituted with fluorine or a nitrile group, or may be bonded to adjacent groups to form a ring.
  • Formula 1 may be a compound represented by Formula 6, Formula 7, or Formula 8.
  • R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
  • R 13 to R 21 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Carbonyl group; Ester group; Imide group; Amino 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 substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or un
  • R 13 to R 21 are each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylaryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 13 to R 21 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 alkylaryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 13 to R 21 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted cycloalkyl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 13 to R 21 are each independently a substituted or unsubstituted cycloalkyl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 13 to R 21 may be each independently a substituted or unsubstituted aryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring.
  • R 13 to R 21 are each independently an aryl group unsubstituted or substituted with a halogen group or a nitrile group, or combine with an adjacent group to form a substituted or unsubstituted ring. Can be.
  • R 13 to R 21 are each independently an aryl group unsubstituted or substituted with a fluorine or nitrile group, or may combine with an adjacent group to form a substituted or unsubstituted ring. have.
  • R 13 to R 21 may be each independently an aryl group substituted with a fluorine or nitrile group, or may be bonded to an adjacent group to form a ring.
  • Formula 1 is a compound represented by the following formula (9) or formula (10):
  • R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
  • R 22 to R 27 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Carbonyl group; Ester group; Imide group; Amino 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 substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or un
  • R 22 to R 27 are each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylaryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 22 to R 27 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 alkylaryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 22 to R 27 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted cycloalkyl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 22 to R 27 are each independently a substituted or unsubstituted cycloalkyl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 22 to R 27 are each independently a substituted or unsubstituted aryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring.
  • R 22 to R 27 are each independently an aryl group unsubstituted or substituted with a halogen group or a nitrile group, or combine with an adjacent group to form a substituted or unsubstituted ring. Can be.
  • R 22 to R 27 are each independently an aryl group unsubstituted or substituted with a fluorine or nitrile group, or may combine with an adjacent group to form a substituted or unsubstituted ring. have.
  • R 22 to R 27 are each independently an aryl group substituted with a fluorine or nitrile group, or may be bonded to adjacent groups to form a ring.
  • L- (Y) n of Chemical Formula 1 may be represented by the following Chemical Formula 11.
  • R 28 to R 31 are each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylaryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 28 to R 31 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 alkylaryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 28 to R 31 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted cycloalkyl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 28 to R 31 are each independently a substituted or unsubstituted cycloalkyl group; And it may be any one selected from the group consisting of a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • R 28 to R 31 are each independently a substituted or unsubstituted aryl group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring.
  • R 28 to R 31 are each independently an aryl group unsubstituted or substituted with a halogen group or a nitrile group, or may combine with an adjacent group to form a substituted or unsubstituted ring. have.
  • R 28 to R 31 are each independently an aryl group unsubstituted or substituted with a fluorine or nitrile group, or may be bonded to an adjacent group to form a substituted or unsubstituted ring. .
  • R 28 to R 31 are each independently an aryl group substituted with a fluorine or nitrile group, or may be bonded to an adjacent group to form a ring.
  • L- (Y) n of Chemical Formula 1 may be represented by the following Chemical Formula 12 or the following Chemical Formula 13.
  • X 1 to X 4 are each independently NR 32 ; S; O; Or PR 32 , Y 1 to Y 5 are each independently S; Or O, and R 32 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; And it is any one selected from the group consisting of a substituted or unsubstituted heterocyclic group.
  • X 1 to X 4 are each independently NR 32 ; S; O; Or PR 32 , Y 1 to Y 5 are each independently S; Or O, and R 32 is hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; And it is any one selected from the group consisting of a substituted or unsubstituted cycloalkyl group.
  • X 1 to X 4 are each independently NR 32 ; S; O; Or PR 32 , Y 1 to Y 5 are each independently S; Or O, wherein R 32 is a substituted or unsubstituted alkyl group; And it is any one selected from the group consisting of a substituted or unsubstituted cycloalkyl group.
  • X 1 to X 4 are each independently NR 32 ; S; O; Or PR 32 , Y 1 to Y 5 are each independently S; Or O, and R 32 is a substituted or unsubstituted alkyl group.
  • X 1 to X 4 are each independently NR 32 ; S; O; Or PR 32 , Y 1 to Y 5 are each independently S; Or O, and R 32 is an alkyl group having 1 to 10 carbon atoms.
  • X 1 to X 4 are each independently NR 32 ; S; O; Or PR 32 , Y 1 to Y 5 are each independently S; Or O, and R 32 is an alkyl group having 1 to 2 carbon atoms.
