WO2017052221A1 - Novel compound and organic light-emitting element comprising same - Google Patents

Novel compound and organic light-emitting element comprising same 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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compound
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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/en
Publication of WO2017052221A1 publication Critical patent/WO2017052221A1/en

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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
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    • 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
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    • 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

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

The present invention provides a compound represented by chemical formula 1 and an organic light-emitting element comprising same.(Herein L is any one selected from the group consisting of C (if n=2), CR5 (if n=1), N, a substituted or unsubstituted (n+2)-valent aliphatic hydrocarbon group, a substituted or unsubstituted (n+2)-valent aromatic hydrocarbon group, and a substituted or unsubstituted (n+2)-valent heterocyclic group.)

Description

신규 화합물 및 이를 포함하는 유기 발광 소자New compound and organic light emitting device comprising the same
본 출원은 2015년 09월 22일 한국특허청에 제출된 한국 특허 출원 제10-2015-0133837호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2015-0133837 filed with the Korea Patent Office on September 22, 2015, the entire contents of which are incorporated herein.
본 명세서는 신규 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a novel compound and an organic light emitting device including the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, 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. In this case, 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. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.There is a continuing need for the development of new materials for such organic light emitting devices.
본 발명은 구동 전압이 낮고 수명이 긴 화합물을 제공하고자 한다.The present invention seeks to provide a compound having a low driving voltage and a long service life.
또한, 본 발명은 상기 화합물을 포함하는 유기 발광 소자를 제공하고자 한다.In addition, the present invention is to provide an organic light emitting device comprising the compound.
본 명세서의 일 실시상태는, 하기 화학식 1로 표시되는 화합물을 제공할 수 있다.An exemplary embodiment of the present specification may provide a compound represented by the following Formula 1.
[화학식 1][Formula 1]
Figure PCTKR2016010574-appb-I000001
Figure PCTKR2016010574-appb-I000001
상기 화학식 1에 있어서,In Chemical Formula 1,
R1 내지 R4는 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,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 substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may combine with an adjacent group to form a substituted or unsubstituted ring,
L은 C(n=2인 경우); CR5(n=1인 경우); N; 치환 또는 비치환된 (n+2)가 지방족 탄화수소기; 치환 또는 비치환된 (n+2)가 방향족 탄화수소기; 및 치환 또는 비치환된 (n+2)가 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이고,L is C (if n = 2); CR 5 (if n = 1); N; A substituted or unsubstituted (n + 2) is an aliphatic hydrocarbon group; A substituted or unsubstituted (n + 2) is an aromatic hydrocarbon group; And substituted or unsubstituted (n + 2) is any one selected from the group consisting of heterocyclic groups,
상기 R5는 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이고,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,
Y는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어지는 군에서 선택되고,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,
n은 1 내지 4의 정수이며,n is an integer from 1 to 4,
n이 2 이상인 경우, 괄호안의 구조는 서로 같거나 상이하다.When n is 2 or more, the structures in parentheses are the same or different from each other.
또한, 본 명세서의 일 실시상태는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1의 화합물을 포함하는 것인 유기 발광 소자를 제공할 수 있다.In addition, 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.
본 명세서의 일 실시상태에 의한 화합물은 유기 발광 소자의 유기물층의 재료로서 사용되어, 유기 발광 소자의 효율 향상, 낮은 구동전압 및 수명 특성의 향상 효과를 가져올 수 있다. 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.
또한, 본 명세서의 일 실시상태에 의한 화합물은 정공 생성, 정공 수송, 정공 버퍼, 정공 생성과 정공 수송 또는 발광 재료로 사용될 수 있다.In addition, 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.
도 1은 기판(1), 제1 전극(2), 정공 수송층(6), 발광층(3), 제2 전극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.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.
도 2는 기판(1), 제1 전극(2), 정공 주입층(5), 정공 수송층(6), 발광층(3), 전자 수송층(8) 및 제2 전극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.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.
도 3은 기판(1), 제1 전극(2) 및 제2 전극(4)을 포함하고, 제1 전극과 제2 전극 사이에, 정공 주입층(5a, 5b), 정공 수송층(6a, 6b), 발광층(3a, 3b) 및 전자 수송층(8a, 8b)를 포함하는 유닛을 2개 포함하고, 상기 유닛들 사이에 전하 생성층(9)이 구비된 유기 발광 소자의 예를 도시한 것이다.3 includes a substrate 1, a first electrode 2, and a second electrode 4, and hole injection layers 5a and 5b and hole transport layers 6a and 6b between the first and second electrodes. ), 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.
도 4는 합성예에서 제조된 화합물 A-9의 질량 스펙트럼을 나타낸 그래프이다.4 is a graph showing the mass spectrum of the compound A-9 prepared in the synthesis example.
도 5는 합성예에서 제조된 화합물 A-10의 질량 스펙트럼을 나타낸 그래프이다.5 is a graph showing the mass spectrum of the compound A-10 prepared in the synthesis example.
<도면 부호의 설명><Description of Drawing>
1: 기판1: substrate
2: 제1 전극2: first electrode
3, 3a, 3b: 발광층3, 3a, 3b: light emitting layer
4: 제2 전극4: second electrode
5, 5a, 5b: 정공 주입층5, 5a, 5b: hole injection layer
6, 6a, 6b: 정공 수송층6, 6a, 6b: hole transport layer
8, 8a, 8b: 전자 수송층8, 8a, 8b: electron transport layer
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, the present specification will be described in more detail.
본 명세서의 일 실시상태는 상기 화학식 1로 표시되는 화합물을 제공한다. An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the substituents are described below, but are not limited thereto.
본 명세서에서 "치환 또는 비치환된"이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 시클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아민기; 아랄킬아민기; 아릴아민기; 및 아릴포스핀기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, 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. For example, "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.
본 명세서에 있어서, "인접한"기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오쏘(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한"기로 해석될 수 있다.In this specification, the term "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. Can be. For example, 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.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.Although 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.
Figure PCTKR2016010574-appb-I000002
Figure PCTKR2016010574-appb-I000002
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, 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.
Figure PCTKR2016010574-appb-I000003
Figure PCTKR2016010574-appb-I000003
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, although 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.
Figure PCTKR2016010574-appb-I000004
Figure PCTKR2016010574-appb-I000004
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
본 명세서에 있어서, 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸부틸, 1-에틸부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸프로필, 1,1-디메틸프로필, 이소헥실, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, 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. Specific examples of the alkyl group 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, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.
본 명세서에 있어서, 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, 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.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸 등이 있으나, 이에 한정되지 않는다. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 단환식의 디아릴아민기, 치환 또는 비치환된 다환식의 디아릴아민기 또는 치환 또는 비치환된 단환식 및 다환식의 디아릴아민기를 의미한다.In the present specification, 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.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, 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.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2016010574-appb-I000005
,
Figure PCTKR2016010574-appb-I000006
,
Figure PCTKR2016010574-appb-I000007
및
Figure PCTKR2016010574-appb-I000008
등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2016010574-appb-I000005
,
Figure PCTKR2016010574-appb-I000006
,
Figure PCTKR2016010574-appb-I000007
And
Figure PCTKR2016010574-appb-I000008
And so on. However, the present invention is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 이종원자로 N, O, S, Si 및 Se 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, 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. Examples of 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, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), thiazolyl group, Isooxazolyl group, oxdiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group and the like, but is not limited thereto.
본 명세서에 있어서, 방향족 탄화수소고리는 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aforementioned aryl group may be applied except that the aromatic hydrocarbon ring is a divalent group.
본 명세서에 있어서, 헤테로고리는 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heterocycle is a divalent group.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.
본 명세서에 있어서, 아릴옥시기, 아릴티옥시기, 아릴술폭시기, 아릴포스핀기, 아르알킬기, 아랄킬아민기, 아르알케닐기, 아릴아민기 중의 아릴기는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, 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.
본 명세서에 있어서, 알킬티옥시기, 알킬술폭시기, 아르알킬기, 아랄킬아민기, 알킬아민기 중 알킬기는 전술한 알킬기에 관한 설명이 적용될 수 있다. In the present specification, 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.
본 명세서에 있어서, 헤테로아릴기, 헤테로아릴아민기 중 헤테로아릴기는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. In the present specification, the heteroaryl group, the heteroaryl group of the heteroarylamine group, the description of the aforementioned heterocyclic group may be applied.
본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기에 관한 설명이 적용될 수 있다. In the present specification, the alkenyl group of the alkenyl group may be applied to the description of the alkenyl group described above.
본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group.
본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
본 명세서에 있어서, 인접하는 기와 서로 결합하여 고리를 형성한다는 의미는 인접하는 기와 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 지방족 헤테로고리; 또는 치환 또는 비치환된 방향족 헤테로고리를 형성하는 것을 의미한다.In the present specification, 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.
본 명세서에 있어서, 지방족 탄화수소고리란 방향족이 아닌 고리로서 탄소와 수소 원자로만 이루어진 고리를 의미한다.In the present specification, the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic.
본 명세서에 있어서, 방향족 탄화수소고리의 예로는 페닐기, 나프틸기, 안트라세닐기 등이 있으나 이들에만 한정되는 것은 아니다.In the present specification, examples of the aromatic hydrocarbon ring include, but are not limited to, phenyl group, naphthyl group, anthracenyl group, and the like.
본 명세서에 있어서, 지방족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 지방족고리를 의미한다.In the present specification, the aliphatic heterocycle means an aliphatic ring containing one or more of the heteroatoms.
본 명세서에 있어서, 방향족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 방향족고리를 의미한다.In the present specification, the aromatic heterocycle means an aromatic ring including at least one of heteroatoms.
본 명세서에 있어서, 상기 지방족 탄화수소고리, 방향족 탄화수소고리, 지방족 헤테로고리 및 방향족 헤테로고리는 단환 또는 다환일 수 있다.In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
본 발명의 일 실시상태에 따르면, 상기 R1 내지 R4는 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.According to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R1 내지 R4는 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R1 내지 R4는 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R1 내지 R4는 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R1 내지 R4는 각각 독립적으로 할로겐기 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R1 내지 R4는 각각 독립적으로 불소 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R1 내지 R4는 각각 독립적으로 불소 또는 니트릴기로 치환된 아릴기이거나, 인접하는 기와 서로 결합하여 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 L은 C(n=2인 경우); CR5(n=1인 경우); N; 및 치환 또는 비치환된 (n+2)가 방향족 탄화수소기로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present invention, L is C (when n = 2); CR 5 (if n = 1); N; And substituted or unsubstituted (n + 2) is any one selected from the group consisting of aromatic hydrocarbon groups.
또한, 본 발명의 일 실시상태에 따르면, 상기 L은 C(n=2인 경우); CR5(n=1인 경우); N; 및 할로겐기 또는 니트릴기로 치환 또는 비치환된 (n+2)가 방향족 탄화수소기로 이루어진 군에서 선택되는 어느 하나이다.In addition, according to an exemplary embodiment of the present invention, L is C (when n = 2); CR 5 (if n = 1); N; And (n + 2) unsubstituted or substituted with a halogen group or a nitrile group is any one selected from the group consisting of aromatic hydrocarbon groups.
또한, 본 발명의 일 실시상태에 따르면, 상기 L은 C(n=2인 경우); CR5(n=1인 경우); N; 및 할로겐기 또는 니트릴기로 치환된 (n+2)가 방향족 탄화수소기로 이루어진 군에서 선택되는 어느 하나이다.In addition, according to an exemplary embodiment of the present invention, L is C (when n = 2); CR 5 (if n = 1); N; And (n + 2) substituted with a halogen group or a nitrile group is any one selected from the group consisting of aromatic hydrocarbon groups.
또한, 본 발명의 일 실시상태에 따르면, 상기 L은 C(n=2인 경우); CR5(n=1인 경우); N; 및불소 또는 니트릴기로 치환된 (n+2)가 방향족 탄화수소기로 이루어진 군에서 선택되는 어느 하나이다.In addition, according to an exemplary embodiment of the present invention, L is C (when n = 2); CR 5 (if n = 1); N; And (n + 2) substituted with a fluorine or nitrile group is any one selected from the group consisting of aromatic hydrocarbon groups.
본 발명의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 할로겐기; 니트릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R5는 할로겐기; 니트릴기; 및 할로겐기 또는 니트릴기로 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이다.In addition, according to an exemplary embodiment of the present invention, R 5 is a halogen group; Nitrile group; And an aryl group unsubstituted or substituted with a halogen group or a nitrile group.
또한, 본 발명의 일 실시상태에 따르면, 상기 R5는 할로겐기; 니트릴기; 및 할로겐기 또는 니트릴기로 치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이다.In addition, according to an exemplary embodiment of the present invention, R 5 is a halogen group; Nitrile group; And an aryl group substituted with a halogen group or a nitrile group.
또한, 본 발명의 일 실시상태에 따르면, 상기 R5는 할로겐기; 니트릴기; 및 불소 또는 니트릴기로 치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이다.In addition, according to an exemplary embodiment of the present invention, R 5 is a halogen group; Nitrile group; And an aryl group substituted with a fluorine or nitrile group.
본 발명의 일 실시상태에 따르면, Y는 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어지는 군에서 선택된다.According to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, Y는 수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 및 치환 또는 비치환된 아릴기로 이루어지는 군에서 선택된다.In addition, according to an exemplary embodiment of the present invention, Y is hydrogen; Halogen group; Nitrile group; Substituted or unsubstituted alkyl group; And a substituted or unsubstituted aryl group.
또한, 본 발명의 일 실시상태에 따르면, Y는 수소; 할로겐기; 니트릴기; 및 할로겐기 또는 니트릴기로 치환 또는 비치환된 아릴기로 이루어지는 군에서 선택된다.In addition, according to an exemplary embodiment of the present invention, Y is hydrogen; Halogen group; Nitrile group; And an aryl group unsubstituted or substituted with a halogen group or a nitrile group.
또한, 본 발명의 일 실시상태에 따르면, Y는 수소; 할로겐기; 니트릴기; 및 할로겐기 또는 니트릴기로 치환된 아릴기로 이루어지는 군에서 선택된다.In addition, according to an exemplary embodiment of the present invention, Y is hydrogen; Halogen group; Nitrile group; And an aryl group substituted with a halogen group or a nitrile group.
또한, 본 발명의 일 실시상태에 따르면, Y는 수소; 할로겐기; 니트릴기; 및 불소 또는 니트릴기로 치환된 아릴기로 이루어지는 군에서 선택된다.In addition, according to an exemplary embodiment of the present invention, Y is hydrogen; Halogen group; Nitrile group; And an aryl group substituted with a fluorine or nitrile group.