  • the Y is a nitrile group; Barbiturate groups; Or a rhodanine group.
  • the compound represented by Formula 1 may be represented by any one of the following formula.
  • the compound represented by Formula 1 may be represented by any one of the following formula.
  • the 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. have.
  • 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 may have a structure including a hole generating layer, a hole transporting layer, a hole buffer layer, a light emitting layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a hole generating layer, a hole transporting layer, a hole buffer layer, or a layer for simultaneously generating and transporting holes, and the hole generating layer, the hole transporting layer, the hole buffer layer, or the hole generation and transporting.
  • the layer may include the compound of formula (1).
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the compound of Formula 1.
  • the organic light emitting diode may be an organic light emitting diode having a 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 organic material layer includes a light emitting layer
  • the light emitting layer may include a compound represented by the following Chemical Formula 1-A.
  • z 1 is an integer of 1 or more, and when z 1 is 2 or more, the structures in parentheses are the same as or different from each other,
  • Ar 100 is a substituted or unsubstituted monovalent or higher benzofluorene group; Substituted or unsubstituted monovalent or higher fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or more chrysene group,
  • L 100 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R 100 and R 101 each independently represent a substituted or unsubstituted aryl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with each other to form a substituted or unsubstituted ring.
  • the light emitting layer includes a compound represented by Formula 1-A as a dopant of the light emitting layer.
  • the L 100 is a direct bond.
  • z 1 is 2.
  • Ar 100 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl, or tert-butyl groups; Or a divalent chrysene group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl or tert-butyl groups.
  • Ar 100 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl or tert-butyl groups.
  • R 100 and R 101 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • R 100 and R 101 are each independently a deuterium, an alkyl group, a nitrile group, an aryl group, an alkylsilyl group, or an alkyl group having 6 to 60 carbon atoms unsubstituted or substituted with an alkyl germanium group; Or a heteroaryl group having 2 to 60 carbon atoms unsubstituted or substituted with deuterium, an alkyl group, a nitrile group, an aryl group, an alkylsilyl group, or an alkyl germanium group.
  • R 100 and R 101 are each independently substituted or unsubstituted with deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium groups
  • R 100 and R 101 are each independently substituted or unsubstituted with deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium groups Phenyl group; Biphenyl group unsubstituted or substituted with deuterium, methyl group, ethyl group, iso-propyl group, tert-butyl group, nitrile group, phenyl group, trimethylsilyl group or trimethylgermanium group; Terphenyl groups unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium groups; Or a dibenzofuran group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl, ter
  • R 100 and R 101 are each independently a phenyl group unsubstituted or substituted with a trimethylgermanium group.
  • Formula 1-A may be selected from the following compounds.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include a compound represented by the following Chemical Formula 1-B.
  • Ar 101 and Ar 102 each independently represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • L 101 and L 102 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • z 2 and z 3 are each independently an integer of 1 to 2, when z 2 and z 3 is 2, the substituents in parentheses are the same as or different from each other,
  • R 102 and R 103 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted silyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • z 4 and z 5 are each an integer of 0 to 4, and when z 4 and z 5 are 2 or more, the substituents in parentheses are the same as or different from each other.
  • the light emitting layer includes a compound represented by Formula 1-B as a host of the light emitting layer.
  • Ar 101 and Ar 102 are each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Ar 101 and Ar 102 are each independently an aryl group or an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with a heteroaryl group; Or a heteroaryl group having 2 to 60 carbon atoms unsubstituted or substituted with an aryl group or a heteroaryl group.
  • Ar 101 and Ar 102 are each independently a phenyl group unsubstituted or substituted with an aryl group or heteroaryl group; A biphenyl group unsubstituted or substituted with an aryl group or a heteroaryl group; A naphthyl group unsubstituted or substituted with an aryl group or a heteroaryl group; A thiophene group unsubstituted or substituted with an aryl group or a heteroaryl group; Naphthobenzofuran group unsubstituted or substituted with an aryl group or a heteroaryl group; Or an indolocarbazole group unsubstituted or substituted with an aryl group or a heteroaryl group.
  • the L 101 and L 102 are each independently a direct bond; Phenylene group; Or a naphthylene group.
  • Ar 101 is a 2-naphthyl group.
  • Ar 102 is a 2-naphthyl group.
  • L 101 is a direct bond.
  • L 102 is a direct bond.
  • z 2 is 1.
  • z 3 is 1.
  • R 102 is a methyl group.
  • R 103 is hydrogen
  • z 4 is 1.
  • Formula 1-B may be selected from the following compounds.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound represented by Chemical Formula 1-A as a dopant of the light emitting layer
  • the compound represented by Chemical Formula 1-B is a host of the light emitting layer.