본 발명의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 2 또는 하기 화학식 3으로 표시되는 화합물일 수 있다.According to an exemplary embodiment of the present invention, Formula 1 may be a compound represented by Formula 2 or Formula 3.
[화학식 2][Formula 2]
Figure PCTKR2016010574-appb-I000009
Figure PCTKR2016010574-appb-I000009
[화학식 3][Formula 3]
Figure PCTKR2016010574-appb-I000010
Figure PCTKR2016010574-appb-I000010
상기 화학식 2 및 3에 있어서,In Chemical Formulas 2 and 3,
R1, R4, L, Y 및 n은 상기 화학식 1에서 정의한 바와 같고,R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
R6 내지 R8은 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고, a 및 b는 각각 1 내지 5의 정수이고, c는 1 내지 4의 정수이며, a, b 및 c가 각각 2 이상인 경우, 괄호안의 구조는 서로 같거나 상이하다.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 unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may combine with adjacent groups to form a substituted or unsubstituted ring, a and b are each an integer of 1 to 5, c is When an integer is 1 to 4 and a, b, and c are each 2 or more, the structures in parentheses are the same or different from each other.
또한, 본 발명의 일 실시상태에 따르면, 상기 R6 내지 R8은 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R6 내지 R8은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R6 내지 R8은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R6 내지 R8은 각각 독립적으로 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R6 내지 R8은 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R6 내지 R8은 각각 독립적으로 할로겐기 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R6 내지 R8은 각각 독립적으로 불소 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R6 내지 R8은 각각 독립적으로 불소 또는 니트릴기로 치환된 아릴기이거나, 인접하는 기와 서로 결합하여 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 4 또는 하기 화학식 5로 표시되는 화합물일 수 있다.According to an exemplary embodiment of the present invention, Formula 1 may be a compound represented by the following formula (4) or (5).
[화학식 4][Formula 4]
Figure PCTKR2016010574-appb-I000011
Figure PCTKR2016010574-appb-I000011
[화학식 5][Formula 5]
Figure PCTKR2016010574-appb-I000012
Figure PCTKR2016010574-appb-I000012
상기 화학식 4 및 5에 있어서,In Chemical Formulas 4 and 5,
R1, R4, L, Y 및 n은 상기 화학식 1에서 정의한 바와 같고,R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
R9 내지 R12는 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고, d 및 e는 각각 1 내지 3의 정수이며, f 및 g는 각각 1 내지 4의 정수이며, d, e, f 및 g가 각각 2 이상인 경우, 괄호안의 구조는 서로 같거나 상이하다.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 unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may combine with adjacent groups to form a substituted or unsubstituted ring, d and e are each an integer of 1 to 3, f and g is an integer of 1-4, respectively, and when d, e, f, and g are each 2 or more, the structure in parentheses is same or different from each other.
또한, 본 발명의 일 실시상태에 따르면, 상기 R9 내지 R12는 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R9 내지 R12는 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R9 내지 R12는 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R9 내지 R12는 각각 독립적으로 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R9 내지 R12는 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R9 내지 R12는 각각 독립적으로 할로겐기 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R9 내지 R12는 각각 독립적으로 불소 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R9 내지 R12는 각각 독립적으로 불소 또는 니트릴기로 치환된 아릴기이거나, 인접하는 기와 서로 결합하여 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 6, 하기 화학식 7 또는 하기 화학식 8로 표시되는 화합물일 수 있다.According to an exemplary embodiment of the present invention, Formula 1 may be a compound represented by Formula 6, Formula 7, or Formula 8.
[화학식 6][Formula 6]
Figure PCTKR2016010574-appb-I000013
Figure PCTKR2016010574-appb-I000013
[화학식 7][Formula 7]
Figure PCTKR2016010574-appb-I000014
Figure PCTKR2016010574-appb-I000014
[화학식 8][Formula 8]
Figure PCTKR2016010574-appb-I000015
Figure PCTKR2016010574-appb-I000015
상기 화학식 6 내지 8에 있어서,In Chemical Formulas 6 to 8,
R1, R4, L, Y 및 n은 상기 화학식 1에서 정의한 바와 같고,R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
R13 내지 R21은 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고, h 내지 j는 각각 1 또는 2이며, k 및 o는 각각 1 내지 3의 정수이며, l 및 p는 각각 1 내지 3의 정수이며, h, i, j, k, o, l 및 p가 각각 2 이상인 경우, 괄호안의 구조는 서로 같거나 상이하다.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 unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may combine with adjacent groups to form a substituted or unsubstituted ring, h to j is 1 or 2, respectively, k and o are Each is an integer of 1 to 3, l and p are each an integer of 1 to 3, and when h, i, j, k, o, l and p are each 2 or more, the structures in parentheses are the same or different from each other.
또한, 본 발명의 일 실시상태에 따르면, 상기 R13 내지 R21은 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R13 내지 R21은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R13 내지 R21은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R13 내지 R21은 각각 독립적으로 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R13 내지 R21은 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R13 내지 R21은 각각 독립적으로 할로겐기 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R13 내지 R21은 각각 독립적으로 불소 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R13 내지 R21은 각각 독립적으로 불소 또는 니트릴기로 치환된 아릴기이거나, 인접하는 기와 서로 결합하여 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 9 또는 하기 화학식 10으로 표시되는 화합물:According to an exemplary embodiment of the present invention, Formula 1 is a compound represented by the following formula (9) or formula (10):
[화학식 9][Formula 9]
Figure PCTKR2016010574-appb-I000016
Figure PCTKR2016010574-appb-I000016
[화학식 10][Formula 10]
Figure PCTKR2016010574-appb-I000017
Figure PCTKR2016010574-appb-I000017
상기 화학식 9 및 10에 있어서,In Chemical Formulas 9 and 10,
R1, R4, L, Y 및 n은 상기 화학식 1에서 정의한 바와 같고,R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
R22 내지 R27은 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고, r 내지 u는 각각 1 내지 3의 정수이며, v는 1 또는 2이고, r 내지 u 및 v가 각각 2 이상인 경우, 괄호안의 구조는 서로 같거나 상이하다.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 unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may combine with adjacent groups to form a substituted or unsubstituted ring, r to u are each an integer of 1 to 3, v is When 1 or 2 and r to u and v are each 2 or more, the structures in parentheses are the same or different from each other.
또한, 본 발명의 일 실시상태에 따르면, 상기 R22 내지 R27은 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R22 내지 R27은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R22 내지 R27은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R22 내지 R27은 각각 독립적으로 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R22 내지 R27은 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R22 내지 R27은 각각 독립적으로 할로겐기 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.Further, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R22 내지 R27은 각각 독립적으로 불소 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R22 내지 R27은 각각 독립적으로 불소 또는 니트릴기로 치환된 아릴기이거나, 인접하는 기와 서로 결합하여 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 =L-(Y)n은 하기 화학식 11로 표시될 수 있다.According to an exemplary embodiment of the present invention, = L- (Y) n of Chemical Formula 1 may be represented by the following Chemical Formula 11.
[화학식 11][Formula 11]
Figure PCTKR2016010574-appb-I000018
Figure PCTKR2016010574-appb-I000018
상기 화학식 11에 있어서, In Chemical Formula 11,
R28 내지 R31은 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.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.
또한, 본 발명의 일 실시상태에 따르면, 상기 R28 내지 R31은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, R28 내지 R31은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, R28 내지 R31은 각각 독립적으로 치환 또는 비치환된 시클로알킬기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, R28 내지 R31은 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, R28 내지 R31은 각각 독립적으로 할로겐기 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, R28 내지 R31은 각각 독립적으로 불소 또는 니트릴기로 치환 또는 비치환된 아릴기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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. .
또한, 본 발명의 일 실시상태에 따르면, R28 내지 R31은 각각 독립적으로 불소 또는 니트릴기로 치환된 아릴기이거나, 인접하는 기와 서로 결합하여 고리를 형성할 수 있다.In addition, according to an exemplary embodiment of the present invention, 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.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 =L-(Y)n은 하기 화학식 12 또는 하기 화학식 13으로 표시될 수 있다.According to an exemplary embodiment of the present specification, = L- (Y) n of Chemical Formula 1 may be represented by the following Chemical Formula 12 or the following Chemical Formula 13.
[화학식 12][Formula 12]
Figure PCTKR2016010574-appb-I000019
Figure PCTKR2016010574-appb-I000019
[화학식 13][Formula 13]
Figure PCTKR2016010574-appb-I000020
Figure PCTKR2016010574-appb-I000020
상기 화학식 12 및 13에 있어서,In Chemical Formulas 12 and 13,
X1 내지 X4는 각각 독립적으로 NR32; S; O; 또는 PR32이며, Y1 내지 Y5는 각각 독립적으로 S; 또는 O이고, 상기 R32는 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이다.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.
또한, 본 발명의 일 실시상태에 따르면, X1 내지 X4는 각각 독립적으로 NR32; S; O; 또는 PR32이며, Y1 내지 Y5는 각각 독립적으로 S; 또는 O이고, 상기 R32는 수소; 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 및 치환 또는 비치환된 시클로알킬기로 이루어진 군에서 선택되는 어느 하나이다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, X1 내지 X4는 각각 독립적으로 NR32; S; O; 또는 PR32이며, Y1 내지 Y5는 각각 독립적으로 S; 또는 O이고, 상기 R32는 치환 또는 비치환된 알킬기; 및 치환 또는 비치환된 시클로알킬기로 이루어진 군에서 선택되는 어느 하나이다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, X1 내지 X4는 각각 독립적으로 NR32; S; O; 또는 PR32이며, Y1 내지 Y5는 각각 독립적으로 S; 또는 O이고, 상기 R32는 치환 또는 비치환된 알킬기이다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, X1 내지 X4는 각각 독립적으로 NR32; S; O; 또는 PR32이며, Y1 내지 Y5는 각각 독립적으로 S; 또는 O이고, 상기 R32는 탄소수 1 내지 10의 알킬기이다.In addition, according to an exemplary embodiment of the present invention, 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.
또한, 본 발명의 일 실시상태에 따르면, X1 내지 X4는 각각 독립적으로 NR32; S; O; 또는 PR32이며, Y1 내지 Y5는 각각 독립적으로 S; 또는 O이고, 상기 R32는 탄소수 1 내지 2의 알킬기이다.In addition, according to an exemplary embodiment of the present invention, 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.
본 명세서의 일 실시상태에 따르면, 상기 Y는 니트릴기; 바르비투레이트기; 또는 로다닌기일 수 있다.According to an exemplary embodiment of the present specification, the Y is a nitrile group; Barbiturate groups; Or a rhodanine group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 하기 화학식 중 어느 하나로 표시될 수 있다.According to an exemplary embodiment of the present specification, the compound represented by Formula 1 may be represented by any one of the following formula.
Figure PCTKR2016010574-appb-I000021
Figure PCTKR2016010574-appb-I000021
Figure PCTKR2016010574-appb-I000022
Figure PCTKR2016010574-appb-I000022
Figure PCTKR2016010574-appb-I000023
Figure PCTKR2016010574-appb-I000023
Figure PCTKR2016010574-appb-I000024
Figure PCTKR2016010574-appb-I000024
Figure PCTKR2016010574-appb-I000025
Figure PCTKR2016010574-appb-I000025
Figure PCTKR2016010574-appb-I000026
Figure PCTKR2016010574-appb-I000026
Figure PCTKR2016010574-appb-I000027
Figure PCTKR2016010574-appb-I000027
Figure PCTKR2016010574-appb-I000028
Figure PCTKR2016010574-appb-I000028
Figure PCTKR2016010574-appb-I000029
Figure PCTKR2016010574-appb-I000029
Figure PCTKR2016010574-appb-I000030
Figure PCTKR2016010574-appb-I000030
Figure PCTKR2016010574-appb-I000031
Figure PCTKR2016010574-appb-I000031
Figure PCTKR2016010574-appb-I000032
Figure PCTKR2016010574-appb-I000032
Figure PCTKR2016010574-appb-I000033
Figure PCTKR2016010574-appb-I000033
Figure PCTKR2016010574-appb-I000034
Figure PCTKR2016010574-appb-I000034
Figure PCTKR2016010574-appb-I000035
Figure PCTKR2016010574-appb-I000035
Figure PCTKR2016010574-appb-I000036
Figure PCTKR2016010574-appb-I000036
Figure PCTKR2016010574-appb-I000037
Figure PCTKR2016010574-appb-I000037
Figure PCTKR2016010574-appb-I000038
Figure PCTKR2016010574-appb-I000038
Figure PCTKR2016010574-appb-I000039
Figure PCTKR2016010574-appb-I000039
Figure PCTKR2016010574-appb-I000040
Figure PCTKR2016010574-appb-I000040
Figure PCTKR2016010574-appb-I000041
Figure PCTKR2016010574-appb-I000041
본 명세서의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 하기 화학식 중 어느 하나로 표시될 수 있다.According to an exemplary embodiment of the present specification, the compound represented by Formula 1 may be represented by any one of the following formula.
Figure PCTKR2016010574-appb-I000042
Figure PCTKR2016010574-appb-I000042
본 명세서의 일 실시상태에 따르면, 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1의 화합물을 포함하는 것인 유기 발광 소자를 제공할 수 있다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공 생성층, 정공 수송층, 정공 버퍼층, 발광층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.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. For example, 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. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공 생성층, 정공 수송층, 정공 버퍼층 또는 정공 생성과 수송을 동시에 하는 층을 포함하고, 상기 정공 생성층, 정공 수송층, 정공 버퍼층 또는 정공 생성과 수송을 동시에 하는 층은 상기 화학식 1의 화합물을 포함할 수 있다. According to the exemplary embodiment of the present specification, 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. At the same time the layer may include the compound of formula (1).
또 하나의 실시상태에 따르면, 상기 유기물층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1의 화합물을 포함할 수 있다. According to another exemplary embodiment, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound of Formula 1.
또 하나의 실시상태에 따르면, 유기 발광 소자는 기판상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. According to another exemplary embodiment, 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.
또 하나의 실시상태에 따르면, 유기 발광 소자는 기판상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. According to another exemplary embodiment, 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.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 1-A로 표시되는 화합물을 포함할 수 있다.According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by the following Chemical Formula 1-A.
[화학식 1-A][Formula 1-A]
Figure PCTKR2016010574-appb-I000043
Figure PCTKR2016010574-appb-I000043
상기 화학식 1-A에 있어서,In Chemical Formula 1-A,
z1은 1 이상의 정수이고, z1이 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하고,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,
Ar100은 치환 또는 비치환된 1가 이상의 벤조플루오렌기; 치환 또는 비치환된 1가 이상의 플루오란텐기; 치환 또는 비치환된 1가 이상의 파이렌기; 또는 치환 또는 비치환된 1가 이상의 크리센기이고,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,
L100은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L 100 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R100 및 R101은 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴알킬기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다. 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.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 상기 화학식 1-A로 표시되는 화합물을 발광층의 도펀트로서 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes a compound represented by Formula 1-A as a dopant of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 L100은 직접결합이다.According to an exemplary embodiment of the present disclosure, the L 100 is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 z1은 2 이다.According to an exemplary embodiment of the present specification, z 1 is 2.
본 명세서의 일 실시상태에 따르면, 상기 Ar100은 중수소, 메틸기, 에틸기, iso-프로필기 또는 tert-부틸기로 치환 또는 비치환된 2가의 파이렌기; 또는 중수소, 메틸기, 에틸기, iso-프로필기 또는 tert-부틸기로 치환 또는 비치환된 2가의 크리센기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar100은 중수소, 메틸기, 에틸기, iso-프로필기 또는 tert-부틸기로 치환 또는 비치환된 2가의 파이렌기다.According to an exemplary embodiment of the present specification, Ar 100 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl or tert-butyl groups.
본 명세서의 일 실시상태에 따르면, 상기 R100 및 R101은 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 R100 및 R101은 각각 독립적으로 중수소, 알킬기, 니트릴기, 아릴기, 알킬실릴기, 또는 알킬게르마늄기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 중수소, 알킬기, 니트릴기, 아릴기, 알킬실릴기 또는 알킬게르마늄기로 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 R100 및 R101은 각각 독립적으로 중수소, 메틸기, 에틸기, iso-프로필기, tert-부틸기, 니트릴기, 페닐기, 트리메틸실릴기 또는 트리메틸게르마늄기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 중수소, 메틸기, 에틸기, iso-프로필기, tert-부틸기, 니트릴기, 페닐기, 트리메틸실릴기 또는 트리메틸게르마늄기로 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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 Aryl group having 6 to 60 ring carbon atoms; Or a heteroaryl group having 2 to 60 carbon atoms unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium groups.
본 명세서의 일 실시상태에 따르면, 상기 R100 및 R101은 각각 독립적으로 중수소, 메틸기, 에틸기, iso-프로필기, tert-부틸기, 니트릴기, 페닐기, 트리메틸실릴기 또는 트리메틸게르마늄기로 치환 또는 비치환된 페닐기; 중수소, 메틸기, 에틸기, iso-프로필기, tert-부틸기, 니트릴기, 페닐기, 트리메틸실릴기 또는 트리메틸게르마늄기로 치환 또는 비치환된 비페닐기; 중수소, 메틸기, 에틸기, iso-프로필기, tert-부틸기, 니트릴기, 페닐기, 트리메틸실릴기 또는 트리메틸게르마늄기로 치환 또는 비치환된 터페닐기; 또는 중수소, 메틸기, 에틸기, iso-프로필기, tert-부틸기, 니트릴기, 페닐기, 트리메틸실릴기 또는 트리메틸게르마늄기로 치환 또는 비치환된 디벤조퓨란기이다.According to an exemplary embodiment of the present specification, 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, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium groups.
본 명세서의 일 실시상태에 따르면, 상기 R100 및 R101은 각각 독립적으로 트리메틸게르마늄기로 치환 또는 비치환된 페닐기이다.According to an exemplary embodiment of the present specification, R 100 and R 101 are each independently a phenyl group unsubstituted or substituted with a trimethylgermanium group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1-A는 하기 화합물들 중에서 선택될 수 있다.According to an exemplary embodiment of the present specification, Formula 1-A may be selected from the following compounds.
Figure PCTKR2016010574-appb-I000044
Figure PCTKR2016010574-appb-I000044
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 1-B로 표시되는 화합물을 포함할 수 있다.According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by the following Chemical Formula 1-B.
[화학식 1-B][Formula 1-B]
Figure PCTKR2016010574-appb-I000045
Figure PCTKR2016010574-appb-I000045
상기 화학식 1-B에 있어서,In Chemical Formula 1-B,
Ar101 및 Ar102는 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,Ar 101 and Ar 102 each independently represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L101 및 L102는 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L 101 and L 102 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
z2 및 z3은 각각 독립적으로 1 내지 2의 정수이고, z2 및 z3이 2인 경우 괄호 안의 치환기는 서로 같거나 상이하고,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,
R102 및 R103은 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,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,
z4 및 z5는 각각 0 내지 4의 정수이고, z4 및 z5가 2 이상인 경우 괄호 안의 치환기는 서로 같거나 상이하다.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.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 상기 화학식 1-B로 표시되는 화합물을 발광층의 호스트로서 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes a compound represented by Formula 1-B as a host of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 Ar101 및 Ar102는 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar101 및 Ar102는 각각 독립적으로 아릴기 또는 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 아릴기 또는 헤테로아릴기로 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 Ar101 및 Ar102는 각각 독립적으로 아릴기 또는 헤테로아릴기로 치환 또는 비치환된 페닐기; 아릴기 또는 헤테로아릴기로 치환 또는 비치환된 비페닐기; 아릴기 또는 헤테로아릴기로 치환 또는 비치환된 나프틸기; 아릴기 또는 헤테로아릴기로 치환 또는 비치환된 티오펜기; 아릴기 또는 헤테로아릴기로 치환 또는 비치환된 나프토벤조퓨란기; 또는 아릴기 또는 헤테로아릴기로 치환 또는 비치환된 인돌로카바졸기이다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 L101 및 L102는 각각 독립적으로 직접결합; 페닐렌기; 또는 나프틸렌기이다.According to an exemplary embodiment of the present specification, the L 101 and L 102 are each independently a direct bond; Phenylene group; Or a naphthylene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar101은 2-나프틸기이다.According to an exemplary embodiment of the present specification, Ar 101 is a 2-naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar102는 2-나프틸기이다.According to an exemplary embodiment of the present specification, Ar 102 is a 2-naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L101은 직접결합이다.According to an exemplary embodiment of the present specification, L 101 is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 L102는 직접결합이다.According to an exemplary embodiment of the present specification, L 102 is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 z2는 1 이다.According to an exemplary embodiment of the present specification, z 2 is 1.
본 명세서의 일 실시상태에 따르면, 상기 z3은 1 이다.According to an exemplary embodiment of the present specification, z 3 is 1.
본 명세서의 일 실시상태에 따르면, 상기 R102는 메틸기이다.According to an exemplary embodiment of the present specification, R 102 is a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 R103은 수소이다.According to an exemplary embodiment of the present specification, R 103 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 z4는 1 이다.According to an exemplary embodiment of the present specification, z 4 is 1.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1-B는 하기 화합물들 중에서 선택될 수 있다.According to an exemplary embodiment of the present specification, Formula 1-B may be selected from the following compounds.
Figure PCTKR2016010574-appb-I000046
Figure PCTKR2016010574-appb-I000046
Figure PCTKR2016010574-appb-I000047
Figure PCTKR2016010574-appb-I000047
Figure PCTKR2016010574-appb-I000048
Figure PCTKR2016010574-appb-I000048
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1-A로 표시되는 화합물을 발광층의 도펀트로서 포함하며, 상기 화학식 1-B로 표시되는 화합물을 발광층의 호스트로서 포함한다.According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1-A as a dopant of the light emitting layer, and the compound represented by Chemical Formula 1-B is a host of the light emitting layer. Include as.
본 명세서의 유기 발광 소자는 하기와 같은 적층 구조를 가질 수 있으나, 특별히 이에 제한되는 것은 아니다.The organic light emitting device of the present specification may have a laminated structure as follows, but is not particularly limited thereto.
(1) 제1 전극/정공수송층/발광층/제2 전극(1) First electrode / hole transport layer / light emitting layer / second electrode
(2) 제1 전극/정공주입층/정공수송층/발광층/제2 전극(2) First electrode / hole injection layer / hole transport layer / light emitting layer / second electrode
(3) 제1 전극/정공주입층/정공버퍼층/정공수송층/발광층/제2 전극(3) First electrode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / second electrode
(4) 제1 전극/정공수송층/발광층/전자수송층/제2 전극(4) First electrode / hole transport layer / light emitting layer / electron transport layer / second electrode
(5) 제1 전극/정공수송층/발광층/전자수송층/전자주입층/제2 전극(5) First electrode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode
(6) 제1 전극/정공주입층/정공수송층/발광층/전자수송층/제2 전극(6) First electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / second electrode
(7) 제1 전극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/제2 전극(7) First electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode
(8) 제1 전극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/제2 전극(8) First electrode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / second electrode
(9) 제1 전극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/전자주입층 /제2 전극(9) First electrode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode
(10) 제1 전극/정공수송층/전자억제층/발광층/전자수송층/제2 전극(10) first electrode / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / second electrode
(11) 제1 전극/정공수송층/전자억제층/발광층/전자수송층/전자주입층/제2 전극(11) First electrode / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / electron injection layer / second electrode
(12) 제1 전극/정공주입층/정공수송층/전자억제층/발광층/전자수송층/제2 전극(12) First electrode / hole injection layer / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / second electrode
(13) 제1 전극/정공주입층/정공수송층/전자억제층/발광층/전자수송층/전자주입 층/제2 전극(13) First electrode / hole injection layer / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / electron injection layer / second electrode
(14) 제1 전극/정공수송층/발광층/정공억제층/전자수송층/제2 전극(14) First electrode / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / second electrode
(15) 제1 전극/정공수송층/발광층/정공억제층/전자수송층/전자주입층/제2 전극(15) First electrode / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / electron injection layer / second electrode
(16) 제1 전극/정공주입층/정공수송층/발광층/정공억제층/전자수송층/제2 전극(16) First electrode / hole injection layer / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / second electrode
(17) 제1 전극/정공주입층/정공수송층/발광층/정공억제층/전자수송층/전자주입 층/제2 전극(17) First electrode / hole injection layer / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / electron injection layer / second electrode
예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다. 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.
도 1은 기판(1), 제1 전극(2), 정공 수송층(6), 발광층(3), 제2 전극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화합물은 상기 정공 수송층에 포함될 수 있다. 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. In such a structure, the compound may be included in the hole transport layer.
도 2는 기판(1), 제1 전극(2), 정공 주입층(5), 정공 수송층(6), 발광층(3), 전자 수송층(8) 및 제2 전극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화합물은 상기 정공 주입층 또는 정공 수송층에 포함될 수 있다. 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. In such a structure, the compound may be included in the hole injection layer or hole transport layer.
도 3은 기판(1), 제1 전극(2) 및 제2 전극(4)을 포함하고, 제1 전극과 제2 전극 사이에, 정공 주입층(5a, 5b), 정공 수송층(6a, 6b), 발광층(3a, 3b) 및 전자 수송층(8a, 8b)를 포함하는 유닛을 2개 포함하고, 상기 유닛들 사이에 전하 생성층(9)이 구비된 유기 발광 소자의 예를 도시한 것이다.3 includes a substrate 1, a first electrode 2, and a second electrode 4, and hole injection layers 5a and 5b and hole transport layers 6a and 6b between the first and second electrodes. ), 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.
제1 전극(2)은 정공을 주입하는 전극으로 일함수가 높은 ITO(Indium Tin Oxide), IZO(Indium Zinc Oxide) 또는 ZnO(Zinc Oxide) 중 어느 하나일 수 있다. 또한, 상기 제1 전극(2)이 반사 전극일 경우에 제1 전극(2)은 ITO, IZO 또는 ZnO 중 어느 하나로 이루어진 층 하부에 알루미늄(Al), 은(Ag) 및 니켈(Ni) 중 어느 하나로 이루어진 반사층을 더 포함할 수 있다.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. In addition, 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.
정공 주입층(5)은 제1 전극(2)으로부터 발광층(3)으로 정공의 주입을 원활하게 하는 역할을 할 수 있다. 정공 주입층(5)은 상기 화학식 1의 화합물을 포함할 수 있다. 이 경우, 정공 주입층(5)은 상기 화학식 1의 화합물만으로 이루어질 수도 있으나, 상기 화학식 1의 화합물은 당 기술분야에 알려져 있는 다른 정공 주입층 재료에 혼합 또는 도핑된 상태로 존재할 수 있다. 상기 화학식 1의 화합물은 정공 주입층의 100%를 차지할 수도 있으나, 0.1 내지 50 중량%로 도핑될 수도 있다. 상기 화학식 1의 화합물은 인데노플루오렌 구조를 갖는 유도체로, 전자 수용 능력이 뛰어나, 소비전력을 개선하고 구동 전압을 낮출 수 있다. 정공 주입층(5)의 두께는 1 내지 150nm일 수 있다. 여기서, 상기 정공 주입층(5)의 두께가 1nm 이상이면, 정공 주입 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 150nm 이하이면, 정공 주입층(5)의 두께가 너무 두꺼워 정공의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다. 그외 정공 주입층 재료로는 당 기술분야에 알려져 있는 정공 주입 재료를 사용할 수 있다. 예컨대, 정공 주입층 재료로서 CuPc(cupper phthalocyanine), PEDOT(poly(3,4)-ethylenedioxythiophene), PANI(polyaniline) 및 NPD(N,N-dinaphthyl-N,N'-diphenyl benzidine)로 이루어진 군에서 선택된 어느 하나 이상이 사용될 수 있으나, 이에 한정되는 것은 아니다.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. In this case, 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. Here, when the thickness of the hole injection layer 5 is 1 nm or more, there is an advantage that the hole injection characteristics can be prevented from deteriorating. When the thickness of the hole injection layer 5 is too thick, the hole injection layer 5 is too thick to move the holes. There is an advantage that can be prevented from increasing the driving voltage to improve. As the hole injection layer material, hole injection materials known in the art may be used. For example, as 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.