  • the organic light emitting device of the present specification may have a laminated structure as follows, but is not particularly limited thereto.
  • FIGS. 1 and 2 For example, the structure of an organic light emitting diode according to one embodiment of the present specification is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, a first electrode 2, a hole transport layer 6, a light emitting layer 3, and a second electrode 4.
  • the compound may be included in the hole transport layer.
  • FIG. 2 shows an organic light emitting device comprising a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 8, and a second electrode 4.
  • a substrate 1 a first electrode 2
  • a hole injection layer 5 a hole transport layer 6
  • a light emitting layer 3 a light emitting layer 3
  • an electron transport layer 8 a second electrode 4.
  • the compound may be included in the hole injection layer or hole transport layer.
  • An example of an organic light emitting device including two units including light emitting layers 3a and 3b and electron transport layers 8a and 8b, and a charge generating layer 9 provided between the units.
  • the first electrode 2 is an electrode for injecting holes, and may be any one of indium tin oxide (ITO), indium zinc oxide (IZO), or zinc oxide (ZnO) having a high work function.
  • the first electrode 2 when the first electrode 2 is a reflective electrode, the first electrode 2 may include any one of aluminum (Al), silver (Ag), and nickel (Ni) under a layer made of any one of ITO, IZO, or ZnO. It may further include a reflective layer consisting of one.
  • the hole injection layer 5 may play a role of smoothly injecting holes from the first electrode 2 to the light emitting layer 3.
  • the hole injection layer 5 may include the compound of Formula 1.
  • the hole injection layer 5 may be made of only the compound of Formula 1, but the compound of Formula 1 may be present in a mixed or doped state with other hole injection layer materials known in the art.
  • the compound of Formula 1 may account for 100% of the hole injection layer, but may be doped with 0.1 to 50% by weight.
  • the compound of Formula 1 is a derivative having an indenofluorene structure, has excellent electron acceptability, and may improve power consumption and lower driving voltage.
  • the hole injection layer 5 may have a thickness of 1 to 150 nm.
  • the hole injection layer material hole injection materials known in the art may be used.
  • the hole injection layer material CuPc (cupper phthalocyanine), PEDOT (poly (3,4) -ethylenedioxythiophene), PANI (polyaniline) and NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine) Any one or more selected may be used, but is not limited thereto.
  • the hole transport layer 6 may serve to facilitate the transport of holes.
  • the hole transport layer 6 may include the compound of Formula 1.
  • the hole transport layer 6 may be made of only the compound of Formula 1, but the compound of Formula 1 may be present in a mixed or doped state with other hole transport layer materials known in the art.
  • the compound of Formula 1 may account for 100% of the hole transport layer, but may be doped with 0.1 to 50% by weight.
  • Other hole transport material may be a hole transport material known in the art.
  • the hole transport layer 6 may be NPD (N, N-dinaphthyl-N, N'-diphenylbenzidine), TPD (N, N'-bis- (3-methylphenyl) -N, N'-bis- (phenyl)- benzidine), s-TAD and MTDATA (4,4 ', 4 "-Tris (N-3-methylphenyl-N-phenyl-amino) -triphenylamine), but may be one or more selected from the group consisting of, but not limited to For example, as the hole transport layer material, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkaine derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino substituted chalcone derivatives, and oxazoles Derivatives, styryl anthracene derivatives, fluorenone derivatives, hydra
  • a hole buffer layer may be further provided between the hole injection layer and the hole transport layer.
  • the hole buffer layer may include the compound of Formula 1, and may include other hole injection or transport materials known in the art. Even when the hole buffer layer includes the compound of Formula 1, the hole buffer layer may also be formed of only the compound of Formula 1, but may be formed in a mixture or doped state of the compound of Formula 1 with another host material.
  • An electron suppression layer may be provided between the hole transport layer and the light emitting layer, and the compound of Formula 1 or a material known in the art may be used.
  • the emission layer 3 may emit red, green and / or blue, and may be made of a phosphor or a fluorescent material.
  • the light emitting layer material may use those known in the art.
  • Carbazole biphenyl (CBP) or mCP (1,3-bis (N-carbazol-9-yl) benzene) may be used as the light emitting host material, but is not limited thereto.
  • the light emitting dopants include PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonate iridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium) and PQIr (tris (1).
  • phosphorescent materials such as -phenylquinoline) iridium), octaethylporphyrin platinum (PtOEP), or fluorescent materials such as Alq 3 (tris (8-hydroxyquinolino) aluminum) may be used, but are not limited thereto.