정공 수송층(6)은 정공의 수송을 원활하게 하는 역할을 할 수 있다. 정공 수송층(6)은 상기 화학식 1의 화합물을 포함할 수 있다. 이 경우, 정공 수송층(6)은 상기 화학식 1의 화합물만으로 이루어질 수도 있으나, 상기 화학식 1의 화합물은 당 기술분야에 알려져 있는 다른 정공 수송층 재료에 혼합 또는 도핑된 상태로 존재할 수 있다. 상기 화학식 1의 화합물은 정공 수송층의 100%를 차지할 수도 있으나, 0.1 내지 50 중량%로 도핑될 수도 있다. 그외 정공 수송층 재료로는 당 기술분야에 알려져 있는 정공 수송 재료를 사용할 수 있다. 예컨대, 정공 수송층(6)은 NPD(N,N-dinaphthyl-N,N'-diphenylbenzidine), TPD(N,N'-bis-(3-methylphenyl)-N,N'-bis-(phenyl)-benzidine), s-TAD 및 MTDATA(4,4',4"- Tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine)로 이루어진 군에서 선택된 어느 하나 이상으로 이루어질 수 있으나 이에 한정되지 않는다. 예컨대 정공 수송층 재료로서 트라이아졸 유도체, 옥사다이아졸 유도체, 이미다졸 유도체, 폴리아릴알케인 유도체, 피라졸린 유도체 및 피라졸론 유도체, 페닐렌다이아민 유도체, 아릴아민 유도체, 아미노 치환 칼콘 유도체, 옥사졸 유도체, 스타이릴안트라센 유도체, 플루오렌온 유도체, 하이드라존 유도체, 스틸벤 유도체, 실라제인 유도체, 폴리실레인계, 아닐린계 공중합체, 도전성 고분자 올리고머(특히 싸이오펜 올리고머) 등을 들 수 있다.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. In this case, 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. For example, 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, hydrazone derivatives, stilbene derivatives, silazane derivatives, polysilane-based, aniline-based copolymers, conductive polymer oligomers (particularly thiophene oligomers) and the like.
정공 주입층과 정공 수송층 사이에 추가로 정공 버퍼층이 구비될 수 있다. 정공 버퍼층는 상기 화학식 1의 화합물을 포함할 수 있고, 그외 당 기술분야에 알려져 있는 정공 주입 또는 수송 재료를 포함될 수 있다. 정공 버퍼층이 상기 화학식 1의 화합물을 포함하는 경우에도 역시, 상기 화학식 1의 화합물만으로 이루어질 수도 있으나, 다른 호스트 물질에 상기 화학식 1의 화합물이 혼합 또는 도핑된 상태로 이루어질 수도 있다. 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.
정공 수송층과 발광층 사이에 전자 억제층이 구비될 수 있으며, 상기 화학식 1의 화합물 또는 당 기술분야에 알려져 있는 재료가 사용될 수 있다. 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.
상기 발광층(3)은 적색, 녹색 및/또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 발광층 재료는 당 기술분야에 공지된 것들을 사용할 수 있다. 발광 호스트 재료로는 CBP(carbazole biphenyl) 또는 mCP(1,3-bis(N-carbazol-9-yl)benzene) 이 사용될 수 있으나, 이에만 한정된 것은 아니다.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.
발광층(3)이 적색 발광을 하는 경우, 발광 도펀트로는 PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum)와 같은 인광 물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층(3)이 녹색 발광을 하는 경우, 발광 도펀트로는 Ir(ppy)3(fac tris(2-phenylpyridine)iridium)와 같은 인광 물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층(3)이 청색 발광을 하는 경우, 발광 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), PFO계 고분자, PPV계 고분자와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. When the light emitting layer 3 emits red light, 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. When the light emitting layer 3 emits green light, 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. When the light emitting layer 3 emits blue light, 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.
전자 수송층과 발광층 사이에 정공 억제층이 구비될 수 있으며, 당 기술분야에 알려져 있는 재료가 사용될 수 있다. 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.
전자 수송층(8)은 전자의 수송을 원활하게 하는 역할을 할 수 있다. Alq3(tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq와 같은 당 기술분야에 알려진 재료가 사용될 수 있다. 상기 전자 수송층(8)의 두께는 1 내지 50nm일 수 있다. 여기서, 상기 전자 수송층(8)의 두께가 1nm 이상이면, 전자 수송 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 50nm 이하이면, 전자 수송층(8)의 두께가 너무 두꺼워 전자의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.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. Here, when 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. When 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.
상기 전자 주입층은 전자의 주입을 원활하게 하는 역할을 할 수 있다. Alq3(tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq 또는 SAlq과 같은 당 기술분야에 알려져 있는 유기물이나 착체 또는 금속화합물로 이루어질 수 있다. 금속화합물로는 금속 할로겐화물이 사용될 수 있으며, 예컨대 LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF2, MgF2, CaF2, SrF2, BaF2 및 RaF2 등이 사용될 수 있다. 상기 전자주입층의 두께는 1 내지 50nm일 수 있다. 여기서, 상기 전자 주입층의 두께가 1nm 이상이면, 전자 주입 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 50nm 이하이면, 전자 주입층의 두께가 너무 두꺼워 전자의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.The electron injection layer may play a role of smoothly injecting electrons. Alq 3 (tris (8-hydroxyquinolino) aluminum), PBD, 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. Here, when 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. When 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.
상기 제2 전극(4)은 전자 주입 전극으로, 일함수가 낮은 마그네슘(Mg), 칼슘(Ca), 알루미늄(Al), 은(Ag) 또는 이들의 합금으로 이루어질 수 있다. 여기서, 음극(4)은 유기 발광 소자가 전면 또는 양면발광구조일 경우, 빛을 투과할 수 있을 정도로 얇은 두께로 형성할 수 있으며, 유기 발광 소자가 배면발광구조일 경우, 빛을 반사시킬 수 있을 정도로 두껍게 형성할 수 있다. 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. Here, 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.
본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 본 명세서의 화합물, 즉 상기 화학식 1의 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.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.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 상기 화학식 1의 화합물, 즉 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.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.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(Physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, 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.
또한, 상기 화학식 1의 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, 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. Here, 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.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다 (국제 특허 출원 공개 제 2003/012890호). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to such a method, 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). However, the manufacturing method is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극일 수 있다. According to an exemplary embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.
또 하나의 실시상태에 따르면, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극일 수 있다. According to another exemplary embodiment, the first electrode may be a cathode, and the second electrode may be an anode.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질일 수 있다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 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.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 본 발명에서 사용될 수 있는 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of 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.
상기 정공 주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자 주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 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. Specific examples of the hole injection material 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.
상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. 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.
상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. 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.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. 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. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, 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. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As 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. In particular, examples of 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.
상기 전자 주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. 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. Specifically, 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.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.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.
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 기술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, the present invention will be described in detail with reference to Examples. However, the embodiments according to the present disclosure may be modified in various other forms, and the scope of the present specification is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.
상기 화학식 1의 화합물은 당 기술분야에 알려져 있는 재료와 반응 조건을 이용하여 제조될 수 있다. 예컨대, 하기 반응식 1 내지 24에 따라 제조될 수 있다.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.
[반응식 1] Scheme 1
Figure PCTKR2016010574-appb-I000049
Figure PCTKR2016010574-appb-I000049
상기 반응식 1은 화학식 2의 화합물을 제조하는 과정을 예시한 것이나, 이를 기초로, 나머지 화합물들도 당 기술분야에 알려져 있는 반응 조건이나 재료를 이용하여 제조할 수 있다. 또한, 필요에 따라 화합물의 치환기의 종류나 개수를 변경할 수 있다. 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.
<< 합성예Synthesis Example >>
<중간체 A의 합성>Synthesis of Intermediate A
[반응식 2] Scheme 2
Figure PCTKR2016010574-appb-I000050
Figure PCTKR2016010574-appb-I000050
1,2-비스(4-플루오르페닐)에탄-1,2-다이온 10.0g과 1,3-비스(4-플루오르페닐)프로판-2-온 10.1g을 메탄올 200 ml에 녹이고, 질소 조건에서 4시간 환류 교반을 행했다. 냉각 후, 반응액을 여과하고, 물, 메탄올로 세정하고, 추가로 아세토나이트릴로 슬러리 정제하여 검은색 고체인 중간체 A (7.0g)를 얻었다. 얻어진 검은색 고체의 질량 스펙트럼 측정에 의해 M/Z=456에서 피크가 확인되었다. 10.0 g of 1,2-bis (4-fluorophenyl) ethane-1,2-dione and 10.1 g of 1,3-bis (4-fluorophenyl) propan-2-one are dissolved in 200 ml of methanol, and Reflux stirring was performed for 4 hours. After cooling, the reaction solution was filtered, washed with water and methanol, and further purified by slurry with acetonitrile to obtain an intermediate A (7.0 g) as a black solid. The peak was confirmed by M / Z = 456 by mass spectrum measurement of the obtained black solid.
<화합물 A-1의 합성><Synthesis of Compound A-1>
[반응식 3] Scheme 3
Figure PCTKR2016010574-appb-I000051
Figure PCTKR2016010574-appb-I000051
500ml 2구 플라스크에 중간체 A (7.0g), 말라노니트릴(malononitrile)(6.1g)를 넣고 디클로로메탄 250ml로 녹인 후, 티타늄(Ⅳ)클로라이드(Titanium(Ⅳ)chloride) (13.5 ml)와 피리딘 (Pyridine)(20.0ml)를 0℃에서 차례대로 15분간 적가한다. 그 후, 질소조건에서 3시간 동안 실온 교반시켰다. 그 후, 디클로로메탄을 감압증류하여 제거하고, 1% 묽은 염산과 클로로포름으로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 클로로포름을 감압증류한 후, 메틸렌 클로라이드, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 A-1 (5.8g)을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=504에서 피크가 확인되었다.Intermediate A (7.0 g), malononitrile (6.1 g) was added to a 500 ml two-necked flask, and dissolved in 250 ml of dichloromethane. Then, titanium (IV) chloride (13.5 ml) and pyridine ( Pyridine) (20.0 ml) was added dropwise at 0 ° C. over 15 minutes. Thereafter, the mixture was stirred at room temperature for 3 hours under nitrogen conditions. Thereafter, dichloromethane was removed by distillation under reduced pressure, and the mixture was worked up with 1% dilute hydrochloric acid and chloroform, dried over anhydrous sodium sulfate and filtered. Chloroform was distilled under reduced pressure, and then separated by methylene chloride, n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain compound A-1 (5.8 g). The peak was confirmed by M / Z = 504 by the mass spectrum measurement of the obtained solid.
<화합물 A-2의 합성><Synthesis of Compound A-2>
[반응식 4] Scheme 4
Figure PCTKR2016010574-appb-I000052
Figure PCTKR2016010574-appb-I000052
중간체 A 4.0g을 디클로로메탄 200ml에 교반, 용해시켰다. 플라스크 내를 질소 분위기로 하고, 용액 온도를 -10℃ 이하로 냉각하였다. 그 용액에 사염화타이타늄 3.2mL을 가하고, 그 후, 비스트라이메틸실릴 카보다이이미드 16.4g과 디클로로메탄 80ml의 혼합액을 적하했다. 적하 종료 후, 1시간 냉각을 계속한 후, 4시간 실온에서 교반하고, 추가로 2시간 환류 교반했다. 석출된 고체를 여과하고, 메탄올로 세정하여 화합물 A-2 (2.4g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=408에서 피크가 확인되었다.4.0 g of intermediate A was stirred and dissolved in 200 ml of dichloromethane. The flask was placed in a nitrogen atmosphere, and the solution temperature was cooled to -10 deg. Titanium tetrachloride 3.2mL was added to this solution, and the liquid mixture of 16.4 g of bistrimethylsilyl carbodiimide and 80 ml of dichloromethanes was dripped thereafter. After completion of the dropwise addition, cooling was continued for 1 hour, followed by stirring at room temperature for 4 hours, and further refluxing stirring for 2 hours. The precipitated solid was filtered and washed with methanol to obtain compound A-2 (2.4 g). The peak was confirmed at M / Z = 408 by mass spectrum measurement of the obtained solid.
<중간체 B의 합성>Synthesis of Intermediate B
[반응식 5] Scheme 5
Figure PCTKR2016010574-appb-I000053
Figure PCTKR2016010574-appb-I000053
1,2-비스(4-브로모페닐)에탄-1,2-다이온 14.9g과 1,3-비스(4-플루오르페닐)프로판-2-온 10.1g을 메탄올 300 ml에 녹이고, 질소 조건에서 4시간 환류 교반을 행했다. 냉각 후, 반응액을 여과하고, 물, 메탄올로 세정하고, 추가로 아세토나이트릴로 슬러리 정제하여 검은색 고체를 9.0g 얻었다. 다음으로, 아르곤조건에서 상기에서 얻은 고체 9.0g에 시안화구리 (CuCN) 2.9g을 첨가하고 N-메틸-2-피롤리디논 (N-methyl-2-pyrrolidinone) (100mL) 을 투입하여 교반하였다. 그 후 180℃까지 가열하여 24시간 교반하였다. 실온으로 냉각한 후 디에틸에테르 (400mL)와 암모니아수로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 디에틸에테르를 감압증류한 후, 에틸아세테이트, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 중간체 B (5.2g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=470에서 피크가 확인되었다.14.9 g of 1,2-bis (4-bromophenyl) ethane-1,2-dione and 10.1 g of 1,3-bis (4-fluorophenyl) propan-2-one are dissolved in 300 ml of methanol and subjected to nitrogen conditions. Reflux stirring was performed for 4 hours. After cooling, the reaction solution was filtered, washed with water and methanol, and further purified by slurry with acetonitrile to obtain 9.0 g of a black solid. Next, 2.9 g of copper cyanide (CuCN) was added to 9.0 g of the solid obtained above under argon conditions, and N-methyl-2-pyrrolidinone (100 mL) was added and stirred. Then, it heated to 180 degreeC and stirred for 24 hours. After cooling to room temperature, the mixture was worked up with diethyl ether (400 mL) and ammonia water, dried over anhydrous sodium sulfate, and filtered. The diethyl ether was distilled under reduced pressure, and then column separation was performed using ethyl acetate and n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain intermediate B (5.2 g). The peak was confirmed by M / Z = 470 by mass spectrum measurement of the obtained solid.
<화합물 A-3의 합성>Synthesis of Compound A-3
[반응식 6] Scheme 6
Figure PCTKR2016010574-appb-I000054
Figure PCTKR2016010574-appb-I000054
500ml 2구 플라스크에 중간체 B (7.2g), 말라노니트릴(malononitrile)(6.1g)를 넣고 디클로로메탄 300ml로 녹인 후, 티타늄(Ⅳ)클로라이드(Titanium(Ⅳ)chloride) (13.5 ml)와 피리딘 (Pyridine)(20.0ml)를 0℃에서 차례대로 15분간 적가한다. 그 후, 질소조건에서 4시간 동안 실온 교반시켰다. 그 후, 디클로로메탄을 감압증류하여 제거하고, 1% 묽은 염산과 클로로포름으로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 클로로포름을 감압증류한 후, 메틸렌 클로라이드, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 A-3 (4.8g)을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=519에서 피크가 확인되었다.Intermediate B (7.2 g), malononitrile (6.1 g) was added to a 500 ml two-necked flask, and dissolved in 300 ml of dichloromethane. Then, titanium (IV) chloride (13.5 ml) and pyridine ( Pyridine) (20.0 ml) was added dropwise at 0 ° C. over 15 minutes. Thereafter, the mixture was stirred at room temperature for 4 hours under nitrogen conditions. Thereafter, dichloromethane was removed by distillation under reduced pressure, and the mixture was worked up with 1% dilute hydrochloric acid and chloroform, dried over anhydrous sodium sulfate and filtered. Chloroform was distilled under reduced pressure, and then separated by methylene chloride, n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain a compound A-3 (4.8 g). The peak was confirmed by M / Z = 519 by mass spectrum measurement of the obtained solid.