  • the light emitting dopant may be a phosphor such as Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium) or a fluorescence such as Alq 3 (tris (8-hydroxyquinolino) aluminum). Materials can be used, but are not limited thereto.
  • a light emitting dopant may be a phosphor such as (4,6-F 2 ppy) 2 Irpic, but spiro-DPVBi, spiro-6P, ditylbenzene (DSB) or distriaryl Fluorescent materials such as ethylene (DSA), PFO-based polymers, and PPV-based polymers may be used, but are not limited thereto.
  • a hole suppression layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.
  • the electron transport layer 8 may play a role of smoothing the transport of electrons.
  • Materials known in the art such as Alq 3 (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq can be used.
  • the electron transport layer 8 may have a thickness of about 1 nm to about 50 nm.
  • the thickness of the electron transporting layer 8 is 1 nm or more, there is an advantage that the electron transporting property can be prevented from being lowered.
  • the thickness of the electron transporting layer 8 is 50 nm or less, the thickness of the electron transporting layer 8 is too thick to improve the movement of electrons. In order to prevent the driving voltage from rising, there is an advantage.
  • the electron injection layer may play a role of smoothly injecting electrons.
  • Alq 3 tris (8-hydroxyquinolino) aluminum
  • PBD tris (8-hydroxyquinolino) aluminum
  • TAZ spiro-PBD
  • BAlq or SAlq can be made of organic materials, complexes or metal compounds known in the art.
  • Metal compounds include metal halides, and storage can be used, for example, can be used LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF 2, MgF 2, CaF 2, SrF 2, BaF 2 and RaF 2 and the like.
  • the electron injection layer may have a thickness of about 1 nm to about 50 nm.
  • the thickness of the electron injection layer is 1 nm or more, there is an advantage that the electron injection characteristics may be prevented from being lowered.
  • the thickness of the electron injection layer is 50 nm or less, the thickness of the electron injection layer is too thick, so that the driving voltage is increased to improve the movement of electrons. There is an advantage that can be prevented from being raised.
  • the second electrode 4 is an electron injection electrode, and may be made of magnesium (Mg), calcium (Ca), aluminum (Al), silver (Ag), or an alloy thereof having a low work function.
  • the cathode 4 may be formed to a thickness thin enough to transmit light when the organic light emitting device is a front or double-sided light emitting structure, and may reflect light when the organic light emitting device is a rear light emitting structure. Can be formed thick enough.
  • 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 the present specification, that is, the compound of Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • 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 represented by Chemical Formula 1, that is, the compound represented by Chemical 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. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. And, by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • PVD physical vapor deposition
  • the compound 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 (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the first electrode may be a cathode
  • the second electrode may be an anode
  • the positive electrode material may be a material having a large work function to facilitate hole injection into the organic material layer.
  • Specific examples of 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); ZnO: Al or SnO 2 : Combination of metals and oxides such as 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 that can be used in the present invention 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 from an electrode.
  • the hole injection material has a capability of transporting holes to have a hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a light emitting material.
  • the compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer.
  • the hole transport material is a material that can transport holes from an anode or a hole injection layer and transfer them to the light emitting layer.
  • the material 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 light emitting material 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 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.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • 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.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof 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 electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or silver layer in each case.
  • the electron injection layer is a layer for injecting electrons from an electrode, has an 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 hole injection of excitons generated in the light emitting layer
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( 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.
  • the compound of Formula 1 may be prepared using materials and reaction conditions known in the art. For example, it may be prepared according to the following Schemes 1 to 24.
  • Scheme 1 exemplifies a process for preparing a compound of Formula 2, but based on this, the remaining compounds may also be prepared using reaction conditions or materials known in the art. Moreover, the kind and number of substituents of a compound can be changed as needed.
  • the compounds A-1, A-3, A-5, A-7, A-9, A-10, and A-11 which are examples of the present invention prepared in the above-described synthesis example, are respectively provided in the hole injection layer.
  • An embodiment in which an organic light emitting device is manufactured by doping is disclosed.
  • MADN, BD-A, Alq 3 and ⁇ -NPB are compounds represented by the following formulas, respectively.
  • the light emitting area of the ITO glass was patterned to have a size of 3 mm ⁇ 3 mm and then washed.
  • the base pressure was 1 ⁇ 10 ⁇ 6 torr, and then ⁇ -NPB (100 kPa) doped with the aforementioned compound A-1 (20 wt%) was formed on the anode ITO glass.
  • ⁇ -NPD was formed to a thickness of 600 kV with the hole transport layer
  • BD-A a dopant
  • Alq 3 was formed to a thickness of 300 kW with the electron transport layer.