<화합물 A-4의 합성><Synthesis of Compound A-4>
[반응식 7]Scheme 7
Figure PCTKR2016010574-appb-I000055
Figure PCTKR2016010574-appb-I000055
중간체 B (4.1g)를 디클로로메탄 200ml에 교반, 용해시켰다. 플라스크 내를 질소 분위기로 하고, 용액 온도를 -10℃ 이하로 냉각하였다. 그 용액에 사염화타이타늄 3.2mL을 가하고, 그 후, 비스트라이메틸실릴 카보다이이미드 16.4g과 디클로로메탄 80ml의 혼합액을 적하했다. 적하 종료 후, 1시간 냉각을 계속한 후, 4시간 실온에서 교반하고, 추가로 2시간 환류 교반했다. 석출된 고체를 여과하고, 메탄올로 세정하여 화합물 A-4 (2.0g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=495에서 피크가 확인되었다.Intermediate B (4.1 g) was stirred and dissolved in 200 ml of dichloromethane. The flask was placed in a nitrogen atmosphere, and the solution temperature was cooled to -10 deg. Titanium tetrachloride 3.2mL was added to this solution, and the liquid mixture of 16.4 g of bistrimethylsilyl carbodiimide and 80 ml of dichloromethanes was dripped thereafter. After completion of the dropwise addition, cooling was continued for 1 hour, followed by stirring at room temperature for 4 hours, and further refluxing stirring for 2 hours. The precipitated solid was filtered and washed with methanol to obtain compound A-4 (2.0 g). The peak was confirmed by M / Z = 495 by mass spectrum measurement of the obtained solid.
<중간체 C의 합성>Synthesis of Intermediate C
[반응식 8] Scheme 8
Figure PCTKR2016010574-appb-I000056
Figure PCTKR2016010574-appb-I000056
1,2-비스(4-브로모페닐)에탄-1,2-다이온 14.9g과 1,3-비스(4-브로모페닐)프로판-2-온 15.1g을 메탄올 300 ml에 녹이고, 질소 조건에서 4시간 환류 교반을 행했다. 냉각 후, 반응액을 여과하고, 물, 메탄올로 세정하고, 추가로 아세토나이트릴로 슬러리 정제하여 검은색 고체를 9.4g 얻었다. 다음으로, 아르곤조건에서 상기에서 얻은 고체 9.4g에 시안화구리 (CuCN) 5.3g을 첨가하고 N-메틸-2-피롤리디논 (N-methyl-2-pyrrolidinone) (100mL) 을 투입하여 교반하였다. 그후 180℃까지 가열하여 24시간 교반하였다. 실온으로 냉각한 후 디에틸에테르 (400mL)와 암모니아수로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 디에틸에테르를 감압증류한 후, 에틸아세테이트, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 중간체 C (4.2g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=485에서 피크가 확인되었다.14.9 g of 1,2-bis (4-bromophenyl) ethane-1,2-dione and 15.1 g of 1,3-bis (4-bromophenyl) propan-2-one were dissolved in 300 ml of methanol, followed by nitrogen. Reflux stirring was performed on conditions for 4 hours. After cooling, the reaction solution was filtered, washed with water and methanol, and further purified by slurry with acetonitrile to obtain 9.4 g of a black solid. Next, 5.3 g of copper cyanide (CuCN) was added to 9.4 g of the solid obtained above under argon conditions, and N-methyl-2-pyrrolidinone (100 mL) was added and stirred. Then, it heated to 180 degreeC and stirred for 24 hours. After cooling to room temperature, the mixture was worked up with diethyl ether (400 mL) and ammonia water, dried over anhydrous sodium sulfate, and filtered. The diethyl ether was distilled under reduced pressure, and then column separation was performed using ethyl acetate and n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain intermediate C (4.2 g). The peak was confirmed by M / Z = 485 by mass spectrum measurement of the obtained solid.
<화합물 A-5의 합성><Synthesis of Compound A-5>
[반응식 9] Scheme 9
Figure PCTKR2016010574-appb-I000057
Figure PCTKR2016010574-appb-I000057
500ml 2구 플라스크에 중간체 C (7.4g), 말라노니트릴(malononitrile)(6.1g)를 넣고 디클로로메탄 300ml로 녹인 후, 티타늄(Ⅳ)클로라이드(Titanium(Ⅳ)chloride) (13.5 ml)와 피리딘 (Pyridine)(20.0ml)를 0℃에서 차례대로 15분간 적가한다. 그 후, 질소조건에서 4시간 동안 실온 교반시켰다. 그 후, 디클로로메탄을 감압증류하여 제거하고, 1% 묽은 염산과클로로포름으로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 클로로포름를 감압증류한 후, 메틸렌 클로라이드, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 A-5 (4.0g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=533에서 피크가 확인되었다.Intermediate C (7.4 g), malononitrile (6.1 g) was added to a 500 ml two-necked flask, and dissolved in 300 ml of dichloromethane. Then, titanium (IV) chloride (13.5 ml) and pyridine ( Pyridine) (20.0 ml) was added dropwise at 0 ° C. over 15 minutes. Thereafter, the mixture was stirred at room temperature for 4 hours under nitrogen conditions. Thereafter, the dichloromethane was removed by distillation under reduced pressure, worked up with 1% dilute hydrochloric acid and chloroform, dried over anhydrous sodium sulfate and filtered. Chloroform was distilled under reduced pressure, and then separated by methylene chloride, n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain a compound A-5 (4.0 g). The peak was confirmed by M / Z = 533 by the mass spectrum measurement of the obtained solid.
<화합물 A-6의 합성><Synthesis of Compound A-6>
[반응식 10]Scheme 10
Figure PCTKR2016010574-appb-I000058
Figure PCTKR2016010574-appb-I000058
중간체 C 4.2g을 디클로로메탄 200ml에 교반, 용해시켰다. 플라스크 내를 질소 분위기로 하고, 용액 온도를 -10℃ 이하로 냉각했다. 그 용액에 사염화타이타늄 3.2mL을 가하고, 그 후, 비스트라이메틸실릴 카보다이이미드 16.4g과 디클로로메탄 80ml의 혼합액을 적하했다. 적하 종료 후, 1시간 냉각을 계속한 후, 4시간 실온에서 교반하고, 추가로 2시간 환류 교반했다. 석출된 고체를 여과하고, 메탄올로 세정하여 화합물 A-6 (2.2g)을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=509에서 피크가 확인되었다.4.2 g of intermediate C was stirred and dissolved in 200 ml of dichloromethane. The inside of the flask was made into nitrogen atmosphere, and the solution temperature was cooled to -10 degrees C or less. Titanium tetrachloride 3.2mL was added to this solution, and the liquid mixture of 16.4 g of bistrimethylsilyl carbodiimide and 80 ml of dichloromethanes was dripped thereafter. After completion of the dropwise addition, cooling was continued for 1 hour, followed by stirring at room temperature for 4 hours, and further refluxing stirring for 2 hours. The precipitated solid was filtered and washed with methanol to obtain compound A-6 (2.2 g). The peak was confirmed by M / Z = 509 by mass spectrum measurement of the obtained solid.
<중간체 D의 합성>Synthesis of Intermediate D
[반응식 11]Scheme 11
Figure PCTKR2016010574-appb-I000059
Figure PCTKR2016010574-appb-I000059
아세나프틸렌-1,2-다이온 7.4g과 1,3-비스(4-브로모페닐)프로판-2-온 15.1g을 메탄올 300 ml에 녹이고, 질소 조건에서 4시간 환류 교반을 행했다. 냉각 후, 반응액을 여과하고, 물, 메탄올로 세정하고, 추가로 아세토나이트릴로 슬러리 정제하여 검은색 고체를 7.4g 얻었다. 다음으로, 아르곤조건에서 상기에서 얻은 고체 7.4g에 시안화구리 (CuCN) 2.8g을 첨가하고 N-메틸-2-피롤리디논 (N-methyl-2-pyrrolidinone) (100mL) 을 투입하여 교반하였다. 그 후 180℃까지 가열하여 24시간 교반하였다. 실온으로 냉각한 후 디에틸에테르 (400mL)와 암모니아수로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 디에틸에테르를 감압증류한 후, 에틸아세테이트, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 중간체 D (6.2g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=406에서 피크가 확인되었다.7.4 g of acenaphthylene-1,2-dione and 15.1 g of 1,3-bis (4-bromophenyl) propan-2-one were dissolved in 300 ml of methanol and stirred under reflux for 4 hours under nitrogen conditions. After cooling, the reaction solution was filtered, washed with water and methanol, and further purified by slurry with acetonitrile to obtain 7.4 g of a black solid. Next, 2.8 g of copper cyanide (CuCN) was added to 7.4 g of the solid obtained above under argon, and N-methyl-2-pyrrolidinone (100 mL) was added and stirred. Then, it heated to 180 degreeC and stirred for 24 hours. After cooling to room temperature, the mixture was worked up with diethyl ether (400 mL) and ammonia water, dried over anhydrous sodium sulfate, and filtered. The diethyl ether was distilled under reduced pressure, and then column separation was performed using ethyl acetate and n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain compound intermediate D (6.2 g). The peak was confirmed by M / Z = 406 by the mass spectrum measurement of the obtained solid.
<화합물 A-7의 합성><Synthesis of Compound A-7>
[반응식 12]Scheme 12
Figure PCTKR2016010574-appb-I000060
Figure PCTKR2016010574-appb-I000060
500ml 2구 플라스크에 중간체 D (6.2g), 말라노니트릴(malononitrile)(6.1g)를 넣고 디클로로메탄 300ml로 녹인 후, 티타늄(Ⅳ)클로라이드(Titanium(Ⅳ)chloride)(13.5 ml)와 피리딘 (Pyridine)(20.0ml)를 0℃에서 차례대로 15분간 적가한다. 그 후, 질소조건에서 4시간 동안 실온 교반시켰다. 그 후, 디클로로메탄을 감압증류하여 제거하고, 1% 묽은 염산과 클로로포름으로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 클로로포름을 감압증류한 후, 메틸렌 클로라이드, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 A-7 (4.8g)을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=454에서 피크가 확인되었다.In a 500 ml two-necked flask, Intermediate D (6.2 g) and malononitrile (6.1 g) were added and dissolved in 300 ml of dichloromethane. Then, titanium (IV) chloride (13.5 ml) and pyridine ( Pyridine) (20.0 ml) was added dropwise at 0 ° C. over 15 minutes. Thereafter, the mixture was stirred at room temperature for 4 hours under nitrogen conditions. Thereafter, dichloromethane was removed by distillation under reduced pressure, and the mixture was worked up with 1% dilute hydrochloric acid and chloroform, dried over anhydrous sodium sulfate and filtered. Chloroform was distilled under reduced pressure, and then separated by methylene chloride, n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain a compound A-7 (4.8 g). The peak was confirmed by M / Z = 454 by the mass spectrum measurement of the obtained solid.
<화합물 A-8의 합성>Synthesis of Compound A-8
[반응식 13]Scheme 13
Figure PCTKR2016010574-appb-I000061
Figure PCTKR2016010574-appb-I000061
중간체 D (3.5g)를 디클로로메탄 200ml에 교반, 용해시켰다. 플라스크 내를 질소 분위기로 하고, 용액 온도를 -10℃ 이하로 냉각했다. 그 용액에 사염화타이타늄 3.2mL을 가하고, 그 후, 비스트라이메틸실릴 카보다이이미드 16.4g과 디클로로메탄 80ml의 혼합액을 적하했다. 적하 종료 후, 1시간 냉각을 계속한 후, 4시간 실온에서 교반하고, 추가로 2시간 환류 교반했다. 석출된 고체를 여과하고, 메탄올로 세정하여 화합물 A-8 (2.6g)을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=430에서 피크가 확인되었다.Intermediate D (3.5 g) was stirred and dissolved in 200 ml of dichloromethane. The inside of the flask was made into nitrogen atmosphere, and the solution temperature was cooled to -10 degrees C or less. Titanium tetrachloride 3.2mL was added to this solution, and the liquid mixture of 16.4 g of bistrimethylsilyl carbodiimide and 80 ml of dichloromethanes was dripped thereafter. After completion of the dropwise addition, cooling was continued for 1 hour, followed by stirring at room temperature for 4 hours, and further refluxing stirring for 2 hours. The precipitated solid was filtered and washed with methanol to obtain compound A-8 (2.6 g). The peak was confirmed by M / Z = 430 by the mass spectrum measurement of the obtained solid.
<중간체 E의 합성>Synthesis of Intermediate E
[반응식 14]Scheme 14
Figure PCTKR2016010574-appb-I000062
Figure PCTKR2016010574-appb-I000062
1,2-비스(4-브로모페닐)에탄-1,2-다이온 14.9g과 (4-사이아노페닐)보론산14.3g, 테트라키스트리페닐포스피노팔라듐 (2.3g), 탄산칼륨 10.60g (54mmol), 테트라하이드로퓨란 80 mL, 1,4-다이옥산 40 mL, 물 40 mL를 가한 후 환류조건에서 12시간 교반하였다. 상온으로 냉각한 후 증류수 40mL를 투입하고 에틸아세테이트 140mL로 2회 추출하였다. 얻어진 유기층을 황산나트륨 (MgSO4)으로 건조하였다. 그 후, 여과 분별한 후 용매를 감압증류 제거하고, 실리카겔 (silica gel) 컬럼크로마토그래피작업으로 화합물 15.6g을 얻었다. 다음으로, 얻은 고체 15.6g과 1,3-비스(페닐)프로판-2-온 16.0g을 메탄올 300 ml에 녹이고, 질소 조건에서 4시간 환류 교반을 행했다. 냉각 후, 반응액을 여과하고, 물, 메탄올로 세정하고, 추가로 아세토나이트릴로 슬러리 정제하여 검은색 고체인 중간체 E (10.4g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=587에서 피크가 확인되었다.14.9 g of 1,2-bis (4-bromophenyl) ethane-1,2-dione and 14.3 g of (4-cyanophenyl) boronic acid, tetrakistriphenylphosphinopalladium (2.3 g), potassium carbonate 10.60 g (54 mmol), 80 mL of tetrahydrofuran, 40 mL of 1,4-dioxane and 40 mL of water were added thereto, followed by stirring at reflux for 12 hours. After cooling to room temperature, 40 mL of distilled water was added and extracted twice with 140 mL of ethyl acetate. The obtained organic layer was dried over sodium sulfate (MgSO 4 ). After filtration and fractionation, the solvent was distilled off under reduced pressure and the compound 15.6 g was obtained by silica gel column chromatography. Next, 15.6 g of the obtained solid and 16.0 g of 1,3-bis (phenyl) propan-2-one were dissolved in 300 ml of methanol, and reflux stirring was performed for 4 hours under nitrogen conditions. After cooling, the reaction solution was filtered, washed with water and methanol, and further purified by slurry with acetonitrile to obtain an intermediate E (10.4 g) as a black solid. The peak was confirmed by M / Z = 587 by mass spectrum measurement of the obtained solid.
<화합물 A-9의 합성>Synthesis of Compound A-9
[반응식 15]Scheme 15
Figure PCTKR2016010574-appb-I000063
Figure PCTKR2016010574-appb-I000063
500ml 2구 플라스크에 중간체 A (9.0g), 말라노니트릴(malononitrile) (6.1g)를 넣고 디클로로메탄 300ml로 녹인 후, 티타늄(Ⅳ)클로라이드(Titanium(Ⅳ)chloride) (13.5 ml)와 피리딘 (Pyridine)(20.0ml)를 0℃에서 차례대로 15분간 적가한다. 그 후, 질소조건에서 4시간 동안 실온 교반시켰다. 그 후, 디클로로메탄을 감압증류하여 제거하고, 1% 묽은 염산과 클로로포름으로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 클로로포름을 감압증류한 후, 메틸렌 클로라이드, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 A-9 (4.0g)를 얻었다. 도 4를 참고하면, 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=635서 피크가 확인되는 것을 알 수 있다.Intermediate A (9.0 g), malononitrile (6.1 g) was added to a 500 ml two-necked flask, and dissolved in 300 ml of dichloromethane. Then, titanium (IV) chloride (13.5 ml) and pyridine ( Pyridine) (20.0 ml) was added dropwise at 0 ° C. over 15 minutes. Thereafter, the mixture was stirred at room temperature for 4 hours under nitrogen conditions. Thereafter, dichloromethane was removed by distillation under reduced pressure, and the mixture was worked up with 1% dilute hydrochloric acid and chloroform, dried over anhydrous sodium sulfate and filtered. Chloroform was distilled under reduced pressure, and then separated by methylene chloride, n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain a compound A-9 (4.0 g). Referring to FIG. 4, it can be seen that the peak at M / Z = 635 is confirmed by the mass spectrum measurement of the obtained solid.
<중간체 F의 합성>Synthesis of Intermediate F
[반응식 16]Scheme 16
Figure PCTKR2016010574-appb-I000064
Figure PCTKR2016010574-appb-I000064
5-브로모아세나프틸렌-1,2-다이온 10.6g과 1,3-비스(4-페닐)프로판-2-온 8.6g을 메탄올 300 ml에 녹이고, 질소조건에서 4시간 환류 교반을 행했다. 냉각 후, 반응액을 여과하고, 물, 메탄올로 세정하고, 추가로 아세토나이트릴로 슬러리 정제하여 검은색 고체를 6.4g 얻었다. 다음으로, 아르곤조건에서 상기에서 얻은 고체 6.4g에 시안화구리 (CuCN) 1.6g을 첨가하고 N-메틸-2-피롤리디논 (N-methyl-2-pyrrolidinone) (100mL) 을 투입하여 교반하였다. 그 후 180℃까지 가열하여 24시간 교반하였다. 실온으로 냉각한 후 디에틸에테르 (400mL)와 암모니아수로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 디에틸에테르를 감압증류한 후, 에틸아세테이트, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 중간체 F (4.2g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=381에서 피크가 확인되었다.10.6 g of 5-bromoacenaphthylene-1,2-dione and 8.6 g of 1,3-bis (4-phenyl) propan-2-one were dissolved in 300 ml of methanol, and the mixture was stirred under reflux for 4 hours under nitrogen conditions. . After cooling, the reaction solution was filtered, washed with water and methanol, and further purified by slurry with acetonitrile to obtain 6.4 g of a black solid. Next, 1.6 g of copper cyanide (CuCN) was added to 6.4 g of the solid obtained above under argon, and N-methyl-2-pyrrolidinone (100 mL) was added and stirred. Then, it heated to 180 degreeC and stirred for 24 hours. After cooling to room temperature, the mixture was worked up with diethyl ether (400 mL) and ammonia water, dried over anhydrous sodium sulfate, and filtered. The diethyl ether was distilled under reduced pressure, and then column separation was performed using ethyl acetate and n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain compound intermediate F (4.2 g). The peak was confirmed by M / Z = 381 by the mass spectrum measurement of the obtained solid.
<화합물 A-10의 합성><Synthesis of Compound A-10>
[반응식 17] Scheme 17
Figure PCTKR2016010574-appb-I000065
Figure PCTKR2016010574-appb-I000065
500ml 2구 플라스크에 중간체 F (5.8g), 말라노니트릴(malononitrile) (6.1g)를 넣고 디클로로메탄 300ml로 녹인 후, 티타늄(Ⅳ)클로라이드(Titanium(Ⅳ)chloride) (13.5 ml)와 피리딘 (Pyridine)(20.0ml)를 0℃에서 차례대로 15분간 적가한다. 그 후, 질소조건에서 4시간 동안 실온 교반시켰다. 그 후, 디클로로메탄을 감압증류하여 제거하고, 1% 묽은 염산과 클로로포름으로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 클로로포름을 감압증류한 후, 메틸렌 클로라이드, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 A-10 (3.2g)을 얻었다. 도 5를 참고하면, 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=429에서 피크가 확인되는 것을 알 수 있다.In a 500 ml two-necked flask, intermediate F (5.8 g) and malononitrile (6.1 g) were added and dissolved in 300 ml of dichloromethane. Then, titanium (IV) chloride (13.5 ml) and pyridine ( Pyridine) (20.0 ml) was added dropwise at 0 ° C. over 15 minutes. Thereafter, the mixture was stirred at room temperature for 4 hours under nitrogen conditions. Thereafter, dichloromethane was removed by distillation under reduced pressure, and the mixture was worked up with 1% dilute hydrochloric acid and chloroform, dried over anhydrous sodium sulfate and filtered. Chloroform was distilled under reduced pressure, and then separated by methylene chloride, n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain compound A-10 (3.2 g). Referring to FIG. 5, it can be seen that the peak is confirmed at M / Z = 429 by mass spectrum measurement of the obtained solid.
<중간체 G의 합성>Synthesis of Intermediate G
[반응식 18]Scheme 18
Figure PCTKR2016010574-appb-I000066
Figure PCTKR2016010574-appb-I000066
아세나프틸렌-1,2-다이온 7.4g과 1,3-비스(4-브로모페닐)프로판-2-온 15.7g을 메탄올 300 ml에 녹이고, 질소 조건에서 4시간 환류 교반을 행했다. 냉각 후, 반응액을 여과하고, 물, 메탄올로 세정하고, 추가로 아세토나이트릴로 슬러리 정제하여 검은색 고체를 9.8g 얻었다. 다음으로, 아르곤조건에서 상기에서 얻은 고체 9.8g에 시안화구리 (CuCN) 3.8g을 첨가하고 N-메틸-2-피롤리디논 (N-methyl-2-pyrrolidinone) (100mL) 을 투입하여 교반하였다. 그 후 180℃까지 가열하여 24시간 교반하였다. 실온으로 냉각한 후 디에틸에테르 (400mL)와 암모니아수로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 디에틸에테르를 감압증류한 후, 에틸아세테이트, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 중간체 G (4.8g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=406에서 피크가 확인되었다7.4 g of acenaphthylene-1,2-dione and 15.7 g of 1,3-bis (4-bromophenyl) propan-2-one were dissolved in 300 ml of methanol, and the mixture was stirred under reflux for 4 hours under nitrogen conditions. After cooling, the reaction solution was filtered, washed with water and methanol, and further purified with slurry by acetonitrile to obtain 9.8 g of a black solid. Next, 3.8 g of copper cyanide (CuCN) was added to 9.8 g of the solid obtained above under argon conditions, and N-methyl-2-pyrrolidinone (100 mL) was added and stirred. Then, it heated to 180 degreeC and stirred for 24 hours. After cooling to room temperature, the mixture was worked up with diethyl ether (400 mL) and ammonia water, dried over anhydrous sodium sulfate, and filtered. The diethyl ether was distilled under reduced pressure, and then column separation was performed using ethyl acetate and n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain intermediate G (4.8 g). The peak was confirmed at M / Z = 406 by mass spectrum measurement of the obtained solid.
<화합물 A-11의 합성>Synthesis of Compound A-11
[반응식 19]Scheme 19
Figure PCTKR2016010574-appb-I000067
Figure PCTKR2016010574-appb-I000067
500ml 2구 플라스크에 중간체 G (6.2g), 말라노니트릴(malononitrile) (6.1g)를 넣고 디클로로메탄 300ml로 녹인 후, 티타늄(Ⅳ)클로라이드(Titanium(Ⅳ)chloride) (13.5 ml)와 피리딘 (Pyridine)(20.0ml)를 0℃에서 차례대로 15분간 적가한다. 그 후, 질소조건에서 4시간 동안 실온 교반시켰다. 그 후, 디클로로메탄을 감압증류하여 제거하고, 1% 묽은 염산과 클로로포름으로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 클로로포름을 감압증류한 후, 메틸렌 클로라이드, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 A-11 (5.2g)을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=454에서 피크가 확인되었다.Intermediate G (6.2 g), malononitrile (6.1 g) was added to a 500 ml two-necked flask, and dissolved in 300 ml of dichloromethane. Then, titanium (IV) chloride (13.5 ml) and pyridine ( Pyridine) (20.0 ml) was added dropwise at 0 ° C. over 15 minutes. Thereafter, the mixture was stirred at room temperature for 4 hours under nitrogen conditions. Thereafter, dichloromethane was removed by distillation under reduced pressure, and the mixture was worked up with 1% dilute hydrochloric acid and chloroform, dried over anhydrous sodium sulfate and filtered. Chloroform was distilled under reduced pressure, and then separated by methylene chloride, n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain a compound A-11 (5.2 g). The peak was confirmed by M / Z = 454 by the mass spectrum measurement of the obtained solid.
<중간체 H의 합성>Synthesis of Intermediate H
[반응식 20] Scheme 20
Figure PCTKR2016010574-appb-I000068
Figure PCTKR2016010574-appb-I000068
5,6-디플루오르아세나프틸렌-1,2-다이온 8.9g과 1,3-비스(4-브로모페닐)프로판-2-온 10.5g을 메탄올 300 ml에 녹이고, 질소 조건에서 4시간 환류 교반을 행했다. 냉각 후, 반응액을 여과하고, 물, 메탄올로 세정하고, 추가로 아세토나이트릴로 슬러리 정제하여 검은색 고체인 중간체 H (6.8g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=428에서 피크가 확인되었다8.9 g of 5,6-difluoroacenaphthylene-1,2-dione and 10.5 g of 1,3-bis (4-bromophenyl) propan-2-one are dissolved in 300 ml of methanol, followed by 4 hours under nitrogen conditions. Reflux stirring was performed. After cooling, the reaction solution was filtered, washed with water and methanol, and further purified by slurry with acetonitrile to obtain an intermediate H (6.8 g) as a black solid. The peak was confirmed at M / Z = 428 by mass spectrum measurement of the obtained solid.
<화합물 A-12의 합성>Synthesis of Compound A-12
[반응식 21]Scheme 21
Figure PCTKR2016010574-appb-I000069
Figure PCTKR2016010574-appb-I000069
500ml 2구 플라스크에 중간체 H (6.5g), 말라노니트릴(malononitrile) (6.1g)를 넣고 디클로로메탄 300ml로 녹인 후, 티타늄(Ⅳ)클로라이드(Titanium(Ⅳ)chloride) (13.5 ml)와 피리딘 (Pyridine)(20.0ml)를 0℃에서 차례대로 15분간 적가한다. 그 후, 질소조건에서 4시간 동안 실온 교반시켰다. 그 후, 디클로로메탄을 감압증류하여 제거하고, 1% 묽은 염산과 클로로포름으로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 클로로포름을 감압증류한 후, 메틸렌 클로라이드, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 A-12 (5.6g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=454에서 피크가 확인되었다.Intermediate H (6.5 g), malononitrile (6.1 g) was added to a 500 ml two-necked flask, and dissolved in 300 ml of dichloromethane. Then, titanium (IV) chloride (13.5 ml) and pyridine ( Pyridine) (20.0 ml) was added dropwise at 0 ° C. over 15 minutes. Thereafter, the mixture was stirred at room temperature for 4 hours under nitrogen conditions. Thereafter, dichloromethane was removed by distillation under reduced pressure, and the mixture was worked up with 1% dilute hydrochloric acid and chloroform, dried over anhydrous sodium sulfate and filtered. Chloroform was distilled under reduced pressure, and then separated by methylene chloride, n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain a compound A-12 (5.6 g). The peak was confirmed by M / Z = 454 by the mass spectrum measurement of the obtained solid.
<중간체 I의 합성>Synthesis of Intermediate I
[반응식 22]Scheme 22
Figure PCTKR2016010574-appb-I000070
Figure PCTKR2016010574-appb-I000070
1,2-비스(4-트리플루오르메틸페닐)에탄-1,2-다이온 14.1g과 1,3-비스(4-플루오르페닐)프로판-2-온 10.1g을 메탄올 300 ml에 녹이고, 질소 조건에서 4시간 환류 교반을 행했다. 냉각 후, 반응액을 여과하고, 물, 메탄올로 세정하고, 추가로 아세토나이트릴로 슬러리 정제하여 검은색 고체인 중간체 I (8.8g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=556에서 피크가 확인되었다.14.1 g of 1,2-bis (4-trifluoromethylphenyl) ethane-1,2-dione and 10.1 g of 1,3-bis (4-fluorophenyl) propan-2-one are dissolved in 300 ml of methanol and subjected to nitrogen conditions. Reflux stirring was performed for 4 hours. After cooling, the reaction solution was filtered, washed with water and methanol, and further purified by slurry with acetonitrile to give an intermediate I (8.8 g) as a black solid. The peak was confirmed by M / Z = 556 by the mass spectrum measurement of the obtained solid.