  • LiF was formed to a thickness of 10 kPa as an electron injection layer
  • Al was sequentially formed to a thickness of 800 kPa as a cathode to fabricate an organic light emitting device.
  • the organic light emitting device was manufactured by using only the compound A-3, instead of the compound A-1, in the hole injection layer.
  • the organic light emitting device was manufactured by using only the compound A-5 doped into the hole injection layer instead of the compound A-1.
  • the organic light emitting device was manufactured by using only the compound A-7 doped into the hole injection layer instead of the compound A-1.
  • the organic light emitting device was manufactured by using only the compound A-9 instead of the compound A-1 in the hole injection layer.
  • the organic light emitting device was manufactured by using only the compound A-10 instead of the compound A-1 in the hole injection layer.
  • the organic light emitting device was manufactured by using only the compound A-11 instead of the compound A-1 in the hole injection layer.
  • the organic light emitting device was manufactured by using only the HAT-CN doped in the hole injection layer instead of the compound A-1.
  • the organic light emitting device was manufactured by using only 700 ⁇ of the hole injection layer without any doping.
  • the organic light emitting device was manufactured by differently doping the compound of the compound B-1 to the hole injection layer instead of the compound A-1.
  • the driving voltage, current efficiency, power efficiency, and luminance of the organic light emitting diodes manufactured in Examples 1 to 7 and Comparative Examples 1 to 3 are shown in Table 1 below.
  • the compounds A-1, A-3, A-5, A-10, A-11, and A-12 which are examples of the present invention prepared in the above-described synthesis examples, are used alone in the hole injection layer, respectively.
  • the Example which produced the organic light emitting element is described.
  • Ir (ppy) 3 , CBP, and BCP are compounds represented by the following formulas, respectively.
  • the light emitting area of the ITO glass was patterned to have a size of 3 mm ⁇ 3 mm and then washed.
  • the basic pressure was 1 ⁇ 10 ⁇ 6 torr, and then the organic material was formed on the anode ITO as a hole injection layer to form a compound A-1 with a thickness of 40 kPa, and the hole transport layer as ⁇ - NPD is formed to a thickness of 800 ⁇ , dopant Ir (ppy) 3 is doped with 10% by weight of dopant to CBP, a yellow light emitting layer, and formed to a thickness of 300 ⁇ .
  • An Alq 3 was formed to a thickness of 150 kV as an electron transporting layer, a LiF was formed to a thickness of 5 mW as an electron injection layer, and Al was sequentially formed to a thickness of 1000 mW as a cathode to fabricate an organic light emitting device.
  • the organic light emitting device was manufactured by using only the compound A-3 instead of the compound A-1 in the hole injection layer.
  • the organic light emitting device was manufactured by using only the compound A-5 instead of the compound A-1 in the hole injection layer.
  • the organic light emitting device was manufactured by using only the compound A-10 instead of the compound A-1 in the hole injection layer.
  • the organic light emitting device was manufactured by using only the compound A-11 instead of the compound A-1 in the hole injection layer.
  • the organic light emitting device was manufactured by using only the compound A-12 instead of the compound A-1 in the hole injection layer.
  • the organic light emitting device was manufactured by using only the HAT-CN instead of the compound A-1 in the hole injection layer.
  • the organic light emitting device was manufactured by changing only that the hole injection layer was not formed.
  • the organic light emitting device was manufactured by using only the compound of Compound B-1 in the hole injection layer instead of the compound A-1.
  • the driving voltage, current efficiency, power efficiency, and luminance of the organic light emitting diodes manufactured in Examples 8 to 13 and Comparative Examples 4 to 6 are shown in Table 2 below.

Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et un élément électroluminescent organique comprenant ledit composé. (Dans la formule, L représente l'un quelconque des éléments choisis dans le groupe comprenant C (si n = 2), CR5 (si n =1), N, un groupe hydrocarbure aliphatique de valence (n +2) substitué ou non, un groupe hydrocarbure aromatique de valence (n +2) substitué ou non, et un groupe hétérocyclique de valence (n +2) substitué ou non).
PCT/KR2016/010574 2015-09-22 2016-09-22 Nouveau composé et élément électroluminescent organique comprenant celui-ci WO2017052221A1 (fr)

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CN112552304B (zh) * 2019-09-26 2022-06-07 广州华睿光电材料有限公司 芳环并芘醌类化合物及其应用
CN112778081B (zh) * 2020-12-28 2022-11-25 上海和辉光电股份有限公司 一种用于有机发光的化合物及其应用

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