<화합물 A-13의 합성><Synthesis of Compound A-13>
[반응식 23]Scheme 23
Figure PCTKR2016010574-appb-I000071
Figure PCTKR2016010574-appb-I000071
500ml 2구 플라스크에 중간체 I (8.5g), 말라노니트릴(malononitrile) (6.1g)를 넣고 디클로로메탄 300ml로 녹인 후, 티타늄(Ⅳ)클로라이드(Titanium(Ⅳ)chloride) (13.5 ml)와 피리딘 (Pyridine)(20.0ml)를 0℃에서 차례대로 15분간 적가한다. 그 후, 질소조건에서 4시간 동안 실온 교반시켰다. 그 후, 디클로로메탄을 감압증류하여 제거하고, 1% 묽은 염산과 클로로포름으로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 클로로포름을 감압증류한 후, 메틸렌 클로라이드, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 A-13 (5.6g)을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=605에서 피크가 확인되었다.In a 500 ml two-necked flask, Intermediate I (8.5 g), malononitrile (6.1 g) was added, dissolved in 300 ml of dichloromethane, and titanium (IV) chloride (13.5 ml) and pyridine ( Pyridine) (20.0 ml) was added dropwise at 0 ° C. over 15 minutes. Thereafter, the mixture was stirred at room temperature for 4 hours under nitrogen conditions. Thereafter, dichloromethane was removed by distillation under reduced pressure, and the mixture was worked up with 1% dilute hydrochloric acid and chloroform, dried over anhydrous sodium sulfate and filtered. Chloroform was distilled under reduced pressure, and then separated by methylene chloride, n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain compound A-13 (5.6 g). The peak was confirmed by M / Z = 605 by mass spectrum measurement of the obtained solid.
<화합물 A-14의 합성>Synthesis of Compound A-14
[반응식 24]Scheme 24
Figure PCTKR2016010574-appb-I000072
Figure PCTKR2016010574-appb-I000072
중간체 A 1.8g과 1,3-디메틸바비튜릭산 1.9g을 빙초산 80mL, 아세틱안하이드라이드 80mL에 녹이고, 질소조건에서 12시간 환류 교반하였다. 그 후, 진공 조건에서 빙초산과, 아세틱안하이드라이드를 제거하였다. 그 후, 디클로로메탄과 물로 워크업(work up)한 후, 무수황산나트륨으로 건조 및 여과하였다. 디클로로메탄을 감압증류한 후, 메틸렌 클로라이드, n-헥산 1:1 용액을 이용하여 컬럼분리하였다. 이후, 에틸아세테이트를 이용하여 침전액을 만든 후, 여과하여 화합물 A-14 (0.6g)를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=595에서 피크가 확인되었다.1.8 g of intermediate A and 1.9 g of 1,3-dimethylbarbituric acid were dissolved in 80 mL of glacial acetic acid and 80 mL of acetic anhydride, followed by stirring under reflux for 12 hours under nitrogen. Thereafter, glacial acetic acid and acetic anhydride were removed under vacuum conditions. Thereafter, the mixture was worked up with dichloromethane and water, dried over anhydrous sodium sulfate and filtered. Dichloromethane was distilled under reduced pressure, followed by column separation using methylene chloride, n-hexane 1: 1 solution. Thereafter, a precipitate was prepared using ethyl acetate, and then filtered to obtain a compound A-14 (0.6 g). The peak was confirmed at M / Z = 595 by mass spectrum measurement of the obtained solid.
<소자 <Element 적용예Application example >>
이하, 전술한 합성예에서 제조된 본 발명의 일 실시예인 상기 화합물 A-1, A-3, A-5, A-7, A-9, A-10 및 A-11을 각각 정공 주입층에 도핑하여 유기 발광 소자를 제작한 실시예를 개시한다. 하기 실시예 1 내지 실시예 7 및 비교예 1 내지 비교예 3에서 MADN, BD-A, Alq3 및 α-NPB는 각각 하기의 화학식으로 표시되는 화합물이다. Hereinafter, 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. In Examples 1 to 7 and Comparative Examples 1 to 3, MADN, BD-A, Alq 3 and α-NPB are compounds represented by the following formulas, respectively.
Figure PCTKR2016010574-appb-I000073
Figure PCTKR2016010574-appb-I000073
<< 실시예Example 1> 1>
ITO glass의 발광 면적이 3mm × 3mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1×10-6 torr가 되도록 한 후 양극인 ITO 글라스 위에 전술한 화합물 A-1 (20중량%)이 도핑된 α-NPB(100Å)를 형성한다. 이어서, 정공수송층으로 α-NPD를 600Å의 두께로 형성하고, 발광층으로 호스트인 MADN에 도펀트인 BD-A을 중량비가 40:2가 되도록 증착하고, 전자 수송층으로 Alq3를 300Å의 두께로 형성하고 전자 주입층으로 LiF를 10Å의 두께로 형성하고, 음극으로 Al을 800Å의 두께로 순차적으로 형성하여 유기 발광 소자를 제작하였다.The light emitting area of the ITO glass was patterned to have a size of 3 mm × 3 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 −6 torr, and then α-NPB (100 kPa) doped with the aforementioned compound A-1 (20 wt%) was formed on the anode ITO glass. Subsequently, α-NPD was formed to a thickness of 600 kV with the hole transport layer, and BD-A, a dopant, was deposited on the host MADN with a weight ratio of 40: 2, and 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, and Al was sequentially formed to a thickness of 800 kPa as a cathode to fabricate an organic light emitting device.
<< 실시예Example 2> 2>
전술한 실시예 1과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-3을 정공 주입층에 도핑한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 1, 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.
<< 실시예Example 3> 3>
전술한 실시예 1과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-5를 정공 주입층에 도핑한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 1, 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.
<< 실시예Example 4> 4>
전술한 실시예 1과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-7을 정공 주입층에 도핑한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 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.
<< 실시예Example 5> 5>
전술한 실시예 1과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-9를 정공 주입층에 도핑한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 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.
<< 실시예Example 6> 6>
전술한 실시예 1과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-10을 정공 주입층에 도핑한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 1, 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.
<< 실시예Example 7> 7>
전술한 실시예 1과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-11을 정공 주입층에 도핑한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 1, 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.
<< 비교예Comparative example 1> 1>
전술한 실시예 1과 동일한 공정 조건하에, 정공 주입층에 화합물 A-1 대신 HAT-CN을 도핑한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 1, 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.
<< 비교예Comparative example 2> 2>
전술한 실시예 1과 동일한 공정 조건하에, 어떠한 도핑없이 정공 주입층을 700Å 형성한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 1, the organic light emitting device was manufactured by using only 700 Å of the hole injection layer without any doping.
<< 비교예Comparative example 3> 3>
전술한 실시예 1과 동일한 공정 조건하에, 정공 주입층에 화합물 A-1 대신 하기 화합물 B-1의 화합물을 도핑한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 1, 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.
[화합물 B-1][Compound B-1]
Figure PCTKR2016010574-appb-I000074
Figure PCTKR2016010574-appb-I000074
실시예 1 내지 실시예 7 및 비교예 1 내지 비교예 3에서 제조된 유기 발광 소자의 구동전압, 전류효율, 전력효율 및 휘도를 하기 표 1에 나타내었다. 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.
Condition IDCondition ID 구동 전압(V)Drive voltage (V) 전류밀도(mA/cm2)Current density (mA / cm 2 ) 전류효율(cd/A)Current efficiency (cd / A) 전력효율(lm/W)Power efficiency (lm / W) 휘도(cd/m2)Luminance (cd / m 2 )
실시예1Example 1 4.64.6 1010 5.365.36 3.6613.661 536536
실시예2Example 2 4.54.5 1010 5.65.6 3.9103.910 560560
실시예3Example 3 4.74.7 1010 5.25.2 3.4763.476 520520
실시예4Example 4 4.14.1 1010 5.815.81 4.4524.452 581581
실시예5Example 5 4.24.2 1010 5.695.69 4.2564.256 569569
실시예6Example 6 4.34.3 1010 5.625.62 4.1064.106 562562
실시예7Example 7 4.34.3 1010 5.625.62 4.1064.106 562562
비교예1Comparative Example 1 5.85.8 1010 4.624.62 2.5022.502 462462
비교예2Comparative Example 2 8.28.2 1010 4.24.2 1.6091.609 420420
비교예3Comparative Example 3 6.96.9 1010 4.484.48 2.0402.040 448448
이하, 전술한 합성예에서 제조된 본 발명의 일 실시예인 상기 화합물 A-1, A-3, A-5, A-10, A-11 및 A-12를 각각 정공 주입층에 단독으로 사용하여 유기 발광 소자를 제작한 실시예를 개시한다. 하기 실시예 8 내지 실시예 13 및 비교예 4 내지 비교예 6에서 Ir(ppy)3, CBP 및 BCP는 각각 하기의 화학식으로 표시되는 화합물이다.Hereinafter, 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. In Examples 8 to 13 and Comparative Examples 4 to 6, Ir (ppy) 3 , CBP, and BCP are compounds represented by the following formulas, respectively.
Figure PCTKR2016010574-appb-I000075
Figure PCTKR2016010574-appb-I000075
<< 실시예Example 8> 8>
ITO glass의 발광 면적이 3mm × 3mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1×10-6 torr가 되도록 한 후, 유기물을 양극인 ITO 상에 정공 주입층으로 화합물 A-1을 40Å의 두께로 형성하고, 정공 수송층으로 α-NPD를 800Å의 두께로 형성하고, 노란색 발광층으로 호스트인 CBP에 도펀트인 Ir(ppy)3를 10중량%의 도핑농도로 도핑하여 300Å의 두께로 형성하고, 정공 저지층으로 BCP를 50Å의 두께로 형성하고, 전자 수송층으로 Alq3를 150Å의 두께로 형성하고 전자 주입층으로 LiF를 5Å의 두께로 형성하고, 음극으로 Al을 1000Å의 두께로 순차적으로 형성하여 유기 발광 소자를 제작하였다.The light emitting area of the ITO glass was patterned to have a size of 3 mm × 3 mm and then washed. After mounting the substrate in the vacuum chamber, 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 α- NPD is formed to a thickness of 800Å, 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 300Å. 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.
<< 실시예Example 9> 9>
전술한 실시예 8과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-3을 정공 주입층에 사용한 것만을 달리하여 유기 발광 소자를 제작하였다. Under the same process conditions as in Example 8, 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.
<< 실시예Example 10> 10>
전술한 실시예 8과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-5를 정공 주입층에 사용한 것만을 달리하여 유기 발광 소자를 제작하였다. Under the same process conditions as in Example 8, 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.
<< 실시예Example 11> 11>
전술한 실시예 8과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-10을 정공 주입층에 사용한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 8, 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.
<< 실시예Example 12> 12>
전술한 실시예 8과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-11을 정공 주입층에 사용한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 8, 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.
<< 실시예Example 13> 13>
전술한 실시예 8과 동일한 공정 조건하에, 화합물 A-1 대신 화합물 A-12을 정공 주입층에 사용한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 8, 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.
<< 비교예Comparative example 4> 4>
전술한 실시예 8과 동일한 공정 조건하에, 정공 주입층에 화합물 A-1 대신 HAT-CN을 사용한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 8, the organic light emitting device was manufactured by using only the HAT-CN instead of the compound A-1 in the hole injection layer.
<< 비교예Comparative example 5> 5>
전술한 실시예 8과 동일한 공정 조건하에, 정공 주입층을 형성하지 않은 것만을 달리하여 유기 발광 소자를 제작하였다. Under the same process conditions as in Example 8 described above, the organic light emitting device was manufactured by changing only that the hole injection layer was not formed.
<< 비교예Comparative example 6> 6>
전술한 실시예 8과 동일한 공정 조건하에, 정공 주입층에 화합물 A-1 대신 화합물 B-1의 화합물을 사용한 것만을 달리하여 유기 발광 소자를 제작하였다.Under the same process conditions as in Example 8, 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.
[화합물 B-1][Compound B-1]
Figure PCTKR2016010574-appb-I000076
Figure PCTKR2016010574-appb-I000076
실시예 8 내지 실시예 13 및 비교예 4 내지 비교예 6에서 제조된 유기 발광 소자의 구동전압, 전류효율, 전력효율 및 휘도를 하기 표 2에 나타내었다.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.
Condition IDCondition ID 정공주입층재료Hole injection layer material 구동 전압(V)Drive voltage (V) 전류밀도(mA/cm2)Current density (mA / cm 2 ) 전류효율(cd/A)Current efficiency (cd / A) 전력효율(lm/W)Power efficiency (lm / W) 휘도(cd/m2)Luminance (cd / m 2 )
실시예 8Example 8 화합물A-1Compound A-1 4.74.7 1010 54.854.8 36.630 36.630 54805480
실시예 9Example 9 화합물A-3Compound A-3 4.44.4 1010 58.3458.34 41.655 41.655 58345834
실시예 10Example 10 화합물A-5 Compound A-5 44 1010 62.962.9 49.402 49.402 62906290
실시예 11Example 11 화합물A-10Compound A-10 4.24.2 1010 62.1862.18 46.511 46.511 62186218
실시예 12Example 12 화합물A-11Compound A-11 4.54.5 1010 57.8857.88 40.408 40.408 57885788
실시예 13Example 13 화합물A-12Compound A-12 4.34.3 1010 6262 45.297 45.297 62006200
비교예 4Comparative Example 4 HAT-CNHAT-CN 6.96.9 1010 45.2945.29 20.621 20.621 45294529
비교예 5Comparative Example 5 -- 8.28.2 1010 42.8842.88 16.428 16.428 42884288
비교예 6Comparative Example 6 화합물 B-1Compound B-1 88 1010 43.4643.46 17.067 17.067 43464346
이상을 통해 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속한다.Although the preferred embodiment of the present invention has been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also belong to the scope of the invention. .

Claims (20)

  1. 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2016010574-appb-I000077
    Figure PCTKR2016010574-appb-I000077
    상기 화학식 1에 있어서,In Chemical Formula 1,
    R1 내지 R4는 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,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 substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may combine with an adjacent group to form a substituted or unsubstituted ring,
    L은 C(n=2인 경우); CR5(n=1인 경우); N; 치환 또는 비치환된 (n+2)가 지방족 탄화수소기; 치환 또는 비치환된 (n+2)가 방향족 탄화수소기; 및 치환 또는 비치환된 (n+2)가 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이고,L is C (if n = 2); CR 5 (if n = 1); N; A substituted or unsubstituted (n + 2) is an aliphatic hydrocarbon group; A substituted or unsubstituted (n + 2) is an aromatic hydrocarbon group; And substituted or unsubstituted (n + 2) is any one selected from the group consisting of heterocyclic groups,
    상기 R5는 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이고,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,
    Y는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어지는 군에서 선택되고,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,
    n은 1 내지 4의 정수이며,n is an integer from 1 to 4,
    n이 2 이상인 경우, 괄호안의 구조는 서로 같거나 상이하다.When n is 2 or more, the structures in parentheses are the same or different from each other.
  2. 제1항에 있어서, 상기 화학식 1은 하기 화학식 2 또는 하기 화학식 3으로 표시되는 화합물:The compound of claim 1, wherein Formula 1 is represented by Formula 2 or below:
    [화학식 2][Formula 2]
    Figure PCTKR2016010574-appb-I000078
    Figure PCTKR2016010574-appb-I000078
    [화학식 3][Formula 3]
    Figure PCTKR2016010574-appb-I000079
    Figure PCTKR2016010574-appb-I000079
    상기 화학식 2 및 3에 있어서,In Chemical Formulas 2 and 3,
    R1, R4, L, Y 및 n은 상기 화학식 1에서 정의한 바와 같고,R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
    R6 내지 R8은 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,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 unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may combine with an adjacent group to form a substituted or unsubstituted ring,
    a 및 b는 각각 1 내지 5의 정수이고,a and b are each an integer of 1 to 5,
    c는 1 내지 4의 정수이며,c is an integer from 1 to 4,
    a, b 및 c가 각각 2 이상인 경우, 괄호안의 구조는 서로 같거나 상이하다.When a, b and c are each 2 or more, the structures in parentheses are the same or different from each other.
  3. 제1항에 있어서, 상기 화학식 1은 하기 화학식 4 또는 하기 화학식 5로 표시되는 화합물:The compound of claim 1, wherein Formula 1 is represented by Formula 4 or below:
    [화학식 4][Formula 4]
    Figure PCTKR2016010574-appb-I000080
    Figure PCTKR2016010574-appb-I000080
    [화학식 5][Formula 5]
    Figure PCTKR2016010574-appb-I000081
    Figure PCTKR2016010574-appb-I000081
    상기 화학식 4 및 5에 있어서,In Chemical Formulas 4 and 5,
    R1, R4, L, Y 및 n은 상기 화학식 1에서 정의한 바와 같고,R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
    R9 내지 R12는 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,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 unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may combine with an adjacent group to form a substituted or unsubstituted ring,
    d 및 e는 각각 1 내지 3의 정수이며,d and e are each an integer of 1 to 3,
    f 및 g는 각각 1 내지 4의 정수이며,f and g are each an integer of 1 to 4,
    d, e, f 및 g가 각각 2 이상인 경우, 괄호안의 구조는 서로 같거나 상이하다.When d, e, f, and g are each 2 or more, the structures in parentheses are the same or different from each other.
  4. 제1항에 있어서, 상기 화학식 1은 하기 화학식 6, 하기 화학식 7 또는 하기 화학식 8로 표시되는 화합물:The compound of claim 1, wherein Formula 1 is represented by Formula 6, Formula 7, or Formula 8 below:
    [화학식 6][Formula 6]
    Figure PCTKR2016010574-appb-I000082
    Figure PCTKR2016010574-appb-I000082
    [화학식 7][Formula 7]
    Figure PCTKR2016010574-appb-I000083
    Figure PCTKR2016010574-appb-I000083
    [화학식 8][Formula 8]
    Figure PCTKR2016010574-appb-I000084
    Figure PCTKR2016010574-appb-I000084
    상기 화학식 6 내지 8에 있어서,In Chemical Formulas 6 to 8,
    R1, R4, L, Y 및 n은 상기 화학식 1에서 정의한 바와 같고,R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
    R13 내지 R21은 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,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 unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may combine with an adjacent group to form a substituted or unsubstituted ring,
    h 내지 j는 각각 1 또는 2이며,h to j are each 1 or 2,
    k 및 o는 각각 1 내지 3의 정수이며,k and o are each an integer of 1 to 3,
    l 및 p는 각각 1 내지 3의 정수이며,l and p are each an integer of 1 to 3,
    h, i, j, k, o, l 및 p가 각각 2 이상인 경우, 괄호안의 구조는 서로 같거나 상이하다.When h, i, j, k, o, l and p are each 2 or more, the structures in parentheses are the same or different from each other.
  5. 제1항에 있어서, 상기 화학식 1은 하기 화학식 9 또는 하기 화학식 10으로 표시되는 화합물:The compound of claim 1, wherein Formula 1 is represented by Formula 9 or Formula 10:
    [화학식 9][Formula 9]
    Figure PCTKR2016010574-appb-I000085
    Figure PCTKR2016010574-appb-I000085
    [화학식 10][Formula 10]
    Figure PCTKR2016010574-appb-I000086
    Figure PCTKR2016010574-appb-I000086
    상기 화학식 9 및 10에 있어서,In Chemical Formulas 9 and 10,
    R1, R4, L, Y 및 n은 상기 화학식 1에서 정의한 바와 같고,R 1 , R 4 , L, Y and n are the same as defined in Formula 1,
    R22 내지 R27은 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,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 unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it may be any one selected from the group consisting of a substituted or unsubstituted heterocyclic group, or may combine with an adjacent group to form a substituted or unsubstituted ring,
    r 내지 u는 각각 1 내지 3의 정수이며,r to u are each an integer of 1 to 3,
    v는 1 또는 2이며,v is 1 or 2,
    r 내지 u 및 v가 각각 2 이상인 경우, 괄호안의 구조는 서로 같거나 상이하다.When r to u and v are each 2 or more, the structures in parentheses are the same or different from each other.
  6. 제1항에 있어서, 상기 =L-(Y)n은 하기 화학식 11로 표시되는 화합물:The compound of claim 1, wherein = L- (Y) n is represented by Formula 11 below:
    [화학식 11][Formula 11]
    Figure PCTKR2016010574-appb-I000087
    Figure PCTKR2016010574-appb-I000087
    상기 화학식 11에 있어서,In Chemical Formula 11,
    R28 내지 R31은 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 알킬아릴기; 및 치환 또는 비치환된 아릴기로 이루어진 군에서 선택되는 어느 하나이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.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.
  7. 제1항에 있어서, 상기 =L-(Y)n은 하기 화학식 12 또는 하기 화학식 13으로 표시되는 화합물:The compound of claim 1, wherein = L- (Y) n is represented by Formula 12 or Formula 13 below:
    [화학식 12][Formula 12]
    Figure PCTKR2016010574-appb-I000088
    Figure PCTKR2016010574-appb-I000088
    [화학식 13][Formula 13]
    Figure PCTKR2016010574-appb-I000089
    Figure PCTKR2016010574-appb-I000089
    상기 화학식 12 및 13에 있어서,In Chemical Formulas 12 and 13,
    X1 내지 X4는 각각 독립적으로 NR32; S; O; 또는 PR32이며,X 1 to X 4 are each independently NR 32 ; S; O; Or PR 32 ,
    Y1 내지 Y5는 각각 독립적으로 S; 또는 O이고,Y 1 to Y 5 are each independently S; Or O,
    상기 R32는 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 어느 하나이다.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.
  8. 제1항에 있어서, 상기 Y는 니트릴기; 바르비투레이트기; 또는 로다닌기인 화합물.According to claim 1, wherein Y is a nitrile group; Barbiturate groups; Or a rhodanine group.
  9. 제1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 중 어느 하나로 표시되는 화합물:The compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas:
    Figure PCTKR2016010574-appb-I000090
    Figure PCTKR2016010574-appb-I000090
    Figure PCTKR2016010574-appb-I000091
    Figure PCTKR2016010574-appb-I000091
    Figure PCTKR2016010574-appb-I000092
    Figure PCTKR2016010574-appb-I000092
    Figure PCTKR2016010574-appb-I000093
    Figure PCTKR2016010574-appb-I000093
    Figure PCTKR2016010574-appb-I000094
    Figure PCTKR2016010574-appb-I000094
    Figure PCTKR2016010574-appb-I000095
    Figure PCTKR2016010574-appb-I000095
    Figure PCTKR2016010574-appb-I000096
    Figure PCTKR2016010574-appb-I000096
    Figure PCTKR2016010574-appb-I000097
    Figure PCTKR2016010574-appb-I000097
    Figure PCTKR2016010574-appb-I000098
    Figure PCTKR2016010574-appb-I000098
    Figure PCTKR2016010574-appb-I000099
    Figure PCTKR2016010574-appb-I000099
    Figure PCTKR2016010574-appb-I000100
    Figure PCTKR2016010574-appb-I000100
    Figure PCTKR2016010574-appb-I000101
    Figure PCTKR2016010574-appb-I000101
    Figure PCTKR2016010574-appb-I000102
    Figure PCTKR2016010574-appb-I000102
    Figure PCTKR2016010574-appb-I000103
    Figure PCTKR2016010574-appb-I000103
    Figure PCTKR2016010574-appb-I000104
    Figure PCTKR2016010574-appb-I000104
    Figure PCTKR2016010574-appb-I000105
    Figure PCTKR2016010574-appb-I000105
    Figure PCTKR2016010574-appb-I000106
    Figure PCTKR2016010574-appb-I000106
    Figure PCTKR2016010574-appb-I000107
    Figure PCTKR2016010574-appb-I000107
    Figure PCTKR2016010574-appb-I000108
    Figure PCTKR2016010574-appb-I000108
    Figure PCTKR2016010574-appb-I000109
    Figure PCTKR2016010574-appb-I000109
    Figure PCTKR2016010574-appb-I000110
    Figure PCTKR2016010574-appb-I000110
  10. 제1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 중 어느 하나로 표시되는 화합물:The compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas:
    Figure PCTKR2016010574-appb-I000111
    Figure PCTKR2016010574-appb-I000111
  11. 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서,A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode.
    상기 유기물층 중 1층 이상은 제1항 내지 제10항 중 어느 하나의 항에 따른 화합물을 포함하는 것인 유기 발광 소자.At least one of the organic material layer is an organic light-emitting device comprising a compound according to any one of claims 1 to 10.
  12. 제11항에 있어서, 상기 유기물층은 상기 화합물 단독으로 이루어지거나, 또는 상기 화합물이 도핑되어 이루어진 것인 유기 발광 소자.The organic light emitting device of claim 11, wherein the organic material layer is formed of the compound alone, or is doped with the compound.
  13. 제11항에 있어서, 상기 유기물층은 정공 주입층, 정공 생성층, 정공 버퍼층 또는 정공 수송층인 것인 유기 발광 소자.The organic light emitting diode of claim 11, wherein the organic material layer is a hole injection layer, a hole generating layer, a hole buffer layer, or a hole transport layer.
  14. 제11항에 있어서, 상기 유기물층은 정공 생성과 정공 수송을 동시에 하는 층인 것인 유기 발광 소자.The organic light emitting device of claim 11, wherein the organic material layer is a layer for simultaneously generating holes and transporting holes.
  15. 제11항에 있어서, 상기 유기물층은 발광층인 것인 유기 발광 소자.The organic light emitting device of claim 11, wherein the organic material layer is a light emitting layer.
  16. 제11항에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 1-A로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The organic light emitting device of claim 11, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by Chemical Formula 1-A:
    [화학식 1-A][Formula 1-A]
    상기 화학식 1-A에 있어서,In Chemical Formula 1-A,
    z1은 1 이상의 정수이고, z1이 2 이상인 경우 괄호 안의 구조는 서로 같거나 상이하고,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,
    Ar100은 치환 또는 비치환된 1가 이상의 벤조플루오렌기; 치환 또는 비치환된 1가 이상의 플루오란텐기; 치환 또는 비치환된 1가 이상의 파이렌기; 또는 치환 또는 비치환된 1가 이상의 크리센기이고,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,
    L100은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L 100 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    R100 및 R101은 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴알킬기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.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.
  17. 제16항에 있어서, 상기 z1은 2이고, Ar100은 2가의 파이렌기이며, L100은 직접결합이고, R100 및 R101은 각각 독립적으로 알킬게르마늄기로 치환 또는 비치환된 아릴기인 것인 유기 발광 소자.The method according to claim 16, wherein z 1 is 2, Ar 100 is a divalent pyrene group, L 100 is a direct bond, R 100 and R 101 are each independently an aryl group unsubstituted or substituted with an alkyl germanium group Organic light emitting device.
  18. 제11항에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 하기 화학식 1-B로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The organic light-emitting device of claim 11, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1-B:
    [화학식 1-B][Formula 1-B]
    Figure PCTKR2016010574-appb-I000113
    Figure PCTKR2016010574-appb-I000113
    상기 화학식 1-B에 있어서,In Chemical Formula 1-B,
    Ar101 및 Ar102는 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,Ar 101 and Ar 102 each independently represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    L101 및 L102는 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L 101 and L 102 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    z2 및 z3은 각각 독립적으로 1 내지 2의 정수이고, z2 및 z3이 2인 경우 괄호 안의 치환기는 서로 같거나 상이하고,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,
    R102 및 R103은 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,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,
    z4 및 z5는 각각 0 내지 4의 정수이고, z4 및 z5가 2 이상인 경우 괄호 안의 치환기는 서로 같거나 상이하다.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.
  19. 제18항에 있어서, 상기 Ar101 및 Ar102는 2-나프틸기이고, L101 및 L102는 직접결합이고, z2 및 z3은 각각 1이고, R102는 메틸기이고, z4는 1이고, R103은 수소인 것인 유기 발광 소자.The compound of claim 18, wherein Ar 101 and Ar 102 are 2-naphthyl groups, L 101 and L 102 are direct bonds, z 2 and z 3 are each 1, R 102 is a methyl group, z 4 is 1 , R 103 is hydrogen.
  20. 제16항에 있어서, 상기 발광층은 하기 화학식 1-B로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The organic light emitting device of claim 16, wherein the light emitting layer comprises a compound represented by Chemical Formula 1-B:
    [화학식 1-B][Formula 1-B]
    Figure PCTKR2016010574-appb-I000114
    Figure PCTKR2016010574-appb-I000114
    상기 화학식 1-B에 있어서,In Chemical Formula 1-B,
    Ar101 및 Ar102는 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,Ar 101 and Ar 102 each independently represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    L101 및 L102는 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L 101 and L 102 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    z2 및 z3은 각각 독립적으로 1 내지 2의 정수이고, z2 및 z3이 2인 경우 괄호 안의 치환기는 서로 같거나 상이하고,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,
    R102 및 R103은 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,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,
    z4 및 z5는 각각 0 내지 4의 정수이고, z4 및 z5가 2 이상인 경우 괄호 안의 치환기는 서로 같거나 상이하다.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.
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